I'm the co-founder of Transistor.fm (podcast hosting and analytics). I write about SaaS marketing, bootstrapping startups, pursuing a good life, building calm companies, business ethics, and creating a better society,.
Reasonably unreasonable
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"Never tell me the odds." – Han Solo, Star Wars. What are the odds?Yesterday, I watched my favorite hockey team (the Edmonton Oilers) lose to the Florida Panthers in the Stanley Cup finals. Every season, all 32 NHL teams have the same goal: "Win the Cup." But only one team can win. Even a strong team (like the Oilers) has only a 12% chance of winning. Put another way: they had an 88% chance of not winning. What are your odds?A founder building a new startup also faces daunting odds. As Jason Cohen says: "[Startup success] is rare and risky. [Many] people who are equally smart, equally deserving, equally privileged, and work equally hard often don’t make it." US data shows that only 20–30% of all new businesses are operating and profitable after 5 years. Why play the game?Given NHL playoff odds, what drives the Oilers captain, Connor McDavid, to strive for the Cup each year? Likewise, given your odds of success as an entrepreneur, what should drive you to start companies? Perhaps it's the same sentiment that drove NBA superstar Michael Jordan: "I can accept failure; everyone fails at something. But I can't accept not trying." What increases your odds of success?I like Kevin Smith's answer: "[Success] requires a reasonable amount of unreasonability. Not like, "Hey, man. I'm going to jump off a building and fly without the aid of a jetpack." That's unreasonable unreasonability. Reasonable amount is just like, "You know, why not me?" This is the first attribute: having just enough "unreasonable" belief in yourself. The second attribute you'll need is similar. I'm going to call it: "A reasonable amount of relentlessness." Jason Cohen says, "Before they were successful, every founder started out unsuccessful." What distinguishes founders who were (finally) able to build a profitable startup? Relentlessness and drive, tempered by realism. This means you're the kind of person who doggedly pursues a higher goal ("I'm going to build a profitable company to give me and my family a better life"), and you know it might take multiple bets to get there. Also, these have to be reasonable bets; you can't afford to make bad bets (because every startup costs you time, energy, and money). Finally, successful founders cultivate the skills, insights, connections, and resources they'll need to give them a shot at success. So, if you "can't accept not trying," focus on being:
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Justin Jackson's SaaS marketing experiments
I'm the co-founder of Transistor.fm (podcast hosting and analytics). I write about SaaS marketing, bootstrapping startups, pursuing a good life, building calm companies, business ethics, and creating a better society,.
When I got to the address, the door looked like this: sketchy However, once inside, I was surprised to see an incredible podcast recording studio: Justin and Nathan at Kit studios On April 1st, Nathan Barry (founder of Kit) asked me to join him in an industrial area of Chicago to record a podcast. This was for the opening of the new Kit Studios in Chicago. Even cooler: anyone with a Kit account can use it. (I'm told the outside is much nicer now. 😉) Nathan and I sat down, and he interviewed...
Overall, I've been pretty unimpressed with many of the promises coming from the "AI code bois." I got tired of watching video demos that hyped things up, only to try it myself and be disappointed. But after this conversation with Adam Wathan (creator of Tailwind CSS) and Brian Casel (Instrumental.dev), I'm starting to see AI development differently: I was surprised that Adam is this bullish on AI dev tools: "I used to be more skeptical. But then I forced myself to download Cursor and build an...
I want to hear from you. This week, I'm sharing 3+1 bite-sized thoughts, ideas, and prompts. Hit reply here, or on Bluesky, with your thoughts! ------- 📺 🗡️ Will YouTube kill the podcast industry? I've been thinking and writing a lot about YouTube, podcasting, and open protocols (RSS) vs big centralized platforms. Read my post | Reply on Bluesky (If you're of a "certain generation" and you're thinking, "who uses YouTube for podcasts?" you might want to read this draft I'm working on) -------...