Bill Gurley: 6 Out of 10 People Are Making This Mistake

My First Million

March 9, 2026

Run your life like a $100M business. Get Sam's system here: https://clickhubspot.com/fhs Episode 803: Sam Parr ( https://x.com/theSamParr ) sits down with legendary investor Bill Gurley ( https://x.com/bgurley ) about how to avoid the biggest mistake you can make in life.
Speakers: Bill Gurley, Sam Parr
**Bill Gurley** (0:00)
If you're crafting your own personal career and you're high agency, AI is like a jet pack. We've taught children, young adults how to grind. We've taught them to persevere for the sake of perseverance. And if you're stuck, you're stuck.

**Sam Parr** (0:13)
In order to do these exercises of finding your passion, you have to be like a ruthless asshole, you think?

**Bill Gurley** (0:19)
Unless you're trying to find that edge, somebody else may be.

**Sam Parr** (0:22)
You have to understand the difference between risk and uncertainty.

**Bill Gurley** (0:26)
People most at threat by AI are the ones that aren't continuously learning, that are just doing the same thing they did 10 years ago.

**Sam Parr** (0:33)
How many times when you were doing it did you want to quit?

**Bill Gurley** (0:35)
I don't ever remember wanting to quit.

**Sam Parr** (0:37)
Really?

**Bill Gurley** (0:37)
Really.

**Sam Parr** (0:38)
What did The Voice say when it was like, I found my calling? I want to talk about the book because there's a bunch of crazy stats in the book. I want to talk about the Nobel Laureate thing. That was interesting. But one of the craziest things early in the book, I think, did you run this survey and it said that six or seven out of 10 people hate their job?

**Bill Gurley** (1:06)
Yes. I had a co-writer, co-researcher on the book and we spent a ton of time together on Zoom calls and someone encouraged us to dive into a bunch of academic literature. We came across this Gallup poll that said that 53% of people aren't engaged at work. And so we had this idea to ask like a thousand people, if you could start your career over again, would you do it differently? And seven out of 10 said yes. And then we took that to Wharton People Analytics to do the official academic version. So you make sure you get all the statistical data correct. And their number came back six out of 10 So still a really big number.
There's a great book by Daniel Pink called The Power of Regrets. And he has a somewhat similar survey data of longitudinal through people's lives. And as you get older, your regrets of inaction start to really weigh on you and ruminate in your brain. And a regret of inaction is actively not doing something versus a regret of action is I made a mistake. And humans are really good at allowing themselves to make a mistake, but the path I never traveled, the door I never opened is heavier in their mind. And the survey might have been getting at that, like people thinking, wow, what if I had done something differently?

**Sam Parr** (2:29)
Well, the reason I was asking is like, I kind of want this whole like, I'm kind of obsessed with this idea of finding your passion, not just because of your book, but like one of my favorite books is Mastery by Robert Greene. Yes, it was changed my life. That changed my life. But the reason I'm interested in it is because like, I previously had a company that I sold and it was like very successful and all the traditional measurements. I have a company now that's quite successful and I like what I do. But in the back of my mind, I think that it's normal. Maybe you could tell me if I'm wrong, that like even grownups like who are successful still are like, am I following like the right path? Like am I following, am I going to be in that six out of 10 or the four out of 10? Do you find that like even when you were, when you left Compact and then eventually got into VC, which I imagine that would be your calling, that you still questioned it?

**Bill Gurley** (3:19)
After the engineering degree, I went to Wall Street for three years. So I-

**Sam Parr** (3:23)
You were like in research?

**Bill Gurley** (3:25)
I was in a sell-side research challenge, yeah. So I had two stops before I made it to venture.
In both cases, I had a moment of reflection, and it's more clear to me now than it was then, but where I ask, do I see myself doing this 30 years from now? And in many businesses, there's a lifer in the room that's done it their whole life, and that sounds a little judgmental. I don't mean it to be, but it gives you a way to reflect on whether that's the place you want to be in because they did it. And in both cases, after about two or three years, I got to a no even though I was doing well in those jobs, but thinking, do I want to be still be doing this 30 years from now was clarifying for me.

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