Bill Gurley: Break Free From Career Regret and Design Work You Love | Career | E387

Bill Gurley (0:00)

I feel deeply sad for a lot of founders. There is a reality where a modern venture capitalist does not want to take a meeting in anything on AI.

Hala Taha (0:11)

Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor, known for early investments in companies like Uber, Zillow, and Nextdoor.

Bill Gurley (0:21)

People aren't that engaged and happy in their careers. We asked a thousand people, if you could start your career over again, would you do something different? Seven out of ten said yes.

Hala Taha (0:31)

Wow.

Bill Gurley (0:32)

AI is moving so fast. My advice for anyone in any field that's afraid of AI is run at it.

Hala Taha (0:39)

You also started your career at the start of the dot-com bubble, and you saw that whole thing explode. How did that actually change the way you think about investing in companies, change the way you think about sustainability?

Bill Gurley (0:53)

One of the things that happens anytime there's a technology wave is, people get rich quick, and then a whole bunch of people see people getting rich quick and they rush in. I like it when they're not around. When you're in a bubbly time, than we may be right now with AI, people do silly things, things that don't usually work. They get very speculative.

Hala Taha (1:13)

You've been ahead of the curve so many times. Can you give us a prediction about the future of work or technology, something that we might be underestimating or unexpected?

Bill Gurley (1:22)

I think there will be a lot of money made in...

Hala Taha (1:27)

Yeah, fam, 7 out of 10 people say they'd choose a different career if they could start over. And it's not because they lack talent, it's because they chose the safe path. Today's guest has had a front row seat to what actually drives long-term success. Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor, known for early investments in companies like Uber, Zillow and Nextdoor. After decades backing billion-dollar founders, he noticed a pattern. In his work, the most successful people didn't follow the conventional route. They built careers around what genuinely fascinated them. In this episode, we unpack lessons from Bill's new book, Running Down a Dream, including how to avoid career regret, staying relevant in the age of AI, and designing a career driven by curiosity, smart pivots, and continuous learning. Bill, welcome to Young and Profiting Podcast.

Bill Gurley (2:16)

Thanks for having me on.

Hala Taha (2:17)

I'm so excited for this podcast. You know, I've heard about you for a very long time. Now we get a chance to sit down together. So you are what people have called a super investor. And now you've come out with a careers book called Running Down a Dream.

Bill Gurley (2:33)

Correct.

Hala Taha (2:34)

And a lot of people might be thinking like, what does a VC guy know about careers and why is he putting out a book about careers? You could be, you know, putting out a war book on Uber or your Times at Benchmark, the VC firm, right? So why did you decide to write a book about careers?

Bill Gurley (2:49)

You know, as I reached the end of what was definitely my dream job, I loved being a venture capitalist, but I reached a point where I decided it was time to hang up my boots and it was time for me to move on and leave the field for younger people to succeed.

I felt a calling to write this book and it was something that I had stumbled upon like eight years ago, an idea that had popped into my head. I used to write a lot of blog posts and when I would get an idea, I would scratch it down and sometimes it would become a post, a lot of times it just was living in a document. And this one was an idea that came to me and I had read these three biographies and noticed that these three people had all done similar things. And I wrote down the notes, I then got invited to give a speech at the University of Texas here in Austin, and I put it together and gave that speech. And then a number of people saw that speech, probably most notably James Clear. And people then started pushing me, one day you should make that a book. And as I reached the end of my career, people had talked to me about writing a book before. You're right, I could have written about investing, I could have written about tech, I could have written about venture capital, I could have written about Uber. And this just felt more personal to me. And now that it's done and it took a long time, I'm certain at this point that this book has a bigger chance to help more people than any of those other books could have.