Insight
Sep 7, 2025
Jason Fried: $0 to $280M ARR (with no venture capital)
Alex Turnbull
Introduction
When it comes to building a SaaS business, the biggest early question most founders face is this: do I raise money or do I bootstrap?
On this episode of the Zero to $10M ARR Podcast, we sat down with someone who’s been answering that question for over two decades—Jason Fried, co-founder and CEO of 37signals.
Jason’s story is legendary in tech circles. He launched 37signals back in 1999 as a web design firm. By 2003, the team shifted to software with the launch of Basecamp, and by 2005, they dropped client work entirely to double down on product. Along the way, they built Ruby on Rails, open-sourced it, and helped shape how modern web apps are built today.
Since then, Jason and his team have shipped multiple products, including Campfire, Highrise, Hey, and WriteBook—all while staying fully bootstrapped and remote.
He’s also the author of several best-selling books like Rework and Remote, which have inspired millions of founders to build differently.
In this episode, we dig into:
Why Jason has always chosen to bootstrap
What tradeoffs founders should consider at $1M ARR
The fear of being outspent by VC-backed competitors
Whether raising capital actually gives you more optionality
If bootstrapping today is harder than it was 20 years ago
How Basecamp might look today if they had raised
This episode is especially relevant if you’re sitting on a promising product and asking yourself: Do I keep it lean, or do I raise and scale faster?
Jason doesn’t preach. He shares real, lived experience—clear, honest, and direct. If you’ve ever wondered what it’s really like to grow a product without outside capital, this is the conversation you need to hear.
Listen now and decide for yourself which path makes sense for the company you’re trying to build.
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