Ben Horowitz Interview Transcript — What Makes a Great Founder

Guest: Ben Horowitz — Co-founder and General Partner, Andreessen Horowitz (a16z) Host: Brian Halligan — Co-founder and former CEO, HubSpot Channel: Sequoia Capital Duration: 49 minutes Source: YouTube Analysis: Deep Analysis & Commentary

Table of Contents

1. Opening: Why a16z Passed on HubSpot 00:00:00
2. Does the COO Role Still Make Sense? 00:02:51
3. Filtering for Great CEOs: Independent Thinking & Leadership 00:03:57
4. The Most Common Founder Mistakes: Confidence & Decision Debt 00:08:31
5. How to Hire Executives — Especially a Head of Sales 00:11:48
6. The PTC Sales Machine: Why Hard Products Build Better Sellers 00:19:08
7. HubSpot’s Sales Interview: The 12-Minute Sell Test 00:24:58
8. Bluntness in Culture & Constructive Confrontation 00:26:23
9. The Truth About Founder Mode 00:30:15
10. What CEOs Can Learn from Zuckerberg 00:35:02
11. Culture Is Behaviors, Not Values 00:36:38
12. The CEO’s Journey Through Uncertainty 00:42:55

1. Opening: Why a16z Passed on HubSpot

Time: 00:00:00 - 00:02:51

Ben: I think really good companies — the very, very best companies — tend to have founders and CEOs who ask pretty aggressive questions. Zuckerberg, Larry Page, those guys who have 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 corollary to that is it’s really important that bad news travels fast — that if something’s wrong, as CEO, you find out about it. And so you need that bluntness.

Brian: 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. What do they have in common? What are the great ones? What do they do? What’s the patterns there? And same with the ones who failed.

I read his book a hundred years ago when I was running HubSpot. I thought it was really good — I think he published it in 2014. I wanted the updated version. 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 tell you about it? It’s stuck in my mind. Kind of a long story. HubSpot pitched you on the Series D.

Ben: Okay, I remember that.

Brian: Yeah. Three of us came in for the pitch — our very newly hired COO, J.D. Sherman, myself, and my co-founder Dharmesh. We walked in the room, we had a nice welcome because there was a guy that worked for you, your sales guy Mark Cranny, who was a former colleague of mine. And then 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.

We sat down — J.D. sat here, I sat here, and Dharmesh sat here. I remember it like it was yesterday. We started with intros. J.D. barely got a sentence out and you were like, “Wait, you’re the COO? Tell me about your background.” You spent about 15 minutes on J.D. and then went to me — about 15 minutes — like, “You’re such a knucklehead, why’d you hire a COO?” And then Dharmesh. 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 hiring a COO.

Ben: By the way, I think chips on the shoulder are really valuable. You put a ginormous chip on J.D. Sherman’s shoulder. It was incredibly beneficial.

2. Does the COO Role Still Make Sense?

Time: 00:02:51 - 00:03:57

Brian: How do you feel about COOs these days? Same thing or change your mind?

Ben: I think generally when a company is small, flatter is better. In the early 2000s it was a very popular construction — the “Mr. Outside, Mr. Inside” kind of thing. If you’re really scaling and not wrestling with product-market fit, it can work for a time on a product cycle. But when you hit the end of the product cycle — so much about a tech company is 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. It depends on the definition of COO. 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 Mr. Thought Man outside” — I think that’s not a great thing for a startup.

3. Filtering for Great CEOs: Independent Thinking & Leadership

Time: 00:03:57 - 00:08:31

Brian: You’ve invested in tons of CEOs at this point. What are you looking for? Major green flag, red flag? What’s your filter on a CEO — a founder CEO?

Ben: The thing about founder CEOs is that there’s definitely not a canonical one. Look at Mark Zuckerberg and Ali Gozi and Elon Musk — they’re all extremely different types of people. So you try not to get into anything about the look and feel or sound — are they extroverted, introverted — none of that matters.

There’s a few things in common. One, anybody great really thinks for themselves. They don’t feel like they’re reading the room or influenced by what I’m going to say. You can probably figure that out during the pitch. Then — do they have truly original thinking? And from a leadership standpoint, I really like the Colin Powell definition: leadership is the ability to get people to follow you, if only out of curiosity. I think, would I want to work for this person? How interesting are they? If you don’t have that right, you’re not going to bring in the super high-end talent. It’s a momentum thing — if you can’t hire the very top talent, you’re very unlikely to be a great company. It’s about talent density.

Brian: We just had our Sequoia offsite and I got into a discussion with Sean McGuire, one of our partners. Very outspoken. He said what we should be looking for are founders who won the Chess Olympiad or the Math Olympiad in high school, surrounded by those folks. He made a good point. A lot of people nodded.

I thought about it and I was like, HubSpot’s no Tesla, but it did pretty well. My co-founder and I, we’re Sloan people. We hired tons of people from Northeastern. It worked out pretty well. And companies like Salesforce and ServiceNow look like us. Do you have a take on my disagreement with Sean?

Ben: I think it depends on the era and the market. HubSpot was a marketing and sales idea as much as a technological idea. You have to have great people on that side who tend not to be Math Olympiad winners. For that company, I don’t think Sean’s right. For other companies, he is.

The other thing is, “Math Olympiad” is very specific. The very best companies are founded by exceptionally smart people — there’s no question about that. I agree with him on that angle. How smart is Elon? Extremely smart. Was he Math Olympiad? Probably not. But raw horsepower is pretty important. Larry Page is probably one of the smartest people in the world. That ends up mattering if you’re going to build something Google-sized.

The best CEO I personally work with right now is probably Ali Gozi at Databricks. PhD in computer science — extremely smart, meets the Sean McGuire test. But he’s also an exceptionally good go-to-market leader for an enterprise software CEO, able to compete with Snowflake, which was a very strong GTM organization. And he’s absolutely paranoid. The only person I’ve ever known as paranoid as Ali — I guess Elon is at this level — is Andy Grove. He wrote a book about it (Only the Paranoid Survive).

I think some of that comes from him being a refugee. He grew up in Iran and when Ayatollah Khomeini came in, he had to flee to Sweden. Having everything taken away from him really informed his psychology in a way that’s very beneficial for a founder.

4. The Most Common Founder Mistakes: Confidence & Decision Debt

Time: 00:08:31 - 00:11:48

Brian: I work with a lot of founders. Their companies are growing fast and they’re new to this. What’s the pattern of mistakes on the way up?

Ben: The universal one is confidence. It starts with the fact that nobody knows what they’re doing. You have an idea, you invent something. You know how to run a company? No idea. So you start building the company and you make a lot of mistakes. Those mistakes are extremely damaging. You feel terrible because you hired all the people, you sold them on this great idea, then you make a mistake and everybody gets hurt.

You see people react in two very dangerous ways. One is they overly defer. “I hired a lot of smart people, I’m going to be very open to their input on all the decisions” — to the point where you’re not really making the decision yourself. You’re doing a poll. But nobody other than the CEO has the context to make that decision. Nobody sees the whole picture. That leads to bad decisions and a very dangerous political environment where people go, “Oh, there’s a vacuum here. I can step into it.”

The second thing is hesitation. “I don’t know what the right answer is. I’m 52-48 on it, but I’m afraid of making mistakes, so I’m going to not decide.” Or the avoidance version — “I see something bad. I really need to fire the head of sales. But what is the press going to say? What is my board going to say?” You’re thinking about everything you should not be thinking about, rather than: can this person do the job?

Those things are really what cause founders to fail at the CEO job. That lack of confidence, that hesitation. I tell CEOs: if you were a linebacker in the NFL and you were really fast but you didn’t trust your eyes, you would get cut — you’d never get to the ball carrier in time. If you don’t trust your eyes as CEO and go run at the problem and make the decision, you’re going to fail.

Brian: It resonates with me. At HubSpot we had all kinds of debt — culture debt, product debt. We had decision debt.

Ben: Decision debt is the worst debt, by the way, because it paralyzes a company.

Brian: I had it. I fell into your trap. The way it worked was I’d see the company slowing down, a lot of debate, a lot of stuff on my desk. Then once every four, five, six months I’d be like, “I need to make some frigging decisions.” And once I made them, everything just started moving and flowing.

5. How to Hire Executives — Especially a Head of Sales

Time: 00:11:48 - 00:19:08

Brian: Talk about team building mistakes. You’ve seen a lot of VP of Sales hires go wrong.

Ben: More than anything else. Hiring executives is something you don’t know how to do. A lot of times you don’t even know what the job is. What is a CFO? What’s a control structure? People go in to hire them with that level of knowledge and think they can smell it out from talking to a person. It’s like trying to hire a Japanese interpreter and you don’t know Japanese — they’re all going to sound pretty good, and it’s going to be very hard for you to distinguish.

Preparation is very important. Have you spoken to enough CEOs? Have you asked them what’s the difference between a good CFO and a great CFO? How would you hire this person? What would you ask them? And if you have a chance, try to do the job yourself first — act in that role so you can get a feel for what the challenge is in your company. You don’t want a generic CFO, you want one for your business.

Then when you get into sales — the problem we have all the time is engineers running the company hiring a head of sales. You could not be more culturally different.

It goes right down to how they talk to you. If you ask an engineer a question, 100% of them will try to think of the correct answer. That’s how they think. If you’re a salesperson, your first thought isn’t “what’s the answer?” — it’s “why the fuck are you asking me that question?” Because that’s a clue.

If you ask an engineer, “Does your product have this feature?” — the answer is yes or no. If you ask a sales guy, they’re thinking, “What competitor was in here that planted that trap for me? What’s their weakness? How do I get to that?”

So if you have an engineer talking to a good sales leader, it’s going to upset them because the sales person often won’t answer the question directly — they’re trying to figure out why they’re being asked. The result is the guys who are good at the job get rejected because you don’t like them. And the people who are terrible at it are the ones that end up getting hired.

Mark Cranny used to say, “These CEOs just want to take a guy who failed the engineering test, put a clean shirt on him, and make him head of sales.” There’s a real truth to that.

Ben: I’ll never forget the Okta story. Both Sequoia and we were invested — I was on the board with Pat Grady. The very first big mistake that Todd almost made was hiring the head of sales. Two candidates. One I forgot his name, and the other was Adam Aarons, a PTC guy. We knew everything about Adam — he’d worked for Cranny, he’d worked for McMahon. I knew everybody in the tree and I called them all and they were like, “This is the guy.” The other guy’s references came back okay — not great.

But Todd wanted to hire the other guy because he was much more enthusiastic about Okta. Whereas Adam was like, “Well, I don’t know about this company. Let me talk to some of your customers.”

I said, “Todd, you don’t want the sales guy all enthusiastic. You want them to be qualifying you.” Good sales people don’t just answer questions — they qualify the customer. Do you really have the money? Do you really have the need? Do I really have a shot here?

And beyond that, I’ve got guys who owe me favors more than they owe Adam favors, telling me he’s great. The other guy’s references — people who owe him favors and don’t owe me anything — say he’s a B.

I said — and I don’t talk to founders like this anymore because I’m more mature — “Todd, look, if this hire doesn’t work, this is the end of your company. So you’ve got to be 100% confident. I’m telling you you’re wrong, and I have more experience at this than you.” I really put pressure on him. He hired Adam, and it ended up really making the company.

Brian: If we had hired the other guy, Okta would have gone bankrupt. So the takeaway for the engineer-CEO: one, blind references really matter. And two —

Ben: Who are you bringing with you? That’s what I always ask. Any great sales leader has a big set of followers. Anyone who’s not great? Nobody. Because the one thing sales people are — they’re savvy about the leader. I’ve never met even a mediocre salesperson who doesn’t know who’s a good leader.

6. The PTC Sales Machine: Why Hard Products Build Better Sellers

Time: 00:19:08 - 00:24:58

Brian: You brought up PTC. You’ve hired people from PTC. I came from PTC. First, who’s the equivalent of PTC now — building the sales leaders filling Silicon Valley? And what was it about the PTC mafia that worked so well?

For listeners: PTC was the fastest-growing company in the world in the ’90s. We sold CAD/CAM and PLM software to manufacturers. Hard sell, but we were very good at it. The diaspora of PTC sales execs throughout Silicon Valley is remarkable.

Ben: One of the underrated things about PTC was the product wasn’t that great — particularly the Windchill product. The loop didn’t work. But that’s the point — anybody can sell a great product. When you’re hiring, you like a sales person who had a hard sell. You don’t want somebody where anyone could have sold that product.

Brian: So if you see a VP from Databricks and you’re looking for a CRO for your startup — they’ve got brand, they’ve got mojo. Is that who you want for an early-stage startup?

Ben: It’s like the early days of Oracle — those guys were different than an Oracle salesperson today. As it gets more established, it’s harder to tell. But I will say: if you have a product that’s complicated to sell, that’s when you get to the PTC level.

The thing about PTC that was amazing — other than the culture and attitude, which was unique and probably illegal today, almost certainly illegal today — the thing that’s very replicable is the discipline. The discipline came down to: you’re going into an account, there are competitors. How systematic are you about laying traps for competitors? Making a comprehensive technical case, a comprehensive business case. Charting everybody in the organization who’s in the decision process — it was a very complicated decision process for PTC — and getting assurances they’re all lined up.

That’s so complicated and requires so much courage, effort, and competitiveness that it translates into anything. Whereas if you’re walking into an account and they’re already predisposed to buy, you can skip steps, get away with things. Right now with OpenAI and Anthropic, everybody wants to buy AI. They’re already predisposed to buy. Very different from “Who the hell are you? I never heard of PTC.”

Ben: Ron Gabrisco, who was the original head of sales at Databricks — we got him. I had never heard of his company, which was a public company. They were literally selling FTP. Secure FTP. Think about how good at selling you have to be to make your number as a public company selling that. This guy obviously had the discipline forced upon him, and he was extremely smart. That combination — I’ll take that all day.

The core question is: are you somebody who joined VMware when it was on fire and got a big position, but you ran the playbook that was set up for you? Or are you the person who wrote the playbook — who figured out how to sell a very complicated piece of software, how to lock out the competition, how to train and discipline the sales force? That’s a much harder find.

Brian: My takeaways from PTC — I was basically the first BDR there, spent ten years. A lot of it was contrarian to how people thought about selling. We sold an application one way, then moved into the platform business, totally changed how we sold. Very disciplined on both sides and very process-oriented. Really managed the process tightly. And very tight on the profile of the sales rep.

Ben: The profile — that’s what I always ask when I interview sales leaders: “What’s the profile of your rep?” It’s amazing to me that people in very senior, very big positions sometimes have very loose profiles. Whereas the ones who really have to compete — their profile is extremely tight. What they’re looking for is so specific and often surprising.

7. HubSpot’s Sales Interview: The 12-Minute Sell Test

Time: 00:24:58 - 00:26:23

Brian: Sticking on sales for a sec. One of the things we got right at HubSpot — got a lot wrong — but one thing we got right was the interview process. What we found was reps who are good learners did well inside HubSpot. So our profile was: people on their second sales job, not their fifth, not their first. Half-decent school — not Harvard, not MIT, state school, B average. Competitive athlete.

If they met those criteria, they came in for a half hour. “Ben, welcome.” I’d give you a scenario, I’d be the customer. “Sell me HubSpot” — and I’d give you 12 minutes. Literally timed it. Then I’d say, “That’s very good, Ben. Here’s my feedback.” Couple minutes of feedback. “Why don’t you think about it? Let’s do it again.”

If the person internalized that feedback and sold it better the second time, 99% of the time we hired them.

Ben: Oh, that’s interesting.

Brian: And it scaled really well.

Ben: Right. How good are they at listening? This is the other mistake people make — they look for somebody who’s good at talking. You really want somebody who’s good at listening. That’s an important subtle difference.

8. Bluntness in Culture & Constructive Confrontation

Time: 00:26:23 - 00:30:15

Brian: While we’re on this type of thing — you were the recipient of maybe my favorite email in the history of emails. May I read it to you?

The background: you had a big product launch coming, you were excited about it, and you had a press tour coming up. And Marc Andreessen front-ran it. You sent him an email: “I guess we’re not going to wait until the 5th to launch the product then.” And the response from Marc Andreessen to Ben Horowitz:

Apparently you don’t understand how serious the situation is. We’re getting killed, killed, killed out there. Our current product is radically worse than the competition. We had nothing to say for months. As a result, we’ve lost over $3 billion in market cap. We’re now in danger of losing the whole company. And it’s the server management’s fault. Next time, do the fucking interview yourself. Fuck off, Marc.

[Laughs]

Brian: Are we out of the “fuck off” era? From Mark, from PTC? Are we too soft now?

Ben: Elon’s not soft. I don’t think it’s quite at PTC level. In Cranny’s interview with McMahon, I think McMahon said, “What would you do if I hit you in the face right now?” And Cranny’s response was, “Well, first of all, you better knock me out.” Then McMahon says, “But what would you do?” He says, “Is this a question? Are you testing my intelligence or my courage?” Good answer.

That kind of thing — if you went and asked somebody that in an interview today… My first interview at PTC, I walked in with my suit on and Harrison, who was originally in sales, said, “I wouldn’t wear that suit to a shit fight.”

Ben: I think really good companies — the very best companies — tend to have founders and CEOs who ask pretty aggressive questions. Zuckerberg, Larry Page, those guys who have gotten all the way to the mountaintop, they’re pretty blunt.

I think that’s important because one of the most critical things in a company culturally is: one, you give direct feedback, and you can have it out. Marc was wrong on that feedback to me — I was right. But it’s important that he be able to say that, and then it’s important that I be able to stand up to it. Otherwise the truth doesn’t come out. If you’re running away from the truth to preserve feelings, that’s a very dangerous thing in a tech company. And the corollary is it’s really important that bad news travels fast.

Andy Grove used to call it “constructive confrontation.” One of my favorite Andy Grove anecdotes — somebody was late to a meeting. This is when Intel was a monster and Andy was God. They come in late and he looks at them and goes, “All I have in this life is time, and you’re fucking wasting it.”

Which is maybe the meanest thing you could ever say to somebody. But particularly as a company grows, you need to reset the culture. If it’s starting to fray at the edges, you can’t just let that go. By saying that, it might have crushed that person’s feelings, but everybody told that story to the point where I heard it — and I didn’t work at Intel. That’s a culture anchor: we’re not late to meetings here. That’s not what we do.

9. The Truth About Founder Mode

Time: 00:30:15 - 00:35:01

Brian: Speaking of that — Paul Graham wrote the Founder Mode memo. It strikes me as relatively standard operating procedure now. Is that your reaction too?

Ben: Yes, although there’s a part that’s wrong — or a little misleading. It came originally from Brian Chesky. His story is right: he hired extremely senior people, then overly deferred, which created fiefdoms, politics, all kinds of weird stuff. After COVID, he took the company back by going into “founder mode” — much more dictatorial. That part is all correct.

I think the danger is people are taking it to the point where they’re going, “Well, I don’t want to hire any senior people.” It’s like — okay, so you’re going to compete, and you need a worldwide sales organization, and you’re going to try and grow a person from scratch? Let me tell you all the things that person doesn’t know that they’re going to have to learn on your nickel that you could just buy today. What’s your profile? How do you split territories? How do you open up international? There’s years and years of experience and relationships required.

Because you’re in “founder mode,” you’re so afraid to hire? No. You need to be able to hire that person, but you need to be able to manage them. That’s very different from avoid, avoid, avoid.

I think people have taken what Paul wrote to mean “no experienced people.” Particularly for enterprise companies, that definitely doesn’t work. Even consumer companies — positions like CFO — outside knowledge is just valuable. You’ve got to learn enough about that job in founder mode that you feel confident managing that person and telling them what to do — not having them tell you what to do. That’s when you lose the company.

So I think it’s good. It’s an overcorrection from where things were.

Brian: One of my favorite CEOs is Jensen Huang — 60 direct reports, gives feedback in public. The interesting thing is, none of the CEOs I coach really do that. People also haven’t followed Elon’s playbook. Nobody uses “the algorithm” outside of Elon’s companies.

Ben: Most of the companies you recruit out of don’t run like that. So people don’t think of it that way. And to run it like Jensen does — you’ve got to have massive confidence. Every direct report has to be basically CEO-caliber autonomous. I’m not developing you — they either can do it or they can’t. I highly believe that CEOs can’t really develop executives.

Elon is the most competent and has the most confidence of anyone. Jensen is at that caliber. But a lot of people need to develop that as they go. When I observed Zuckerberg, he didn’t have that the whole way — he deferred half the company to Sheryl for a while until he could build his confidence. I think that’s the more normal path. It’s hard to go from zero to Jensen. Jensen’s been doing it for 30 years. What was he like four years in? I suspect he wasn’t quite at this “master of the universe” level.

10. What CEOs Can Learn from Zuckerberg

Time: 00:35:02 - 00:36:38

Brian: What can CEOs learn from Zuckerberg? You work with him pretty closely.

Ben: Zuck is very, very good at operating from first principles thinking — not being overly influenced by anybody else’s ideas or just the way things are. He’s very good at just looking at it. And they were amazingly disciplined at looking at things through a data lens — what does the data say, do that. That’s how they were able to grow so fast and overcome the competition. He definitely stays extremely curious, which I think all the great CEOs are — very interested in everything, all the time.

People underestimate him. And Elon and Jensen. They’re like, “Oh, those guys are nerds.” Their people skills are astoundingly good.

Brian: Do you think they always were? Zuckerberg struck me as that not being the case early.

Ben: He was so introverted that you couldn’t see it, but I felt like it was going on inside his head. If you look at the M&A deals he’s done, he’s a really outstanding psychologist. His mom is in that profession — she’s very smart about it. I think it was always in there, but he needed the confidence to get it out. He started that company when he was a little kid — 20 years old.

11. Culture Is Behaviors, Not Values

Time: 00:36:38 - 00:42:55

Brian: You wrote a whole book about culture. What are people getting wrong?

Ben: People don’t know what it is. That’s the main thing. That’s why I wrote the book. Although it’s funny — the people who really liked that book were like Ted Sarandos. I realized after I wrote it: you really don’t have the cultural issue until you get big. At the startup phase, you may be sowing the seeds of your own cultural problems, but there are no real cultural issues because the thing is small. You’re managing the culture by hand, unconsciously.

People think of culture as values. “We have a culture of integrity.” “We have each other’s backs.” All the same. Everyone’s got the same ones. Those things aren’t really anything — they’re just platitudes.

The actual thing is behaviors. When you think about your culture, you want to think about: what are the behaviors that put you in a place where you’re the kind of company that you want to be and give you the advantage that you want to have?

We’re in venture capital. What does everybody say? “We really love entrepreneurs.” But then you hear how entrepreneurs talk about a lot of VCs: “These guys are arrogant. They’re assholes. They talk down to me.” Well, if you want to be this, why are you that?

It gets down to behaviors. Are you on time for a pitch meeting? Are you on your phone during a pitch meeting? Do you get back to the entrepreneur if you’re not going to invest? These behaviors end up setting the culture — whether you actually care about entrepreneurs or you think you’re above them. It doesn’t have anything to do with what you said. It has to do with what you do. That’s why I called the book What You Do Is Who You Are.

But it takes a lot of thought. If you want “treat the company’s money like it’s your own” — great, but what does that mean? Where are you staying? What hotel? How are you traveling? That has to be systematic.

Brian: What about the brilliant 100x engineer who’s an asshole?

Ben: By the way, venture capital has more of those than engineering organizations. On an engineering team, you need to define the parameters. What does “asshole” mean? If it means that in code review you don’t say anything, then go in the middle of the night and rewrite their code — that’s going to be tricky as you grow. If it means you expect a super-high standard — that’s another thing.

You want to define: what is it that we’re not going to do here? The thing about engineers is they’re amazing at following rules. Make clear what the parameters are.

Mark and I talk about this sometimes — was Steve Jobs so mean to people because that just goes with being so brilliant? Or because he could get away with it because he was so brilliant?

Brian: I’ve had the same debate.

Ben: I think it’s a little more the latter. He didn’t have to do that, but he could because it was his company. The problem with founders modeling themselves after Jobs — or Elon — is that if you’re not Jobs or Elon, maybe you can’t get away with it. Maybe people just walk out the door in a way they wouldn’t with those guys.

It’s very hard to have the highest-performing talent without some of those behaviors. So you have to be very specific — “We’re not going to have this, but we’ll have that.”

One thing I’ve outlawed at the firm: you can’t make yourself look smart by making somebody else look dumb. That doesn’t count here. If you do it with an entrepreneur — if you get on Twitter and say, “Oh, that business sells dollars for 85 cents, ha ha ha, I’m so smart” — fuck you, you’re fired. I’m not dealing with that at all. Because that’s not who we’re going to be. We love that you’re smart. You can be as smart as you want. You don’t have to get there through that method.

Once people know that rule, they’re fine not doing it. But I couldn’t say “just don’t be an asshole” — that’s too vague. Sometimes the smartest people are going to be like, “I’m not going to suffer through this dumbass conversation.” You can’t require them to suffer through every dumb conversation. So it’s not a “no asshole rule” — it’s: what specifically is over the line and what’s not? Even very spiky people can live in that kind of context.

12. The CEO’s Journey Through Uncertainty

Time: 00:42:55 - 00:48:59

Brian: You brought this up in another pod that I wanted to follow up on. When I was CEO of HubSpot, I didn’t know what I was doing a lot of the time. I was confused a lot. And you felt the same way as CEO. What percentage of the time do you feel like “I really don’t know what I’m doing” versus “I’ve got a handle on this”?

Ben: Everybody pretends they know what they’re doing. That’s part of the challenge. It takes a while. I had to grow up very fast — we went public when we were 18 months old. That’ll grow you up in a hurry. But I didn’t really feel like I knew what I was doing until probably four years into it — when I rebuilt the sales force, brought in Cranny, all that kind of thing. And I was never as confident then as I am now.

It’s different for different people, but you need enough reps at it. The more confident you are in your judgment, the faster the decisions you can make. The less you care about what people think, the less you care about making a mistake. That’s why Jensen is so magical — he sits in the room, talks to everybody, knows exactly what he wants. Same with Elon. I guarantee you, neither of them started that way. You build into that.

Brian: I see silly things on Twitter where people say venture capital is easier than entrepreneurship or vice versa.

Ben: Venture capital is easier. That’s not even close. Who would think venture capital is harder than entrepreneurship? There’s a lot more luck involved in venture capital. If you join Andreessen Horowitz today, you have an amazing platform. You do three deals, maybe one turns into a trillion-dollar company. There’s a fair amount of luck around that.

Entrepreneurship doesn’t have a lot of luck. Some luck, but also a lot of bad luck. Entrepreneurship — you have one shot and you have to make it work. And you really pay for your mistakes much more directly. The clock is ticking. There are no “quarters” in venture capital. Venture capital is just an easier kind of business.

The pressure level and stress level are not close. If you have a small venture capital thing and it fails, it doesn’t affect a lot of people. You can get a tech company up to thousands of people and then lay them all off. That is common. And it’s brutal. Entrepreneurs may have one funding source, whereas venture capital generally has many funders.

Brian: All right. I hope you liked that episode with Ben. I really liked it. Learned a lot.

Something I thought about while he was talking: one of my bugs as CEO of HubSpot was I’m pretty conflict-averse. I think a lot of CEOs are — particularly first-time founder CEOs. a16z and Sequoia back a lot of first-time CEOs who haven’t really managed before. Confrontation is uncomfortable, unless you grew up with it. It’s just not natural.

Ben’s got a good term I’m going to borrow: constructive confrontation. You need a constructive level of confrontation with most people inside your organization.

Related to that — Ben talks about decision debt. You have a VP of Sales you need to fire, but you kick the can down the road hoping they nail the next quarter. Your pricing model isn’t working, but you wait a couple of quarters to fix it. I think it’s a lack of confidence. I wanted to be a popular CEO — that was another bug of mine, related to being conflict-averse.

This also connects to hiring and Founder Mode. When you’re a first-time founder CEO and you hire a “been there, done that” person who’s more senior than you, you’re a little nervous about truly managing them and you end up deferring. That’s where the problems start.

A lot of this idea around constructive confrontation is really productive. If you’re a little risk-averse like me, if you want to be popular like me, maybe you need to be a little more constructive in your confrontation.

Last thing: being a CEO is pretty uncomfortable, particularly at one of these hyper-growth companies today. They’re growing so fast, everything’s breaking, everything’s changing. It’s just fine if in your head you think you don’t know what you’re doing — Ben didn’t think he knew what he was doing when he was running Loudcloud, and I didn’t think I knew what I was doing when I was running HubSpot. If you’re feeling that as a CEO, I’m here for you.

Hope you liked it. Let’s keep the convo going. I’m Halligan on X. See you over there.

Transcript source: YouTube · Transcribed by AssemblyAI, edited by Claude Code