What Jason Fried Learned from 26 Years of Building Great Products

Jason explains how his aesthetic appreciation for watches, cars, and especially architecture shapes his approach to product design. He discusses the importance of honest materials, ergonomics, and creating products that feel like complete wholes rather than assembled blueprints.

• •Great products share qualities with well-designed physical objects: attention to scale, materials, tactile experience, and ergonomics
• •Buildings made with natural materials often feel better in person than in photos, unlike modern architecture which photographs well but disappoints physically
• •The best spaces are often designed by people who will actually use them (Christopher Alexander's 'unselfconscious design')
• •Handmade, non-architect buildings often have more soul and character than professionally designed spaces
• •Software design should aim for the same deep satisfaction as being in a great building, despite the limitations of flat screens and pixels

Discussion of AI's role in building products, comparing it to FileMaker Pro for rapid personal tool creation. Jason expresses skepticism about AI's ability to handle the edge cases and complexity of building for multiple users, while acknowledging its power for individual productivity.

• •AI excels at building personal tools quickly, similar to how FileMaker Pro enabled non-programmers to create databases
• •The real art of product development is handling edge cases and multiple user scenarios—where AI currently struggles
• •Professional developers using AI tools can achieve significant productivity gains across the entire development lifecycle
• •Despite AI tooling advances, there's a notable absence of breakthrough standalone products (beyond AI tools themselves)
• •The gap between AI's promise and market reality suggests technology alone isn't the bottleneck—organizational adoption and vision matter

Dan shares Every's model: 15 people running 4 AI products plus consulting, generating millions in ARR. Each product is built by a single person using AI tools, demonstrating a new paradigm for small team productivity that would be impossible without AI.

• •Every runs 4 software products with single-person teams, serving thousands to tens of thousands of users each
• •The entire operation generates millions in ARR with just 15 full-time people—impossible without AI
• •Programming has fundamentally changed in the last 3 months—coding now happens in English, like pseudocode
• •Small companies built ground-up with AI-first approaches will eventually outcompete traditional organizations
• •Similar to the Internet in late 90s, breakthrough companies exist but are still small—we're in very early innings

Jason reveals that 37signals programmers prefer writing code by hand, viewing it as craft like poetry. They use AI for lookups and learning but not for code generation, highlighting the tension between traditional craftsmanship and new AI-powered workflows.

• •37signals programmers value the craft of hand-writing code and will likely continue this throughout their careers
• •AI is used around the edges: looking things up, learning new concepts, API calls, some boilerplate
• •Using AI for coding can atrophy traditional programming skills—a tricky balance if you value those skills
• •Different organizations will adopt AI differently based on their culture and what skills they value
• •The hype around AI productivity doesn't yet match the visible output in the product market

Jason reflects on his earlier arrogance about luck and now believes success is 'almost all luck.' He details specific lucky breaks: being born in 1974, graduating in '96 during the internet boom, meeting his business partner online, and getting early opportunities like designing Meetup.

• •Early in career, Jason didn't believe in luck—now realizes 'it's almost all luck' combined with doing good work
• •Being born in 1974 meant graduating college in 1996 when the public internet launched—perfect timing
• •The internet created a rare moment where everyone started from scratch with equal knowledge
• •Chance encounters shaped everything: neighbor showing him a Mac at 13, meeting David online, designing Meetup leading to Groupon board seat
• •You still need to do the work and be good, but many people do good work—luck and timing determine who succeeds

Jason shares how his priorities shifted over 26 years: he's now far less interested in running a business and more focused on making products. The business is just necessary infrastructure to build products—he fancies himself a product maker who happens to be an entrepreneur.

• •Running a business is 'not that interesting' to Jason—he's fundamentally a product maker
• •The business side (pricing, hiring, organization) is necessary but doesn't drive him
• •Basecamp generates enough cash to provide flexibility and fund other product experiments
• •If not doing this, Jason wouldn't start another business—starting businesses isn't exciting, making products is
• •Like John Mayer writing lyrics because guitar would sound weird without them—business is necessary but not the point

Dan seeks advice on scaling Every (15 people, $1-3M ARR, 50% quarterly growth). Jason's core advice: keep doing what got you here, don't hire someone to 'run the business,' and avoid making other people's mistakes by trying to be someone you're not.

• •Nobody has experience running YOUR specific business—you know the source material better than anyone
• •It's perfectly okay to make it up as you go—that's what everyone does, but you have the advantage of knowing why decisions were made
• •At 15 people, the business and product are inseparable—you can't just focus on creative while someone else runs operations
• •37signals tried hiring COOs multiple times but realized at small scale, it's all one holistic thing
• •The biggest mistakes come from doing things because you think you 'should'—stay close to who you are and what you want to do

Both Jason and Dan share that their worst decisions came from doing things because they thought they should, not because they wanted to. Dan stopped writing to 'be a CEO,' leading to years of flatness and misery until he returned to writing half-time.

• •Most bad decisions come from trying to be someone else or doing what you think you're 'supposed' to do
• •Making other people's mistakes by following conventional wisdom leads to instability—there's no foundation of meaning
• •Dan spent 2-3 years flat and miserable after stopping writing to 'be a CEO'
• •In the age of undifferentiation (everything looks the same), being yourself is the only competitive advantage
• •If you're going to fail, fail being yourself—that's a great way to go down, not pretending to do the 'right' thing

Jason articulates his core philosophy using Frank Lloyd Wright buildings as the ultimate example: the best products are complete, indivisible ideas where every piece belongs and nothing can be replaced without destroying the whole. This spiritual approach to product-making comes from experiencing great architecture, watches, and furniture.

• •Frank Lloyd Wright buildings are complete ideas manifested in materials—you can't replace the sink or repaint the floor without destroying the vision
• •Great companies are the same way—you can't tease them apart and replace big pieces without losing what makes them special
• •Some houses are just assembled pieces where you could swap windows—those aren't as great as indivisible wholes
• •Experiencing complete ideas in physical form is a spiritual experience that guides product-making
• •Society is becoming less willing to invest in complete ideas, leading to more pieced-together products that look good but don't feel as good