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 | Sidebar—Accelerate your career by surrounding yourself with extraordinary peers | Wix Studio—The web creation platform built for agencies—Find the full transcript 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 cultu