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173 – Why We Love 30-Day Challenges and Our Next One

Wandering Aimfully Through Our Podcast: What is it all for?

173 – Why We Love 30-Day Challenges and Our Next One

We haven’t done a 30-day challenge in quite awhile, but that’s all about to change with a content blitz we’re embarking on starting this week!
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Listen to our full episode on Why We Love 30-Day Challenges and Our Next One below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.



Five Key Takeaways for Why We Love 30-Day Challenges and Our Next One

1. We’re embarking on a 26-day content blitz (YouTube videos + Articles)

We haven’t done anything to spice up one of our WAIM Unlimited launches in a long time, especially from an outbound content marketing standpoint. At the start of 2023, our intention was to revitalize our article content by publishing new articles, which is a word that Jason likes to call, Narticles. This 26-day content blitz for us is going to give us 26 new articles (Narticles) on our website that capture 26 fundamental ideas about how we believe you should run an intentional online business. There’s a reason we’re not doing 30 articles, which will be revealed when the project goes live on September 18.

2. Ephemeral vs evergreen content, a two-part strategy

We have been using these terms ephemeral and evergreen as it relates to this 26-day content blitz. Anything that lasts a day or even a week (i.e. Instagram posts, TikToks, Instagram stories) belongs in the ephemeral category, while articles, YouTube videos, and even podcast episodes belong in the evergreen category. We think that a healthy business has a content strategy that incorporates both.

For discoverability, we’re going to use YouTube along with this 26-day content blitz plan to create a daily video that goes up with an accompanying article. The video is essentially the same content as the article, but they kind of serve two different purposes. The articles are a bit more evergreen and the videos are a bit more ephemeral.

3. We’re creating a new landing page for the articles on our site

Right now, when you land on the Wandering Aimfully website, it’s fairly difficult to find our best, helpful content. This is why we’re going to have a new landing page for our articles where we can showcase 26 pieces of content that would have a breadth of information, containing our top-level best articles, as a FIRST point of contact for a new WAIM website visitor.

4. Why we love (and don’t love) 30-day challenges

Why we love it:

Why we don’t love it:

5. This week’s “Calm Business Confidential” shout outs

In this new podcast segment, we feature businesses that seem to have a model that allows for living a good, calm life (i.e. not managing teams of hundreds of people or chasing huge [stressful] revenue goals).

This week:

👨🏻‍🦲 Jason’s feature: Marie Martens + Filip Minev SaaS Tally.so (form builder software)

👩🏻‍🦰 Caroline’s feature: Tim Koa’s sticker company Turtle Tags + YouTube Channel (Etsy/Shopify shop)

If you have a calm business you think we should talk about, send us an email and share it!


Show Notes for Episode 173: Why We Love 30-Day Challenges and Our Next One

One of the best ways you can get over imposter syndrome, build a skill quickly, or drum up marketing attention is through a 30-day content creation challenge.

In this episode, we’ll share why we think 30-day challenges are great for growing your biz and we’ll share the reality of how much work they can take. And yes, our content challenge is 26 days, not 30, but it’s cool if we round up, right??

We’ve done different 30-day challenges over the years but it’s been quite a while since we’ve focused on recording consistent YouTube videos and writing helpful business articles. And that’s exactly what we’re going to do for the next 4 weeks as a lead-up to our Fall Enrollment for WAIM Unlimited.

Tune in to future episodes for updates and on September 18, our 26 days 😉 of content will start being published!


Full Transcript of Episode 173: Why We Love 30-Day Challenges and Our Next One

⬇️ You can also download the .TXT file of the transcript

Caroline: Welcome to What Is It All For? A podcast designed to help you grow your online business and pursue a spacious, satisfying life at the same time. We’re your hosts, Jason and Caroline Zook, and we run Wandering Aimfully, an unboring business coaching program. Every week, we bring you advice and conversations to return you to your most intentional self and to help you examine every aspect of your life and business by asking, What is it all for? Thanks for listening. And now let’s get into the show.

Jason: And I’m here too. Hi. Hello, and welcome back to the podcast. How’s it going?

Caroline: I’m, like, kind of sound like Gingerbread Man a little bit.

Jason: Oh.

Caroline: We need to watch Shrek.

Jason: It’s a thong.

Caroline: We need to watch Shrek again. Also, I saw a clip of Shrek 2 going around somewhere, and I was like, I can’t remember the plot of Shrek 2, but I feel like it’s good.

Jason: Yeah.

Caroline: Was that the thing with the fairy godmother or something?

Jason: Maybe, but all I can remember about Shrek is with the last time we rewatched it, the animation was… you were like… we were like, Blongk.

Caroline: Yeah.

Jason: Blongk.

Caroline: It wasn’t great.

Jason: Animation’s come a long way. They’ve done a great job.

Caroline: Let’s watch the second one soon.

Jason: Okay, fantastic. That’s so great for everyone to know.

Caroline: Yeah.

Jason: Hey, welcome back to our podcast. Just wanted to remind you of our kind of new format. We do our Life in Portugal update at the end, so if you want to hear about that. Also, I’ve got some bad knee news to share.

Caroline: Wow.

Jason: Which is not fun.

Caroline: Bad news with a KNEWS.

Jason: But you’ll also get to hear about the Portugal medical system and how that kind of…

Caroline: In case you’re curious.

Jason: Worked out. So we’re going to have the chunk of the podcast, which will be the information, the thing, what are we working on, what are we going through? And then we have our new segment called Calm Business Confidential, where we share calm businesses that we’re finding so that you can learn about them.

Caroline: And we’re recording this before the first episode back has been released, so we have no idea if you hate it honestly yet.

Jason: Oh, right.

Caroline: We have also no idea if you love it.

Jason: This is true.

Caroline: So if you do love the new segment, be sure and email us and we will find out that riveting news on the next episode.

Jason: This is very true. All right, let’s jump into this week’s topic, which is us kicking off a… I mean, you round up to 30, but it’s a 26-day content blitz.

Caroline: We have a new project. It’s a content blitz.

Jason: Did you ever play NFL Blitz, by the way?

Caroline: Who are you talking to? Look at my face.

Jason: Yes.

Caroline: No.

Jason: Okay, well, you played Crash Bandicoot. You played Spyro the Dragon. These are all games around that era.

Caroline: Okay. Around that era. Let me take a step back. It is quite the mental leap for you to go from Spyro the Dragon. Great game, my favorite game. To NFL Blitz. Those are… The same person plays those?

Jason: Was, like, really silly. Like, you could be a hot dog as a character.

Caroline: Well, who knew that? That sounds cool.

Jason: The people who made NFL Blitz.

Caroline: What do you do?

Jason: You still had to call plays and do stuff, though.

Caroline: But you could do it as a hot dog?

Jason: You could be a hot dog. You could be a dolphin.

Caroline: That’s the whole game?

Jason: Yeah.

Caroline: Why?

Jason: Just because it was silly. It was dumb. There were, like, crazy things.

Caroline: Can we play that on our Switch?

Jason: I bet we could find NFL Blitz. You want to try it out?

Caroline: Do I need to know a lot about football?

Jason: I think you’d probably figure it out. I don’t know. We’ll look it up. It’ll be fun. Anyway, we’re doing a 26-day content blitz. So what does this mean, Carol?

Caroline: What does this mean? Well, let’s back up a step because we love taking people through the strategy. I think that’s why people listen, also, is they get ideas for their own business. They wonder why we make decisions. And that’s the fun stuff that I like to talk about. So where the inception of this idea came from is, first of all, we’re coming off of our content sabbatical, which we always take in the summers, and we are about eight weeks out from our Fall launch of our one product and offer, which is WAIM Unlimited, which is our coaching program. And in case you’re new to the pod, we launch that twice a year in an open and closed format for two weeks. And so the cadence of our business is very much sort of these spikes in the Spring, spikes in the Fall. And so usually we sit down about two months before a launch, and we say, What’s the idea? What do we want to do?

Jason: What do you want to do?

Caroline: What do we want to do?

Jason: That’s really how it starts.

Caroline: What do we want to do? We go, What’s going to make this launch different? What’s going to make it exciting? Yes, we totally could just turn it on and turn it off and do the same thing.

Jason: Which we have done for a couple launches.

Caroline: Which we have done before.

Jason: Especially last year while we were traveling full time.

Caroline: Especially last year when we were traveling full time. But we also, frankly, the amount of effort that you put in is the amount of effort that you get out, and we have the time and space. Also, it’s just a part of being excited about our own business. We want to have ideas. We’re ideas people.

Jason: Yeah. I think selfishly for me, too, as we were looking at this Fall enrollment, it was like, we haven’t really done anything to spice up a launch a little bit in a long time.

Caroline: No spicy launches in a while.

Jason: We’ve had almost zero spicy launches.

Caroline: And we haven’t done that much experimentation this year.

Jason: We haven’t created that much content.

Caroline: Exactly. So if you’re like, what have you been doing? Honestly, a lot, but not a lot outwardly. It’s been a lot of reinvesting in our community, reinvesting in infrastructure, in the product of our program, all of that. And so now we’re like, let’s do some outward marketing. So we sit down, we brainstorm, we go, what does this look like? Now, what I like about this idea is we also are big on going back to our yearly goals. What did we intend to do this year? Some of it goes off course, which you’ll hear about at the end of the year, but others of it we go, Okay, at the beginning, at the top of 2023, one of our big intentions was to revitalize our article content on our website.

Jason: That’s not true.

Caroline: What?

Jason: It was Narticles.

Caroline: Okay. Just so you know, those two things are synonymous.

Jason: Yeah, but it was called Narticles, which is a fun word to say.

Caroline: Right. So at the top of the year, our intention was to revitalize our article content by publishing new articles, which is a word that Jason likes to call, Narticles.

Jason: Oh, you got me writing the Narticles.

Caroline: Really? I go more to a narwhal place where I picture, like, a narwhal, like, writing an article. Yeah. Email us and let us know which do you like better? Do you like…?

Jason: Shrek or Elf? Is that what you’re asking?

Caroline: Yeah, exactly.

Jason: If anyone says Shrek, you’re wrong. I mean, really, it’s Elf.

Caroline: Okay. It’s Elf.

Jason: It’s incredible.

Caroline: Yeah. The answer is Elf. So we know that that’s important. Why is that important? Because what allows us to be able to take breaks with our content is the fact that we still have organic traffic coming from articles that are many years old at this point. And what we realized is behind the scenes, for the past many years, we’ve been creating content in the form of these coaching sessions. We’ve developed frameworks for teaching online business that only our WAIM members get. But what we haven’t done is extract some of that content and information in the form of public facing articles so that someone could go, What makes them different as business coaches? What are the things that they teach? And then they would find themselves in our program. Does that make sense? So it was really important to us to not just kind of refresh our articles, but also we wanted to feel like we could have some of these foundation articles to point people to in a public facing way.

Jason: So one of the things that I was thinking about when we were doing this Narticles planning at the beginning of the year was, we just don’t have a good place on our website that’s like, Hey, start here, and these are the things you should know about our core ethos, our core business advice, the way that we think about running an intentional business. These are the things. And part of that is because we migrated two websites, your previous website, my previous website, into Wandering Aimfully. So we brought over 400 articles, but we pared that down to 100 articles. But even then, those weren’t like the ideal articles. They were just existing articles that we had that we tried to shoehorn into this new thing. And we just, frankly, didn’t have the time. We didn’t make the time to write these new articles. And also, we didn’t know what we didn’t know. So by running a community, doing this business coaching for 44 months.

Caroline: A whole other business called Teachery.

Jason: No, but I’m saying but by doing 44 months of business coaching, I think we really discovered all the things that we wanted to say about business.

Caroline: Right.

Jason: We didn’t know those things four years ago, five years ago.

Caroline: Right.

Jason: Now, we know those things. And so it’s really important to, I think, also realize if you’re someone listening to this and you have a website with maybe some hodgepodge content like we did, and maybe doesn’t feel super streamlined, you might not be in a place where you know what that streamlined content is.

Caroline: Yeah. And I think also if you’re someone who’s still very much on the… Let’s call it the daily content hamster wheel of like an Instagram or something, you’re probably coming up with tons of content ideas, frameworks, processes, things that you’re sharing with people, but you’re doing it in such an ephemeral way that you’re never taking the time to translate that into a more evergreen piece of content that can stand the test of time. And this could be your opportunity to do that. And I always think about it like, are you creating rabbit holes for people to go down? And we do have plenty of rabbit holes. Like people often say…

Jason: People end up down some rabbit holes.

Caroline: They often say, like, they’ll find this YouTube video and then they’ll go to the podcast and then they’ll read some articles. But I want to create an article rabbit hole where it would be a very easy thing for someone to click around to and go, Oh my gosh, I just got a ton of value. Let me sign up for their newsletter, let me join their program, et cetera.

Jason: So let’s talk about the two strategies behind this 26-day content blitz. Actually, I think there’s three strategies.

Caroline: Great.

Jason: So the first one is, I’m just going to go to our core belief that still exists when it comes to creating content is, yes, if you need to move quickly, social media is the place to go. But if you don’t need to move quickly like us, or if you’re an established business owner who’s been doing this for a while, or if you’re just someone who understands like, you know what, I don’t have a good foundation of my content.

Caroline: Correct.

Jason: This 26-day content blitz for us is going to give us 26 new articles, Narticles, on our website that capture 26 fundamental ideas about how we believe you should run an intentional online business.

Caroline: Yes, sidebar because I literally just wrote the framework for the content strategy video and I didn’t have a way to explain this before, but now I kind of do. I’ve been using these terms ephemeral and evergreen and this is how I’ve been thinking about content is anything that lasts like maybe a day or even a week, which is like your Instagram posts, most of probably your TikToks, your Instagram stories, those things, that’s the ephemeral category, it has a place in your business for sure. But the evergreen category is something that has, you know, people can discover that content weeks, months, if not years after the fact, which is articles, which are YouTube videos, which are these even podcast episodes years beyond. And so I think that a healthy business has a content strategy that incorporates both because of what you were just describing, which is a lot of people focus on social media and ephemeral content because it gets them an instant gratification quicker, and they can see the numbers grow, and it’s kind of lower barrier to entry. And so people get in their audience. But if you never have the other side of that pendulum, which is the evergreen content, the deeper rabbit hole for someone to go down, the more valuable, the deep dive, if you will.

Jason: Search indexable.

Caroline: The search indexable. What happens is if you only have ephemeral, you have to stay on that quick flywheel all the time. And the reason that we’re able to take off two months in the summer and one month over the holidays in the winter season, so we’re only creating content nine months of the year. The reason why we can do that is because we have all this evergreen content that still lives on and the flywheel gets perpetuated even when we step off of it.

Jason: Great. So thank you for the sidebar. So, part of my three pronged strategy here. So we have that evergreen content value, right? The second strategy is a discoverability content strategy. So we’re going to use YouTube. So we are going to… along this 26-day content blitz plan is to create a daily video that goes up on YouTube and an accompanying article. So the video is essentially the same content as the article, but they kind of serve two different purposes. The articles again are going to be on our website. They’re the experience. We’re going to create… It’s going to be like a one page, one stop shop for you to be like, Oh, this is everything in WAIM that I could learn in like a snapshot, a quick view. And you could just go through all those articles like a rabbit hole. But we do want some organic discovery through a platform that has some built in kind of flywheels, if you will.

Caroline: Because by the way, if we only posted this as just articles…

Jason: Exactly.

Caroline: It’s not going to do anything for our launch because it would take so long for those organic search.

Jason: And also where would we share them? Because we’re not on Instagram, we’re not on any other social media. So they would just exist on our site and that would be it. So we’re using YouTube as our discovery platform. So having some discovery means that… And again, we’re expecting 300 to 500 views per video.

Caroline: We’re not trying to go viral here. We’re not expecting thousands.

Jason: But when you do 26 videos and you do a daily video and we’re going to talk more about our experience with 30-day challenges and why we like them and what they do, this is a great way for you to go. I don’t just publish one video and cross my fingers and hope that people like it. It’s like, no, we’re going to put out 26 videos and one of them will probably do well enough better than the others. And even if that was the one video that we published and it was the only thing we did, great, but we probably wouldn’t have gotten to that video without doing all the other ones.

Caroline: Yeah, which I think is a good segue into why we like 30-day challenges.

Jason: Not yet, because I have my three pronged strategy. I know you really don’t want…

Caroline: Was one of those a prong? I got off track. What are the prongs?

Jason: So the prongs, the first was having the foundational evergreen articles so that you have this content that is search indexable lives on forever. You talked about your ephemeral versus evergreen.

Caroline: Yes.

Jason: You side tangent perfectly on my…

Caroline: On your prong.

Jason: The second one is we’re using this project as a discovery. So to get some YouTube traffic to our site, to our launch, new people to find us.

Caroline: There is a chance for new people to find it.

Jason: And immediately.

Caroline: Immediately.

Jason: So right away, people finding these videos. Right.

Caroline: Not finding an article six months later.

Jason: The third pronged approach that I’m actually very excited about is, right now, when you land on the Wandering Aimfully website, it’s so difficult to find out what our best stuff is. If you go to our articles page, a lot of that stuff is older. A lot of that stuff is super in depth. You really have to wade through the waters to find a very quick answer. And I’m not trying to give someone a ten second story about business, but I’m so excited for us that we’re going to have this new landing page for our articles that we’re going to say, Here’s 26 pieces of content. You could probably tear through and read all of these in like 2 to 3 hours. And you would have a breadth of information from us. And it’s really our top level best information.

Caroline: And you would know, this is why I love it. Almost like the third prong is like a branding play. It’s almost like you would now know, where does Wandering Aimfully sit in the landscape of business coaches? You have a very good idea of what we’re about, what our ethos is, what our frameworks are. And so to just recap Jason’s prongs.

Jason: My three prongs.

Caroline: Your three prongs. It’s really about long term, short term. Well, I’ll say this. Long term discoverability, short term discoverability, and almost branding.

Jason: Yeah. And almost like an immediate someone gets to our site and knows exactly who we are and gets value. So it’s different than just having…

Caroline: Immediate value.

Jason: A well…

Caroline: Branded website.

Jason: Branded website and good copy and even like a good lead magnet. That is helpful. But this is 26 pieces of content that I can’t wait for you all to see if we make it through to the end, which we’ll talk about.

Caroline: Because jury is out.

Jason: On if we’ll make it because we’re not there yet.

Caroline: Strategy is great. Execution is equally important.

Jason: Anyway, so that’s kind of setting the stage for what we’re doing. And if you want to hear about this more week by week, we are going to share on the podcast as we go. But we’re also going to share in our newsletter. Kind of like a real behind the scenes look at the tasks that we’re doing, how we’re managing this project, the ups, the downs, all of that. So make sure you’re on our newsletter, wanderingaimfully.com/newsletter, so that you can get in your inbox every week a behind the scenes look at this Narticles project.

Caroline: Great.

Jason: And you’ll get to see some sneak peeks of the branding of the project because the project has its own little brand that you’ve come up with that’s fun.

Caroline: Have I come up with it yet, Jason?

Jason: Well, yeah. I mean, we know what it is. We know the concept.

Caroline: We have a concept.

Jason: Yeah, we have a concept.

Caroline: Still have to design it.

Jason: You haven’t drawn the dog yet, though.

Caroline: Haven’t drawn the dog yet.

Jason: The dog is still… We’re getting there, you know.

Caroline: People are like…

Jason: The dog?

Caroline: And that’s why Jason exists to just plant just weird stuff in your brain.

Jason: Plant a weird thing in your brain. Okay, let’s talk about our history of 30-day challenges, why we like them, why we don’t like them.

Caroline: Okay. Well, before I forget the point, what I was going to say before about why I love 30-day challenges is it kind of puts you in a place where you’re forced to create a higher volume than you would ever do otherwise.

Jason: Right.

Caroline: So my history of 30-day challenges, I mean, it goes way, way back, but the most prominent one is probably when I was doing my lettering challenges. So for those of you who don’t know, many years ago I had my own brand. It was sort of this like art and personal development brand and design called Made Vibrant. And for a while there, my thing was hand lettering. This is like in circa 2013, 2014 Pinterest hand lettering era of like calligraphy pens and stuff like that. And I was posting my art on Instagram, and I wanted to develop my own lettering style. And so I would do these 30-day challenges of like… It really all started with like, I’m going to do 30 days of movie quotes in my own hand lettering. And that was the impetus for getting in this daily habit of doing a piece of art and posting it. And over the course, I got so much volume in that I never would have had if I had posted once a week, once every other week, blah, blah, blah, blah. I just had the repetition over and over and over again. And that type of volume, you end up developing your own style, your own voice, your own brand. And I think so many people are trying to intellectualize what their brand is, what their content looks like, what their thing is, their unique point of view and they just haven’t gotten through enough repetitions to get to a place where they can start to see patterns and develop a voice.

Jason: I think the most important thing that 30-day challenges do along with all that is it helps you get over imposter syndrome. It helps you get over self doubt about your work.

Caroline: Because you know you just have to create one tomorrow.

Jason: You have to create tomorrow. If you want to go back and see some of the most cringy 30-day challenge content you could ever see, go find my I Wear Your Shirt YouTube channel, sort those videos by oldest, find my very first video on January 1, 2009. That video is awful.

Caroline: Very.

Jason: And I hated that video even while I was doing it. But I knew, guess what? Tomorrow, I got to post another video. So who cares?

Caroline: And maybe you get a little better.

Jason: And then I’m just like, I don’t know what I’m doing so I’m just going to start. Second video. Okay, I’m a little better. By the 30th video, it’s still not great, but I’m better at doing it. Again, for me, that was 2009. So that was like super early on in my journey through creating content. But fast forward from there and I had created tons of other content challenges, whether it was creating 30 blog posts in 30 days, writing 30 newsletters in 30 days, even like fitness challenges or things like that. I think the challenge aspect of any difficult thing that you’re not naturally really good at, it really helps you get through from a I’m nervous, I don’t know how to do this, to by the end of it you’re like, oh, I am better at this thing.

Caroline: Yeah, that actually reminds me of something that has stuck out to me recently. I was watching, I think it was an Ali Abdaal YouTube video and he was talking about what he has a program about helping people get started with YouTube part time and he talks about one of the concepts being get started, get good, then get smart. And so I really like this idea of the first few videos that you’re creating is just about getting started. The whole 30-day challenge thing is what you just said, which is it’s just getting over the impostor syndrome of creating something, of doing something. So it’s get started. Then there comes a point where you shift into, okay, now I’m over the hump of creating. Get good. Meaning, and I think that’s what I was kind of talking about, which is get a little bit better each time. Develop your style a little bit more each time. Try to take lessons from each thing that you’re doing and apply it to the next one. And then his last thing is like, get smart, which is like, how can you make it more efficient? How can you take it to the next level? But with each stage, you’re focusing on something different. And it’s funny because it’s like even in a 30-day challenge, you can kind of go through those three phases.

Jason: Yeah, for sure.

Caroline: Where it’s like the first few are just about getting started. Then you’re trying to apply lessons to get good. And then by the end, you’re really thinking about process and getting smart.

Jason: There’s a huge life hack to me when it comes to 30-day challenges, which is ignoring all the things that you constantly distract yourself with from doing the work. Because if you do a 30-day challenge, let’s just say you’re a person, you’re like, I’m going to do 30 reels on Instagram in 30 days. Never created a reel before. I’ve obviously seen tons of them. What happens is before you start creating those reels, just in the way you exist on Instagram now, you watch a lot of reels and you’re like, Oh wow, this was really good. Like, oh, I could never do this. Yeah, that person’s probably created 100 reels by the time you’re seeing that one that you think is really good. So of course it’s going to be really difficult for you to see yourself making that reel, right? So if you start a 30-day challenge to make reels, guess what? On the first day, you’re going to feel like, there’s no way, this is terrible, it’s whatever, but you know what, I’m committing to this. I’m going to do it. The second day, you’re going to create another one. Third day, you create another one. By about the 7th day, what’s going to happen is you’re going to stop looking at other people’s reels. It’s going to break the habit of you of getting stuck into comparing yourself to other people because you know that tomorrow you have to make another one and you’re going to want it to be a little bit better. And I think this is a really interesting kind of like, life hack for people who might get stuck consuming and not creating because this breaks you out of that cycle because, you know, oh, I’ve got to create another one tomorrow.

Caroline: I don’t have time to doubt myself because I’ve committed to this process of creating. I absolutely agree with that. And the other thing that I wanted to point out is our content blitz is like a little bit different because we are going to batch to some degree. From the viewers perspective, it will be a 30-day kind of challenge. From our perspective, we’ll be kind of bout creating some of the things, but a lot of this still applies, which is that we don’t have time to doubt ourselves, really. But the thing I wanted to say is another reason, going back to the strategy of it all that we wanted to try and experiment with daily leading up to the launch is I have this theory that, you know, we’ve watched some YouTube content that’s in a daily format. One that easily comes to mind is Ryan Trahan’s Penny series. And Jason and I both remember last summer watching his Penny series. He did it for 30 days. This year he did it for seven. But last year he did it for 30. And it became a part of our daily routine.

Jason: Exactly.

Caroline: Where we would come back from the gym. We were in Scotland at the time. We would be like, you want to watch Ryan? And we would watch his videos. And it became something we looked forward to every day. And I have this theory that let’s test that for our own audience. Do people come back? Do they start to incorporate it into their day? Do they sit down with their coffee in the morning and watch our short… They’re going to be short videos like five minutes, five to six minutes long. Do they sit and kind of that’s what they do in the morning? Do they end their day with it? Do they sit down with lunch? Where does it fit into their day?

Jason: I think this is why any consistent daily thing is a very intriguing business model because it’s exactly what you’re saying. It builds into people’s routines. So it’s why like the Morning Brew newsletter.

Caroline: Right.

Jason: Sampar’s the Hustle newsletter, like all these things that are like daily things. When it builds into your routine like that, it just becomes something that’s like, oh, I have to have this every single day. And so I do think you’re right. We’ve talked about this. I think it’s going to be very interesting to see, in a 30-day challenge, a lot of what you… If you’ve ever done one, you see there’s a real wane in people’s attention by the 10 day or 14 day mark, but then it starts to pick back up towards the end. Now, obviously, if you’re doing something super interesting, like a Ryan Trahan YouTuber.

Caroline: Right, that makes sense.

Jason: You’re always interested every single day because it’s very different. But like a content 30-day challenge with business content specifically. Or info content. I think it is a little bit less exciting towards the middle, but it will pick back up towards the end because people are like, okay, well, how’s this going to end? I’m getting back into it.

Caroline: Yeah, that actually just thinking out loud as you say that because there’s no real narrative arc to this, though I don’t think that will necessarily be the case. I think it will because they’ll know the launch is coming. So I guess that’s really the narrative arc is you’re not really building towards any conclusion except for the fact that the launch is coming. So I wonder if there’s a way for us to build that in. But remember, the primary purpose of it is for evergreen. You don’t want to create some sort of…

Jason: Expiring…

Caroline: Exactly.

Jason: Thing. Now, one thing we could do is we could tell like a 26-word story through our videos. It’s like a hidden story and you have to… What’s the final word at the end? Because otherwise, the story is not going to make any sense.

Caroline: That’s silly. We should do that.

Jason: No, it’s too much work. Okay, so I think that’s a good history of our experience with 30-day challenges, why we like them. Maybe let’s talk about why 30-day challenges aren’t a good idea and what the pitfalls of them could be for some people who are starting out with it or maybe trying to do it. I just think give the other side of it for a second of like…

Caroline: Okay, yeah, it’s a shit ton of work.

Jason: Yeah. This is the part of this where I just want to be honest with people because I feel like it’s very easy to go, Hey guys, sit down, do a 30-day challenge, write 30 articles, or create 30 videos, or create 30 Instagram reels, create 30 newsletters, create 30 podcast episodes. You can do it. Rah, rah, rah.

Caroline: Yeah, there’s a reason. Well, it’s kind of funny, right? Because again, another thing that born… That was part of the inception of this idea was the fact that not a lot of people do a daily lead up to a launch anymore. And it’s because it’s so much work.

Jason: It’s so much work. Yeah. So what I want to point out here, I think it’s two things. Number one, there’s two different ways to kind of do a 30-day challenge. So the way we’ve pretty much done all of them in the past is real time.

Caroline: Real time.

Jason: So it’s like we’re creating, we’re releasing, we’re documenting all every single day. This one is very different. We haven’t done one like this before where we’re essentially doing it a month ahead of the release of the first one.

Caroline: Right.

Jason: So as of recording this, we have done some planning, we’ve done some tasks, we’ve started creating some of the skeletons of the content and then next week we’re going to finish that and then the week after that will be like, our production hits the ground running. The week after that will be our editing of all the production hits the ground running, and then we should be done. And then the release will start and we should be done with everything. I think there’s something really interesting there. If you’re going to think about a 30-day challenge, are you doing it real time or are you doing it batched ahead of time? And you’re giving yourself enough time to then… I have this release schedule where all I have to do is hit publish or whatever that is.

Caroline: And that was really important to us also because, remember, this is on top of a launch that we’re already doing. And so we just knew that needs to be our first priority. And so this is the pre marketing for the launch. And if we were trying to do it in real time as we were getting ready for the launch, it’s just a recipe for disaster.

Jason: My second thing about 30-day content challenges, and again, ours is 26 days, so it doesn’t have to be 30 days, but any amount of time. And I think this is what we dealt with yesterday or the other day, which is if you’re doing this by yourself, you’re going to fight a lot of mental gremlins on your own. If you’re doing this with someone else like we are, you’re going to run into what we ran into, which is like you have two head chefs in the kitchen, and it becomes very difficult because you both have a vision, you both have ideas, and maybe not a lot of people can relate to this because they don’t necessarily work with a partner. But if you do, one of the things that we find is, like, you just really have to pick a head chef for different parts of the thing. So for us, when it comes to writing the scripts for the videos, specifically, I just defer to you. You’re the head chef. And you need to be because, if I’m partaking in that, it’s just going to cause friction.

Caroline: You’re just slowing me down, man.

Jason: Exactly. But it’s the same thing when I’m filming the videos or recording or editing the videos, I don’t necessarily need your input. I just need you to trust me that I’m going to put us in frame, we’re going to sound good, we’re going to put things over top of the video in the edit, and I don’t need you to sit next to me when I’m in Final Cut because you’re going to slow me down. Like, just let me do my thing.

Caroline: Totally.

Jason: Of course, at the end of it, we’ll review everything together and we’ll make sure that everything is signed up and agreed upon.

Caroline: Same way that you review the scripts and I review the final product.

Jason: Exactly.

Caroline: But you’re not in the process.

Jason: But if you’re a solo creator doing this and doing a 30-day challenge, I think the biggest piece of advice that I would give you because we’ve both done these solo things, is don’t second guess it. Know that tomorrow is another day, that you’re going to have to create a thing again and just be okay with the fact that good enough is better than not doing anything at all. And it’s that classic, like, done is better than perfect. Pretty much everyone’s 30-day challenge they’ve ever done, half of it they’re probably not happy with. Maybe more than half of it. But there is a part of it where you have like a couple of nuggets that you’re like, oh, I’m really proud of that one.

Caroline: And the cumulative result of all of it is what you’re looking for, not the banger of any individual piece of it.

Jason: Which for us, when we think about these 26 videos, when I think about it on YouTube, if these things all get 500 views per video, that’s 13,000 extra views of our content that’s specifically related to things we want to talk about on YouTube.

Caroline: You’re so good at quick math. I was like, those numbers don’t even make sense. How would you know? And then I was like, oh, it’s 500 and that’s 1,026.

Jason: Okay.

Caroline: But man, did that take me so much longer than what you just did.

Jason: But think about that, right? Like 13,000 views on YouTube, that’s great because we’re a small channel. We’re not trying to be a big YouTuber. We’re not trying to compete with the millions.

Caroline: And it’s like, could that lead…?

Jason: If that’s 13,000 really good highly qualified eyeballs of people…

Caroline: Right, and of course, there’s overlap but I’m like, Do I think that 13,000 extra views of someone interacting with our valuable content and our personalities could lead to, let’s say 50 additional sales of our program? That seems possible.

Jason: Yeah, absolutely.

Caroline: And is that then worth it?

Jason: Exactly. And so I think that if you’re thinking about doing a 30-day challenge of any kind, if you’re thinking about kind of following us as we’re doing this, know that there are outcomes that you can’t see, there are outcomes you can’t quantify. You’re not going to know, Oh, all right, fine. I’m going to get on TikTok and I’m going to start with 30 videos and I’m going to pre record them and I’m going to upload and whatever and maybe I’ll get 500 views or 1000 views. You’re not going to know what those numbers are, but just know that the cumulative value of that thing is exponentially better than just like one piece of content created randomly.

Caroline: Totally.

Jason: And so I think that this is a great way just to understand it’s a lot of work.

Caroline: Exactly. Go into it knowing it is going to be more work than you’re used to. That’s why we use the word blitz. We still have good boundaries. We’re not going to sacrifice our health or our marriage or any of that stuff. But do we know going into it that it’s going to be more of a work focused for weeks? Absolutely. And that’s the way that we operate our business is very much sort of throttling at different times, and that works for us.

Jason: Do you remember off the top of your head the total amount of hours that we have allotted for this?

Caroline: 40.

Jason: No.

Caroline: 80.

Jason: Yeah. So we think this project is going to take us 80 total hours.

Caroline: I think the 40 because that was like each of us.

Jason: Right.

Caroline: Because the thing that kept in my head was four weeks, 40 hours, which was like each of us 40 hours.

Jason: Which, when you think about it, when you’re like, hey, 80 hours to create 30 pieces of content, YouTube videos plus articles. That’s not like crazy amount of work, right? That’s like two full 40 hours work weeks. But we are managing a bunch of other stuff so we can’t do it all in two weeks. We have other things we have to keep up with. But I do think it’s interesting when you start to break down the numbers, which is the next email that’s going to go out to our email list is how we’re breaking this down.

Caroline: And we already realized based on starting this project, that…

Jason: It’s going to be a little bit under, like we’ve guessed under.

Caroline: Exactly. Because…

Jason: 100 hours is probably a bit more fair.

Caroline: Yeah, probably over.

Jason: 140 hours.

Caroline: Actually, that reminds me, before we send out that newsletter, we should sit down. Let me do today’s scripting, and then let’s readjust our time estimates.

Jason: Plan out in real time here.

Caroline: And then let’s include the actual estimate in the newsletter.

Jason: Do you have any meetings you want to go over while we’re here?

Caroline: When do you want to go renew the car?

Jason: Great. All right. So that’s our 26-day content blitz. We’ll keep you updated in future episodes of the podcast. Like I said, if you want kind of the week to week real time, wanderingaimfully.com/newsletter, so you can kind of follow us along there. And then our YouTube channel, again, the first video will go out September 18. So that’s youtube.com/wanderingaimfully. If you want to go ahead and subscribe, you’ll actually get some fresh YouTube content from us for…

Caroline: We still need to talk about… Yeah, we need like a little update video so that all of our travel people are like, What happened?

Jason: I just say we just drop it on them. Let’s just go. All right, let’s move into our new segment started last week.

Caroline: Oh, I’m so excited.

Jason: To pretty solid fanfare. And by fanfare, it was what Caroline said earlier, which is we don’t know because this podcast is being recorded before that video goes live.

Caroline: Absolutely no idea.

Jason: But it’ll be fun. All right, let me get my notes. Do you want to go first this week?

Caroline: Well, let me… Let me, in case anyone did not listen to last week, let’s just give a quick overview. This segment is called Calm Business Confidential. We’re going to work on the sting, and Jason and I wanted to add this segment because we think it’s fun to feature business ideas that are not million dollar or billion dollar business ideas.

Jason: They can be million dollar, but we’re trying to keep it… Our parameters are under one and a half million dollars in annual revenue.

Caroline: And also because there’s so much business inspiration content out there that are, like, trying to be the next TikTok or whatever. No, most of you listening are just people who want to create businesses for the possibility of becoming financially secure, having a flexible business, not answering to anyone but yourself, and you just want to live a good life. And that’s probably why you interact with our content. And so we thought it’d be fun to whenever we come across, like, fun business models or someone who’s doing that, they seem to have a business that is allowing them to live a good life. It’s calm. It’s not managing teams of hundreds of people. It’s just like, do you have a calm business? Cool.

Jason: Also, just want to mention the business doesn’t have to be a million dollar business. I think sometimes we will talk about businesses that are in that range, but sometimes the businesses will be less. Like last week, my feature, I don’t think she’s making over $100,000 even close to that yet. And so I think we’re going to have some examples that are bigger, that are smaller. Some of them are not going to be calm to start, which is going to be an example of mine this week.

Caroline: Interesting.

Jason: But they’ve gotten to a calm place.

Caroline: What a teaser. Also, I do think I completely neglected to say last week’s, like, just how much money she made or the fact that she was able to have her fiance quit their job and come work for her. Anyway.

Jason: Yeah.

Caroline: So we’re going to learn as we go.

Jason: All right. Are you starting or do you want me to start?

Caroline: I think I started last time. So you start.

Jason: I think I started last time.

Caroline: Great. I’ll start.

Jason: Great.

Caroline: Okay, so let me set the scene.

Jason: Yeah.

Caroline: A year ago, I had this idea while we were traveling that I wanted to create a secret Etsy business and not tell anyone so that we could then sort of one day be like, Oh, I figured out…

Jason: I cannot wait. This is going to be so exciting for me for you to say, I did it.

Caroline: I’m the calm business.

Jason: Let me introduce you to my secret bank account that has $40,000.

Caroline: Because you know what I figured out very quickly? It was I was like, I’m having a hard time keeping up with our original businesses while we were traveling. So it was a no for me. However, I did go down an Etsy rabbit hole.

Jason: Nice.

Caroline: And I found this creator by the name of Tim Koa. Okay. I found his YouTube content because he was talking about Etsy. There’s a theme here which is that I get a lot of my business content from YouTube.

Jason: Yeah, it’s great.

Caroline: And so he started an Etsy shop called Turtle Tags.

Jason: Cool.

Caroline: Do you know what Turtle Tags is?

Jason: Never heard of it.

Caroline: Okay, so Turtle Tags is an Etsy shop that creates daycare and school stickers for kids. So it would be like a little illustration with their name, right? So it’d say like Jason and you get like a sticker sheet and you can put it on their cups, their pins, their everything because he was finding that he was a new dad and playdates and stuff, all their stuff was getting mixed up, right.

Jason: Gross.

Caroline: And so I know this is a little weird because technically it’s a physical product business because he’s shipping the stickers, but I do think we have a lot of listeners who are interested in Etsy and so I hope that this will be a little bit inspiring for them. So first I’m going to tell you how he came up with the idea because I think that’s interesting. Then I’m going to tell you how much his business made… has made. And then I’m going to tell you why I think this business is interesting in general, okay? So he first came up with the idea, like I said, when he noticed that his kids stuff was getting mixed up. And then he went to go look for stickers with his kids names and they were all so ugly. They were not well designed. However, all of these Etsy shops had like a ton of sales because you know on Etsy you can see how many sales. And so he was like, okay, there’s all these shops that have these sales, but none of them are well designed at all. And so the nugget of wisdom there I think is you have market validation. So you’re seeing that there is a market for customers for this, but you have an immediate differentiator, which is he’s a designer.

Jason: Right.

Caroline: And so he’s like, if I just make these illustrations like cuter and better, that’s my built in differentiator and I can do this better, right? And so I think that’s a good combination for a business idea is market validation. But you know exactly how you’re going to do it differently. And then you might be wondering like, how much money did he make? Well, he launched his shop Turtle Tags in August of 2020. And from August to December he made $2,000. Okay.

Jason: Great start. Made money, good job.

Caroline: He made money. But that’s a side project. I think a lot of people would be like, yeah, if I could make 2,000 extra dollars, that would be great. But then in all of 2021, he made $43,000.

Jason: There you go. Nice.

Caroline: And I mean, that is a really hefty nice side project or full time project for someone.

Jason: That’s a lot of Turtle Tags.

Caroline: That’s a lot of Turtle Tags. In 2022, his sales were slightly down. He made $34,000 on Etsy. And then he launched his own Shopify site so that he could sell it on his own, which I think is also good business sense, just in terms of…

Jason: You own more…

Caroline: You own more of it. You’re not at the whim of it. A lot of copycats started popping up.

Jason: Turtle Tagging. Tortoise Tags.

Caroline: But then I think what’s really cool is he started realizing, let me document my journey. And now he has a YouTube channel, which is then an additional revenue stream. Right, because you have AdSense. And so the thing that really why I wanted to feature his business is because I watched one of his kind of business recap videos, and he very much lives the calm business ethos, which is, I do this because I want to spend time with my family. I want to make a little extra money. I think he honestly has stopped making YouTube videos, which I think is such a plus because, to me, it shows me that his business has evolved. And he’s not just beholden to this content machine. He’s in control of his business. He’s deciding whether he wants to throttle it up or down. And I love his little website. So why do I think it’s interesting and why did I want to share it? I think there’s a lot of people out there that think about these platforms like Etsy or even think about launching a podcast or doing whatever, and they think it’s so saturated. Like, I’ve missed the boat. And I wonder if you listening right now, have thought that about something. You’ve had this idea and you’ve gone, it’s too late. Like, Etsy has already popped off. Podcasts are already whatever.

Jason: Saturated.

Caroline: And it’s like, I see new people launching podcasts, popular podcasts all the time, and it doesn’t matter. It really doesn’t matter. If anything, you need to look at these platforms. Like, yes, be strategic about where you go, but if you have an idea, I think there’s still room for you.

Jason: Turtle it. Yeah, turtle it.

Caroline: Turtle it. Turtle Tag it. And then I also think it was really interesting that that first few months, those four months, he made $2,000 and he didn’t stop. You know what I mean? He didn’t go, Well, that’s not enough money to really make an impact on my life. He was like, No, people are buying this. And also, with a very low price product, $2,000 is not nothing. You know what I mean?

Jason: Yeah, exactly.

Caroline: The volume that he had to do.

Jason: Actually, the margins are very good because it’s not that expensive to print some stickers.

Caroline: And then he got better. He added new listings. He learned what worked, and he just kept iterating. I love the idea of scratching your own itch. Like, knowing that you had a problem, and so you’re very intimately acquainted with your customer because you are your customer. And then I think a lot of people forget that documenting your process is a great content strategy. I think he purposely said he didn’t document it because he wanted to see what the business would do on its own. But then when he added the YouTube element on top of, like, that was really smart. And it also opened up a new content or a new revenue stream, which is great. And then, like I said, I just love the fact that he kind of lives the calm business ethos and that, you know, his business is evolving with his values and where his time wants to go and that he’s clearly not trapped by this business, which is the whole point of sharing these stories.

Jason: Tim, great job with Turtle Tags.

Caroline: Tim, great job with Turtle Tags.

Jason: Great find. Great find.

Caroline: Thank you.

Jason: All right, I have a SaaS company that I am featuring this week.

Caroline: Okay.

Jason: And you know of this SaaS company. You know some of their story, maybe not all of their story. So I want to talk about Marie and Filip of Tally.

Caroline: Go ahead.

Jason: So Tally.so is the URL, and Tally is basically like a Typeform competitor. They’re a form builder, if you will, very much Notion inspired. So let’s go back in time.

Caroline: Wait, I think that’s an important point because you’re saying very much Notion inspired, but they’re a form builder, and Notion is not a form builder. So their kind of special sauce is that you’re building forms like Google Forms or a Typeform, but you’re doing it in an interface that is very block focused like Notion.

Jason: Yeah, exactly. Thank you.

Caroline: You’re welcome.

Jason: So 2018, 2019, they were working on this other business idea. They’ve been working on a couple of business ideas over the years. Husband and wife team, by the way, which we love.

Caroline: We love a husband and wife.

Jason: And they were in the travel influencer hotel space. And so they really wanted to be digital nomads. They wanted to create, like, this different business that did this thing. Well, something came around in 2020.

Caroline: Can’t think of what it is at the moment.

Jason: Basically destroyed this entire business model because no one was traveling. Hotels were like, we don’t have any money to spend on advertising because no one can travel. This business idea just, like, doesn’t work. So they found themselves in August of 2020 basically just being like, What do we do now? They had clients that were hotel clients. They were working with a couple of different people. All of it dried up. And so they basically were sitting there like, What do we do? What can we work on? And Notion at this time was, like, really starting to get some traction.

Caroline: Yeah, that was really the kind of first little uptick.

Jason: Wave of Notion besides when I told you about it in 2019 or 18, whatever. Terribly, I said this multiple times. I did not understand what Notion was when it was first created.

Caroline: So when he described it to me, did a very bad job. And I…

Jason: Also didn’t use it because…

Caroline: Never looked into it.

Jason: I didn’t need it. Anyway, so they were very inspired by that. They also started to see that Typeform, and all these other form builders were starting to get expensive. And they’re like, This doesn’t have to be that expensive. They also realized that Filip had created in 2014, a poll, a very simple online poll called Tally that was the number one Product Hunt Product of the Day when he released it, but he never did anything with it.

Caroline: Really?

Jason: Yeah. So they were like, this is probably our closest idea that we could start with, we could use. So they kind of went into MVP mode, which is Minimum Viable Product for those who don’t know in SaaS World. And they just started building, and they’re like, Let’s just build out this form builder. And by December of 2020, they launched on Indie Hackers. So they did, like, a release on Indie Hackers. They shared on Twitter, which is they were doing a build in public the whole time, like, Hey, we’re building Tally.

Caroline: Speaks to Tim Koa, the whole document your process. That’s a good opportunity.

Jason: They were showing their Turtle Tags, and they got a bunch of user feedback. So the product is free. It’s still to this day, it’s free to use. And then they have a paid tier.

Caroline: Okay. Freemium, we call it.

Jason: Freemium. They basically spent three months getting all the feedback from all the users that they gained from Indie Hackers, from Twitter, all these other things. And in 2021, they launched on Product Hunt. And they reached the $1,000 recurring revenue mark in 2021.

Caroline: Just on that day?

Jason: No, up to that point. So when they launched on Product Hunt, they’re like, Hey, we just hit $1,000 recurring revenue. We want to release this product to everybody on Product Hunt, saying it’s available for everyone. I see it was already available for everyone. But this is what you do when you’re running a product like this.

Caroline: Yes, this is a good golden nugget, which is create a story and a reason for people to be excited.

Jason: Yeah. So when people heard about this, it wasn’t like, Oh, this is brand new. I just built it yesterday. It’s, Oh, this has been around for a couple of months. We’ve iterated. We’ve gotten it to a point where people are paying for it. We think you would like it. So one of the things that I really love, that I’ve heard Marie talk about in lots of interviews is how scrappy they are at marketing. And so essentially, she would just spend, as most people already are, hours on Twitter every day searching for things like Typeform, Google Forms, people talking about building forms. And she would just jump in the conversation, and it wouldn’t be like, Hey, go try out Tally. It would say, you know, I’ve heard blah, blah, blah. Did you know that we have a free form builder? You can go check it out. It wasn’t always the first thing that she said. She also said that she would just DM people all the time and just ask if they’d heard of Tally, if they would try it out. It’s free to do… So I just love the scrappiness nature because I think a lot of people aren’t willing to do that type of work. But I think that type of work can lead to really tremendous results.

Caroline: You’re creating a groundswell.

Jason: Exactly. And you’re interacting individually one on one, where most especially software companies just don’t. They just try and build the content marketing engine and they never want to talk to people.

Caroline: I think also something that is a benefit of that scrappy method is there’s some type of network effects thing happening where if you pop into enough of those conversations, separately, those two people who have had micro interactions with you start to talk and they go, Maybe the topic of forms comes up and they go, Oh, have you seen that Tally?

Jason: Exactly.

Caroline: And then they go, Yeah, they DM’d me a while back, blah, blah, blah. And there’s something about the network effect of the social validation of two people both knowing that that person exists that then they go, Oh, they’re a bigger. You know what I mean? Like their name recognition.

Jason: A big part of this is what we’ve seen with Teachery’s growth over the years, which is, I’m the one answering the customer support.

Caroline: Right.

Jason: And so someone will say like, Hey, the founder answers the customer support and is a real person and doesn’t just send you a help doc. Will actually help. And people have joined Teachery saying like, I heard the customer support was so good, I had bad customer support in other places, so I want to try it out.

Caroline: Right.

Jason: So, mind you, we’re at the end of 2020, the beginning of 2021. They’re at $1,000 recurring revenue and they’re working just the entire year doing scrappy marketing stuff. By the end of October, they have passed about 15,000 free users on their platform and then they have enough paid users that they’re at about $7,500 in recurring revenue. So pretty solid growth, but nothing like crazy over the course of that first year. In January, they had a really big push to I think, like, start the year momentum and they added a bunch of features. They got really good at customer support and the feedback loop of features and whatever. They jumped up to $10,000 recurring revenue in January. So like a pretty sizable jump in like one month, basically.

Caroline: Definitely.

Jason: Then in May, they doubled their revenue. So May of 2022, they got to $20,000 recurring revenue. So this is where, like, it just starts to build. In October. So just five months later, they jumped another $10,000 to recurring to $30,000 recurring revenue.

Caroline: Wow.

Jason: But one thing that they said was they hit the 50,000 active users part. And again, this is a freemium model, so it’s a lot for users. They started to deal with a ton of spam.

Caroline: And we deal with spam in Teachery a lot too.

Jason: They had to basically slow down growth a little bit. They had to really focus on that.

Caroline: Infrastructure.

Jason: Exactly. And I think they did a little bit of hiring at this point because it was really just the two of them still doing everything. And then May of 2023 of this year, they passed 100,000 users using Tally.

Caroline: Wow.

Jason: To a total of $60,000 recurring revenue, which is $700,000 annual revenue. And that was five months ago now, or three months ago. So it’s probably more than that, but it’s just really fun. I love this idea started in 2014 as a thing that didn’t get off the ground.

Caroline: But really…

Jason: Ten years later, it evolved into a business that will eventually get to be a million dollar per year business started by two people, super iterative process, years of building and growing and listening. And this is the thing that I always come back to when people want to build a sizable business with sizable income like this. It takes years. And if you’re at least just willing to accept that fact and go, I’m willing to do the scrappy work every day. I’m willing to listen to users to get feedback on how to make the product better. I’m willing to iterate. This doesn’t have to be a software product. This could be any type of business. If you’re willing to do all those things, you can get there, but it will take years. And I love that that’s like, to me, the big takeaway for them. I’m so happy that in a crowded landscape of form builders, they’ve been able to carve out a business where they’ve captured 100,000 users. Granted, they’re free, but they’ve captured enough paid users that they now have a million dollar per year business almost. And I think it’s just really great. And it speaks to product led growth, to investing in your product. It speaks to great customer support and it speaks to scrappiness.

Caroline: Do you have any idea what the difference between… Is it just some premium features that separates the tiers from the free?

Jason: I think it’s removing the Tally branding as well.

Caroline: That’s a classic one.

Jason: I think the additional features you can have in the forms, it’s probably like the exporting of the data and things like that too. But it’s a pretty full featured free form builder, and I think that’s also a good thing for them, too, is like, most people with 100,000 users are using the free forms, but I think a lot of people probably are just like, this is such a good product, I’ll just pay the $19 per month for it because it’s so good. I’m happy to support this company. They’ve already given enough away for free. So I think it’s a really fun story. I love that story. I love the husband and wife team.

Caroline: I know. I want to go listen to more interviews because also just from the SaaS part of our world.

Jason: Yeah.

Caroline: We kind of, like, have one foot in both of those worlds. Right. The SaaS world and then kind of the course world, digital product program world.

Jason: All right, so that is Calm Business Confidential. If you have any businesses that you would like us to talk about that you think fit the criteria of a calm business, we’d love to hear about them. If you want to go to wanderingaimfully.com/contact, you can submit a business to us. We’d love to get their information. Think about the things that we’ve talked about here, the unique story, kind of where did it start, the arc of how it was built and some revenue numbers. We’d love to share that stuff because it’s just fun to kind of hear.

Caroline: And people at the helm who are not interested in building a billion dollar empire, they want to create a business that fulfills them and that fuels a really great balanced lifestyle. That’s really what we’re looking for with a twist.

Jason: I think a good takeaway for us with each of these Calm Business Confidentials is like, are we proud of these people telling their story? I’m so proud of Tim.

Caroline: That’s what I mean. I was like, I know it doesn’t totally fit because it’s just stickers or whatever, but I remember finding his video and I was like, yes. I was like, I want to know that more people out there doing this.

Jason: Exactly.

Caroline: Because I get jazzed up just as much as the next gal about big business and just like a Guy Raz, How I Built This. I love that. Okay, but…

Jason: Listen, the story of…

Caroline: Actually.

Jason: Patagonia is great, but none of us are creating the next Patagonia.

Caroline: Yeah. I don’t actually want to live that life. The truth is, I don’t want to manage a team of 100 people. I just want to be able to wake up in the morning, enjoy work that I’m doing, not answer to a boss, make good money where I feel financially secure, and live a good life.

Jason: Yeah. All right, so you’re going to start Terapin Tags, then?

Caroline: Tarapin Tags. The last thing I wanted to say… What was it? It just left my brain. What was it? It was Tally and SaaS and, oh, lost it.

Jason: All right, we’re getting into Postagal.

Caroline: Postagal.

Jason: This is the end of the podcast topic where we talk about our life in Portugal and just share some of the things. This week, it’s knee news.

Caroline: Knee News. Different than nuno.

Jason: Different than nuno.

Caroline: But knee news.

Jason: Nuno is a very common name here in Portugal. Knee News. So for those of you who don’t know the history of my knees, very, very quickly, I was a basketball player growing up for many years. 2007, I tore my ACL in my right knee but I had a pretty bad injury with it. 2008, I then tore my ACL in my left knee after fully rehabbing my right knee back to strengthening and being able to play basketball. Basically, kind of ended my potential to play at a professional level in basketball. Who knows if I actually ever would have made it, but I really was aspiring to try. And so since then, I’ve just had not great knees, kind of like old man knees. But I’ve been able to play tennis. I’ve been able to play basketball if I wanted to. They don’t feel great, but they’re not bad. Fast forward to we picked up playing paddle here in Portugal. And paddle, for those of you who don’t know, is like tennis with walls, smaller court, and it’s kind of fun. It combines like tennis and squash, or tennis and racquetball. And we played basically three times in the span of a week and a half. And I don’t remember ever at one point having something happen. Like when I tore my ACLs back in 2007, I knew that something happened.

Caroline: Right.

Jason: In the second one. I knew exactly what it was because I remembered what that felt like, and I remember what it felt like afterwards. This time around, it wasn’t anything that I felt. And actually, up in to that point, before we played, my knees were actually feeling the best they felt. Now, why is that? I haven’t been doing anything for a year while we traveled. I did no physical activity on my knees other than just walking every day of our lives around all these different countries. So I was getting enough exercise, but I wasn’t really strengthening my knees. And so I went into playing paddle, and I think I just overdid it on my 41 year old knees.

Caroline: You overdoing it. Interesting.

Jason: And this is about, like, three to four weeks ago now, and I still have pain every day, and it’s, like, hard for me to walk. Well, I got an MRI, which, by the way, I’ll just share with you, for those of you who’ve gotten an MRI in the US medical system, speaking specifically from my own personal experience, first of all, it’s always like three to four weeks at a minimum booked out before you can get one.

Caroline: Right.

Jason: Even with good insurance. I paid one $1,800 out of pocket each time I got an MRI, so I had insurance, and it cost me one $1,800 to get the MRI. Now, that’s not the case for everybody, but it was for me and whatever insurance I had. Here in Portugal, we have private health insurance, and it costs us $1,500 per year for both of us, per year. Our insurance when we were in California was $1,500 per month. I got an MRI scheduled, and it was two days from the time that I wanted to get it done, which was amazing, and it cost us €65. Incredible.

Caroline: I don’t understand.

Jason: Incredible.

Caroline: That doesn’t compute.

Jason: So I went in, I got the MRI, and we were kind of told, like, Oh, the results are going to be a while later. Also just to kind of share the Portugal…

Caroline: Well, that’s what I wanted to share because I don’t know if people might find this interesting. I know one of my big question marks before we moved here was, What is the medical system like? What is the experience like? Also, I’m already someone who in the past has had a little bit of health anxiety, and so medical stuff just makes me nervous. And so I was like, Am I going to be ten times more nervous going into a medical environment where I don’t speak the language? I don’t know what the customs are of how it works and everything. And we’ve had enough medical interactions now that I feel like I can share a bit of what that experience has been like. And spoiler alert, it’s been fantastic.

Jason: Yeah, I mean, you find that pretty much at every medical office we’ve been to, people speak English, which is wonderful and helpful. We have found that everyone’s been…

Caroline: By the way, not… Some people speak English. So I want to paint an accurate picture, which is it’s not like you walk in and everyone’s just like, Oh, speak English. It’s like, no, sometimes you probably especially like, maybe receptionists might not speak that well. Usually, at least one of them does.

Jason: Exactly. There’s two receptionists, maybe one doesn’t speak English.

Caroline: Right. The nurses that we’ve all had have spoken English, which I think is very helpful. I’ve had a few doctors who speak different levels of English, but…

Jason: It’s always enough.

Caroline: It’s always enough. And I always go with the first one, like my top doctor that speaks English, but then if I need to go in for an appointment, they’re like, Oh, she’s off today. Can you see this other doctor? And maybe they don’t speak as well. But I’ve never yet felt like language was a barrier to getting good medical care, or that I felt overwhelmed or I felt like I didn’t know what was going on. I have not felt that.

Jason: Yeah, I mean, the MRI situation for me was perfect. Like, the technician who basically did everything, he spoke English, but then the person who was basically assisting him and putting my leg in the thing or whatever, she didn’t speak any English. So she was just like, Tudo bem? Tudo bem? And I was like, Yeah, it’s good. Thank you. That’s fine.

Caroline: Tá bem. Tá bem.

Jason: Sure.

Caroline: Tá bem means also…

Jason: Yeah, also your other one. Sure, let’s do that one. So, yeah, that experience is pretty good. I will also say I do want to mention we use a service that’s called Serenity, which is like a medical concierge service, but it’s extremely affordable. Again, compared to the US medical system, it’s €300 per year. And again, if you factor in the fact that we only pay $1,500 per year for our insurance. It’s a no brainer to add this on because we were paying $1,500 per month previously. But they’ve been super helpful because they help set up all the appointments, they help find the doctors, they help do the research, where when you’re in a foreign country, that information is almost invaluable because you don’t know anything. And even in the States, I was thinking about it when I would have these injuries, I was just googling things. I was picking doctors literally out of nowhere. It would be the same thing if we were here. I’m so happy we have this service because it takes all the guesswork out of it. And you have someone who’s on your team who can help you.

Caroline: On your team, exactly. I think part of the added anxiety of dealing with health issues is feeling like you have to be your own advocate. You have to do all your own research. You’re on an island by yourself. You have to be like…

Jason: You’re already stressed out because something’s wrong.

Caroline: Exactly. And then it’s like, no, it gives you someone outside of yourself who can kind of take the reins and be like, I’m here to help you. And so it’s worth every penny.

Jason: All right, so just to kind of wrap this up, she ended up finding a doctor that I could do a teleconsult with, which is also just lovely. We’re in the time now of this.

Caroline: Wait. Can I also share? So you go in, we go to the hospital to do your MRI. It’s on a Saturday.

Jason: Oh, yeah.

Caroline: And it was…

Jason: Like 5:30 p.m.

Caroline: It was 5:30 p.m. And when I tell you there was not another patient in this, the lights were off to keep it cool. There was two people at the reception desk, not a person waiting, which was totally different because when we went for your eye appointment, it was like a totally full waiting room. That was so weird, though. It kind of almost was giving, like zombie apocalypse type vibes. Not in a scary way, but just in like a, What is happening here?

Jason: Exactly.

Caroline: Anyway, but then I got very calmed by it because I was like, oh, you’re not with a bunch of people, and it’s not stressful. And so then we just had to wait in the little corridor while you had the MRI. But immediately, they did email you kind of like the assessment, but it was written in kind of medical-ese.

Jason: And in Portuguese.

Caroline: And in Portuguese. So it was all of these very medical words. And so I used ChatGPT to put… I was like, I can’t tell if this is really bad or just like, these words sound really bad because they’re very anatomical. So I put it into ChatGPT and I was like, Can you please explain this to me like I’m five? What’s the assessment? I had to do a couple of iterations until I… because I had to keep defining words. They would like, use… I’m like, no, I need you to define what a bone contusion is or whatever. The final thing spits it out. And I’m like, Babe, this is not good. I’m like ChatGPT. I didn’t know before, but now I know for sure. Dr. ChatGPT says this is not good.

Jason: So I got set up with a teleconsult with an actual doctor who wasn’t Dr. ChatGPT. He gets on the call. Also, just to be totally honest, it was like an hour I had to wait for the call, which, if any, we’re all used to that, right? And it was the first time I’d be like, Okay, this is just kind of normal for everywhere.

Caroline: It felt like that would happen to you in the States.

Jason: He was like, I’m so sorry. I had to go jump into surgery to help someone finish a thing. And I’m back, and I’m like, Okay, that’s fine. Did they do okay? Did you give him your full attention? Because that sounds more important than this. But anyway, his face, when he looked at my MRI, he was just like, it’s not the worst knee I’ve ever seen because I’ve seen people in bad accidents, but it’s a terrible knee. He’s like, Both your meniscuses are torn. Your ACL is torn again. You have bone bruises. You have loose bodies floating around in there.

Caroline: Like, Whose bodies?

Jason: When the bodies hit the floor of your knee, it’s not good. Which I do know that there’s been stuff moving around in my knee because my knee will kind of, like, catch in certain times. So anyway, long story short, I want to get another doctor’s opinion because basically his resulting opinion was, you should probably have arthroscopic surgery just to clean up the loose bodies that are floating around your knee because that’s going to just not do well for you bending your knee forever. He was like, But I wouldn’t repair the ACL and basically just resign yourself. You can’t do anything athletic moving forward. And I understand everything he’s saying, and I want to believe him, but I also would just love to get a second opinion just to know because that’s like, being 41 years old and being told, like, I can’t play paddle ever again. I can’t play golf, can’t do anything active, really, with knee stuff. And I feel like I do have some years left to do that. Not in a super stressful way, like a calm knee life way.

Caroline: Right.

Jason: So I’m waiting to get booked on another opinion and then kind of go from there. And as of right now, I’m just doing as much strengthening stuff as possible.

Caroline: Would you say that your goal…? You’ve, I think, mourned the loss of, like, you’re not going to play basketball again. You’re not going to whatever. But you still want to be able to do some things.

Jason: I would like to play paddle. I would like to play golf if I can. If I hear from a doctor that, Yeah, if you were to strengthen your knee enough for the next six months…

Caroline: You could do this.

Jason: And we do maybe another MRI and just see if it looks like things are a little bit better. Maybe I have arthroscopic surgery because, again, I do think the loose bodies need to be taken out of there. Like, those shouldn’t just be floating around.

Caroline: Or, like, swimming.

Jason: No, thank you. I’m not interested.

Caroline: I’m just trying to think of sports that you can do for 20 years.

Jason: Yeah, I could graduate to that. I could get more into yoga. I do that a very little bit now.

Caroline: Yeah, but yoga is not a sport. I’m trying to think of, like, active sporty type things. Sporty sports.

Jason: What sports do you want to play together?

Caroline: Paddle.

Jason: Okay, well, I want to do it, too.

Caroline: I know, but I don’t want you to do it if you’re going to hurt yourself.

Jason: It’s okay. I can get new legs.

Caroline: No, this is our fight. This is our fight because “It’s okay” is what got you here. No.

Jason: But isn’t this a good story for our people? Don’t you love this content?

Caroline: Do you think it’s worth arthroscopic surgery for a good story? No, it’s not.

Jason: I haven’t gotten the bill for it.

Caroline: I would like to state my argument, which is that for the past ten years, you have had this mentality of, “It’s fine,” and that is what has landed you here at 41, staring down the barrel of a knee surgery without being able to play sports again. And so my thing is, I would like to protect your future 51 year old self, your 61 year old self, and so we’re not going to do “It’s fine” anymore. We’re going to do, listen to doctors.

Jason: Exactly.

Caroline: Now, where I do agree with you and I have your back 100% is also you have a desire for a quality of life that, if you…

Jason: Is a little more active.

Caroline: Is a little bit more active and I want to support you. I’m not going to tell you you can’t do these things. I just think we need to work with doctors to be like, What do I need to do in order to do these things?

Jason: 100%.

Caroline: So we’re aligned, but I don’t want to hear any more of, like, pushing through, and it’s fine, and loose bodies and ouchy. Wowchy. But it’s okay. I don’t want to hear that. I want you to check in with your body.

Jason: Cool.

Caroline: And I want you to know what your limits are.

Jason: We’re also down to have a chat. Hey, knees. How are you doing?

Caroline: Not good.

Jason: All right. Well, yeah, it was like I was telling you the other day, this is my last thing. Going downstairs is really the hardest part. When you have a knee injury like this, it’s a stability knee injury, because going downstairs is very difficult. It requires a lot of stability. I noticed for the first time that I was thinking about it a ton, like two weeks ago, a ton. And then I was telling you, I really tried to check in with myself and be like, Does this hurt? And I couldn’t answer that question.

Caroline: Yeah.

Jason: Which is never a good thing, but I don’t think it does. I don’t think it does hurt.

Caroline: Okay. The fact that you’re not positive that it doesn’t. It’s concerning.

Jason: I just haven’t had a lot of time thinking about pain, so I’m going to think about it more. We’ll see.

Caroline: I cannot understand how your brain doesn’t… is confused about whether something hurts.

Jason: Yes.

Caroline: I don’t have that experience.

Jason: I’m also confused, just to be honest.

Caroline: Okay.

Jason: I was having the conversation. I was like, Does this hurt? Is there hurt?

Caroline: What is pain?

Jason: I don’t know. All right, let’s wrap up there. That’s our episode. Hope you enjoyed my knee news. Also, I’m just trying to be really positive about it because I had a day of grieving once I had that call with that doctor because basically he was like, Don’t ever do any sports ever again.

Caroline: And that was shocking.

Jason: That’s not fun. But I also afterwards was like, I do want to talk to another doctor because I just want to get a second opinion because this is his opinion. If the other doctor says the same thing, then I will just take it. Two doctors telling me not to do it, then that’s fine. My career of doing any type of super active physical thing is done. I’ll start swimming. I’ll start doing competitive stationary badminton.

Caroline: By the way. It doesn’t mean you can’t ever go outside. Like, we’ll still walk.

Jason: Have to live.

Caroline: Cornhole, professional cornhole. You can get really into darts.

Jason: I’m going to get 100% in Tears of the Kingdom a thousand times.

Caroline: You can still exercise, workout, do all these things. It’s just like sports.

Jason: Yeah. Nice. Okay. All right, everybody, that’s it for this episode.

Caroline: If you like Calm Business Confidential…

Jason: Let us know.

Caroline: Please email us, hello@wanderingaimfully.com. If you have a calm business, maybe it’s your business. I don’t know. That you’re like, Hey…

Jason: If it is your business, it just needs to be interesting.

Caroline: Give us a twist.

Jason: That’s like, Oh, I solved this problem. I overcame these things. This was a really interesting way that I grew it. It replaced my income.

Caroline: I did this, and it wasn’t working. Then I pivoted, and it really all started to work. These are the things we look for.

Jason: Yeah. All right, we’ll talk to you in the next episode. Bye.

Caroline: Thanks for listening.

Jason: Shrek or Elf?

Caroline: Elf.

Jason: Elf.

173 – Why We Love 30-Day Challenges and Our Next One

(Big Fat Takeaway)

We LOVE 30-day challenges and are embarking on a daily YouTube and written article content blitz leading up to our next launch.

IT IT

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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