The Tim Ferriss Show
The Tim Ferriss Show

#448: Brad Feld — The Art of Unplugging, Carving Your Own Path, and Riding the Entrepreneurial Rollercoaster

Brad Feld — The Art of Unplugging, Carving Your Own Path, and Riding the Entrepreneurial Rollercoaster | Brought to you by Laird Superfood, Theragun, and Thrive Market. "Brad, they can’t kill you and they can’t eat you. Suit up." — Len Fassler Brad Feld (@bfeld) is the author of two new bo

Featured Speakers

Tim Ferriss HostLen Fassler GuestAmy Batchelor GuestBrad Feld Guest

Topics Discussed

Episode Summary

Executive Summary: Tim Ferriss interviews investor-entrepreneur Brad Feld about the personal systems that let him sustain a high-intensity career: quarterly off-grid weeks, monthly “life dinners,” and clear relationship rules. Feld also discusses depression, OCD, therapy, complexity theory, startup communities, and why Boulder—not Silicon Valley—fits his life and values.

Main Topics: Off-grid vacations and relationship maintenance (Priority: 5/5): Feld explains how a crisis in his marriage led to a recurring practice of taking a full week off the grid each quarter, with no email, phone, or work, to protect his relationship and mental health. Mental health, OCD, and reducing shame (Priority: 5/5): He details his history of depression and OCD, why he began speaking publicly about it, and how openness, therapy, and feedback from others eliminated shame and improved leadership. Therapy, coaching, and self-inquiry (Priority: 4/5): Feld distinguishes therapy from coaching, describes how he chooses therapists through trusted referrals, and argues that effective growth combines radical self-inquiry with practical skill-building. Complexity theory and startup communities (Priority: 5/5): He defines simple, complicated, and complex systems, then applies complexity theory to startup ecosystems, arguing that communities evolve through feedback loops, not linear playbooks. Boulder, place, and topophilia (Priority: 4/5): Feld explains why he and Amy chose Colorado over Boston or Silicon Valley, emphasizing love of place, space, and a life built around values rather than the tech epicenter. Books, science fiction, and worldbuilding (Priority: 3/5): He recommends fiction and sci-fi as tools for thinking differently, highlighting works like Zen and the Art of Motorcycle Maintenance, Snow Crash, Neuromancer, Dune, and others. Marriage rituals and conflict management (Priority: 5/5): He describes monthly life dinners, communication rules during conflict, and the importance of not shutting down, not using violence, and apologizing sincerely.

Key Arguments: Sustained success requires deliberate boundaries; Feld’s quarterly off-grid weeks and monthly life dinners are systems for preserving marriage, health, and focus. Words must match actions; Feld’s marriage improved when he stopped prioritizing work interruptions over his commitments to Amy. Shame around depression and OCD is corrosive; public honesty and therapy can transform private struggle into connection and leadership strength. Therapy and coaching serve different purposes: therapy deconstructs the self and history, while coaching improves performance and craft. Startup communities are complex adaptive systems, so they cannot be built by copying Silicon Valley; they emerge from local feedback loops, recycling, and long-term commitment. A healthy ecosystem depends on positive-sum behavior from successful founders and investors who reinvest time, money, and expertise locally. Place matters deeply, but technology and remote work reduce the need to live in the epicenter; people can build meaningful lives in smaller, more aligned communities.

Data Points: Quarterly off-grid cadence: 4 weeks per year - Feld and Amy take a week off the grid each quarter, Saturday to Saturday. Off-grid duration: Saturday to Saturday - He says this timing gives the best off-ramp and on-ramp for disconnecting and re-entering work. Life dinner cadence: 1 dinner per month - A recurring monthly dinner on the first day of each month for retrospective and planning. Life dinner duration: 6 p.m. to 10 p.m. - The recurring calendar block Amy asked him to create for life dinner. Marriage length: almost 30 years - Feld says he and Amy have been together for nearly three decades. Marathons completed: 25 - Part of his goal to finish a marathon in each of the 50 U.S. states. Startup community book timing: 2012 - He references the first Startup Communities book as foundational and the sequel work as The Startup Community Way. Foundry Group founding year: 2007 - He notes the firm’s original partners committed to emotional availability from the start. Interliant peak market cap: $3 billion - He describes the company’s rise during the internet bubble before its collapse. Interliant burn rate: $5 million per month - He says the company mastered losing $5 million a month before the market turned. Interliant scale: 1,500 employees - He describes the company as a sizable business during the bubble era. Depression trigger period: 2013 - He identifies a major depressive episode after overtraining, injury, illness, and exhaustion in 2012. Kidney stone recovery: most of December - He took most of December off to recover before relapsing into depression at CES. Theragun starting price: $199 - Mentioned in the sponsor read, not the interview content. Thrive Market membership: $9.95/month or $59.95/year - Sponsor read details about membership pricing. AG1 bonus offer: 1-year supply of vitamin D + 5 travel packs - Sponsor read details for new subscribers.

Pivotal Quotes: "They can't kill you and they can't eat you. Suit up." — Len Fassler: A mentor’s encouragement to Feld during the collapse of Interliant and a period of intense professional and personal stress. "Your words don't match your actions." — Amy Batchelor: Amy’s core critique during the first off-grid vacation, which became foundational to Feld’s relationship philosophy. "Breathe." — Brad Feld: His suggested billboard message for the world, reflecting his emphasis on calm, presence, and self-regulation.

Implications: Listeners get a blueprint for sustainable high performance: build rituals, tell the truth about mental health, choose place intentionally, and treat communities as living systems. For founders, the message is that long-term ecosystems grow through trust, reciprocity, and patience—not shortcuts.

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About The Tim Ferriss Show

Tim Ferriss is a self-experimenter and bestselling author, best known for The 4-Hour Workweek. In this show, he deconstructs world-class performers from eclectic areas (investing, sports, business, art, etc.) to extract the tactics, tools, and routines you can use.

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