Brad Feld — The Art of Unplugging, Carving Your Own Path, and More! | The Tim Ferriss Show

Brad Feld walks Tim Ferriss through the origins of his quarterly off-the-grid vacations, sparked by his wife Amy telling him 'I'm done' during the dot-com collapse when his words stopped matching his actions. He opens up candidly about his OCD, his decades of depression, the shame he eventually obliterated by blogging publicly about it in 2013, and how coach Jerry Colonna reshaped his approach to vulnerability. Feld details practical relationship systems he and Amy built, monthly 'life dinners' run like agile retrospectives, digital sabbaths, and conflict ground rules. He closes by explaining why he chose Boulder over Silicon Valley, his love of science fiction, and how complexity theory underpins his framework for building startup communities.

• Feld's first off-grid vacation came after Amy quietly told him 'I'm done' in mid-2000 during the internet-bubble deflation, meaning she'd had enough of how he was living, not just the bad week he assumed she meant.
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• The foundational lesson from that weekend was that his words didn't match his actions, answering random phone calls during dinner while claiming Amy was the most important person in his life.
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• Since 2000 he and Amy take a week off the grid every quarter (Saturday to Saturday), and it took over a year to detox from the anxiety of disconnecting.
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• Feld publicly identifies as DSM-5 OCD, a counter, arranger, and checker, and in 2013 began openly blogging about his struggles with anxiety and depression after a new therapy session.
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• Coach Jerry Colonna told him he could be a better leader simply by being himself and letting go of constraints, prompting Feld to return to therapy and write publicly about it.
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• Feld and Amy created monthly 'life dinners' on the first of each month, run like an agile retrospective and sprint planning session, now over a thousand dinners across 20-plus years.
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• Their conflict ground rules: never any physical violence (a redline), never shut down during a fight, and both partners give a real apology when it's over.
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• The Startup Community Way crystallized when co-author Ian Hathaway framed a startup community as a complex adaptive system, distinct from a deterministic simple or complicated system.
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• Feld archives all emails received during his off-grid weeks and tells senders to resend after he returns, so he can start Monday with an empty inbox instead of reliving the prior week.
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• His ASP-era company Inter-Reliant hit a peak market cap of about $3 billion with 1,500 employees, but mastered 'the art of losing $5 million a month' and collapsed when the bubble burst.
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• His mentor Len Fassler hugged him during the collapse and said 'they can't kill you and they can't eat you, suit up', a line Feld calls one of his most important professional moments.
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• At MIT Feld scored 20 out of 100 on his first freshman physics test and cried for an hour, only later learning the class average was 32, making it roughly a B-minus.
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• Feld explains OCD as an inappropriate linkage between obsessive thoughts and compulsive behaviors, like straightening cigarettes on the street to prevent his wife from having an affair.
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• His magic number is three, so he repeats rituals three times, and if he makes a mistake, his engineer's brain escalates it to nine, then 27, then potentially 81 times.
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• Feld keeps a digital sabbath from Friday night to Sunday morning roughly 80 percent of the time; when he skipped it for three weeks during COVID he felt completely broken.
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• Amy's only requirement for where to live was 'ocean or mountains,' and about two months before Feld turned 30 she told him 'I'm moving to Boulder and you can come with me if you'd like.'
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• Feld learned the word 'topophilia', love of place, from former Colorado governor John Hickenlooper, who helped create the microbrewery industry.
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• For his billboard, Feld would put 'breathe' for the world and 'don't believe your own [expletive]' for Silicon Valley, plus 'they can't kill you and they can't eat you.'
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