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