REWORK

Not every decision deserves a long deliberation. In this episode, co-founders Jason Fried and David Heinemeier Hansson look back on 25 years of running 37signals, the handful of decisions that were truly irreversible, and why keeping a loose grip on most business calls has served them better than any spreadsheet ever could.
Key Takeaways
00:11 – The single one-way door decision at 37signals
05:49 – Why most decisions barely take five minutes to make
08:05 – How the sum of right choices matters more than any single one
13:51 – Recognizing when the business stops moving forward
16:41 – Letting go of decisions that didn't pan out

Links and Resources
Jeff Bezos explains one-way door decisions and two-way door decisions
Record a video question for the podcast
Watch The REWORK podcast on YouTube
Basecamp is the no-nonsense project management system. Sign up for free at Basecamp.com
HEY is a fresh take on email. Sign up for a 30-day free trial at HEY.com
Fizzy is a modern spin on kanban. Sign up for free at fizzy.do
Books by 37signals
Jason Fried on X
David Heinemeier Hansson on X

Fresh listener questions are on the table this week. Jason Fried and David Heinemeier Hansson tackle whether small builders can realistically compete with industry heavyweights, what the AI agent wave actually means for the future of SaaS, and whether mixing your personal social presence with your business is a smart move or a mistake.
Key Takeaways
00:11 – Competing in a market dominated by big players
04:40 – Is AI really the end of SaaS as we know it?
15:52 – When it makes sense to build versus buy
17:43 – Personal social accounts and promoting your business
Links and Resources
Record a video question for the podcast
Watch The REWORK podcast on YouTube
Basecamp is the no-nonsense project management system. Sign up for free at Basecamp.com
HEY is a fresh take on email. Sign up for a 30-day free trial at HEY.com
Fizzy is a modern spin on kanban. Sign up for free at fizzy.do
Books by 37signals
Jason Fried on X
David Heinemeier Hansson on X

No prep, no filters, just questions. Host Kimberly Rhodes puts Jason Fried and David Heinemeier Hansson on the spot with a fresh round of rapid fire questions covering everything from recent reads and AI discoveries to memorable customer service moments and what they've started or stopped doing to make work better.
Key Takeaways
00:10 – Recent books worth reading
02:13 – Something surprisingly good about AI right now
08:36 – A standout customer service experience
12:36 – Something started or stopped that made work or life better
14:21 – A favorite part of a typical work week
Links and Resources
Something Deeply Hidden by Sean Carroll
The Fourth Turning by William Strauss and Neil Howe
Record a video question for the podcast
Watch The REWORK podcast on YouTube
Basecamp is the no-nonsense project management system. Sign up for free at Basecamp.com
HEY is a fresh take on email. Sign up for a 30-day free trial at HEY.com
Fizzy is a modern spin on kanban. Sign up for free at fizzy.do
Books by 37signals
Jason Fried on X
David Heinemeier Hansson on X

Showing off your product in real time, with real customers, changes everything. In this episode, Jason Fried and David Heinemeier Hansson walk through why 37signals has been hosting live demos and Q&A sessions since the Basecamp 5 launch, what makes the format work, and why being accessible and unafraid of your customers is underrated.
Key Takeaways
00:10 – How (and why) 37signals is embracing live sessions with customers
07:47 – Why showing beats telling when it comes to your own product
13:47 – Being open about what you don't know
16:16 – Showing work in progress without fear
17:42 – Learning to show off what you built with confidence
19:56 – People choose who they do business with
Links and Resources
Record a video question for the podcast
Watch The REWORK podcast on YouTube
Basecamp is the no-nonsense project management system. Sign up for free at Basecamp.com
HEY is a fresh take on email. Sign up for a 30-day free trial at HEY.com
Fizzy is a modern spin on kanban. Sign up for free at fizzy.do
Books by 37signals
Jason Fried on X
David Heinemeier Hansson on X

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
Jeff Bezos explains one-way door decisions and two-way door decisions
Record a video question for the podcast
Watch The REWORK podcast on YouTube
Basecamp is the no-nonsense project management system. Sign up for free at Basecamp.com
HEY is a fresh take on email. Sign up for a 30-day free trial at HEY.com
Fizzy is a modern spin on kanban. Sign up for free at fizzy.do
Books by 37signals
Jason Fried on X
David Heinemeier Hansson on X