Top 10 Lessons from 300 Episodes (Plus the Future of this Show)

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It’s episode 300! I thought I’d wax poetic on the top 10 things I’ve learned from both running this show, and the guests I’ve had on. After that, I talk a little bit about what’s in store for How I Built It, and where I’d like it to go in the future. Plus, in the PRO show, I talk about what life without Twitter has been like.

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Top 10 Lessons

  1. Build Your Email List
  2. Talk to your customers
  3. Experiment
  4. Niche/Specialize/Focus
  5. Don’t be afraid to say no
  6. People care about the problem you’re solving. Not you, not the tech you used. The problem
  7. Tell Good Stories
  8. Do things that don’t scale at first
  9. Ship what you have and iterate
  10. Don’t be afraid to ask

Show Notes


Joe Casabona: Did you know that you could get even longer interviews with some of the most successful creators? You can with How I Built It Pro. With How I Built It Pro, you get extended ad-free versions of every episode. We cover things like pricing memberships, how to make a course creation even faster, building a creator business while also parenting, current events, and more.

Plus, you’ll get bonus episodes where I offer a behind-the-scenes look at what I’m working on, the revenue for my own creator business, experiments, and video demos of the tech I talk about on this show. You can join How I Built It Pro today for just five bucks a month or 50 bucks a year. Sign up over at or use the link in your podcast app.

Hey everybody, and welcome to Episode 300 of How I Built It. Now, I’ve got to confess I’m cooking the books a little bit. Because this isn’t actually the 300th episode, episode wise, if that makes sense. If we look at the episode count in Apple podcasts, I actually have 322 episodes. But there have been bonus episodes and trailers and additional stuff that I didn’t count. And it looks like 22, and this is the seventh year, we get about three bonuses a year.

So for the officially official 300th episode of How I Built It, I thought that I would offer you two things. The first is the top 10 lessons I took. Now, this isn’t gonna be a rehash. It’s not going to be an hour-long episode of me going through the lessons. It’s just going to be the top 10 things that I’ve learned in 300 episodes.

And then after the ads break, it’s going to be kind of the future of this show, what I’m thinking about for format and pushing out content continually. Don’t worry, the show’s not going anywhere. I just want to experiment with the show a little bit more than I have been. So that’s what we’ll get into today. And I’m really excited for it.

So for all the show notes, you can go to Super exciting. Thanks to this week’s sponsors. They are Ahrefs, Groundhogg, and LearnDash. You’ll hear about them later on in the show. But for now, let’s get to the intro and then the episode.

[00:02:54] <music>

Intro: Hey everybody, and welcome to How I Built It, the podcast where you get free coaching calls from successful creators. Each week you get actionable advice on how you can build a better content business to increase revenue and establish yourself as an authority. I’m your host Joe Casabona. Now let’s get to it.

[00:03:17] <music>

<clip from 300> Spartan, prepare for glory.

Joe Casabona: I hope you liked that little clip from the 300. Hey, everybody, thanks so much for listening to Episode 300 of How I Built It. I can’t believe that this has gone for 300 episodes. Honestly, I’ll maybe get a little retrospectively in the second part of this episode. But for now, I do want to tell you my top 10 lessons that I’ve learned from 300 episodes of How I Built It.

So this is a top 10 lists. Maybe we can add David Letterman laughing here. Or maybe we can’t. I don’t really use that many sound effects on the show and I’m not a lawyer. But I do want to count down the top 10 lessons that I’ve learned from this show.

So starting at number 10, don’t be afraid to ask. This was maybe the first lesson I learned. And it’s not from the interviews really. I’m sure it’s come up in the interviews. But I learned this while I was booking guests and while I was getting my first sponsor.

So I asked a few fairly high profile people on my show in the beginning. One was Chris Coyier. One was Troy Dean. And they both said yes. One was Peter Hollens later on, and he said yes. And I couldn’t believe it. So don’t be afraid to ask. If there’s somebody you want on your show…

I don’t know if this is like folklore at this point now, but I’ve heard that Seth Godin will go on somebody’s podcast if they’ve had 50 episodes. So like maybe I should ask him to be on the show just to test that theory. But don’t be afraid. If you have somebody who you think is a good fit for your audience and can add value and you know, you think that they’ll get something out of it too, ask them. Don’t be afraid to ask people on your podcast.

Similarly, I got my first couple of sponsors almost like glibly asking if they wanted to be sponsors, and they said yes. And so that gave me the confidence to actually ask people to come on my show and be sponsors. So don’t be afraid to ask.

Number nine, ship what you have in iterate. This is advice that came, I think, most recently from Marie Poulin on her episode. But it comes up time and time again. You don’t want to be a perfectionist at the expense of launching your product, right? So done is better than perfect. Scott Bolinger talks about this really early on. You don’t want to sink like a year of your life into something just to realize that nobody wants it or you’ve been going in the wrong direction.

So instead, ship what you have get feedback and iterate as fast as possible. This is something I’ve really internalized. I’ve seen other creators do it. Brennan Dunn with Palladio, you know, he released that as almost as like a command line tool at first, and then he built out a full dashboard. So ship that you have an iterate.

Number eight, do things that don’t scale at first. This is most recently from Drew Dillon on the latest, on 299. This really hit me because I’m always worried about scalability way before I have to worry about it. And it kind of goes with number nine, ship what you have an iterate. Do something and see if it works. Do a proof of concept. Put up a pre-sale page. Take payments manually. Like just see if people are willing to prove that your idea is good. And part of that is doing things that don’t scale.

So like my membership right now… Actually, ConvertKit just rolled out a new feature called Transaction, so I can better see who’s purchased stuff. But ConvertKit commerce is not the best if you… Like, if you literally just want to sell a thing, like make money selling a thing, yeah, fine, ConvertKit commerce is fine for that. But if you want any other ecommerce related features almost, it’s not really good. It’s not that good. It’s getting better.

But I thought when I relaunched my membership there’s not going to be a site associated with it. I’ve spent way too much time trying to get a good membership site up that I barely update. And so I thought, “You know what? I’m going to sell the membership through ConvertKit. It’s going to be a newsletter. I can connect ConvertKit to Castos for private feeds, it’ll be wonderful.” And there are some missing features.

So like if somebody turns, I have to manually remove them now. But you know what? I shouldn’t let that stop me. I’ll put in feedback with ConvertKit. If I get to a point where the membership actually needs to grow beyond what I have, I’ll do that. But until then, the simplest thing for me to implement is this.

And really, I’m starting fresh, right? It’s a new chapter for the membership. I’ll talk about this in the second half of the episode, but I’m starting fresh and so I wanted to take that to heart. So things that don’t scale at first.

Number seven, tell good stories. This permeates every aspect of what we do online, from defining the pain points for our product, to creating good content, to creating good website copy. Ame Proietti talked about this. Chris Lema talks about this when he was on the show. Lots of people have come on the show to talk about how you need to tell good stories. It’s not just about, “Oh, my product does X, my product does Y, my product’s made with x.” They want the story of how it helps them, what makes them better.

Similarly, number six. Again, this is almost the same exact point I guess, but said differently. People care about the problem you’re solving. Not you, not the tech you used. The problem. So take these two hand in hand. Again, a lot of my early guests were WordPress developers because it was a WordPress development-focused podcast. So one of the things that we talked about was how so many WordPress plugins will be like, “Oh, it’s made with React. Oh, it’s super-fast API’s. Oh, it uses the WordPress REST API.” No one except developers care about that.

What the customer cares about is, does this solve my problem? They don’t care who you are. They don’t care how you made it. They don’t care if you’re just the smartest person in the world. They care about if your product or your service solves a pain that they have. So tell good stories and make those stories revolve around the customer, the hero. You’re the guide, your customer is the hero.

Number five, don’t be afraid to say no. Again, this is more like the business of podcasting. I’ve had a lot of people pitch me to come on my podcast, and I’ve said no. And it was like tough at first because I want my platform to be a good platform for people. But also, my audience is numero uno, right? You guys listening, you’re the number one people for this podcast.

And if I don’t think a guest is a good fit, or they’re going to pitch too much, then I’m not going to have them on the show. I’ve said no at the pitch phase. I’ve said no after they’ve pitched and they’ve scheduled and I just thought it was a bad fit afterwards. I’ve said no while we were on the call getting ready to record.

This happened exactly once. The guy refused to wear headphones. He said it didn’t matter. He was sitting on his couch with the built-in microphone, seemed like he didn’t care. And you know what? If you don’t care, I don’t care to have you on the show. I care. So I said, “You know what?” If you’re not going to take this seriously, I’m not recording. And he was like, “Really?” And I’m like, “Yeah.”

And then he was booked through a podcasting agent, so I told them, “Hey, if you expect to make money off of this guy through published or booked podcasts, you know, he’s not very good. Not very good.” So don’t be afraid to say no.

I’ve also said no to sponsors. I’ve had a couple people especially… I mean, specifically… Well, no, I won’t name them. But I’ve had a couple of sponsors that I’ve turned down because I didn’t think they were a good fit for my audience. One I actually like the product but I don’t think their product aligns with the audience of this show. And so I said no. And you know what? That’s like leaving money on the table. But I don’t think it would be a good fit for them. I didn’t think it would be a good fit for you as the listener. So don’t be afraid to say no.

Number four, niche, specialize, focus. However you want to put it. This is advice that took me far too long to commit to. I started the show in June or July 2016. The trailer came out July 2016. I didn’t take this advice until May 2022. So full six years later. Because it’s scary. But it’s important.

You want to be known for something. You want to be known as an expert in some field. You can’t be that if you are everywhere. Some people can but those people have already built a following. So niche. Niche down. Pat Flynn says the riches are in the niches. Lots of my guests have talked about how you need to specialize, you need to focus your offering. You can’t offer a million things.

Number three, going back to the business of podcasting, experiment. Don’t be afraid to experiment. I’ve changed the shop a couple of times. I’ve made a major pivot from WordPress developers to content creators. Aside from like using technology, which everybody does pretty much at this point, I think these two groups could not be more different.

But you know what? I moved with my own personal interests and I moved with the evolving audience. And there was a dip in the middle but my podcast, this podcast has never done better. Like, double the amount of monthly downloads, and it’s only going up.

So, you know, one was, find the right audience find the right mission statement, and mess around with the format. I used to ask the same five questions for every guest. And then do you have any trade secrets for us? I’ve stopped asking those five questions. I’ve stopped asking the trade secret. I’ve stopped saying, tell us who you are and what you do.” The format of the show is a lot better because of that. Now I’m experimenting with sponsors. There’s only one sponsor break. So experiment, see what works and what doesn’t work, right?

Last year, I tried experimenting with different calls to action, pre-roll, then a call to action, ad breaks, longer intros, longer ads. I got feedback, “Hey, we don’t like that.” So I shortened up the ads, and they do a lot better. So experiment, see what works.

Number two, talk to your customers. This is definitely the second most common piece of advice I get from people on this show, spanning all six years. So it doesn’t matter what niche you’re in, it doesn’t matter what industry you’re in, you have to talk to your customers. Because if you don’t talk to your customers, you don’t know the problems that people are having.

And if you don’t know the problems that people are having, you can’t tell the right story around how you solve that problem. So it could be painful, it could be scary. It probably isn’t. When I go to podcasting events or I give podcasting talks, I offer a free 15-minute consult to anybody who came to my talk. And I ask them, “Hey, what’s your biggest problem in podcasting?” That has helped me immensely. And I know it’ll be the same for you.

And number one, build your email list. Can you believe it? Can you believe that that’s the number one thing I’ve learned from this show? Of course, it is because it comes up all the time. The first time it really came up for me was with Justin Ferriman. I think is the first person who really made me realize I was leaving money on the table by not building my email list.

So no matter what your business client work, sales, products, services, build your email list. Form that relationship. Whether you’re a creator or a car mechanic, make sure you are getting people to opt in to your email list because that is the only true platform that you own. With an email service provider, you can take your ball and go somewhere else. You can’t just take care of Facebook followers.

Heck, if you sell through a marketplace, in many marketplaces, you don’t even get direct customer data. But if people are willingly giving you their email address, you have that. So build your email list. Number one tip now forever and ever until the end of time. Maybe that’s even the trade secret. All right.

So we’ll take a quick break to hear from our sponsors. And when we come back, I’ll tell you about the future of How I Built It.

[00:19:08] <music>

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Sponsor: This episode is brought to you by Groundhogg. Groundhogg is an open source CRM and marketing automation suite for serious agencies, small businesses, content creators, ecommerce experts, and WordPress professionals. Groundhogg allows you to create funnels, automate email, and SMS communications and manage your contacts from the comfort of your WordPress dashboard.

Unlike other SAS CRM platforms, Groundhogg does not charge you a success tax. Groundhogg charges a flat rate fee regardless of the size of your list. Groundhogg will never charge you more as your list grows. It also integrates with all of the top WordPress, ecommerce LMS, and membership plugins to create a unified customer experience.

Start now with a 14-day demo for $1. Go to That’s or use the code HOWIBUILTIT for 20% off your first year of any plan. Thanks so much to Groundhogg for sponsoring this episode of How I Built It.

Sponsor: This episode is brought to you by LearnDash. Look, I’ve been making courses for a long time. I’ve taught at the college level and I’ve created curriculums for several different organizations, including Udemy, Sessions College, and LinkedIn Learning. When I create my own courses, there’s no better option than LearnDash.

LearnDash combines cutting-edge eLearning tools with WordPress. They’re trusted to power learning programs for major universities, small to mid-sized companies, startups and creators worldwide. What makes LearnDash so great is it was created by and is run by people who deeply understand online learning, and adds features that are truly helpful for independent course creators. I love the user experience.

And now you can import Vimeo and YouTube playlists and have a course created automatically in seconds. I trust LearnDash to run my courses and membership. And you should too. Learn more at

[00:22:29] <music>

Joe Casabona: All right, welcome back. So let’s talk about the future of How I Built It. First of all, this show is not going anywhere. It’s evolved over the years. I’m going to continue experimenting. But some of the things that I have planned for the immediate future are putting more effort into How I Built It Pro.

The first thing I want to do here is get more members. And once I hit a certain member threshold, I’m gonna start to do more around that. You know, maybe host some events or put out some extra bonus content. But I need to hit a couple of KPIs to use the business term. But I need to hit a certain number of members at first.

I’m primarily doing that through the pre-roll that you hear at the beginning of the show and promoting it in my newsletter. So I definitely want to make How I Built It Pro a thing. This is probably going to be the way that people can directly support me as a creator if they want to do that. Because, again, if you’ve been with me for a long time, you know that I’ve had many different offerings in many different places. And it’s been kind of confusing. I want that to be simpler.

So my only product right now is the Podcast Liftoff Playbook that is for podcasters or podcasters who want to turn their podcast into a business. And then for this, it’s How I Built It Pro. And those are two different audiences. And I want to leverage that. And I want to see how well I can make membership work. So that’s the first thing I want to do.

I would also love a place for members to congregate. But I have never gotten a lot of traction with that. That hasn’t been requested. And that’s one of the other things I’m trying to do this year is stop answering questions no one’s asking, stop doing things no one’s asking for. So I was like, “Should I set up a Discord? Nobody has asked for a Discord. None of my members have asked for a Discord. So now I’m not going to do the Discord.

Maybe I should do like a weekly wrap-up. I did that for a while. Nobody said anything about it when it went away. So I’m not going to do that anymore. So I’m going to continue to do things as they come, as they get more members, as they get more requests. So that’s number one.

Number two is the experiment that’s currently in progress, putting all of the ad breaks in a row. So what I’m going to do is do this for a few months, and then ask listeners. So I mean, if you have feedback on this already, let me know. I’m going to ask how it works for you and I’m going to ask how it’s worked for my sponsors.

You know, I’ll be like, “Oh, have you seen any change in ROI? Is this something that works for you?” This is a little bit of a scary experiment because I am worried that it’s going to negatively impact my sponsors. But I’ve heard from podcast networks that most people like one ad break. So honestly, if they’re skipping over the ads, anyway, does it matter? Does it matter when they do that? And if they’re gonna listen to the ads, great, they’re gonna listen to the ads. So you know, the logo and the link is on the website, it’s still mentioned in the newsletter. So it’s still getting in front of the same amount of eyeballs that way. So we’ll see.

The third thing I want to do more of this year is the clips shows. So last year, I introduced How I Built Bits, where I would pull out old clips from old episodes, and highlight them. That proves to be far too much work for me. And I didn’t really like it that much.

Plus, I mean, the scope of the show has changed so dramatically that I feel like it didn’t make sense. So I’ve reworked that a little bit this year, and it’s going to be short… I’m aiming for five minutes or less episodes, about tools, tips and tricks for creators. So that’ll be the How I Built Bits, five minutes or less quick tips.

In full transparency, that’s also going to open up another avenue of revenue for me on this show, which was the idea with the Bits show as well. But there’s two ways that these episodes can be sponsored. One is through a micro sponsorship, a pre-roll, that is only for that episode. The other is through a clip series, right? So people can sponsor a mini-series in what will be the Thursday slot, or maybe the Wednesday slot, so it doesn’t conflict with my other podcast.

So what I’m trying to do is make this podcast a little bit more profitable as well. I want to see if I can make it a little bit more profitable. So now I have kind of this mo… I also want to do the experiments for my podcasting students to see what works. But at the core of all of this, and I don’t want this to be lost, is delivering better content and more content for you.

So we have the long-form interviews on Monday, or sometimes we have the shorter episodes where I’m just talking at you for a little bit and then on Wednesday or Thursday, we have these really tight focused episodes where I tell you about make or reader by [inaudible 00:28:31]. And I give you a quick rundown that way. So hopefully, I’m exposing new tools for you. This is another way for me to build in public. That’s the secret mission of How I Built It. If the main mission is to give you free coaching calls from successful creators, the secret mission is show you what I’m doing by building in public. So these bits up episodes, they fulfill that mission.

And then finally, the other thing I’m kind of thinking about is how this show can play nicely with my YouTube channel. Like I said, I want this show to be the like support Joe Casabona way so people can support the content. There should definitely be value. Don’t just give me… I mean, if you want to give me money because you like what I’m doing, that’s great. But I do want there to be value. You know, I do the live streams. It’s called Build Something Live. It’s part of the building in public mission. So I want to figure out how I can make both of those play nicely.

I do have memberships available on my YouTube channel now. So if people just want access to member-only videos there, they can pay three bucks a month versus the five bucks a month to be at How I Built It pro membership. The main difference is, you get those videos, and you get the ad-free extended episodes of the podcast.

But I want them to play a little bit more nicely, right? It would be cool if YouTube had a way for me to make somebody a member without having them pay for it. But you know, they want everything in their ecosystem, they make it very easy for creators to monetize. And I get that. So that’s something for me to think about.

And along with that, I’ve been getting a lot of feedback, positive feedback about the automation content I put out. So in looking at what to position or further niche myself into podcasting, as well as what am I doing building in public, it feels like automation can be this bridge for both of these. But again, this is me thinking out loud.

The concrete plans are get more people into How I Built It Pro. That’s at Make that a more valuable membership and community of listeners who are trying to build and public. Figure out the best way to bridge the gap between the YouTube channel, like the building public stuff on the YouTube channel, and the membership. And reintroduce clips in an appreciable way, where it provides value for the listener, it provides an additional revenue stream for me, and it provides additional value for my current brand sponsors.

So that’s what I’m thinking about. I would love your feedback on all of this. And this is the other thing. Since I’ve left Twitter, I’ll talk about that and How I Built It Pro… I don’t think I’ve talked about that on the show yet. Because I think since I left… I’m pretty sure since I left, I’ve had scheduled episodes. Anyway, I’ll talk about that How I Built a Pro.

But since I left Twitter, I need a new call to action for the end. I can’t say, “Like me on Twitter” anymore. So I’ve created a feedback form. I’m stealing that idea from Relay FM. But it’s at It’s a form. You can submit questions, comments, concerns, you can tell me how wrong I am about stuff and I’ll read it on the show. And you can even mark it as like, “Please make this anonymous.” I guess that’s the last thing I’ll mention. Again, in How I Built It Pro, I’ll talk about why I left Twitter and how it’s been. Because I do have a blog post on that. But it’s been like two weeks since I left now.

So that’s it for this episode, Episode 300 of How I Built It. Thanks for joining me. Thanks for indulging me a little bit. I’d love to hear what you think. You can find the feedback form as well as the button to sign up for How I Built It Pro and everything we talked about over at

Thanks so much to the sponsors of Episode 300. They are Ahrefs, Groundhogg, and LearnDash. Thank you so much for listening. If you’re a member, I’ll see you in the pro show. Otherwise, until next time, get out there and build something.

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