REWORK

Latest Episodes:

One-way Doors Aug 26, 2026

Show notes

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

Competing with giants, the end of SaaS & other listener questions Aug 19, 2026

Show notes

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

Rapid Fire Q&A with Jason Fried and David Heinemeier Hansson Aug 12, 2026

Show notes

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

We'll do it live Aug 05, 2026

Show notes

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

What's the worst that could happen? Jul 29, 2026

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

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

Start Here: Building a better onboarding experience Jul 22, 2026

Show notes

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

Don't write it down Jul 15, 2026

Show notes

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 Challenges in Software Development Jul 01, 2026

Show notes

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

Launch Details and Decisions Jun 24, 2026

Show notes

Basecamp 5 is out in the world! In this episode, Jason Fried and David Heinemeier Hansson sit down with host Kimberly Rhodes to talk about some of the details of the launch and the big decisions that went into it. They discuss what went smoothly, what only a live rollout could reveal, and the response from current customers.

Key Takeaways

00:34 – How this launch compared to previous Basecamp versions
03:50 – Setting (and moving) the launch date
06:45 – How the mobile apps equaled a point of no return
13:07 – Going live is when things get real
16:31 – The decision to move all customers to Basecamp 5 at once
19:52 – Handling the customers who push back hardest
21:11 – How a great support team makes or breaks a major product transition

Links and Resources

See where Basecamp is being used right now – basecamp.com/live
If Your Product Is Great, It Doesn't Need to Be Good by Paul Buchheit
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

Clearing the decks for launch May 13, 2026

Show notes

With the launch of Basecamp 5 approaching, 37signals co-founders Jason Fried and David Heinemeier Hansson discuss what happens inside their company when it enters “launch mode.” They talk about temporarily shifting priorities, the difference between routine operations and launch periods, and why putting lower-priority tasks on hold is often necessary to make meaningful progress. Plus, Jason and David share their favorite aspects of the newest version of Basecamp.

Key Takeaways

00:00 – Introduction
00:10 – Pausing processes and the power of “not now”
03:41 – Moving quickly and deciding to just build it
08:38 – Pressing pause on routines to stay focused on the goal
11:20 – Staying flexible while working through the chaos
13:54 – What life after launch will look like
20:54 – Jason and David share their favorite Basecamp 5 updates

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

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