for the love of play | Jason Fried

Today, we're joined by Jason Fried, the co-founder of 37signals, the company behind groundbreaking tools like Basecamp and HEY, and the co-author of influential books like Rework.

Jason is the quintessential authentic builder, someone who has spent over 25 years forging his own path, guided by a philosophy that often runs counter to the hustle culture of the tech world. In this episode, we explore the principles that have not only endured but have become the bedrock of his success. We delve into a unique form of minimalism—the idea that working less, constraining your ambitions, and focusing on what truly matters is not a limitation but a superpower. As Jason puts it, "small is not just a stepping stone, small is a great destination itself."

But this conversation goes beyond business. We journey into the realm of meditative depth, discussing the profound lessons learned from a silent retreat and the surprising power of simply letting things happen rather than forcing them. We touch on the essence of human connection—how trust, respect, and genuine appreciation are the invisible forces that build not just great products, but a sustainable and joyful life. This is a story about building with intention, leading with humanity, and finding clarity in the quiet spaces between the work.

[00:00] Alan Watts on the Division of Work and Play
[01:14] Introduction: The Authentic Builder, Jason Fried
[04:22] An Unlikely Inspiration: The Design of Annual Reports
[07:13] Learning Minimalism from Early BBS and ASCII Art
[12:45] The Making of a Mindset: Lessons from a Shoe Store
[18:34] The "Keepy Uppy" Philosophy of Business
[23:42] The First $20 from Germany: A Lesson in Appreciation
[27:37] The Selfishness of Creation: Building What You Love
[31:42] Reacting to Alan Watts: Business as a Way to Keep Playing
[36:01] Why Small is a Great Destination
[39:17] The Power of a 40-Hour Week and Letting Your Mind Wander
[43:30] Managing with a "Trust Battery"
[48:33] The Gentle Art of Saying No
[51:38] Reflections from a Silent Meditation Retreat
[58:17] Making It Happen vs. Letting It Happen
[59:22] Enduring Principles After 26 Years in Business