Balancing Familiarity and Change in Upgrades

In software development, there are updates, and then there are complete overhauls. This week, Jason Fried joins Kimberly Rhodes to talk about how the team decides when it’s time to rebuild from the ground up. They dig into the transition between versions, how customer feedback fits in, and even drop a few hints about what’s coming in Basecamp 5.

Key Takeaways

• 00:10 – A walk through of Basecamp's evolution
• 03:00 – How to recognize when it’s time for a new version
• 05:52 – Pricing considerations
• 11:42 – There’s no perfect moment to ship a new version
• 13:16 – How and when to evaluate customer feedback
• 18:58 – A sneak peek at Basecamp 5 features

Links and Resources

• Record a video question for the podcast
• Books by 37signals
• Sign up for a 30-day free trial at Basecamp.com
• HEY World | HEY
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X