What Makes a Great Entrepreneur? | Ben Horowitz on Vintage x Vintage

Ben Horowitz (0:00)

I think it's midnight, and my phone rings. Unknown caller, so I'm like, oh, it's Kanye. I go, yeah, what's up? And he goes, hey Ben, I heard you're having a barbecue tomorrow. And I was like, yeah, yeah, I am. I want to record in your studio. And I'm like, yeah, I don't have a studio. Are their strengths world class, or are they the best in the world at something? And then you overlook everything else. That's what makes a company great, and that's what makes an entrepreneur great. Not, oh, they don't know how to do this, or, wow, they know nothing about finance. There's so many things that are wrong with every entrepreneur. Every great entrepreneur has got something, like, horribly wrong with them, but that's okay.

You know, it's what are they truly great at what they're great at?

SPEAKER_2 (0:43)

What separates a great entrepreneur from everyone else? For Ben Horowitz, it isn't the absence of weaknesses. It's having a strength so exceptional that everything else becomes secondary.

Today's episode comes from our Recommended Listening Series, where we feature standout conversations from people across our broader network. This one comes from Vintage x Vintage, where host James Norman sits down with a16z co-founder Ben Horowitz for the show's inaugural episode. Ben shares what he learned going from engineer to first-time CEO, how those experiences shake the founding of a16z, and why evaluating founders means looking for world-class strengths rather than trying to find someone who checks every box.

They also get into AI and why Ben sees this moment as bigger than the internet. As the constant difficulty of building software collapses, creativity becomes increasingly important, opening the door for people with deep knowledge of a problem to turn that knowledge into a product. And throughout the conversation, James and Ben return to a shared influence, hip hop, from the lessons Ben took from Nas at his lowest point, to why he created Paid in Full to recognize the pioneers who shaped the culture.

James Norman (1:56)

Welcome to the first episode of Vintage x Vintage.

Ben Horowitz (1:59)

This is the first one?

James Norman (2:00)

The first one.

Ben Horowitz (2:01)

All right. Well, that's good. We're getting off with a bang.

James Norman (2:03)

Right. You know, step into the game. But to start the conversation, is Vintage x Vintage, you are of a certain vintage of entrepreneur.

But we also have a certain vintage of wine as well. So like, and all the wines are connected to like the relationships. This is a continuum, right? But it's actually like Mondavi. So Robert Mondavi, you know, they kind of set the tone for American wine. But by 93, though, there was like this like virus vineyard situation in Napa. Yeah. So they had to go public. Under duress, like, oh, we got to get this money, we got to keep going.

Ben Horowitz (2:33)

Yeah.

James Norman (2:34)

Didn't turn out that well, because Wall Street directors came in and like abused the name. And now you have the Robert Mondavi wine that people would know today. But it kind of fell apart by 04, and the family had to pick up the pieces. But the youngest son came along and decided to make continuum. And he wanted to shoot for the stars, take all the learnings he had, and their workings on how to make great wine and make this. And so this was born out of struggle. And similar to my guest today, did the same in Silicon Valley, set the tone for cloud computing, had to sell the heart of the company to keep the thing going. Even had to go in public, stock dropped as a result, and had to crawl out of that. But took the knowledge one had in the team, and the inner workings of how the thing was managed, Opsware, and clawed your way back from people's like, they're counting them out. Nah, they're not going to make it. It's a dot-com boom bust. But it's like got the $1.65 billion exit. And so continuum is special and legendary, my guest, special and legendary. But it's great because of the struggle. And so this is the hard thing about hard things in the bottle.

And this is my guest Ben Horowitz.

Ben Horowitz (3:38)

All right. That's a very nice introduction. Thank you, Ali.

First of all, I call you James.

James Norman (3:43)

Most people know you as James.

Ben Horowitz (3:45)

I'm talking from the new me days.

SPEAKER_2 (3:47)

Right.

James Norman (3:47)

So, and actually, hold up, actually take a look at the year in the wine before that.

Ben Horowitz (3:52)

2017

James Norman (3:53)