Skip to content

What's the worst that could happen?

July 29, 2026 · 26 min

Show notes

Many entrepreneurs spend more time worrying about what could go wrong than actually finding out. In this episode, Jason Fried and David Heinemeier Hansson detail how 37signals approaches experimentation, why lowering the stakes on most decisions leads to better ones, and how letting go of outcomes is both a mental discipline and a business strategy.

Key Takeaways

  • 00:10 – Where the willingness to just try things comes from
  • 02:40 – The freedom that comes with not having to cover your bases before every decision
  • 08:51 – Nobody can predict how customers will react
  • 13:04 – How long do you give something before moving on?
  • 18:01 – Things don't always pan out
  • 21:29 – Anything you build can roll forward into the next product idea

Links and Resources

All episodes of REWORK

Settings

Display

Language

Decides which stations you see first on the home page.

History

Recently played stations and episodes and your latest searches are only stored in this browser.

Notifications

A short notice when a podcast you follow has a new episode. Turn off single podcasts with the bell on their page.

Account

Save favorites – in the app and on the website.

Keyboard shortcuts

/
Open search
Space
Play or pause
← →
In the player: back 15 s, forward 30 s (episodes) · in a row: next tile
↑ ↓
In a row: target within the tile
Home / End
In a row: first or last tile
Esc
Close window or menu
?
This overview
Now playing

Go to station page

Play next

    Add episodes with “Play next” – they play after the current episode.