Antifragility and Expecting Hard Times

David Heinemeier Hansson (DHH) is the co-founder & CTO of 37signals (Basecamp, HEY) and the creator of Ruby on Rails.

In this episode, DHH breaks down how he built real wealth without playing the Silicon Valley game, why “fuck you money” is misunderstood, and what it really takes to stay independent for 20+ years.

We talk about effort, writing, grit, parenting, and how the most meaningful success doesn’t always look like a unicorn.

Topics we cover in this episode:

- How Basecamp started as a side project and became a 20-year business

- What most people get wrong about building “fuck you money”

- Why DHH bet on Ruby when no one else cared

- The 2% rule: how David outworked luck

- The real cost of deferred living and why it’s not worth it

- Why content creation is a byproduct, not a goal

- What Europe gets wrong (and right) about work and family

- Why blogging and replying to people still matters

Perfect for:

- Founders who don’t want to raise $100M to be successful

- Indie hackers and devs building side projects

- Creators who actually ship things

- Anyone tired of the same recycled startup advice

Connect with DHH:

- DHH’s Linkedin: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/

- DHH’s X: https://x.com/dhh

- DHH’s blog: https://world.hey.com/dhh

- DHH’s personal website: https://dhh.dk/

- 37signals: https://37signals.com/

- Basecamp: https://basecamp.com/

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

- Once: https://once.com/

- Ruby on Rails: https://rubyonrails.org/

Connect with Finn:

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

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

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

Chapters

00:00 – Intro: Why wisdom becomes platitude

01:58 – The watch blog that changed lives

03:20 – What “fuck you” money really means

06:31 – Betting on Ruby when it made no sense

09:50 – Why Building for yourself means long-term leverage

11:45 – Don’t wait to live your dream

14:20 – DHH’s 2% mindset (via David Goggins)

16:45 – How one helpful email led to 37signals

18:20 – Redrawing patterns: giving gifts with no ask

20:40 – Standing out: The 0.1% effort rule

23:55 – “Content creator” is an insult. Here’s why

25:40 – Share your ideas *after* taking action

27:15 – Marketing without ads or attribution

29:40 – Gary Vee and the power of retail scale

32:00 – Jim Rohn, Stoicism, and seasons of life

35:10 – How to survive the storm

37:05 – Platitudes only work when they land

38:30 – Authenticity means being maskless

41:20 – On “fuck Apple” and reputation caveats

42:40 – Why compliments should be clean

44:30 – Balaji, network states, and philosophy

47:00 – Europe and ambition shame

50:40 – Cultural change is possible (but slow)

53:00 – Bringing success back home

55:30 – Final thoughts: Be the 2%. Always.

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