Gurley contrasts Austin Ventures' advice to work twenty years before VC with Benchmark's opposite approach.
“And they said, go work for twenty years and then get in. And it's ironic when I think back to that moment in time because we have kind of the exact opposite process.”
Gurley cites surveys showing 70% then 60% would restart careers differently if possible.
“We did this survey and asked people if you could start your career over again, would you do things differently? And in that survey, 70% of people said yes.”
Gurley's Wharton survey found six in ten people would choose a different career if they could go back.
“It led to us doing this survey with Wharton where we asked people, if you could go back in life, would you choose a different career? And six in 10 people say yes.”
Gurley's survey found seven out of ten people would choose a different career if they could start over.
“We ask a thousand people, if you could start your career over again, would you do something different? Seven out of 10 said yes.”
Gurley argues Silicon Valley offers daily networking events that accelerate learning and connections by 10X or more.
“if you're in Silicon Valley and you have time, you can find an event every night. And at that event, you might meet a peer.”
Gurley's Wharton survey found sixty percent of people would choose a different career path if starting over.
“We did a survey with Wharton and said, if you could go back and start over, would you choose a different career path? And sixty percent of people said yes.”
Gurley used a thirty-year thought experiment to test career fit, mirroring Bezos's eighty-year self framework.
“I don't know that I said, I'm doing this exercise kind of like Bezos did when he started. But I said to myself, do I see myself doing this thirty years from now?”
Gurley describes Fidel stalking General Magic for six months after reading Rolling Stone, passing up Apple offer.
“These were the individuals of Apple and they had all left to go to a company, General Magic. He didn't know what they did.”
Gurley walked Wall Street offices late at night to visualize his future as a senior analyst.
“I walked around the office late one night, about 10PM Park Avenue Plaza and the 63rd, 36th Floor and the corner offices were the most senior sell side analysts.”
Gurley argues those who craft bespoke career paths can view AI as jet fuel rather than threat.
“I think you view AI as jet fuel, as something that's going to make what you're capable of even better.”
Gurley cites 2023 Gallup poll showing 53% of people are disengaged at work.
“there was a Gallup poll in 2023 that like 53% of people are disengaged at work. And that's not great. We've all heard about quiet quitting.”
Gurley says regrets of inaction weigh on people's minds more heavily over time than mistakes made.
“the thing we never did, the thing we always thought we should do that we didn't get to, those things weigh on our brain more and more and more as we get older.”
Gurley says Silicon Valley has nightly networking events that massively increase probability of lucky career breaks.
“And on top of all that, what I just said, a lot of people talk about luck in their career path.”
Gurley argues those who best understand AI's impact on their role won't be laid off.
“if there are 40 people in your org all doing the same thing, and you understand how AI affects that role more than the rest of them, you're not getting laid off.”
Gurley argues AI is a jetpack for people running their own lane with bespoke passion and goals.
“For that individual, is AI a threat or is it a jetpack? I actually think it's a jetpack because now I can go learn about anything I want.”
Gurley says AI is a huge threat to people following a conveyor belt career path without differentiation.
“I think those people, AI is a huge threat because they're like, they don't really know why they're there.”
Gurley recounts Quatrone offering to move him to Silicon Valley and introduce him to every venture capitalist.
“And I said, I think I want to be a venture capitalist. And he said, this almost sounds too good to be true.”
Gurley's Wharton survey found six in ten people would choose a different career path if starting over.
“We hired we hired Wharton to do an official academic review, and that one came out six and ten. There's a book by Daniel Pink about regrets called the power of regrets.”
Gurley cites Stanford research showing 40% of people shift away from their college major within four to five years.
“But a lot of people do. There's Dave Evans at Stanford who does the Designing Your Life class and book, you know, they highlight that like four years, five years out, 40% of people are no longer doing the work that was in their major.”
“I paused in each one of them and said, do I want to be here thirty years from now, like in that office?”
Gurley criticizes schools requiring major declaration as high school juniors when students cannot know their passion yet.
“Now at many schools, you have to apply to your major, like, as you're applying to college. So you're a junior in high school and people are like, what's your passion?”
“I ended up in Silicon Valley and got into venture capital and spent twenty five years there and never asked myself that question again.”
“And I paused in each one of them and said, do I want to be here thirty years from now, like in that office?”
Gurley cites 2023 Gallup poll showing over 50% aren't engaged at work, only 23% qualify as engaged.
“If you're unfulfilled at work, there's a 2023 Gallup poll study that came out and said over 50% of people aren't actively engaged at work. And the number that qualifies engaged is like 23%.”
Gurley reports survey finding that 60% of people would choose a different career if starting over.
“we did a survey where we asked people if you could go back in time and start your career over again, would you do something different? And six out of 10 said yes.”
Gurley announces foundation giving 105 grants annually to people financially stuck but wanting to chase their dreams.
“I'm also starting launching a foundation. I've already set aside the money, but I'm gonna give a $105 grants a year to people who want to chase their dreams, but maybe a little stuck financially and need a little help to get there.”
Gurley describes hating traditional college hiring with 30 candidates getting fifteen minute slots each
“You got to stand out next to everyone that's just like you. And it seems so unoptimal to me.”
Gurley describes his heuristic of asking whether he could see himself doing the same job thirty years later.
“I one day thought to myself, do I see myself doing this thirty years from now?”
Gurley explains that regrets of inaction intensify with age more than mistakes made.
“Daniel has, in his book on regrets, talks a lot about regrets of inaction. He calls them boldness regrets.”
Gurley cites data showing over 50% of people work outside their college major ten years after graduation.
“Like over 50% of people are no longer working in the career that was was stated by their major. And I bet that number's getting worse.”
Gurley offers heuristic for career decisions: ask yourself if you see doing current job thirty years from now.
“But I then had a reflection and this is the heuristic I think people can use. I, I one day thought to myself, do I see myself doing this thirty years from now?”
Gurley cites Tito's founder who worked twenty years in other fields before starting vodka company.
“There's a gentleman named Burt Beveridge who was a seismologist undergrad, worked in oil and gas for ten years, got scared actually because he was in Latin America, things got dicey, became a mortgage broker for another ten years, and then one weekend convinced himself to launch a vodka company named Tito's,”
Gurley changed careers twice using the thirty-year test before finding his path to venture capital.
“I went to MBA school, I went to Wall Street, worked there for three years, had the same discussion with myself, which got me looking in a different direction,”
Gurley warns that rote knowledge taught in school is already in AI models, making it an unsafe career position.
“If you just arm yourself with the road algorithms that they taught you in school, those are in the models.”
Gurley found pattern across three biographies where people started with high intentionality at the lowest rung.
“I read these three biographies of people that were in very different fields and just, it all started with high intention at the lowest rung”
Gurley says Brett Taylor became an AI expert in three years despite not being one previously.
“Well guess what like three years ago he wasn't an AI expert but he became one.”
Gurley advises moving to your industry's epicenter because it amplifies learning, mentorship, peers, and optionality.
“If your industry has an epicenter, and we're sitting in an epicenter, but like if like, and you are confident this is your fascination lane, you should go.”
Gurley argues fascination makes learning free and energizing rather than draining like studying uninteresting subjects.
“when you're fascinated with something, the learning is free. Like like you you study things for fun.”
Gurley argues moving to an industry's epicenter amplifies all career advantages including learning, mentors, and peers.
“Because all the other principles in the book get better. So I talk about continuous learning, I talk about finding mentors, I talk about finding peers.”
Gurley says being at the industry epicenter amplifies all career principles because continuous learning, mentors, peers, and optionality happen naturally.
“all the other principles in the book get better. So I talk about continuous learning, I talk about finding mentors, I talk about finding peers. Like, all those things in the epicenter happen continuously.”
Gurley cites Daniel Pink's research showing regrets of inaction are the number one regret people have at end of life.
“And the number one thing people regret at the end of their lives is what he calls boldness regrets, their regrets of inaction.”
Gurley argues the best jobs for thriving come from creating opportunities yourself rather than waiting for posted positions.
“I think the best jobs for, like, you to really thrive are ones where you go and create the opportunity yourself.”
Gurley argues fascination makes learning effortless and energizing, while unfascinating work depletes energy and requires breaks.
“Like like you you study things for fun. Like like you get done reading it, you go, ah, you wanna tell somebody you're excited, you get energy.”
Gurley says being the most AI productive person in your field makes you indispensable and sought after.
“if you are the most AI productive human in your field, you're not getting fired. Like, you're you're the one they're asking all the questions of.”
Gurley says he developed skills in synthesizing and communicating through blogs and podcasts during his venture career.
“I've, I've developed a pretty good rhythm about being able to synthesize and communicate. So I did that in my venture career through blogs and eventually things like podcasts.”