Ben Horowitz On What Makes a Great Founder

14:51Ben Horowitz:What's their weakness and how do I get to that? And so if you have an engineer talking to 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—

15:06Brian Halligan:I like this, by the way. I hadn't thought of it this way.

15:08Ben Horowitz: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, put a clean shirt on them and like make them the head of sales. And there's a real truth to 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?

15:40Brian Halligan:By the way, guaranteed, guaranteed they're going to be upset.

15:43Ben Horowitz: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 don't have a single fucking sales guy on the weekend who's selling software as a fucking hobby.

16:18Ben Horowitz:Like, that is not a fun job. There has to be 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 salespeople 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.

16:45Brian Halligan: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?

16:53Ben Horowitz:Yeah, well, it's funny. So, you know, one of the companies that boasts Sequoia and we were invested in is a company called Okta, 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 Ahrens, 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.

17:26Ben Horowitz:And I called them all, and they were like, this is a guy. And then this other guy, you know, I got front door references on him. And they came out okay, like not great. But Todd wanted to hire this other guy and the reason that he wanted to hire him was 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 and so forth and that kind of thing. And so, you know, the conversation I had with Todd was, I was like, Todd, you don't want the sales guy all enthusiastic. You want them to be qualifying you. Because when you're selling, good sales guys don't just answer the damn questions they're being asked.

18:08Ben Horowitz: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 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'll never forget it. And I don't talk to founders like this anymore because I'm more mature. But I said, Todd. Sure, sure.

18:44Brian Halligan:I'm still working on that.

18:45Ben Horowitz: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 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 him. And he hired Adam and, you know, it ended up really making the company.

19:07Brian Halligan:So that worked out. I have a bunch of questions.

19:09Ben Horowitz:But that's how important it is. Like, I think if we had hired the other guy, Okta would have gone bankrupt. Ooh.

19:14Brian Halligan:I have a couple questions on that. It sounds, well, just the takeaway if I'm that engineer who's CEO, I'm getting some traction, hiring that at sales. It's one, blind references really matter. And two, get a board.

19:26Ben Horowitz:Oh, on sales, by the way, it's the whole thing.

19:30Brian Halligan:Yeah.

19:31Ben Horowitz:Also, who are you bringing with you? That's what I always say. Who are you bringing with you? Okay, you're bringing this, 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.

19:59Brian Halligan: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 works 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 the fastest growing company in the world for a while. And we sold CAD CAM, we sold PLM software to manufacturers, hard sell, but we were very good at it. And the diaspora of PTC sales execs throughout Silicon Valley was very interesting and compelling.

20:35Ben Horowitz: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...

20:46Brian Halligan: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.

20:53Ben Horowitz:Yeah, like hire somebody selling Google AdWords. Fine. Like, you know what that job is? How much do you want? Totally.

21:00Brian Halligan:Okay. Totally. You're not going to build the... Okay, you see someone from Databricks, though, and they were a VP of Databricks, and you're looking for a CRO in 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 in an early-stage startup or no?

21:15Ben Horowitz:Well, you know, I can't comment on that because, you know, Databricks 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? Yep. And I think that, like, as it gets more established, it's harder to tell 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 talked about that, which was unique and probably illegal today.

21:54Ben Horowitz:I would say almost certainly illegal today. But the thing that I think is very replicable, but only if you have a difficult product to sell is the 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, you know, 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, like, lined up.

22:36Ben Horowitz:and that's so complicated and requires so much courage and effort and competitiveness that 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 OpenAI 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? Oh, we're PTC.

23:16Ben Horowitz: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 Ron Gabrisco, 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 he 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 selling that.

23:54Brian Halligan:Yep.

23:54Ben Horowitz: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?

24:40Ben Horowitz:That's a much harder find. 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.

24:50Brian Halligan:Some of my takeaways were, I was the first basically BDR and spent 10 years. It was, in a lot of ways, contrarian to 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 rep.

25:20Ben Horowitz:Yeah.

25:21Brian Halligan:And it's played down very, very well.

25:23Ben Horowitz:The profile. By the way, that's, when I interview sales guys, I always ask them, what's the profile of your rep?

25:30Brian Halligan:Yes.

25:30Ben Horowitz: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.

25:50Brian Halligan:One of the things we, just sticking on sales for a second, one of the things we got right, got a lot wrong at HubSpot, one of the things we got right was the process to interview a rep. And what we found out was reps who are good learners did well inside of HubSpot. And so we had lots of resumes. We like people on their second sales job, not their fifth, not their first or second. So they had done something. And if they had gone to a half decent school, not Harvard, not MIT, state school. State school, be everything. Yeah. An competitive athlete. If they could fog a mirror and they did those things, they came in and we didn't overthink it.

26:26Brian Halligan: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 HubSpot. And I'd give you 12 minutes to sell me, like literally watch 12. I'd say, that's very good, Ben. Here's my feedback. A couple minutes of feedback. Why don't 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.

26:54Ben Horowitz:Oh, that's interesting.

26:55Brian Halligan:Yeah, I thought that was, and it scaled really well.

26:58Ben Horowitz:Yeah, yeah, yeah. Right, can they, how good 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. It's an important, subtle difference.

27:15Brian Halligan:Okay, 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? Yeah, sure, sure. And the background of this was you had a big product launch coming, you were excited about it, and you had a press tour coming up in a couple weeks, and Marc Andreessen front-ran it, and you sent him an email, I guess we're not going to wait until the 5th to launch the product, Ben. And the response to Ben Horowitz from Mark Andreessen, apparently you don't understand how serious the situation is. We're getting killed, killed, killed out there.

27:47Brian Halligan: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. And then I love the ending. next time do the fucking interview yourself fuck off Mark yeah are we out of the fuck off era

28:10Ben Horowitz:from Mark

28:11Brian Halligan:everyone like this is emails that we get at PTC

28:16Ben Horowitz:oh yeah and are we too soft now you know Elon's not soft 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 wouldn't ask somebody that in an interview.

28:53Brian Halligan:My first interview, I walked in with my suit on, and Harrison, who was originally at a salesman, I wouldn't wear that suit to a shit fight.

29:02Ben Horowitz: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 mountaintop. 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.

29:44Ben Horowitz:Otherwise, the truth doesn't come out. Like, 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, 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.

30:23Ben Horowitz: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 the 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, it 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. We're not fucking late to meetings here. Like, that's not what we do.

30:59Ben Horowitz:And that's, look, not every company has that culture, but if you have that culture, you need to maintain it.

31:06Brian Halligan: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.

31:17Ben Horowitz: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. You know, and I think it came originally from Brian, Jessica. Sure. And so Brian, like I said, there's a part that's very right about it, which is what happened to Brian is he hired like extremely senior people. And then he did the thing that, you know, we talked about earlier, which he overtly deferred. Yeah. And then that created fiefdoms, politics, all kinds of like weird stuff. And then he kind of, after COVID, took the company back by going into quote founder mode.

31:55Ben Horowitz:And this is 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 a motherfucker 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?

32:27Ben Horowitz: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. And that's very different than avoid, avoid, avoid. And I think people have taken what Paul wrote and is like, oh, no, like, no, no, no experienced people. like screw that and so forth. And I, you know, particularly, you know, if you're an enterprise company, I think that definitely doesn't work.

33:02Ben Horowitz: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.

33:33Brian Halligan:I think you're, by the way, I think you're spot 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 CEOs I coach, none of them really do that. They don't have 60 direct reports. They haven't followed his playbook. I kind of scratched my head on it.

33:53Ben Horowitz:Well, people also haven't followed Elon's playbook, right?

33:56Brian Halligan:Exactly. No one uses the algorithm outside of Elon's companies. I don't get it. You notice the same thing.

34:01Ben Horowitz: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, that's a little bit like I'd say closer to how I run Andreessen 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.

34:48Ben Horowitz:They either can do it or they can't.

34:49Brian Halligan:I agree with you on that.

34:51Ben Horowitz:And then you have to feel like you've got enough knowledge to just be able to walk in and understand what's going on and so forth and kind of be able to evaluate how the company's going at that level. You know, Elon is the most competent and has the most confidence of anyone, and Jensen is kind of at that caliber. I think that a lot of people 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 Sherrill for a while until he could kind of build his confidence over there.

35:31And I think that's a little more the normal path.

35:36Ben Horowitz: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—

35:45Brian Halligan:30 years. Yeah, 30 plus years.

35:47Ben Horowitz:So, you know, what was he like four years in? I suspect he wasn't quite at this level of master of the universe.

35:53Brian Halligan:What can the CEOs listening learn?

35:56Ben Horowitz:And Elon, of course, got fired early. Like, there is a learning curve to the job, even for the best.

36:01Brian Halligan:What can CEOs learn from Zuckerberg? You work with him pretty closely here.

36:05Ben Horowitz: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, 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.

36:47Ben Horowitz: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.

36:57Brian Halligan:And do you think they always were? Zuckerberg struck me as that not being the case early.

37:01Ben Horowitz:He was so introverted that you couldn't see it, but I felt like it was going on inside his head. And, 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 in it. 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. Funny.

37:30Brian Halligan:Yeah. You wrote a whole book about culture. What are people getting wrong?

37:35Ben Horowitz: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 Sarandos, you know? And I realized after I wrote it, you really don't have the cultural issue till you get big. And so at the startup phase, you may be sowing the seeds of your own cultural problems, but there are no cultural issues in the beginning because the thing is small. You're seeing it, you're kind of managing the culture by hand unconsciously. So the big thing that people, people think of culture as values.

38:18Ben Horowitz: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.

38:24Brian Halligan:Everyone's got the same ones.

38:25Ben Horowitz:Yeah, 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 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? Okay, we're in venture capital. What does everybody, 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.

39:06Ben Horowitz: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 a pitch me? Do you get back to the entrepreneur if you're not going to 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 that's 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?

39:47Ben Horowitz: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.

40:04Brian Halligan:Let me ask you about one.

40:05Ben Horowitz:No, you may not want that, you know?

40:07Brian Halligan: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.

40:17Ben Horowitz:Yeah, yeah, yeah. Not sometimes. But by the way, venture capital is more like that than engineering organizations. There's more of those. 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 the night and I rewrite your code, that's going to be tricky as you grow. Like, that's hard to manage. If asshole 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?

40:58Ben Horowitz: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. You know, you get a lot of 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 did he come out?

41:30Brian Halligan:I've had the same debate.

41:32Ben Horowitz:Yeah, so I think it's a little bit more the latter. And so I think that if you're running an organization...

41:39Brian Halligan:Wait, which one was the latter? I forgot.

41:41Ben Horowitz:That he could get away with it, right? 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 in engineering and BC and whatever.

42:16Ben Horowitz: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 of this illicit is like, look, you can't make yourself look smart by making somebody else look 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, that 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.

42:52Ben Horowitz: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 dumbass conversation. Like, you know, if people who are extremely smart 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.

43:24Brian Halligan:But there's, Ben Horowitz isn't like, don't tolerate it, zero tolerance for this thing. It's...

43:29Ben Horowitz:No, I think that no asshole role is never going to work.

43:32Brian Halligan:Yeah, yeah.

43:32Ben Horowitz:So what is it that you don't want them to do?

43:35Brian Halligan:Yeah.

43:36Ben Horowitz: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.

43:43Brian Halligan:He's very spiky. Yeah. Yeah. What percentage, I like, you brought this up in another pod that I wanted to follow up on. Like, when I was CEO of HubSot, I didn't know what I was doing a lot of time. I was confused a lot. And when you were a 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, founders pretend like they know what they're doing.

44:10Ben Horowitz:Yeah, well, everybody pretends. And this is kind of part of the challenge. So I think it takes a while. I mean, like I, now, like I had to grow up very fast. We went public when we were 18 months old, right? Yeah. So 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 for us, 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 like 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.

45:03Ben Horowitz: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.

45:20Brian Halligan: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.

45:30Ben Horowitz:Venture capital is easier. What are you talking about? Way easier. Like that's not even close. I agree.

45:38Brian Halligan:Like who the fuck would think venture capital? Well, it's harder than entrepreneurs. A lot of people. I think the venture capital, there's a lot more luck involved. Like if you join Andreessen Horowitz today, you have an amazing platform or Sequoia, an amazing platform. And you may do three deals. You know, maybe one turns into a trillion-dollar company. There's a fair amount of luck around that. Yeah.

45:57Ben Horowitz:Yeah, I mean, I think that—

45:59Brian Halligan:Entrepreneurship doesn't have a lot of luck. It's just some luck.

46:02Ben Horowitz:It's also a lot of bad luck. 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. And I suppose if you failed in it, it might have looked harder 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.

46:48Ben Horowitz:Like you can get a tech company up to thousands of people and then have them lay them all off.

46:55Brian Halligan:Yes.

46:55Ben Horowitz:Like that is common.

46:56Brian Halligan:Yeah.

46:57Ben Horowitz: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, you know, many funders. Very generally have many funders.

47:15Brian Halligan:I appreciate your coming on the pot.

47:17Ben Horowitz:Yeah, no, it was fun.

47:18Brian Halligan:All right. Yeah, thank you very much. I think all the CEOs who are watching are going to really like it. Thank you.

47:23Ben Horowitz:All right, good, good, good.

47:24Brian Halligan:Okay, I hope you liked that episode with Ben. and I really liked it, learned a lot. Something I thought about while he was talking is 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. Andreessen 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 your organization.

48:06Brian Halligan: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-averse thing. All of this also rhymes, I think, with hiring.

48:39Brian Halligan: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 been there, done that person that's more senior than you, has 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.

49:21Brian Halligan: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. 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 convo going. I'm at bhaligononx. See you over there.

50:20Brian Halligan:is for educational purposes only and is not a recommendation to buy, hold, or sell any investment or financial product. This podcast has been produced by a third party and may include paid promotional advertisements, other company references, and individuals unaffiliated with A16Z. Such advertisements, companies, and individuals are not endorsed by AH Capital Management LLC, A16Z, or any of its affiliates. Information is from sources deemed reliable on the date of publication, but A16Z does not guarantee its accuracy.