Skip to content
Lenny's PodcastLenny's Podcast

Jason Fried challenges your thinking on fundraising, goals, growth, and more

Jason Fried is the co-founder and CEO of 37signals, the maker of Basecamp and HEY. 37signals is a very different kind of company. With fewer than 80 employees, they have over 100,000 customers, generate tens of millions of dollars in profit each year, and have no investors, board, or any plans to ever raise money or sell the company. In our conversation, we explore a path many tech founders never consider—bootstrapping. We discuss: • Why he and his team prioritize profit above all else • The unexpected challenges with raising venture capital • The “Shape Up” framework for building products • Why, and how, to foster a gut-driven culture • Jason’s thoughts on why work should not feel like war • Advice for starting a bootstrapped business • The philosophy behind Once, 37signals’s new line of software products — Brought to you by Coda—Meet the evolution of docs: https://coda.io/lenny | Sidebar—Accelerate your career by surrounding yourself with extraordinary peers: https://www.sidebar.com/lenny?utm_source=lennys&utm_medium=newsletter&utm_campaign=waitlist&utm_content=accelerate | Wix Studio—The web creation platform built for agencies: https://www.wix.com/studio?utm_source=Lennyspodcast&utm_medium=Podcastad&utm_campaign=SL Find the transcript and references at: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking Where to find Jason Fried: • X: https://twitter.com/jasonfried • LinkedIn: https://www.linkedin.com/in/jason-fried/ • Email: jason@hey.com Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Jason’s background (03:49) The success of 37signals (06:46) When raising money makes sense (09:58) The power of small teams (13:55) Defining success and goals (17:08) Playing “infinite games” in life (20:11) Starting a business vs. staying in business (22:13) Lessons from 25 years in business (27:28) Venture scale vs. bootstrapping (30:30) Choosing the right path for your business (33:19) The “Shape Up” framework (37:59) The drawback of promises (39:56) Adopting a new way of working (41:36) The two-week cooldown (43:53) Trusting intuition and gut (46:41) Creating a gut-driven culture (49:44) What Jason looks for in new hires (56:19) Advice on making changes and adapting (01:00:06) What Jason has changed his mind about (01:02:33) Planning in 6-week stretches and figuring it out as you go (01:06:43) Being proud of the work you do (01:09:05) Jason’s thoughts on why work should not feel like war (01:11:31) Advice for starting a bootstrapped business (01:14:33) You must be at peace with the worst that can happen (01:15:42) The benefits of bootstrapping (01:19:11) The value of constraints in business (01:22:00) Jason’s philosophy: “Just keep making great shit” (01:23:19) Once, 37signals’s new line of software products (01:26:33) The philosophy behind Once (01:35:47) Closing thoughts (01:37:23) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Jason FriedguestLenny Rachitskyhost
Dec 16, 20231h 49mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Jason Fried argues profits, constraints, and independence beat hyper-growth

  1. Jason Fried, co-founder and CEO of 37signals (Basecamp, HEY), explains why he believes most startups should avoid venture capital, stay small, and obsess over profitability rather than growth. He contrasts his 24-year, always-profitable, investor-free company with typical VC-backed software businesses that prioritize scale, headcount, and revenue over margins and sustainability.
  2. Fried details 37signals’ operating system: tiny two-person product teams, six‑week development cycles with built-in cooldowns, a strong reliance on gut and intuition, and a deliberate rejection of complex planning, OKRs, and long-term roadmaps. He frames entrepreneurship as an “infinite game” and a job he wants to keep doing, not a path to an exit.
  3. He also introduces Once, a new line of non‑SaaS business products you pay for once and host yourself, starting with a reboot of their early group chat product Campfire as a simpler, cheaper alternative to tools like Slack. Throughout, Fried argues that constraints, simplicity, and independence create better businesses, better products, and more enjoyable careers.

IDEAS WORTH REMEMBERING

5 ideas

Bootstrapping forces you to practice the core skill: making money.

When you don’t have investor cash, you must learn early how to charge, find customers, and keep margins healthy—skills many VC-backed founders delay and then struggle to develop once profit suddenly matters.

Most ideas are not venture-scale, and that’s a good thing.

Fried argues that chasing unicorn outcomes eliminates the vast middle ground of viable, lucrative businesses; far more founders can succeed by aiming for a solid, enduring company than by optimizing for the tiny odds of a billion‑dollar exit.

Small teams and tight constraints produce faster, better product work.

At 37signals, every feature is built by one designer and one programmer in at most six weeks, with a clear “appetite” instead of estimates. This prevents endless projects, reduces coordination overhead, and keeps morale high.

Avoid promises and long-term planning; decide close to the moment.

Promises like “by the end of the year” and multi‑year plans often lock companies into bad decisions and create stress; Fried prefers to revisit what to do every six weeks, letting current context and energy, not old commitments, drive priorities.

Gut and intuition are legitimate, underused tools in business decisions.

Fried insists that even so-called “data-driven” choices are ultimately judgment calls and deliberately asks his team how things feel, not just what metrics say, selecting hires partly on their taste and instinctive product sensibilities.

WORDS WORTH SAVING

5 quotes

The reason I think it's great for entrepreneurs to start bootstrapping is 'cause they just have more practice making money.

Jason Fried

Staying is harder than starting. I'm here to celebrate stay-ups.

Jason Fried

I don't plan long term because I want to do what I think, not what I thought.

Jason Fried

We don't have financial goals. If we make more than we spend, the things we did this year were worth it.

Jason Fried

Getting good at spending money is not as valuable a skill as getting good at making money.

Jason Fried

Bootstrapping vs. venture capital and what makes a venture-scale businessRunning a highly profitable, small team software company (37signals model)Shape Up: six-week cycles, two-person teams, appetites vs. estimatesGut, intuition, and judgment as core decision-making toolsRedefining success: infinite games, stay-ups, and work that doesn’t feel like warDesigning for constraints: simple products, single pricing, Fortune 5 Million focusOnce: pay-once, self-hosted software and re-launching Campfire

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome