In this deeply personal and unflinchingly honest episode, Kevin sits down with his friend of over two decades, Jason DeFilippo, to explore a journey that has defined much of their lives: their relationship with alcohol.

Their friendship, like many, was forged over countless pints and late-night conversations. Jason shares his harrowing story of a near-fatal stroke, a direct consequence of his long battle with alcohol. He walks us through his rock bottom, the terrifying physical and mental fallout, and the deliberate steps he took to reclaim his life.

Inspired by Jason's journey and facing his own health warnings, the Kevin opens up about his personal decision to explore sobriety, confronting the social anxiety and dependencies he's carried since childhood. Together, they deconstruct the meaning of alcoholism, the challenges and revelations of 12-step programs, and the surprising freedom found in making amends and living one day at a time.

This is more than a story about quitting drinking; it's a conversation about the courage to change, the power of vulnerability, and the evolution of a lifelong friendship.

[00:00] Introduction to Ordinary Consciousness

[00:54] Kevin's Personal Journey with Anxiety and Alcohol

[02:23] Reconnecting with an Old Friend

[03:04] Jason's Sobriety Journey

[03:39] Host's Realization and Decision to Change

[04:59] Exploring Sobriety and Tools for Change

[06:46] Early Experiences with Alcohol

[09:46] Childhood and Family Influences

[15:26] Adolescence and Coping Mechanisms

[21:34] College Years and Escalation

[27:41] Professional Life and Drinking Culture

[33:16] Early Drug Use and Experiences in San Francisco

[33:37] Memorable Nights and Stoned Adventures

[34:13] Drinking Habits and Social Events

[35:49 The Impact of Alcohol on Health

[37:19] Struggles with Alcohol Dependence

[39:53] The Turning Point: Health Scares and Realizations

[41:38] The Stroke: A Life-Changing Event

[43:53] Recovery and Reflections

[46:43] Understanding Alcoholism and Its Effects

[52:55] The Stroke Experience and Aftermath

[59:26] Birthday Relapse: A Sobering Experience

[01:01:46] The Downward Spiral: Losing Everything

[01:02:55] Rock Bottom: A Wake-Up Call

[01:05:15] Finding Help: The Road to Recovery

[01:06:48] The Power of Fellowship and Steps

[01:15:43] The Importance of Powerlessness

[01:24:26] Making Amends: Healing the Past

[01:27:47] Looking Forward: A New Beginning

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