How I Built It was a short interview show — 30 minutes at most — built on the same five questions every time, ending with "do you have any trade secrets for us?" The predictability is what made it work for the first hundred-plus episodes, the way a procedural show gives you a format you can settle into. The question that mattered most was the one about failure, because in 2016 everyone was talking about their wins and almost nobody was talking about what went wrong. I'll admit past me used "I like to be surprised along with my guests" as an excuse to skip research, and I don't agree with him anymore.

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I bought the domain howibuilt.it on my honeymoon in Italy, purely because every site I saw there had a .it address and I wanted one. The idea arrived a few weeks later: I was relaunching my online courses, having great conversations with people about how they'd built their businesses, and realized I should be recording them. How I Built It launched in July 2016 — less sloppy, better researched, and aimed squarely at independent developers who wanted to start a business, which is to say, at me. People say good ideas come back to you. I don't believe that. Write them down and revisit them.

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Going on ShopTalk Show with Chris Coyier and Dave Rupert around 2013 changed how I made podcasts. They had a guest notes page explaining how to get the best possible recording, and they had guests record their side locally so the finished episode sounded like everyone was in the same room — years before Riverside, Zencastr, or SquadCast existed. That one appearance is a large part of why my next show sounded good enough to take off. Spend time in the space, take the good lessons, and apply them.

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• ShopTalk Show — shoptalkshow.com
• Riverside (affiliate link) — joec.pro/riverside
• Ecamm (affiliate link) — joec.pro/ecamm
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The TIL Podcast failed because I wasn't serving anybody. The technical barriers are gone — you can record from your phone, and RSS.com has a free hosting tier (disclosure: I'm their evangelist, and the link below is an affiliate link) — which means serving a specific audience is now the whole job. Write a mission statement, pick someone real and specific, and talk to them. You don't need millions of downloads; you need people you serve well enough that they come back and bring others.

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After ending the TIL Podcast, I rebooted it as an interview show — I'd talk to friends about their professional lives, starting with Dr. Dan Ostermeier and my brother, who worked at Disney World. It lasted two episodes, because I had no mission for it beyond wanting to make podcasting work. This was before Serial and Lore pulled podcasting into the mainstream, and I still had no reason for the show to exist. Two failed experiments with the same show taught me more than a cautious success would have.

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We made it about six episodes before the TIL Podcast fell to podfade. There were too many of us, we all had full-time jobs, the moderation was loose, and we never carved out a niche that would have made the show worth continuing. When our schedules shifted, we called it — and I asked everyone whether I could keep the name, which nobody minded. Know when to stop, and don't let sunk cost make the decision for you.

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After three days of talking about the TIL Podcast, I dug through the archive to find the very first thing we covered on that show: Coin, a connected card that was supposed to replace every card in your wallet. Apple Wallet and Google Wallet killed the product, but the domain is still live — now pointed at beginner crypto guides. Whoever is running it started sloppy, did their research, and iterated, which was not the tie-in I planned when I started digging.

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Almost nothing in podcasting is permanent. Your format, your approach, and what you cover can all change, and my early show did get better as my friends and I kept adjusting. More importantly, what I learned making it is what let me launch several successful shows later. (For anyone who hasn't heard the term: TIL stands for "today I learned.")

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