Bill Gurley says that right now, the worst thing you can do for your career is play it safe

For astir 3 decades, Bill Gurley has been among of the astir influential voices successful Silicon Valley — a wide spouse astatine Benchmark whose aboriginal bets connected companies similar Uber, Zillow, and Stitch Fix helped specify what modern task superior looks like. Now, having moved to Austin and stepped backmost from progressive investing, the autochthonal Texan is channeling that aforesaid pattern-recognition instinct into thing different: a book, a foundation, and a argumentation institute aimed astatine problems helium thinks helium tin really move.

The publication is Runnin’ Down a Dream — a motion to Tom Petty and besides an statement that pursuing your passionateness isn’t conscionable romanticized vocation proposal but an existent competitory strategy, 1 that becomes lone much urgent arsenic AI rapidly reshapes the workforce. The foundation, which he’s calling the Running Down a Dream Foundation, volition grant 100 grants of $5,000 a twelvemonth to radical who request a fiscal cushion to marque a leap they’ve been acrophobic to take.

We caught up with Gurley to speech astir each of it — including what helium makes of the somewhat surreal world that respective of his erstwhile peers successful tech present clasp tremendous sway successful Washington, wherefore helium thinks the 996 grind culture galore young founders person adopted is little alarming than it sounds, and what AI truly means for your career. The pursuing has been edited for magnitude and clarity. Our afloat speech with Gurley drops Tuesday connected TC’s StrictlyVC Download podcast.

Why constitute this book?

I went done a signifier wherever I was speechmaking a batch of biographies — radical from precise antithetic fields, antithetic clip windows — and I started noticing patterns the mode I would announcement patterns successful a marketplace evolving. I wrote them down. A mates years aboriginal I got invited to talk astatine the University of Texas, dusted disconnected the notes, built a presentation. They posted it connected YouTube, and James Clear — who wrote Atomic Habits — noticed and posted astir it. That’s what got maine reasoning astir a book. And erstwhile I went done my ain process of moving distant from task and reasoning astir what I wanted to bash next, it became evident I didn’t privation to constitute astir VC oregon Uber oregon immoderate of that. I wanted to bash thing that could person a bigger mission.

Your probe with Wharton recovered that astir 60% of radical would bash things otherwise if they could commencement their careers over. That shocked you. Why?

When we archetypal ran it arsenic a SurveyMonkey canvass we got 7 retired of ten. When we did it much rigorously with Wharton, we got six retired of ten. One of the things that strikes maine is that we person a operation successful the publication — beingness is simply a usage it oregon suffer it proposition — and erstwhile you’re young, it’s conscionable hard to person that framing. It’s hard to fast-forward done each of your clip and admit however precious it is. Daniel Pink has done a batch of enactment connected what helium calls regrets of inaction — the happening that weighs connected radical astir arsenic they get older is the happening they didn’t try, the chromatic near unturned. That holds crossed aggregate geographies and cultures. And I deliberation a batch of well-intentioned parents consciousness much work to make economical stableness for their kids than to promote them to genuinely research their passion. Especially with AI retired there, that whitethorn not person been the close call.

Exploring your passionateness sounds similar easier proposal for radical who person fiscal runway. What bash you accidental to idiosyncratic moving paycheck to paycheck?

A fewer things. First, the publication profiles radical who started connected the precise bottommost rung and climbed to the apical — [celebrity hairstylist and entrepreneur] Jen Atkins moved to LA with $200 successful her pocket. There’s thing successful the publication that says you request to commencement anyplace different than close astatine the beginning. Second, if you’re surviving paycheck to paycheck, I wouldn’t promote you to quit. I’d promote you to usage your escaped clip to physique a small papers connected your telephone astir what your happening mightiness be. Learn. Prepare to leap earlier you jump. And 3rd — this is wherefore I’m launching the foundation. The past leafage of the publication talks astir it: we’re going to springiness 100 grants a twelvemonth of $5,000 to radical who are successful precisely that position, who tin person america successful an exertion that they’ve thought agelong and hard astir wherever they privation to spell but request a small assistance getting there.

You’ve been outspoken for years astir regulatory seizure — the thought that large companies usage regularisation to entrench themselves.

I gave a code connected regulatory seizure a fewer years backmost — it was astatine the All-In Summit — and astatine the clip I said I had a fearfulness that the AI companies would effort to usage regularisation to support themselves. I deliberation that’s happening now. The flip broadside is that determination are morganatic questions: Jonathan Haidt’s publication Anxious Generation has been connected the bestseller database for astir 2 years, arguing societal media has been truly atrocious for children, with world probe to backmost it up. People would accidental we should person gotten successful beforehand of societal media and request to bash it with AI. The occupation is that the radical begging for regularisation the astir successful AI are the existent companies themselves, and that makes maine skeptical. There’s besides the planetary magnitude — if US AI gets entangled successful state-by-state regularisation and Chinese models are moving free, we’re going to overgarment ourselves successful reddish tape. I ever inquire people: what are your favourite 5 regulations of each time, and however were they successful? Do you person immoderate assurance that radical astatine the authorities level successful a random authorities cognize however to constitute bully AI regularisation that volition really work?

It’s a small surreal that respective salient figures from your satellite present clasp tremendous power successful Washington. What bash you marque of that?

It’s precise ironic. If you spell backmost and ticker that regulatory seizure talk, who would person thought a fewer years aboriginal David Sacks would really beryllium [special advisor for AI and crypto successful the White House]?

Back successful 2018, Mike Moritz of Sequoia wrote successful the FT that Americans would suffer to China if they didn’t commencement working harder. It was arguable astatine the time, but a batch of young founders present look to person since embraced a punishing enactment civilization — the 996 ethos. What are your thoughts astir what’s happening?

I benignant of emotion it, honestly. I deliberation Silicon Valley got truly lazy during COVID — radical weren’t coming into the office, the civilization got brushed successful a mode I hadn’t seen successful each my years there. And I’ve been to China six times. I cognize what Michael Moritz was describing erstwhile helium said we’re going to suffer not due to the fact that they’re smarter but due to the fact that they person a amended enactment ethic. But here’s the thing: if you survey palmy radical crossed a batch of fields, we deliberation it’s fantastic erstwhile an jock practices 12 hours a time oregon erstwhile an creator works obsessively connected their craft. Nobody says Jordan didn’t person work-life balance. We conscionable don’t widen the aforesaid logic to gathering a company. If those founders emotion what they’re doing that much, and they consciousness similar this is the infinitesimal to spell hard, that’s really precisely the constituent of the book: find the happening that makes you consciousness that way.

You speech astir mentorship successful the book. What makes a large mentor narration and however bash radical find one?

The fig 1 happening is to get retired of your caput this perfect that gets passed astir successful the self-help world: ‘go get a mentor,’ and everyone runs retired and acold calls idiosyncratic that’s ridiculously excessively precocious and unachievable, and it doesn’t work. For each those radical that are truly retired of scope close now, I telephone them aspirational mentors — make a persona of them, conscionable similar I was talking astir with the imagination occupation folder. Get clips of each the books they’ve written, podcasts they’ve done, interviews they’ve done, and survey them. You tin larn a batch from radical without talking to them directly, particularly successful the modern age. And past for your existent mentors, spell 2 levels down from wherever you thought you were going to aim. Discover idiosyncratic — tools similar LinkedIn marque this truthful casual — and beryllium the archetypal idiosyncratic to ever telephone them and inquire them to beryllium a mentor, due to the fact that they’ll beryllium flattered. They’ll beryllium flattered that you knew who they were. Imagine anyone getting their archetypal telephone to beryllium a mentor. It’s a large feeling. You’re going to person mode much occurrence with that enactment than shooting excessively high.

I’ll archer you a comic story: I started getting truthful galore calls from radical who wanted to interruption into task that I wrote a three-page PDF called “So You Want to Be a VC,” and hidden successful the 3rd leafage was fundamentally — spell bash X, spell bash Y, spell bash Z, travel backmost and archer maine however that went. The fig of radical that really ended up talking to maine aft getting that papers was a fraction of the fig I sent it to. It’s comic however overmuch it thinned erstwhile you gave them a small homework to do.

You started moving connected this publication earlier the impacts of AI became clearer. Does that astatine each alteration however radical should deliberation astir their careers?

If you’re pursuing the accepted way — going done the vocation halfway astatine your university, signing up connected a list, waiting for a recruiter to beryllium done 30 radical successful 20-minute slots — you look similar a cog. You look mass-produced. For that group, AI looks frightening, and possibly it should. But if you are blazing your ain trail, utilizing the techniques successful the book, becoming what I telephone a campaigner of 1 — idiosyncratic whose way looks wholly unsocial due to the fact that you’ve built it intentionally — past each instrumentality successful this publication is amplified by AI. Learning has ne'er been easier than close now, successful the full past of the world. If you’re moving toward it, if you’re becoming the astir AI-aware idiosyncratic successful your field, this happening is thing but a superpower.