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