The a16z Show - Ben Horowitz On What Makes a Great Founder

Episode Date: March 3, 2026

On the show Long Strange Trip, Sequoia Capital partner Brian Halligan speaks with a16z’s Ben Horowitz about what separates great founder CEOs from everyone else. Ben explains why first-time founders lose confidence, defer too much to senior hires, and let decision debt paralyze their companies. They discuss where founder mode works and where people are taking it too far, why the VP of Sales is the hire founders mess up more than any other, and why Andy Grove's "constructive confrontation" matters more than most CEOs realize. Ben also shares what he's learned working with Zuckerberg, what Jensen Huang and Elon Musk actually have in common, and why culture is defined by behavior, not values.   Resources: Follow Brian Halligan on X: https://twitter.com/bhalligan Follow Ben Horowitz on X: https://twitter.com/bhorowitz Listen to more from Long Strange Trip: https://www.youtube.com/playlist?list=PLOhHNjZItNnNu8wknSuVtcSJRs7Q4xqOE   Stay Updated:Find a16z on YouTube: YouTubeFind a16z on XFind a16z on LinkedInListen to the a16z Show on SpotifyListen to the a16z Show on Apple PodcastsFollow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

I think really good companies, the very, very, very best companies tend to have founders in 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 the tech company. And the kind of corollary to that is it's really important that like bad news travels fast. Yeah. that if something's wrong, that as CEO, you find out about it. And so you need that bluntness. Ben Horowitz didn't feel like he knew what he was doing as CEO

until about four years in. His company went public when it was 18 months old. He says that feeling is more normal than most founders admit. Horowitz has spent more than 15 years at Andreessen Horowitz, backing and coaching founder CEOs. The pattern he sees in the ones who fail isn't a lack of intelligence. It's hesitation. They see a problem.

The head of sales who isn't working, a decision that needs to be made, and they wait. Brian Halligan calls that decision debt. Horowitz says it's the worst kind because it paralyzes everything downstream. This conversation covers where a founder mode works and where it's being taken too far, why the VP of Sales is the higher that goes wrong more than any other, and what Zuckerberg, Jensen, and Elon actually haven't come. In this episode previously aired on the show, Long Strange Trip, Brian Halligan, partner at Sequoia Capital, speaks with Ben Horowitz, co-founder and general partner at A16Z. 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 Andreson passed on HubSpot back of the day, and this is a funny story behind that.

He's seen so much. He's back 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 are they like? What's the patterns there?

And the same of 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 is I think's 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? Yeah, remind me.

Can I tell you about it? It's stuck in my mind. Kind of a long story. HubSpot pitched you on the series D. Okay, I remember that. Yeah. Three of us came in for the pitch. Our very newly hired COO, J.D. Sherman,

myself, 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're like, this is a hometown. We got this. Yeah, yeah, yeah, yeah.

So we sat down and J.D. sat here and I sat here and Darmash sat here. I remember like it was yesterday. And we started with intros. Jaddy barely got a sentence out of his place.

Like, wait, you're the CEO? Tell me about your background. You spent like 15 minutes on JD. You spent like 15 minutes on JD and then went to me. And then it's about 15 minutes on me like, you're such a knuckle. Why did you hire a COO and then Darmash? Anyway, you guys passed, as did everyone.

Yeah. Two weeks later, I read your book. And I saw on 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 J.D. Sherman's shoulder. Oh, good. It was incredibly beneficial.

How do you feel about CEOs these days? you same thing or change your mind? Well, no, I mean, I think that generally when a company is small, flatter is better. In the early 2000s is a very popular construct, and it was kind of Mr. Outside, Mr. Inside, that kind of thing. You know, if you're really scaling and you're not kind of wrestling with product market, 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, like that's fine, you know. CO in the sense that I'm running the company and you're like Mr. Thotman outside, I think that's a great thing for a start of. Yeah. You've invested tons of CEOs at this point, coached tons.

What, like, what are you looking for? What's like a major green flag, red flag? How's it changed over time? Like, what's your filter? On a CEO? Founder CEO. So you're looking at the company in the market, but the person, not the co-founder of the CEO.

The thing about founder's CEOs is that there's definitely not what I would consider, like a canonical one. So if you look at Mark Zuckerberg and Ali Goetzee and Elon Musk, They're all, like, extremely different types of people. So, you know, you try not to get into, like, anything about the look and feel or sound or, like, you know, are they very extroverted or are they very introverted or this kind? And none of that I think matters.

There's a few things in common. One is, you know, anybody great really thinks for themselves. So they don't feel like they're reading the room or influenced by what I'm going to say or anything like that. And you could probably figure that out during the pitch you, think. Well, you can figure out if they're not that during the pitch, for sure. And then, you know, do they have, like, truly original thinking on things? So, and then, you know, from a leadership standpoint, I really like the Colin Powell definition, which is, you know, leadership is ability

to get people to follow you, if only out of curiosity. So I think, well, would I want to work for this person, like, how interesting are they? And if you don't have that, right, you're not going to bring in the super high-end talent, which is, you know, it's kind of a momentum thing. If you can't hire the very, very top talent, then you're not very unlikely to be a great company. It's kind of, you know, how good is your talent density and all that kind of thing. We just had our Sequoia offsite and I got into, not an argument, but discussion with Sean McGuire, one of our partners. Yeah, he's very outspoken. Very outspoken. And he got up and he said, what we should be looking for are these founders,

that won the chess Olympiad or the math Olympiad in high school and surrounded by other of those folks. And he was very articulate on it. It made a good point. A lot of people shook their head. And I thought about it and I was like, well, HubSpod's no Tesla, but it did pretty well. And my co-founder and I were Sloan people.

Yeah. You know? And then we hired crapped tons of people from Northeastern. And I was like, it worked out pretty well. And then I just think, like, early in the cycle, maybe you need those PhDs and those, you know, chess champions, mad champions. But as it moves up the stack

as Salesforce and ServiceNow, kind of look like us. Do you have a take on my disagreement with Sean? Well, I think it depends a little on the era and the market. So if you look at HubSpot, right, like it was a marketing sales idea

as much as it was a technological idea, so you have to have great people on that side who tend not to be Math Olympians. Yes. And so for that company, I don't think that's right. for other companies, that's right.

The other thing is, you know, Math Olympiad is very specific. The very best companies are founded by exceptionally smart people. There's a question about that. I agree with him on that angle of it. You know, like how smart is Elon extremely fucking smart? Was he Math Olympiad? Probably not. Like, I don't think so.

But just like raw horsepower is pretty important. Like Larry Page is probably, you know, one of the smartest people in the world. That ends up mattering if you're going to build something Google size. It's very hard to imagine that without somebody like Larry Page who could even think of something that big. Yeah. He worked with a lot of CEOs. Who's the best?

Probably the best one that I personally work with right now is Ali Goetze at Databricks. He's a PhD in computer science. He's extremely smart. So he kind of meets the Sean McGuire test. But he's like an exceptionally good, you know, for an enterprise software CEO, he's exceptionally good at go-to-market, able to compete with Snowflake, which was a very, very good go-to-market organization. And then he's just absolutely paranoid.

The only person I ever known as paranoid as Ali, I mean, I guess Elon is this level of paranoid, but Andy Grove was this level of paranoid. He wrote a book about it. Yeah, yeah, exactly. You know, I think some of that comes from him being, and he's a refugee. He grew up in Iran, and then when the Atole Colmeni came in,

he had to flee to Sweden. Hopefully that's correcting now finally after all these years. but, you know, that having everything taken away from him really informed his psychology in a way that's, I'd say, very beneficial for a founder. Okay, I work with a lot of founders, their companies are growing fast, and I'm kind of new to this.

What's the pattern of mistakes these folks make on the way up? Yes. What are the common traps? So, look, I think the universal one is kind of starts with, it's kind of confidence, is way kind of in a word. But it starts with the fact that nobody knows what they're doing, is you probably have experienced yourself. You have an idea.

You invent something. You're not to run a company. No idea. And so you start building the company, and you make a lot of mistakes. Those mistakes are extremely damaging. You feel terrible about it because you hired all the people. You sold them on this great idea.

Then you make a mistake and everybody gets hurt. And if you've not kind of been a position like that, which almost no founder has, it can be highly psychologically challenging. And you see people react to it in two very dangerous ways. One is they overly defer. So, okay, 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 I'm not really making the decision myself. I'm kind of doing a poll. But nobody other than the CEO has the contacts to make that decision. Nobody kind of sees the whole picture. And so that can lead you into not only bad decisions, but a very dangerous political environment where people go, oh, there's a vacuum here. I can step into it. And then the second thing that you see often is just hesitation. I don't know what the right answer is.

I have a suspicion. I'm like 52-48 on it, but I'm afraid of making mistakes, so I'm going to not decide. And then the other kind of hesitation is, well, I'm going to avoid it. Like, I see something bad. I really need to fire the head of sales. What is the press going to say? What is my board going to say? What is this going to be?

And just thinking about everything that you should not be thinking about rather than can this person do the job. And those things are really what caused founders to fail at the CEO job. That lack of confidence, that hesitation. You know, when I talk to CEOs, I'm like, like if you were like a linebacker in the NFL and you were really fast, but you didn't trust your eyes, you would get cut. Because you wouldn't get to the, no matter how fast you are,

you're not going to get to the ball carrying 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. You're going to, like, that's what's going to get you replaced. It resonates with me at HubSpot. We had all kinds of debt, culture debt, product debt. We had decision debt at times, I would call it. Yeah, yeah.

And when the company was... Decision debt is the worst step, by the way, because it paralyzes a company. We had, I had it. Yeah. So I fell in your trap. And the way it kind of worked was I would see the company slowing down and just like a lot of debate and a lot of just stuff on my desk.

And then once every like four or five, six months, be like, I need to make some friggin decisions. And then once they made some decisions, it just kind of, everything just started moving and flowing. Yeah. So I felt that. that very much. Yeah.

What other mistakes that they made? Talk about the team building. Like, you've hired a lot of VP of sales. Like, people fuck up their VP of sales hires all the time. More than anything else,

yeah, more than anything else. So kind of more generically, hiring executives is also something you don't know how to do. Right? Like, it's a lot of times you don't even know what the job is. Like, what is the CFO?

What's a control structure? You know, what are these systems they speak up? And people go, and to hire them, like, with that level of knowledge and think they can, like, smell it out from talking to a person. And it's a little like trying to hire a Japanese interpreter and you don't know Japanese. Like, they're all going to sound pretty good. And it's going to be very hard for you to distinguish. So preparation, I would say, is very important in terms of, okay, have you

spoken to enough CEOs? Have you asked them, like, what's the difference between a good CFO and a great CFO, like, you know, how would you hire this person? What would you ask them? What would you want to see? You know, these kinds of things. And just to understand the job, I always say, if you have a chance, just try to do the job yourself, act in that role so that you can get a feel for what the challenge is in your company. And it's also right, like you don't want a generic CFO, you want one for your business. And then when you get into sales, so the problem that we have all the time is we have engineers running the company

and then they're hiring a head of sales. You could not be culturally different between like an engineer and a head of sales. The main thing is like right down to how they talk to you. So engineers, if you ask them a question, 100% of them will try and think of what is the correct answer to that question.

That's how they think about it. 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? Right? Because that's a clue. And so, you know, if you ask an engineer, like, does your product have this feature? The answer is yes or no.

If you ask a sales guy, it's like, okay, what competitor was in here that planted that trap for me? What's their weakness? And how do I get to that? And so if you have an engineer talking to a head, a good sales guy, it's going to upset them because they're often not going to answer the question. They're going to try and figure out why they're being asked that question. And so then... I like this, by the way, and not out of it this way.

Yeah, but the guys who are good at the job get rejected because you don't like them. And then the people who are terrible at it, those are the ones that end up getting hard. Mark Cranny used to say, you know, these CEOs, they just want to take a guy who failed the engineering test to put a clean shirt on them and, like, make them head of sales. And there's a real truth.

that. It's funny, I had this conversation with Sujay when he was at Dropbox. He goes, how do I like deal with the fact that our engineers are upset that we're going to pay the sales guys commissions? By the way, guarantee. Guaranteed they're going to be upset. Yeah, and I said, well, it's very

simple. Tell them, if they want to make commission, then they can fucking grab a bag and sell some fucking software. And if they don't hit their number, you're going to fire them. And if they want that job, they can get a commission. But otherwise, you know, shut the fuck up. You know, he said, oh, okay.

I never thought of it that way. I was like, look, the other question you can ask him is, do you have engineers that, like, on the weekend might write some software for fun, like as a hobby? And he goes, yeah. And I said, I guarantee you you don't have a single fucking sales guy on the weekend who's selling software as a fucking hobby. Like, that is not a fun job. There has to be a, it's a prize fight.

There is no fight without a prize. And I think that the whole mentality, the whole cultural difference between, like what founders are and what sales people are is so vast that, you know, somebody's got to have a conversation with them about, like, okay, what are you really looking for? Because otherwise, you're just going to get somebody who's not good at sales.

Okay, I'm the head of, I'm the engineer, I'm CEO of your brand new company. I'm likely to screw the higher up. What's your advice to me? Yeah. Well, it's funny. So, you know, one of the companies that both Sequoia and we were invested in this company called Acta,

which ended up doing very well. It's actually Pat Grady. I was on the board with Pat Grady on that one. I love those guys. Yeah, and, you know, the very first, like, big mistake that Todd almost made was hiring the head of sales. There were two candidates. One, I forgot his name,

and the other was Adam Erins, who was a PTC guy. You know, we knew everything about Adam because, you know, he had worked for Cranny. You know, he had worked for McMahon. Like, I knew everybody in the tree. And I called them all. And then they were like, this is a guy. And then this other guy, you know, I got front door references on him.

Yep. And they came out okay, like not great. Yeah. But Todd wanted to hire this other guy, and the reason that he wanted to hire him was he was much more enthusiastic about ACTA. Whereas Adam was like, well, I don't know about this company. Let me talk to some of your customers and so forth and that kind of thing. Yeah. And so, you know, the conversation I had with Todd was, I was like, Todd, you don't want the sales

guy all-enthusi, you want them to be qualifying you. Because when you're selling, good sales guys, don't just answer the damn questions are being asked. They qualify the customer. Do you really have the money? Do you really have the need? Do I really have a shot here, or am I politically already boxed out? You need that.

And I said, but beyond that, I got guys who owe me favors more than they owe Adam favors telling me he's great. And this other guy who always... all the guys owe him favors and don't owe me anything. Say he's a B. And so do not fuck this up. I'd never forget it. And I don't talk to founders like this anymore because I'm more mature.

But I said Todd. Sure. I'm still working on that. I said, Todd, look, if this hire doesn't work because we were in a lot of trouble at the time, you realize what's going to happen is this is the end of your company. Like, this is it. So you've got to be 100% confident because I'm telling you, you're wrong. And I have more experience

at this than you and so forth. So I really put pressure on them. And he hired at him and, you know, it ended up really making the company. So I have a bunch of questions. But that's how important is. Like, I think if we had hired the other guy, Octa would have gone bankrupt. I have a couple questions on that. It sounds, well, just the takeaway of I'm that engineer who's CEO, I'm getting subtraction, hiring that at sales. It's one,

blind references really matter. And two, get a... Oh, on sales. By the way, way, it's the whole thing. Yeah. Also, who are you bringing with you? That's what I always said. Who are you bringing with you? Okay, you're bringing this to that, the other, okay, can I call them?

And find out if they're coming. Yeah, yeah, yeah. Because any great sales leader has a big set of followers. And anyone who's not great. Nobody. Nobody. Because the one thing sales guys are, they're savvy about the leader. Yes.

Like, I've never met, even a mediocre salesperson. knows who's a good leader. Okay, you brought up PTC. You've hired people from PTC. I came from PTC. First of all, who's the equivalent of PTC now building on the sales leaders that are filling Silicon Valley?

I can't figure that out. And two, what do you think it was about the PTC that worked so well? And by the way, for the listeners, PTC was a great, still a great company, but in the 90s, it ripped and was fastest growing company in the world for a while. And we sold CAD CAM.

We sold PLM software to manufacture. It's a hard sell. but we were very good at it. And the diaspora of PTC sales execs throughout Silicon Valley was very interesting and compelling. There was a number of things about PTC, but one of the underrated things was the product wasn't that great, particularly the windshields.

Didn't work. Anybody can say. So you like to hire a sales guy that had a hard sale. You don't like to hire somebody who was like, yeah, he crushed his numbers, but anyone could have sold that. Yeah, like hire somebody selling Google AdWords. Fine. Like, you know what that job is?

How much do you want? Okay. You're not going to build the list. Okay, you see someone from Databricks, though, and they were a VP of Databricks, and you're looking for a CRO and your new company. I'm not saying that's easy to sell, but they have a brand,

they have like a lot of mojo. Is that someone you're looking for an early state startup or no? Well, you know, I can't comment on that because, you know, Data Bricks is... Well, do you know the analogy? Yeah, it's like the early days of Oracle. Those guys were different

than an Oracle salesperson today, right? And I think that, like, as it gets more established, it's harder to tell. Yeah. Because you can survive on that. But I will say this. If you have a product that's complicated to sell, then that's when you get to the PTC level. The thing about PTC that was so amazing other than, like, the culture and the attitude. So there's a culture and the attitude, and we talk about that, which was unique and probably illegal today.

It's almost certainly illegal today. But the thing that I think is very replicable, but only if you have a difficult product to sell us a discipline. And the discipline really came down to, okay, you're going into an account. You know there are competitors. And how systematic are you about laying the traps for the competitors, making sure you make a comprehensive technical case, a comprehensive business case, making sure that you've charted everybody in that organization who's in that decision process,

and it's a very complicated decision process for PTC, getting assurances that they're all lined up. And that's so complicated and requires so much courage and effort and competitiveness that translates into anything. Whereas, look, if you're walking into an account and they're already predisposed to buy, you can skip steps. you can get away with shit.

You know, you just have to call in, show up, hey, I'm the, you know, salesperson from, you know, blah, blah, blah, and, you know, away you go. You know, like right now, I think with Open AI and Anthropic and so forth, it's like that. It's like everybody wants to buy AI. They're already predisposed to buy.

Very, very different than, who the hell are you? I never heard of PTC. Okay, like now I'm in the door. Why should I buy this? I can't get it to work. well, like, let me walk you through how it's going to work, like these kinds of things. Yeah, that's invaluable if you have that. Actually, so that Ryan Gibrisco, who's kind of the original head of sales at Databricks,

we got him. I had never heard, like I had never heard of the company who was at, which was a public company. Imagine that a tech sales guy that I had never heard of his company. And the company was literally selling FTP. Okay. But secure FTP. Okay.

Like, think about how good at selling you have to be to make your number as a public company. and he's selling that. Yep. And so this guy, like, obviously had the discipline forced upon him, and he was extremely smart. And that combination, you know, I'll take that all day, you know, if you've got that. And so you'd rather have, you know, a successful company is fine, but some kind of playbook that was harder to write, some product that was harder to build.

And that's another big one is, can you run a playbook? Are you somebody who, like, 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 this very complicated piece of software, who figured out how to lock out the competition to train the Salesforce to discipline them, to do all that kind of thing? That's a much harder fight. And, you know, depending on the complexity, look, if you've got an easy product, then that's one kind of thing. If you've got a hard product, that's another. Some of my takeaways were I was the first basically BDR and spent 10 years.

It was in a lot of ways contrary into the way people thought about selling. We sold an application. We sold it one way. And then we moved into the platform business, totally changed the way we sold. Very disciplined on both sides and very process oriented, like really manage the process tightly. So we're very good at that and just very tight on the profile of sales route. Yeah.

And it's killed that very, very well. The profile. By the way, that's, when I interview sales guys, I always ask them, what's the profile of your rep? Yes. And it's amazing to me that guys who are very senior and very big jobs have sometimes very loose profiles. Whereas the ones who really have to compete, it's extremely tight. What they're looking for is so specific and, you know, often surprising. One of the things we just sticking on sales for a second,

one of the things we got right, got a lot wrong in Housebound, one of the things we got right was the process to interview a rep. And what we found out was reps who were good learners did well inside a HubSpot. And so we got lots of resumes. We like people on their second sales shop, not their fifth, not their first, their second, so they had done something. And if they had gone to a half decent school, not Harvard, not MIT, state school. State school, B, everything.

Yeah, and if competitive athlete, if they could fog a mirror and they did those things, they came in, and we didn't overthink it. We came in for a half hour, and the half hour was,

Ben, welcome, and I would give you a scenario, and I would be the customer, and I would say, sell me a hub spot. And I'd give you 12 minutes to sell me, like, literally watch 12. I said, that's very good, Ben. Here's my feedback.

A couple minutes of feedback. Once you think about it, and let's do it again. And if the person internalized that feedback and sold it better the second time, 99% of the time we hired them. Oh, that's interesting. Yeah, I thought that was pretty, and it scaled really well.

Yeah, yeah, yeah, yeah. Right. How good at they, are they at listening? This is, by the way, that's the other, I think, mistake people make. They look for somebody who's good at talking. You really want somebody who's good at listening. Yeah. It's an important, subtle difference. Yeah.

Okay, while we're on this type of thing, you were the recipient of maybe me my favorite email in the history of emails. May I read it to you? Sure, sorry. In the background of this was you had a big product launch coming. You were excited about it. And you had a press store coming up in a couple weeks. And Mark Andreessen front ran it. And you sent him an email. I guess we're not going to wait until the fifth to launch a product, Ben. And the response to Ben Horowitz from Mark Andreessen, apparently you don't understand how serious situation is. We're getting killed, killed, killed out there. Our current product is radical. worse than the competition.

We had nothing to save 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. And then I love the ending. Next time, do the fucking interview yourself. Fuck off, Mark. Yeah, yeah, yeah.

Are we out of the fuck off era? From Mark? Everyone. Like, this is the emails that we get at BTC. Oh, yeah. And are we too soft now? You know, Elon's not so. Nope.

And I think there's some of that. Like, I don't think it's quite at PTC level. So in Cranny's interview with McMahon, I think McMahon said to him, what would you do if I hit you in the face right now? And I think Cranny's response was, well, first of all, you better knock me out. And then McMahon says, well, like, but what would you do? He says, is this a question, are you testing my intelligence or my courage? Good answer. Yeah, yeah, and that kind of thing.

You went to ask somebody that in an interview. My first interview, I walked in my suit on in Harrison, who was originally at the sales, says, I wouldn't wear that suit to a shit fight. 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 are pretty, who have kind of gotten all the way to the mountains. top, they're pretty blunt. And I think, look, I think that's important in that. One of the most

critical things in a company culturally is, you know, one, you give direct feedback. And like, you can have it out. Like, you know, like, Mark was wrong on that feedback to me. I was right. But, like, it's important that he'd be able to say that. And then it's important that I'd be able to stand up to it. Otherwise, the truth doesn't come out. Like, you've got to, like, if you're running away from the truth to preserve feelings, that's a very dangerous thing in the tech company. And the kind of corollary to that is it's really important that like bad news travels fast. Yeah. That, you know, if something's wrong, that as CEO, you find out about it.

And so you need that bluntness. Andy Grove used to call it constructive confrontation. And he was, by the way, that's another one where one of my favorite Andy Grove anecdotes was somebody, was late to a meeting, you know, and then this is when Intel was a monster, and Andy was God and all that kind of thing, and they come in late to the meeting. And he just looks at them,

and he goes, all I have in this life is time, and you're fucking wasting it, you know, which is like the meanest thing you could ever say to somebody, but particularly as a company grows, you need to reset the culture, like if it's starting to fray at the edges.

You can't just let that go. And by him saying that, you know, might crush that person's feelings, but everybody's telling that story. To the point where I heard it, I didn't work for Intel, right? And that's a culture center. Like, we're not fucking light to meetings here. Like, that's not what we do.

And that's, look, not every company has that culture, but if you have that culture, you need to maintain it. Kind of speaking of that, I coach all these CEOs. Well, one thing I've noticed is Paul Graham wrote that founder mode memo. It strikes me as relatively standard operating procedure now. it's really, is that your reaction to it? Well, yes, although there's a part that's wrong to it. Okay.

Or there's a part that I would say is a little misleading to it. And I think it came originally from Brian, Jessica. Sure. And so Brian, like, so there's a part that's very right about it, which is what happened to Brian is he hired to, like, extremely senior people. Yeah. And then he did the thing that, you know, we talked earlier,

which he overtly deferred. Yeah. And then that created fiefdoms, politics. all kinds of weird stuff. And then he kind of, after COVID, took the company back by going into Quote Founder Mode. And just as like, I'm being much more dictatorial. And I think that that part is all correct.

I think the danger with the idea is people are taking it to the point where they're going, well, I don't want to hire any senior people. Yeah, I see that. It's like, well, okay, so you're going to go compete with, and you need a worldwide sales organization, and you're going to try and grow more. from scratch to do that. Well, let me tell you all the things

that 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? Like, how do you open up international? How do you, like, there's just like years

and years of experience and relationships that are required to do that right. And so because you're in founder mode, you're so fucking afraid to do that. It's like, no, you need to be able to hire that person too when you need them, but you need to be able to manage them. that's very different than avoid, avoid, avoid.

And I think people have taken what Paul wrote and is like, oh, no, like, no experience people, like screw that and so forth. And particularly, you know, if you're an enterprise company, I think that definitely doesn't work. Like, even on a consumer company, it's going to be shaky, you know, like positions like CFO and so forth. Like outside knowledge is just valuable.

You have to understand enough about that, you know, in founder mode, you've got to learn enough about that job that you feel confident managing that person and telling them what to do and not having them tell you what to do because that's when you lose the company. So I think it's good. It's like an overcorrection from where things were.

I think you're, by the way, I think you're spot on on that. One of my favorite CEOs is Jensen Huang, and he's got a unique playbook. He's got 60 direct reports. He gives feedback in public and everybody knows the story. The interesting thing about the CEO, as I coach, none of them really do that. They don't have 60 direct reports.

They haven't followed his playbook. I kind of scratch my head on it. Well, people also haven't followed Elon's playbook, right? Exactly. No one uses the algorithm outside of Elon's companies. I don't get it. You notice the same thing. So most of the companies you recruit out of don't run like that.

And so they don't think of it that way. And then also, I think that to run it like Jensen does, by the way, you know, that's a little bit like I would say closer to how I run Andresa and Horowitz is more like how Jensen operates. But you got to, like, I think what founders are lacking is the level of confidence that you have to have to do that. Because you have to be able to say, if you're reporting to me, you got to be like basically CEO caliber. Autonomous. I'm not developing you, which is something that I highly believe in CEOs can't really develop.

executives. They either can do it or they can't. I agree with you on that. And then you have to feel like you've got enough knowledge to just be able to like walk in and understand what's going on and so forth and kind of be able to evaluate how the company is going from, you know, at that level. You know, Elon is the most competent and has the most confidence of anyone. And, you know, Jensen is kind of at that caliber. I think that a lot of people, you know, need to develop that as they go. I would say like when I, observed Zuckerberg, he didn't have that the whole way. He's kind of over time getting more like that. But, you know, like he deferred like half the company to Cheryl for a while

until he could kind of build his confidence over there. And I think that's a little more the normal path. It's hard to go from zero to Jensen. Yeah. You know, like, I mean, you know, it's interesting. Jensen's been doing it now for 30 years. Yeah, 30 plus years. So, you know, what was he like four years on?

I suspect he wasn't quite at this level of Master of the Universe. What can the CEOs listening learn? And Elon, of course, got fired early. Like, you do, like, there is a learning curve to the job, even for the best. What can CEOs learn from Zuckerberg? You work with him pretty closely here. Well, I think Zuck, he's very, very, very good at operating from kind of first principles thinking, not being overly influenced by, one, anybody else's ideas or just.

like the way things are. Like he's very, very good at just looking at it. And then also, you know, they were amazingly disciplined at looking at things through a data lens. Like, okay, what does the data say and do that? And, you know, that's how they were able to grow it so fast to overcome the competition and these kinds of things. And he definitely stays, like, extremely curious,

which I think all the great CEOs are like very just interested in everything all the time. You know, I think people underestimate him and Elon and Jensen and so forth. They're like, oh, those guys are nerds. Their people skills are astoundingly good. And do you think they always were? Zuckerberg struck me as that not being the case early? He was so introverted that you couldn't see it,

but I felt like it was going on inside his head. You know, if you look at like the M&A deals he's done, he's like a really outstanding psychologist. And I think that he always had some of that. And, you know, his mom's in that profession, and she's very smart about it, Karen. I think it was always in there, but he needed the confidence to get it out.

I mean, he started that company when he was like a little kid. Yeah. You wrote a whole book about culture. Where do people get wrong? I think people don't know what it is. Like, I mean, that's the main thing. The main thing that particularly founders don't know,

which is why I wrote the book, although it's funny. The people who really liked that book were like Ted Sarando. you know, like, and I realized after I wrote it, you really don't have the cultural issue until you get big. And so at the startup phase,

you may be sowing the seeds of your own cultural, like, problems, but there are no cultural issues in the beginning because the thing is small, you're saying it, you're kind of managing the culture by hand unconsciously. So the big thing that people think of, culture is values. They think, oh, it's, you know, like we have a culture of integrity or we have a culture of, you know, whatever. All the same. Everyone's gets the same ones. Yeah. Do we have each other's backs or like whatever it is? And those things aren't really anything. They're just platitudes. The actual thing is behaviors. And so when you think about your culture, you kind of want to think about, like, what are the behaviors that puts you in a place where you're the kind of company that you want to be and give you the advantage that you you want to have. Okay, we're in venture capital. What does everybody in, well, we really

love entrepreneurs. Like everybody in venture capital fucking loves entrepreneurs. But then you get down to the way entrepreneurs talk about a lot of VCs and they're like, these guys are fucking arrogant, they're assholes, they talk down to me, this and that. Well, like, well, if you want to be this, why are you that? And it gets down to the behaviors. Are you on time for a pitch me? Are you on your phone during pitch me? Do you get back to the entrepreneur if you're not invest in them. Like these behaviors end up setting the culture whether you're like care about entrepreneurs, have respect for them, or you think you're above them. And it doesn't have anything to do with what you said. It has to do with what you do. Which is why I call

the book, What You Do Is Who You Are. But it's, that's the really the core thing. But it takes a lot of thought to say, okay, if I want to be this, how must I behave to get there? And, you know, you can say like, oh, treat the company's money like it's your own. Okay, great. But what does that mean? Well, where are you staying? What hotel? You know, how are you traveling?

What's your thing? And like, so if you want that, then that has to be systematic. Let me ask you about. Now, you may not want that, you know? There's one cultural gotcha that I see a lot where there's a brilliant, brilliant, 100x engineer in the company, that's an asshole. Yeah, yeah.

Not sometimes. By the way, venture capital is more like that than engineering organizations. There's more of those. Yes. Well, like, I mean, and I think that on an engineering team,

you kind of have to have the parameters of, okay, like, what does asshole mean? If asshole means that in the code review, I don't say anything, and then I go in the middle of night and I rewrite your code. That's going to be tricky as you grow. That's hard to manage.

If ASO is, I expect, like, a super high standard, that's another thing. And so you kind of want to define, like, okay, what is it that we're not going to do here? And the thing about engineers is they're, like, amazing at following rules. So if you make clear, like, what the parameters are on it, and I find that in venture capital too. Like, we have that, that's a venture capital problem if I ever heard one. Yes, you know. You get a lot of very. very smart, spiky personalities.

And, you know, Mark and I talk about this sometimes. It's like, well, 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, right? Where do you come out? I've had the same debate. Yeah. So I think it's a little bit more the latter. And so I think that if you're running an organization...

Wait, which one was the latter? I forgot. That he could get away with it. Like, he didn't have to do that. Like, but he could do that. And, you know, like, it's his company. He can do what he wants. I think that the problem with founders modeling themselves after jobs,

I mean, you know, to some extent after Elon is, well, if you're not jobs or Elon, maybe you can't get away with that. And, like, maybe people just walk out the damn door in a way that they went with those guys. And it's very hard to have, like, the highest performing talent without, like, them coming with some of those behaviors. You know, it doesn't matter like an engineering in B.C. and whatever. And so you kind of have to be very specific about, okay, we're not going to have this, but we'll have that. You know, one of the things that I've outlawed at the firm, which a lot of, you know, kind of people have this illquered is like, look, you can't make yourself look smart by making somebody else like dumb.

Like that doesn't, that fucking doesn't count here. And if you do it, by the way, with an entrepreneur, like if you get on Twitter and say, oh, let's be. business sells dollars for 85 cents. Ha, ha, ha, I'm so smart. Fuck you, you're fired. Like, I'm not dealing with that at all because that's just, like, not who we're going to be. We love that you're smart.

You can be as smart as you want to be. Like, that's fine. You don't have to get there through that method. And then once people know that, they're fine, like, not doing that. But I couldn't say, I think it would be hard to say, just don't be an asshole.

Because, like, sometimes, you know, the smart, like, they're just like, I'm not going to suffer through this dumb-ass conversation. Like, you know, people who are extremely smarter are going to do that. And it can't be like, no, you have to suffer through every dumb conversation. Like, that's not going to work. Okay, but there's Ben Horace isn't like, don't tolerate it, zero tolerance to this thing. No, I think that no asshole role is never going to work.

Yeah, yeah. So what is it that you don't want them to do? Yeah. Like what's over the line and what's not over the line? And like I think even like very spiky people can live in that kind of context. He's very spiky. Yeah. What percentage?

I like, you brought this up like in another pod that I wanted to follow up on. Like when I was CEO of HubSpot, I didn't know what I was doing a lot of time. I was confused a lot. And when you were CEO, you felt the same way. Like, what percentage of the time do you feel like I really don't know what I'm doing versus I kind of got a handle on this thing? And today, running Andreessen Horowitz or through your journey. Like I founders pretend. like they know what they're doing.

Yeah, well, everybody pretends. And this is kind of part of that challenge. So I think it takes a while. I mean, like I had to grow up very fast. We went public when we were 18 months old, right? Yeah. That'll grow you up in a hurry. Yes.

But I didn't really feel like I knew what I was doing there probably till four years into it. You know, when I rebuilt the sales forest, I brought in cranny, all that kind of thing. maybe three and a half, four years into it. And I was never as confident at that as I was as I am now. And it's different for different people, but you need like enough reps at it to have,

like 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. And those are all the things. That's why Jensen is so magical, right? Like he sits in the room. He talks to everybody.

He knows exactly what he wants. Same with Elon, right? Like he can just sit there and go. I guarantee you neither of them started that way. Yeah. You know, like you build it into that. I see silly things on Twitter where people say, venture capital is easier than entrepreneurship

or entrepreneurship is easier than venture capital. People ask me that. The capital is easier. Everybody's talking about. Way easier. Like that's not even. and close. I agree.

You the fuck would think venture capital is harder than entrepreneur. A lot of people. I think the venture capital, there's a lot more luck involved. Like if you join Andresen Horowitz today, you have an amazing platform or Sequoia, amazing platform. And you may do three deals. You know, maybe one turns into a trillion-dollar company that's a fair amount of luck around that. Yeah.

Yeah. I mean, I think that... Entrepreneurship doesn't have a lot of luck. It just some luck. It also a lot of bad luck. Yeah. You know, entrepreneurship... You have one shot and you have to make it work.

Yep. And then you really, really pay for your mistakes much more directly. And then the clock is ticking in a way. It's like, there are no quarters in venture capital. So like venture capital is just kind of like an easier kind of business. Now, look, there's a lot of people. I'm saying that as, you know, someone who succeeded in it. I suppose if you failed in it, it might have looked harder in it in a different way.

But I think the pressure level and the stress level is not close because if you have a small venture capital thing and it fails, it's never a lot of people. Like you can get a tech company up to thousands of people and then lay them all the off. Yes. Like that is common. Yeah.

And it's brutal. And then the people that you're raising money for have a much tighter eye on you because you could have one funding source. Whereas in venture capital, you always have many funders. Very generally have many funders. I appreciate your coming on the pot. Yeah, no, it was fun.

All right. Yeah, thank you very much. I think all the CEOs who watch are going to really like it. Thank you. All right, good, good, good. Okay, I hope you liked that episode with Ben. I really liked it. Learned a lot.

Something I thought about while he was talking is one of my bugs, the CEO of HubSpot, was I'm pretty conflict. diverse. I think a lot of CEOs are, particularly first-time founder CEOs, Andresa Horowitz and Sequoia back a lot of first-time CEOs who haven't really managed before. And it's just uncomfortable. Confrontation is uncomfortable. Unless you kind of grew up with it, it's just not natural. Ben's got a good term that I'm going to borrow. He calls it constructive confrontation. I like that. You need to have a constructive level of confrontation with most people inside of the organization. I think kind of related to that, Ben talks about decision debt.

And we had this at HubSpot. You had a VP of sales. You know you need to fire them, but you kick the can down the road, hoping they nail the next quarter. You know your pricing model, not really working and scaling, but you kick the can down the road a couple quarters to fix it. There's all kinds of stuff kicking around your head like that. And, you know, I think it's a lack of confidence.

I want to be a popular CEO. I think that was another bug of mine kind of related with that. conflict-diverse thing. All of this also rhymes, I think, with hiring. And there's a lot of talk around founder mode and, you know, people hiring and deferring to people, and now they're micromanaging. I think when you're a first-time founder CEO and you're hiring a Ben-Dar gun that person that's more senior than you, had done more stuff in their career, you're a little nervous about truly managing them and you end up deferring to them. And that's where the problems start. And so I think a lot of this idea around constructive confrontation that Ben talked about is really productive.

And if you're a little risk averse like me, if you're a little, you want to be popular like me, maybe you need to be a little bit more constructive in your confrontation. The last thing I would say that he talked about and I agreed on is being a CEO is pretty uncomfortable, particularly from one of these hyper-growth CEO companies today. They're growing so fast, everything's breaking, everything's changing. I think it's just fine if in your head you think you don't know what you're doing because 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.

So if you're feeling that as a CEO, I'm here for you. Hope you liked it. Let's keep the combo going. I'm at B. Halligan-on-X. See you over there. Thanks for listening to this episode of the A16Z podcast. If you like this episode, be sure to like, comment, subscribe, leave us a rating or review, and share it with your friends and family.

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