Learning from Mistakes is Overrated

REWORK

#Technology #Small Business #MBA #Business #Careers #Entrepreneur #37signals

6:24

Grumpy helps a reader choose the best hydrangea for their hometown. Plus, Grumpy’s gripe of the week. You can find us online at southernliving.com/askgrumpy Ask Grumpy Credits: Steve Bender aka The Grumpy Gardener - Host Nellah McGough - Co-Host Krissy Tiglias - GM, Southern Living Lottie Leymarie - Executive Producer Michael Onufrak - Audio Engineer/Producer Isaac Nunn - Recording Tech Learn more about your ad choices. Visit podcastchoices.com/adchoices…

4 years ago 28:29

MP3•Episode home

"Fail early and often." You hear this all the time in the tech start-up world. Failure has long been held up as a badge of honor for new start-ups. This week Jason and David take on this idea and make a pitch for learning from your successes instead of your mistakes.

Show Notes

06:22 - Backpack
06:29 - Highrise
10:39 - Adobe Creative Cloud
12:27 - Campfire
12:31 - Slack
16:28 - HEY for Domains
18:16 - Work at Basecamp
20:33 - Hire good writers (Getting Real)
20:38 - Hire managers of one (Signal v. Noise)
23:09 - Microsoft Project
27:04 - Remote: Office Not Required

324 episodes

Learning from Mistakes is Overrated

REWORK

469 subscribers

published 4 years ago

MP3•Episode home

Show Notes

06:22 - Backpack
06:29 - Highrise
10:39 - Adobe Creative Cloud
12:27 - Campfire
12:31 - Slack
16:28 - HEY for Domains
18:16 - Work at Basecamp
20:33 - Hire good writers (Getting Real)
20:38 - Hire managers of one (Signal v. Noise)
23:09 - Microsoft Project
27:04 - Remote: Office Not Required

324 episodes

#Technology #Small Business #MBA #Business #Careers #Entrepreneur #37signals

All episodes

1
Rapid Fire Questions with Jason and David 21:18

6 days ago21:18

21:18

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 Books by 37signals HEY World | HEY REWORK podcast merch The REWORK podcast The Rework Podcast on YouTube The 37signals Dev Blog 37signals on YouTube @37signals on X…

1
Eat your own dog food 21:14

27 days ago21:14

21:14

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 Get Basecamp for free at Basecamp.com Books by 37signals HEY World | HEY REWORK podcast merch The REWORK podcast The Rework Podcast on YouTube The 37signals Dev Blog 37signals on YouTube @37signals on X…

1
Picking Priorities 11:50

5 weeks ago11:50

11:50

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 Get Basecamp for free at Basecamp.com Books by 37signals HEY World | HEY REWORK podcast merch The REWORK podcast The Rework Podcast on YouTube The 37signals Dev Blog 37signals on YouTube @37signals on X…

1
Building On the Side 19:57

6 weeks ago19:57

19:57

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 Books by 37signals HEY World | HEY REWORK podcast merch The REWORK podcast The Rework Podcast on YouTube The 37signals Dev Blog 37signals on YouTube @37signals on X…

1
Why we choose profit 21:10

7 weeks ago21:10

21:10

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 Get Basecamp for free 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…

1
Build a business that runs without you 29:05

8 weeks ago29:05

29:05

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 Books by 37signals HEY World | HEY The REWORK podcast The Rework Podcast on YouTube The 37signals Dev Blog 37signals on YouTube @37signals on X…

1
Increasing Capacity 26:46

9 weeks ago26:46

26:46

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! Find out about future job openings at 37signals Get Basecamp for free 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…

1
Roles at the company, staying involved as a founder & other listener questions 33:11

10 weeks ago33:11

33:11

Jason Fried and David Heinemeier Hansson answer listener questions in this episode of The REWORK Podcast . They discuss the roles 37signals hires for (and the ones they don’t), the importance of staying accessible as a founder, and the thought process behind choosing a business structure. Key Takeaways 00:16 – Employee roles at 37signals 04:33 – How non-programmers contribute to programming 16:44 – Techniques for writing job descriptions 18:47 – Tips for being an accessible founder 25:22 – Deciding on a business structure Links and Resources: We're hiring a Product Designer! Find out about future job openings at 37signals Get Basecamp for free 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…

1
Bringing Back Free 21:28

11 weeks ago21:28

21:28

37signals' co-founders Jason Fried and David Heinemeier Hansson are back to talk about the ins and outs of offering a product for free. In this episode of The REWORK Podcast , they break down why they decided to reintroduce a free Basecamp plan, how offering free access can actually drive sales, and balancing analytics with instincts. Key Takeaways: 00:45 – The original philosophy behind Basecamp’s free plan 03:14 – Going beyond the free trial 07:36 – Tracking analytics without getting lost in the numbers 12:48 – The true cost of offering something for free 19:13 – Pricing strategies for new products 37signals is building Links and Resources: Get Basecamp for free 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…

1
Managing vs. Mentoring 24:30

14 weeks ago24:30

24:30

There are no full-time managers at 37signals, but that doesn't mean the company is void of mentorship. In this episode of The REWORK Podcast , host Kimberly Rhodes chats with Principal Programmer Jeffrey Hardy as he breaks down the company’s focus on peer-to-peer mentorship. They discuss hiring practices that allow for less management and what mentorship looks like amongst the team. Key Takeaways: 00:42 – Meet Jeffrey Hardy, Principal Programmer 02:09 – The evolution of 37signals' management structure 05:19 – Replacing managers with mentors 10:53 – How hiring impacts the ability to operate without managers 13:35 – The power of seeking entrepreneurial experience 15:10 – A day in the life of a mentor 17:40 – Tips for being a better mentor Links and Resources: Books by 37signals 30-day free trial of HEY 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…

1
Blogging Isn't Dead 14:55

15 weeks ago14:55

14:55

Does blogging still matter in tech? In this episode of The REWORK Podcast , host Kimberly Rhodes chats with 37signals' Principal Programmer Jorge Manrubia about why blogging is very much alive. They dig into the history of the 37signals developers blog, the company's process for contributions, and the added benefits this communication tool provides. Key Takeaways: 00:50 – Meet Jorge 01:03 – The history of the 37signals developers blog 02:25 – The process — who contributes and how topics are decided 05:09 – Benefits of writing on the blog and sharing content with the public 07:40 – What to consider when starting a company blog 09:43 – Sharing code isn’t as revealing as you might think 11:28 – Secondary benefits of sharing your content 13:30 – What’s next for the blog? Links and Resources: The 37signals Dev Blog Books by 37signals 30-day free trial of HEY 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…

1
Building a Community 18:58

16 weeks ago18:58

18:58

There is a way to bring your customers together in a meaningful way. In this episode of The REWORK Podcast , host Kimberly Rhodes welcomes 37signals' Support Team members Merissa Dawson and Ashley Bowe to discuss how the Basecamp Community came to life. They describe how they've connected with Basecamp customers and how they've connected customers with each other. They also offer a few tips for anyone looking to start their own community of customers and company enthusiasts. Key Takeaways: 00:40 – Meet Merissa and Ashley from Basecamp Support 01:54 – The Basecamp Community origin story 05:03 – The Community as a place for sharing and collaboration 07:20 – The 37signals team role within the Community 09:08 – Starting a community without fear of failure 13:27 – Tips for starting your own community of users and fans Links and Resources: Join the Basecamp Community " Launch: 37signals Answers" from Signal v. Noise How Decent Espresso uses multiple tools in a single Basecamp project Books by 37signals 30-day free trial of HEY 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…

1
Support is a Feature 20:43

17 weeks ago20:43

20:43

Customer support is more than just a department — it’s a core feature of any great product. In this episode of The REWORK Podcast , Kimberly Rhodes chats with Chase Clemons, Head of Customer Support at 37signals, about the company's view of support as a product feature. They discuss 37signals' approach to helping customers, the value of ongoing training, and how AI can fit into support strategy without sacrificing the personal connection. Key Takeaways: 00:37 – Chase Clemons, Head of Support at 37signals 02:12 – Customer Support is a feature, not a cost center. 04:09 – Support should focus on the customer experience 06:36 – Using case studies to train your support team 07:49 – Team members are trusted to use good judgment 09:58 – Maintaining a friendly, conversational tone with customers 11:27 – Measuring success in Customer Support 14:12 – AI vs. the human element in Support 17:25 – Encourage customers to reach out Links and Resources: Books by 37signals 30-day free trial of HEY 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…

1
Hire When It Hurts 19:51

18 weeks ago19:51

19:51

Wondering when it’s the right time to grow your team? In this episode of The REWORK Podcast , 37signals' co-founders Jason Fried and David Heinemeier Hansson chat about their “hire when it hurts” approach as described in their book REWORK . They cover why you shouldn’t rush into bringing someone on board, how to know when there's a critical business need, and how to seize the moment when the right people show up. Key Takeaways: 00:38 – Try tackling projects with the team you already have before hiring 02:43 – Some roles don’t call for a full-time position 07:33 – Knowing the difference between an actual staffing shortage vs. just being busy 09:48 – A workload spike doesn’t always mean it’s time to expand 12:33 – Snagging available talent early if you’re already planning to hire soon 15:35 – One open position can become multiple hires when the talent pool is just right Links and Resources: Books by 37signals 30-day free trial of HEY 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…

1
Seven Shipping Principles 22:54

19 weeks ago22:54