Introduction

Welcome to the Zero to $10M ARR Podcast. I'm your host, Tom Morkes, along with my cohost Alex Turnbull, the founder and CEO of Groove and Helply. Today, we're joined by Jason Fried, co-founder and CEO of 37Signals.

Now, our guest today needs no introduction, but for the sake of consistency, i prepared one:

Jason cofounded 37signals in 1999. Originally a Chicago-based web design firm, the company pivoted to software in 2003 with their flagship product, Basecamp. By 2005, they dropped client work to focus entirely on software, creating tools like Campfire and Highrise. In the process, they developed Ruby on Rails, which became a global standard for web development. In 2014, they rebranded as Basecamp, doubling down on their flagship product, but in 2022, they returned to the 37signals name to expand beyond Basecamp with new products like Hey and WriteBook. Today, they remain a fully bootstrapped, remote-first company focused on building simple, effective software.

Beyond software, Jason is a prolific thinker and writer, and the co-author of several books, including “Getting Real”, “Remote”, and one of my personal favorites, the New York Times bestseller "Rework.”

In this episode, we’re diving deep into the world of bootstrapping—what it takes to build a profitable, sustainable company without venture capital. For over two decades, Jason has been one of the most outspoken advocates for bootstrapping, proving that a business can scale, thrive, and stay independent without outside funding. But bootstrapping isn’t just about avoiding VCs—it’s about control, optionality, playing infinite games, and operating with a different mindset from the typical high-growth, blitzscaling approach.

Jason, thank you so much for being here and welcome to the podcast!

This podcast is for founders who are trying to decide between raising money or bootstrapping. I'm hoping it helps them figure out the right path for them.

Questions

The Ultimate Bootstrap vs. VC Dilemma Questions for Jason Fried

Do I raise? Do I bootstrap? Succinct and in order.

1. To kick things off, from a philosophical perspective—why do you choose to bootstrap?
2. When you’re at $1M ARR and thinking, ‘Should I pour fuel on this or keep it lean?’—what questions should founders be asking themselves?
3. Is there a specific type of business or founder that shouldn't bootstrap? When does raising make more sense, if ever?
4. One of the most common fears founders have is: 'If I don’t raise, someone else will, and they’ll outspend me into the ground.' Have you ever actually felt that? And what would you say to someone feeling that pressure?
5. Everyone talks about ‘control’ as the big reason to bootstrap. But honestly... how much control do you really give up when you take VC? What's your honest take?
6. Optionality is your big thing. But doesn’t raising a round actually increase optionality sometimes? More capital = more moves you can make, right?
7. VC founders pitch this idea of building a generational company. Do you think bootstrapping limits the size and impact of what you can build?
8. You talk about playing long games. But how do you stay patient with slow, steady growth when the world is glorifying speed?
9. Do you think bootstrapping today is harder than when you did it? With how fast competitors move now, is it even realistic?
10. If you had raised money, how different do you think Basecamp would look today? Better? Worse?

Outro

That wraps up today’s episode of the Zero to $10M ARR Podcast. A huge thank you to Jason for sharing his insights on bootstrapping, business philosophy, and what it takes to build a sustainable company without outside funding.

If you enjoyed today’s conversation, be sure to subscribe, leave a review, and share it with other founders who need to hear this. To learn more about Jason and 37signals, visit 37signals.com.

Jason, thank you again for joining us.