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

I think it was midnight and my phone rings. Unknown caller, so I'm like, "Oh, it's Kanye."

[laughs]

I go, "Ye-Ye, 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 wanna record in your studio." And I'm like, "Ye, I, 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-

Mm-hmm

... with them, but that's okay.

Okay.

Uh, you know, you- it's, it's what are they truly great at what they're great at?

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 and 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 shaped 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 cost and 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.

Welcome to, uh, the first episode of Vintage and Vintage.

This is the first one?

It's the first one.

All right. Well, that's good.

Yeah.

We're getting off with a bang.

Right. You know, stepping into the game. Um, but to start the conversation, it is Vintage and Vintage. You are of a certain vintage of entrepreneur.

Yeah, yeah.

We also have a certain vintage-

An old vintage.

[laughs] We have a certain vintage of wine as well.

Yeah.

So like... And all the wines are connected to, like, the relationships. This is Continuum, right? But it's actually, like, Mondavi. So Robert Mondavi, you know, they kinda set the tone for American wine. But by '93, though, there was, like, this, like, virus vineyard situation in Napa.

Yeah.

And so they had to go public-

Oh

... under, under duress. Like-

Yeah

... "Oh, we gotta get this money. We gotta keep going."

Yeah.

Um, didn't turn out that well 'cause Wall Street directors came in and, like, abused the name, and now you have-

[laughs]

... the Robert Mondavi wine that people would know today, but-

Yeah

... it kinda fell apart by '04, and the family had to pick up the pieces. But the youngest, the youngest son came