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

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

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

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

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 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

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 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

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 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

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 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 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 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 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 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 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 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