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172 – The Next Big Move With Our Software Product (and NEW Segment!)

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

172 – The Next Big Move With Our Software Product (and NEW Segment!)

Coming back from our summer sabbatical, we introduce a new segment on our podcast and, for the first time, we have a pretty big change in our new user signup process on Teachery!
Jason ZookJason Zook Jason ZookJason Zook

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Jason Zook

Listen to our full episode on The Next Big Move With Our Software Product (and NEW Segment!) below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.

Five Key Takeaways for The Next Big Move With Our Software Product

1. Introducing Teachery Starter Themes

We identified our seven main/focus users on Teachery and built a theme for each of these users to start with. The purpose is to give them a good starting place that is designed for their style of business. We have a theme for brand designers, artists and makers, yoga or wellness teachers, coaches, stylists, food influencers, and productivity experts.

2. Outsourcing theme designs

Caroline did the first Starter Theme design and then put together a tutorial lesson that walks through how to customize things. Once we had that, we gave it to a designer, who is also a WAIMer, and let her pick from the remaining six archetypes.

3. Are you the accelerator or the brakes?

We talk about having complementary skillsets and finding someone who might complement your skillset, too. This works really well for us because Jason’s so good at barreling through obstacles and moving the ball forward regardless. And Caroline is really good at saying, “Hey, slow down for a second. Let’s be more intentional, let’s be more thoughtful, let’s be more strategic.” We think those two things help us work really well together.

4. Moving Teachery’s front-end site to Webflow

One of the bigger decisions was to move our Teachery home page and our pricing page into Webflow. We knew that we had these ideas for landing pages or fun copywriting things for Teachery, but our website has been hard coded for many years. We also want a content management system (CMS) in order to empower us to be able to make changes to the website on the fly and create more marketing content for Teachery.

We think anyone listening to this can relate to that of moving to a new tool or to something that is going to improve your business. There is a learning curve and you have to just make the decision that you’re going to commit the resources to be able to use that tool effectively.

5. New segment: Calm Business Confidential

We struggle to find inspiring stories of “calm businesses.” Meaning, you’re not running around managing a bunch of people nor putting out fires all the time. You identified a way to make money and decided to use the Internet to do so. You did it for the pursuit of living a life that aligns with your own personal values, and you succeeded in doing that. We didn’t know where to go to find that, so we created it.

👨🏻‍🦲 Jason’s feature: Chenell Basilio from

👩🏻‍🦰 Caroline’s feature: Liz Sharma of Talk The Streets.

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

Show Notes for Episode 172: The Next Big Move With Our Software Product

This week, we go through a big move we’re making with our software product Teachery. For the first time, we have a pretty big change in our new user signup process! We’ve created 7 pre-designed course themes to get someone up and running much faster with their online course. We’re also moving our marketing site to Webflow so we have more control over marketing content, landing pages, etc. We’ll keep you posted on the progress!

We also introduced a new segment called Calm Business Confidential where each of us brings an interesting calm business to the podcast without telling the other person about it before recording (hence, the confidential part 😘). Hope you enjoy the new segment and learning about calm businesses that aren’t billion dollar companies trying to change the world.

Last but not least, we update you on our summer in Portugal, including spending 3 weeks with Caroline’s Mom, road-tripping to the Douro Valley wine region, and an update on our residency card status.

Full Transcript of Episode 172: The Next Big Move With Our Software Product

⬇️ 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 are 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.

Jason: Hello, and welcome back to the podcast.

Caroline: What a strong start.

Jason: Wow.

Caroline: What a bellowing start.

Jason: Jeez, how long does it feel like it’s been since we’ve recorded a podcast?

Caroline: Two months?

Jason: I would say nine years. Feel like I haven’t recorded a podcast in nine years.

Caroline: Do you feel rusty?

Jason: Nine years ago was the time when I last spoken to a microphone.

Caroline: After the COVID era, I don’t even know what time is anymore. It moves very strangely.

Jason: It’s definitely a construct.

Caroline: I feel like when you hit your 30s, time does a weird thing. I don’t like it.

Jason: Yeah, well, wait till you get to your… Just you wait. It’s our favorite phrase. Just you wait.

Caroline: Just you wait.

Jason: All kinds of different things.

Caroline: Wow, you must be really wise.

Jason: We’ve got some changes here. As the producer of the show, I’m going to share with the listeners the changes.

Caroline: Okay, great. Made some updates.

Jason: We normally do our Pramble, which is our discussion about our lives in Portugal or, like, something that’s going on. We’re going to move that to the end of the podcast.

Caroline: Now, some of you who love starting off with that…

Jason: I love it. I love starting off with it. But I’m the one who actually kind of voiced this as a decision. And if we hear from enough of you that you want it back at the beginning, we’ll move it back around. But we’re going to go right into the crux of the episode to start, the topic of the day.

Caroline: Which is what are we doing in our businesses? What are we struggling with? How are things shaking out?

Jason: What’s going on? Then we have a new segment alert.

Caroline: Very excited.

Jason: New segment alert.

Caroline: New segment alert.

Jason: Do you want to announce the name of it now or when we get to it?

Caroline: When we get to it.

Jason: Okay, so we have a new segment we’re going to bring to this, and there’s also going to be some user participation with that.

Caroline: Did you want to try that again?

Jason: No, that was on purpose.

Caroline: Okay.

Jason: Yeah, that’s a purposeful way to speak to mix up people’s… It’s already hot. It’s already hot.

Caroline: You’re okay.

Jason: Turned off the loud AC. Needed it.

Caroline: I know. I know.

Jason: Shout out to everybody who’s dealing with just the heat. Like Jeez. Wow. It’s crazy. We’ll talk about them later. And then so crux of the episode, new segment alert. Then the Pramble, which is now not the Pramble… It’s the…

Caroline: Post.

Jason: The Pomble. The Pomble?

Caroline: The post…

Jason: Pramble.

Caroline: Postagal. Portugal post.

Jason: Pomble? I like Pomble better than Postagal.

Caroline: You like Pomble?

Jason: Better than Postagal.

Caroline: What does Pomble stand for?

Jason: Post pramble.

Caroline: But pramble.

Jason: But I love the Pramble, you know? I know.

Caroline: Pomble. It’s growing on me.

Jason: Okay, so without further ado, let’s get into this week’s episode.

Caroline: Great. Let’s start.

Jason: This sounds weird.

Caroline: What do you want to talk about?

Jason: Feels weird. So I really wanted to…

Caroline: What are we even doing? How did the summer go?

Jason: I wanted to… No, we’re not talking about how the summer went. That’s later if you want to talk about that. We are getting into the…

Caroline: I meant, like, summer business wise.

Jason: Okay. Not a lot of things because we took a break. That was the intention.

Caroline: We did.

Jason: But I will say the thing that I wanted to bring up and really share with everybody is kind of this really truthfully, since the redesign of Teachery back in 2020, this is the biggest project for Teachery, I believe, especially in moving the ball forward on trying to do some type of marketing/ growth initiatives that are not just customer service led, product led, or word of mouth led. So this is really kind of putting something on the forefront of Teachery on the homepage, which we’ll talk about in a second that is our hope going to increase these sign ups for new trials, which then increases people sticking around and being paid customers for Teachery.

Caroline: Great.

Jason: What this is called, and I think we maybe mentioned this loosely in a couple episodes prior to this, but now it’s, like, finally done.

Caroline: Yeah. Can I add just a little bit of context?

Jason: Oh, absolutely.

Caroline: Just in case anyone is, like, joining us and whatever. So our intention this year… We have two businesses, if this is your first time listening to the podcast, one of them is Wandering Aimfully, which is an unboring business coaching program, but the other business is a software business called Teachery, which allows you to build online courses on our platform. Now, Teachery has always been sort of this side project, and part of our intention this year, as we ended our full year of travel, we traveled around Europe full time last year. We settled down in Portugal, and our intention this year was to finally make this the year that we put some love and care. Not that you haven’t put love and care because you absolutely have.

Jason: Yeah. Teachery has always been the side project.

Caroline: Exactly.

Jason: Of our family.

Caroline: And so we really wanted to elevate it from the back burner to the front burner and start really thinking about how we want to grow this business.

Jason: You know what Teachery has been?

Caroline: What?

Jason: It’s been the neglected plant in your house. It’s alive.

Caroline: It’s alive.

Jason: It’s not dead.

Caroline: Spritzing it every once in a while.

Jason: It stayed alive for ten years.

Caroline: Yes.

Jason: But you know what?

Caroline: You’re ready to bring it to the living room.

Jason: It’s not thriving. It does not deserve to be in the living room.

Caroline: You need to do some research. You need to find out…

Jason: WAIM? It’s an abundant plant in the living room.

Caroline: It’s like a fiddle fig leaf that’s so happy.

Jason: Oh, yeah.

Caroline: Growing all sorts of new branches.

Jason: Teachery is just like that real scraggly looking plant. You’re like, I know you’re alive, but you don’t look great, sir.

Caroline: Right. And so now it’s time to bring the Teachery plant into the living room.

Jason: Not yet. We’re going to do this first and see how it goes. But I’m not ready to…

Caroline: We’re going to start looking up some food it needs. Maybe a correct watering schedule. And then once we get thriving, we’re going to move into living room.

Jason: That plant needs water. Let’s go do that.

Caroline: Right.

Jason: Yeah.

Caroline: That’s where we are. So this year is really the foundation. It’s replanting the soil and everything. So that is the context because we did a few things at the top of the year, which was really took a look at where does Teachery sit in the market compared to other course platform tools? Because now there’s a ton of them. Who are we trying to really target with Teachery? Who is it the best fit for? And then now, how can we build out features in order to serve that person? And really, where Teachery shines is the ability to create a custom branded experience for your course content to shine and really be integrated into your full branding it’s for creative entrepreneurs. However, not a ton of features were highlighting that about it.

Jason: Right.

Caroline: And also, we know that building a course is a pretty high barrier for people to get started with our product. So how can we make that easier? Enter this new iteration, a really big feature that we call Teachery Themes.

Jason: Yeah. So we created Themes last year, which is basically a way for anybody who’s a course creator to take a course they’ve designed, turn it into a theme, and then they can sell that theme for other people to use their design to spin up their next course.

Caroline: So… And just what a theme is, is it’s like a fully you choose all the colors, you add images. It’s a course container that if Jason was selling a course theme, I could buy it. And then I basically have a beautifully branded course right out of the box.

Jason: I mean, if I’m creating it, obviously. How much would you pay for…?

Caroline: All I have to do is drop in my course content, my videos.

Jason: How much would you pay for my course name?

Caroline: How good is it?

Jason: It’s good. Yeah.

Caroline: $400. Wow.

Jason: Okay. I literally thought you were going to say $19. This is incredible. You’ll buy today?

Caroline: No, because the way that I view it is it saves me 20 hours.

Jason: Can I get my credit card reader right now?

Caroline: Sure.

Jason: Okay. I’ll take that payment.

Caroline: Our money is shared.

Jason: That’ll look weird.

Caroline: I’m paying for your own course theme.

Jason: That’ll look weird. Okay. Yeah. So we’ve had the feature of Themes, but now the idea is, let’s kind of, like, fast forward all of this to… Right now, it’s very hard when you start. It’s not hard, but it’s very difficult when you sign up for teacher to get to that aha moment with your course. You have to put a lot of labor into it. You got to put a lot of time designing. You got to do a lot of things, and that takes a lot of mental effort and a lot of time, and we know that. But for some people, they love a blank slate, so they’re happy to start with… like, you would always love to start, I think, with a blank slate.

Caroline: Totally.

Jason: I would love to start with a predesigned thing because I’m not as talented as a designer. I don’t want to make as many decisions on colors and brand and things and fonts. So I would love, like, a good starting place, and then I could customize it to my own. So what we did is we basically sat down and we said, okay, let’s identify, basically our seven users that are kind of our core focus users who use Teachery, and let’s build a theme for each one of these users to start with. So if we know that we have these seven people who use Teachery or we want to start using Teachery as their preferred platform, let’s give them such a good starting place that as soon as they sign up, they get a theme that’s designed for their style of business, or at least their niche of business, and boom. Immediately. Aha moment. Wow, this looks like a theme related to my type of business, and now I can get going and customize it and do whatever.

Caroline: Cool. Do you want me to tell them what the themes are?

Jason: The seven people who we identified with the seven people were, and then we can do the themes.

Caroline: Sure. So we have a theme for basically brand designers. So that’s, like, anything in the design and visual category. So you could very easily adapt this into, I’m a web designer, I’m using a specific tool, et cetera. But it’s kind of brand designers is who it’s for. We have a theme for artists and makers. So if you’re someone who makes jewelry. If you’re someone who…

Jason: The theme is like clay earrings.

Caroline: Yeah, it’s very fun. If you are someone who is a painter, if you are someone who is a watercolor artist, a hand letterer, it’s very well suited for that. We have a theme for yoga teachers, so if you’re in the kind of wellness, movement profession, anything related to that, it could even be adapted to fitness instructors, kind of health and wellness category. We have a theme for coaches, so the theme is set up for, like, a relationship coach, but if any type of life coaching, business coaching, any of that.

Jason: What about like cinnamon roll coaching?

Caroline: Baking coaching? Sure.

Jason: Cinnamon roll coaching?

Caroline: Cinnamon roll coaching. Absolutely.

Jason: Okay.

Caroline: We have one for stylists. So anything like kind of lifestyle, personal style related as a category. And then we have one that is for food influencers. This really could be adapted to any type of niche category of kind of influencing if you wanted a companion course to whatever kind of your niche of content is or if you’re a content creator. And then finally we have kind of a productivity… So if you’re selling Notion templates, if you’re selling a specific course on a tool, something like that, it’s really geared for that. So between those seven themes, it kind of covers a large swath of the people that we see who come to teach Tree looking to build courses.

Jason: And the people that we think are best suited to use a course platform that’s based around customization.

Caroline: Exactly.

Jason: And ease of use.

Caroline: Exactly.

Jason: I think one of the things at the beginning of this year… and we’ve known this, but kind of my ethos has been since I brought this house plant and left it in the basement for years is just don’t pay attention to any of our competitors. I just want to build the product that I wanted to use and that I believed would be useful to people. And that has proven true. We have gotten to a certain number of users who agree with all those things. But I think it was really helpful to take… and you did the bulk of this work because this is where your genius comes through.

Caroline: Oh, wow.

Jason: Is basically looking through the landscape of competitors and we don’t care to name them. So it’s like Podia, Teachable, Thinkific. Like all these different folks and what are they doing? What is their core offer? And especially what do we see as a fellow competitor? What stands out?

Caroline: And what is going to make someone want to choose Teachery over those options? Why would we be a better fit for what they’re looking for? We have to determine what that is so that we can carve out a place for ourselves in the market.

Jason: Yeah. So where we started with this project was you did all that research, we then kind of identified, okay, our core difference is customization. Now what can we do to get someone to that customization? Okay, let’s use our themes. Let’s talk about who these people are. Okay. What courses would that look like?

Caroline: Right. What type of creative entrepreneur is going to be more attracted to give me all the styling options versus the person who really wants the powerful email marketing tie in and don’t really care about the container, just want to drop in the videos. Doesn’t care that it looks like every course out there, is more interested in the automation. That’s not our core product. So we have to differentiate.

Jason: And listen, we just had someone sign up the other day that’s a college. Like, it’s a college in the US who’s going to use Teachery for whatever they’re going to use it for. And we’re not going to say no to those people in the future. But we know that our platform better serves these seven archetypes, so those folks can definitely still sign up. It’s not going to be any different for them. But this starting place for these seven groups of people, I’m very excited about. So kind of the logistics of that. You designed the first theme, which was the productivity theme, which was around Notion, and put that together. And what we wanted to do is kind of see like, okay, what’s this process? Like, what does it take? Because what we knew is that you didn’t have the time to do all seven themes to start with, so we were going to outsource that work. And we have a very talented designer who already builds things in Teachery that we said, hey, would you mind doing some of these? And she was very excited, which was great. And so you did the first one, went through the whole process, designed the lessons, designed the overview page, designed the landing page, designed the payment page, and then put together kind of a tutorial lesson that walks through how to customize things. So once you had that, we went, okay, great, let’s give this to the designer, and let’s kind of just let her run wild and just pick from the remaining six archetypes. What do you want to work on? Like, what’s calling to you, what feels good? And just give her a lot of freedom and flexibility because, with something like this and I think this is just a good business reminder for everybody, it’s like you just don’t know what you don’t know. So you can say, like, oh, is it a bad decision to do, like, a food blogger course in Teachery? Like, everyone just puts their recipes on their website. Yeah, maybe, but it also could inspire a lot of people to think, like, oh, I put some of my recipes on my website, but then you get the bulk of my recipes through a course or whatever.

Caroline: Yeah. And I think the lesson you’re trying to say there is don’t overthink it because that can slow you down quite a bit. And this is where our skill sets are very complementary because we often say, you know, Jason’s the gas and I’m the brakes.

Jason: Excuse me? I’m the accelerator.

Caroline: Okay.

Jason: Yeah. Just trying to…

Caroline: Jason’s the accelerator, and I am the brake.

Jason: Trying to move to a cleaner world, you know what I mean?

Caroline: That’s true. That’s your guess. Okay. I was like, I didn’t get it.

Jason: Yeah.

Caroline: I got it now.

Jason: Yeah. Okay. Welcome to the show.

Caroline: Thank you so much. And that works really well for us because Jason’s so good at kind of barreling through obstacles and moving the ball forward regardless. And I’m really good at saying, hey, slow down for a second. Let’s be more intentional, let’s be more thoughtful, let’s be more strategic. And sort of the tension of those two things I think helps us work really well together because you help me not get in my own analytical brain where I’m like full stop, wait, we need to be so thoughtful that we’re not even making progress. And then whereas you might barrel forward without thinking of the extrapolations of our decisions, I can be more of that person who thinks ahead and goes, wait a second, have we thought about X, Y and Z and how that will affect us in the future? And we work really well together. So I think a good takeaway from this episode is to listen right now and go, do you think you are more of an accelerator or do you think you are more of a brakes? And if you’re a breaks kind of a person, can you find a business partner or a business friend who you can do their calls with, who can be that accelerator for you and kind of help you push through? Or the opposite is true as well. If you find yourself that you tend to be an accelerator and maybe don’t think through every decision, can you find someone who’s like a little bit more thoughtful and analytical to be a sounding board for you?

Jason: Also, if you just want to live life dangerously, just be an accelerator all the time. Just go for it. So the designer finished up the six themes that she worked on. Super happy with all of them. Fantastic.

Caroline: So fun.

Jason: Very excited to see how these go. And then the next step in this process was to basically build a way to showcase these for people to start their journey into Teachery using these themes. So we got our other designer that we have used before to redesign our homepage for Teachery and it was funny because you did a wireframe of it and we kind of had this standard SaaS thing at the top. SaaS is software as a service, but it’s like the standard thing when you go to any software website where it’s like the hero statement and then like a supporting statement and then like an image of the thing next to it and whatever. And we were going back and forth. I was like, yeah, that’s fine. I was like, but what if we just said let’s just skip all of that and just get people right to the themes. Just like the first line of the thing is like, start with a theme. You know, you want to make a course. Here are the seven themes we have available for you. Or you can start from scratch. Just get going. So I’m going to be very curious to see how people receive this because it is a little bit different than kind of the standard opening to a site. But anyway so the designer did the full design and then we decided one of the bigger decisions was to move our home page and our pricing page into Webflow. And you want to talk about why we’re doing that?

Caroline: Well, we knew this was an inevitability but as we started having conversations about, and we haven’t even decided, we haven’t landed on anything yet but we know that content marketing is potentially in our future of Teachery has zero articles.

Jason: Maybe. I still would love to… I would love the story to be…

Caroline: We never wrote a blog post.

Jason: Exactly.

Caroline: Maybe. But we knew that we had these ideas for if we’re going to do outward marketing for Teachery, we had a bunch of ideas for landing pages or fun copywriting things or whatever. But our website is hard coded. Meaning, it’s not on a content management system. Meaning, anytime that we want to redo the home page or create a new page of our website, we need to basically take our developer away from working on features in order to work on the marketing side and that didn’t seem efficient to us or efficient use of resources, especially when we have enough copywriting web design skills. All we needed was a content management system, a CMS, in order to empower us to be able to make changes to the website on the fly. So we knew that eventually we would need to move to some type of system.

Jason: Yeah and fun fact, when Teachery was first brought home as that plant, it was a WordPress site that was on the front end of things. So the homepage was coded in WordPress. The help docs were all in WordPress. I could go in and update and change those things but it was when we did the first little redesign, we moved everything into more static things and then all the help docs got pulled into…

Caroline: Do you remember why you did that?

Jason: I think it was actually my previous co-founder wanted to… It was just like a better system.

Caroline: Well and he was a technical co-founder so it made sense for him because he was like well if anything we can change, I can change it.

Jason: Exactly. So we got rid of WordPress. We were just a static site for the past like five or six or seven years or whatever that is. So now we will be moving to Webflow and experience a whole new platform to be building on. But we’ll have ability to actually change anything, change copy, switch out pages. If we want to have a whole new page designed, we can literally flip it out very easily and very quickly. Whereas before, it’s fairly quick with a developer, but again, like you said, it takes them off of other tasks and projects and it doesn’t give us the flexibility to actually change things and do things.

Caroline: Yeah. And I will say these are the changes that you make that there are a little bit of growing pains because I have a little bit of experience with Webflow, but many years ago.

Jason: I know how to log in.

Caroline: Good job.

Jason: Thank you.

Caroline: Great job. And so we have to refamiliarize ourselves. We have to educate ourselves on how to use the tool. And I think anyone listening to this can relate to that of you know that a move or a new tool or something is going to improve your business. But there is a learning curve and you have to just make the decision that you’re going to commit the resources to be able to use that tool effectively.

Jason: I think… Yeah. The other fun part of this is what we could have done is gone into Webflow, learned Webflow, experimented with Webflow, figured it all out, then hired a designer, then hired a developer to build everything. We did the opposite. We know barely nothing about how to use Webflow. We just paid a designer to design the page. I found a developer on Upwork to code the page. That has been done and now it’s like, well, let’s figure out how to use Webflow.

Caroline: Well, that’s a good example of we’re the accelerator. And I was just excited to get the thing up and running, so I just said, sure.

Jason: Yeah. So where we kind of sit in that process. Currently, our developer is working on… there’s a new kind of sign up flow. So from the new homepage, you’ll be able to click, Start with theme, any of those seven themes that you just discussed. And someone will literally start to create their trial with that theme being ready for them as their first course.

Caroline: And if you’re listening to this and you’re like, wait, I’ve never even tried Teachery. Once this is live, just a reminder, we do have a 14-day, no credit card free trial. So you’ll be able to start with a theme, get in there and see what it looks like.

Jason: Yeah. And my goal would really be, I would love for someone to start a trial, pick a theme and then go, you know what? I liked one of the other ones and using the other ones and just have the freedom to have these seven different themes at your disposal to not start from scratch. So whatever your business is, whatever you’re selling, whatever your course is about, it’s not like these themes are only for those things. They’re just a good starting place for design and the way that kind of content is being shown.

Caroline: Yeah, so we’re really excited about that. We still have a few final things to button up. We have to do…

Jason: Some fun DNS we get to do. We get to switch over…

Caroline: Things we need to do with the homepage. We need to switch it over. We need to hook up our new trial onboarding flow to that. So do we have a target date for that, Jason?

Jason: I don’t know, but I think we’re, as of recording this, probably like two weeks away at maximum because the hard part is done. The page is coded. The onboarding flow is going to be pretty easy for our developer because we already have a very similar flow. It’s just adding in a separate step. It’s going to be him hooking up a couple of things, but he’s really fast and great at things. So you have a couple of changes that you want to do and a couple of little bits and bobs, but once that’s ready, yeah, I’m excited for that to be up. And we’ve had very consistent analytics for Teachery’s traffic, conversion from homepage to trial, conversion from trial to paid customers.

Caroline: So it’ll be really clear.

Jason: Exactly.

Caroline: To see, did this have an impact?

Jason: Exactly. Even if the impact is not necessarily, oh, our trials went up a ton, and oh, our monthly customers went up a ton. I just want to start hearing from people that, oh, my gosh, I got in, and I have a course that’s already designed. I just had to make a couple of tweaks. And I’m so much happier using Teachery because overall, that’s a big win. And then from there, it’s about figuring out like, okay, like, what are the other things that we want to work on? But I think this was like, again, our first big move of the plan is coming out of the basement, maybe to a room adjacent to the living room, but not quite in the living room.

Caroline: Not quite in the living room yet.

Jason: It’s going to get some better light, though.

Caroline: It is going to get some better light. And the reason why we also weren’t quite sure on the deadline is because we’re in a little bit of a funny time period right now where this is the conundrum of having two businesses that are taking up equal priority. We now have to shift gears into kind of letting the soil do its thing and the new light get to the plant while we go focus on our living room plant, which is Wandering Aimfully, because as most of you know who have listened to the show before, Wandering Aimfully runs on a twice a year launch schedule. So we always do a Spring launch of our coaching program and a Fall launch of our coaching program. Our Fall launch is coming up before we know it.

Jason: Wouldn’t you know it, summer’s coming, coming to a close here in a couple of weeks.

Caroline: So we usually gear up about eight weeks out from a launch to get things going, and that is upon us. And so we’re kind of switching gears to then focus on that until the launch, and then we will be able to maybe get in one or two more initiatives with Teachery before the end of the year.

Jason: What do you think about next week’s episode? We’ll talk about the WAIM dashboard because we just relaunched.

Caroline: I like that idea.

Jason: We’ll take everybody through that saga because it wasn’t easy. Wasn’t easy as it never is. All right, I think that wraps up talking about Teachery, the starter themes, how we’re working on things and just excited to have a big change with Teachery, you know. We haven’t had a big outward facing change. We’ve had these features like themes, and we’ve had changes and improvements to the application, but all that stuff is internal. Course Hubs was a big feature that we launched. That’s a good one, but it only gets you so far because you’re not replacing the whole homepage to talk about that, whereas this one’s going to be like replacing the whole homepage. It’s the first thing everyone sees.

Caroline: Of course. And then any outward marketing that we build on top of that is really going to rely on whether themes is an effective way now to get people into the platform. So, yeah, it’s a lot of exciting things ahead in the next few months for Teachery.

Jason: All right, let’s move into the new segment. Do you think an editor is going to put, like, a sting into the new segment at some point? Maybe not the first one, but maybe we need…

Caroline: Eventually. If people like this segment.

Jason: If people like this segment, I will be allowed to go on whatever my music…

Caroline: Budget.

Jason: Service is of choice, and I have some budget to get a little sting for this new segment.

Caroline: And a sting is just like a little audio clip, right?

Jason: Yeah. Like.

Caroline: Now, do we even need to buy anything or do we use that?

Jason: Maybe that’s it. Here, you add something to the end. Ready?

Caroline: Okay.

Jason: Nice. Welcome to…

Caroline: I didn’t want to…

Jason: Clean. Clean. Welcome to Calm Business Confidential.

Caroline: We took it to different places.

Jason: All right, Carol , what is Calm Business Confidential? Our new segment.

Caroline: Okay.

Jason: Also, are you sweaty?

Caroline: Yeah.

Jason: From the improv.

Caroline: Made me sweaty. Improv not my strong suit. That’s okay. We do hard things and…

Jason: It’s okay.

Caroline: We go out of our comfort zone and that’s all right.

Jason: Yeah.

Caroline: Calm Business Confidential. So Jason and I have been talking about this a lot lately, which is that… Okay. There’s so many people now on YouTube, on podcasts, everywhere you look, talking about big businesses, billion dollar businesses, 100 million dollar businesses. Why? Because they’re flashy and they’re interesting and they’re outliers. And so you’re like, wow, so and so started from nothing and built it to $300 million. The thing is, especially like in our Wandering Aimfully intentional business ethos, we’re not interested in running a 300 million dollar business with 300 employees and managing people and whatever. We just want to live a good life with a profitable business with still some ambitious financial goals. We want to be able to buy a house. We want to be able to have retirement.

Jason: I want gold teeth.

Caroline: Jason wants gold teeth. Great. Whatever you want is great.

Jason: Just because I have bad teeth. But eventually…

Caroline: We always struggle to find these inspiring stories of these businesses that are what we would call calm businesses. Meaning like, you’re not running around managing a bunch of people. You’re not putting out fires all the time. You identified a way to make money. You decided to use the Internet to do so. You did it for the pursuit of living a life that aligns with your own personal values, and you succeeded in doing that. And so we were like, well, I don’t know where to go to find that, so why don’t we create it?

Jason: Yeah, it’s very disparate if you go on any websites like or I was trying to think there was another one, like Startup Stories. It’s not easy to find. And so I think we just hope this segment becomes like a weekly thing where you get to hear about two of them because each of us is going to bring one to the other person. So that’s part of this is we’re going to do our own research.

Caroline: It’s why it’s confidential, Jason.

Jason: And it’s why it’s confidential. So I have a business and a person that I’m going to talk about. You have a business and a person you’re going to talk about.

Caroline: And it’s really just us finding these businesses.

Jason: And then sharing them together and then with you all.

Caroline: Exactly. We want you to be inspired. We want you to be like, oh, that’s interesting, and they don’t have to be earth shattering.

Jason: Do you want to share the parameters?

Caroline: Sure.

Jason: We have a couple of parameters that I think will help just as a guiding life. Like bumpers and bowling. Right. These are our bumpers.

Caroline: I don’t remember our bumpers, but I think mine fits into that.

Jason: You don’t remember the bumpers? I was like, you don’t remember the little thing? You slide down, you don’t get a gutter…

Caroline: You don’t remember bumpers?

Jason: Like, those are helpful.

Caroline: Yeah, those are helpful.

Jason: It makes bowling fun.

Caroline: So what do you think the parameters are?

Jason: So the parameters of this are kind of on the high end. The business can’t make more than like a million, 1.5 million per year.

Caroline: Okay.

Jason: We’re probably not really going to get into many of those anyway, but we just wanted to leave room for like there might be some really fun or interesting ones.

Caroline: That are bigger.

Jason: Maybe has a good story, and it obviously didn’t start there, so we wanted to leave room. The business needs to be making some money, but it doesn’t have to be making that much money. If it’s an interesting business, if it’s just something that kind of catches our eye, like my one, this thing, I have no idea how much this business is making and I don’t think it’s that much.

Caroline: Okay.

Jason: But I love the model because I believe in it, personally.

Caroline: Love it.

Jason: And so I think it’s very fun.

Caroline: Cool.

Jason: So that’s that. And then we’re not really talking about physical products out in the wild. We’re not going to really talk about, like, a furniture company per se.

Caroline: No, it’s more online heavy, because we know…

Jason: But it can be like a software product. It can be a piece of software. It could also be…

Caroline: A course business. It could be a content creator that’s monetized it. Like these different ways that you can make money primarily using what we call the Internet.

Jason: All right. Calm Business Confidential. The intro next week will be much faster, and then we hope you enjoy this. So definitely give us some feedback,, if you want to send us a message that you like the segment because that’s how we’re going to know and get feedback if you like it.

Caroline: Okay.

Jason: Ladies first.

Caroline: No, no, you go first.

Jason: Okay, great. So my first Calm Business Confidential is someone who is a WAIM subscriber back in the day. Her name is Chenell Basilio. So I have told you about her business recently while we were doing this, but you didn’t know I was going to choose her. So Chenell has a business called

Caroline: Right.

Jason: What I love about this business is that it’s an email newsletter and it’s a blog.

Caroline: Love it.

Jason: And she does use Twitter a bunch. That’s her main marketing vehicle.

Caroline: That’s like her micro content.

Jason: But the overall idea of this business is she breaks down other people’s businesses in painstaking detail and then shares how they started that business, their biggest growth, like hacks or tips or tricks that they used, the decisions that they made along the way, the pivots, the other things that kind of led them to big jumps. And when you read one of these breakdowns, tons of great visuals. She puts all of these custom visuals together. There’s charts and graphs and things, and it’s like, I love this stuff so much.

Caroline: Yeah. And this has been a big topic of our conversations lately because I really do think that we’re reaching this point with information. There’s so much teaching information now that I feel like the next iteration of that is this case study angle. I feel like there’s a lot of opportunity for having some type of case study business. Also, the Growth.Design guys come to mind for that as well. Was that another one of yours?

Jason: Might be.

Caroline: Okay, well, too bad.

Jason: You can’t have that one.

Caroline: No, that’s not going to be mine.

Jason: Let’s stay clear of that because I do want to bring that up in a future. No, it’s fine. You can say if you want.

Caroline: Yeah, well, I’m interested in the bigger pattern here, and the pattern that I see because we just had a conversation about that this morning, is case studies are extremely valuable. So if the listeners listening to this, how can you integrate case studies into your business?

Jason: Yeah. Okay, so let me give you a little bit of background on Chenell, and we’ll get better at kind of like telling these stories. But again, this is the first time we’re doing it. So Chenell started this business about a year ago ish, but before that, for the previous five years, she was basically running Facebook ads for other businesses and other creators. So she was just like, slogging through creating Facebook ads and just finally got burned out on it. And one thing that she always loved was reading other stories, reading other people with breakdowns, especially kind of the build in public movement that’s on Twitter. There’s a lot of this on Twitter, but it doesn’t really translate outside of Twitter a lot of times. So she wanted to put this business together. When I joined her email list, I remember seeing it was like under 8000 subscribers. And this was a little while ago. And when I checked it today, she’s over 16,000 subscribers. So she’s doubled. She makes money. This business makes money through sponsors in the email. So the email is essentially like a blurb about what breakdown she’s doing with a big button to click to buy. So she doesn’t put the breakdown in the email because it’s very long. So it would be an incredibly long.

Caroline: Click to buy, you said. Or click to read?

Jason: Click to view. Sorry.

Caroline: To view. Okay.

Jason: And then below that is a sponsor. So she has sponsors in all of her emails.

Caroline: So it’s just an email newsletter business.

Jason: Yeah, email newsletter and a blog.

Caroline: I love the simplicity of that.

Jason: This is what I’m saying. Now, the caveat here is we don’t know how much she’s making. I did look it up. Her sponsors are $500 per email.

Caroline: Okay.

Jason: And she’s sending out one email per week. And she can have multiple sponsors in an email.

Caroline: Okay.

Jason: I haven’t really…

Caroline: You do the math.

Jason: Too much attention to that. So this business, four emails a week, making $2,000 a month.

Caroline: Not to mention, as the email list grows, your ad spots…

Jason: Of course.

Caroline: Can grow.

Jason: And when it was in the beginning, she was probably charging like $100. It probably wasn’t very much. And I think that this is a great example of the power still of an email newsletter, and not only just in the growth of it, like the fact that it’s gone from 8000 to 16,000 subscribers in what’s definitely less than a year because I didn’t find it more. And I think it’s barely been around for that amount of time. So I just really love this. Again, the majority of her growth of the newsletter is happening through Twitter and her sharing it and people resharing it. But one thing that she’s done that’s really smart, that I really love, and multiple people had pointed this out when I was kind of looking this up is she’ll share it and she’ll tag the person who she writes as review. Most of the time, the person doesn’t know she’s writing this review, so it’s not an interview.

Caroline: How is she finding the information?

Jason: She just does a deep dive.

Caroline: Deep, deep dive.

Jason: She does 20 to 30 hours of research every week. So she…

Caroline: Probably gets everything on every blog post on their website, every interview they’ve ever done.

Jason: She said I was listening to her on another podcast talk about… She was like, I literally walk for like 1 to 2 hours a day listening to podcasts to just take in all this information.

Caroline: That’s so great.

Jason: Yeah.

Caroline: I love that.

Jason: So, yeah, I really love the in depthness of the case studies. The actionable takeaways are really fun. is the website. You can check it out. We’ll leave it in the show notes below in our Calm Business Confidential section of our transcript or on our website where we break these podcasts down. But definitely one to keep an eye on, one to subscribe to, for sure. And I also just kind of love that Chenell was a WAIM subscriber really early on in our journey.

Caroline: And I know exactly why this was your first pick, because this is the type of thing that gets you so excited and me too, is the practical application of business. And every person’s journey is different and every person’s… We always talk about this idea that business is not a one size fits all pursuit. And it’s something that we struggle with sometimes because we want to give people tools that when you’re teaching one to many, like we are in our program, you do want to give tools that a large majority of people can use, but we always have to caveat it with it’s not a one size fits all fits all. You really have to take everything with a grain of salt and put it through your own filter. And I think case studies are the thing that fills that gap because people can start to see people’s unique paths and I love that a lot and makes me want to do something similar. Now, the only thing I will say.

Jason: Yeah, go ahead.

Caroline: I think she’s doing exactly what I would do, which is start with one monetization model being sponsorships, kind of get it off the ground. But for me personally, and this has no bearing on her decision making because obviously she’s making decisions based on the business she wants to be running. But for me, I’m weary of anything that relies solely on sponsorships.

Jason: Totally.

Caroline: Because you can never take a break, you can never decide we’re taking the summer off for sponsorships.

Jason: I have no experience with this.

Caroline: Exactly.

Jason: So I don’t know how hard this is. Yeah, I think it’s just a really good starting place.

Caroline: It’s a great starting place.

Jason: And I would guess that she’s going to get to a point where…

Caroline: She can diversify a little bit.

Jason: I bet she could also charge monthly and she could say like, here’s the first three case studies for free.

Caroline: Get access to the vault.

Jason: Get the rest of them for $20 a month or $50 a month or whatever. I think she’ll definitely transition to that.

Caroline: Love that. Great first pick.

Jason: Thank you.

Caroline: Yeah. Okay. So are you ready for my pick?

Jason: Yeah. What’s your level of nervousness? One to ten, on sharing your pick?

Caroline: Zero.

Jason: Really?

Caroline: I just think this is fun.

Jason: Okay, great.

Caroline: Okay.

Jason: Calm Business Confidential.

Caroline: Calm Business Confidential. My pick is topical for us because I’m curious if you’ve come across this person in your ecosystem. My Calm Business Confidential is Liz Sharma of Talk the Streets.

Jason: No, never heard of her.

Caroline: I think you have, but I think you maybe don’t recognize her brand name. So, Liz is a Portuguese teacher, but she’s not Portuguese. She, I think, is from London, but moved to Portugal in 2017 from London and studied Portuguese, I think, in school. While she was in school, she came to Portugal many times. I think she lived in Brazil for a while. So studied Portuguese, has been studying Portuguese for, like, 15 years, but like I said, moved to Portugal in 2017. Was training to, I think, be an interpreter, but anyway was a PR professional. So had a typical PR job. Didn’t love, I think, how just that world. And kind of made this big decision to move to Portugal and quit her PR job and now has a business, an online business where she creates content about learning European Portuguese and has a European Portuguese program. But what I love about it is a few things. Well, first of all, I think when I was doing some background research, she started her YouTube. YouTube is the main place that she creates content in order to market her business. And I think I went back to find when she started posting videos, and her oldest video was, like, September of 2019. Okay. So, yeah, it’s been like, roughly four years, but in 2022, at the beginning of 2022, she had 18,000 subscribers. She now has 75,000 subscribers on YouTube.

Jason: Not that the number matters, but we just like to…

Caroline: No, exactly. That’s important to say.

Jason: And the Calm Business Confidential. We’re sharing metrics, we’re having fun, but none of this is like you don’t need to aspire to these things, it’s just to share.

Caroline: And metrics are only to show growth so that you can get inspired. But I think it does serve to show how much you can grow and how that beginning phase is the hardest phase, but then it really does start to get momentum. But a few things I really love about it. Number one, it’s a very simple business, which is she has one program. I think it’s actually like a high I don’t know how much the program is, but it’s a pretty high ticket. A course. Sorry. A course.

Jason: Yeah.

Caroline: Well, I say program because there’s a live component, there’s a community component, whatever. It’s not just like a self guided thing, but it’s one course. Okay. And she uses YouTube as her primary channel. I think she probably does Instagram as well, but YouTube is like the pillar content. Instagram is sort of the micro content to get people to the YouTube channel. It’s a lead magnet, which is a pronunciation guide. I think it does go to like a recorded webinar, which for us personally, we don’t do…

Jason: Watch my live webinar.

Caroline: Live webinar, that’s not my thing, but I like the simplicity of the model. And then the second thing that I really like is I think she’s a good example of overcoming your own self doubt because she’s not a native Portuguese speaker. And what she, I think, realized, and I think in some of her interviews I saw that that was a big hang up for her. She’s like, who’s going to want to learn Portuguese from me when it’s not my first language? But once she identified her audience segment, which is a lot of retirees moving to Portugal, she can relate to them, right? Like she was a transplant. She is not from Portugal. And so not only has she been studying it for 15 years, which to me does give you all kinds of expertise to actually teach people, but then also to say, I know what it was like when I moved here, and it made my reentry or my assimilation so much better because I could speak this, and I know what you’re going through. And I think she used something that could be seen as a weakness, as a strength, depending on the market she chose. I think also I saw she started with some live workshops, like in person. And this is something that we tell people often, which is find a way to kind of like before you create your whole entire course, do one to one, or do some type of live in person thing so that you can get your teaching style down and kind of figure that out. And then the final thing that I think she did really well is from a branding perspective, the name of her brand is Talk the Streets. And her entire thing is about speaking Portuguese in terms of the everyday life Portuguese that you would need in everyday life. Not like you’re in a classroom and you’re learning perfect grammar. It’s how do people on the streets talk in Portuguese? And I think that was a really smart move as well. And in terms of choosing a very big, broad audience segment and then choosing a segment of that.

Jason: How much is her program, just out of curiosity?

Caroline: That I don’t know. All I know is that I did find a blog post that said high ticket. So I’m assuming maybe $1,000, something like that. But to sell it, what she does is she does do a… so once you’re in sort of the lead magnet to here’s my first lesson in webinar format. And then she does a one on one call to see if the program is right for you. And so it’s a high touch selling thing. But I read also that she really likes that because, A, she can make sure that people know a good fit. And the thing that she likes is that personal connection with people and knowing their stories. Why did they come to Portugal? How can I help them succeed in their life here? That’s something that actually motivates her in her business, so it makes sense for her. And again, that’s the whole point of this Calm Business Confidential is what is going to work for you and your life and what you enjoy about online business.

Jason: I mean, that business model for us is, you know, it’s perfect for the space that we exist in, for how we teach people to do things. It’s like create consistent content that’s discoverable, which would be the YouTube channel, have some other content via Instagram. And maybe her Instagram is helping a lot more. But you don’t have to go to Instagram first. You can go to YouTube and you can be there, which I think is very helpful.

Caroline: Well, yeah, and I think it’s smart because she’s already creating, like, if you think of YouTube as her pillar content, she’s spinning off these little breadcrumbs in terms of Instagram reels in a place that’s discoverable, being Instagram, people can search European Portuguese or find certain Portuguese accounts that follow her or reshare her stuff. They get sort of into her ecosystem. I just love the simplicity of it.

Jason: Absolutely.

Caroline: Because if there’s one change that I feel like really made a big difference in the way that we run our business. I mean, of course, now we’ve got one foot and two businesses, but it’s simplicity. So once we moved from multiple different courses, multiple different price points, multiple different everything into everything under one roof, one program…

Jason: Whoever gave us that advice just really did a great job.

Caroline: Great job. No one will ever know.

Jason: Could be a handsome person.

Caroline: Could be a tall person.

Jason: Could be a person who loves baking.

Caroline: But we’ll never know.

Jason: We just won’t know. All right. We hope you enjoyed Calm Business Confidential. That’s our first installment. And maybe what we’ll also do is think about creating a page in the future where we catalog these so that we can come back to them and people can refer back and see the full list because it’ll be hard to keep track of in just podcast notes so we can talk about that afterwards.

Caroline: Also, please, if you have a business that immediately comes to mind of someone who is doing something cool, unique, running a business that doesn’t have the intention of becoming the next billion dollar or 100 million dollar or even million dollar business, but just wants to live a good life, be able to take days off when they want to, and has found a way to do that with an online business, please let us know. Send us an email, You can make the subject line, CBC, Calm Business Confidential.

Jason: Pick the right emoji. Yeah. Also, if you’re going to do that and you think your business could also be a good fit for it, definitely give us some of the details that we’ve talked about here. So we’d love to know some of the backstory story, some of the things. And again, we’re just looking for businesses that have an interesting story that are run calmly, that doesn’t feel stressful. There’s not a hundred employees. Like, you can have a couple employees if you want, that’s fine. But we just want it to be something fun that maybe people haven’t heard about that also gives an inspiration to, like, oh, that’s a business model I can use. An email newsletter that goes to these in depth blog posts that has sponsors and that might have a subscription model, a YouTube channel that goes to a paid program that has this kind of simple funnel leading into getting people to pay for this thing. You know, we like sharing the different business models in this too, because I think it’s fun just to hear about those things.

Caroline: Definitely.

Jason: All right, that’s Calm Business Confidential. We hope you enjoyed it. Now to the pomble.

Caroline: Now to the pomble.

Jason: The Pomble, which used to be the preamble, but now it’s the post preamble, which is now the Pomble. This is where we just share some updates from our life in Portugal. For those of you who don’t know, Caroline mentioned this earlier, but we moved to Portugal. We’ve been living here now nine months.

Caroline: Hard to believe.

Jason: Wow. Nine months?

Caroline: Yeah.

Jason: Pretty soon we’re going to say a year that we’ve been living here, which feels wild.

Caroline: In three months, we’ll say that.

Jason: Let’s get to all the things that we did for the past couple of weeks. But the first thing I wanted to just share is exactly one year ago to the day, we had decided to live here.

Caroline: Really?

Jason: Yeah.

Caroline: How did you know that?

Jason: I just remembered.

Caroline: Okay.

Jason: Isn’t that incredible? We saw one of the places that we’re in, there were a couple of different and we thought, we’re getting a different one, but we didn’t. And we sat in the rental car, do you remember? And we were just like, let’s live here.

Caroline: And I was so scared because I really didn’t think you were going to convince me. I really didn’t. I went in. We’ve talked about this before, but when we came to our little scouting trip in Portugal, I came with an open mind. I told Jason, I promise you, with any big decision like this in life, this is how we operate. Jason’s usually the one who’s like, forging ahead, the accelerator, I’m the brakes. I’m like, Jason, I promise you, I will come into this with an open mind. I’m not going to close the door, but this is going to be a hard sell for me, uprooting my entire life to a completely different country where I don’t know the language, and like, your girl is scared to do that. And I remember after the weeks of being here, sitting in the car, after we toured the place, and I just had this weirdest feeling, one of the weirdest feelings I’ve ever had in my life because it felt so right and I was so happy. But there was this other part of me that was like, I can’t believe he did it. I can’t believe it. I opened that door and I said I would have an open mind, and I was truthful because my mind just got completely changed and holy shit balls are we moving to Portugal.

Jason: And we are. We’re here, and we’re nine months in. So yeah, that’s just funny that that was basically a year ago to the day that we made the decision to live here. Now we’re here, now we out here. Let’s start with we had one Patty, your mom, who visited us for three weeks.

Caroline: She was our first visitor, and she stayed for three whole weeks. And it was really fun to just be able to show her our life here. And I mean, easily the best thing we did was we went to the Doro Valley, which is like the wine region up north.

Jason: Yeah. We were told is the oldest wine region in the world. Now, I don’t know if I can verify that.

Caroline: I don’t know all the research, but…

Jason: It was a three hour drive. Super easy.

Caroline: So beautiful there.

Jason: And just like picture a river.

Caroline: A river.

Jason: But that’s not that wide. You feel like you could throw a stone across it is how wide it is.

Caroline: That’s wider than that but yeah.

Jason: You definitely couldn’t do it. Small cruise ships can go up.

Caroline: And it snakes around, so it kind of curves and then going up from each side of the river, going straight up are just like these rows and rows of…

Jason: Vineyards.

Caroline: Vineyards that are on the side of mountains.

Jason: Yeah, and it’s very mountainous. It’s not like flat. When we were driving, you would be winding up and driving the thing. But yeah, we took her up there. We stayed at just a beautiful hotel with just an amazing view of everything. The food was fantastic, as you would imagine in a wine region. The wine was fantastic in a wine region. We also went to a port winery, which obviously Portugal is very famous for. If you know anything about port in Portugal, it was delicious. We had a little picnic lunch outside. It was just fantastic. But yeah, I think overall, my favorite part of this was just being able to show one of our family members our life here because it’s so different sharing photos or videos or whatever.

Caroline: FaceTimes.

Jason: But actually being here. That’s what I kept asking her while she was here. I was like, does it feel like, wildly different from…? She’s like, no. She’s like, but I love it. She’s like, I get why you guys love it here, and I’m so happy that you’re here.

Caroline: Yeah.

Jason: So, yeah, we just had a really good time showing all of our favorite restaurants.

Caroline: Yeah, so that was basically June with my mom, and then straight into July. We’ve just been trying to take the downtime. As many of you know, when we can, we try to take the summer off. So obviously, if you haven’t had the podcast in your feed, we take off the podcast, we take off the newsletter, and we just give ourselves time to fully recharge. And as life happens to you, we did have some personal things and some family things and had to navigate some stress that we didn’t see coming, which I think has made it a little bit harder to get back into work mode because it’s like there’s more on our plate than normal with personal things. And I hate being so cryptic, but those are not my things to share. But we’ve just been trying to take it day by day, enjoy the sun. Enjoy…

Jason: Lots of little friend hangout things.

Caroline: Lots of friend hangouts.

Jason: There’s just been some Friday night hangouts. Then two new restaurants opened, which is fun. One’s a tapas place, so we really enjoyed that one. And then there’s another new place from one of our favorites that’s like a kind of sister restaurant. So we haven’t been there yet, but we’re excited to go try it.

Caroline: That’s another really exciting thing, is more and more restaurants popping up. Like, you really do get this sense that our little town is sort of like on the cusp, it feels like.

Jason: If we could have a little pour over coffee shop. Oof. It’ll happen when I open it.

Caroline: Jason wants to open a little coffee shop.

Jason: We’ll talk about that later. It’s like a bucket list thing for me. Very small. I don’t even want it necessarily to make money. I just need it to break even so that it can exist for us. We’ll see if that’s a possibility. The last thing to update you on. Where we left you before, we had submitted our residency card paperwork, and we were currently in, like, a waiting period process. We’re still in that process. Now, this is… August is the month that most government agencies, pretty much most companies in Portugal, take off in August. So I think we hit just a weird timing of when our resident cards were supposed to be done. So I’m crossing my fingers that when they come back to work in September, they’re going to be good to go. We have heard nothing. It’s very hard to get a hold of. It’s a government office. So we’re just kind of crossing our fingers and hoping that everything went well. We can’t really do anything about it.

Caroline: Can’t do anything about it.

Jason: We’ll see. We’ll give you an update when we know more. But for now, we’re still kind of in this weird limbo place. But we’re not going anywhere anyway, so we’re super happy to be here. And they can’t kick us out because they don’t even know we’re here. Yeah, that’s pretty much our Pomble this week. If anybody has any Portugal questions, we’re always happy to hear those, and we’ll answer them on the pod. I think that’s all for the updates.

Caroline: That’s it. Oh, my gosh. It feels so good to be back. I missed all of you. Just, like…

Jason: All 17 listeners.

Caroline: 17 of you I really missed, and I’m excited to keep recording.

Jason: Okay. Anything else? You kind of drifted off there, but do you have any…?

Caroline: I just feel. Like, you know, when you to that point on, like, a phone call with a friend where you’re like, all right.

Jason: Well, do you want to say bye or I’ll say bye. Hang up, though.

Caroline: Exactly. That’s kind of how I feel, is, like, I just want to be here with you, but I don’t know how to wrap it up.

Jason: Right. All right, that’ll wrap it up for this episode, and we appreciate you.

Caroline: When in doubt, talk about you don’t know how to wrap it up.

Jason: Okay, that’s it. Bye.

172 – The Next Big Move With Our Software Product (and NEW Segment!)

(Big Fat Takeaway)

We share how we're looking to grow our software product Teachery and have a new segment about calm businesses we've found and want to share.


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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