How to build a business that lasts | Jason Fried (CEO & Co-founder, 37signals, Basecamp, HEY)
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Welcome to Subscription Heroes. I'm your host, Scott Herf, co-founder and Chief Product Officer of Churnkey. Not every day you get to chat with a legitimate legend, that's why I'm thrilled to share my conversation with Jason Fried, co-founder and CEO of 37signals, makers of Basecamp and Hey, and best-selling author of four books on work, design, and building calm companies. We kick things off by talking about his recent sabbatical.
What Jason Fried Learned From His Sabbatical
Scott: Jason, you're coming off a four-week sabbatical, the first in a long time. Now that you're back, what's been most on your mind?
Jason: It's been great to confirm that the company can run without me; not that I doubted it, but it's confidence-inspiring. You build a great team, and things keep moving. I'm not essential, and honestly, no one really is. Beyond that, stepping away gave me fresh eyes. Even the messaging I wrote myself started to look a little dull. You need distance to see things clearly again.
Scott: Did you get into anything inspiring during the break, biographies, anything like that?
Jason: I read a couple of books, but nothing business-related. Mostly, I went on long walks and tried not to think about anything intentionally. I had plans at first, drum lessons, learning Spanish, but then I realized that was just more work. Once I let go of the agenda, it became a real break. I also went on some long drives, something I hadn't had time for in years. It took about a week or two to decompress from the momentum of always being busy.
Jason Fried's Watch Collection
Scott: I know you used to be a watch collector. I still think about that Instagram feed from 2016–2017. Are you still into watches?
Jason: I still love watches. The Instagram phase was interesting. I found myself showing things off, which isn't really my style. Social pressure, even from thousands of strangers, starts to shape your behavior in ways you don't intend. So I stepped back from that. I tightened my collection; I'm down from about 40 to around 25, which is still too many. My rule now: if I haven't worn it in three months, it probably needs to go. Vote with your wrist.
Jason: I'm still following the watch world. Watch Wonders is happening in Geneva right now, and I'm tracking it from afar. I still love Longines and Speedmasters. I went through a vintage Rolex phase, tried some modern pieces, and have settled into a more focused collection.
Scott: I've got a 1970 Speedmaster, the transitional caseback.
Jason: Nice, that's a good one. Today I'm wearing an IWC, the Tribute to the 3705. The original from the '90s was 39mm, the modern version is 41mm. It's made of a bio-ceramic material, ceramic, and titanium, and I've really come to love it.
Scott: I've been wearing a WWII-era A-11, tiny at 19mm. You mentioned Longines and IWC; they made the Flieger pilot's watch, which is on my dream list, though the radium lume puts me off.
Jason: Same. I was looking at an early '60s Submariner just an hour ago and asked the dealer to check it with a Geiger counter. It came back still radium, and I passed. There are so many great watches out there that aren't radioactive. No need to strap one to your wrist.
Churnkey's Message
Churnkey is the platform that fixes every type of churn for you. We handle retention for customer-obsessed teams, lowering cancellations by up to 42%, recovering up to 89% of failed payments, and increasing customer LTV by 28% through cancel flows, failed payment recovery, and AI-driven feedback analysis. Head to churnkey.com to get started.
How to Write for Business Without an Audience, Schedule, or Formula
Scott: Let's talk about writing. You still write a tremendous amount. Do you write for yourself, or always with an audience in mind?
Jason: I write what I'd want to read. If I'm writing something, it has to be something I wish existed. Some pieces take five minutes, some take a week of thinking; it just depends. The best ones tend to flow out in one go, almost like a conversation. My core principle: write for yourself, not for imagined readers. You're never really good at predicting what other people want. Share the ideas you wish you'd heard; that's enough.
Scott: What's your process when it's not a one-and-done piece?
Jason: For something permanent on the site, like the "Small" page on basecamp.com, I'll share it with David and get feedback. But for posts on Hayworld, LinkedIn, or our old Signal vs. Noise blog, I almost never show anyone in advance. It's just my thought, put down as-is. I don't write on a schedule; sometimes weeks go by without a post, other times three ideas hit at once.
Jason: One thing I've been wanting to write about: performance reviews. People always ask how we do them at 37signals. For me, it comes down to one question: after about a year, would I hire this person again? If the answer is yes, great. If not, that tells you everything. I find these simple questions that collapse a lot of complexity into a single, clear answer. That's the piece I want to write.
Scott: You still write all of Basecamp's key marketing pages yourself?
Jason: Yes, the landing page, pricing, how it works, that's me. It's actually what I enjoy most: coming up with new ideas and then finding the right language to connect with people who are shopping for them. I've stepped back from design execution, HTML, and CSS, but writing is still my primary contribution.
Scott: Does a new feature ever originate from the copy, from writing the UI first?
Jason: Always. The pitch is always written, never performed. There's no meeting where I explain the idea; it's written down, maybe with a few sketches to support it. And a big part of defining any feature is figuring out how you'd write the screens, how you'd explain what it does. If we can't describe it clearly, the feature probably isn't ready.
How to Compete With Funded Competitors
Scott: That clarity feels like a big part of your staying in power. You started competing against Microsoft Project, and now you're up against VC-backed competitors burning hundreds of millions. What's your playbook for staying relevant after almost 25 years?
Jason: Honestly, I'm not entirely sure, but I have a few ideas.
First: run a profitable business. You can will yourself into existence for a while, but reality will catch you. We keep headcount small, keep costs low, charge real money for our products, and focus on delivering genuine value.
Second: have a unique point of view, and marry it to a philosophy people can buy into. Using Basecamp or Hey means opting into a certain way of working.
Third: share without expectation of return. We've written books, blog posts, done podcasts, shared design decisions, and code openly for years. And we're not beholden to outside investors pushing toward an exit. We started this business to stay in business, not to leave it.
About AI Tools for Business: What Works and What is Still Overhyped
Scott: Being long-term focused also means you're not chasing hype trains. Which brings me to AI. You've said before that computers will eventually program themselves. How are you thinking about AI right now?
Jason: It's real, and it's a real shift. Right now, I think it's most useful for summarization, refinement, and surfacing certain insights. The text side is interesting but still somewhat novel. ChatGPT has a voice, and you can kind of tell where things came from. What I think will be genuinely transformative is when AI becomes truly personal; something that understands your style, your tone, how you'd respond to a given situation. A real second brain. Until then, it's fascinating, but I'm not sure how we'd use it in the way we work. We don't write 90-minute meeting transcripts that need summarizing. That's just not us.
Jason: What excites me more right now is Midjourney, the visual side of AI. I produced a series of images reimagining Nighthawks, the Hopper diner painting, with robots, and the output was just beautiful and hilarious at the same time. What's exciting to me is that writers can now paint. I can't draw. My wife is a talented artist, and I've always been envious of that. But now I can describe something and watch it appear. That's extraordinary.
Scott: My take is that the role of the editor, the person with taste, is going to become more important than ever.
Jason: Completely. Think of it like directing. There's no shortage of great screenplays or brilliant ideas, but great directors are rare. They pull off the right lighting, the right expression, the right tone. Prompting AI is directing. And not everyone will do it well, which means taste and judgment become the real differentiator.
Scott: What about the kids? Are they aware of this stuff?
Jason: My son is eight, and we've played around with ChatGPT and DALL-E together. It's going to be mind-blowing in three to five years. Video generation is next, then AI scoring music to match your visuals exactly. These are just tools, like computers were tools, and they're going to unlock a lot of imagination and let people do things they could only think about before.
Final Thoughts: What Would You Do If Work Could Wait?
Scott: Last question: what's the most ridiculous or improbable thing you want to do that you don't think you ever will?
Jason: A three-month silent retreat. I'd love it, and right now it's completely impossible: kids, company, life. Maybe in 12 or 15 years, but then will I even want to do it for who I am then? That's the real question. There's a big part of me that craves it now.
Scott: Mine is performing with Metallica. I love heavy metal, I play guitar, and I'm actually putting pieces in place to make it happen, somehow.
Jason: I think privately would be way cooler anyway. Get in there, be a roadie, work your way up.
Scott: Thanks so much, Jason. This has been a great conversation.
Jason: Thanks, Scott. It was fun.
About Jason
Jason Fried is co-founder and CEO of 37signals, the makers of Basecamp and HEY. He's a best-selling author of four books about work, design, and building calm companies.
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About your host, Scott Hurff
Scott Hurff is a co-founder and Chief Product Officer at Churnkey. He was on the founding team of Tinder’s first acquisition, where he created some of the app’s most successful early revenue features. He was on the founding team of Casa, the world’s first consumer-friendly Bitcoin self-custody provider. O’Reilly published his book, Designing Products People Love, which Scott Berkun called “a thoughtful and charming guidebook for making great things.”
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