E141: State of Series A's, VC dry powder, IPO window opens + more with Bill Gurley & Brad Gerstner

**David Friedberg** (0:00)
I'm recording, yeah.
How's my hair, Nick? Do I look ridiculous? I shouldn't have worn a hat. Oh my God, I went to the teaching salon in for a haircut a few days ago.

**Jason Calacanis** (0:09)
The teaching salon.

**David Friedberg** (0:11)
$10.

**Jason Calacanis** (0:12)
You got $10 worth of value.

**David Friedberg** (0:13)
My neck was literally bleeding. He's diagonal on the back.
And he was stoned the whole time I walk in. He's like, what do you want? I'm like, I booked this thing. He's like, shit, OK, sit down. I thought I was in a barber shop, candid camera thing.

**Jason Calacanis** (0:33)
Why would you possibly do that?

**David Friedberg** (0:35)
There was nothing available. I told my wife, I'm like, get me any hair appointment, anything. I just got to get my haircut. It was so long. And then she's like, oh, I got you an appointment at the fucking teaching school. Oh, I'm like, that's high end.
All the hair salon stylists go there. It must be awesome.
This guy fucking butchered me.

**Jason Calacanis** (0:49)
Guy's worth over $100 million. He got a $10 haircut.

**David Friedberg** (0:52)
Fucking $10. And then he's like, what would you like to tip?

**Chamath Palihapitiya** (0:55)
I'm like, here's a tip.

**David Friedberg** (0:56)
You shouldn't be a fucking barber. Get a new career.

**Jason Calacanis** (1:18)
Welcome back to The All-In Podcast, episode 141 Chamath Palihapitiya has gone missing somewhere in the Mediterranean. We've sent some search crews out.
We got some beacons. We're trying to find him, but he is not here today. There will be no conspicuous consumption or discussion of truffle season or wine.
But instead, we went to the BG Squared, if you got to come to All-In Summit 2022 One of the highlights of the event was having two BGs, Brad Gerstner and Bill Gurley on the pod. So we thought for all-star summer, we would bring in some all-stars here. Welcome back to the pod, 5th bestie, Brad Gerstner and Bill Gurley. How are you, sir?

**Bill Gurley** (2:00)
I'm doing great. Thanks for having me on.

**Jason Calacanis** (2:02)
Bill, you don't do a lot of press. You don't do a lot of pods.
And I know you're on a lot of boards, but you're not part of Benchmark's Next Fund. So people are wondering, are you retiring? What are you up to? I know you're still got all these boards you're on, but what's Bill Gurley up to these days?

**Bill Gurley** (2:19)
Yeah, I appreciate that. As you mentioned, I'm on nine Benchmark boards still. So I'm working with those and doing the classic work that I've been doing my whole career.
Second thing is I've started, I've done a handful of angel deals, about one 100th the frequency of J-Cow here, but a few. So dipping my toe in the water. And then third, I've been working hard on a book. I've got a co-writer, we've been doing a ton of research. We've got a proposal ready to go and an agent, and we're going to go out to publisher soon.

**Jason Calacanis** (2:54)
Oh, well, you should just do Harper Business. I'll put you in touch with Hollis. That's the winning publisher. That's the best business publisher in the world.

**Bill Gurley** (3:01)
Perfect.

**Jason Calacanis** (3:02)
No, Harper Collins Business, the world's greatest publisher.

**David Sacks** (3:07)
Bill, can you tell us what the thesis is?

**Bill Gurley** (3:11)
Yeah, it's a further development of a speech I gave at University of Texas Business School about how to chase and succeed in your dream job.

**Jason Calacanis** (3:23)
Oh, so like career advice, letter to a younger Gurley. Is that what this is? A letter to a younger Bill Gurley?

**Bill Gurley** (3:28)
I didn't want to do like, oh, here's my thoughts on venture capital that didn't feel right. This is something I'm more passionate about. Something I hope will be impactful to a lot of people. I've already gotten quite a bit of feedback from people that have been moved by the shorter version on the presentation.

**Jason Calacanis** (3:46)
Well, when you look back on your career, unpack it for a minute. What do you think the things you got right were or the things you might change in terms of your career and being happy and finding your passion?

**Bill Gurley** (3:59)
Yeah, I do feel super fortunate that I was able to do my dream job for over two decades. And I love innovation. I love betting and gambling. And I love the combination of being able to think through markets and disruptions and to be able to place bets and all those things are super exciting.