KDAV Radio

REWORK - What's the worst that could happen?

July 29, 2026·25 min
Episode Description from the Publisher

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 Takeaways00:10 – Where the willingness to just try things comes from02:40 – The freedom that comes with not having to cover your bases before every decision08:51 – Nobody can predict how customers will react13:04 – How long do you give something before moving on?18:01 – Things don't always pan out21:29 – Anything you build can roll forward into the next product ideaLinks and ResourcesJeff Bezos explains one-way door decisions and two-way door decisionsRecord a video question for the podcastWatch The REWORK podcast on YouTubeBasecamp is the no-nonsense project management system. Sign up for free at Basecamp.comHEY is a fresh take on email. Sign up for a 30-day free trial at HEY.comFizzy is a modern spin on kanban. Sign up for free at fizzy.doBooks by 37signalsJason Fried on XDavid Heinemeier Hansson on X

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