Jason Fried

Co-Founder and CEO at 37signals

Co-founder and CEO of 37signals which makes Basecamp and HEY, running a radically different kind of company with no investors, no board, no plans to go public, 75 employees, 100,000+ customers, 24 consecutive years of profit, and double-digit million dollar annual profits — all while competitors have thousands of employees.

The Visionary The Operator

Dimension Profile

Strategic Vision 80%

Execution & Craft 85%

Data & Experimentation 25%

Growth & Distribution 45%

Team & Leadership 60%

User Empathy & Research 50%

Key Themes

bootstrapping versus venture-backed growth radical efficiency with small teams two-person teams with six-week maximum cycles one-price simplicity model constraints as competitive advantage contrarian approach to company building

Episode Summary

Jason Fried makes the contrarian case for bootstrapping and radical efficiency, revealing how 37signals competes with companies 20-40x their size by building every feature with just two people in six-week maximum cycles, charging one simple price, and focusing on profit rather than growth. He argues that Silicon Valley has turned the most naturally profitable business model (software with 80-90% margins) into the least profitable by overspending on people and customer acquisition, and that constraints and simplicity are competitive advantages, not limitations.

Leadership Principles

→ Bootstrapping teaches you the fundamental skill of making money — venture-backed founders defer this skill and most never learn it
→ Every feature is built by two people, one programmer and one designer, with a maximum of six weeks — we don't get stuck in huge projects with 18-person meetings
→ Silicon Valley has found a way to make the most profitable style of business the least profitable — software margins should be 80-90% but most companies barely break even

Notable Quotes

"Silicon Valley has found a way to make the most profitable style of business the least profitable. Software margins should be close to 80 or 90%. Most businesses in the world would love to have Silicon Valley style economics."
— On how the tech industry squanders naturally high software margins

"Every feature we work on is two people, one programmer, one designer, and they have a maximum of six weeks. We don't get stuck in big huge projects with meetings with 18 people and slow decision-making."
— On 37signals' approach to product development

"If you gave me 1,000 people, I wouldn't know what to do with them. We would fall apart. We would be a worse off company with 500 people."
— On why small teams are a feature not a limitation

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