BONUS: Bill Gurley on Investing Early in Tech Disruptors & 'Runnin' Down a Dream'

SPEAKER_1 (0:02)

Bloomberg Audio Studios, Podcasts, Radio, News. This is Masters in Business with Barry Ritholtz on Bloomberg Radio.

Barry Ritholtz (0:16)

This week on the podcast, what can I say? Another banger, Bill Gurley of Benchmark Capital, legendary VC, early investor in Uber, Zillow, OpenTable, Grubhub, Nextdoor, The List, Instagram, just Twitter. The list just goes on and on and on. What a fascinating career filled with insights, not only about venture investing, but about building a career that you love. I thought this conversation was fascinating, and I think you will also, with no further ado, my conversation with Benchmark's Bill Gurley.

Before we get into the book, which I found very interesting in your whole career, let's start with your background. You get a Bachelors in Computer Science from the University of Florida, and then an MBA from UT Austin. What was the original career plan?

Bill Gurley (1:12)

So I fell in love with computers at a young age, and many people that get to Silicon Valley, you hear that common refrain. I had a Commodore VIC-20 that would plug in to your television, and it didn't have solid state memory, so you'd type programs in, but when you turned it off, they were gone. You had to start over. Anyway, I fell in love with programming, as many people do, and just amazed that you could create things, you know? And so that was my undergrad degree. I worked for two years in change at Compact Computer Corporation using those skills, and discovered that that wasn't going to be my long-term path.

Barry Ritholtz (1:53)

You said you were exceedingly bored at what looked like on paper a dream job.

Bill Gurley (1:58)

Yeah.

Barry Ritholtz (1:59)

Explain.

Bill Gurley (2:02)

Well, back then, Compact was a leader in the personal computer business, and we would release one PC, and then, usually around an Intel generation, you would reach the next PC.

Barry Ritholtz (2:15)

See, kids today don't remember 38646, NTM. It was like a big deal.

Bill Gurley (2:21)

Yeah. And so we started on the third project that was a lot like the second and a lot like the first. And I asked myself a question, and I don't know if I realized I was doing it as much then as I do now.

I asked myself the question, is this what I want to be doing 30 years from now? And in any organization, there's someone that's a lifer that you can ask yourself, is that what I want? And so with no judgment towards people that do that. But it became very clear that that wasn't for me. And this will be particularly interesting for your audience because it's an investment crowd. At home at night, I had read one up on Wall Street by Peter Lynch. And I had opened a Prodigy account, which was this precursor to AOL. And I was starting to get really interested in stocks. I had bought the value line. You remember this thing?

Barry Ritholtz (3:15)

Oh, sure.

Bill Gurley (3:15)

It became a big notebook with the one pagers.

Barry Ritholtz (3:17)

You get these updates and the three ring binders. And like a whole shelf of them alphabetical.

Bill Gurley (3:23)

And one thing I'd really encourage people to think about is, what are you doing in your free time? And maybe you should, is there a clue that that should actually be what you do full time? And so this thing was itching at me.

Barry Ritholtz (3:36)

So, first gig in finance was at Deutsche Bank?

Bill Gurley (3:39)

No, it was Credit Suisse First Boston. So, while I was at the University of Texas MBA program, I thought about venture, but it seemed very hard to get towards. I like technology, I like disruption, I like programming. And it seemed hard to get at. But at that time, when you get to business school, some young adults like to pretend they're financiers, and so they read Fortune, Forbes, the Wall Street Journal, and the Atrium, you know, as if. And I would read the tech articles, and there was a team at Goldman Sachs on the sell side. And the sell side, I think, was more kind of held in higher regards back in those days. And this team with Dan Benton and Rick Sherlin at Goldman got quoted all the time, and I said to myself, you know, I really love my corporate strategy class, I love technology, these people get to opine on it and are treated as experts. So I went to, I came here to New York, I knocked on doors cold, I asked that particular team for a meeting, they let me in. I'm a freshman, our first year at the University of Texas, they let me in. And I told all the other research directors, I'll be in town meeting with those guys. And I got like 10 meetings doing that. And one of those individuals was Al Jackson, and he gave me a shot. And I can remember the first day of orientation, there were like 40 new people from MBA programs, and we had to go around and say our name in school. And it was what you'd expect, Columbia, Wharton, Harvard, but I was at the University of Tad, I was the outlier.