Ben Horowitz On What Makes a Great Founder

**Ben Horowitz** (0:00)
I think really good companies, the very, very, very best companies tend to have founders and CEOs who ask pretty aggressive questions. Zuckerberg, Larry Page, those guys who have kind of gotten all the way to the mountaintop, they're pretty blunt. If you're running away from the truth to preserve feelings, that's a very dangerous thing in a tech company. And the kind of corollary to that is, it's really important that like bad news travels fast, that if something's wrong, that as CEO you find out about it. And so you need that bluntness.

**Brian Halligan** (0:51)
Hey, everybody. Today's guest is Ben Horowitz of A16z fame. Few reasons I wanted to have him on. First, I wanted to get the behind the scenes look on why Andreessen passed on HubSpot back in the day. And there's a funny story behind that. He's seen so much. He's backed some amazing CEOs, and some CEOs that went down in dust.
Like, what do they have in common? What are the great ones? What do they do? What do they like? What's the patterns there? And the same with the ones who failed. I read his book like 100 years ago when I was running HubSpot. I thought it was really good. I think he published it in 2014 I wanted the updated, you know, what's changed since he wrote the hard thing about hard things back in the day. The convo I think is really good. One of the things I've always liked about Ben is he is completely unfiltered and gets after it. I think there's a lot of nuggets in here. I'll come back at the end and give you my summary. You probably don't remember when we first met. Can I remind you? Can I tell you about it? It's stuck in my mind. Kind of a long story. HubSpot pitched you on the Series D.

**Ben Horowitz** (1:56)
Okay, I remember that.

**Brian Halligan** (1:58)
Three of us came in for the pitch. Our very newly hired COO, JD Sherman, myself and my co-founder, Darmesh, and we walked in the room. We had a nice welcome because there's a guy that worked for you that was your sales guy named Mark Cranny, that was a former colleague of mine. And we had just written a book called Inbound Marketing, and two of your marketers had the book, so we were like, this is a hometown. We got this. Okay, we sat down, and JD sat here, and I sat here, and Darmesh sat here. I remember it like it was yesterday. And we started with intros. JD barely got a sentence out of his face, like, wait, you're the COO? Tell me about your background. You spent like 15 minutes on JD. You spent like 15 minutes on JD, and then it went to me. And then it's about 15 minutes on me, like, you're such an uncle, why did you hire a COO? And then Darmesh. Anyway, you guys passed, as did everyone. Two weeks later, I read your book. And I saw in the book that you're not a fan of the idea of hiring a COO. So I guess my question, and by the way, I think chips on the shoulder are really valuable. You put a chip, a ginormous chip on JD Sherman's shoulder.

**Ben Horowitz** (2:59)
Oh, good.

**Brian Halligan** (3:00)
It was incredibly beneficial. How do you feel about CEOs these days? Same thing or change your mind?

**Ben Horowitz** (3:06)
Well, no, I mean, I think that generally when a company is small, flatter is better. In the early 2000s, it was a very popular construct and it was kind of Mr. Outside, Mr. Inside, that kind of thing. If you're really scaling and you're not kind of wrestling with product market fit, like it can work for a time on a product cycle. But when you hit the end of the product cycle, it's so much about a company, a tech company is kind of the communication architecture. And it just makes that worse generally. It's a little like two people in charge. Not to say it can't work and it depends on the definition of COO. And if COO is really just a big title for the sales guy, that's fine. COO in the sense that I'm running the company and you're like Mr. Thought Man Outside, I think that's a great thing for a startup.

**Brian Halligan** (3:58)
You've invested in tons of CEOs at this point, coached tons. What are you looking for? What's a major green flag, red flag? How's it changed over time? What's your filter?

**Ben Horowitz** (4:09)
On a CEO?

**Brian Halligan** (4:10)
Founder CEO. So you're looking at the company and the market, but the person, not the co-founder, the CEO.