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Wandering Aimfully Through Running A Business

Instead Of Focusing On Growth, We Want To Focus On Enough: Our Journey To 330

Follow along as we try to achieve our "enough" number of paying Wandering Aimfully Members (spoiler: it's 330 members).
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Table of Contents



Our Goal: Reach 330 Paying Members In 12 Months


Update #1

September 1, 2018 (14.4% to goal)


Update #2

October 10, 2018 (19.2% to goal)


Update #3

November 15, 2018 (18.5% to goal)


Update #4

January 30, 2019 (21% to goal)


Update #5

March 30, 2019 (27% to goal)


Update #6

July 3, 2019 (30% to goal)


Update #7 (Final Update)

October 20, 2021 (100% to goal!!!)


The Tools We Use

What Makes Wandering Aimfully Tick

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Instead Of Focusing On Growth, We Want To Focus On Enough: Our Journey To 330


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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.

We believe the world is a better place when we’re sharing the FULL picture, authentically and truthfully.

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…

Jason and Caroline Zook, Journey to 330

Now that we’ve met, let’s talk about this goal of getting 330 people to join our Wandering Aimfully Membership.



Our Goal: Reach 330 Paying Members Within 12 Months (aka Journey to 330)

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:

So many times in our lives, we don’t actually define our individual/actual needs. We never stop to decide how big the bucket needs to be. We never stop to decide how much is ENOUGH.

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.

For us, our enough is 330 Wandering Aimfully members

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:

  1. We’ve been working for ourselves since 2007 (Jason) and 2013 (Caroline), with both of us focusing on helping creative entrepreneurs since 2014.
  2. We have a (now combined) email list of 16,000 subscribers.
  3. We have a (now combined) website that averages 50,000 visitors per month.
  4. Our membership community had 400 active members grandfathered (or grandmothered) in from a previous project called BuyMy/BuyOurFuture.

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.


How did we get to $33,000 MRR as our GOAL “enough” number?

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.”

Our average monthly living expenses: $12,000

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 average monthly business expenses: $5,000

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).

The average monthly amount we’ll set aside for taxes: $3,000

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!

The average monthly amount we *want* to save: $10,000

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.

The average monthly amount we want to use for wealth redistribution: $3,000

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.



The Starting Line and Getting 14.4% Past It (Everything Before September 1, 2018)

As of September 1, 2018:

Monthly Recurring Revenue (MRR): $4,783
Total Paying WAIM Members: 48

14.4% to goal

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:

  • Shared everything it took to build Wandering Aimfully
  • Had an entirely new membership dashboard built
  • Did a pre-order launch of our memberships in May
  • Did the initial launch in August (20-27)

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.

Under Construction Wandering Aimfully Website

Our first 15 paying customers: May 2018 Pre-Order

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.

Wandering Aimfully Pre-Order Page

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…

The WAIM Pre-Order brought in 15 buyers, netting us $1,483 in MRR

Wandering Aimfully Pre-Order Metrics

(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.)

Our next 35 paying customers: August 20-27, 2018 Launch

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.

Leading up to August 5, we created lots-o-content!

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:

Wandering Aimfully Lead Up Marketing

From August 5 to August 20 we warmed our audiences up to our first launch

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).

While keeping our audiences ready, we wrote our sales email sequence

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.

Wandering Aimfully Sales Email Google Doc and Drip Campaign

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:

  1. Monday, August 20: New site is live! Memberships are OPEN! 😱
  2. Tuesday, August 21: Case studies and testimonials 👫👫
  3. Thursday, August 23: New resources to be added in September for members 🤩
  4. Saturday, August 25: How can WAIM help you? Reply! 🤔
  5. Monday, August 27: Memberships are closing tonight 😬
  6. (We didn’t end up needing to send this email, as you’ll read!) Monday, August 27 (evening): Last call!!! 😳

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.

Wandering Aimfully August 2018 Sales Campaign Emails

Wait, 35 new customers, I thought you said 30 was the limit?? Let’s dive into the data of our first launch…

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:

  1. We had two pre-order buyers cancel during the launch, so we figured we’d just fill their spots and let two new people come in
  2. We had one new customer cancel the day after they purchased
  3. The counter that tracks our amount of member spots left is completely manual and we may have forgotten to update it when a buyer came in overnight (whoops!)

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 during the launch:

Wandering Aimfully Launch Week Website Analytics

To recap: As of September 1, 2018, we’re at $4,783 MRR (or 14.4% of our goal)

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:

The BEST part of our first 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.

Wandering Aimfully Slack Member

The WORST part of our first launch?

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).

One last thing: We’ll be using Baremetrics to publicly track and share our progress

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.

Wandering Aimfully Baremetrics Dashboard

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.



UPDATE #2: OCTOBER 10, 2018

After Our Second Launch We’re 19.2% Toward Our “Enough” Goal (Sept 2 – Oct 10, 2018)

As of October 10, 2018:

Monthly Recurring Revenue (MRR): $6,350
Total Paying WAIM Members: 62

19.2% to goal

Monthly Profit and loss:

Total WAIM MRR: $6,350
Total WAIM Fees (Stripe/PayPal): $160
Monthly Expenses in September: -$3,496

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…

Caroline got shingles and it royally sucked!

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.

Caroline got shingled.

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).

We launched our podcast/YouTube show, aptly titled Wandering Aimfully: The Show!

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.

Wandering Aimfully: The Show Recording Setup

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.

Wandering Aimfully: The Show on iTunes

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!

During our second launch we had 18 new paying members

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.

New Wandering Aimfully members in October 2018

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.

Launch Group #1 – New subscribers who didn’t get the 7-day sales sequence in August (408 subscribers)

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).

Launch Group #2 – Existing subscribers (15,931 subscribers)

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!

New WAIM Member

How does it feel to not hit our goal of 30 new paying members (and thus miss our revenue goal)?

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.

To recap: As of October 10, 2018, we’re at $6,350 MRR (or 19.2% of our goal)

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…

The BEST part of our second launch?

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.

Wandering Aimfully Membership Growth

The WORST parts of our second launch?

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).

WAIM Member Cancelations

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.


UPDATE #3: NOVEMBER 15, 2018

After Our Third Launch We’re 18.5% Toward Our “Enough” Goal (Oct 11 – Nov 15, 2018)

As of November 15, 2018:

Monthly Recurring Revenue (MRR): $6,133
Total Paying WAIM Members: 62

18.5% to goal

Monthly Profit and loss:

Total WAIM MRR: $6,133
Total WAIM Fees (Stripe/PayPal): $128
Monthly Expenses in September: -$3,590

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.

Our MRR went DOWN after our third launch, and, truthfully, that sucked.

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 humans love drama. We don’t like to just watch other people succeed without challenges.

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%).

WAIM November Churn

While it sucks that people canceled the memberships, it’s a great opportunity for us to learn what we need to improve upon.

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.

Is it possible that we can fix this problem of overwhelm and hopefully reduce our member churn in the process?

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!

We hosted three workshops in the past month and people loved them!

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.

WAIM Workshops

Workshop #1: Selling Without Feeling Sleazy

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!)

Selling Without Feeling Sleazy Workshop Analytics

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!).

Workshop #2: SEO & Google Analytics (Members Only)

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.

WAIM Members-Only SEO Workshop

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!)

WAIMs are happy!

Workshop #3: Our “Customer Journey Marketing Plan” Exercise

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!

WAIM Marketing Workshop Attendees

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:

WAIM Workshop Sales Pitch

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…

We believe that WAIM Memberships are a bit too general and don’t solve a specific enough problem for prospective customers.

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.

With only 7 new members joining in November (and 12 people canceling in October), we have to make a change.

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.

WAIM 6-Month Program Preview

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.

Soooooo, what the heck are the next steps to accomplish building this 6-month program?

  1. We’re going to plan out the curriculum for this 6-month program
  2. We’re going to create the content for this program (with assistance from our existing members) and build it into our membership dashboard
  3. We’re going to rewrite parts of our website copy and reposition WAIM on our sales page
  4. We’re going to try to do all of that by January… eek.

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!)

To recap: As of November 15, 2018, we’re at $6,133 MRR (or 18.5% of our goal)

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.

The BEST part of our third launch?

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!

New WAIM Customers in November 2018

The WORST part of our third launch?

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!)


UPDATE #4: JANUARY 30, 2019

After Our Fourth Launch We’re 21% Toward Our “Enough” Goal (Nov 15 – January 30, 2019)

As of January 30, 2019:

Monthly Recurring Revenue (MRR): $6,917
Total Paying WAIM Members: 73

21% to goal

Monthly Profit and loss:

Total WAIM MRR: $6,917
Total WAIM Fees (Stripe/PayPal): $342
Monthly Expenses in September: -$2,963

Quick hits of what we did this month:

  • Went through the busy holiday season!
  • Planned and created our new program Build Without Burnout Academy
  • Hosted a Members-Only Quarterly video call
  • Created and shared “Pretend People Problem” videos/articles (3 of ‘em)
  • Continued recording and promoting our weekly podcast/show episodes (11 eps)
  • Edited and released our first travel video (Tahiti!)
  • Put together an in-depth guide on transitioning from Clients to Products
  • Hosted a video workshop to help folks transition from Clients to Products
  • 20 posts on WAIM Instagram
  • Completely redesigned and rewrote our sales page 😱
  • Flew back to Florida for Christmas with our families
  • Gained 22 new WAIM members with our last monthly launch (for now)
  • Jason had jury duty for a day (WOOF)
  • And poor Caroline has been dealing with terrible anxiety


There is a tonnnnn to get caught up on but we’ll start with the unfortunate part of this update…

Caroline has been struggling with some really bad anxiety the past few weeks.

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.

View this post on Instagram

Let's get real.⁣ ⁣ This morning we made the tough decision to push back the start date of a new program we've been working on for months. ⁣ ⁣ The truth of the matter is Caroline is dealing with some rough anxiety and it's not worth pushing each day and risking her long-term health.‏⁣ ⁣ _ We sent an email to our 400+ existing WAIM members making the announcement that we'd be pushing back the start date. Writing and sending that email sucked. Even worse? We are finishing up another launch of our membership right now and feel like we're letting new members down.⁣ ⁣ But… The replies to our announcement email have left us floored.⁣ ⁣ Caroline's current bout with anxiety has made us realize how many people deal with anxiety on a day-to-day basis. So many people are replying that they or a loved one are affected by it.⁣ ⁣ A big part of me didn't want to make this public. We thought about keeping it quiet & working with our members behind the scenes. However, this shit is real. Running your own business can lead to some rough patches & it's important to share that almost ALL of us go through it.⁣ ⁣ There's no way for me to understand how awful Caroline feels, I only know how helpless I feel watching her be in pain. All I want to do is take the pain away. All I want to do is absorb what she's dealing with, even for a few hours so she can feel better.⁣ ⁣ Our health should be our #1 priority. ⁣ ⁣ We can't run a business if we can't get out of bed. ⁣ We can't create things if we can't function.⁣ We can't show up for other people if we don't take care of ourselves.⁣ ⁣ It's easy to pretend like nothing is wrong and try to push through it.⁣ ⁣ I know that admitting this publicly will dissuade people from joining our membership. I know it will hurt our sales goals. It's just the nature of how things work. I'd rather people also know how honest and transparent we are. Our lives are not a beautiful highlight reel.⁣ ⁣ While we believe in working hard we also know that there's a negative side to spending all these hours plugged in, scrolling, typing, and being constantly connected. ⁣ ⁣ Continued in the comments…

A post shared by Jason Zook (@jasondoesstuff) on

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.

Let’s gracefully transition to discussing our 6-month program Build Without Burnout Academy – the newest addition to our WAIM Membership.

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.

What we came up with was honing in on the exact transition we made in our businesses: Going from working with clients to selling digital products.

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!

Build Without Burnout Academy

We had many conversations and planning sessions about Build Without Burnout Academy. There were a few key components it had to have:

  1. It would be a guided weekly program that took 6 months
  2. We wouldn’t focus on some 6-figure dream outcome
  3. The content had to be bite-sized and actionable
  4. We wanted to pull in our best advice from other workshops/courses
  5. There would be monthly calls to bring program participants together
  6. There had to be an element of fun!

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!)

👍 The GOOD news about Build Without Burnout Academy

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.

👎 The BAD news…

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.

Our 4th WAIM Membership launch brought in 22 new WAIM Members (from January 21-28)

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.

WAIM January growth and churn

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.

Interesting tidbit #1: We’ve had 102 total people join our membership (73 are active and 29 have canceled)

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)?

Interesting tidbit #2: I (Jason) came to the realization that I’ve directly communicated with every single one of our 40 most recent members before they joined

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:

Tweets with Amy Hoy

So…. How do we move forward with our sales process?

We’re going to create a “Test Drive the WAIM Membership” experience and move away from the monthly launch model.

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)?

Step 1 in creating our WAIM Test Drive: Build a simple experience that walks potential customers through the highlight reel of our membership

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”:

Wandering Aimfully Membership Test Drive

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.

Step 2 in creating the WAIM Test Drive: Replace the section on our homepage with a preview of the test drive

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).

Step 3 of the test drive: I will email each person who signs up personally. Yep. Every single one. Not through an email automation sequence.

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.

To recap: As of January 30, 2019, we’re at $6,917 MRR (or 21% of our goal)

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…

Wandering Aimfully Membership Growth May 2018 to January 2019

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.


UPDATE #5: MARCH 30, 2019

We Are 27% Toward Our “Enough” Goal (Jan 31 – March 30, 2019)

As of March 30, 2019:

Monthly Recurring Revenue (MRR): $8,917
Total Paying WAIM Members: 97

27% to goal

Monthly Profit and loss:

Total WAIM MRR: $8,917
Total WAIM Fees (Stripe/PayPal): $400
Monthly Expenses in September: -$3,625

Quick hits of what we did this month:

  • Decided to stop doing monthly launches
  • Implemented and launched a “WAIM Test Drive” (lots more on this)
  • Upped our sales conversion from .05% to 6%
  • Finished the initial production of new program: Build Without Burnout
  • Hosted a live kickoff call for Build Without Burnout
  • Paused all updates on WAIM Instagram
  • Paused all new episodes of WAIM Show
  • Canceled our trip to Norway
  • Jason’s taken on a few 1-on-1 coaching clients
  • BIGGEST CHANGE: Switching (back) to Lifetime Membership
  • And Caroline has still been dealing with terrible anxiety


We upped our new member conversion from .05% to 6% 🙌

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)…


The idea behind the WAIM Test Drive was to take what was working from the monthly launch model and see if we could tweak or change it to work better.

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.

What is the WAIM Test Drive and how did we create it?

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).

Wandering Aimfully Membership Test Drive

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 WAIM Test Drive has become a more automated way to sell WAIM Memberships but for the first few weeks, it was completely manual.

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:

Wandering Aimfully Membership Test Drive Google Sheet

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.

  1. Would people actually sign up for it?
  2. Once they signed up, what emails would get them to reply?
  3. How many emails were too many when following up?
  4. What kind of sales page worked best?
  5. How could we make the test drive fun and feel WAIM-ish?

From a lot of experience trying to automate sales funnels over the years I’ve tried to automate things too quickly and without testing to see what actually worked.

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.

I emailed 107 people over the course of 14 days to figure out how to build our new WAIM sales workflow.

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.

WAIM Test Drive Email

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:

  1. Someone signs up for the WAIM Test Drive
  2. Using Zapier, I zap their information into a Drip email workflow
  3. The Drip email workflow is 4 emails long, spaced out 2-3 days between each
  4. The 4th email is a “harder” sell, but there’s no urgency, just honesty
  5. Using the same zap, their info gets added to the Google Sheet to keep track
  6. Once the email workflow is done, they get added to our WAIM Weekly emails

Since starting the WAIM Test Drive on February 12, we’ve had 412 signups and 25 people converted to paying members!

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).

WAIM Test Drive Signups

(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.)

A BIG change during the WAIM Test Drive is we decided to transition our WAIM Membership pricing back to our “Lifetime” model.

This was a pretty big decision to make because it drastically affects the ongoing MRR business model we’re creating with WAIM.

WAIM member happy with lifetime pricing

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.

Our hypothesis going forward is that we’d rather have a customer stay on and pay us $2,000 total and have to find a customer to replace them at the end of their payments (instead of fighting to keep more customers on longer in the beginning).

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!

Emailing with an existing WAIM customer about pricing changes

How does the change from ongoing monthly payments to lifetime ($2,000) affect our “enough” number?

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:

WAIM MRR with 15% churn

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:

WAIM MRR with 5% churn

(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.

Switching WAIM Memberships to our lifetime pricing model feels right to us.

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.

In more personal news, we moved and Caroline is only feeling marginally better.

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!

New Zook home!

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.

Caroline Zook in a dog bed

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 wanted to add an entire section to this update about our new program Build Without Burnout Academy…

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:

Early love for Build Without Burnout Academy

To recap: As of January 30, 2019, we’re at $8,917 MRR (or 27% of our goal)

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.


UPDATE #6: JULY 3, 2019

We Are 30% Toward Our “Enough” Goal (Mar 31 – July 3, 2019)

As of July 3, 2019:

Monthly Recurring Revenue (MRR): $10,033
Total Paying WAIM Members: 106

30% to goal

Monthly Profit and loss:

Total WAIM MRR: $10,033
Total WAIM Fees (Stripe/PayPal): $433
Monthly Expenses in September: -$3,512

Quick hits of what we did this month:

  • Caroline started feeling better!!! 😍🙏
  • Tried a first-month free offer
  • Moved back to bi-annual launch schedule
  • Did a bi-annual launch (it was odd!)
  • Tested some retargeting ads on FB
  • Hosted our 2nd + 3rd live calls for Build Without Burnout
  • Set up and started a 7-day free trial
  • Started recording WAIM Show again
  • Started using RightMessage a bit
  • Planned a new “marketing engine” called Make500
  • Continued 1-on-1 coaching clients


Time flies when you’re trying ALL the things!

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.

With Caroline starting to feel better, it feels like we can accomplish 100x more, but we have to be careful.

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…

View this post on Instagram

Hiiiii friends! Jason here 👋 just wanted to say hey and that Caroline is starting to feel more herself every day 🙌🙌🙌. We’ve been spending time enjoying the summer weather in SoCal but also still going through ups and downs each week. _ We’re extremely grateful for you peeps. Knowing we have an amazingly supportive community is so wonderful and we hope to be back in the saddle posting, sharing, and creating fun content very soon. _ But…. we’re not rushing back just to be active on social media. We want to go at our own pace, get into a comfortable routine and really focus on the stuff that matters most right now (which, unfortunately, isn’t spending a lot of time on IG, etc). We love your faces and hope you’re taking time to enjoy summer and wander aimfully through life and biz at YOUR own pace too 🤗👩🏻👨🏻‍🦲

A post shared by Caroline & Jason Zook (@wanderingaimfully) on

Our WAIM Test Drive was working like a charm… until it wasn’t…

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:

Paul Jarvis Slack Chat

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?

Here are the total numbers as it relates to the WAIM Test Drive:

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:

WAIM Test Drive Email Open Rates

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.

We’ve been doing email marketing for many years now and the last thing we want is to grow our list with folks who aren’t going to keep opening our 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 had our first big “launch” to get membership signups since the beginning of the year and it was ODD 🤣

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:

  1. 30% of sales in the first 48 hours
  2. 30% of sales in the middle
  3. 40% of sales in the final 24 hours

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.

We also spent $1,400 on retargeting ads on Facebook during the launch and it only netted 3 total conversions.

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).

One thing we heard from people during the launch was how much they liked our switch back to Lifetime pricing BUT they were still a bit confused on what a WAIM Membership was all about.

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 want to create a really focused and solid lead-in to potential new paying members and solve one specific problem for them (project: Make500)

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

Make500 with a mini-course

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.

With all that being said, if we zoom the lens out on our “enough” journey, all of our experiments are working!

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:

May 2018 to July 2019 MRR Growth for WAIM Memberships

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:

Happy WAIMers!

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!

New customers vs churned customer March 31 - July 2

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??)

To recap: As of July 3, 2019, we’re at $10,033 MRR (or 30% of our goal)

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!


UPDATE #7 (Final Update): October 20, 2021

We Hit Our “Enough” Goal!!! 🎉🎊🥳

As of October 20, 2021:

Monthly Recurring Revenue (MRR): $35,400
Total Paying WAIM Members: 278

100% to goal!!!

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

Quick hits of what we did the past two YEARS 😂🙈:

  • Repositioned WAIM from a membership to a coaching program
  • Launched a 6-month coaching package to test having a smaller commitment for members
  • Closed down our 6-month coaching package and repackaged the core offering to “WAIM Unlimited”
  • Completely redesigned our sales page
  • Committed to indefinite ongoing monthly coaching
  • Created a more sustainable bi-annual launch strategy and stuck with it
  • Found a consistent email growth strategy that increased subscriber growth by 400% (using a free quiz)
  • Stayed the course with our weekly podcast 🎙
  • Experimented with IG Reels and YouTube content (spoiler: not worth it)
  • Launched our affiliate program AFTER feeling like we really hit our stride with our core offer
  • Continued doing monthly live coaching sessions (25 and counting)
  • Weathered the uncertainty of Covid-19 🦠 like everyone else 😞
  • Took FOREVERRR to update this post!


Okay, wow, we really dropped the ball on updating this post…

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 you get jumped to the ENDING. Oof. 😅

Okay, that’s us trying to make amends. Cool? Hopefully, cool. Also, as a reminder, this is us:

Caroline and Jason Zook

Summer 2019: Let’s pick up where we left off and talk about our big pivot into a 6-month coaching program (MRR at this time: $10,000)

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:

  1. We wanted a smaller-priced offer to test a customer not having to mentally decide on a bigger $2,000 purchase
  2. We wanted to keep the $100 per month payment number so it was easy math if someone wanted to upgrade to our $2,000 product (and have their payments go toward it 👍)
  3. We truly didn’t know if we’d like doing the live monthly coaching so we only wanted to lock ourselves in for six months

We are VERY HAPPY to report this was the most impactful move* we made for WAIM as a business!

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.

Non-financial inflection point WAIM

*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.

Spring 2020: Our 6-month group coaching led to the repositioning of WAIM Unlimited and our core offer (MRR: $13,750)

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! 👍👍

Happy WAIM Customers

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:

WAIM Coaching Hub

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:

WAIM Coaching Recording Setup

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.

Fall 2020: Really dialing-in our bi-annual launch plan and creating our Un-Boring Business Roadmap (MRR: $16,950)

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:

We kept hearing from our members that they LOVED the monthly coaching, our courses, and our workshops, but they weren’t exactly sure what to do next in their business.

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:

  1. 🧱 Setting your business foundation
  2. 🛒 Creating a compelling offer
  3. 🌉 Setting a promotion & marketing strategy
  4. 📣 Attracting an audience with valuable content
  5. 🖥 Designing a website to support your strategy

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:

WAIM Un-Boring Roadmap Flow Chart

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.

WAIM Un-Boring Roadmap

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!)

Fall 2020 was also our first enrollment period where we had an affiliate program. 47% of new customers during our Fall 2020 launch came from affiliates!

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):

6-Month vs Unlimited comparison

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:

Spring 2021 revenue jump

Spring 2021: Covid hits our family, but we continue doing what works and see the fruits of our labor (MRR: $24,400)

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!

WAIM Spring 2021 Launch Recap

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.

  1. We built a 2-month lead-up plan for our affiliates
  2. We sent a total of 8 emails that included affiliate info and reminders
  3. We had 3 in-depth affiliate documents to help our members
  4. We create swipe copy, pre-written sales emails they could edit, as well as a slew of WAIM-branded graphics they could use on IG, Twitter, FB, etc
  5. We reminded them of our awesome 40% lifetime commission (they make $800 total on each new member they bring in)

WAIM Spring 2021 Affiliates

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!

We also had an IG Reel go viral during our launch but it didn’t have the effect you probably think it would.

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 😂😂.

@wanderingaimfully IG Reels

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 📉😅.

October 2021: The “WE’VE MADE IT” moment on our journey to enough 🥰💸🥳 (MRR: $35,400)

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!

What’s the point in working so hard to reach a goal if you don’t enjoy as much of the journey to get to the finish line as possible?

Jason Zook Stock Tank Tiny Pool

(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:

  1. 📬 Our email list was growing consistently without spending any money on ads to do so (all organic growth)
  2. 🔮 Our website traffic was slowly decreasing BUT our conversion from website traffic to our email list was actually improving (thank you quiz!)
  3. 🥰 Our existing WAIM members were loving our monthly coaching
  4. 🚀 Our affiliates were ready and waiting to promote our next enrollment

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:

WAIM Journey to Enough Goal Met

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! 🎉🎉)

Caroline and Jason Zook

Great, the celebratory dance has been done ☑️. So, how did our Fall 2021 launch break down?

WAIM 2021 Fall Launch

WAIM 2021 Fall Launch Affiliates

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.

So… what’s next? Do we just stop allowing any new members to join and we’re done?

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:

  1. We have reached our enough number, which means we can slow down all the promotion/marketing/outward effort to eagerly grow our revenue
  2. We will continue to send our weekly email newsletter, share our lives/ideas on IG, but we won’t be making any big pushes to grow our audience at all
  3. We will still do our bi-annual launches moving forward but we won’t be putting extra effort into affiliate pushes or additional marketing
  4. We will use our time and focus to pour back into our members and create a positive WAIM experience for them, trusting our word-of-mouth marketing engine
  5. Basically, we’ll be a bit quieter externally about WAIM, and we’ll use 2022 as an experiment to watch as members finish paying off WAIM and new members join

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! 👩🏻‍🦰👨🏻‍🦲🤗



The Tools And Resources We Use To Make Wandering Aimfully Tick

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!

Instead Of Focusing On Growth, We Want To Focus On Enough: Our Journey To 330

(Big Fat Takeaway)

We believe that defining your "enough" number in business is the only way to ever feel satisfied and to avoid the trappings of never-ending growth.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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