Gurley reports three of his last six investments have female founders, highlighting Katrina Lake's founder-to-public-CEO trajectory.
“Three of the last six investments that I've made have female founders. Katrina's, obviously, as John pointed out, an amazing role model in terms of not only being a founder, but being a founder that made the transition to CEO and then being a founder that made a transition to CEO to public CEO.”
Gurley sits on four boards where women are founders: Nextdoor, Marco Polo, Katrina, and Solve Health.
“I sit on four boards where the women are founders. Nextdoor Marco Polo, Katrina, and Heather with with Solve Health, you know.”
Gurley argues founders who stay private longer are shirking their duty to maximize shareholder value.
“But that's the behavior of some of the founders in Silicon Valley that buy into the state private thing. Like the minute you started giving stock to your employees, you're in the game”
Gurley cites 58% disengagement and 15% quiet quitting data, contrasts with founders' constant learning requirements.
“15 of those 58 say they're quiet quitting. These are horrible numbers. Founders live on the edge of a new technological shift constantly, and they can't not know what's happening next.”
Gurley argues founders must constantly study new technology at a level uncommon in most other industries.
“Founders live on the edge of a new technological shift constantly, and they can't not know what's happening next. It requires a level of studying that is foreign in other industries and other fields.”
Gurley quotes Bezos saying he only invests when founders will pursue their vision regardless of funding.
“I only look for one thing. I want to know that this person's gonna go do this thing come hell or high water, whether I invest or not.”
Gurley says Bezos looks for unbridled determinism in founders who will execute regardless of investor involvement.
“I only look for one thing, which is that this person's going to go do this thing.”
Gurley quotes Josh Wolf's saying that chips on shoulders put chips in pockets.
“Josh Wolf of Lux Capital has a saying chips on shoulders put chips in pockets.”
Gurley says Adam Neumann's salesmanship in WeWork Series A was unlike anything he had ever seen.
“I remember where I was when he presented to us. Now keep in mind, Benchmark's never done a real estate transaction in the history of the firm.”
Gurley emphasizes the person matters more than the concept, citing founders who pivoted 180 degrees.
“And we've seen incredible businesses be built by great founders who have pivoted a 180 degrees from the original idea.”
Gurley recalls Travis Kalanick's first two companies ending in bankruptcy or minimal returns before Uber.
“I remember when we did the first Uber investment, Travis, his his first couple of companies, one of them I think ended up in bankruptcy.”
Gurley says Bezos only looks for one thing in founders: determinism that they'll succeed regardless of his involvement.
“Because it's not like he's got a lot of free time. He said, I only look for one thing, the determinism of the founder.”
Gurley asked Bezos how he made successful angel investments while running Amazon, learning his one criterion.
“have that? I'll give you a few. And the first one I borrowed from Jeff Bezos.”
Gurley quotes Bezos saying he only looks for determinism in founders who will succeed regardless of investment.
“He said, I wanna believe this person's gonna go do this, come hell or high water, whether I get involved or not, nothing's gonna stop him. And that's the trade he's looking for.”
Gurley argues venture capital bends toward youth because founders are young and young VCs understand new techniques better.
“I think it's very hard to be a venture capitalist as you get older and I think it's very easy to break into venture capital as a young person.”
Gurley blames AI founder fear-mongering for data center projects being stopped and regulatory impacts.
“That starts- Some of the founders. Yeah. And it's starting to have ramifications for the industry. A number of data center projects has been stopped.”
Gurley cites Brett Taylor as example of founder who repots himself across technology waves from maps to social to AI.
“He's just always right there as the thing changes and on top of the next thing.”
Gurley quotes Bezos saying he only asks if entrepreneurs will do this no matter what.
“when I meet an entrepreneur, there's only one thing I ask myself. Is this person gonna do this no matter what?”
Gurley says venture capitalists who see successful pivots learn it's all about the founder.
“And for any venture capitalist that's been through one of those pivots, they're famously known as pivots now, it's all about the person. Like, it's all about the founder.”
Gurley says founders are the chief salesperson for their company, selling to investors, employees, and customers constantly.
“But if you're a founder, you're selling to new investors, you're selling to employees, you own the company culture and the perception of the company, you're striking deals, you're selling to customers, you're just out selling all you're the number one sale you're the chief salesperson for your company,”
Gurley cites that new CEO hires are a fifty-fifty bet at best, questioning why investors would take that risk.
“I'm sure it's not scientific, but as new CEO hires a fifty fifty bet at best.”
Gurley argues founders are constantly selling to investors, employees, customers, and in deals.
“if you're a founder, you're selling to new investors, you're selling to employees, you own the company culture and the perception of the company, you're striking deals, you're selling to customers, you're just out selling all”
Gurley notes B2B companies have much higher founder replacement success rates than consumer companies.
“companies that serve businesses have a much higher success rate of replacing the founder than companies that serve consumers.”