If Jason Started Over in 2025

Jason Fried is the co-founder of ⁨37signals the company behind Basecamp and HEY, and a pioneer of calm company building.

In this episode, Jason explains why he doesn’t chase trends like AI, how 2-person teams launch new products inside 37signals, and what it really means to build with taste, not speed.

Topics we cover in this episode:

- Why Basecamp hasn’t added AI, and why that’s not a problem

- How Jason avoids FOMO, even as trends explode

- Why 37signals builds multiple products with just 60 people

- What “product taste” really means—and how to hire for it

- The future of craftsmanship in a world of AI

- Jason’s unstructured workdays and creative flow

- How he’d build if he started from scratch in 2025

- Why content ≠ content, and how writing built 37signals’ brand

- When to ship vs. when to keep building

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Connect with Jason:

- LinkedIn: https://www.linkedin.com/in/jason-fried/

- Basecamp: https://basecamp.com/

- Hey: https://www.hey.com/

- Books: https://basecamp.com/books

- REWORK Podcast: https://youtube.com/playlist?list=PLwo5Hcps5IkBBAv1-_HPOMvC4Rn1p8lsQ&si=7tq91JJ-GS4pgY1v

Connect with me:

- LinkedIn: https://www.linkedin.com/in/finnthormeier/

- Website: https://www.project33.io/

- Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH

Chapters

00:00 Why Basecamp hasn’t added AI, and how Jason thinks about it

03:20 Avoiding FOMO and chasing trends

05:50 What Jason would do if he had to start from scratch

08:00 Making multiple products with just 60 people

10:18 How 2-person teams launch new tools at 37signals

12:00 The story of a product they killed—and why

14:30 Does SaaS still have room for new ideas?

16:15 The real opportunity: simpler software

18:30 Why trades might be the most future-proof jobs

20:05 The future of craftsmanship in an AI world

22:10 Jason’s spontaneous workdays and unstructured flow

24:45 What makes a good day at work

26:15 When to ship vs. when to keep building

30:00 How to make decisions without chasing competitors

33:00 Why Jason hates the term “content”

34:45 Writing, trust, and brand building the 37signals way

37:00 Redesigning products without alienating your users

39:30 Jason’s philosophy on culture: it emerges, not planned

43:00 Taste, talent, and how 37signals hires designers

49:00 What taste really means—and how to spot it

51:30 Jason’s favorite products: from V-Drums to a 1978 Porsche

54:00 Why legacy doesn’t matter (and ego does)

56:30 What Jason would prioritize if building a village

63:00 New book teaser: Make It Up As You Go

Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH

LinkedIn: https://www.linkedin.com/in/finnthormeier/

Website: https://www.project33.io/

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