Ben Horowitz On What Makes a Great Founder

26 Feb 2026 · 49 min · 23 chapters

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Podcast Summary: Long Strange Trip: CEO to CEO with Brian Halligan - Episode: Ben Horowitz On What Makes a Great Founder

Podcast Overview

In this episode of "Long Strange Trip

CEO to CEO," Brian Halligan, co-founder of HubSpot and Sequoia partner, engages in a candid dialogue with Ben Horowitz from A16z. The discussion revolves around the challenges faced by founder CEOs, the traits that define successful founders, and the pitfalls that many encounter on their journey.

Key Themes

  1. The Nature of Founder Mode
  2. Definition: Founder mode is described as a mindset where founders take full responsibility for outcomes and lead with confidence.
  3. Balance in Leadership: Horowitz emphasizes avoiding extreme deference to senior executives, which can lead to political dynamics and hinder decision-making.
  4. Constructive Confrontation: The ability to face truths, even if uncomfortable, is crucial for a healthy company culture.
  1. The Importance of Communication
  2. Fast-tracking Bad News: Horowitz stresses that bad news should be communicated quickly to prevent paralysis in decision-making.
  3. Decision Debt: Accumulating unmade decisions (termed "decision debt") can significantly hinder a company's progress and growth.
  1. Hiring Mistakes
  2. Common Pitfalls: Founders often struggle with hiring, particularly for VP of Sales roles. Horowitz identifies this as the most frequently mishandled position.
  3. Qualifying Candidates: Effective sales leaders should be able to qualify leads and understand the customer deeply rather than just charm stakeholders.
  1. The Psychology of Founders
  2. Self-Doubt: Many founders experience self-doubt and uncertainty, a common trait among successful leaders.
  3. Behavior Over Values: Culture is defined by actions rather than stated values. Horowitz argues that behaviors are the backbone of a company's culture.
  1. Learning from Failures
  2. Examining Great CEOs: Horowitz discusses the characteristics of successful founders like Zuckerberg, Jensen Huang, and Elon Musk, noting their ability to confront challenges plainly and realistically.
  1. The Role of Experience in Leadership
  2. Managing Senior Talent: Founders must learn to manage senior executives without deferring entirely to them to maintain control over company direction.

Key Takeaways

  • Constructive Confrontation: Founders should practice direct communication, especially when dealing with difficult truths.
  • Hiring Strategy: Understand the role requirements deeply before hiring; rely on references and past performance rather than charisma alone.
  • Self-Confidence: It’s normal for CEOs to feel uncertain. Embrace the discomfort and use it as motivation for growth.
  • Focus on Outcomes: Leaders must prioritize results over the process and have confidence in their decision-making abilities.

Conclusion This episode provides valuable insights for current and aspiring CEOs, especially those navigating the complexities of leading high-growth companies. The discussion emphasizes that while the journey of a founder can be fraught with challenges, understanding one’s leadership style and the dynamics of team management can pave the way for success.

Brian Halligan and Ben Horowitz's candid dialogue serves as a reminder that leadership is not just about making the right decisions but also about fostering an environment where constructive confrontation and clear communication can thrive.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Importance of Bluntness in Leadership

0:00 to 0:51

Learn why bluntness and transparency are critical for tech leaders.

“I think really good companies, the very, very, very best companies tend to have founders and CEOs who ask pretty aggressive questions.”

The Series D Pitch Experience

1:45 to 3:06

Discover a memorable pitch experience involving HubSpot and Ben Horowitz.

“You probably don't remember when we first met.”

The Role of COOs in Startups

3:06 to 4:07

Explore the evolving perspective on COOs in small companies.

“Well, no, I mean, I think that generally when a company is small, flatter is better.”

Qualities of Great Founders

4:07 to 5:31

Identify key traits that distinguish successful founders and CEOs.

“So you're looking at the company and the market, but the person, not the co-founder, the CEO?”

The Importance of Smart Leadership

5:31 to 7:11

Understand the significance of intelligence and originality in CEOs.

“It's kind of, you know, how good is your talent density and all that kind of thing.”

Ali Goetze: A Case Study in Leadership

7:11 to 8:12

Learn about Ali Goetze's effective leadership in a competitive environment.

“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.”

Common Mistakes Founders Make

8:12 to 11:04

Discover the common pitfalls and mistakes made by founders as they scale.

“And then when the Ayatollah Khomeini came in, he had to flee to Sweden.”

Hiring the Right Executives

11:04 to 14:02

Understand the challenges and strategies in hiring executives effectively.

“You're going to, like, that's what's going to get you replaced.”

Cultural Differences in Sales Roles

14:02 to 15:10

Explore the cultural clash between engineers and salespeople in startups.

“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.”

The Importance of Hiring Good Sales Leaders

15:11 to 18:18

Learn about the critical factors in hiring effective sales leadership for startups.

“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.”
Show all 23 chapters

Hiring Practices and Profiles for Sales Success

18:19 to 19:05

Discover the key characteristics to look for when hiring sales personnel.

“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.”

Lessons from the PTC Sales Culture

19:06 to 20:50

Understand the unique sales culture of PTC and its implications for hiring.

“And the diaspora of PTC sales execs throughout Silicon Valley was very interesting and compelling.”

The Complexities of Selling Difficult Products

20:51 to 22:35

Examine the challenges and strategies in selling complex software products.

“that was so amazing, other than, like, the culture and the attitude.”

Direct Feedback and Communication in Startups

22:36 to 27:45

Learn about the importance of direct communication and feedback culture in tech companies.

“So So Ron Gabrisco, who's kind of the original head of sales at Databricks, we got him.”

The Importance of Bluntness in Leadership

28:01 to 30:50

Learn why direct feedback and bad news traveling fast are crucial for CEOs.

“My first interview, I walked in with my suit on, and Harrison, who was the original head of sales, said, I wouldn't wear that suit to a shit fight.”

Navigating Founder Mode: Balancing Leadership Styles

30:51 to 32:58

Explore the complexities of founder mode and the importance of hiring experienced leaders.

“And then that created fiefdoms, politics, all kinds of like weird stuff.”

Lessons from Successful CEOs: Zuck, Elon, and Jensen

32:59 to 36:10

Discover what CEOs can learn from the operational styles of Zuckerberg, Elon Musk, and Jensen Huang.

“But people also haven't followed Elon's playbook, right?”

Understanding Company Culture: Beyond Values

36:11 to 37:55

Gain insights into what really defines company culture and how behaviors shape it.

“You know, if you look at like the M &A deals he's done, he's like a really outstanding psychologist.”

The Dilemma of High-Performing Individuals in Teams

37:56 to 42:01

Examine the challenges posed by brilliant but difficult personalities in organizations.

“What does everybody, well, we really, love entrepreneurs.”

Navigating Smart Conversations in Leadership

42:01 to 43:30

Discover the dynamics of managing smart individuals and the challenges of leadership conversations.

“You don't have to get there through that method.”

The Differences Between Entrepreneurship and Venture Capital

43:31 to 45:27

Learn about the contrasting pressures and challenges faced in entrepreneurship versus venture capital.

“But I didn't really feel like I knew what I was doing there probably till four years into it.”

The Importance of Constructive Confrontation

45:28 to 47:26

Explore the significance of having constructive confrontation in leadership and decision-making.

“So venture capital is just kind of like an easier kind of business.”

Embracing Uncertainty as a CEO

47:27 to 48:58

Understand the common feelings of uncertainty among CEOs and how to cope with them.

“but you kick the can down the road a couple quarters to fix it.”
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Transcript

Automatic transcript. May contain errors.

0:00Ben Horowitz:I think really good companies, the very, very, very best companies tend to have founders and CEOs who ask pretty aggressive questions.

0:09Brian Halligan:Zuckerberg, Larry Page, those guys who have kind of gotten all the way to the mountaintop, they're pretty blunt.

0:16Ben Horowitz:If you're running away from the truth to preserve feelings, that's a very dangerous thing in a tech company. And the kind of corollary to that is it's really important that like bad news travels fast. that if something's wrong, that as CEO, you find out about it. And so you need that bluntness.

0:50Hey, everybody.

0:51Brian Halligan:Today's guest is Ben Horowitz of A16Z fame. A few reasons I wanted to have him on. First, I wanted to get the behind-the-scenes look on why Andreessen passed on HubSpot back in the day, and there's a funny story behind that. He's seen so much. He's backed some amazing CEOs and some CEOs that went down in dust. Like, what do they have in common? What are the great ones? What do they do? What do they like? What's the patterns there? And the same with the ones who failed. I read his book like 100 years ago when I was running HubSpot. I thought it was really good. I think he published it in 2014. I wanted the updated, you know, what's changed since he wrote The Hard Thing About Hard Things back in the day.

1:36Brian Halligan: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.

1:46Ben Horowitz:You probably don't remember when we first met. Can I tell you about it?

1:51Brian Halligan:It's stuck in my mind. Kind of a long story. HubSpot pitched you on the Series D.

1:56Ben Horowitz:Okay, I remember that, yeah.

1:58Brian Halligan: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 were like, this is a hometown. We got this. Okay, we sat down, and J.D. sat here, and I sat here, and Dharmesh said, here, I remember it like it was yesterday. And we started with intros. JD barely got a sentence out of his mind.

2:28Brian Halligan:He's like, wait, you're the COO? Tell me about your background. You spent like 15 minutes on JD. You spent like 15 minutes on JD and then went to me. And then it's about 15 minutes on me like, you're such a knucklehead. Why did 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 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. It was incredibly beneficial. How do you feel about CEOs, COOs these days?

3:04Brian Halligan:Same thing or change your mind?

3:06Ben Horowitz:Well, no, I mean, I think that generally when a company is small, flatter is better. In the early 2000s, it was a very popular construct. And it was kind of Mr. Outside, Mr. Inside, that kind of thing. You know, if you're really scaling and you're not kind of wrestling with product market fit, like it can work for a time on a product cycle. But when you hit the end of the product cycle, it's so much about a company, a tech company is kind of the communication architecture. And it just makes that worse generally.

3:39Brian Halligan:It's a little like two people in charge.

3:41Ben Horowitz:Not to say it can't work. And, you know, 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. COO in the sense that I'm running the company and you're like Mr. Thought Man Outside, I think that's not a great thing for a startup, yeah.

3:58Brian Halligan:You've invested in 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 and the market, but the person, not the co-founder, the CEO?

4:15Ben Horowitz:The thing about founder CEOs is that there's definitely not what I would consider like a canonical one. So if you look at Mark Zuckerberg and Ali Goetze 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? Are they very introverted? Or this kind of 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.

4:56Brian Halligan:And you can probably figure that out during the pitch, you think?

4:59Ben Horowitz:Well, you can figure out if they're not that during the pitch, for sure. And then, you know, Or do they have like truly original thinking on things? And then, you know, from a leadership standpoint, I really like the Colin Powell definition, which is, you know, leadership is the 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.

5:37Ben Horowitz:It's kind of, you know, how good is your talent density and all that kind of thing.

5:41Brian Halligan:So 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, made a good point. A lot of people shook their head. And I thought about it and I was like, well, HubSpot's no Tesla, but it did pretty well. And my co-founder and I, we're Sloan people. Yeah, yeah, yeah. And then we hired crap tons of people from Northeastern.

6:17Brian Halligan: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, match 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?

6:33Ben Horowitz: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 olympiads 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 no question about that i agree with him on 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.

7:20Ben Horowitz:That ends up mattering if you're going to build something Google-sized. It's very hard to imagine that without somebody like Larry Page who could even think of something that big.

7:29Brian Halligan:Yeah. You've worked with a lot of CEOs. Who's the best?

7:31Ben Horowitz:Probably the best one that I personally work with right now is Ali Goetze at Databricks.

7:35Brian Halligan:Yeah.

7:36Ben Horowitz:You know, 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've ever known as paranoid as Ali, I mean, I guess Elon is this level of paranoid, but Andy Grove is 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.

8:11Ben Horowitz:he grew up in Iran. And then when the Ayatollah Khomeini 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.

8:31Brian Halligan:Okay, I work with a lot of founders and 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? What are the common traps?

8:44Ben Horowitz: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, as you probably have experienced yourself. You have an idea. You invent something. You're not going to run a company.

9:02Brian Halligan:No idea.

9:03Ben Horowitz:And so you start, you know, 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 in a position like that, which almost no founder has, it can be like highly psychologically challenging. And you see people react to it in two very dangerous ways. One is they overly defer. So, OK, 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.

9:43I'm kind of doing a poll.

9:45Ben Horowitz:But nobody other than the CEO has the context 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.

10:26Ben Horowitz:What is the press going to say? What is my board going to say? What is this going to be? And you're 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, 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.

11:04Ben Horowitz:You're going to, like, that's what's going to get you replaced.

11:07Brian Halligan: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.

11:17Ben Horowitz:Decision debt is the worst debt, by the way, because it paralyzes the company.

11:21Brian Halligan:I had it. 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 frigging decisions. And then once I made some decisions, it just kind of, everything just started moving and flowing. So I felt that very much. What other mistakes have 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.

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11:55Ben Horowitz: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? A lot of times you don't even know what the job is. Like, what is a CFO? What's a control structure? What are these systems they speak of? And people go in to hire them with that level of knowledge and think they can 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. 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?

12:39Ben Horowitz: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 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.

13:17Ben Horowitz: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?

13:59Ben Horowitz: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.

14:15Brian Halligan:I like this, by the way. I thought of it this way.

14:17Ben 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 Cranney 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?

14:48Brian Halligan:By the way, guaranteed. Guaranteed they're going to be upset. Yeah.

14:52Ben Horowitz: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, OK. 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.

15:27Ben 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.

15:53Brian Halligan:Okay, I'm the head of, I'm an engineer. I'm CEO of your brand new company. I'm likely to screw the higher up. What's your advice to me?

16:02Ben Horowitz:Yeah, well, it's funny. So, you know, one of the companies that both 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.

16:15Brian Halligan:I love those guys. Yeah.

16:16Ben Horowitz: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. 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.

16:54Whereas Adam was like, well, I don't know about this company.

16:58Ben Horowitz: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. 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.

17:35Ben Horowitz: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'd never forget it. And I don't talk to founders like this anymore because I'm more mature. But I said, Todd,

17:52Brian Halligan:I'm still working on that.

17:54Ben 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 percent 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 it ended up really making the company. So that worked out. I have a bunch of questions. But that's how important it is. I think if we had hired the other guy, Okta would have gone bankrupt. Ooh.

18:22Brian 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.

18:35Ben Horowitz:Sales, by the way, it's the whole thing.

18:38Brian Halligan:Yeah.

18:40Ben 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 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 you've I've never met even a mediocre salesperson knows who's a good leader okay you

19:09Brian Halligan: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 into what do you think it was about the PTC mafia that worked so well and by the way for 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 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.

19:43Ben 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. Yeah. Anybody can say.

19:54Brian Halligan:So you like when 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.

20:02Ben Horowitz:Yeah, like hire somebody selling Google AdWords. Like, you know what that job is? How much do you want? Okay, you're not going to build the...

20:12Brian Halligan:Okay, you see someone from Databricks, though, and they were a VP of Databricks, 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 an early stage startup or no? Well, you know, I can't comment on that because, you know, Databricks is... Well, you know the analogy.

20:29Ben Horowitz: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. Yep. 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 in the attitude, and we talk about that, which was unique and probably illegal today. 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.

21:13Ben Horowitz: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. 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.

22:13Ben Horowitz: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. 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 So 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.

22:47Ben Horowitz:Imagine that, a tech sales guy that I had never heard of his company. And the company was literally selling FTP.

22:55Brian Halligan:Okay.

22:55Ben Horowitz: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. 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?

23:36Ben Horowitz: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 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.

23:59Brian 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.

24:24Ben Horowitz:Yeah.

24:25Brian Halligan:So we're very good at that and just very tight on the profile of sales rep.

24:29Ben Horowitz:Yeah.

24:29Brian Halligan:And scaled that very, very well.

24:32Ben Horowitz:The profile. Yes. By the way, that's, when I interview sales guys, I always ask them, what's the profile of your rep? 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.

24:58Brian Halligan:One of the things we just, sticking on sales for a sec, 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 were good learners did well inside of HubSpot. And so we had lots of resumes. We like people on their second sales shop, 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.

25:27Ben Horowitz:State school, B-hour.

25:29Brian Halligan:Yeah. And 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 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.

26:03Ben Horowitz:Oh, that's interesting.

26:03Brian Halligan:And it scaled really well.

26:07Ben Horowitz:Yeah, yeah, yeah. Right. 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.

26:23Brian 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 Marc Andreessen, apparently you don't understand how serious the situation is. We're getting killed, killed, killed out there.

26:55Brian 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.

27:15Ben Horowitz:Yeah, yeah, yeah, yeah.

27:16Brian Halligan:Are we out of the fuck off era?

27:19Ben Horowitz:From Mark?

27:20Brian Halligan:Everyone. Like, this is emails that we get at PTC.

27:25Ben Horowitz:Oh, yeah.

27:26Brian Halligan:And are we too soft now?

27:27Ben Horowitz:You know, Elon's not soft.

27:28Brian Halligan:Nope.

27:29Ben Horowitz: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?

27:55Brian Halligan:Good answer. Yeah, yeah. And that kind of thing.

27:59Ben Horowitz:You wouldn't ask somebody that in an interview.

28:01Brian Halligan:My first interview, I walked in with my suit on, and Harrison, who was the original head of sales, said, I wouldn't wear that suit to a shit fight.

28:10Ben 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.

28:53Ben 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 bad news travels fast. That 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.

29:32Ben 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, you know, 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 that's a culture center. Like we're not fucking late to meetings here.

30:06Ben Horowitz: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.

30:14Brian 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.

30:26Ben 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.

30:37Brian Halligan:Sure.

30:38Ben Horowitz: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 overly deferred. 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. 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.

31:15Yeah, I see that.

31:17Ben Horowitz:It's like, well, OK, 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? Like how do you open it 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.

31:49Ben Horowitz: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 it's like, oh no, like no, no, no experienced

32:04Brian Halligan:people, like, screw that and so forth.

32:07Ben Horowitz:And I, you know, 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.

32:41Brian 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.

33:01Ben Horowitz:But people also haven't followed Elon's playbook, right?

33:05Brian Halligan:Exactly. No one uses the algorithm outside of Elon's companies. I don't get it. You notice the same thing.

33:10Ben 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, you know, 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.

33:56Ben Horowitz:They either can do it or they can't.

33:58Brian Halligan:I agree with you on that.

33:59Ben 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 is 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 he deferred like half the company to Sherrill for a while until he could kind of build his confidence over there.

34:40Ben Horowitz:And I think that's a little more the normal path. It's hard to go from zero to Jensen. Yeah. You know, it's interesting. Jensen's been doing it now for 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.

35:01Brian Halligan:What can the CEOs listening learn?

35:04Ben Horowitz:And Elon, of course, got fired early. Like there is a learning curve to the job, even for the best.

35:10Brian Halligan:What can CEOs learn from Zuckerberg? You work with him pretty closely here.

35:14Ben 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.

35:55Ben Horowitz:You know, I think people underestimate him and Elon and Jensen and so forth on they're like, oh, those guys are nerds. Their people skills are astoundingly good.

36:05Brian Halligan:And do you think they always were? Zuckerberg struck me as that not being the case early.

36:09Ben Horowitz: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 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. 20.

36:38Brian Halligan:Yeah. You wrote a whole book about culture. What are people getting wrong?

36:44Ben 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, like. 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 think of culture is values, they think, oh, it's like we have a culture of integrity or we have a culture of whatever.

37:32Ben Horowitz:All the same.

37:32Brian Halligan:Everyone's got the same ones.

37:33Ben 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.

38:12Ben Horowitz: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 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.

38:49But it takes a lot of thought to say, okay, if I want to be this, how must I behave to get there?

38:55Ben 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.

39:13Brian Halligan:Let me ask you about one.

39:14Ben Horowitz:Now, you may not want that, you know.

39:15Brian 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.

39:26Ben Horowitz:Yeah, yeah, yeah. Not sometimes. But by the way, venture capital is more like that than engineering organizations.

39:35Brian Halligan:There's more of those. Yes.

39:37Ben Horowitz: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 ASL 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.

40:16Ben Horowitz:Like, we have that. That's a venture capital problem, if I ever heard one. You get a lot of very smart, spiky personalities. And 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? Where do you come out?

40:39Brian Halligan:I've had the same debate.

40:40Ben Horowitz:Yeah. So I think it's a little bit more the latter. And so I think that if you're running an organization.

40:47Brian Halligan:Wait, which one was the latter? I forgot.

40:49Ben 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.

41:24Ben Horowitz:And so you kind of have to be very specific about, OK, 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 kind of people have this ill-quited is like, 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.

42:01Ben 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, look, sometimes, you know, the smartest, like, they're just like, I'm not going to suffer through this dumbass conversation. Like, you know, 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.

42:32Brian Halligan:But Ben Horowitz isn't like, don't tolerate it, zero tolerance for this thing.

42:38Ben Horowitz:No, I think that no asshole role is never going to work. Yeah, yeah, yeah. So what is it that you don't want him to do? Yeah. Like what's over the line and what's not over the line? And I think even very spiky people can live in that kind of context. He's very spiky.

42:52Brian Halligan: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.

43:18Ben 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. break. That'll grow you up in a hurry. 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.

44:11Ben 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. You know, like you build it into that.

44:28Brian 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.

44:39Ben Horowitz:Venture capital is easier. What are you talking about? Way easier. Like that's not even close.

44:46Brian Halligan:I agree. Who the fuck would think venture capital is harder than 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. Maybe one turns into a trillion-dollar company. There's a fair amount of luck around that. Yeah.

45:06Ben Horowitz:Yeah. I mean, I think that—

45:08Brian Halligan:Entrepreneurship doesn't have a lot of luck. It's just some luck. It's also a lot of bad luck. You know, entrepreneurship, you have one shot and you have to make it work.

45:17Ben Horowitz: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 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 someone who succeeded in it. 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. Like you can get a tech company up to thousands of people and then have them lay them all off.

46:03Brian Halligan:Yes.

46:03Ben Horowitz:Like that is common.

46:05Brian Halligan:Yeah.

46:05Ben 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.

46:24Brian Halligan:I appreciate your coming on the pot.

46:25Ben Horowitz:Yeah, no, it was fun.

46:26Brian Halligan:All right. Yeah. Thank you very much. I think all the CEOs who watch are going to really like it. Thank you.

46:31Ben Horowitz:All right. Good, good, good.

46:33Brian Halligan: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 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.

47:14Brian 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 in 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.

47:48Brian 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.

48:29Brian 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, So, I'm here for you. Hope you liked it. Let's keep the convo going. I'm at bhaligononx. See you over there.

From the publisher

A16z’s Ben Horowitz joins me for a raw, unfiltered conversation on what actually breaks founder CEOs, and what separates the great ones from the rest.

We unpack founder mode, where it works and where people are taking it too far. Ben shares why overly deferring to experienced executives creates politics and fiefdoms, but avoiding senior talent altogether is just as risky. Founder mode is not about micromanaging. It’s really about taking responsibility for outcomes and having the confidence to manage people who may have more experience than you.

Ben goes deep on “constructive confrontation” and why running away from the truth to preserve feelings is one of the most dangerous things you can do in a tech company. He explains why bad news has to travel fast, how decision debt paralyzes organizations, and why hesitation, not lack of intelligence, is what usually gets CEOs replaced.

We also dive deep into hiring, especially the VP of Sales role founders mess up more than any other. Ben breaks down why great sales leaders qualify you in the interview, why references matter more than charisma, and why selling a hard product builds a different kind of operator.

Along the way, we cover the psychology of being a first-time CEO, what Zuckerberg, Jensen, and Elon actually have in common, why culture is defined by behavior not values, and why feeling like you don’t know what you’re doing is more normal than most founders admit.

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