Tech
Bill Gurley says that right now, the worst thing you can do for your career is play it safe
For nearly three decades, Bill Gurley has been among of the most influential voices in Silicon Valley — a general partner at Benchmark whose early bets on companies like Uber, Zillow, and Stitch Fix helped define what modern venture capital looks like. Now, having moved to Austin and stepped back from active investing, the native Texan is channeling that same pattern-recognition instinct into something different: a book, a foundation, and a policy institute aimed at problems he thinks he can actually move.
The book is Runnin’ Down a Dream — a nod to Tom Petty and also an argument that following your passion isn’t just romanticized career advice but an actual competitive strategy, one that becomes only more urgent as AI rapidly reshapes the workforce. The foundation, which he’s calling the Running Down a Dream Foundation, will award 100 grants of $5,000 a year to people who need a financial cushion to make a leap they’ve been afraid to take.
We caught up with Gurley to talk about all of it — including what he makes of the somewhat surreal reality that several of his former peers in tech now hold enormous sway in Washington, why he thinks the 996 grind culture many young founders have adopted is less alarming than it sounds, and what AI really means for your career. The following has been edited for length and clarity. Our full conversation with Gurley drops Tuesday on TC’s StrictlyVC Download podcast.
Why write this book?
I went through a phase where I was reading a lot of biographies — people from very different fields, different time windows — and I started noticing patterns the way I would notice patterns in a market evolving. I wrote them down. A couple years later I got invited to speak at the University of Texas, dusted off the notes, built a presentation. They posted it on YouTube, and James Clear — who wrote Atomic Habits — noticed and posted about it. That’s what got me thinking about a book. And when I went through my own process of moving away from venture and thinking about what I wanted to do next, it became obvious I didn’t want to write about VC or Uber or any of that. I wanted to do something that could have a bigger mission.
Your research with Wharton found that roughly 60% of people would do things differently if they could start their careers over. That shocked you. Why?
When we first ran it as a SurveyMonkey poll we got seven out of ten. When we did it more rigorously with Wharton, we got six out of ten. One of the things that strikes me is that we have a phrase in the book — life is a use it or lose it proposition — and when you’re young, it’s just hard to have that framing. It’s hard to fast-forward through all of your time and recognize how precious it is. Daniel Pink has done a lot of work on what he calls regrets of inaction — the thing that weighs on people most as they get older is the thing they didn’t try, the stone left unturned. That holds across multiple geographies and cultures. And I think a lot of well-intentioned parents feel more responsibility to create economic stability for their kids than to encourage them to truly explore their passion. Especially with AI out there, that may not have been the right call.
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Exploring your passion sounds like easier advice for people who have financial runway. What do you say to someone working paycheck to paycheck?
A few things. First, the book profiles people who started on the very bottom rung and climbed to the top — [celebrity hairstylist and entrepreneur] Jen Atkins moved to LA with $200 in her pocket. There’s nothing in the book that says you need to start anywhere other than right at the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t encourage you to quit. I’d encourage you to use your free time to build a little document on your phone about what your thing might be. Learn. Prepare to jump before you jump. And third — this is why I’m launching the foundation. The last page of the book talks about it: we’re going to give 100 grants a year of $5,000 to people who are in exactly that position, who can convince us in an application that they’ve thought long and hard about where they want to go but need a little help getting there.
You’ve been outspoken for years about regulatory capture — the idea that big companies use regulation to entrench themselves.
I gave a speech on regulatory capture a few years back — it was at the All-In Summit — and at the time I said I had a fear that the AI companies would try to use regulation to protect themselves. I think that’s happening now. The flip side is that there are legitimate questions: Jonathan Haidt’s book Anxious Generation has been on the bestseller list for almost two years, arguing social media has been really bad for children, with academic research to back it up. People would say we should have gotten in front of social media and need to do it with AI. The problem is that the people begging for regulation the most in AI are the actual companies themselves, and that makes me skeptical. There’s also the global dimension — if US AI gets entangled in state-by-state regulation and Chinese models are running free, we’re going to paint ourselves in red tape. I always ask people: what are your favorite five regulations of all time, and how were they successful? Do you have any confidence that people at the state level in a random state know how to write good AI regulation that will actually work?
It’s a little surreal that several prominent figures from your world now hold enormous influence in Washington. What do you make of that?
It’s very ironic. If you go back and watch that regulatory capture talk, who would have thought a few years later David Sacks would actually be [special advisor for AI and crypto in the White House]?
Back in 2018, Mike Moritz of Sequoia wrote in the FT that Americans would lose to China if they didn’t start working harder. It was controversial at the time, but a lot of young founders here seem to have since embraced a punishing work culture — the 996 ethos. What are your thoughts about what’s happening?
I kind of love it, honestly. I think Silicon Valley got really lazy during COVID — people weren’t coming into the office, the culture got soft in a way I hadn’t seen in all my years there. And I’ve been to China six times. I know what Michael Moritz was describing when he said we’re going to lose not because they’re smarter but because they have a better work ethic. But here’s the thing: if you study successful people across a lot of fields, we think it’s wonderful when an athlete practices 12 hours a day or when an artist works obsessively on their craft. Nobody says Jordan didn’t have work-life balance. We just don’t extend the same logic to building a company. If those founders love what they’re doing that much, and they feel like this is the moment to go hard, that’s actually precisely the point of the book: find the thing that makes you feel that way.
You talk about mentorship in the book. What makes a great mentor relationship and how do people find one?
The number one thing is to get out of your head this ideal that gets passed around in the self-help world: ‘go get a mentor,’ and everyone runs out and cold calls someone that’s ridiculously too high and unachievable, and it doesn’t work. For all those people that are really out of reach right now, I call them aspirational mentors — create a persona of them, just like I was talking about with the dream job folder. Get clips of all the books they’ve written, podcasts they’ve done, interviews they’ve done, and study them. You can learn a lot from people without talking to them directly, especially in the modern age. And then for your real mentors, go two levels down from where you thought you were going to aim. Discover somebody — tools like LinkedIn make this so easy — and be the first person to ever call them and ask them to be a mentor, because they’ll be flattered. They’ll be flattered that you knew who they were. Imagine anyone getting their first call to be a mentor. It’s a great feeling. You’re going to have way more success with that interaction than shooting too high.
I’ll tell you a funny story: I started getting so many calls from people who wanted to break into venture that I wrote a three-page PDF called “So You Want to Be a VC,” and hidden in the third page was basically — go do X, go do Y, go do Z, come back and tell me how that went. The number of people that actually ended up talking to me after getting that document was a fraction of the number I sent it to. It’s funny how much it thinned when you gave them a little homework to do.
You started working on this book before the impacts of AI became clearer. Does that at all change how people should think about their careers?
If you’re following the traditional path — going through the career center at your university, signing up on a list, waiting for a recruiter to sit through 30 people in 20-minute slots — you look like a cog. You look mass-produced. For that group, AI looks frightening, and maybe it should. But if you are blazing your own trail, using the techniques in the book, becoming what I call a candidate of one — someone whose path looks completely unique because you’ve built it intentionally — then every tool in this book is amplified by AI. Learning has never been easier than right now, in the entire history of the world. If you’re running toward it, if you’re becoming the most AI-aware person in your field, this thing is nothing but a superpower.
Tech
Sam Altman would like to remind you that humans use a lot of energy, too
OpenAI CEO Sam Altman addressed concerns about AI’s environmental impact this week while speaking at an event hosted by The Indian Express.
For one thing, Altman — who was in India for a major AI summit — said concerns about AI’s water usage are “totally fake,” though he acknowledged it was a real issue when “we used to do evaporative cooling in data centers.”
“Now that we don’t do that, you see these things on the internet where, ‘Don’t use ChatGPT, it’s 17 gallons of water for each query’ or whatever,” Altman said. “This is completely untrue, totally insane, no connection to reality.”
He added that it’s “fair” to be concerned about “the energy consumption — not per query, but in total, because the world is now using so much AI.” In his view, this means the world needs to “move towards nuclear or wind and solar very quickly.”
There’s no legal requirement for tech companies to disclose how much energy and water they use, so scientists have been trying to study it independently. Data centers have also been connected to rising electricity prices.
Citing a previous conversation with Bill Gates, the interviewer asked whether it’s accurate to say a single ChatGPT query currently uses the equivalent of 1.5 iPhone battery charges, to which Altman replied, “There’s no way it’s anything close to that much.”
Altman also complained that many discussions about ChatGPT’s energy usage are “unfair,” especially when they focus on “how much energy it takes to train an AI model, relative to how much it costs a human to do one inference query.”
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“But it also takes a lot of energy to train a human,” Altman said. “It takes like 20 years of life and all of the food you eat during that time before you get smart. And not only that, it took the very widespread evolution of the 100 billion people that have ever lived and learned not to get eaten by predators and learned how to figure out science and whatever, to produce you.”
So in his view, the fair comparison is, “If you ask ChatGPT a question, how much energy does it take once its model is trained to answer that question versus a human? And probably, AI has already caught up on an energy efficiency basis, measured that way.”
You can watch the full interview below. The conversation about water and energy usage begins at around 26:35.
Tech
The 9,000-pound monster I don’t want to give back
Before heading on a trip to Tahoe last weekend, GM offered me the use of the company’s 9,000-pound monument to excess – the new 2026 electric Escalade IQL (starting at $130,405) – for a week to test-drive. Before you continue, note that I’m not a professional car reviewer. TechCrunch has excellent transportation writers; I am not one of them. I do, however, drive an electric car.
I was immediately game. I’d first glimpsed one last summer at a car show, where some regional car dealers had stationed themselves at the end of a long field dotted with exquisite vintage automobiles. My immediate reaction was “Jesus, that’s enormous,” followed by a surprising admiration for its design, which, despite its enormous scale, shows restraint. For lack of a better word, I’m going to say it’s “strapping.” Its proportions just work.
My excitement waned pretty quickly when the car was dropped off at my house a day before our departure time. This thing is a monstrosity — at 228.5 inches long and 94.1 inches wide, it made our own cars look like toys. My first apartment in San Francisco was smaller. Trying to drive it up my driveway was a little harrowing, too; it’s so big, and its hood is so high, that if you’re ascending a road at a certain slope – we live midway down a hill; our mailbox is at the top of it – you can’t see whatever is directly in front of the car.
I thought about just leaving it in the driveway for the duration of the trip. The other alternative was doing what I could to grow more comfortable with the prospect of driving it 200 miles to Tahoe City, so I tooled around in it that night and the next day, picking up dinner, heading to an exercise class — just basic stuff around town. When I ran into a friend on the street, I volunteered as quickly as possible that this was not my new car, that I was going to possibly review it, and wasn’t its size ridiculous? It felt like a tank. I thought: other than hotels that use SUVs like the Escalade to ferry guests around, what kind of monster chooses a car like this?
Five days later, it turns out that I am that kind of monster.
Look, I don’t know how or when I fell for this car. If I’d written this review after two days, it would read very differently. Even now, I’m not so blind that I don’t see its shortcomings.
It was the Escalade’s performance in a terrible snowstorm that really won my heart, but let me walk you through the steps between “Ugh, this car is a tank” and “Yes! This car is a tank.”
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Just getting into it requires a little more exertion than would seem to make sense. I’m fairly athletic and I still found myself wondering if this thing shouldn’t come with an automated step stool.
Inside is where digital maximalism does its work. The dashboard opens with a 55-inch curved LED screen with 8K resolution that reads less like a car display and more like a situation room. Front passengers get their own screens. Second-row passengers also get 12.6-inch personal screens along with stowable tray tables, dual wireless chargers, and — with the most lavish version of the car — massage seats that will make them forget they’re in a vehicle at all. Google Maps handles navigation. And the polarized screen technology deserves its own praise: while one of my kids binge-watched Hulu in the front seat, not a frame of it leaked into my sightline from behind the wheel.
The cabin itself is built around the premise that no one inside should feel crowded, and it delivers. Front legroom stretches to 45.2 inches; the second row offers 41.3; even the third row manages 32.3 inches. Seven adults could share this machine for a long while without fraying each other’s nerves. Heated and ventilated leather seats with 14-way power adjustment come standard in the first two rows, and the whole operation runs on 5G Wi-Fi.
The car also comes standard with Super Cruise, GM’s hands-free driving system, which I’m not sure I quite figured out. True car reviewers seem to love it; when I tried it, the car felt like it was drifting to an alarming degree between the outer boundaries of the highway lane, and when that happens, it unleashes an escalating sequence of warnings. First, a red steering wheel icon materializes on-screen. Then your seat pulses haptic warnings against your rump. Ignore those and a chime — both reminder and reproach — fills the cabin. GM calls this impolite series a “driver takeover request.”
Did I mention the 38-speaker AKG Studio sound system? So good.
As for the exterior — this is a handsome giant, but it takes some getting used to. At first, I found the grille, which is just for show, almost comically imposing. This is definitely a car for people who are the boss, or want to be the boss, or want to look like the boss while privately dealing with existential crises. Pulling up to a glass-lined restaurant one night, I’m pretty sure I blinded half the patrons as I swung into a parking spot perpendicular to the building, the Escalade’s headlights flooding through the windows.
Then there is the light show the car launches whenever it detects you approaching via the key or the MyCadillac app. It’s as if it’s saying, “Hey, chief, where we headed?” before you’ve so much as touched a door handle. (In the vernacular of Cadillac, this is thanks to its “advanced, all-LED exterior lighting system,” highlighted by a “crystal shield” illuminated grille and crest, along with vertical LED headlamps and “choreography-capable tail lamps.”)
It is, objectively, a bit much. I loved it immediately.
Despite its size, the Escalade IQL is unexpectedly nimble. Not “sports car darting through traffic” nimble, but “I can’t quite believe something this colossal doesn’t handle like a battleship” nimble.
Now we arrive at the frustrations. The front trunk — or “frunk” in the lexicon of EV devotees — operates in mysterious and frustrating ways. Opening requires holding the button until completion. Release prematurely and it halts mid-ascent, forcing you to restart the entire sequence. Closing demands the same sustained pressure. The rear trunk, conversely, requires two distinct taps followed by immediate button abandonment. Hold too long and nothing happens.
Relatedly, twice, the vehicle refused to power down after I’d finished driving. The car simply sat there, running, even when I shifted to park and opened the door (which tells the car to turn off). One clunky solution: open the frunk, close the frunk, shift into drive, then park, then exit.
As for the software, it’s absolutely fine unless you’ve owned a Tesla, in which case, prepare for disappointment. This seems to be true across the board — everyone I know who owns both a Tesla and another EV, no matter how high end, says the same thing. Once you’ve internalized how effortlessly Tesla’s software dissolves barriers between intention and execution, every other automaker’s software feels like a compromise.
Which brings us to the nadir of the trip: charging in Tahoe during winter. For all its virtues, the Escalade IQL is, by any measure, a thirsty machine. The battery is a 205 kWh pack — enormous, and it needs to be, because the car burns through roughly 45 kWh per 100 miles, which is considerably more than comparable electric SUVs. Cadillac estimates 460 miles of range on a full charge, and in ideal conditions that holds up. Tahoe in winter, however, is not ideal conditions. We’d also arrived with less charge than we should have. A series of side trips on the way up, including an emergency detour to find shirts for a family member who had packed none, had eaten into the battery more than expected. By the time we needed to charge, we genuinely needed to charge.
We approached a Tesla Supercharger in Tahoe City that appeared on the MyCadillac app, but when we plugged in to the designated stall, nothing happened. We searched for answers, discovering that even Tesla stations that accept non-Tesla vehicles throttle energy to 6 kilowatts per hour anyway, but it was a frustrating experience. A nearby EVGo had shuttered a month prior. ChargePoint’s two units at the Tahoe City Public Utility lot were broken and willing to connect but not to actually charge anything. We briefly contemplated a 35-mile drive to Incline Village, did the math on what stranded would actually look like, and decided against it. Then I discovered an Electrify America station 12 miles away. We drove through gathering snow, arrived shortly before 11 p.m., and it worked. We sat there for an hour fighting exhaustion before driving home.
The following morning revealed another issue via an app alert: tire pressure had dropped to 53 and 56 PSI in the front (recommended: 61) and 62 PSI in the rear (recommended: 68). I have no idea whether the car had been delivered that way or whether something else was going on beyond the cold weather — either way, it meant someone standing at a gas station filling tires while being pelted directly in the face with ice. (That someone was my husband.) For a family trip, it was going great.
At this point, in fact, I would have told you that the Escalade IQL is unquestionably luxurious and ideal for families of four or more who value space and technology. I would tell you it came burdened by real tradeoffs: forward visibility obstructed by its commanding hood, parking challenges inherent to its dimensions, limited charging infrastructure for a machine this ravenous, and tires tasked with supporting 9,000 pounds. It’s a beautiful car, I would have said, but it’s not for me.
But the snow that had started to fall kept falling. Within two days, eight feet had accumulated, making it impossible to ski — the entire point of the trip — and terrifying to move about town. Except I found that I wasn’t terrified because we had the Escalade, which, because of its weight, felt like driving a tank through the snow. (The tires held steady after we’d inflated them, even as the week kept doing its worst.) What could have been harrowing felt serene. It was quiet, it was strong, it was taking charge in a bad situation.
I also adjusted to the size. By the end of this past week I had stopped mouthing “I’m sorry” to whoever who was waiting for me to figure out where to park it. I had stopped caring what it said about me that I was driving a car whose entire design philosophy is: the owner of this vehicle is not waiting in line. Eight feet of snow had fallen, we needed groceries, and I was the one with the tank, suckers! I could sense my husband falling for the car, too.
Then, as tends to happen in Tahoe, the snow stopped all at once and the sun came out, and the Escalade was just a very dirty car sitting in the driveway (sorry, GM!). It was in this moment that I realized: I still like it, and it’s not because of the emergency alone. I love riding high, with the speaker system flooding the car with a favorite soundtrack. That light show still gets me. The car’s long, curved LED screen is a marvel, among other features.
The frunk is still problematic. I won’t soon forget the panic of not being able to charge the car where I thought I could. Parking this thing is truly an exercise in patience. I have strong opinions about unnecessary consumption. None of that has changed.
I just also, somehow, want this car, so when the GM middleman comes to collect it, I may hide it under a tarp — a very large tarp — and tell him he has the wrong address.
Tech
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