Jason Fried on Bootstrapping vs VC and Profit vs Revenue

Jason Fried is the co-founder and CEO of 37signals, the company behind Basecamp and HEY.

In this episode, Jason breaks down why they’ve stayed bootstrapped and profitable for 25 years, how they ship without meetings or metrics, and why the best software is always built for yourself first.

He also shares why “working more” isn’t the answer and how 40-hour workweeks can lead to more creative output, not less.

Topics we cover in this episode:
Why Jason never raised VC and still doesn’t regret it
How 37signals builds without north star metrics
Writing as product design: How Jason thinks about good copies
Calm growth vs. high-pressure scale: what actually works
What founders get wrong about retention, pricing, and features
When SaaS stops making sense and why Jason built Once.com
How he’s worked with the same co-founder for 25+ years
Jason’s daily routine, headspace, and rule for “enough”

Perfect for:
SaaS founders tired of the VC playbook
Bootstrappers who want profit and peace of mind
Product leaders designing for real people
Writers and marketers learning to communicate clearly

Connect with Jason:
LinkedIn:   / jason-fried  
Basecamp: https://basecamp.com/
Hey: https://www.hey.com/
Books: https://basecamp.com/books
REWORK Podcast:    • The REWORK Podcast  

Connect with me:
LinkedIn:   / finnthormeier  
Website: https://www.project33.io/
Podcast: https://open.spotify.com/show/03CXzsZ...

Chapters

00:00 Building Calm Companies: Jason’s Story
02:10 Why VC incentives don’t align with calm growth
05:20 What Jason learned from watching SaaS grow aggressive
08:45 Retention hacking, “traps,” and the Basecamp philosophy
10:55 Building for trust, not time spent in-app
13:20 Why Jason doesn’t use goals, OKRs, or north stars
16:30 How Basecamp makes decisions with intuition over metrics
19:10 The writing process behind high-converting copy
22:00 Why product pages are the best content marketing
24:15 SaaS fatigue and the vision for Once.com
27:05 Pricing philosophy: just charge what feels right
29:30 The role of press, story, and staying independent
32:10 How Jason avoids co-founder burnout after 25 years
34:40 Daily structure, creative headspace, and doing less
38:00 What it really means to build for yourself
41:20 Final thoughts: clarity, calm, and doing it your way

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