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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.fizzy.do/
• Books by 37signals
• Jason Fried on X
• David Heinemeier Hansson on X

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 – https://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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.fizzy.do/
• Books by 37signals
• Jason Fried on X
• David Heinemeier Hansson on X

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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.fizzy.do/
• Books by 37signals
• Jason Fried on X
• David Heinemeier Hansson on X

Making it easy for customers to leave might sound like the wrong move, but it's actually a sign of confidence. This week, Jason Fried and David Heinemeier Hansson talk about why removing friction, especially on the way out, builds more trust. They get into cancellation flows, keeping customers by choice instead of pressure, and why people are more likely to share their positive experience when you don't make it hard to go.

Key Takeaways

• 00:11 – Leaving should be just as easy as signing up
• 03:23 – Offering a pause instead of forcing a full cancellation
• 11:00 – Simplifying the buying experience from the start
• 14:07 – How transparency builds long-term loyalty
• 17:05 – Creating experiences that make people want to come back

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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.fizzy.do/
• Books by 37signals
• Jason Fried on X
• David Heinemeier Hansson on X

Knowing when to stop is harder than it sounds. In this episode, Jason Fried and David Heinemeier Hansson talk about the moment when more work stops helping and starts getting in the way. They share how to recognize when something is done, why chasing perfection can do more harm than good, and how putting the pencil down at the right time leads to better results.

Key Takeaways

• 00:11 – The "pencils down" phase of product development
• 01:24 — Testing by the entire company
• 03:17 — AI Workflow & vibe coding
• 09:58 — Speed vs durability
• 15:08 — Refinement & cutting features
• 18:08 — Full launch strategy
• 20:00 — “Give It Five Minutes” Mindset

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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.fizzy.do/
• Books by 37signals
• Jason Fried on X
• David Heinemeier Hansson on X

Opening things up changes how people use your product. In this episode, David Heinemeier Hansson walks through a new feature that makes Basecamp accessible to AI agents through a Command Line Interface (CLI). He shares how this update can lead to entirely new ways of working for those that are technically minded.

Key Takeaways

• 00:10 – Redefining product accessibility
• 03:27 – Opening the door to AI agents
• 10:07 – Starting small and seeing where it leads
• 13:37 – The future for agent accessibility with other 37signals products

Links and Resources

• Bring your own AI agents to Basecamp — https://basecamp.com/agents
• 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 https://www.hey.com/
• Fizzy is a modern spin on kanban. Sign up for free at https://www.fizzy.do/
• Books by 37signals
• Jason Fried on X
• David Heinemeier Hansson on X

Profit matters, but it’s not the whole story. In this episode, Jason Fried and David Heinemeier Hansson talk about building a company around independence instead of endless growth. They reflect on finding the right size for a business, keeping costs low to preserve freedom, and choosing a long, sustainable run over chasing scale at any cost.

Key Takeaways

• 00:10 – Finding your “orbit” when you don’t need to keep pushing for more
• 03:39 – Letting go of the idea that growth has to be endless
• 09:05 – Choosing independence instead of outside pressure
• 17:48 – Keeping costs low so you have room to try things your way
• 19:57 – Why steady can beat getting bigger

Links and Resources

• Fizzy is a modern spin on kanban. Try it for free at https://www.fizzy.do/
• Record a video question for the podcast
• Sign up for a 30-day free trial at Basecamp.com
• Books by 37signals
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X

Not every decision comes from a spreadsheet. In this episode, Jason Fried and David Heinemeier Hansson talk about trusting your instincts when building something new. They share how experience sharpens those instincts over time, and how real products produce the feedback that actually moves things forward.

Key Takeaways

• 00:11 – Letting your gut guide decisions
• 03:54 – Strengthening instincts through real choices
• 05:08 – Sometimes the best move is simply to build it
• 07:49 – Breaking free from analysis paralysis
• 15:02 – Real products bring real feedback
• 17:11 – Learning to trust your own judgment
• 18:26 – Welcoming feedback instead of fearing it

Links and Resources

• Fizzy is a modern spin on kanban. Try it for free at https://www.fizzy.do/
• Record a video question for the podcast
• Sign up for a 30-day free trial at Basecamp.com
• Books by 37signals
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X

Following up on an earlier conversation about AI, this episode shifts to the product side of the discussion. Host Kimberly Rhodes chats with 37signals CEO and co-founder Jason Fried about his daily AI use, what it's helped him do more efficiently, customer expectations, and how he's thinking about AI's role in future product updates.

Key Takeaways

• 00:12 – Putting AI tools to work
• 06:42 – Using AI to reclaim time, not replace thinking
• 12:19 – Where 37signals sees thoughtful implementation fitting in
• 17:16 – Why rushing adoption can backfire
• 18:25 – The ongoing debate from the customer perspective
• 21:45 – Why workforce changes aren’t always tied to automation
• 25:40 – Human interaction still matters

Links and Resources

• The owner's word weighs a ton by Jason Fried on Signal v. Noise
• Fizzy is a modern spin on kanban. Try it for free at https://www.fizzy.do/
• Record a video question for the podcast
• Sign up for a 30-day free trial at Basecamp.com
• Books by 37signals
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X

Connecting with customers is part of the job. In this episode, Jason Fried and David Heinemeier Hansson share why staying close to the people who use your product still matters, even as companies scale. They touch on writing customers directly, keeping the door open after the first reply, and why real conversations beat shouting into the social media void.

Key Takeaways

• 00:11 – Writing customers from a real inbox
• 05:21 – Building real relationships with the people who use your product
• 11:34 – Keeping the line open after the first exchange
• 14:07 – Why email still feels more personal than sliding into DMs
• 19:29 – Getting to know who your customers actually are
• 21:55 – Why real human connection is still the point

Links and Resources

• Fizzy is a modern spin on kanban. Try it for free at https://www.fizzy.do/
• Record a video question for the podcast
• Sign up for a 30-day free trial at Basecamp.com
• Books by 37signals
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X

Sometimes speed matters more than polish. In this episode, the team shares how a HEY Calendar feature went from idea to shipped in about a day — and what made that possible. It’s a look at when moving quickly helps, when it doesn’t, and how writing clean code gives you room to change your mind later without breaking everything.

Key Takeaways

• 00:11 – Shipping a new feature in roughly a day
• 03:14 – Catching the moment while it's hot
• 08:02 – Shortening the path from idea to implementation
• 12:04 – Making change easier with clean, thoughtful code
• 19:42 – Designing things that hold up and are easy to fix
• 22:51 – Building for the future

Links and Resources

• "Building HEY Calendar's Year View" from Michelle Harjani's HEY World
• Maintenance of Everything (Part One) by Stewart Brand
• Fizzy is a modern spin on kanban. Try it for free at https://www.fizzy.do/
• Record a video question for the podcast
• Sign up for a 30-day free trial at Basecamp.com
• Books by 37signals
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X

The confetti’s settled. The product is out in the world. So… what happens next? Jason Fried and David Heinemeier Hansson share what the days after a launch actually look like at 37signals. They discuss not letting early numbers steer the ship, making space for rest after the push, and remembering that shipping is just the start, not the finish line.

Key Takeaways

• 00:10 – What happens shortly after launch
• 02:09 – Dialing the team back
• 05:10 – Product touch ups and enhancements
• 06:16 – Returning to a familiar work rhythm
• 07:16 – Balancing the product push with real breaks
• 10:39 – Not letting early signups call the shots
• 20:32 – Sticking with what works for your team
• 22:00 – Putting the product ahead of quick money moves
• 27:26 – Why launch buzz doesn’t last forever

Links and Resources

• The Great Falls of Boeing, Intel, and Apple from David Heinemeier Hansson's HEY World
• Fizzy is a modern spin on kanban. Try it for free at https://www.fizzy.do/
• Record a video question for the podcast
• Sign up for a 30-day free trial at Basecamp.com
• Books by 37signals
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X

A fresh batch of listener questions leads this week's conversation. Jason Fried and David Heinemeier Hansson talk through how they approach product walkthroughs, what's ahead for open code at 37signals, and why a little fun still belongs in serious software.

Key Takeaways

• 00:22 – Recording product walkthroughs without scripts or polish
• 11:45 – Writebook as an open source product
• 15:04 – How the 37signals team uses Basecamp and Fizzy together
• 22:52 – The quiet joy of Easter eggs and playful details in software

Links and Resources

• Fizzy is a modern spin on kanban. Try it for free at https://www.fizzy.do/
• Record a video question for the podcast
• Sign up for a 30-day free trial at Basecamp.com
• Books by 37signals
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X