- 26 minutes 51 secondsCompeting with giants, the end of SaaS & other listener questions
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
19 August 2026, 8:00 am - 19 minutes 30 secondsRapid Fire Q&A with Jason Fried and David Heinemeier Hansson
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
12 August 2026, 8:00 am - 26 minutes 3 secondsWe'll do it live
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
5 August 2026, 8:00 am - 25 minutes 38 secondsWhat's the worst that could happen?
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
29 July 2026, 8:00 am - 15 minutes 3 secondsStart Here: Building a better onboarding experience
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
22 July 2026, 8:00 am - 22 minutes 17 secondsDon't write it down
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
15 July 2026, 8:00 am - 32 minutes 3 secondsAI Challenges in Software Development
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
1 July 2026, 8:00 am - 31 minutes 22 secondsLaunch Details and Decisions
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
24 June 2026, 8:00 am - 28 minutes 43 secondsClearing the decks for launch
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
13 May 2026, 8:00 am - 25 minutes 38 secondsEasy to leave
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
8 April 2026, 8:00 am - 26 minutes 39 secondsPencils down
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
1 April 2026, 8:00 am - More Episodes? Get the App