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In this article, we hope to help you learn how to grow your online business monthly revenue from $0 to $10,000++. We are NOT about overnight success or viral tactics, which is why we call this process: Grow It Gradually 🦋.
👋 PLEASE READ: Before you scroll to the $10,000++ section, the idea behind this article is NOT to leap from $0 per month to $10,000++ per month overnight. That’s simply not possible. But, what is possible is to make small revenue jumps over time with your business. Remember, taking the slower 🐌🐢 approach to biz is still a successful way to grow!
We’re going to share 3 tips in each revenue “level” of your business so that you can Grow It Gradually 🦋. The five “levels” we’ve identified and experienced are as follows:
We want to make it EXTREMELY CLEAR that regardless of how much money your business makes, you are welcome and celebrated just as you are! There are SO many more important, more interesting measures of success and growth beyond just money.
But alas, in our experience, money can buy FREEDOM and that’s really what we want for you.
We hope, in each section of this article, you walk away with actionable takeaways for whichever level you’re currently at or striving to get to (at the pace is right for YOU!) Now on to the show…
Welcome to our Grow It Gradually 🦋 article where we’ll walk you through how to jump up 5 different revenue levels in online business. And as a final reminder, making more money doesn’t make you better at business or more important than anyone else 🤗.
When we were just getting started with our businesses, one of the biggest issues was trying to figure out what type of business and revenue model to pursue.
Online courses sound great, but if you don’t have an audience, who are you selling them to? The unfortunate answer is: No one 😩😩😩.
Software (aka SaaS) is cool, but if you have zero developer skillz (yes, skillz), it’s going to be a looooooong time before you can start making money.
Service-based businesses come in many shapes and sizes: Graphic design, web design, web development, virtual assistance, copywriting, art therapy, personal styling, social media management, the list goes on and on.
Essentially, you are a person with a specific skill, getting paid for the hours you work for someone else’s business.
This is a GREAT business model to start with because you don’t have to have a big audience or a social media following; all you need is to have cultivated a specific skill that you can monetize. With just a few clients in the door, you’re likely making enough money for a healthy side business (rather than a products-based business which would take significantly more sales and effort to make the same amount of money.)
💡 For the rest of Grow It Gradually 🦋, we’re going to use a fictitious business example so you can put yourself in the shoes of a fledgling biz and watch it grow. Let’s call our business… Oodles of Poodles Web Design 🐩🎨. Here at Oodles of Poodles, we specialize in helping people launch elegant websites on Squarespace. We focus on designing and building websites for small business owners in the health and wellness space. (Are we health and wellness experts? No! But we know there are many new businesses popping up in that niche and we love a good skincare routine as much as the next person, so we’re going to target them.) Our mascot is Prism, a lovable Poodle who has yet to learn how to build websites, unfortunately, but we’re working on training her! 🐩
Great, the (fictitious) business is established and we know who we can help [health and wellness experts] and with what services [Squarespace website design] we can help them with. Now, let’s get into the three tips in this section for Oodles of Poodles 🐩🎨 to get their business foundation right and their first client(s) in the door.
You may have noticed in the short bio for our fictitious business, we offhandedly threw out there our web design company focuses on helping small business owners in the health and wellness space. THIS. IS. IMPORTANT.
One of the biggest mistakes we made early on that we see new business owners make as well is NOT specifically stating who your business is for.
It may seem limiting to pick a specific group of people that can pay you money, but trust us, if you cast too wide of a net and just say you do “web design for small businesses” you aren’t going to ATTRACT 🧲 anyone. We’re going to go into more detail about this in the next section.
The other part of this first tip is to identify what exactly you do.
For Oodles of Poodles 🐩🎨, hopefully you noticed we wrote “build elegant websites on Squarespace.” We want to focus on the skills we have and the software we know how to use.
We don’t want to learn how to use WordPress, Wix, Weebly, Webflow, or any other website platform that starts with a “W” 😂😂. Plus, this is another way to attract a specific type of customer who uses the platforms you know.
Once you can answer these two questions, the logical first step is to create a website.
This is very important though: Don’t overthink this step! Give yourself a specific deadline of when your website needs to be launched for your biz. Constraints are incredibly important and we’ve all had those “under construction” pages up on our sites for longer than we should’ve.
Everyone open your ears… 👂👂… Are they open? Good. You ARE going to have to reach out to people before your business is “perfect.”
You ARE going to have to put yourself out there on a limb that’s a bit uncomfortable. We ALL do this!
To get your first couple of paying clients, you may need to do things like:
📌 *Related content alert: We recorded a podcast 🎙 episode titled, A foolproof way to get more clients, and it’s worth a listen if you’re at this stage of biz.
It’s really really really important to avoid overthinking everything early on in your business. Oodles of Poodles 🐩🎨 is not going to get its first paying client with hopes, prayers, and crossed fingers. It takes doing outreach and being proactive.
Promoting yourself ≠ being a sleazy salesperson. Those are not the same things. We love this quote from Tina Roth Eisenberg:
Head’s up: Be prepared that your friends, family, and acquaintances may criticize you for putting yourself (and Oodles of Poodles 🐩🎨) out there.
We’ve learned that nearly all criticism in business comes from other people’s insecurities and fears. Know this, and put on your invisible suit of armor, ready to ward off any unwanted criticisms of your new biz!
One thing we don’t see enough new biz owners do is leverage the “new-ness” of their business to create buzz early on.
Now, we understand being quiet is more natural to some people, but businesses need to be seen/heard before they can get paid!
Here’s what we’d do for Oodles of Poodles 🐩🎨 if we were just getting started:
Optional: If you’re a much more extroverted person, you could also do some sort of video launch. It could be done on Zoom, YouTube Live, IG Live, etc, and the entire call-to-action of your buzz-worthy event would be to attend that (instead of OR in addition to the email signup).
This type of launch event is not just about getting those first three paying clients. It’s about doing what we talked about in Tip #2: showing people your biz exists!
If you get a paying client, that’s obviously your main goal, but at this stage of the game, just getting people to know you are offering this service is critically important.
If you can work through these three tips, you should absolutely be well on your way to landing your first paying client (or two, or three!)
There’s no specific timetable on how long these things should take, but we’ll remind you of one important thing: You have to get started before you feel 100% ready! No one feels 100% ready at the $0 stage of business.
Next section, we’re on to our next stage and we’ll tell you what to focus on next once you earn hit that first $500/month benchmark. 🦋
⚡️ Tip #1: Be clear about what you do and who you do it for (ps. You need a website!)
⚡️ Tip #2: Start BEFORE you’re ready and courageously practice putting yourself out there.
⚡️ Tip #3: Create a buzz-worthy “launch” event.
Let’s say your business is generating around $500 every month and that’s about 500x better than $0, but you know $500 can’t pay all your bills, so you’re looking to grow. What do you do?
If you missed it in the previous section, we’re going to use our fake business Oodles of Poodles 🐩🎨 Design Studio (a company that does Squarespace website design for health and wellness businesses) as our ongoing example.
One of the most important ways you can grow your business is to get crystal clear on WHO your target customer is.
Even with our Oodles of Poodles 🐩🎨 business, we’ve narrowed in on “health and wellness” clients, but even that niche can be very broad.
Using the tips from the previous section, hopefully, you’ve been able to take on a few clients by this point, but since you’re still in that early stage you may have felt the need to say YES to each and every client inquiry.
That’s totally okay! But if you really want to grow, it’s time to get laser-focused on attracting a specific type of client. Think back to which clients you enjoyed working with the most, and try answering the following questions:
1️⃣ Is there a pattern to what these clients do? (Instead of “wellness companies” are most of your favorites actually yoga instructors?)
2️⃣ Is there a pattern to why they are looking for a [insert your business here] to help them? (Multiple clients have said they “don’t consider themselves creative” and “they are frustrated by trying to design their own website”.)
3️⃣ Is there a pattern to what they’re asking for? (Maybe you started out thinking you’d design 10-15 pages per website, but the best clients are happy with 4-6 pages.)
Just by answering those questions, you can paint a much clearer picture of the IDEAL customer you want to attract and how to speak to exactly what they want.
And where do you apply that lovely business-paint? You spell it out clearly on YOUR website and in all your promotional copy!
At the $500/month level of business, it can be easy to fall in the trap of taking on any client that comes your way because you’re afraid to turn down money. But we found from our own experience and helping many people over the years, saying yes to clients who AREN’T your ideal customers is the quickest way to NOT enjoy your work and to muddle your messaging. The quicker you can create cohesion and clarity in your portfolio and your website copy, the quicker you will see results of more and more ideal clients coming to YOU.
Back when Caroline 👩🏻🦰 started her first online business in 2014, a design studio called Made Vibrant, she marketed herself as a do-it-all-designer (hand-lettering, logos, graphic design, print design, branding, websites, etc.) She could apply her design skills to all these different projects, so why not cast the net as wide as possible, she thought.
After working with the first few clients of Made Vibrant, Caroline went through the questions we just posed in Tip #1 and found there was a more focused approach she wanted to take.
Instead of being a do-it-all-designer designer, she realized her favorite projects were designing brands for first-time creative entrepreneurs. She loved the feeling of confidence she could see in her clients after they had a clear and unique brand identity they were proud of.
This decision to stop being a jack-of-all-trades and instead develop a clear expertise in brand design is the point where clients finally starting seeking out Caroline instead of her always needing to go out and find them. It marked a turning point in the success of her business.
This approach is about being specific in stating exactly what your expertise is, exactly who you can help with your business, and exactly what makes you unique (and even a bit weird!). It’s Caroline’s version of becoming a Brand Designer. For Oodles of Poodles 🐩🎨, it’s about knowing that Squarespace sites for technology-frustrated yoga instructors is the sweet spot.
When you stop being vanilla and “for everyone,” you start to ATTRACT your ideal customers and repel customers who aren’t a good fit for you (sorry spa and gym owners, these poodles aren’t oodling for you!)
This approach is the ole “spray and pray” idea. You’re hoping if you keep things generic enough in your copy and promotion that the right customers will fall into your lap (amidst all the wrong customers).
Yet, what tends to happen is that you don’t get any customers because people don’t know if you’re the right fit. You get stuck in place and you end up taking on bad clients and doing work you don’t want to do.
By creating more clarity in who you want to help and how you can help them, you’ll 🧲 more of the right customers for your growing biz.
Remember, don’t be afraid to “repel” people at this stage of your business. The more you can become known for doing something specific really well, the better your chances are of getting paid to do that thing!
Buckle up, buttercup! It’s time to take control of your business and build an audience of people who care about what you have to offer the world.
⚠️ IMPORTANT: Any existing service-based biz owners might be thinking, “Hey, I’ve made it this far in my business, why would I start an email list and put extra work on my plate??” And the answer is three-fold:
The sooner you build an engaged audience (one that’s NOT at the mercy of social media algorithms), the sooner you’ll be able to start thinking about transitioning away from trading time for money. We’ll talk more about that in the next Grow It Gradually 🦋 levels below.
It’s a way for you to attract people out in the chaotic catacombs of the Internet and stay connected to remind them how you can solve their problems.
By showing up consistently in someone’s email inbox (where algorithms don’t punish you), you build trust and authority with them. You also give them a constant reminder of Tip #1 (who your business is for) and #2 (what your expertise is) in this email! Read more about our concept of “Marketing Bridges” here.
Using our trusty biz Oodles of Poodles 🐩🎨 as an example, we’re not just going to say, “Sign up for cute photos of Prism the poodle 🐩.” Instead, we’re going to have a bi-weekly email newsletter that shares A) a case study of an awesome yoga website and brand we found and B) a hot, new thing we learned in Squarespace. Okay, also C) an adorable photo of Prism doing something suuuuuper cute.
You want to attract 🧲 your ideal customers to your email list and consistently show up in their inbox on a schedule you can keep up with. These subscribers will hopefully become customers as you add in callouts for client availability in your emails!
⚡️ You can NEVER start an email list early enough. Trust us, even if one day in the future you were to pivot your entire business model (which we’ve done many times over the years), the right audience will move along with you. ⚡️
Having a captivated audience you can mostly control your interaction with is extremely important in business and will be absolutely mandatory to grow to the $1,500, $3,000, $5,000, and $10,000+ biz levels.
These three tips aren’t going to immediately help you jump from $500/month to $1,500/month in your business but, spoiler alert, no one has a silver bullet to help you do that.
We’re all about that gradual, sustainable growth 🦋 around here. It helps you keep balance in your life and to avoid burnout at all costs.
Next section, we’ll jump up to the $1,500/month level of business, with new tips to help you at that stage 📈.
⚡️ Tip #1: From your first few customers, can you look for patterns and identify a clear customer profile?
⚡️ Tip #2: Develop a clear skill-based expertise that people are searching for.
⚡️ Tip #3: Start building an email list… TODAY.
Our previous two sections have been about your client service-based business, and this section will be the last one in that arena before we start transitioning into scalable, digital products.
Too often, though, we see online biz owners try to make the leap into digital products too soon, while not building enough client runway to sustain the time that transition takes.
As a reminder, we are all about slow, methodical growth in business 🐌🐢,which often means sticking with client work for a while longer to avoid burnout and dips in business revenue.
When you’re at the $1,500 per month revenue mark with your client business, you’re probably not quite at the stage where you can cover all your bills with your profit (some folks may, and if that’s you, AWESOME 👏👏!) This is why our first tip in this section is to continually be investing time in your client outreach and potential client lead list.
Where do you find leads? Start with who you WANT to work with! Based on the previous 🦋 section’s tips, you now know the importance of getting super-specific about who your ideal client is. Use that info to search your social media channels for businesses and business owners that fit the criteria you established in the previous section.
By clearly knowing exactly who you want to work with it becomes much easier to search those clients out and put them in an outreach spreadsheet.
It seems like suuuuch simple advice, but we’d be willing to bet our merino wool socks most client-based biz owners do not have a client outreach spreadsheet. If that’s you, that’s okay! Now’s the time to fire up Google Sheets, Numbers, Airtable, Notion (aff link), or if you absolutely have to… Excel 😬🙈. Having a spreadsheet/database with a list of potential clients is how you keep your business organized and your leads nurtured.
🗓 Carve out one day per week to nurture your leads and create/send pitches! It is very unlikely that you’re going to grow your client roster at this stage of your business simply through your social media content creation (aka: posting on IG or TikTok) and referrals from the few clients you already have. You can’t sit back and have a, “they’ll come to me” mentality; you have to be thinking, “Let me go find them!”
This is why it’s key to put time on your calendar each week to invest in the future of your business! We actually have three sub-tips to this tip’s sub-tip 😂 #tipception:
New clients aren’t going to fall in your lap which means more money isn’t just going to magically appear in your bank account.
An easy trap to fall into when you’re starting a client business is to have one core service offer (which is great!) but then not give yourself permission to experiment 🧪 with other revenue-generating ideas.
For this second tip, we want to encourage you to think about a smaller, mini offer that isn’t a huge ongoing time commitment but could bring in a splash 💦 of revenue to your biz! A gradual splash, you know? A spritz. You get it.
If you recall, our fictitious business we’ve been talking about these past few sections is Oodles of Poodles 🐩🎨, a Squarespace design company for yoga instructors. The main offer (website design and build) can take weeks of work to complete, so let’s brainstorm 3 other offer ideas that require less time:
OFFER IDEA 1️⃣: Squarespace bug fix day – For $500, you’ll spend a day ironing out any bugs on someone’s site. These could be CSS-related, email form setup, page organization, etc.
OFFER IDEA 2️⃣: Squarespace site setup – For $500, you’ll hop in someone’s brand new Squarespace account and get all their pages set up (Home, About, Blog, Product, and Contact), their blog started, and their settings how they want them.
OFFER IDEA 3️⃣: Homepage redesign blitz – For $500, you’ll redesign someone’s homepage and offer them two layouts as a refresh from what they have now.
As you can see with these offer ideas, they don’t take ongoing work and can create a nice bump in monthly revenue. If Oodles of Poodles 🐩🎨 was able to land 2-3 of these per month, that could quickly help them add $1,500 in monthly revenue without any ongoing work.
⚡️💡 BONUS TIP: If you’re a savvy offer creator, your smaller offer could be a GREAT lead-in to your larger client package. Offer Idea 3️⃣ (homepage blitz) is a great example of this and could lead to someone starting with paying $500 but then wanting help implementing the design for a larger client package!
We like to think about foundation articles on your website like the old Chinese proverb about planting a tree: “The best time to plant a tree was 20 years ago. The second best time is now.”
Similarly, if you’re wondering when you should get some SEO-friendly articles published on the blog of your website, the answer is as soon as possible.
Foundation articles are great for short-term and long-term (gradual) business growth.
🩳 Short-term growth – Once you have your articles written and published, you can share them on your social media channels and try to convert those folks into email subscribers. Your articles become immediate marketing opportunities. They establish trust with your audience as your followers begin to see you as a source of expertise.
👖 Long-term growth – The goal one year from now is that the almighty Google (or Bing – LOL) has seen your article(s) as helpful for certain keyword searches and you’re getting organic traffic to your site which converts into new email subscribers!
If you’ve been putting off writing articles that can build organic traffic (which lead to new email subscribers) it’s time to stop delaying this task!
What are “foundation articles?” Plain and simple, they are helpful articles that can attract your ideal customer based on problems they’re searching for on Google. Shall we take a look at some examples for our friend at Oodles of Poodles 🐩🎨? We should?? Okay, then!
These are not perfect ideas BUT there are no perfect ideas in any part of business! You want to do a bit of search term research (which we did for those 6 article ideas) and adapt what you find to fit what your ideal customer is looking for.
📌 Related: Does SEO completely baffle you!? It used to baffle us to until we learned just enough and put that enough into practice. Learn everything we know about SEO here!
📌📌 Related #2: If you want to learn our full content strategy read our Content Salad Strategy guide (with even more foundation article advice).
Next section we’re going to venture past the client-side of growing your business gradually!
⚡️ Tip #1: Focus one day of your week on client outreach and new client pitches (build that spreadsheet!).
⚡️ Tip #2: Get creative with your client offers and experiment with a mini offer!
⚡️ Tip #3: Write 6-8 foundation articles that can bring you more email subscribers today and a year from now.
We absolutely HAVE to start this section off with a big disclaimer:
🚨 TRUTH ALERT 🚨
The stage of your business where you transition from clients (trading time for money) to digital products (more scalable offers) is a lot harder than most people would want you to believe.*
*Maybe those people are trying to sell you a product that makes it look “easy?” Remember that the next time you get sucked into a “how to grow your digital product biz to $X,000s in just 4 weeks” rabbit hole 😉.
The reality of online business is that it’s much harder, more stressful, and takes a ton more trial and error than you’re led to believe. We know you CAN do it, we just like to be 100% real about what it takes so that when you hit obstacles, you don’t think there’s something inherently wrong with you.
Now that your client business is humming along, you’re probably at max capacity and can’t grow your revenue much further because you don’t have any extra time in your day/weeks to take on any more clients. This is why building a digital product is sooooooo helpful, because it’s a scalable asset that can generate revenue well beyond what you could ever make with clients and the limitations of your time.
In our experience, we’ve found some of our most successful digital product ideas have been born out of our existing client service offerings.
For example, 👩🏻🦰 Caroline’s brand design business could only take on so many branding clients. As she got more and more requests, she realized she might be able to teach all her branding processes in an online course that anyone could take at their own leisure. Thus, Better Branding Course was born, a digital product that eventually replaced Caroline’s brand design business completely!
How do you validate that idea?
How do you make sure it fits within your current biz?
😱 We have an entire (paid) coaching session we’re going to let you watch IN FULL right now…
Our Identifying Your Offer 💡 coaching session replay will help you come up with a digital product idea that can be the foundation of your business revenue.
You came up with a digital product idea, happy dance for you 👏👏. Now, let’s build that sucker and give strangers on the Internet a way to purchase it from you. Whether you’re creating an e-book, online course, or paid membership community, these next tips should apply.
Annnnnnnnnd BOOM GOES THE DYNAMITE! 💥 You have a digital product in your business-arsenal! It’s a thing people can purchase from you that doesn’t require additional time investment the way your client service offers do. Hurrrrray! 🎉
Bringing back our ongoing example company, Oodles of Poodles 🐩🎨, a Squarespace design company for yoga instructors, the digital product they’ve decided on is: Squarespace website creation course for non-designers. This course will be targeted at folks who don’t have thousands of dollars to pay for their site to be done for themselves but they also don’t want to create a Squarespace site entirely on their own.
And here’s where the train goes off the rails for most folks who are trying to make the client-to-product leap. They 1) find their product idea, 2) make their product, and 3) sell it (ONLY) one time. And then… 🦗🦗🦗.
Life gets busy, clients pick back up, maybe the first launch doesn’t quite go very well (we’ve all been there!)
That’s where this tip comes into play and should absolutely help you generate ongoing consistent digital product revenue!
Your (new) digital product NEEDS a monthly promotion schedule. To create that consistent, gradual 🦋 revenue bump you’re looking for, it takes ongoing effort – especially early on.
Here are some digital product promotion ideas to try:
Hosting a free monthly workshop is a fantastic way to generate attention and potential buyers of your digital product. The idea is to solve a problem with the workshop topic, that people can attend for free, and then at the end of the workshop sell the digital product (which further solves the problem of the workshop).
Creating in-depth tutorial videos is akin to writing those foundation articles we talked about last month! You want to identify topics your ideal customer is searching for and create helpful videos that educate them on that topic. Then, in every video, make sure there’s a call to action to get more helpful info via the digital product.
If these two ideas don’t tickle your fancy, we have an in-depth article with 13 marketing blueprints you can steal and implement for your biz.
And just a friendly reminder: We started with client businesses, gradually transitioned into digital products, and now a few years later we only have digital product businesses that afford us the freedom we always dreamed of (both in time and in enough revenue).
It is absolutely possible for you as well it just may take longer than you’re being told by the “experts” out there.
⚡️ Tip #1: Create and validate your first digital product idea.
⚡️ Tip #2: Once you have a validated digital product idea it’s time to build it and make it available for purchase!
⚡️ Tip #3: Create a monthly promotion schedule for your digital product.
At this stage in your business, it may feel like you’re in constant juggling-mode 🤹♀️🤹♂️🤹 (you’re not alone!)
Our hope for this section is to share three tips that absolutely changed the game for us, but it’s important to remember these next tips came AFTER we did all of the things in the previous sections. Notice we’re going from $5k to $10k here, NOT $1k to $10k (that’s important!)
You probably read that tip and were thinking, “um, hey Jason and Caroline, how does honing my messaging help put dollar-dollar-billz in my bank account?” And to that, we would answer, “keep reading, ya silly goose! 😂”
Very quickly, let’s jump into the Wandering Aimfully (WAIM) Time Machine™ and take you back to the summer of 2019. Our WAIM business had been chugging along for almost two years, but we didn’t quite feel like we had our messaging locked in.
Here’s our exact monthly revenue back in 2019, sitting right between the $5k and $10k mark where it seemed to have stalled out:
The problem we were solving for our customers was a bit vague and our product itself wasn’t selling like proverbial hotcakes 🥞. We knew we could help transform the businesses of our customers, but that clearly wasn’t coming through in our marketing.
It was at that moment we decided to get laser-focused on what our core product should be, who it should be for, and how someone would know it was absolutely right for them.
Fast forward a few months and we did our first launch (more on this in Tip #2!) of our Un-Boring Group Coaching Program. This was the first launch of WAIM that really exceeded our sales goals, and we finally saw the traction we’d been searching for!
Those three items, together, are what helped us springboard to the next level in our business revenue. It’s soooo easy to continue to use the same messaging and copy you always have, but we believe you should be auditing these things often.
💡 PRO-TIP: If honing your messaging isn’t in your wheelhouse, we highly recommend finding someone who can help you do this. Investing in this part of your business is crucial at this juncture and is worth every penny to learn who you are talking to and what benefits you are providing them!
Open and closed launches are one of our favorite ways to generate our business revenue (especially to create a jump in 💰💰).
If you aren’t familiar with them, an open and closed launch is simply a set period of time when you “open the cart” and allow people to purchase your product. This creates the urgency to purchase but more importantly, puts YOU in control of when you have to be in sales mode.
We shifted our WAIM biz model to bi-annual open and closed launches back in 2019, and we’ve been loving the flexibility, freedom, and predictable injections of revenue ever since!
🤔 Is your messaging from Tip #1 resonating with people during your launch, or are they asking a lot of questions about your product/who it’s for?
🤔🤔 Have you had a bad launch before? That’s okay! Don’t compare a previous launch of a completely different product to what you’re selling now.
🤔🤔🤔 Does selling still feel icky to you? Prove to yourself that selling doesn’t have to be sleazy and that people on your email list/social don’t mind being sold to (when what you are selling can actually benefit their livelihood!)
If you get a launch or two under your belt and your customers aren’t buying at quite the pace you expected, consider offering a lower-priced “entry” version of your product. This is exactly what we did with that 6-Month Group Coaching package we mentioned. We still had our larger ($2,000) offer, but the coaching package was $100 per month for six months ($600 total, obvs). We found the “entry” product became a solid source of immediate revenue but then also led to those happy customers upgrading to our larger product when the six months finished up.
Hey….. Guess what, chicken butt? We also have a FULL coaching session within our WAIM Unlimited program called Sales Launch Start to Finish 🚀. This coaching session teaches everything we know about launching and what we’ve learned that works really well for our bi-annual launch schedule.
✅ You’ve nailed your messaging.
✅ You’ve done your first launch or two.
✅ You feel like you have all your business-ducks 🦆📊 in a row, it’s now time to find more ducks! (We know, we’re mixing metaphors in this section, it’s FINE.)
This is the tactic too many online biz owners jump to way too early in the game. They pour effort and energy into marketing, except the thing they are marketing (their offer) isn’t working that well yet so it’s (somewhat) wasted effort.
Sure, we always want you amazing humans to be doing more marketing than you currently are, but we don’t want you to expend all that effort without having all the foundational stuff in place.
That said, once you DO have your offer locked in, one of the MOST effective marketing tactics to get a bump in revenue is to partner up with someone who has a highly engaged audience in your product arena.
You want to find someone who is willing to share the spotlight with you and promote your product to their audience so they can make a sweet % of revenue without having to create your offer themselves. Your pitch to someone in this position is that you’ll give them as much as 50% of product revenue sold during the partner event and they’ll promote the initial signup of the event to their audience.
Example: Our friends at Oodles of Poodles 🎨🐩 (our example biz that does Squarespace design work for yoga instructors and also teaches a Squarespace design course) are going to partner up with a prominent Squarespace template company: Temptation Templates 💋🖥.
The great news about partnerships? There are MANY ducks in the sea! (We had to bring the ducks back and mix just one more metaphor in here).
If your first partnership doesn’t work out, figure out why. Just like one lackluster product launch doesn’t mean all launches won’t work, a partnership effort that falls flat doesn’t mean all partnerships won’t work!
And remember, especially with Tip #3, you’re NOT trying to do everything at one time. You can space these tactics out and you can tackle them on a schedule that works for your life and biz. We’re all about that slow 🐌 and steady 🐢 pace around here.
As with all of the tips we’ve been sharing these past few sections, these come from our very personal experiences.
These aren’t just theories we’re conjuring up from our business crystal ball 🔮, these are well-worn strategies we’ve implemented to help us make real jumps in our biz revenue.
We know these can work for you, it’s just about carving out the time to make them happen while having an experimenter’s mindset.
⚡️ Tip #1: Hone your product messaging. What problem are you solving for people?
⚡️ Tip #2: Do an open and closed launch of your digital product 🚀.
⚡️ Tip #3: It’s time to utilize effective partnerships.
It wouldn’t be a section in this article if we didn’t give a big, juicy caveat before sharing these last three tips with you:
Growing your business to $10,000++/month and beyond is NOT a requirement for a “successful business.”
It’s not the only way to reach your dreams and goals in life. Most of those can actually probably be done with less money (as many studies have shown). Always remember this, friend, when you catch yourself thinking your worth as a business owner can be measured in dollars. IT CAN’T.
These last tips will show you the exact steps that helped us take a leap to reach our “enough number” in business revenue, where we happily sit and don’t need to grow just for growth’s sake.
At this point in business, you most likely have a few content things going on: An awesome weekly email newsletter; a fun-but-helpful podcast; an info-packed YouTube channel; a pin-worthy Pinterest plan; an interestingly-designed IG grid, etc, etc.
But, what you might not have, is a clear directive and STRATEGY for each of those content buckets. You may also not have a clue if any of them are direct contributors to your revenue (if you do, kudos to you, we did not at this stage of biz 😂🤣).
📬 Your Email Newsletter: This is your real-time, value-packed piece of trust-building content with your audience. You want to have a clearly defined schedule your audience can get used to as well as a specific outcome they can expect with each email they receive. Then (and this is the strategy part) make sure you have a business objective being met in EVERY email as well as a lead-up plan for your product launches.
🎙 Your Podcast: This is one of your strongest connection points to your audience, even though podcasting is a very passive listen. The reason it’s such a strong connection point is because it’s a somewhat intimate relationship. People listen to podcasts while living out their day-to-day lives and you get to be alongside them in those moments! You know, doing the dishes, driving to work, walking the dog, taking a shower, etc. But the trick with making a podcast strategic is to ensure you have reminders of the product you offer in each episode!
We think you get the idea with each content channel, but the key is to make sure you’re not just churning out content without thinking strategically of how it can impact your business.
You might be thinking, “great, I can do all those strategy things, but how do I see the actual ROI of my content efforts??”
⭐️ SUCH A GREAT QUESTION! Thank you for asking…
You create a post-purchase survey!
A post-purchase survey is an embedded form or a linked form your customer sees immediately after buying your product. In that survey, you can ask a series of questions but one of the most important things you can ask is: “How did you hear about this product?” And you list out your content channels!
When we finally implemented a post-purchase survey (a Typeform embedded directly on our “thanks for buying” page), we found some really interesting data points:
That’s AWESOME for us to learn! Mostly because a content strategy can feel a lot like being on a never-ending hamster wheel. But, that hamster wheel gets easier to ride when you can see a certain % of your revenue comes from specific channels!
The post-purchase survey is also a great way to identify any content channels you might not be loving and thinking about cutting out. If your customers aren’t finding you through a certain channel, this can give you the data point you need to stop investing time and energy into that channel 💪💪. For us, this was Instagram and what helped us decide to stop using Instgram for WAIM at the end of 2021. (And our revenue has NOT plummeted since!)
Okay, we could write a 2,000+ word article just on creating an affiliate program, but we’re going to distill it down to the actionable stuff we hope can help you right away.
Adding affiliates to your business when things are on shaky ground is only going to cause headaches in the future (and create possible bad relationships). Our advice is to only move forward with affiliates if things are humming along smoothly!
For us, we use Affiliate WP (aff link) which is a WordPress plugin built by the same company that we use for our Membership Program (Restrict Content Pro – also aff link). There are MANY affiliate programs available so just be sure you pick the one that fits right with your website.
We do the following for our WAIM Affiliates:
The last thing you want to do is leave your affiliates feeling like they have to do everything on their own. You want to make their promotional efforts as SIMPLE as possible so it’s a no-brainer for them to promote and support your program.
As a fun note to finish off this tip, in our previous two WAIM Unlimited launches, affiliates have accounted for 50% of our new members! 👏👏👏 We’ve had a sizable jump in revenue with each launch due to affiliates and love that new customers are joining our program from existing members!
Once you work through the tips of the previous section and Tips #1 and #2 in this section, it’s probably time to pour a little biz-accelerant on your marketing fires.
What content channel is working THE BEST for you?
Is it your podcast? Your YouTube channel? Pinterest? IG? Etc? Whichever one it is, you want to identify it and brainstorm ways to pour biz-fuel on that wonderful, very safe and not hot, marketing fire 🔥!
Our last example for our dog-loving Squarespace compadres: Oodles of Poodles 🎨🐩 has a weekly podcast we told you about in Tip #1 called Grooming Squarespace 🎙✂️. Poods’ has noticed an uptick in podcast listenership and has seen a good amount of people have been visiting the podcast-only page they direct people to on their website for more helpful Squarespace Tips. They’ve also done a recent launch and noticed 15% of their new customers found them via the podcast (rad!)
Oodles of Poodles 🎨🐩 is going to focus on growing their podcast listenership by trying to appear on other podcasts. They take the time to research the top 20-40 Squarespace-related podcasts (or design-related podcast where Squarespace is mentioned) and they build an outreach plan to be a guest on these podcasts – making sure they only reach out to shows who have guests. Their pitch is to appear as a podcast guest and share an actionable set of Squarespace tactics most people don’t know about. This helps the other podcast hosts know value will be given to their audience and it’s not just a random pitch hitting their inbox.
Showing up on these other podcasts gives Oodles of Poodles 🎨🐩 a chance to promote their Grooming Squarespace 🎙✂️ podcast and increase their audience!
It might not be a podcast you’re going to amplify but the key in this final tip is to look for a marketing channel that’s already having some amount of success and growth and 🔥 it up a bit!
We couldn’t finish the final 🦋 section with just three tips, could we??
When we get asked how we run TWO online businesses and create all the content/stuff we create, with virtually NO team at all (we do have two developers for our software app Teachery), the answer is PROCESSES.
Need to write a weekly email newsletter? Here’s our process:
That may sound simple, but it’s a repeatable process. It’s what’s helped us write and send 800+ email newsletters over the past 8 years.
We have similar processes for our podcast, YouTube channel, articles, IG posts (R.I.P. ☠️), monthly live coaching curriculums, customer update emails, new products we build, new features we add to our software app Teachery, etc.
We also have daily, weekly, monthly, quarterly, and annual meetings together. Those meetings have a structure to help us know what to focus on and how to keep the WAIM Train 🚂 moving forward!
Good processes, ones that you hone yourself from experience and learning from people who do the things you want to be doing, are how you can get more stuff done AND not burn yourself out.
*We do want to acknowledge that not having kids (yet) makes our output a lot easier. That’s an intentional choice we’ve made. We also want to acknowledge our inherent privileges (things like our education, upbringing, being neurotypical) that we know contribute to our ability to create processes and execute within them. We know this might not be as simple for everyone, but we hope you’ll lean into what works for your brain, your life, and your circumstances!
⚡️ Tip #1: Dial in your content strategy.
⚡️ Tip #2: Create an affiliate program.
⚡️ Tip #3: Amplify the marketing bridges that are working!
⚡⚡️ BONUS TIP: All the tactics in the world are useless if you can’t get things done.
Hurrrrrraaaayyyyyyy for you making it through this Grow It Gradually 🦋 article (hopefully you didn’t just click through to this section looking for a silly GIF of us 👀😂).
There is NO straight line to success but there is a clear path we’ve followed and we believe you can follow too (with your own tweaks along the way!) Just remember: NO one jumps from $0 per month to making $10,000++ per month overnight or even in a few weeks/months.
What we’ve shared in this article is yours to come back to as often as you like! As un-boring coaches, we’re happy to support your journey as much as we can but YOU have to do the work. We can guide you and teach you from all our personal experiences but we can’t build your business for you.
You can do this.
You’ve got a plan of action.
Carve out the time and space but go at YOUR pace 🐌🐢🦋.
And now, your silly dancing GIF of us to celebrate!
Heads up: This post was first created on September 1, 2018 and the final entry was written on October 21, 2021 when we hit our Enough Goal! ✅ 😍
We’ve decided to publicly share our journey to making “enough” money with Wandering Aimfully. The idea behind this is not to show off how much money we’re making, the idea is to show exactly HOW we’re doing it.
One of our core values here at Wandering Aimfully (or WAIM, as we like to abbreviate it and will do throughout this post) is transparency.
Transparency becomes especially important to us when it comes to money because there are so many emotions and thoughts that often get tied to money (greed, shame, self-worth, happiness, embarrassment, etc), some of which can present challenges to the way we pursue our goals.
Before we get too deep into things, you might not know who the heck “we” are, in which case you may want to mosey on over to our About Page to learn more about us—Jason and Caroline Zook. If you just want the TL;DR version: We’re a husband and wife creative duo, with no employees, running our own businesses for over a decade, currently living and working together in Southern California. For good measure, here’s a super cute photo of us…
Now that we’ve met, let’s talk about this goal of getting 330 people to join our Wandering Aimfully Membership.
From years of experience, we know how it easy it is to get fixated on making more money. Yes, we know how good it can feel to see a couple extra thousand dollars in your bank account after a big launch, but we also know the mental toll it takes to constantly be in promotion, marketing, and sales mode. That’s partly why we’ve decided to give ourselves an “enough number.” When we finally reach this number, we can stop feeling the constant pull of promotion. We can focus fully on the amazing community we’ve built, rather than constantly be searching outside of the community for more members.
We also believe that defining your enough is the only way to ever feel satisfied. So often we focus on the vague word “happiness” without defining what it really is. We believe a big part of happiness is this notion of satisfaction. So, let’s explore for a second this idea of satisfaction.
One definition we found for the word satisfaction was:
The pleasure derived from the fulfillment of one’s needs.
Think of your wants and needs as an empty bucket. The pursuit of fulfillment is the quest to fill that bucket, and satisfaction is the pleasure you get from recognizing it’s indeed full.
But here is the root of why satisfaction seems to be so elusive:
How can we be fulfilled when we have no idea how big the bucket is we’re trying to fill?
Without defining what your needs are—without setting that benchmark—you will just keep trying to fill a bucket that’s endlessly expanding. That’s a recipe for a lifetime of discontent.
Instead, if you want to experience satisfaction (ie. happiness), you need to define how big your bucket needs to be…and then you need to recognize it when it’s full.
Or, in other words, you need to figure out how much is ENOUGH.
Getting to 330 paying Wandering Aimfully members within 12 months time will net us $33,000 in monthly recurring revenue (MRR). After we hit that number, we’ll close the proverbial sales-doors and stop accepting new members. We aren’t interested in continuing to grow our membership community (and make more money) just because we can.
In a highly digital world, we want to plan for and offer a personalized touch.
Why 12 months? Each month we’ll limit new memberships to 30 per month, so technically we should be able to get to our goal before 12 months (yay, math!), but we want to leave a bit of buffer in our membership signup planning especially because we know we’ll have some customer cancellations (aka churn). Limiting our memberships to 30 new people per month allows us to deliver as much of a personalized experience as we can, including some non-digital stuff.
Additionally, limiting the amount of new monthly members ensures that the community doesn’t feel crowed or overwhelming to our existing awesome members. It’s important to us to preserve the culture of the community, which we know to be one of our major selling points and differentiators.
For context, it might also help you to know how our membership pricing works. It’s very simple:
Both membership options include the exact same thing, the annual option simply saves someone a couple hundred dollars by paying in advance. If you want to learn more about what we include in our WAIM Membership, click here.
We’d be remiss if we didn’t mention some important advantages we have in this Journey to 330:
There’s no denying those are helpful pieces of this puzzle that we already have at our disposal. That being said, this is a new business offering for us and for our audience.
We told you we value transparency, didn’t we? Well, it’s about to get really real up in here.
A fundamental part of our approach to work and life is a philosophy we call Working To Live. Part of this ethos is the belief that living a fulfilling life begins with establishing our ideal lifestyle and then reverse engineering our business decisions to support and align with this lifestyle.
Using this approach, we first identify what we WANT, and then we back out how much money we need to get there.
That equation is how we arrived at our specific number of $33,000.
“We first identify what we WANT, and then we back out how much money we need to get there.”
That number may or may not seem outrageous to you. It’s taken a lot of restraint not to write paragraphs of text defending how much we spend in living expenses every month. But therein lies the problem when it comes to money: we constantly feel like we’re being judged or we feel we have to be on the defensive about our spending.
So, how about this as justification…We spend this much money every month to live lives we absolutely love. It’s awesome to be able to do that, right? We agree! But, it wasn’t always this way. In fact, it was just back in 2013 we spent $4,000 per month and could barely make ends meet (you can read our getting out of debt guide here).
Here are how our monthly living expenses break down in broad strokes:
*We don’t actually spend $2,000 on travel per month, but the past two years we’ve averaged spending about $20,000 on travel per year. We put this as a monthly “expense” to keep a watchful eye on it.
**Donating to causes we care about is a big part of our Journey to 330 goal as you’ll read in a moment.
Our business expenses have fluctuated quite a bit over the years due to how many different businesses and projects we have. That being said, one of our huge goals with starting WAIM was to streamline all of our projects into ONE membership and create a much more predictable set of business expenses. We believe this number is actually going to decrease over time, but for now we’re using a comfortable monthly average (which we’ll share more about in detail as the monthly updates continue to get added to this post).
Oh taxes, you necessary evil, you. First, we aren’t going to be those people that gripe about paying taxes. We understand and believe in taxes. This monthly average number will absolutely change over time, but we’ve decided to base it on our previous two years of business (taking what we paid in total taxes annually and dividing that by 12 to get a monthly average number). We do a /decent/ job of setting aside money for our taxes each year, but with a more predictable MRR going forward, this will get much easier!
Have you heard of this mystical thing in business called “profit??” It’s a pretty crazy phenomenon we’re just hearing about! It means that you don’t just spend every dollar your business brings in, but that you can keep some of it! It escaped us for a few years, but we’ve decided to utilize its wonderful powers going forward and put a much heavier focus on it 😂. Alright, jokes aside, our goal is to have $10,000 every month we can put into our savings, investments, and not touch at all. We’ve NEVER been able to predictably save a sizable amount of money each month and we want that to change.
It’s probably worth mentioning that we *have* been saving and investing the past few years, just not in a super regimented fashion. You can read how we currently invest and save our money here.
It can be really hard to give money to organizations and great causes when you can barely eek a profit out of your business. We’ve managed to redistribute some of our wealth every month since 2018 because we’re finally prioritizing it, but we want to do much more. Part of this Journey to 330 is to bake charitable giving wealth redistribution into our financial plan. We want to allocate 10% of our total monthly revenue to non-profit organizations, causes, and other acts of good that come onto our radar each month. The idea of having $3,000 every month that we can give away and help make a difference is something we’re really excited about!
**
Those five categories of money add up to $33,000. As a reminder, our goal is to hit $33,000 in monthly recurring revenue in 12 months (that would be by September 1, 2019). Will it happen? What are we doing to make it happen? Find out each month going forward by referring back to this post. We’ll add an updated section each month with how our launches are going, what we’re doing to reach this goal of 330 members, and how our feelings continue to evolve about this enough goal.
SPOILER ALERT: We absolutely did NOT hit our enough goal of $33,000 in just one year 🙈😬🤣. Boy, was that wishful thinking! Keep on reading to find out how we finally hit that goal after 3 years.
As of September 1, 2018:
Monthly Recurring Revenue (MRR): $4,783
Total Paying WAIM Members: 48
Monthly Profit and loss:
Total WAIM MRR: $4,783
Total WAIM Fees (Stripe/PayPal): $145
Total Expenses to Build WAIM: $16,500
Monthly Expenses in August: $7,460
TOTAL PROFIT: -$19,177 (eeeeek)
Quick hits of what we did to get this first group of paying members:
Ideally, we would’ve started this public journey at $0 MRR. Unfortunately, it takes a lot of time to put something like this Journey to 330 post together and we simply didn’t have the time while we were building our actual website and business. Every hour we had from March 1 – August 19 (2018) was spent bringing Wandering Aimfully to life. During that time we did a pre-order of our WAIM Membership and a first public launch.
In trying to keep this first update as succinct as possible (the irony is thick there), just know we spent five months planning, designing, building, working with developers, going through 400 of our past articles, riding a bunch of emotional roller coasters, creating our purchasing flow, and completing well over 2,000 tasks to bring this website and our membership offering to life. We also had a website dedicated to the behind the scenes of building WAIM, which was live from March 1 to August 19.
Before WAIM was finished being built, we knew we wanted to offer a pre-order for our memberships. We made this decision based on two things:
We opened up our pre-order for just one week, limited it to 30 buyers only, and sent three emails to a list of 400ish subscribers (this was a segment of our bigger list that had opted into daily-ish blog posts about how the build was going). Our three emails were fairly simple and explained the gist of the membership, the existing courses/workshops they’d get access to, and then a tease of what was coming in future months with WAIM.
There was only one hitch: We told our pre-order members they wouldn’t get full access to everything for at least a month (sell before you’re ready!)
While they’d receive access to our courses, this custom member dashboard we kept telling them about wouldn’t be fully coded for at least another month. Would people still pre-order if they couldn’t get the full experience right away? Well…
(You’ll notice the Airtable view of customers only shows 13 people and this is because two of our pre-order members canceled a few months in – sad panda. We’ll talk more about this in a moment.)
With our website finally up and running it was time to do our first official launch! August 20 was the start date and we would leave the “cart” open for one week, again limiting the number of buyers to just 30 people. This launch was quite a bit different from our pre-order because it also coincided with the website going live and we sent sales emails to our entire email list.
We decided early on that we’d write a behind the scenes journal sharing all of our processes, decisions, roadblocks, problems, and even share full unedited video meetings. From March 21 to August 5 we created and shared:
Here’s what that looked like…
Caroline’s previous email list (Self-Made Society): On August 5 Caroline mentioned that WAIM was coming on August 20. This was sent to 5,502 subscribers and 1,514 of those subscribers opened the email (27.5% open rate).
My previous email list (JasonDoesStuff): On August 7 I mentioned to my email list that WAIM was launching on August 20. This was sent to 11,538 subscribers and 2,477 of those subscribers opened the email (21.5% open rate).
Our first combined newsletter (Wandering Weekly): On August 13 we sent our first combined email newsletter prepping the subscribers of our new website and membership on August 20. This was sent to 16,684 subscribers and 2,411 of those subscribers opened the email (14.5%* open rate).
*Something definitely went wrong with this email broadcast. We actually reached out to our email provider and they admitted something looked weird. Unfortunately, we had too many to-dos on our list to diagnose things and didn’t want to try to resend the email with fear of something else going wrong or happening with our email reputation.
We shared teasers and whatnot on social media: While our social media follower numbers are nothing to scoff at, it’s important to note we also don’t see social media as a huge driver of new traffic or sales. Even though I have 31,000+ followers on Twitter, the engagement of even the most exciting of tweets is VERY low. Caroline has 2,900+ followers on Twitter, but I think she’d echo my statements about engagement (and she mostly just pushes her Instagram posts through to Twitter). Speaking of, Caroline wins our household Instagram award with 16,000+ followers; I have just a touch over 3,000 followers; and Caroline runs our @wanderingaimfully account which has 900+ followers. Those numbers are just to give you an idea of the impressions we’re working with. Numbers aside, we posted a handful of tweets with teaser images, shared a few stories on Instagram, and just generally kept people tuned-in to the launch date of August 20. Caroline did work some pretty awesome grid-magic on IG (as you may have noticed in the “Lead Up Stuff” image above).
This isn’t our first rodeo selling something over the course of a week. We knew we didn’t want to be writing and sending sales emails the night before (we’ve done that too many times and it’s stressssssful), so instead we whipped up a Google Doc and wrote all our sales emails in one spot.
Pro-tip: This is also a great way to get the subject line, preview line, links, etc organized ahead of time.
Then Caroline worked her wizardry in our email provider ( Drip [aff link]) to set up a “campaign,” which is just a string of emails with a simple sending schedule (shown above). Here is the timing of the sales emails along with the general topic discussed:
These emails were sent to our newly combined (as of August 13) Wandering Weekly email list minus the last email in the campaign because we hit our goal and didn’t need to send a “Last call” email. Who turns off one extra sales email during a launch knowing it would probably bring in more sales? We do. That’s who.
In the image below you can see the open rates improved greatly using this email campaign in Drip, as opposed to a normal broadcast email (very odd). And a couple email stats for you:
*Truthfully, we’re happy to see people unsubscribe as we know our content and membership isn’t the right fit for them.
35 new customers, what happened to 30? Ahhh, you are astute! So, a couple things happened which led us to end up at 5 buyers over the 30 number we set:
With that out of the way, let’s look at when people bought during the launch:
We offer credit card or PayPal as a buying option, so here’s the split on that:
*PayPal actually wasn’t working for the first four days due to two technical issues we missed. We finally got them fixed but have no idea if we missed out on folks who wanted to purchase via PayPal. Oh well.
And finally, the traffic to WanderingAimfully.com during the launch:
There’s no doubt in our minds that the initial launch is the most exciting time for people. It’ll be very interesting to see if we can keep up our pace of 30 new members each month going forward.
And now, the best and worst parts of our first official launch:
We can’t stress enough how excited we were to get Wandering Aimfully launched, but more importantly, to have a new group of amazingly talented and creative people in our community.
It’s hard to categorize anything as the “worst” part when things go pretty much to plan. If we had to mention something here, it would probably be how much stuff we have to do manually behind the scenes for a new customer that buys via PayPal. We won’t bore you with all the details, just know that each PayPal customer requires a bunch of manual processes that we’d love to automate in the future, but had to launch without (even though we tried to automate them months prior).
We’ll be using Baremetrics to track our member growth progress and revenue and you can actually view our public MRR dashboard here. Baremetrics is super neat because it helps you keep track of customers, revenue, churn, and lots of other powerful recurring revenue stuff.
A big shout out to Josh and his team for getting us hooked up on Baremetrics and making it really easy to update our Airtable with actual monthly revenue.
**
That’ll do it for this first update! Now, it’s time to get to work on creating new stuff for our WAIM Members and executing our plans for the lead-up to our October launch.
👍👍
As of October 10, 2018:
Monthly Recurring Revenue (MRR): $6,350
Total Paying WAIM Members: 62
Monthly Profit and loss:
Total WAIM MRR: $6,350
Total WAIM Fees (Stripe/PayPal): $160
Monthly Expenses in September: -$3,496
TOTAL PROFIT: $2,854
Quick hits of what we did to get this first group of paying members:
This is our second update on our Journey to 330 and man-oh-man do I have ALLLL the thoughts to share. If you are unclear of our “growth strategy” with selling our Wandering Aimfully Memberships, the goal is to open the doors every month and only allow up to 30 new paying members. One thing that you’ll notice between the first and second update is that our assumption about our expenses was correct. We can’t live off the $2,854 in profit we made this month*, but it’s great to know that our business is not making more money than it spends (after just two months!)
*If you’re wondering how we’re keeping the lights on since we aren’t making the profit needed to cover our total living expenses, we have ongoing payments from our previous BuyOurFuture project as well as revenue from a few other online courses and software products. Truth be told, these Fall months will be tight financially and we hope we don’t have to dip into our savings!
Looking at the month of September, we had a hunch that the luster would wear off during our second launch and I’ll talk more about that in a moment. But, one really big thing happened between the first launch and our second launch and that is that life took a big steaming 💩 on our faces…
You know that phrase everyone (including us) like to throw around: “Plan ahead because life will shit on your face.” Well, it happened to us in a big way in September. My lovely and very healthy wife mentioned she had some tightness in her neck at the beginning of September and a few days later we found ourselves in an Urgent Care doctor’s office hearing that Caroline was diagnosed with shingles. Oof.
I’ll save you all the intimate details of how bad shingles can suck, but here’s the painful timeline of how it went down:
Those five weeks happened between the first launch and second launch of Wandering Aimfully and unfortunately, it left us a woman down in the work department. While I tried to carry my weight and tow the line of everything we had going on (and keeping my other business ventures afloat) I spent the majority of my time trying to give Caroline any ounce of comfort possible. It was difficult not being able to work like we normally do, but truthfully, it was an emotional few weeks for me and an insanely few painful/emotional weeks for Caroline.
I don’t want this entire update to be about our run-in with shingles, but it’s worth noting that you DO have to prepare for these life hiccups to happen. You can be mad about it, you can be frustrated about it, but you can’t just fast forward life so you hunker down and deal with it the best you can.
I’m happy to report that Caroline is feeling 1000% better than she was during week one of shingles, but she still has some lingering issues (which we’ve come to discover are normal).
Earlier on in the summer, we made the decision to create a podcast and YouTube show where we’d talk about areas of life where we’ve wandered aimfully and share our experiences, stories, and lessons learned. Originally we were going to launch the show at the time of launching the website, but Caroline had a good idea to push the launch date of the show back a month so we’d have something fun to announce after the luster of our new website announcement wore off (good idea Carol!)
I’ve had a few podcasts over the years and one of the most important things I’ve done for my sanity in running them is to get AHEAD of the publishing schedule. We still had a ton of work on our plate during the summer months, but we carved out time to record five initial episodes of Wandering Aimfully: The Show. This was a clutch move because we couldn’t record a single thing in September and it was nice to know we had five weeks of episodes already recorded and ready to be edited.
I don’t want to spend too much time on the production of our show, but just know that:
I could, and may, write an entire article devoted to our plan and strategy with our podcast/YouTube show, but the short of it is we want to create a show that we’d enjoy watching. Our assumption is that we’ll deepen the relationship with our existing audience through the show, having them (you!) feel a connection to us that you can’t get through the written word. Could we see some external growth with our show? Maybe. But that’s kind of out of our control, so we’re not focused on that.
As of writing this second launch update, we’ve released five episodes and the total views/downloads are just around the 3,000 mark. To some people, that may be great! To others, that may not seem worth the 125+ hours we’ve put in. To us, we’re committing to the show because we enjoy it and we want to see how it goes for a few months.
EDITOR’S NOTE: After reading back through this section of the update I posted a note in the Wandering Aimfully Slack channel about how much work was going into our show and not being sure if it was actually going to pay off (just some straight-up #realtalk). I heard back from many of our members that they loved the show and it was doing exactly what we intended it to do. Plus, a few newer members said the podcast pushed them over the edge to join WAIM. So… hurray testing assumptions!
As you’ve read and understood, our goal is to get 30 new paying members each time we open the WAIM Membership doors. We are not naive and we understood that there would be a natural drop-off in membership with our existing audience.
As our October launch approached we were trying to figure out the best way to sell our memberships, but not oversell it to the folks who went through our full 7-day sales sequence just a few weeks prior. Here’s what we ended up doing for our second launch.
This group was made up of new email subscribers who went through our 5-day welcome email sequence and did not get our first launch sales sequence.
We dropped these folks directly in the same 7-day sales sequence we used before:
And the most important stat of all? 8* people purchased!
*Unfortunately, we don’t have concrete data to say that our email sales sequence was the sole reason these folks purchased, but they were all in that group of 408 subscribers, so we’ll take it! Also, we’re going to try to track conversions from the 7-day sales sequence better during our next launch (always room to improve).
I’m gonna be brutally honest and just come out and say it: I’m nervous that our email provider is having email sending issues. I’ve heard from another customer of Drip that they’ve seen a huge drop in email open rates, but it’s crazy to me that we went from an average of 20-25% open rates down to 10-15% since switching to a combined newsletter with a new from email address. That’s probably a topic for an entire other discussion, but we can’t do much about it now, so… let’s move on.
We sent our existing subscriber group three emails during our second launch:
Email #1: A normal newsletter about taking risks which aligned with our podcast episode that had a callout that memberships were open at the top (14% open rate).
Email #2: A dedicated sales email three days later focusing on wins our WAIM members shared with us with a bit more of a pitch to join (13.5% open rate).
Email #3: Another normal newsletter on the last day of the launch about confidence with a reminder callout that memberships were closing (11% open rate… but this data is written one day after sending that email).
It’s safe for us to assume that 8 of our new customers came from these emails.
So, where did the other 2 customers come from? Well… They found us completely out of the blue and joined in the last few moments! No joke. I emailed with both new customers who weren’t on our list and they said they hadn’t heard of us before joining but felt a real connection to us and WAIM and decided to take the leap. Pretty cool!
Honestly? And most people would probably try to hide behind fake optimism… It sucks. It sucks to put something out into the world that you truly believe can make a difference for folks, but to not see the conversions happen.
BUT… We knew it wasn’t going to be easy to get 30 new paying members each month and we also knew that September was a really tough month for us.
If we take a step back we can see that we have 18 new (awesome) members who believe in us. We can see that we didn’t do much marketing or promotion at all, with exception to launching our show (which, as stated, is more of an audience deepening decision, not a widening one). And you know what’s better than a big fat 0? 18! There is a tinge of discomfort that we missed our 30 mark, but, we’re grateful to have new members AND our existing group who continue to stay active members.
We have a second launch under our belt after having a pretty damn rough month personally. We still ended up with new members and even though we didn’t hit our goal, we were able to test some assumptions about the groups on our email list we could sell to.
Let’s finish up with the BEST and WORST…
We got some new members! 18 is way better than 0. The quality of the members of the second group seems to be on par with the first group (which is rad!) We were also really stoked that brand new subscribers converted to paying members, which bodes well for the future of our email marketing plans.
There are two things I want to share and you probably guessed the first one: Poor Caroline had to deal with shingles the entire month. It. Was. Awful. But, we made it through and she’s feeling so much better. Could’ve been worse!
The second worst part I wanted to share is that 5 customers canceled their memberships. Personally, I have some soul-searching to do on how I deal with people canceling, especially after only being a member for one month. I get it, people will cancel, it’s the name of the membership game… but that doesn’t mean it doesn’t suck and it doesn’t make me feel emotions (even though most of the time I have the emotions of a robot).
The silver lining to having people cancel is that we get to learn why they canceled. We can find ways to improve or to make our membership better. We absolutely believe WAIM is worth the $100 per month, but we also know we don’t have the best onboarding process for our new members. Hoping to spend time on this in the next few weeks!
**
Hope you enjoyed our second update on our Journey to 330! It’s as much a reminder to us as it is to you that reaching your goals isn’t going to happen overnight. It’s also not going to happen just because you hope and dream it will. You have to put in the work and you have to prepare for things to go wrong now and again.
As of November 15, 2018:
Monthly Recurring Revenue (MRR): $6,133
Total Paying WAIM Members: 62
Monthly Profit and loss:
Total WAIM MRR: $6,133
Total WAIM Fees (Stripe/PayPal): $128
Monthly Expenses in September: -$3,590
TOTAL PROFIT: $2,415
Quick hits of what we did this month:
Holy moly, where do we begin this month? Well… Let’s just go ahead and rip the band-aid off and jump right into the biggest emotional topic.
This is a very weird sentence to type, but we’re kind of glad our MRR went down. Wait, do we hate making money? Are we gluttons for punishment? Why the heck would we be happy that our MRR went down??
Here’s the deal, and it’s my belief it’s going to make total sense after you read this:
We like to see some tension. We need relatability. We need something to go wrong so we can see how the hero(es) overcome the adversity.
Now, if I’m being honest, I’d rather that drama didn’t involve how much revenue we generate, but it is what it is. The fact of the matter is that between October 10 (the end of our second launch) and November 12 (the end of our third launch) we had more people cancel than we had signup. OOF. Not great.
I’m the one who more closely watches our WAIM Memberships and it was a punch to the gut every time a cancelation email came through. All-in, we had 12 people cancel their WAIM Memberships which increased our User Churn to 16.9% (industry average is 11%).
The wise and experienced co-founder of Basecamp, Jason Fried, once said that you learn the MOST about your product right when a customer signs up or right when they cancel. When a new customer joins, ask them why and find out if there are recurring things that are attracting and converting people (and do more of that!). When a customer cancels, asks them why and try to fix that problem asap. So, that’s exactly what I’ve been doing with every WAIM Member who’s canceled.
I would have expected members who canceled to say things like: You guys aren’t as helpful as I thought or Your products aren’t what I expected or I just expected something completely different. But, we didn’t hear any of that. In fact, we’re seeing people cancel their WAIM Memberships because we have TOO MANY products. We’re hearing that folks believe in the value of WAIM, but they were overwhelmed by all the products available and not sure where to begin. And while that might seem like a good problem to have, it’s still a problem that needs fixing because it is causing people to leave.
Can I just pause for a moment and be brutally real with you… Emailing people and asking them why they canceled is humbling. It’s not fun. But, if you’re trying to build something that can last and that can make an actual impact for your customers, you have to push through the uncomfortable moments. Every time I hit send asking people why they canceled it feels crappy. But it’s necessary, and I’ll continue to do it.
I’m going to save the answer to this question until the final part of this month’s Journey to 330 update. For now, let me take a break from talking about everything that went wrong and share some stuff that went RIGHT!
One of the things Caroline and I enjoy most is teaching live workshops. Caroline is amazing at coming up with frameworks and processes that we can use ourselves and pass on to others. The live video element takes me back to my IWearYourShirt days where I hosted a 1-hour live video show daily for nearly 5 years straight (yeah, you read that right!) There’s something about the energy of speaking to people live and getting immediate feedback that lights us both up.
This workshop was initially supposed to happen during our second launch but with Caroline still not feeling great we had to postpone it a bit. Instead, we held the workshop on October 18 and had 232 people register. Of those 232 people, 139 showed up to the event which is a whopping 61.5% attendance rate (that’s RAD!)
We didn’t have anything to sell on the workshop, so it was just 100% value-driven. That being said, we did have two people email us after the workshop who thanked us and said they would be joining WAIM because the workshop was so great (and they both stuck to their word and signed up during our November launch – wahoo!).
For a while, we’ve wanted to have WAIM Member co-hosted workshops as there are some really talented and smart people in our community. One member, in particular, has been an all-star since joining what WAIM was previously known as: BuyMyFuture.
That member is Brendan Hufford and he’s been an incredibly valuable community member. Brendan lives, eats, and breaths SEO, so whenever someone has a question in our community Slack channel, Brendan is all over it (or if I beat him to read it, I’ll tag him and then he’ll reply).
Through a few random DM convos, Brendan and I decided it was time to do a basic SEO workshop as well as share a really nice Custom Google Analytics Dashboard that’s perfect for content creators.
This workshop was for a much smaller audience, just our paying WAIM Members, but I was still stoked we had 83 people register (20% of our total community) and a 55% show-up rate. Even better than that, the comments at the end of the live workshop and afterward were incredibly positive (it helps that Brendan was a teacher in his former life, so he’s great at hosting and keeping people engaged!)
Truth be told, we didn’t plan to do this workshop when we started our third launch of WAIM Memberships. However, because we missed doing a workshop during October’s launch, we decided to squeeze this one in and do it during the final day of our 1-week launch window.
We had 193 people register for the workshop and another great show-up rate (56.5%). I believe we had people attend from 25 countries around the world for this one, which is really neat!
The big experiment for this workshop was to have a sales pitch for WAIM Memberships at the end. The workshop itself was approximately 45 minutes of teaching and 15 minutes of selling. We unveiled a new plan in the works, which again I’ll get to in a moment. Here’s what the sales slides looked like:
We’re not new to selling on live workshops, especially me. That’s actually something I got really comfortable doing 2013-2015. You can imagine my surprise when we had… drumroll… zero sales. Not a single person bought during the workshop and only one person bought when we sent out a follow-up reminder email that the doors were closing for WAIM Memberships.
Which, leads us to two final updates this month…
This is part of the discussion about members canceling due to feeling overwhelmed. While we can solve many problems with the 30+ products we provide in WAIM, it’s too much to choose from and feels like we’re not addressing a bigger problem we can solve for people.
As we’ve watched our membership join rates decline from August (first launch), October (second launch), to November (third launch), it’s apparent to us that something is missing the mark. That something is what we’re going to hunker down and focus on next.
Sometimes you don’t have a crystal clear change to make in your business when things aren’t going exactly as you want them to go. It would be an entirely different story if people were canceling our membership and saying, The courses are crap, The other members aren’t around, and You guys aren’t who I thought you were. Thankfully, NO ONE is saying those things (at least not to our faces or email inboxes – haha). But if people were saying those things, we’d have an idea of exactly what to fix. Instead, we’re making a best guess based on what our gut is telling us.
We’re going to create a new 6-month program that’s laser-focused on solving a big problem for a specific type of person and focus the entire membership around that core program.
You may have caught a glimpse of this in the sales slides I included a GIF of a few paragraphs ago, but this is where we’re taking a big leap of faith. We’ve known from the beginning that what you get with WAIM is a bit too generic. We’ve always loved that our resources can help people at different parts of their business journey (not started, beginning, intermediate) and that what we teach can apply to different types of businesses (products and service-based business) BUT just because your product can do something doesn’t mean that’s how you should market it. Trying to solve everyone’s problems at once makes for some pretty diluted marketing. Our selling proposition doesn’t speak enough to a specific problem that people have or can clearly articulate. That’s a recipe for disaster when it comes to selling anything. I believe we got as far as we did with this generic approach only because we’ve worked so hard at building trust over the past few years.
Going forward, we want to focus on this singular pain-point:
Wandering Aimfully is the membership community that teaches you how to turn your creative skills into a profitable digital product business, without sacrificing your lifestyle in the process.
To accomplish that, we’re creating a 6-month program that’s the MAIN focus when people join WAIM. They can get everything else (all 30+ previous products) but we’ll position that stuff as “in the vault.” While we’d love to rest on our laurels and believe all our previously created content is good enough to solve problems for people, we know we can do better. We know we’ve learned a ton and that we want to give a more concise and updated plan of action for our members to follow.
One of the core tenants of this 6-month program is giving you a framework to follow that helps you avoid burnout. Unfortunately, we don’t have the luxury (read: cash flow) to take the next 6 months to build this program. Instead, we’re going to have to reduce any other tasks or commitments and hunker down to build something great, free from other distractions.
Should be run, right? Well, we’re nothing if not up for putting in the work it takes to succeed. We will absolutely do our best to stay balanced and not overwork ourselves. (Definitely no intention of going shingles Round 2 in this house!)
It would be easy to sum up the past month as a “bad” month due to a smaller launch and higher rate of member cancelations, but it wasn’t bad. Caroline’s health improved. Our existing members are happy, excited, and getting value from what we’re doing. We are making a difference for people, providing value to them, and enjoying most of the process.
We realized that we need even more clarity and focus around what WAIM can provide its members, what specific problem it can solve, and who it would be a great fit for.
And of course, the fact that we did get some new paying members was great!
Watching 12 people cancel their memberships between the second and third launch. As helpful as learning from the cancelations is (and it may end up being the catalyst that helped propel us toward our Journey to 330 goal faster), it was a punch to the nether-regions this month.
**
Phew, what an update! We really hope you enjoy these. It’s the exact type of content we love, especially when things aren’t going perfectly so you can see how people overcome adversity (it just kind of sucks to be the ones having the adversity!)
As of January 30, 2019:
Monthly Recurring Revenue (MRR): $6,917
Total Paying WAIM Members: 73
Monthly Profit and loss:
Total WAIM MRR: $6,917
Total WAIM Fees (Stripe/PayPal): $342
Monthly Expenses in September: -$2,963
TOTAL PROFIT: $3,639
Quick hits of what we did this month:
There is a tonnnnn to get caught up on but we’ll start with the unfortunate part of this update…
The holiday season was a blur and the new year started off on a great foot for her, but then it all came to a screeching halt in early January.
Instead of hiding her anxiety, we shared what Caroline was going through with our WAIM Members and on social media and the response was amazing. We can’t thank you enough if you sent kind words and thoughts our way.
While we were still able to do our January WAIM membership launch, we decided that we would push back the start date of our new program Build Without Burnout Academy and remove every work item from Caroline’s plate. We’re hoping a month of rest and easing back into just a little bit of work each day is what Caroline needs. She’s also trying everything under the sun to fight her anxiety (meditation, CBD, relaxing teas, extra sleep, therapy, and anything else folks have sent us or she’s read about).
With shingles hitting Caroline just a few months ago we are certainly trying to listen to the universe telling her that something isn’t quite right.
We’re doing our best to create space and avoid any stressors at the moment.
We teased this in the previous update, a 6-month program around a more specific problem and target audience.
We’ve had many conversations about WHO our membership is for and WHAT problem we’re specifically solving based on our experience. We knew the initial positioning of our membership was vague but we simply had to start somewhere (and hey, it did work and attracted over 60 paying customers!)
That being said, one of the things we always talk about when people ask us for advice is to niche down and get as focused as you can. We took our own advice and had multiple conversations about what that meant for us and WAIM.
We have A LOT to say on this topic. We also have tons of tangible and practical advice we can give because we have firsthand experience and lessons learned (always a good sign!)
One of the first things we did was to rewrite the mission statement for our WAIM Membership…
Previous version: The essential membership community for independent creatives who want to earn more so they can live more.
New version: The membership community that helps client-based business owners transition into selling digital products—without burning out in the process.
I mean, yeah, pretty damn clear that we were talking to an extremely broad group of people with our previous version.
With this renewed focus of WHO our membership was for, we knew we hadn’t created a product within the membership that spoke directly to that audience and could help them (the WHAT). This is where our Build Without Burnout Academy product comes in!
We had many conversations and planning sessions about Build Without Burnout Academy. There were a few key components it had to have:
But the main component was that we’d have a brand new program to add to the WAIM Membership that would hopefully speak more directly to our target customer (and add value to the membership!)
We looooved how it all came together. Caroline did a wonderful job branding the experience, from the program curriculum, slide design, the experience within Teachery our members will go through, and the amazingly fun game board game element that accompanies the educational content.
We wanted to kick things off January 29 and have all our existing WAIM Members and new members from our January launch start together on their 6-month journey. With Caroline getting hit with anxiety we had to make the tough call to push the start date back to March 4. It wasn’t that we needed one more week to finish things, it’s that we care more about Caroline feeling normal so she can give her whole self to our members (and you know, feel normal!)
If we need to push the start date back again, we’ll cross that bridge when we get there. We’re taking it day by day and our members have been amazing about it.
Originally, our plan was to do a launch in December, but we decided to nix it due to the workload we had for Build Without Burnout Academy creation and our holiday travel schedule.
The January launch was the first one to our full email list since October. We felt comfortable it was enough time removed, plus, with the new mission statement and focus on Build Without Burnout Academy there was reason to share it with our full group of email subscribers.
As you can see we’re still dealing with churn and had 15 members cancel between our last launch (November 15) and the end of our January launch.
We’re not assuming churn is going to disappear but we’re hopeful that our new 6-month guided program helps our members see this is a commitment for longer than they may have previously. That’s the hypothesis we’re going to test.
It’s awesome that we’ve had 100+ people sign up! It’s not so awesome that nearly 30% of them have canceled. Then again, even with industry standard churn being 7-15%, maybe 30% isn’t so bad given that our membership doors have been open for nine months (including our pre-sale in May 2018)?
This is incredibly interesting to us because it shows that the personal touch and direct communication goes a long way in making the sale.
This was also a very interesting realization as it showed us that we may have been using the wrong sales tactics the past few months. We’ve been applying our sales knowledge from digital product launches and we’re not selling a digital product anymore, we’re selling a monthly membership.
It’s clear to us that there’s a lot more trust needed for someone to make the purchase with a membership.
I shared a few tweets when this thought occurred to me (copying + pasting our online course sales to our membership sales process) and Amy Hoy jumped in to back me up:
So…. How do we move forward with our sales process?
Realizing that I’ve had some sort of direct interaction with our last 40 customers, and I didn’t hate doing it (important!), is a clear indicator that we should try a more hands-on sales approach. If I’m already emailing with folks during our monthly launches, why not just remove the work that goes into the monthly launch model and put it into something that’s more personalized and possibly takes the same amount of effort on my part (but makes the customer feel better)?
Quite simply I’m going to create an online course that uses the lessons to preview different aspects of the WAIM Membership. Each lesson will have a short video and we’re going to highlight these items as “lessons”:
The final “lesson” in the test drive experience will be a sales pitch to join. Essentially, our membership doors will be open ongoing, but you won’t know that unless you take the test drive AND you make it through a few lessons (read: you show interest and go through the content!)
One note about the sales pitch lesson: There’s no sense of urgency or countdown timer since the test drive is simply just open all the time. My thought is to be 100% honest about that and point it out. Hopefully that directness will be a replacement for the missing timer or BUY NOW OR ELSE copy. We’ll see.
Seems pretty simple, yeah? My goal is to keep the test drive process as frictionless as possible but make sure someone has to enter their email in some way to get access to the test drive content (hence the entire point of this, having direct communication).
This doesn’t scare me. It’s also not something I plan on doing long-term. I’m looking at it as an experiment and if it’s too many people and none are converting, I’ll stop.
However, we want to see if the test drive experience and the personal email outreach helps us convert new members. Again, I’ve basically been doing this during our monthly launches already, so instead of cramming all my effort into one week per month, it’s spreading that workload out based on the schedule of people who sign up and show some interest.
Our goal is to get the WAIM Test Drive up and running in the next few weeks. Even if Caroline isn’t feeling up to recording any video, I can have some fun with that and record solo. As with everything, just get started even if it’s imperfectly.
Note: I’m also going to be taking a social media detox for the month of February which will immediately free up the extra time that will go into creating the Test Drive and doing direct outreach throughout the month.
Like anyone else, we’re doing our best to keep things moving along. The most important thing for us is to have Caroline recover and get back to feeling normal.
I’m going to skip the BEST and WORST part of the recap because this update is already reaaaaally long and in-depth. Plus, instead of thinking about what we don’t have yet in regards to our goal, let’s zoom the lens out and see what we do have…
We’re super appreciative that you take the time to read these updates and hope they help you on your journey to your own version of “enough.”
Have anything you wish we’d talk about? Want to give us feedback? Shoot us an email and let us know.
As of March 30, 2019:
Monthly Recurring Revenue (MRR): $8,917
Total Paying WAIM Members: 97
Monthly Profit and loss:
Total WAIM MRR: $8,917
Total WAIM Fees (Stripe/PayPal): $400
Monthly Expenses in September: -$3,625
TOTAL PROFIT: $4,892
Quick hits of what we did this month:
Let’s start this fifth update off with the huge win of the past two months. We knew our monthly launch model (what we started with back in August) was an experiment in itself. We didn’t know how it was going to work out and fortunately, it did have positive results, just not quite as positive as we needed to reach our enough number in a timely manner.
We didn’t have a second way of selling WAIM Memberships in mind when we started the monthly launch model. We had that experiment and said we’d give it around 6 months and then pivot from there.
Our previous monthly launch model was converting at .05% (through monthly email sales campaigns).
Our new model for selling WAIM is currently converting at 6%!
What did we come up with to improve our sales conversion? I touched on it the previous update, enter the WAIM Test Drive (this is the introduction video)…
In late January I had a small epiphany, I went through our WAIM customer list and realized I’d emailed back in forth with ALL 40 of our most recent members. Yes… 40! At least one email back and forth before they purchased. Hmm, okay, now what to do with that data point?
The WAIM Test Drive would try to encourage 1-on-1 communication with folks interested in WAIM. If I could up the percentage of people coming to the WAIM website to start a conversation, the odds seemed to be in our favor they’d become a paying member.
You can think of the WAIM Test Drive as a simple online course where the lessons act as sections to further explain a WAIM Membership. This allowed us the ability to showcase the most important sections of the WAIM Membership and give a bit more detail than we could on a sales page (along with a more personal touch).
The WAIM Test Drive includes 9 “lessons” and each one shares a different part of the membership (the one above is where we speak honestly about WAIM and how we’re not “6-fig launch” people).
Our assumption was that if someone was interested enough to sign up for the test drive, they would be more likely to watch a few videos and see what’s behind the proverbial curtain.
The only automated part of the WAIM Test Drive when it started was that someone signed up for it and could see the content right away (thanks to it being built on my online course platform Teachery). The rest, I handled manually:
Now, reading those bullets you might be wondering why I didn’t automate that process right away? It seems fairly simple, yeah?
The short answer is: Yes, I absolutely could’ve automated it. But…
The longer answer is: I wanted to do things manually in the beginning to test a few assumptions about the test drive itself. To see if it actually worked before taking the time to automate it.
Does that sound familiar to you? So many of us in the online biz world are guilty of trying to automate and create passive income before it’s actually viable.
Yep, that meant manually emailing 107 people an average of 3 emails (300+ total emails), before getting a good idea of what messaging and points of emphasis resonated (or at the very least got a response).
Out of those 300+ emails, I quickly learned what subject lines people responded to best, what email content they replied to most, and what stuff people blatantly seemed to ignore.
From there, once I started to get consistent email replies and feeling like I was weeding out people who were just kicking the tires and would never buy, I knew I could move to a more automated workflow that was fairly simple. It ended up looking like this:
It’s been a consistent 6% conversion rate from test drive signups to paying customers for just over a month as of writing this update. I still end up emailing with almost every person who purchases but overall it’s a way more automated system (and I truthfully don’t mind emailing with folks!)
Bonus: A little unforeseen bonus to the WAIM Test Drive is that it nearly doubled our email signups each month. That’ll come in handy when we do bi-annual WAIM Membership launches (more on that in the next update).
(You’ll notice the “total students” number is 446 and the difference between 412 and 466 is a bunch of spammers or WAIM members checking out the test drive.)
This was a pretty big decision to make because it drastically affects the ongoing MRR business model we’re creating with WAIM.
Looking at the data from our BuyOurFuture project (the previous version of a WAIM Membership which was sold as a pay-once-and-never-pay-again deal), I noticed our total churn for BuyOurFuture was crazy low: 4%.
Our total WAIM Membership churn was 30% (when we hit our 100th paying member, we also had our 30th member cancel; not a fun coincidence – woof.)
Losing 30 members is the same as losing $3,000 per month for us. That’s not sustainable considering we’ve only been gaining 20-30 new monthly members on average. Something had to change.
We have history on our side to test this hypothesis with WAIM. It’s why our BuyOurFuture project was priced as a “Lifetime” deal, meaning you pay us $2,000 and never pay us again but keep getting access to new things forever. For us, this lifetime pricing model also feels more unique and interesting. It helps us stand out from all the other business membership options.
I’d like to collect a few more months of data to see how this affects our overall churn. The switch from ongoing monthly payments to lifetime seems to be making our current paying members happy as well, so that’s an immediate win!
At first, I thought it was going to drastically blow this whole enough-thing up – haha. But, the more I thought about it, the more I think we’re still striving for the same 330 goal. It’s technically the same MRR goal, there’s just a difference in how long a member stays actively paying us.
If the first few months are any indication, our high monthly churn rate (15%) was going to make it quite an uphill battle to reach our enough number. In fact, in forecasting out the next 12 months, things weren’t looking great to reach our goal:
However, if we can reduce our churn back down to near where it was with our BuyOurFuture project (5%) and continue at the same monthly growth rate, we have a much more positive outlook for the next 12 months:
(This forecast doesn’t take into account losing MRR to folks who finish paying us, but that won’t happen for at least 18 months.)
One of the most important parts of running your own business is making changes and decisions that make you feel GOOD.
It gives our customers maximum lifetime value from us and doesn’t require them to think about how long they need to stay paying members. And from our side, it should drastically reduce our overall churn and increase our customer lifetime value.
Plus, it’s fun! As weird as it is to say this, having a selling point be that, “you’ll never pay us again after $2,000!” is something we genuinely like doing.
The past two months have moved both incredibly slowly and quickly at the same time.
Things have moved quickly: At the beginning of the year we found out there was a good chance we’d have to move in a few months (our landlord trying to sell their place). This was after we signed a 12-month lease to renew and stay put. We hate living in limbo so we decided to put our future in our own hands and find a new place to live. After weeks of hunting through Zillow listings, we found our new home, moved, decorated it, and are already enjoying the awesome new views!
Things have moved slowly: Poor Caroline is still dealing with some gnarly anxiety. We’ve been doing Neurofeedback treatments for almost two months and those are absolutely helping. There’s a pretty substantial difference from where she was two months ago and where she is today. However, she’s definitely not back to 100% or even close. Some days are pretty normal and others are pretty awful. She’s doing her best but it’s a struggle almost every day and is really tough on her.
The reason I share the personal side of things in these updates is that I know YOU deal with life too. You have big goals of your own and something derails you or gets in your way. It sucks. But alas, we all deal with it.
On the positive side of things, we’ve built WAIM in a way that Caroline doesn’t have to invest much time in it for it to stay afloat. She’s starting to do a little work here and there but it’s nowhere near what she was doing before.
On the negative side of things, it does end up feeling like I’m trying to manage all of our business stuff and still show up as a supportive husband. It’s definitely a balancing act each day/week and we’re both doing our best (and grateful we have an awesome community that supports us).
I realize this update has gotten pretty long and I’ve already gone back through and trimmed it a few times. Instead, I’ll just tell you that we’re really happy with how Build Without Burnout has turned out as a program and it seems to be helping folks already:
This is one of those updates where we’re really happy to see positive changes and growth toward our enough goal, but we’d trade it all just to have Caroline feel like her normal/happy/creative self again.
Perspective is a funny thing though. We’re trying our best to navigate through this rougher patch in our lives while also acknowledging it could be so much worse. If we didn’t have the amazing audience, customers, and opportunities that many people do not, these updates wouldn’t exist (it’s a privilege just to be able to write and share them).
Anyhoo, don’t want to sound all doom and gloom! We’re happy and mostly healthy, just taking each day as it comes.
As of July 3, 2019:
Monthly Recurring Revenue (MRR): $10,033
Total Paying WAIM Members: 106
Monthly Profit and loss:
Total WAIM MRR: $10,033
Total WAIM Fees (Stripe/PayPal): $433
Monthly Expenses in September: -$3,512
TOTAL PROFIT: $6,088
Quick hits of what we did this month:
Whenever I would read update posts like this I’d wonder why the creator of them would have consistent updates and then all the sudden there’d be a big gap. Well, here we are, falling into the same pattern.
But… there’s a reason: We’ve been testing and trying a lot of things. We’ve also been seeing some major improvements in Caroline’s health and that has been something we’ve cherished each day since the beginning of May.
It’s wonderful and fantastic that Caroline is feeling better but we don’t want to fall back into old habits and have her jump back into a workload that stresses her out.
I will say, while I’ve been able to toe the line around WAIM since January, it feels AMAZING that I get my partner in crime back. Not just for business stuff, either. We’ve been able to enjoy some simple life moments together…
This part of our update has me a bit bummed and confused. We saw some really solid traction when I first created our WAIM Test Drive (scroll up to the previous update if you missed what that was).
However, as time went on, the Test Drive’s conversion to paying memberships dwindled, dropped, and fell nearly flat.
I asked my buddy Paul why he thought our Test Drive may have stopped working:
I think he’s 100% right. Otherwise, I don’t know what to think? How could the WAIM Test Drive perform so well in the beginning and then convert almost no one after two months?
Now you may be thinking what I was: $12,400 is AWESOME, why the hell would we stop using the WAIM Test Drive? 🤔🤔🤔
Well, if we look further into the numbers…
As you can see, and as Paul hypothesized, the WAIM Test Drive was great at converting folks who were probably already on the fence, but not great at converting new folks. Sure, it may take more time for the new folks to convert, but there was another glaring statistic that stood out to me:
The Test Drive automated email workflow open rates, while not awful, are much lower than I’ve seen for any email funnel I’ve ever created before. To the point where it seems folks were interested, had a look at WAIM, lost interest, and then didn’t care about our emails at all.
NOTE: I’ve checked ~50 email subscribers from the Test Drive and after 30 days they completely stop opening our weekly newsletter emails.
Some people might argue this is just the name of the email marketing game, especially around trying to automate sales funnels, but that’s just not our cup of online-biz tea. We’re not interested in using tactics that are flash-in-the-pan. We want to build longer relationships with people who are highly engaged.
For that reason, we put the Test Drive on hold, for now, to focus on trying something new (more on that in a moment; see Make500 below).
We’ve been selling a version of the WAIM Membership, as mentioned many times in this post, since 2015. There’s a pretty typical sales cycle over the course of a launch window:
That’s pretty standard for us across the board. Except, NOT during our most recent May 10-day launch…
WHAAAAT???? Hahaha. I can’t even begin to tell you how weirded out we were by this launch. Nothing was that different from our previous launches. The emails were mostly the same. The calls to action were mostly the same. It. Was. Just. Bizarre.
My assumption as to why this was? We haven’t added enough new people to our email list since the last launch so we were only converting folks who needed a bit more nudging to join.
Because we charge $100 per month for our membership, spending $1,400 to only make $300 in the first month is a bit risky. Now, could it pay off? Sure. Our average lifetime value is $530 per WAIM member which would mean it’s almost break even.
My hope is that these three members stay on longer to improve that conversion spend because spending $1,400 to make $6,000 (if they paid in full) would be great! However… it’s gonna take a long time to see that come to fruition.
For us, our membership isn’t converting well enough on its own at the moment to think about paying for FB ads consistently (even simple retargeting ads).
And truthfully… We’re beginning to think the WAIM Membership possibly just does too much stuff. There are too many problems we can solve in the membership that we’re overwhelming people, therefore, not solving ANY problems (that’s no beuno!)
Which leads us to…
We’d like to create a consistent “marketing engine” that works on its own to lead people into the WAIM Membership based on just our online course teachings. Enter, our next experiment: Make500
The idea behind Make500 is to attract our core, ideal audience member:
Our goal with Make500 is to have that ideal audience member create a mini online course that they can sell and make $500 from.
If that hypothesis is true, as we’ve had it work for a few existing WAIM Members, then selling them on the value of a WAIM Membership after they complete Make500 should be a no-brainer.
As of writing this update we have a group of 20 beta testers going through Make500 and one person has already converted (hey, that’s neat!) We need a lot more data and I want to see if our organic traffic on our website will be the right fit for Make500.
Only one way to find out! More on Make500 in the next update.
It’s important that we take a step back and look at the big picture. We are seeing a trend in the right (overall direction) and it’s comforting to see our MRR growth curve continue to trend in the right direction:
That’s good stuff! It’s positive progress. And probably the most rewarding part of that chart isn’t the money, it’s messages we continue to see in our community, like these:
Sure, we’ve continued to have customers cancel (8.8% churn the past 3 months) but we’ve also added 32 new customers. And while it will continue to feel like a punch in the solar plexus (yes that’s how it’s spelled) that people are canceling, I’m beginning to come to terms with it and just accept it’s going to happen. Yeah, I know, it’s only taken about 10 months!
It can also be a bummer to get stuck in the weeds of conversions, testing, experimenting, but it’s less of a bummer when you step back and look at the OVERALL picture. When you realize things are going in the RIGHT direction… just maybe not as fast as you’d hoped (ugh, a metaphor for life #amiright??)
There’s no doubt we’re trying lots of things to grow our membership and our MRR. One important thing for us though, we have to continue to enjoy the process AND realize we’re just two people. So far, so good!
It can be easy to get bogged down with wanting to do a lot more but not being able to. Sure, we aren’t nearing our “enough” finish line just yet but we ARE 30% of the way to our goal. We ARE seeing incremental positive growth. We ARE hearing from our members that they really enjoy the value of the membership, the community, and all the products/services they have access to.
For now, we’re having gratitude for what we have and focusing on what we can accomplish in the next few months while also enjoying the summer and Caroline’s improved health!
As of October 20, 2021:
Monthly Recurring Revenue (MRR): $35,400
Total Paying WAIM Members: 278
Monthly Profit and loss:
Total WAIM MRR: $35,400
Average Monthly Fees (Stripe/PayPal): -$1,000
Average Monthly Expenses: -$4,000
Average Monthly Affiliate Fees: -$9,000
AVERAGE MONTHLY PROFIT: $21,400
Quick hits of what we did
First of all, we just want to apologize for anyone who was on the edge of their seat back in 2019 and then thought we fell off the face of the Earth 🌍. We didn’t intentionally stop updating this post, but we got laser-focused on what was most important to grow our biz (and some things had to be cut… like updating this post).
Second, we ALSO really dislike when you’re following something closely, consuming all the juicy details along the way, and then
Okay, that’s us trying to make amends. Cool? Hopefully, cool. Also, as a reminder, this is us:

Where we last left off (July 2019), WAIM was still a lifetime membership charging customers $100/month ($2,000 total) for a package of courses, workshops, access to a Slack channel, and an included Teachery account. Through multiple conversations with customers who canceled WAIM and existing paying customers (plus some ah-ha moments on our daily walks 🚶🚶♀️) we discovered that there was nothing ongoing that would keep someone a paying customer.
Now, that may seem like an obvious thing to you when you hear we were trying to build a membership community but we truly believed all the existing “stuff” would be compelling enough for our customers – and it was – for a small handful of folks.
How could we keep members engaged and receiving value month after month? This was the question we needed to answer.
We also knew that in order to market our offer effectively, we needed to solve a clear problem. Digging into our core audience’s pain points, we realized that most business owners are overwhelmed with all the various aspects of improving an online business: content, social media, sales strategies, website optimization, building an email list… it’s all so much.
To help provide a solution for that pain point, and to keep our members engaged, we decided to commit to a live monthly group coaching session where we’d teach on ONE specific topic each month.
(This was also roughly the time when Caroline’s anxiety started to improve and her work capacity increased. That played a big part in this pivot as well.)
We felt good about shifting our offer in this direction, but there was one more big change we wanted to make.
Because we are experienced experimenters 🧪 we knew we wanted to test an MVP version of monthly live coaching. We also thought we might try a smaller offer in addition to our standard $2,000 lifetime membership. That’s when we decided on a 6-month group coaching package, priced at $100 per month for six months (total of $600).
We chose that price and duration for a few reasons:
Even though our MRR chart doesn’t look crazy different, it was arguably the biggest (non-financial) inflection point on our journey. It allowed us to prove a concept that was sustainable for us and that our customers raved about. It was the moment we finally had “offer-market fit” but we didn’t see the financial impact of that for months to come.

*Sometimes the biggest inflection points in businesses don’t come with immediate financial returns. Sometimes the biggest inflection points are pivots, decisions to quit, or simply embracing experimentation as a mindset and trying lots of new things.
From the Summer 2019 until the Spring 2020, we focused heavily on delivering our live monthly coaching and listening to feedback from our members. While our MRR did grow during this time, our focus was more on making sure our new customers were happy and making sure we enjoyed the monthly coaching.
And… they did enjoy it! 👍👍

Our Slack community seemed to be more vibrant. There seemed to be more conversations happening, more member participation, and it should be no surprise that when you give people something to focus on each month, they’ll also have something to talk about each month!
We also discovered we THOROUGHLY enjoyed live coaching. It brought us both into our unique zones of genius.
For Caroline 👩🏻🦰: Monthly live coaching really highlighted her love of teaching. Creating online courses for years prior was the perfect primer for creating our monthly coaching curriculums.
For Jason 👨🏻🦲: In a previous life, I (the person writing this update post to you) hosted a 1-hour DAILY live video show for nearly five years. Anything you do consistently for five years has to be something you enjoy, and interacting live with people through video really gets my creative/silly juices flowing!
Here’s a look at the Coaching Hub we created for our customers where they could access the next session, previous session replay pages, and specific coaching Slack channel:
And here’s a look at the suuuuper fancy live coaching tech setup. We take great pride in quality and because Zoom (our live video tool of choice) compresses the crap out of video, we also recorded our sessions using a Sony A6400 camera, Keynote’s built-in presentation recording, and everything gets edited together the afternoon after the live coaching:
As of writing this update (October 2021) we’ve hosted 25 live coaching sessions, meaning we’ve been doing monthly coaching for two years already! WOW! 😱🤩🤪 The covid time warps are real, y’all. Coaching session topics include:
🦠 Covid-19 Note: We didn’t want to just gloss over covid because the implications of it were/are tremendous. We were extremely fortunate that a global pandemic didn’t affect our business in the way it did thousands of others. We did have a handful of customer cancelations, but we know we got very lucky existing in a remote, internet-based industry that allowed our business to continue to grow during 2020. Still, family members coming down with COVID and the emotional turmoil that brought, not to mention weathering that kind of uncertainty with Caroline’s anxiety, it was a challenge in a multitude of ways. Ultimately we were actually grateful to be a source of community for people during this time, and it fueled us in a deeper way to offer people creative solutions for bolstering their income whether through growing their side hustles or taking their previously offline skills now online.
It was at this point on our journey, hitting the halfway mark of our ENOUGH goal 🎯, we felt in control of our business.
We realized monthly live coaching was the linchpin to WAIM and our Spring 2020 enrollment was the last time we offered the 6-month coaching package. We knew we were going to do live coaching moving forward, we knew our customers liked it, and we wanted to position everything around coaching. We also felt we had enough awareness around our program at this point that we no longer needed the smaller 6-month offer as a “test it out” kind of offer.
The WAIM Sales Page you see now is the one we put together in the Fall of 2020. This sales page is the culmination of everything we learned about positioning, copywriting, and ensuring the right customers know we are the right coaching program for them. Also, random fun fact, I believe it was our sixth sales page we’d created for WAIM since 2018.
By Fall 2020, we had the following assets for our customers:
Our members really appreciated that we gave them one thing to focus on each month with live coaching but they were looking for some additional guidance through our assets. When we took a step back and looked at our WAIM Library and the WAIM Coaching Hub, it’s no wonder they didn’t know what to dive into next. It was information overload with no compass to guide them.
The more we talked about it, the more we knew we needed a better container that could bring all our coaching sessions, workshops, courses, etc, into ONE place and LEAD our customers on a journey to improve their businesses.
Again, this goes back to that ultimate PROBLEM we were trying to solve for people: give them ONE thing to focus on each month. But when everyone’s business is different, how can you lead someone to the right next step for them? You create a sequence that they can follow so the next right step always becomes clear.
Our initial brainstorming session about guiding our customers revealed five pillars of focus:
These five pillars became the initial “content buckets” all our other existing content would sit within. We eventually ended up creating a flow chart that touched on every part of that roadmap using every asset we’d already created. The purpose of the flow chart would be to ask questions and lead someone to the next right step based on what they’d already tried in their business:
This flow chart coincides with the cornerstone product we created: The Un-Boring Business Roadmap. The roadmap is simply a course every member gets access to in their Teachery account. The five pillars I just mentioned are “Lessons” in the course and all our assets are “Sublessons” within the course (all the yellow items in the flow chart above).
As the roadmap started to come together we got really excited about it! Not only was it a new “thing” to offer as a carrot 🥕 during our Fall 2020 launch period, but it also solved an ongoing problem for our customers.
One of the other things we kept getting asked from our existing members was if we were ever considering creating an affiliate program for WAIM. The answer was YES! but we didn’t want to do this until we felt really confident that WAIM Unlimited was solving enough of a problem and creating a great experience that would keep people on as paying customers. (There’s no point in pouring more customers into a business with a high churn rate!)
There was an interesting moment as we recapped our Fall 2020 launch with our members at the end of our October 2020 live coaching call. We shared a slide that compared our Spring 2020 launch (71 new customers for the 6-month coaching offer) to our October 2020 launch (51 new customers for our WAIM Unlimited offer):
While 51 is less than 71, moving to WAIM Unlimited and not selling a $600 (6-month) coaching package was the right long-term move for our monthly revenue.
The big takeaway for us was that 50 new members bi-annually would be a great amount of new customers. While our immediate MRR didn’t jump, it extended the overall runway of our MRR so we knew our next launch would be the time we’d see a sizable jump!
And with that next launch, that’s where you can see one of our biggest revenue jumps since we started in 2018:
As we mentioned earlier, Covid-19 hit our family as well, but thankfully not as hard as it did many other people. Caroline’s dad was hospitalized with COVID for five weeks to start 2021 and it was really tough 😢. We are so grateful he was able to get excellent care and when he finally left the hospital in mid-February, we let out a huge sigh of relief.
After recovering from the mental rollercoaster the beginning of 2021 put us through (not to mention the abhorrent attack on the U.S. Capitol building by U.S. citizens 😩), we were ready for a bit more “normalcy” and to focus on work.
We did an evaluation of the state of WAIM leading up to our Spring Enrollment period:
✅ WAIM was being sold as a $2,000 (un-boring) coaching program.
✅ We had the Un-Boring Business Roadmap to guide members through all our courses, content, coaching sessions, etc.
✅ We figured out a great cadence of launch content (emails + posts on IG + mentions on our podcast).
✅ We built a simple affiliate program and had a product our customers were happy to promote during our launches.
✅ We found a consistent email and podcasting strategy and stuck with it.
March 2021 rolled around and we queued up our nine sales emails. We posted a handful of times on IG for two weeks. This was the first launch of WAIM that truly felt in our control.
The numbers didn’t lie either!
It took us two years to go from $0 to $13,000 in MRR for WAIM. During our two-week Spring 2021 enrollment period we added nearly that exact amount of MRR! That’s… AMAZING. 😍❤️🙌
A huge part of that success was owed to our existing WAIM members who promoted our launch as affiliates. This was our second launch with affiliates but we put a bit more effort into it after learning from the first go-round.

Yep, 74% of our Spring 2021 new members came from affiliates. Of the $13,100 in MRR we gained during the launch, $3,100 of that would be paid to our affiliates. We like to think of affiliate payouts as a way we can “advertise” WAIM, but instead of giving our advertising dollars to a big company (ahem, FB), we can put that money directly in our members’ pockets!
Leading up to this Spring 2021 launch we wanted to experiment 🧑🔬👨🔬 with IG Reels. Instagram seemed to be pushing Reels pretty hard and we’d not put much attention or effort into them at all (honestly, we don’t put that much effort/attention into social media at all). But hey, we love trying new things so let’s do it!
We ended up creating 16 Reels leading up to and during our 2-week enrollment period. Caroline gets ALLLL the credit for our IG content and I was simply available as a prop, a dancing idiot, or the person who sets up the tripod and presses the record 🔴 button on the iPhone 😂😂.
You *MIGHT* notice one of those Reels’ view count is not like the others… With no explanation whatsoever, this particular Reel struck a cord and had its own viral moment (amassing 220,000+ views in 72 hours).
While having a Reel go viral might seem like the dream scenario during a launch, aside from the 1,500ish new followers to our @wanderingaimfully account, IG still ranks incredibly low on the “how did you hear about WAIM” question in our post-purchase survey:
So, sure, it’s nice to see a Reel go viral and it’s fun to get new followers… but… it truly didn’t impact our sales. And for reference, during the Fall 2020 Enrollment (the previous launch), 8% of buyers said they heard about us through Instagram, so it technically went DOWN this launch 📉😅.
After our Spring 2021 enrollment, we took the majority of the summer to rest, recharge, and to soak in the Southern California sunshine.
For the first time in… welp… our entire lives as online biz owners who always send weekly emails, we took two FULL months off sending email newsletters. We also took a break from YouTube, IG, and recording podcast episodes during those two months. When we say we took a nice summer sabbatical, we took a nice summer sabbatical!
(Yes, that is me lounging in our tiny “stock tank” pool. You aren’t going to be doing any backflips into that pool but it’s the perfect place to take a dip and cool off 😎).
Alright, Summer of 2021 came to a close and we started gearing up for our Fall enrollment period. As you may have gleaned from the previous paragraphs, we really felt like we’d hit our stride with WAIM as a business. The following things were definitely working in our favor:
Once you figure out a plan that works (through months/years of experimentation), you can stick to it and just plug and play the necessary puzzle pieces 🧩.
Our Fall 2021 enrollment went off without a hitch. We followed the exact same plan as our Spring enrollment and barely made any changes. The only real change was we recorded seven YouTube videos and shared them weekly leading up to the launch. This was another experiment 🧪 we wanted to try and it didn’t move the needle much at all (nor did we really expect it to). We always love trying things, though!
As the 2-week Fall sales period came to a close, a gigantic milestone on the Journey to Enough had been hit:
I could type a bunch of words to capture exactly how we felt the moment we realized we hit our enough number but thankfully we had the foresight to flip on the old iPhone selfie cam and record the moment in real-time to share…
What you might notice in that video is that we’re not jumping for joy. Is that… bad? There’s definitely a tinge of guilt in sharing with you that hitting our enough goal didn’t result in an epic dance party. But the reason we’re it may seem like just another day to us is not that we don’t celebrate the journey or appreciate this hard-earned milestone; it’s that while this journey STARTED with this “enough” number in mind, along the way it became less about the outcome and more about the process itself. We finally have a business that is profitable and fuels a life we love, that serves our customers’ needs and provides value, and that can continue on sustainably. The MRR is just an amazing byproduct.
We think this is actually evidence that the enough philosophy has done its job because when you finally reach that mountaintop you defined, you’re not thirsting to go reach the next big one. You’re content in what you’ve built and can continue to engage in a process you enjoy to see where it leads you.
(Nonetheless, when we got back to California, we had a proper dance party to celebrate! 🎉🎉)
Great, the celebratory dance has been done ☑️. So, how did our Fall 2021 launch break down?

It’s a bit surreal to write this final update to this post. We are truly grateful for the business and the community we’ve been able to build. Every day we express gratitude for WAIM and the leap we took together back in 2018 to start it.
As you’ve read (or skimmed 🙈🤣), our journey was not a straight path to success. We had challenges, setbacks and moments of doubt at so many places along the way.
However, as you read this and (hopefully) take inspiration to apply to your own business and circumstance, it’s important for us to acknowledge there’s a lot of inherent privileges we have that many people do not. As white, cis, heterosexual people with a lower-middle-class upbringing, it’s simply a fact that we had less hurdles to face in our pursuit of this freedom-filled business than most. We see that more clearly now than ever.
As mentioned at the beginning of this post, we have been and will continue to steadily increase our annual wealth redistribution (previously what we referred to as “charitable donation”). As we reach a place of financial privilege and security, we want to make sure we are helping contribute to solutions that facilitate that same opportunity to those who are systemically excluded from it.
Because you’re a savvy reader and have paid attention closely, you understand that our “lifetime” revenue model means our monthly recurring revenue has a certain shelf-life, so to speak. After a customer pays $2,000, we make $0 in revenue from them moving forward so we will have to replace their revenue at some point.
The way we’re thinking about things moving forward is fairly simple:
We don’t plan on writing any updates about this journey after this one and hope you’ve enjoyed this exhaustive and thorough look into WAIM 👋.
Thanks for reading and we’ll see you around! 👩🏻🦰👨🏻🦲🤗
Note: Some of the services below have our affiliate links in which we make a tiny commission if you sign up. You can read our full Tools We Use list here.
Flywheel – We’re huge fans of Flywheel’s WordPress hosting! I joined them really early on with my previous JasonDoesStuff site and have loved every minute of paying them money. For just $15/month you get an intuitive dashboard, free SSL, fantastic customer service, and included hands-on migration from your existing WP host.
Restrict Content Pro (RCP) – We were completely new to RCP when we started building WAIM but we heard great things about it. RCP has lived up to the hype and is incredibly powerful if you’re trying to run a membership community using a WordPress website. The features are great, the help documentation is solid, and customer service has also been top notch.
Affiliate WP – Our members asked for it and we finally decided to offer an affiliate program for our existing members to earn a commission for bringing in new members during our bi-annual launch periods. Affiliate WP plugs in perfectly with Restrict Content Pro! We really appreciated how simple and fast it was to get an affiliate program up and going.
ConvertKit – During the first few years of WAIM we used an email provider called Drip but have since made the move BACK to ConvertKit (where we were in 2015-2016). Drip shifted their customer focus and ConvertKit added a ton of great features for creators like us!
Vimeo Pro – We previously hosted all our videos with Wistia but their bandwidth pricing started to put a hurtin’ on our monthly budget for WAIM. We made the switch (thanks Kade!) to Vimeo Business and haven’t looked back since. We really enjoy the Vimeo experience and recommend it highly if you need private videos with custom branding.
Interact Quizzes – We mentioned in our final update that our email list grew by 400% when we started using a quiz. Interact is the quiz provider we chose and we’ve been EXTREMELY happy with them. You can see our quiz in action by clicking here.
Notion – At this point, you are probably very familiar with Notion? If not, it is a game-changer! We use Notion for errrrrrrverthang in WAIM. It’s how we manage our member payments, how we organize all our content, how we plan any project we’re working on, and we even track our “Classic Movie Nights” in a Notion database. We truly love it and couldn’t live without it.
Slack – With over 800 total WAIM Members, we wanted our own private place to hang out and chat, free from distractions (we’re looking at you FB Groups). We use the free Slack plan and cherish all the amazing features we get. If you run a community or just want a way to chat with friends/co-workers, Slack is a must-use.
Baremetrics – The most beautiful way to keep track of our monthly recurring revenue and overall financial growth of WAIM. Baremetrics takes minutes to set up and is completely automated if you use Stripe (we do have to input our PayPal members manually).
Hope one of those tools can help you in your biz!
A few years ago my wife and I found ourselves overwhelmed with debt. How much debt? $124,000 spread across six credit cards, a car loan, and student loans. We could never have imagined being debt free at that time.
This article shares our debt story, but more importantly shares our debt payoff plan: the exact steps we used (and that you can use) to become 100% debt free in just 15 months!
Before we dive in, I want to be absolutely clear that we didn’t get into overwhelming debt overnight and we didn’t get out of our debt overnight.
Our debt didn’t come from buying extravagant things. The majority of our debt came from a business I ran from 2009-2013. I got behind on the monthly operational costs, things like employee salaries, design and development expenses, advertising and marketing, and countless products and services that kept my business running. Then we had my wife’s business debt, her student loans, and our car loan.
These were our specific debts and where they came from:
I want to point something out before I move a step further, and my guess is you can relate to what I’m about to say.
You can also watch the video version of our debt-payoff plan:
Did you know the average credit card debt per U.S. adult, excluding zero-balance cards and store cards is $4,878*?
How about the fact that 26% of small business owners carry a balance of nearly $10,000 on their business credit cards*?
Or did you know that more than 35% of Americans are seriously concerned about being able to meet essential financial obligations such as their mortgage, loans, credit card, or bill payments*?
Some of us are riddled with debt, stuck in its invisible grasp with no sight of escape. Some of us just have school loans, which seem harmless because of low fees and payments, so we ignore the soul-sucking and bank-account-syphoning elephant in the room. Some of us are able to use debt to our advantage to escape a bad month of business or get through hard times. But debt is dangerous and it needs to be dealt with head-on.
Let us help you attack your debt, just as we attacked and vanquished ours!
Around 2013 I realized our total debt was over $120,000. That was the moment when I knew something had to change.
Unfortunately, that change came with the tough decision of closing my business’s doors. That meant letting people go, cutting as many expenses as possible, and accepting the fact that my business was no longer profitable and was failing.
I hope, for your sake, that $120,000 is not your number. I hope it’s a drastically lower number. But if you do have more debt than we did, don’t be ashamed of it any longer. It’s just a number.
Make today the day you announce you aren’t getting any further into debt. Draw your line in the sand right now.
It would have been easy to let the feelings of shame and embarrassment continue to control how we felt about our debt. We could’ve given in to those feelings as we’d been doing and as a lot of people do, but instead we decided to do something different.
Bear with me, as I know this is going to sound weird, but we started to think of becoming debt free like playing the original Donkey Kong video game:
This Donkey Kong metaphor may sound completely bizarre to you, but it really helped us shift how we thought about our debt. It went from a dark cloud that loomed over our heads, to a silly game we could try to beat. With each ladder we climbed and every barrel we jumped over, we’d be getting that much closer to rescuing the princess (AKA gaining financial freedom).
Whether you want to buy into our Donkey Kong metaphor or not, maybe there’s a way you can reframe how you think about your debt? The most important thing at this point is to draw your line in the sand and to tell yourself: I WILL GET OUT OF MY DEBT!
TIP: A great thing to help draw your line in the sand is to have someone hide your credit cards so you can’t have access to them. Or just cut them up. Start using a debit card or cash only.
We’re a society driven by consumerism.
Turn on any TV. Open any magazine. Browse any website. Scroll through any feed on your phone. There’s a new gadget or clothing company begging you to spend money you don’t have. Today is the day you tell yourself you don’t need to buy any more stuff.
“I don’t need to buy XYZ thing. I want it, but I don’t need it.”
How many things have you purchased with your credit card(s) in the past year that you can actually name off the top of your head?
If you can’t remember what you spent your last couple thousand dollars on, it wasn’t that important and you didn’t actually need to buy it.
What’s more important in your life: Owning a couple new material goods, or NOT being stressed out over your current financial situation?
Commercial after commercial tells us that the credit card companies just want to help us! They want to give us nice low rates (which most of us can’t actually qualify for) and they want to reward our spending by giving us awesome perks (redeem those double points!).
Except, when you’re in debt, the last thing you should be thinking about is credit card points. One of the important mindset shifts in becoming debt free is greatly reducing your spending. I’ll talk more about reducing spending in a moment, but credit card companies are great at convincing us that “cash back” feels like we’re somehow saving money. Or that “airlines miles” will help you travel for free. If you’re in debt, getting minuscule amounts of cash back or accruing airline miles are thoughts you need to put on hold.
At one point my wife and I had 12 active credit cards and the majority of them were opened because of the so-called “rewards” they offered. Here are a couple of examples, along with the rewards we never actually enjoyed:
Best Buy Rewards Card – A simple VISA card that helped us purchase electronic goodies. Except, when we bought them with Best Buy’s friendly payment plans, we didn’t take into account we’d up spending 20-30% more on the items we purchased because we could only ever afford to make the minimum monthly payments.
Southwest Airlines Card – I remember the day I signed up for this card and thought I’d grab the reward offer of a free companion pass for Southwest flights. Within a month I’d met the qualifying spend of $3,500 on the card, except, I didn’t have the money to pay it off. You don’t get the free companion pass if you don’t pay off required spend. Not only did I not get a stupid free companion pass, I now had $3,500 of debt that probably didn’t need to exist. (Also, FWIW, I can count on one hand the number of Southwest flights I’ve taken in the past decade, we never fly with them.)
CitiBank Diamond Preferred Card – This was a card I signed up for because it would 2x or 3x your points depending on what you purchased. It took me six months to realize I could only ever use those points for stuff I didn’t need (like a blender, or headphones, or other consumer goods that I already owned or absolutely didn’t need).
I hope these examples help you take a look at the cards you currently have in your wallet/purse. You may think these credit card companies are trying to help you, but they’re not. These companies have very well crafted systems in place to keep us all in debt.
TIP: Stop using credit card points cards until you’re completely debt free. When you’re debt free, start to identify one or two credit cards that offer rewards you might actually use.
The un-sexy secret to getting out of debt is exactly the headline you just read: Spend less money or earn more money.
Sure, there’s a lot more to becoming debt free (hence the length of this article), but along with acknowledging your debt and avoiding consumerism, this is the next mindset shift that will help you get rid of debt.
I could write an entire article on why buying a home is a terrible financial investment for the majority of us. Instead, I’ll let the economic crash of 2008 do the talking for me. I would, however, like to explain how renting a home (AKA “throwing money away”) was incredibly helpful in our journey to financial freedom.
When you have a home with a mortgage, as we did for 8 years, you do NOT have stable expenses. In fact, most homes are a ticking financial time bomb.
What do I mean by that? Oh, how about when your air conditioner breaks and you have to spend $8,000 to get it replaced? Or how about when you wake up one morning to an inch of water in your living room, only to find out you had a “slab leak” which still cost you $2,000 (after insurance!)? Or how about the $20,000 “invested” in redoing the kitchen and bathroom which was never actually recouped. Not to mention every stupid little thing that pops up and needs to be fixed (and paid for) when you own your own home.
Deep breath Jason, deep breath.
When my wife and I moved from Florida to California and chose to become renters, we knew one very important thing: Renting gave us the piece of mind that we’d incur $0 in surprise costs when it came to our home.
As renters, we’d never have to worry about an $8,000 air conditioning system. We’d never have to worry about little costly odds and ends. We would pay our rent every month and that was it. If something went wrong, it was on our landlord’s dime. Every dollar we used to have to spend to cover unexpecting home costs could now go toward aggressively paying off our debt.
Renting can be the best thing for people who are in debt. It’s a completely predictable expense every month, and you are guaranteed NOT to lose money in the long run.
A home you buy? Not an investment to be made when you’re trying to get out of debt. Heck, we’re years removed from being in debt and we still (proudly) rent our home.
I want to share a more personal example of spending less money: For me, that was a 15-year passion of owning nice cars.
I love cars. LOVE them. They’re easily the biggest money-pit I’ve had besides my business. Except, unlike my business, there is no potential ROI (return on investment) for a car. Sure, a 1950 Ferrari Dino is a great investment, but let’s be realistic here, you and I are not collecting Ferraris.
Aside from our mortgage and food, my monthly car payment was always our highest household expense. Over the years I had car payments ranging from $500 per month to as high as $1,200 per month—the latter being the time when I needed to own a Porsche Cayenne Turbo as a 25-year-old (dumb, dumb, dumb). Not to mention all the extra hidden costs of cars like gas, insurance, maintenance, etc.
When we decided to attack our debt, I knew my “fun car” hobby had to take a back seat (get it? It’s a car pun folks!). My wife and I talked about this decision together and I made the commitment to our get-out-of-debt plan that we’d purchase an affordable car and be more responsible when it came to spending money on depreciating assets (cars). We ended up leasing an extremely practical Volkswagen SUV, a car that would be very low in maintenance costs, yet not feel like we were driving a 1982 Ford Taurus.
I’d be lying to you if I said I loved driving that VW. Truthfully, I loathed it. It wasn’t a bad car by any means, but it was quite the departure from the BMW M5, BMW M3, Porsche Cayenne, Infiniti G35, etc, I was used to driving. But I just had to keep asking myself: “Do I want to feel cool driving around in a nice car, or do I want to save the financial princess and stop having a looming cloud of debt over my head?”
Think of spending less as short term pain, for long term gain.
I really hope this point settles in with you. Your current TV, couch, bed, car, etc, are all enough right now. They are good enough and will do the job you need them to do until you become debt free. If you can commit to making short-term sacrifices and not focus on upgrading anything in your life, you can make huge dents in paying off your debt right away.
You are spending less now so you regain control of your finances. It will be uncomfortable to change your lifestyle and remove lavish things from your life, but I can tell you from firsthand experience: the feeling you get from paying off all your debt is a lasting positive feeling that greatly outweighs the short-term blips in happiness you get from buying stuff.
Now that I’ve gone over the spending less part, let’s talk about earning more money with two specific examples.
Let me start off by saying that I realize earning more money is not easy. If you don’t own your own business and you work at a conventional 9-5 job (for someone else), it can be difficult to think about earning more money. I do want to tackle both scenarios though, as I believe it’s possible to earn more money whether you work for yourself or you work for someone else.
I’d like you to meet my wife Caroline, she’ll be taking over the keyboard here for a moment to share her story of earning more with her business:
Hi y’all! Caroline here, Jason’s better half (obviously!)
When I was running my own branding design company in 2014 I had a stunning realization: Quite simply, I wasn’t making enough money.
I think this problem can take different forms for different businesses – not enough clients/customers, prices too low, terrible margins, etc. In my case, I was taking on far too many small projects for far too little money. $100 here for a hand-lettering project, $200 here for a small graphic design job, giving deals to friends and not being more vocal about the real amount of time a job would take. Then, when I had bigger branding design projects, I was working way more hours than I was charging my clients. Something had to change.
Jason and I sat down and starting talking about how I was running my business and where we might be able to make improvements (you know, make more money!) As we started talking it became clear that with any service-based business (AKA freelance), time truly is money. If it took me two hours to finish a job that could have taken me one hour, I just lost an opportunity for additional revenue. And if I had a bigger job that I only charged the client for 40 hours of work, but it took me 80 hours, I just missed out on a ton of revenue.
To give you an idea of just how much money I was losing out on, after implementing a simple time-blocking exercise (which I’ll explain in a moment) I was able to TRIPLE my revenue! Not only was I able to earn more money, I gained more time back because I became extremely diligent with how I was spending it on a day-to-day basis.
What is time-blocking and how did it help me triple my revenue?
Jason and I looked at a normal work-week for my branding design business and figured out a few simple things:
1. I did my best work between 11 am – 4 pm each day (5 hours of work per day)
2. Working Monday – Friday, I had 25 billable hours
3. Over the course of 4 weeks, working at $75/hour, I should be making $7,500 per month (25 hours a week x 4 weeks = 100 hours x $75 = $7500)
Seeing that $7,500 was defeating and empowering at the same time. I certainly wasn’t making $7,500 a month (I was lucky to be making $2,000 per month), but seeing how just 5 hours of focused work per day could generate so much more revenue for my business was incredibly motivating.
From that meeting with Jason, I started to block off time on my Google Calendar with client work. Whether it was a tiny 1-hour project, or a bigger 80-hour project, all of the working hours I committed to would go on my calendar and I would do my darndest to ruthlessly stick to the time I’d estimated. This time-blocking system gave me clarity in my work days and was a great way to understand how much my time was worth.
As I mentioned earlier, getting a grip on my hours, estimating my time better, and working during specific time blocks helped me triple my revenue in just a few short months. If you’re a freelancer (or you work for yourself), time is money and you should definitely keep track of it.
You thought that Caroline might be passing the writing-baton back to me, but she has another story to share with you about earning more money. This example specifically applies to you if you work a full-time job and don’t think you can earn more money.
It’s Caroline again, I’m back on the keyboard!
If you would have told me that I could make an additional $3,000 per month in revenue with a project I did on the side, I wouldn’t have believed you. If you read the last few paragraphs then you know I was doing branding design as my full-time job. Now, I wasn’t working for someone else in a 9-5 capacity, but the story I’m about to share happened in my “off work” hours.
Whenever I wanted a break from my client work, I would open up a sketchbook and start doodling. I didn’t consider myself an artist, but I enjoyed filling blank pages with drawings and hand-lettering. For months I filled sketchbook after sketchbook, not at all thinking I was honing a skill that would lead to earning more money, I simply enjoyed the creative outlet.
I started sharing some of my hand-lettering creations on my Instagram account and people started asking where I learned how to do hand-lettering. I responded in truth, I hadn’t really learned it anywhere, I just started doing it in my spare time. When enough people asked me about my hand-lettering, I had the spark of an idea: I should write a blog post that explains the basics (that I’d learned) of hand-lettering. Just a really simple guide if someone wanted to go on a hand-lettering adventure of their own.
That blog post started to get a little bit of traffic. Then it started to get shared on Instagram and Pinterest. Before I knew it, hundreds of people were reading my introduction to hand-lettering post and I saw an opportunity. I added an email capture to the blog post that asked people to enter their email if they’d be interested in an online course about hand-lettering (I’d never made an online course, but Jason had, and it seemed like something I could create if there was interest).
After a month I had over 500 email subscribers waiting for me to create a beginner’s hand-lettering online course! I hunkered down one weekend and created my first online course, without grand expectations about how it would sell. I worked on the sales page for the course and some other odds and ends in my non-working hours, and a few weeks later I launched the course. I was happy to make a few hundred bucks from the small email list and decided to change the callout on my blog post from “sign up to my email list” to “purchase my beginner’s course to hand-lettering.”
All of the sudden I was waking up to course sales. Then the traffic to the post would increase and I’d see more sales. Day after day, week after week, month after month, the sales steadily increased and I’d created my first passive income source. In the first two months that hand-lettering course generated over $7,000 in additional revenue I never saw coming and over $82,000 in total revenue!
The best part about the extra money I earned was that it happened on the side of everything else I was doing. It didn’t take an extraordinary amount of effort or time, I just saw an opportunity to create something and there was a demand for a quality hand- lettering resource for beginners.
I share this with you because I want you to realize what is possible. I want you to feel the way I felt when I made my first online course in my spare time and it started making passive income.
There are so many opportunities waiting to be had out there. You just have to find the drive and the commitment to make them happen.
Hopefully, after reading those two stories from Caroline your wheels are turning on how you might be able to earn a bit more money. And maybe after reading how we starting renting our home and I gave up a passion for cars, you’re already thinking about ways you can cut back on larger expenses you don’t need (for the time being, so you can become debt free!)
TIP: Grab a notebook and jot down a couple ideas of how you might be able to make more money right now: Is it using time blocking? Or creating a small product in your spare time that you’re interested in? Also, write down larger expenses that you may be able to cut back on.
Have you ever logged into your online banking or your credit card company, only to realize it’s kind of a pain in the ass to figure out how much money you’re actually spending? Sure, you can see your expenses in a vertical list with a total balance (usually always decreasing, ugh!), but banks and credit card companies don’t try to help you see where you can save money or cut costs.
It’s time for you to take control of all your expenses, and get a firm grip on every dollar you spend and make.
There’s a simple exercise that my wife and I did that opened up our eyes to our spending: We exported the last three months of activity on our bank accounts and credit cards, put them in ONE spreadsheet, and did our best to organize them by spending category (separated by month).
The silly thing about the name ETAC, if you say it out loud it kind of sounds like you’re saying attack. Which is neat, because you want to be attacking your debt!
Anyhoo, here are the simple steps for the ETAC exercise (video walk-through below):
📊 Click here to use the ETAC spreadsheet.
We encourage you to save yourself time and use our example Expense Tracking and Categorization spreadsheet with the categories we use to organize our expenses. If you’re creating your own spreadsheet, here are the categories we use and recommend:
The reason these categories are so important is two-fold:
1. You want to compare the category month over month and see if there are any big spikes and what your current monthly average spend per category is (this is how you can find where to spend less).
2. Later on, we’ll show you how to create an ongoing monthly budget for these categories, so you can be a wizard at tracking exactly where your money goes and have ZERO financial surprises (you know, like barrels thrown by a digital monkey).
I cannot stress the importance of the Expense Tracking and Categorization (ETAC) exercise enough! Even if you think you have a good idea of what you spend, I 10000% guarantee listing out and organizing all your expenses will surprise you.
NOTE: If you have spouse or family member, this is a great person to do this exercise with. You’ll probably be embarrassed to show them your expenses—but you know what—that’s a huge red flag that you NEED to show someone your finances!
When my wife and I organized our expenses for the first time, a few items within categories of spending jumped out as potential places to save money (and put towards our debt).
We were paying $260/month for our “family” cell phone plan. We’d had the same (unlimited) plan for more than two years and I had a hunch there was a better plan available. I went into an AT&T store (gasp! I know!) and asked them if they had a better option based on our actual phone usage. Come to find out, we were only using around 8GB of total data and didn’t need the costly unlimited plan. We switched to a $140/month plan and netted $1,440 in annual savings.
At the time of doing our first ETAC exercise, we were paying $185/month for all bizallion cable channels (that we only watched a small handful of). Back in 2014 cutting cable wasn’t as prevalent, so I didn’t think about that as an option, but I did think maybe I could call the cable company and simply ask for a better plan since I had been a loyal customer for years. I navigated my way through the painful customer support phone tree and was able to reduce our bill to $135/month, saving us $600 per year.
Drinks with friends, seeing movies (and getting popcorn), two Netflix subscriptions in one house, and a bunch of other stuff quickly filled this spending category without us even noticing. We decided we’d set some boundaries for our entertainment and hopefully save money. We allowed ourselves to see two movies (in the theater) per month and have two nights per month to have drinks with friends. Setting these boundaries saved us $150 per month or $1,800 per year. Remember, Short term pain for long term gain!
We were spending $2,000 per month on food ($1,400 was eating out). For two people that is a lot of money each month! However, neither of us love to cook and because we work from home, going out to eat is one of the nice breaks from our day-to-day routine. That being said, we challenged ourselves to cut back by $500 and only spend $1,500 per month going forward (this included eating out and groceries). That $500 added up quickly, saving us $6,000 (!!) that we could put towards our debt in one year!
Just by reassessing a few categories of our spending we were able to find nearly $10,000 we could apply to our debt!
Do a little bit of cutting back in the short term and you’ll find hidden money you can apply to pay down your debt. You’ll be amazed at how living frugally for a short time can help get you out of debt exponentially quicker.
TIP: Don’t waste any time, do the ETAC exercise today and categorize all your spending for the past three months. Where can you find hidden money?
The one thing that stood out to us, and that would become critical to our success in our war on debt, was building a better income flow.
If you’re anything like we were a few years ago, you deposit money into your bank account, you pay your credit cards from your bank account, and there’s not much else to it. There’s nothing inherently wrong about this, but there is a better way!
Here’s what we did to create our income flow:
#1 Established our bare minimum monthly household expenses
After doing the Expense Tracking and Categorization exercise, we had a bunch of categories of spending that we could total up to see our average monthly budget. We took every category except our business expenses, added them up, and that became our minimum monthly household expense number.
#2 Established our bare minimum monthly business expenses
Similar to the household expenses, the category from our ETAC exercise that grouped our business expenses together showed us our average monthly budget for business. Keeping this separate from household expenses is helpful if you have a bank account specifically for your business (which, if you work for yourself, you should!).
#3 Created a monthly schedule for transferring all excess income to a new account
It should go without saying that you need to be making more money than you’re spending every month. If this isn’t happening for you right now, you have a bigger problem at hand. Hopefully, after going through the ETAC exercise, you have some excess income that you can apply to your debt (especially if you found hidden money!). For us, we identified the excess money we made over our expenses every month and would transfer this to an external savings account to be applied toward our debt (more on this savings account in a moment).
#4 Scheduled a weekly budget meeting
Weekly budget meetings helped us deal with the shame and embarrassment of our debt.
This may sound crazy to you, but my wife and I decided to put a standing meeting on our calendars every week to start talking about our finances. This meeting would involve doing a couple things:
I could talk for hours about how vitally important these weekly budget meetings were for us (and continue to be). Not only did they help us get a firm grasp on our financial situation, but they also helped us deal with the shame and embarrassment of our debt. The more we discussed and attacked our debt every week, the less shame and embarrassment we felt about it.
If you don’t have a spouse to do weekly budget meetings with, find one! Just kidding… But ask a friend? Get a financial advisor? (More on the latter option in a bit as well).
#5 Set goal numbers of how much debt we could pay off each month (debt payoff schedule)
I’ll get into much more detail about this in Step #7 of this article. But the idea is to look at how much excess money you have above your expenses that you can immediately apply to your debt. Some weeks it may be $50, some weeks it may be $0, and some weeks it may be $500. The key is to continually know more information about your financial situation based on your income flow.
Creating an income flow isn’t rocket science, and I felt like we already had some semblance of a household budget, but using this new process was incredibly helpful. Our income flow consisted of these things:
When all your bank accounts can be seen on the same online banking dashboard page, it’s easy to see the money in one account as money available to any account. It wasn’t until our financial advisors introduced us to creating a completely separate external savings account (with a completely different bank) that we understood how important this was.
Our new savings account was nicknamed our “Debt Crusher” because that was its sole purpose for existing. We would transfer our excess cash from our Household Account (or sometimes Biz Accounts) and make debt payments from the Debt Crusher account.
Having a completely separate bank account that we couldn’t see next to our business and household bank accounts really helped us build momentum in paying off our debt.
No longer did excess money sit in our main bank accounts where it could easily be spent. That excess money got transferred to an account with one important job: Crushing debt!
Have you ever had a month where you realized you didn’t have enough money in your bank account to pay your electric bill? Maybe you’ve overdrafted a time or two and cursed yourself each time it happened? We’ve been there!
When you create your own income flow it’s extremely beneficial to add goals to each section. Our financial advisors gave us the sound advice to keep a goal amount of money in all our accounts as a buffer to never drop below (this helps avoid those crappy overdrafts!) I’m sharing our example numbers to give you an idea of how to set this for yourself…
For Caroline Biz and Jason Biz, our goal number was at least one month of average expenses. The idea was to never drop below that number again if we could avoid it. For Household, our goal number was also one month of average expenses.
And if you’re wondering, YES, we had to work our way up to these goal numbers. When we first set these goal numbers we did NOT have those amounts saved in each account.
This income flow exercise showed us that we should be able to pay down $4,500 of our debt every month (that was $54,000 in a year!). At the end of each month, we’d look at our debt payoff sheet (again, coming in Step #7 of this article) and pay down the different areas of our debt.
We didn’t always hit our exact $4,500 number, but it was extremely helpful and motivating to have a goal to hit each month.
TIP: Create an income flow of your own! Add goals for all your accounts, transfers, and get a clear picture of how much money you can apply to your debt every month.
There’s a reason why this article didn’t start here. It may seem like the “plan” should’ve been first, but what my wife and I realized through our journey to debt freedom was that we needed to get all our financial ducks in a row BEFORE we started climbing ladders and dodging barrels (yep, still running with the Donkey Kong metaphor, folks!).
Truthfully, you already have a big part of your debt payoff plan if you’ve done the Spend Less/Earn More, ETAC, and Income Flow exercises. But, let us show you four additional pieces to your debt payoff puzzle based on our experience paying off our $124,000 in debt.
Yeah, yeah, I’ve said this phrase multiple times, but it’s such an important mindset shift that you need to make when it comes to getting out of debt.
To remind you, we didn’t accrue our $124,000 in debt through lavish spending. However, do admit that our financial habits weren’t the best and there was plenty of room for improvement. A huge part of that improvement was setting budgets and sticking to them.
You cannot and will not get out of your debt if you continue to stick to the same financial habits you’ve had up until this point. You have to make changes.
The phrase that we came up with and that was a guiding principle over and over again while making sacrifices to get out of our debt was: Short term pain for long-term gain.
When we finally accepted the fact that cutting back for a few years didn’t mean cutting back FOREVER, it created a spark of momentum. Yes, we’d have to spend less money each month, travel less each year, and watch our dollars much closer every week, but those things would lead to removing the dark cloud of debt that hovered above our heads.
We want the same thing for you! So… say it with us: Short term pain for long-term gain.
Did you know that American Express has a hardship case that will lower your credit card interest rate (APR) to 0% for three months, 1% for the next 3 months, and then 9.99% for the 6 months that follow? All you have to do is call the number on the back of your American Express card and ask to talk to someone about a “hardship case.”
Hardship cases are made for people like you and us. We got into debt, it sucked, and we were worried about how we’d be able to afford the minimum monthly payments on our credit cards with how high the interest was on our cards. Credit card companies would rather lower your monthly interest rate (APR) then see you default on your payments (AKA: not give them your money).
I didn’t know a hardship case existed when I called American Express and was simply looking for any way to reduce my 24% APR. I hopped on the phone with a customer support person and explained my business was going through hard times and instead of defaulting on my payments, I was hoping there was some other option for me. That’s when the customer service person explained they had a program that would freeze all spending on my card, but would lower the monthly interest rate from 24% down to 0% for three months (then raise it to 1% the next three months, then raise it to 9.99% for the next six months).
These phone calls suck, but staying in debt sucks much worse.
If you apply for American Express’s hardship case, they do have to lock your cards during that time period. This sounds scary, but you shouldn’t be using your cards anymore anyway.
We also called the companies where we had other credit card balances with high APRs: CitiBank, Wells Fargo, and another American Express card. CitiBank and Wells Fargo didn’t have a hardship case like American Express they were both willing to lower our APR by over 10% on each card.
We spent just over an hour making these humbling phone calls to our credit card companies and were able to get our interest rates lowered to a point that would save us $400 in credit card fees each month.
That’s $4,800 annually, which when you add in the savings from our Expense Tracking hidden money we found, it meant we had nearly $15,000 to pay toward debt!
Ready to call your credit card company(ies) yet?
Note: We didn’t call our mortgage or student loan company to find out if they offered a hardship case of any kind. You could call and ask, it definitely wouldn’t hurt.
One of the craziest things I’ll never understand is that even when we were riddled with credit card debt, we could still get approved for additional credit cards! Insane.
Our financial advisors were happy with the hardship cases we were able to get with a few of our credit cards, but on some of them, the APR was still too high. They recommended we apply for cards with 0% APR and very low balance transfer fees. The idea is that we’d transfer the balance of an existing credit card with a high interest rate to a new card with a 0% interest rate and just pay the one-time balance transfer fee.
Here’s an example of exactly how we did this:
Step 1: I applied for the Discover It credit card (0% APR and 3% balance transfer fee)
Step 2: I got approved for the card with a line of credit of $12,000
Step 3: I transferred the balance of our Wells Fargo Platinum card to the new Discover It card ($12,000 balance x 3% transfer fee = $360 one-time balance transfer fee)
I repeated this process and signed up for the Chase Slate credit card, as they also offered a 0% APR. We moved over three separate cards that had over $9,000 on them and nearly 30% APR.
This part of the debt payoff plan is going to be dependent on your credit score and credit history. We were fortunate that we both had pretty great credit scores and credit history and could still get approved for new credit cards with reasonably high credit limits. If you can’t get approved for new cards, don’t worry, just skip this part of the debt payoff plan.
Note: We found the best 0% APR credit cards by checking out NerdWallet. They keep an up-to-date list and give you an easy way to apply. IMPORTANT: Be very careful when signing up for more credit cards, remember these are only for transferring your debt, not to use for spending!
You should aim to pay off the credit card or loan with the smallest balance AND highest interest rate first. As Dave Ramsey (“America’s trusted voice on money”) says, paying off one card creates a snowball effect. Once you see that first card (or loan) paid off, it motivates you to want to pay off the rest (instead of evenly reducing all debts). Think of paying off each credit card or loan like getting one level closer to that financial freedom princess!
Around the beginning of 2015, we had stashed enough money in our Debt Crusher account to pay off a credit card that had the highest interest rate. This was a CitiBank card with a 21% APR and a balance of over $14,000.
It was during one of our weekly budget meetings when Caroline and I hunched over my laptop. We logged into my CitiBank account. We clicked “Make A Payment.” We selected the magical option of “Pay Total Balance” (an option we hadn’t be able to select for many years). And we hit the glorious Submit button.
What a wonderful feeling that was! Up until that point, we’d only felt the mundane feelings that came along with paying minimum monthly payments. Yeah, some of our monthly payments had a little extra thrown in here and there, but none of them were as satisfying or motivating as paying off an entire balance. (I’d liken this to beating that first level of Donkey Kong where he not only throws barrels, but he starts throwing them rapid fire. Beating rapid fire Donkey Kong barrels proved to us that we could finally rescue our debt-free Princess!)
The little celebration we did lead to getting even more focused on wanting to pay off our debt as quickly as possible. We wanted to select all the “Pay Total Balance” buttons on all our debts. We couldn’t make it happen at that moment, but we could feel that snowball effect was in motion.
Hopefully this 4-part debt payoff plan gives you some really solid momentum toward debt freedom. Now would be a great time to make those hardship phone calls, look for 0% APR cards you can apply for, and get ready to organize all your debt in one place.
Congratulations friend, you are on your way to debt freedom! But before we release you into the financial wilderness with all the debt payoff strategies you’ve learned thus far, we have a pretty important spreadsheet to share with you.
Say it with me: Spreadsheets are our friends!
Just like you created a spreadsheet for Expense Tracking and Categorization (ETAC), it’s time to make another one that shows you exactly how much debt you owe. This additional spreadsheet will help you create a monthly payoff schedule that shows you exactly which debts need to be paid off in which order. This is the Debt Sucks Spreadsheet.
Seeing our debt laid out on one sheet was incredibly powerful. Yes, the total amount of debt staring us in the face sucked, but the fact that we could see a clear monthly path to paying off all our debt was incredibly helpful.
I’m going to walk you through how to use our Debt Sucks Spreadsheet step-by-step below. There’s also a video after the written steps if you want to see me using and updating the spreadsheet.
💸 Grab your own copy of the Debt Sucks Spreadsheet here.
When you open up the Google Sheet, you’ll need to make your own copy that you can edit. Simply go to the top menu bar: File > Make a copy… and boom, you’ll have your own version you can edit.
Now that you have your own copy of the Debt Sucks Spreadsheet, you’ll want to fill it out. Leave Column B as the last column you fill out.
Column A: This is where you’ll list your debts (credit cards, loans, etc).
Column C: Add the total current starting balance.
Column D: Add your interest rate (APR). Don’t be surprised if this information is hard to find!
Column B: The card or loan with the highest interest and lowest balance is your #1 priority (remember, this is the snowball effect).
If you have more than three debt items, we recommend copying and pasting one of the existing debt sections and adding it to the far right of the spreadsheet. Make sure to also add a new debt item in the top left section too.
You wrote down your credit card/loan balances in the top portion of the spreadsheet, now let’s add them to the corresponding color section below (to help you pay down those debts). Here’s a quick guide to where you need to match up your balances:
You only need to update cells C15, H15, and M15 in this step! The spreadsheet should update the rest of the cells automatically.
Once you’d add the Balance numbers to match, you can edit the Date and Amount Paid columns to match your debt payoff schedule. You may need to add more months, and you’ll certainly want to update the Date column to match your calendar. You enter monthly payment data in the Amount Paid that is your goal payment each month. (Once a payment is made you’ll change its background color to denote you made the payment.)
You will most likely not stick to the payment schedule you first write in. That’s okay! We didn’t either. Just make sure to go in and make the biggest payment you can and the Balance totals will update for you.
This is the only complex part of the Debt Sucks Spreadsheet, but it’s not as bad as you think! You want to update the formula that calculates the interest rate so you can see the actual amount of interest you’re paying each month.
To update the interest rate for the first debt item, click on cell D16 (or 16D). When you click that cell, you’ll see the formula in the bar at the top of the sheet. We’ve set the default interest rate at 10% (or 0.1 as written in the formula). All you have to do is take the interest rate you wrote in cell D2, convert it to a decimal, and update the formula.
Example: Let’s say you have a 5% interest rate (APR) on your credit card. You’d enter 5.00% in cell D2 and in the formula in D16 you’d change 0.1 to 0.05.
Example #2: If you have a 24% interest rate (APR) you’d enter 24.00% in D2 and in the formula in D16 change 0.1 to 0.24.
Repeat this process for all cells in the “Balance Plus Interest” column where a formula exists (when you click the cell).
Now that you have the Debt Sucks Spreadsheet setup with all your debts, your total starting balances, your interest rates, your estimated amount paid, you can start making monthly payments and denoting them in this sheet.
Don’t get discouraged if you can’t meet the goal you set for your monthly payments. Stick with paying down your debt and use this sheet to your advantage!
You know what sucks about debt? Talking about it often. But you know what helps get rid of debt? Talking about it often.
If you have a spouse or significant other, I highly recommend this being your financial accountability partner. Conversations about money SHOULD be had in a relationship. Money is evil. It causes so many problems when not discussed often.
Debt isn’t fun and neither is getting out of it. Don’t do it alone!
But if you don’t have a spouse or significant other, you’ll want to get some financial accountability from another source. Here are a couple of recommendations:
Online or local groups: Are you in any Facebook Groups or do you attend any local meetups? Could you ask around and see if anyone wants to team up on attacking debt together?
Financial advisors: I always thought of financial advisors as crusty old men who wore those bright green visors you see in paintings that usually involve games of poker. Maybe there would be cigars involved, but most certainly, being $124,000 in debt didn’t qualify to talk to financial advisors. Then we were proven wrong. We were introduced to our financial advisors through a friend and have been using them since 2013. I’ll also mention that you don’t have to be wealthy, rich, or even making much money to have financial advisors. We had none of those things when we started our relationship with the financial guys we use.
Ask your friends: It may sound crazy, but given the stats I shared earlier about the average debt in the US, you are very likely to have a friend who is in a similar debt position as you. Don’t be ashamed to ask. Heck, forward them this article and have that be the way you broach the subject.
No matter who you team up with, finding a financial accountability partner is hugely beneficial. It removes all the pressure from your shoulders and allows you to have someone to commiserate with. Debt isn’t fun and neither is getting out of it. Don’t do it alone!
I may sound like a broken record, but our weekly budget meetings were the turning point in our debt story.
I give my wife a lot of credit (money pun!), she was the catalyst for starting our weekly budget meetings. At first, I hated these meetings. It sucked to confront the debt we had, most of which was caused by me and my poor business decisions. But as we started to talk each week about our debt and how we were working through paying it off, it became a much easier topic to discuss. The shame and embarrassment started to melt away.
When you have 250+ conversations about anything, progress is bound to happen! Sure, some weeks our budget meetings are short and sweet. We download our data. We review our spending. We update our budgets. We’re on our merry way. But every few weeks it’s a much longer, and sometimes difficult conversation. Those tougher meetings are that much easier with all the boring meetings sprinkled in between.
We can clearly remember being blindsided by random bills, business expenses, or even income before these weekly budget meetings. Now, we feel completely in control of the flow of money coming in and out of our accounts. It feels really effing great.
When we created our first debt payoff plan I was hell-bent on paying off all $124,000 of our debt in 12 months. Well, things didn’t go according to plan. We didn’t make as much money as we’d hoped and we had a few unexpected expenses pop up. But just because we didn’t stick to our first debt payoff plan, doesn’t mean we gave up.
We were able to pay down $60,000 of our debt in the first 12 months of our debt payoff plan. And, a whopping $25,000 of that money came directly from doing our Expenses Tracking and Categorization exercise (and then setting budgets, making sacrifices, and making those tough phone calls). So, $25,000 of our first year’s debt payoff came directly out of money we already had and otherwise would have wasted!
Week after week my wife Caroline and I would sit down, go over our finances, make our monthly debt payments, and update our Debt Sucks Spreadsheet. It took just under two years, but we finally reached debt freedom.
On June 14, 2016, we jumped over that final debt-filled barrel and kicked Donkey Kong right in his credit-card-loving face.
I simply can’t type enough words to explain how great it feels to be debt free. That $124,094 used to make us feel ashamed and embarrassed, but now all we feel is pride.
Our very last credit card to pay off was carrying a balance of $9,639. When we paid it, we immediately grabbed a phone and took a selfie (which, obviously, needed emojis added to it).
Being 100% debt-free is a feeling like I’ve never felt before. It feels like so much more is possible in life. It feels like we’re in control of the decisions we make. It feels like we’re breathing some really sweet, sweet oxygen these days.
There is no perfect debt payoff plan. There is only the perfect plan you can create for your situation and your life.
Money is a deep, emotional subject for a lot of people and just talking about it can bring up a lot of negative emotions: guilt, shame, scarcity. But we promise the moment you acknowledge the barrel-throwing monkey in the room and make a plan to rescue your financial princess, things will start to change. They did for us.
Remember: It’s not going to happen overnight, and it’s not going to be easy. Short-term pain for long-term gain.
While the title of this article might suggest I want to show you how to spend all your money, it’s really an article about the different ways to invest your hard-earned cash.
Let’s talk about voting with your dollars, living a rich and full life, and understanding the fragility of being a human being*.
*Sorry to all of my mammalian and marsupial readers out there. I’ll have your back next time!
To give you a bit of background, my wife, Caroline, and I spent the past few years aggressively paying off $124,000 in debt.
You can read our full debt pay-off journey here. TL;DR: During that time, we made some important changes in our spending habits, one of the most important of which was listing out ALL of our expenses and having a hard look at where we were overspending and needed to make changes. (Pro tip: we do this exercise once every few months to make sure we aren’t falling off the financial wagon.)
One of the questions I’ve received the most after we became debt-free was:
That is a great question and I want to expand upon the title of this article and help you spend your money, or at least explain the thought process behind how we spend ours.
Enough well-off (read: rich) people and non-crusty financial planners repeated the same thing over and over again, so I finally started listening and applying their advice.
What were they repeating? Was it a hot stock tip? A slick investment strategy?
Nope. It was super boring. They were all talking about insurance.
Sure, almost everyone reading this probably already has car insurance. BUT… Do you have the right amount of coverage? Do you know your deductible if you were to get into an accident (and do you have a buffer of cash saved to cover that deductible)? Most importantly: you may be paying for the cheapest coverage possible, but could you pay just a few extra dollars to have WAY more coverage?
Our GEICO car insurance policy had decent coverage every month for the $78 we were paying. But, upon further inspection, we found that we could quadruple our coverage, cut our deductible in HALF ($5,000 to $2,500), and only spend $9 more per month. Yes, $9. Just based on the $2,500 smaller deductible, that extra $9 is worth it for the next 23 years (2500/9, then divided by 12).
We always assumed life insurance was a complete scam. Guys with slicked-back hair wearing ill-fitting suits, trying to get you to buy something you’d never use. That was, until we were told about Whole Life Insurance* and how it not only builds a policy that your spouse (or family) can benefit from if you pass into the next life, but can also be used as an investment account (netting 3-5% returns annually).
Now, you may be like I was a few years ago and not have a spouse to think about when you die. But I bet you have family members who could benefit from the policy if you took a trip on the No Longer Alive Express. And remember, it’s also an investment.
Find a recommended financial advisor (from a friend) and talk to them about life insurance. Avoid investing in life insurance from anyone who calls you unsolicited.
*I want to point out that Whole Life Insurance can get a bad rap on the Internet. You may also find Term Life Insurance in your searches. Truthfully, for every positive article on Whole Life, I could find a competing negative one. At the end of the day, I trusted the people who recommended this to me (close friends and biz acquaintances), and none of them were benefiting financially. That’s good enough for me.
Bring on the “snooze” alert. I want you to know, dear reader, I hate the idea of savings. I really do. You’ll read more about that in a moment. However, I hate the idea of being in a financial stranglehold if something goes wrong in life more than I hate the idea of savings.
When we finished getting out of debt, one of the first things we did was build up a reserve of cash (savings). There’s no tried-and-true rule here, but we wanted three months of expenses saved up as an “oh shit, everything went cray cray” fund. This became the first thing we put money toward after paying off all our debt. We squirreled away every dollar and put it—and this is key—in a bank account that wasn’t at the same bank as our other accounts. This external safety net account is one we rarely see and never touch (and that’s how it should be). The peace of mind we feel having this 3-month cushion is absolutely fantastic and something you must do for yourself.
For as long as I can remember, I never believed in saving for retirement. I enjoy the work that I do and want to enjoy my life at the same time. Now, does that mean I don’t make long-term investments? No, but I’m not buying into the same long-term investment plans as other people because I don’t have to. (We’ll get to that in a moment.)
Of course, you would, right?? Now, I’m not going to tell you to spend all your hard-earned money on Faberge eggs, lavish trips, etc. But I will tell you that we live our lives under the idea that human beings are fragile creatures. We get sick easily. We can contract some random illness, and our dreams of a long life can be squashed in a moment.
To me, it’s actually a bit short-sighted to think about living a rich life only when you’re much older. So here are some things we prioritize in our budget:
When we finished paying off all our debt, we knew we wanted to do one big trip to celebrate. We called it our “Moneymoon” (clever, I know), and we splurged on a bucket list journey to Tahiti. Yes my friends, over-the-water bungalows and all. This was our only big trip of that year. One trip. The other trips we took were all road trip-based (read: driving in our car to cheap AirBnBs or pet-friendly hotels).
(Obligatory Tahiti photo, sorry I’m not sorry.)
As we’ve continued to make a little bit more money each year, our travel budget has increased But we reflect on it each year, and we’re honest with ourselves about our priorities. There was a time our yearly travel budget was $0.00 because we had no money to spend, and it’s likely that could happen again if something more interesting pops up on our radar.
Semi-pro-tip: If you feel like you’re at the $0.00 travel budget place, I’d recommend using a savings app like Acorns. It’s free to use and can round-up your daily/weekly purchases to save little bits of money here and there. You can also set monthly withdrawals (I have $50 on ours). Last year my Acorns account accrued over $1,100 without me even thinking about it! Boom. Travel budget.
I believe the reason people (maybe people like you) feel guilty about going out to dinner or movies (or spending money on other discretionary things) is that they don’t budget for it.
When you have an idea of what you can spend on non-necessities, you create a cap for it, and then you don’t feel the guilt of spending it.
We have a $1,000 budget per month for entertainment. That includes:
Our budget didn’t start out at $1,000. A few years ago, it was something like $150 and included one nice meal and one movie night a month.
Here’s the really important thing about this category of spending: It’s one of the things that brings us the most repetitive joy in our lives. Exploring new restaurants. Seeing works of art on the big screen (or just huge explosions and 360-pans, thanks Michael Bay). We budget this happiness into our lives and are incredibly intentional about it.
I think often of Ricardo Semler’s TED Talk about “terminal days” and how similar it is to the idea of being intentional about how we spend our time. This is a paraphrase of how Ricardo puts it:
“On Mondays and Thursdays, I learn how to die. I call them my terminal days. A lot of people in my family died of melanoma, and I kept thinking that one day, I could be sitting in front of a doctor who looks at my exams and says, ‘Things don’t look very good. You have 6 months to live.’ And I started thinking about what I would you do with this last bit of time I had left. Spend more time with the kids? Visit these places? Go up and down mountains? We all think think we’re going to do all the things we didn’t do when we didn’t have the time. But I decided I’m going to do something different. I’m not going to wait to be diagnosed with a terminal illness. Instead, every Monday and Thursday, all year round, I do what I was going to do AS IF I had received a terminal diagnosis.”
I’ve done this by nature for as long as I can remember, but my friend Greg Hartle explained it to me in ways that made more sense as a business owner. I’m paraphrasing, but he said some version of this…
“Invest your money in your own projects because unlike stocks, bonds, and other standard investments, you can usually enjoy 100% of the returns (or more!)”
This mindset of investing in myself has drastically shifted my thinking, especially when I start to evaluate taking on a new project. Yes, new projects are shiny and fun and give you all kinds of dopamine responses, but they also come with pressure, stress, and a whole heap of work. Work that you aren’t sure will pay off.
For me, Teachery is one of these projects that I keep investing in and look to as my own long-term investment. If you don’t know, Teachery is an online course software that I co-founded in 2014, and it’s always been a side project.
Recently, however, I’ve started to think about creating more predictable monthly income, and Teachery was the logical place to start (especially when using the “invest in yourself first” mantra).
Here’s how the numbers break down when it comes to investing time and energy (which is another form of currency) into Teachery:
Goal: Increase Teachery monthly recurring revenue (MRR) by 3-4x in the next year
Our investment of time and money into Teachery will be recouped in four months if absolutely nothing changes. But I know things will change, because the money we’re spending is on things our potential customers are asking for (but that we don’t currently offer, so we’re losing their business).
At a 3-4x increase in customers and revenue, we’ll go from $6,000 MRR to $18,000 – $24,000 MRR (or $72,000 annually to $216,000). There isn’t a stock or fund you can put your money in that creates a potential increase of 300%! Plus…
You own it. You control it. It’s your playground, and no one can steal your bouncy ball.
Do you have a project that’s already generating revenue that needs some love? Maybe a small investment and some time could propel your business forward?
*The $18,000 was hiring a second developer for six months. We could have done all the work ourselves, but due to our limited time investment, this accelerated our roadmap immensely!
You may not have a software product like Teachery to invest in, but you may have a big idea that’s nagging at your thoughts day in and day out. I’ve had a few of these over the years, but most recently, BuyOurFuture was that project.
The initial idea behind BuyMyFuture was to provide maximum customer value to me for my projects ($1,000 per customer) and maximum “Jason’s projects value” to my customers (pay me once, get all my current AND future stuff).
When I started running the numbers on what it would take to make BuyMyFuture a reality, the expenses racked up. How much, you ask? Just shy of $9,000. That included:
Even though that $9,000 was a scary number to spend, I knew it would be an investment of my own idea that I’d get 100% of the returns from.
So, what happened?
Now, of course, not all ideas pan out and end up bringing in hundreds of thousands of dollars. I’ve chased after ideas that barely broke even. I’ve had ideas that ended up in the red. But the important way to look at this is that you don’t put all your eggs in one basket (diversify, as they say), and that you are doing things that YOU actually control the outcome (to some degree).
I’ll take investing in my own ideas over investing in ones where I have no control any day of the week.
*I share revenue numbers because they’re obviously bigger and more awesome. However, the profit numbers are worth sharing for transparency’s sake: total expenses for all three BuyMyFuture launches equal $105,000. Total profit is then $303,000.
This topic has become more and more important to me as I’ve been in the entrepreneurial game longer.
If you’re being completely honest with yourself, do you really want to see more big box stores out in the world? More huge companies that squeeze as much profit out of their employees and products? Or would you rather spend your money supporting world-changing businesses, industry-disrupting entrepreneurs, or maybe just a hand-crafteded brand run by one guy and his family?
Jeff Sheldon started a simple apparel company around the same time I started my IWearYourShirt idea in 2008. The idea behind his company, Ugmonk, was to create well-designed and high-quality apparel (instead of contributing to the fast-fashion world that makes things as cheap and mediocre as possible).
Every year since Ugmonk started, I’ve purchased something from Jeff. Whether it was a t-shirt, a mousepad, a Chemex coffee collar, or one of his anniversary sets, I have an annual Ugmonk budget.
(Not only do I spend money on Jeff’s products, sometimes I also create content about them because I want more people to know about it – a la his Kickstarter for “Gather.”)
As a minimalist, I don’t often need the things Jeff is creating/selling, but I want the Ugmonk brand to continue to exist. I want to do what small part I can to try to ensure Jeff continues to create beautiful, functional, and meticulously crafted goodies. That is why I have an Ugmonk budget* and why I will continue to have one for as long as Jeff is running Ugmonk.
*The best thing about my Ugmonk budget is it’s $200 per year. That may not make a huge impact on Jeff’s bottom line, but it makes a big impact for me to know I’m supporting Jeff on an annual basis.
Donating to various charities is something I’ve done since I was running my first business in 2006. Sure, I didn’t have a ton of extra money to donate, but as a small business owner, I knew how much of an impact a small amount of money could make.
I’m not one of those people who brags and shares every time I make a donation. Yet it’s an important part of my money-spending mantra to carve out a chunk of change that goes to folks who are doing good in the world.
Investing is great. Building a nest egg is great. But much like supporting businesses (like Ugmonk) with your dollars, it’s important to support the causes you believe in. Much like anything else that has to do with spending money, if you budget for and prioritize charitable giving, it doesn’t have to become an afterthought (or worse, the first expense you cut when money gets tight).
In a few years, you’ll be donating thousands, and it will have turned into a positive habit that you can’t live without.
There’s a lot to chew on here and I love focusing on taking action. Here’s your quick-hit list of what to invest in and where to spend your money:
We live in a time when you can always make more money. You can always work more. But if you aren’t actually enjoying your life, then what is it all for?
I wanted to touch on long-term investments before putting a pin in this article. I absolutely believe in “safe” long-term investments (like Index Funds, et al). At this moment in time, I don’t have the excess cash that makes sense to put towards long-term investments. It’s absolutely on the list—it’s just not the highest priority for our money-spending strategy (plus, that Whole Life Insurance does count as a long-term investment).
Then again… maybe I’ll never have a boring long-term investment because I’ll always be creating stuff of my own I want to invest in?
I’m of the mindset that inner alignment and building a life that brings you sustained satisfaction based on your unique values is always the primary goal. I’ll never try to sell you the “six-figure dream.”
That said, turning your creative gifts into a full-time income can be an incredible way to live out your values in a flexible, impassioned, and impactful way, so this complex relationship between creativity and money is one that I feel compelled to explore with you.
That’s why I want to continue our conversation from last week about the survey responses I received from so many of you at the end of last year.
When I asked about the relationship between your creativity and what brings you income, only 30% of you currently said you have a business that provides your full-time income, yet 70% of you said that’s what you are working towards.
That got me thinking about ways I can help you close the gap and help more of you that want to have a full-time creative business, get there (on your own terms and in your own way, of course).
One of the hardest parts of being a business person AND a creative person is that you are often paralyzed by possibilities. Which ideas to focus on, how to structure your day, how to balance practicality and idealism… these are all issues that I continue to confront, even now as I approach my fourth year in business.
It can often feel like you’re in a complicated maze of decisions, like you have 20 buckets before you and all you feel like you’re ever doing is filling them up one tiny drop at a time.
But, after two strong and profitable years in business, working less than I ever have with more joy than I ever have, I want to share with you the exact process I engage in every time I discover my business isn’t making the money that I want it to be making (or every time it becomes clear to me that I need to make a shift in how that money gets made.)
The most distinct personal example of this is probably back in 2014, when I was just six months into starting Made Vibrant as a freelance design business. I seriously considered shutting it all down and getting a job again because I was bringing in just barely $1,000/month, which wasn’t enough to maintain the lifestyle I was living. Before I threw in the towel though, I wanted to know in my heart that I gave it my very best try.
The process outlined in the steps below is exactly what I did to take my business from a struggling crapshoot to a strategic, fulfilling, profitable business. In a matter of just three months, I was able to lift my monthly income to $4,000/month. Those shifts I made quite literally saved my business, and this process is how I’ve approached things ever since.
My hope is that by outlining some specific steps you too can take, that it will empower some of you to formulate your own action plan instead of staying paralyzed in the dark when it comes to your creative business. If making a full-time income with your creative gifts is something you envision for yourself, I truly hope that today’s letter will provide you with some ways to confidently move toward that future.
Alright, buckle up… here we go!
You guys are one step ahead because we already tackled this!
Just as no bucket can remain full if there’s a leak in the bottom, no business can thrive with an owner who is self-sabotaging. Many of you are solopreneurs or have small teams, which means your mindset and behaviors greatly affect every inch of your business operations.
If you’re not flourishing financially in the way you want, the first crucial step is to take a hard, honest look at what could be preventing your progress on a personal level. Once you find a way to start rewiring or rewriting some of those stories, you’ll find that everything else in your business will begin to flow more easily.
(I’d like to add that I don’t consider limiting beliefs to include things like very real health or mental health challenges, which require a different approach to treating and thriving. Limiting beliefs represent the false, invisible barriers we place on ourselves mentally, things that we have the power to flip the script on if we are willing to work at it.)
Going back to that crucial moment in my first year of my business, I had MAJOR limiting beliefs around my lack of confidence and my fear of rejection. These barriers prevented me from sharing my design work or art (which was an important part of attracting clients) and it led me to set my prices WAY too low, leading me to be overworked and underpaid.
Once I was able to confront these self-imposed limits head on, I could work past them, eventually sharing more of my work and raising my prices, which I know contributed significantly to the lift (and survival) of my business.
After you’ve take the time to reinforce the foundation, that’s when you can move on to the business itself.
Some of you out there may have one single thing that you create that brings you money. Maybe you sell jewelry or you are a freelance designer and that is 100% of the work that brings you income.
That business structure allows you to focus on one main thing, which may be an efficient use of your attention and focus, but it also leaves you incredibly vulnerable because the health of that one business line defines the health of your entire business.
My approach from the beginning has always been to diversify with multiple revenue streams so that the success or decline of any one income source won’t be the end of my business. (It also is a natural consequence of being a multi-passionate and curious person. I have new ideas and those create new revenue streams!)
While I believe this strategy is beneficial overall, it does also present me with a challenge, pulling my attention in multiple directions. This is why it’s incredibly important at regular intervals to check in and ask ourselves:
What do I want to continue to work on and what can I let go of?
Every time I’ve realized I’m at a road block with the profitability of my business, it’s usually because I’m wasting energy on something that isn’t quite working or I’m NOT giving my full attention to an opportunity that is ripe for the picking.
So, this step becomes about understanding what is working, what’s not working, and why.
Here’s how to make that deduction:
I still to this day do this on the first of every month. I export the data from my payment processors like Stripe and Gumroad, and I enter it into a spreadsheet where I separate the transactions by project, total them up, and add them to a master sheet that shows me totals for the year on all of my various courses and products.
Thanks to spreadsheet magic, it only takes me about a half hour every month, but it’s incredibly powerful because it forces me to check in on a monthly basis and identify where my energy went vs. where my money came from at a high level.
In other words, answer these two questions:
This goes for money, obviously, but it also refers to other things. A project could bring you joy, creative growth, cultivation of a skill, collaborations with great people, etc. In my business, these are all things I want to take into consideration, though understanding that if financial lift is my primary goal, then that metric is what needs to carry the most weight at that time.
The same guidelines hold true for this question. You want to consider cost as well as other things. How much money did it cost you to produce that revenue stream? How much time? Energy? Did it take joy from you? Did it take patience from you? These are all things I write down.
Your Power Player = the revenue stream that brings you the biggest profit for the the least sacrifice. (ie. Output is disproportionately larger than input.)
Your Dark Horse = the revenue stream that feels like it has the most potential, if it was cultivated properly.
That could mean it’s the one that is the most enjoyable but still isn’t very profitable, or it could mean the one that brings you a decent income but it’s taking too much from you and needs a process overhaul to be enjoyable and efficient.
In other words:
What are the things you care about most, and does each of these projects align with those values? What do you want to be working on?
Keep in mind, there’s a balance at play here between doing work that lights you up, but also being realistic about what is working from a business perspective (we’ll dive deeper into this next week.)
Again, if you’re in a place right now where financial stability is your goal, you may have to cultivate the projects that aren’t the most ideal in terms of aligning with your values, but that can serve as a stepping stone to doing that bigger, more meaningful “heart work” after you’ve reached a more stable footing.
By this point, at the very least you should start to see a much clearer picture of what is actually bringing you money and what is not, as well as what is an opportunity and what is a time suck.
This exercise is what led me to start shifting away from client work in early 2015 because I saw that my online lettering course was bringing in almost double the income of my client work with far less time spent and far more joy.
By shifting resources away from a revenue stream that was a losing game for me to one that had great potential, I was able to use my very limited time a lot more effectively.
The top-level evaluation in Step 2 may be enough to illuminate changes you want to make right now in your business in terms of ways you want to allocate your resources. But, here’s the next logical question: What if you can’t just cut off an entire income source cold turkey? What do you do in the meantime as you transition out of it or as you redistribute your attention to new projects or opportunities?
What if you see a Dark Horse — an opportunity that could prove to grow into a Power Player for you if you just changed some things around?
The answer is in evaluating each revenue stream or product on a micro level.
It’s time to take an honest look at the product or service itself, your process, your costs, and your daily routines to see where you could be slowly leaking resources — time, money, or joy.
In my experience, there are usually three different issues at play when it comes to optimizing a revenue stream on a micro level. You can adjust the product, the promotion or the process.
Your goal at this step them becomes to:
This will help you more clearly narrow down what it is about each individual product or service that’s working or not.
By far the biggest hurdle for me in that bunch has been process, mainly because of the slow improvements I’ve had to make on my relationship with time.
Time is sneaky little thing! If I was a betting woman, I would wager that mismanaged time is responsible for the majority of businesses that aren’t where they’d like to be financially. There are a few different lessons I’ve learned about how to cultivate better habits with time, and it’s improved my business significantly, so I wanted to dive into that one significant detail here.
When I was doing client work and only making $1,000 a month, Jason sat me down and very kindly but honestly asked me if I was using my time effectively. I was defensive, of course, claiming that I was using every hour I could and doing my best, darnit!
Still, he asked me to do a simple math exercise which really highlighted for me the fact that I was losing a LOT of time without even realizing it.
He said:
Think of every hour in your day as one block. How many blocks of actual focused work would you say you can do every day (not answering emails, checking social media, doing admin work… but actually doing focused, project-based design work?)
I answered 5.
5 hours = 5 blocks. 5 blocks a day, at 5 days a week means I essentially had 25 blocks a week or 100 blocks a month of potential “work time.”
At the time I was charging roughly $75/hr, which meant the total possible income I could be making as a designer every month if I booked my schedule was $7,500 (compared to the $1,000 I was making.)
So why wasn’t that happening? Why wasn’t I making $7,500/month?
Well, that exercise made me realize a few things. #1) I wasn’t estimating my projects very well (I’d quote a project at 20 hours and spend 40 completing it.) And #2) I wasn’t booking my projects in an efficient way (without the visual “block” reference, I was only taking on one project a month because I was afraid of not having time to complete it. However, now armed with a way to estimate my time and conduct my time effectively, I felt empowered to get out there and book more business to fill up my “blocks.”
I’ll admit, it felt a little restrictive at first, and honestly, humbling. Am I really not savvy enough as a business woman that I have to map out every single hour of the day to book clients? That’s how it felt. That is until I started seeing the monthly revenue climb. More projects, less wasted time, more confidence, less second-guessing… it turned into a snowball that was actually working.
After I started to notice that, I was more than happy to put up with more structure than I was used to and trade a little bit of flexibility for the peace of mind that my effort was paying off.
Here’s what we creatives need to understand:
I know it’s not sexy. I know it sounds cold, and boring, and not the exciting artistic impact that we all want to make on the world, but remember:
“It’s much harder to make our mark on the world if we’re scrambling for income.”
Time efficiency can be the (unsexy) ally of beautiful, soulful art.
If we reframe structure through this lens, we have a better shot at building thriving and sustainable businesses.
Aside from the time block method, I also try to use tools like Toggl to keep track of how many hours a single project takes, which allows me to really factor in the time spent as a cost.
It might take some mental effort, but evaluating the nitty gritty details of each project and business line will arm you with the information you need to make smart improvements to your business.
Now that you’ve taken a critical look at your creative business from a macro perspective and a micro perspective, it’s time to make some decisions about how to act on this information.
Prioritization is key here because if you feel like everything has to change at once, it’s likely you’ll start to feel overwhelmed and nothing at all will change.
That’s why I prioritize by looking for one Big Brick Wall and one Big Cracked Door.
These are two terms Jason and I discuss in our Make Money Making course, but they are my way of evaluating how to move forward when I feel I’m at an impasse in my business.
A brick wall = An obstacle you find yourself repeatedly bumping up against.
A cracked door = A sliver of opportunity presenting itself to you.
Your BIG Brick Wall is the brick wall that sticks out to you most. It’s the one challenge that you find yourself repeatedly coming back to most often. It could be on a macro level — one revenue stream that just doesn’t seem to be working. Or it could be on a micro level — a product, process or promotion issue — that’s undercutting everything you try to do in your business. There are two ways to act on a Brick Wall, and that’s either to try and improve what’s not working or to simply let it go.
Your BIG Cracked Door is the opportunity that feels like it has the most potential. It could be an existing product that is performing better than you imagined and could benefit from more time and attention, like your Dark Horse from Step 2. It could be a promotion method that is working extremely well but that you haven’t set aside time to crank the volume up on yet.
You can even take the two birds, one stone approach here by simultaneously letting go of your Big Brick Wall in your business to divert your energy and attention to your Big Cracked Door.
That’s what I did when I transitioned away from client work over to products and courses. In doing so, I wasn’t spreading myself thin because I was eliminating one thing while replacing it with something that was a better fit for me, which is really what this entire process is about: figuring the best use of your limited time and attention to make the biggest financial impact on your business.
By this point you will probably have an idea of how to better focus your resources, which is a great start. But it won’t matter how efficient your processes are, how amazing your products are or how well-tailored your revenue streams are if you can’t form a meaningful connection with your audience. That’s why I had to include communication as the final step of the process.
In the Better Branding Course, I talk about getting clarity around the 4 Q’s of your business, which will help you form clear and concise messaging on your website, your social media posts, your newsletter — every single touchpoint you have with your intended audience.
Those 4 Q’s are: Why? Who? What? And How? (… and in that order!)
As Simon Sinek says, “start with why.” Why does your business exist? What is the underlying mission behind your work? Defining this and weaving it throughout your work will help you attract your ideal audience and it will help you stand out in a sea of other similar businesses. Speaking of your ideal audience…
Who do you want to serve? Who are your trying to connect with through your work? Who will pay for your products or services? Try describing this group of people not in terms of their age or gender, but in terms of what they believe and what they care about. Like two puzzle pieces fitting together, your WHO should be a specific type of person that will resonate with your WHY.
What are you promising people? What benefit do your specific services or products bring to people’s lives? Think of this not in terms of any details about your products but in terms of how your products make people feel and in what ways you make their lives better.
Finally, how do you deliver that benefit to them? Through beautifully designed jewelry or online courses or colorful art? This is where you get specific on the things you sell and offer your audience.
Once you can clearly and easily define these four things, you can weave the answers to these questions across every single aspect of your brand. As long as you are communicating these things clearly, authentically and consistently (all three are very important!), you’re setting your business up for the best chance it has to achieve your financial goals.
I know there are a TON of moving parts to this puzzle, and a LOT of information I’ve laid out here, but that’s because it is the true reality of running a creative business with soul.
There are people out there that would like to pretend that running an online business is as simple as blogging consistently, delegating a few things, building an email list, selling an online course and watching the money roll in. They paint this picture because it is what helps them sell the course promising to show you how you can do it too in “7 easy steps.”
As for me? My goal has always been to show you guys my personal journey in business — the complex decisions, the emotional hangups, and the messy evolution of it all.
In my experience, running a creative business is damn hard. It’s a constant battle with your own self-doubt, managing the ebbs and flows of the inevitable creative cycle. It’s sticking with projects long enough to see them through, but knowing when to let go of ideas that aren’t getting you where you want to go. It’s constantly holding on to what makes you unique, and it’s being brutally honest about your own strengths and weaknesses so you can carve out a path for yourself that is sustainable and authentic.
But it is also immensely joyful. And freeing. And constantly illuminating. This business has given me the financial fuel I need to live comfortably, yet also the flexibility I want to travel and make space to grow.
I hope the steps I’ve outlined above help you form a game plan if you’ve been stuck, and I hope it serves as a road map for what’s possible with effort and persistence.
Keep shining, keep making, keep working toward whatever vision you have for your life, and I’ll keep being here sharing what I learn along the way!