Bill Gurley: The Biggest Career Regret Most People Have

Paula Pant (0:00)

Are you feeling stuck in your career? A lot of people are not very excited about what they're going to do five days a week. You know, you wake up at 6 a.m. or 7 a.m., and you're going to spend the bulk of your waking hours doing this thing that isn't really that exciting. That kind of sucks. Venture capitalist Bill Gurley joins us to talk about what to do if you feel stuck in your career and you're not sure what direction you should take. Welcome to the Afford Anything podcast, the show that knows you can afford anything, not everything. The show covers five pillars. Financial psychology, increasing your income, investing, real estate, and entrepreneurship. It's double-eye fire. I'm your host, Paula Pant, and today's episode covers two out of those five. We talk about increasing your income, which is the natural organic consequence of doing something that's more aligned with you, with the real you, the inner you. And then we also talk, I mean, we don't explicitly talk about the letter E, but for many of you, entrepreneurship might come up as the thing that's the right fit. For some of you, it's not. How do you know if a career is the right fit or not? That's what we're going to discuss today. Our guest, Bill Gurley, is a prominent and well-respected venture capitalist. As a general partner at Benchmark Capital, he made early investments in companies like Uber, Zillow, Stitch Fix, Grub Hub, Open Table, Nextdoor, and many, many more. He was named VC of the Year by TechCrunch in 2016 He was on Uber's Board of Directors until 2017, and there was even an actor who played him on a TV show on Showtime called Super Pumped. An actor named Kyle Chandler played a fictionalized version of our guest today, Bill Gurley. He is also consistently listed on the Forbes Midas list. He shares his story about how he got to the career that he's been in. He started off as a design engineer working at Compaq. Later, he worked on Wall Street as a research analyst. So he shares the story of finding work that was a great fit for him, and shares advice on how the rest of us can do the same. Here he is, Bill Gurley.

Hi, Bill.

Bill Gurley (2:18)

Hey, how are you? Thanks for having me on.

Paula Pant (2:20)

Oh, thank you for joining us.

Bill Gurley (2:21)

Yes.

Paula Pant (2:22)

You write a lot about how to discover a career that you love.

Bill Gurley (2:25)

Yeah.

Paula Pant (2:26)

For the average person who is listening to this, who is thinking, I don't know what I love, and I'm in my 50s, is this possible for me, given that I don't have a clear picture and given that I have a limited time horizon?

Bill Gurley (2:41)

Yeah. I do think it's possible. I mean, some of that's going to be heavily determinate on financial flexibility, which I know you talked to your audience about a lot. But if you're spending right up against every last cent that you have, your ability to shift might be limited. One piece of advice I would give to anybody, not just someone in their 50s, but probably more even importantly to someone who's just coming out of college, if you want to maximize optionality to be able to explore and do things and shift gears and change lanes, which I think those are things you absolutely want to be able to do. You can't get stuck financially, so you got to be careful about your spending especially early on.

Paula Pant (3:24)

Right.

Bill Gurley (3:25)

But I think it's possible. Yeah. In fact, Daniel Pink has a great book about regrets. One thing he highlights and he studied this across multiple geographies, multiple different ethnicities.

The number one regret people have at the end of their life is a regret of inaction. Right. He calls them boldness regrets. We're very good at forgiving ourselves for the things we did wrong. Like humans are very quick to move past, lesson learned. You know, don't dwell on it. There's not a lot of rumination on the mistakes made. But the thing we never tried eats at us. And he has a study where it actually grows in your head over time. So, that might be a kind of bat signal for the people that are 50 and know there's this thing they didn't try yet that's really nagging at them. Go for it.

Paula Pant (4:15)

Well, let's go through some of the principles one by one, beginning with the passion hypothesis, because you make the argument that it isn't really about following your quote unquote passion. That's sort of an overloaded word. It is really more about following your fascination, which is synonymous with your curiosity.