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

Getting a new customer through the door is one thing, but making sure they understand how things work is another. In this episode, Jason Fried and David Heinemeier Hansson break down how (and why) 37signals redesigned the onboarding experience with their latest version of Basecamp, why onboarding is one of the easiest things to overlook, and what it looks like when founders stay personally connected to that first impression.

Key Takeaways

• 00:09 – What Basecamp's onboarding looked like before, and what changed with Basecamp 5
• 04:01 – Why onboarding is one of the hardest things to get right
• 08:33 – Why the people who built it are best suited to showcase it to customers
• 11:07 – Using onboarding to introduce who you are, not just what you built

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

Customer feedback is valuable, but not all of it deserves a spot on your to-do list. In this episode, Jason Fried and David Heinemeier Hansson revisit a chapter from their book REWORK, sharing how 37signals filters feedback, why roadmaps can do more harm than good, and what happens when companies let fear drive their product decisions.

Key Takeaways

• 00:40 – Why writing down every customer request can work against you
• 03:08 – Handling feedback on the technical and open source side
• 07:37 – Why 37signals doesn't really use time specific roadmaps
• 09:54 – How vague promises set customers up for disappointment
• 13:33 – Avoiding promised feature regret
• 16:10 – Don't let the fear of losing customers steer your decisions
• 19:29 – Resisting the pressure to just "do something”

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

AI didn't just speed up the development of Basecamp 5, it changed how it was built. This week, Jason Fried and David Heinemeier Hansson break down how much of a role AI played in building their latest product, where it shines, and how 37signals had to adjust its process to keep their code base clean.

Key Takeaways

• 00:11 – How much of a role AI played in building Basecamp 5
• 09:55 – Where the intelligence technology truly excels
• 14:42 – The new challenge of saying no when features become easier to build
• 16:19 – Why a leaner product roadmap still matters
• 18:32 – Staying "easy to use" while competitors focus on AI features
• 20:44 – Why AI deserves both the hype and the skepticism
• 25:12 – Token spend, productivity, and staying profitable

Links and Resources

• AI Agents welcome in Basecamp
• 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