This week on The REWORK Podcast, host Kimberly Rhodes is joined by Jason Fried to talk about cover letters — what they say about a candidate, how they’re reviewed at 37signals, and why they still matter. Jason shares his take on the value of genuine effort, how AI can either help or hurt your chances, and why hiring should stay a human process.

Key Takeaways:

 * 00:13 – A cover letter says more about you than your résumé ever could
 * 03:35 – How using AI the right (or wrong) way shows up in applications
 * 06:04 – Why a pre-screening team reads every cover letter first
 * 07:18 – A thoughtful effort is often what gets you to the short list
 * 13:36 – It’s easier than you think to spot procrastination
 * 16:50 – At 37signals, hiring decisions are made by people—not algorithms

Links and Resources:

 * “Cover Letters? Yes!” From Jason Fried’s HEY World [https://world.hey.com/jason/cover-letters-yes-25dcdd0c]
 * “When You Review Hundreds of Cover Letters…” LinkedIn post by Jason Fried [https://www.linkedin.com/posts/jason-fried_when-you-review-hundreds-of-cover-letters-activity-7330716611688980484-3HWn/?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAFOmhoBb_q4GXRGpaSenRCr6g4eeY_HxpU]
 * Record or upload a video question for Jason and David [https://sendspark.com/request/The-REWORK-Podcast/hsj7miu9gesm8gq6jm8pr6z9izly0fc2]
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * REWORK podcast merch [https://37signals.com/podcast/shop]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

The case for cover lettters

In this episode of The REWORK Podcast, 37signals co-founders Jason Fried and David Heinemeier Hansson answer listener questions. They explain why keeping tabs on competitors isn’t part of their strategy, reflect on the changing face of leadership as younger CEOs step in, and talk about the energy that comes with fresh perspectives.

Key Takeaways:

 * 00:22 – Why focusing on your customers matters more than watching competitors
 * 05:55 – A new wave of CEOs is bringing a fresh approach to leadership
 * 10:34 – Why you don’t always need a mentor—sometimes figuring it out is the best teacher
 * 17:38 – Jason and David’s different views on handling employee roadblocks

Links and Resources:

 * Record or upload a video question for Jason and David [https://sendspark.com/request/The-REWORK-Podcast/hsj7miu9gesm8gq6jm8pr6z9izly0fc2]
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * REWORK podcast merch [https://37signals.com/podcast/shop]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Ignoring the competition, the next wave of CEOs & other listener questions

How much data do you really need to make good decisions? In this episode of The REWORK Podcast, Jason Fried and David Heinemeier Hansson talk about 37signals’ evolving relationship with analytics—from working with a full-time analyst to now focusing only on the numbers that truly matter. They share why gut feeling, curiosity, and margin often outweigh dashboards and reports—and how trimming the data obsession can lead to better, bolder decisions.

Key Takeaways:

 * 00:09 – The shift from having a full-time data analyst to working without one
 * 02:25 – Just because you can’t measure it doesn’t mean it’s not important
 * 07:59 – Analytics don’t always drive product decisions
 * 10:15 – How financial margin fuels freedom to experiment
 * 13:42 – Don’t let data make you overly cautious
 * 15:26 – David’s take on cutting unnecessary costs
 * 19:48 – Weighing cost vs. value when making decisions

Links and Resources:

 * Record or upload a video question for Jason and David [https://sendspark.com/request/The-REWORK-Podcast/hsj7miu9gesm8gq6jm8pr6z9izly0fc2]
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * REWORK podcast merch [https://37signals.com/podcast/shop]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

By the Numbers

In this episode of The REWORK Podcast, host Kimberly Rhodes puts 37signals co-founders Jason Fried and David Heinemeier Hansson in the hot seat with a round of rapid-fire questions — from favorite apps and founder skills to customer requests and what's coming next.

Key Takeaways:

 * 00:11 – Favorite software that Jason and David use (that they haven't built)
 * 03:42 – Underrated skills every founder should develop
 * 06:26 – Times they’ve completely changed their minds on a decision
 * 14:05 – Customer feature requests that likely won’t ever happen
 * 15:36 – A new 37signals product is on the way

Links and Resources:

 * Screen Studio – https://screen.studio/
 * Obsidian – https://obsidian.md/
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * REWORK podcast merch [https://37signals.com/podcast/shop]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Rapid Fire Questions with Jason and David

Before anything ships at 37signals, the team puts it to the test—by using it themselves. In this episode of The REWORK Podcast, co-founders Jason Fried and David Heinemeier Hansson talk about the importance of dogfooding, or using your own product before handing it off to customers. They share how this practice keeps them close to the real problems, and sometimes even kills off ideas that just don’t hold up.

Key Takeaways:

 * 00:27 – Why every 37signals product is used internally before it ships
 * 07:15 – Who makes the final call after internal feedback comes in
 * 12:44 – The importance of building things you’ll actually use
 * 16:48 – Some products and features don’t make it past internal testing

Links and Resources:

 * “Doing what you think, not what you thought” from Jason Fried’s HEY World [https://world.hey.com/jason/doing-what-you-think-not-what-you-thought-60bb5bef]
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * REWORK podcast merch [https://37signals.com/podcast/shop]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Eat your own dog food

How do you decide what to work on next, without relying on a long, stale to-do list? In this episode of The REWORK Podcast, 37signals co-founders Jason Fried and David Heinemeier Hansson talk about why they don’t rely on lengthy roadmaps to set priorities. Instead, they focus on what makes sense now, not what seemed like a good idea months ago. They explain how working in real time leads to better decisions and thinking that fits the moment.

Key Takeaways:

 * 00:44 – Priorities aren’t permanent—they’re meant to shift as you learn
 * 03:20 – Ditch the roadmap mentality in favor of real-time decision-making
 * 07:20 – There’s a difference between winging it and planning as you go
 * 09:10 – Why 6-week cycles give you just enough structure without locking you in

Links and Resources:

 * “Doing what you think, not what you thought” from Jason Fried’s HEY World [https://world.hey.com/jason/doing-what-you-think-not-what-you-thought-60bb5bef]
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * REWORK podcast merch [https://37signals.com/podcast/shop]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Picking Priorities

Have a day job but dreaming of launching the next big thing? In this episode of The REWORK Podcast, a listener question sparks a conversation with 37signals co-founders Jason Fried and David Heinemeier Hansson about juggling consulting work while building products on the side. They share real talk about timing, expectations, motivation — and why your side project should serve you, even if it doesn’t turn into a smash hit.

Key Takeaways:

 * 00:12 – Host Kimberly Rhodes reads a listener question about balancing consulting with product building
 * 01:01 – Why it’s easier than ever to build something—but harder than ever to get noticed
 * 05:48 – The barrier to entry is low, but staying in the game is the hard part
 * 08:05 – There’s no formula for what will take off and what won’t
 * 13:08 – Aim for more than just small wins—set bold goals
 * 16:04 – You have to be fully invested if you want your idea to stand a chance

Links and Resources:

 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * REWORK podcast merch [https://37signals.com/podcast/shop]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Building On the Side

In a world where constant reinvestment is celebrated, 37signals chooses profit. In this episode of The REWORK Podcast, co-founders Jason Fried and David Heinemeier Hansson talk about how profit gives them freedom, clarity, and staying power—not just for the company, but for their customers too. They make the case for building a business that’s solid, simple, and self-funded.

Key Takeaways:

 * 00:27 – How being profitable is actually a choice
 * 08:34 – Why it’s important to take money off the table
 * 11:35 – Striking the right balance between ego and humility
 * 15:00 – Profitability isn’t guaranteed forever
 * 18:27 – Well-managed profits create reliability for customers

Links and Resources:

 * Why We Choose Profit [https://37signals.com/why-we-choose-profit/]
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Why we choose profit

Can you build a company that thrives even when you’re not in the room? In this episode of The REWORK Podcast, 37signals co-founders Jason Fried and David Heinemeier Hansson talk about the jobs they've created for themselves and how they're able to step away without progress coming to a halt. They discuss the fine line between being involved and letting the team run things without them.

Key Takeaways:

 * 00:14 – The importance of creating a job for yourself that you enjoy
 * 02:45 – The tragedy of owning a business you don't love
 * 06:56 – Staying relevant in your business and knowing when to step in
 * 15:14 – Knowing when to step back so your team can grow
 * 17:51 – Maintaining a life outside of your business and having work/life balance
 * 20:36 – The parts of the business that require the founders' involvement
 * 23:33 – Jason and David's stance of not being serial entrepreneurs

Links and Resources:

 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Build a Business That Runs Without You

How do you do more without growing your team substantially? In this episode of The REWORK Podcast, 37signals co-founders Jason Fried and David Heinemeier Hansson share how they’re expanding their product lineup while keeping their team lean. They reflect on how their approach to building software has evolved, and how pushing into the unknown makes the work more exciting. 

Key Takeaways

 * 00:28 – How 37signals’ product lineup has evolved over time
 * 08:00 – Why the company is adding a product designer to the team
 * 15:07 – Finding the “fun” in creating new products
 * 18:50 – Challenging yourself by stepping into the unknown
 * 23:16 – Using real products as a way to do research and development

Links and Resources:

 * We're hiring a Product Designer! [https://apply.workable.com/37signals/j/FC3DECDFE2/]
 * Find out about future job openings at 37signals [https://37signals.com/jobs]
 * Get Basecamp for free at Basecamp.com [https://basecamp.com/pricing]
 * Books by 37signals [https://37signals.com/books]
 * HEY World | HEY [https://www.hey.com/world/]
 * The REWORK podcast [https://www.rework.fm/]
 * The Rework Podcast on YouTube [https://www.youtube.com/@37signals/podcasts]
 * The 37signals Dev Blog [https://dev.37signals.com/]
 * 37signals on YouTube [https://www.youtube.com/c/basecamp/featured]
 * @37signals on X [https://twitter.com/37signals]

Increasing Capacity

A podcast by 37signals about the better way to work and run your business. In Season 2, we're going through Rework (the book) chapter by chapter and talking with authors, Jason Fried and David Heinemeier Hansson, about what's changed in the world of business over the last eleven years since the book was published.

Shaun

Shows