Brian Halligan: Leadership Lessons Scaling Hubspot to $28BN | E1103

1. 0:00 – 0:42

   Intro

   1. BHBrian Halligan0:00

      I had this (laughs) very bad snowmobile accident. Uh-

   2. HSHarry Stebbings0:03

      I love the way you're like laughing. This was such a serious accident.

   3. BHBrian Halligan0:06

      Yes. I thought I was going to die, like went off a cliff, was in the cold dark of night in Vermont. No one knew where I was. While I was sitting there, I was thinking a lot about my life in that moment. I thought, "If I make it alive, if I make it out of here, what should I change?" And one of the things I thought about on the bottom of that cliff was, "I don't want to be the CEO of HubSpot anymore."

   4. HSHarry Stebbings0:29

      Brian, I am so excited for this. I've heard so many things. You know I've stalked the shit out of you from all the references. But Paz told me so many good things for years, so thank you for joining me.

   5. BHBrian Halligan0:38

      Thank you for having me. I'm a big fan of the show.

   6. HSHarry Stebbings0:40

      That is very, very kind.

2. 0:42 – 15:21

   Paper Boy Beginnings

   1. HSHarry Stebbings0:42

      But I want to start, and I was reading and stalking, and I heard that your first job was as a paperboy for the Boston Evening Globe.

   2. BHBrian Halligan0:50

      Okay.

   3. HSHarry Stebbings0:50

      And you met a family called the Harrisons. Can you take me to that experience?

   4. BHBrian Halligan0:54

      Okay.

   5. HSHarry Stebbings0:54

      And what did you learn through the paperboy and the Harrisons?

   6. BHBrian Halligan0:58

      (laughs) Uh, you really did your homework, Harry. I, I, I take my hat off to you. I think I was 11 years old and I had a paper, paper, and there was, there was a low point on the route and a high point on the route. The low point was house numbers four and five. House number four had a German Shepherd that didn't like me coming on the front porch every day.

   7. HSHarry Stebbings1:19

      (laughs) .

   8. BHBrian Halligan1:19

      And house number five had a Doberman Pinscher that didn't take kindly to me coming on the porch every day. And so they would really give me a scare, and I had the paper route for years, and every - they never warmed up to me. So I got a good scare on house four and five.

   9. HSHarry Stebbings1:32

      (laughs) .

   10. BHBrian Halligan1:32

       And then house 16 was the Harrisons'. And the Harrisons were a very fun, very successful family. And I would come in, I'd deliver the paper to Mrs. Harrison, it was the last house in the route, and she would invite me in, and she was a terrific cook, and I would help her cook dinner, and she was super engaging. And she had four kids that were all a lot older than I was, and let's just say they were hyper over-achievers, much more over-achieving than, than, um, the Harrisons were. And I used to play like Nerf basketball with them in the living room and kind of got to, got to know them. And so that was my first job. And I was one of those people who said "I always had a job." But the reason that really paid off for me, and I think this is what you're referring to, is Richard Harrison, Pat Harrison's oldest son, gave me my first real job out of college. And it turned out to be a really good spot to start my career. So that paper route really paid off for me.

   11. HSHarry Stebbings2:28

       I mean, and it, it's funny actually, I watched, uh, I was looking at T- uh, Twitter the other day, and Dan Rooney said about the importance of saying yes and taking the opportunities, and you never know where they'll go. And you're like, "Huh, the paper route that led to the first job, that led to so much more," which we're going to get into. I guess my question-

   12. BHBrian Halligan2:45

       And, and, and Harry, it wasn't just the paper route, it was my mom. So Mrs. Harrison was very, very close friends with my mom. And my mom was a g- was a great, had lots of great friends. And so a little bit of it was my mom, who actually deserves a lot of credit for it. And my mom's not interested in technology or careers or something, just wasn't her MO. But she turned out to be, you know, a central player in my first job.

   13. HSHarry Stebbings3:09

       You know, in all the stalking that I did, how I knew that I'd like you so much, is 'cause you said that mothers are such an underrated element of a CEO's journey.

   14. BHBrian Halligan3:18

       Yeah.

   15. HSHarry Stebbings3:18

       And I mean, I couldn't do it without my mother, and so I just knew that, (laughs) great minds think alike in that way. But can I also, you know, when you think about that, and luck versus skill, when you reflect back on that in your career, how do you think about the weight of luck versus the weight of skill?

   16. BHBrian Halligan3:40

       Lot of luck getting... So my first job was at a company called PTC, and it was a CAD software company. And I was employee number 200, and, 100 years ago, in 1990. And I stayed for 10 years. And by the time I left, there were 5,000 employees. It was a great, I had a great run there. Um, and I just got very lucky landing in that spot. Um, and I give my mom and Mrs. Harrison all the credit. Uh, I think it was Louis Pasteur who said, "Luck favors the prepared." And if I were to do sort of a correlation of prepared versus luck, their high, the R squared on that is quite high. Uh, so I've always been over-prepared for everything. Um, and after that first job, I give preparation a fair amount of credit. Maybe it's half preparation, half luck, half right place at the right time. But people who are well-prepared tend to be at the right place and the right time, I've noticed.

   17. HSHarry Stebbings4:37

       I totally agree with you. And that's why you prepared so well for this show, (laughs) .

   18. BHBrian Halligan4:41

       (laughs) . You did. You called, I think you called my kindergarten teacher.

   19. HSHarry Stebbings4:45

       Uh, you know, you know what? They were sadly unavailable-

   20. BHBrian Halligan4:47

       (laughs) .

   21. HSHarry Stebbings4:48

       ... so, uh, your grade one teacher had to suffice.

   22. BHBrian Halligan4:50

       Okay.

   23. HSHarry Stebbings4:51

       Um, I also was looking at the schedule going, "Louis Pasteur said." I'm like, "I didn't know it was Louis Pasteur. This has to be Brian's intellect." (laughs) .

   24. BHBrian Halligan5:00

       (laughs) .

   25. HSHarry Stebbings5:00

       That is amazing. Uh, but I, but again, like thinking back to the paperboy, uh, route or kind of journey, you also said before that sometimes the lowest paying job is the best option for future CEOs. And I read this and I was like, "I don't actually know what he means by that." Is it Sheryl Sandberg, just get a seat on the rocket ship? What did you mean by sometimes the best is the lowest paying?

   26. BHBrian Halligan5:23

       I, I, I don't think Sheryl was way off on that. And that was very much the case for me. So I, I remember, this is really 100 years ago, but I had three offers. Um, and one was from PTC. And really, my first job, Harry, was I was an, what they used to call a secretary. I was a secretary to the head of sales in this company, head of channels actually. Uh, and that was the offer, was $20,000. And then I had two other offers for kind of sales positions in these two other companies, with higher pay.And I chose the lowest paying job with the company that had the most upside, and with somebody in there that I thought just might champion my career in this guy, Richard Harrison. That really paid off. I don't know what happened to those two other companies, but PTC is still around. It's a 20 billion market cap company. It's done quite well. And so, I don't think Sheryl is, is far off in that hop on the rocket ship, uh, quote.

   27. HSHarry Stebbings6:24

       I, I, I totally agree with you. I, I guess my question to you is, when you think about advising young people, say, there's often a debate of should I just start my company and you learn by doing, or should you join the rocket ship? Where do you land when advising people there? And I know people are different, and so it's hard to generalize, but if you were to.

   28. BHBrian Halligan6:44

       Yeah, I think it's super hard to generalize because there's people come at it from different angles and are very successful. My personal journey was I was, I joined two scale ups, not even startups. Like I joined a 200-person company that was growing quite fast, and, uh, that was PTC. And I ended up being their first basically inside sales rep in sales, in channels, in marketing. I ended up doing lots of different things, a movement in Asia to start Asia. Um, and, you know, if you're on a very fast-growing scale up, you get a lot of exposure, you get a lot of opportunity, so that really paid off for me. My second job was at a completely different company but also a scale-up called Groove Networks that eventually got acquired by Microsoft, for m- it was kind of a middling outcome. But same thing, I learned a lot, but instead of it at PTC, I learned a lot about selling, how do you, how do you build a sales organization, how do you hire reps, uh, how do you open international offices, how do you build a lead gen machine, how do you build that revenue engine? At Groove, it's totally different. The founder was very different. The orientation was it was a product company. I learned how to think about the future, think about products, think about technology, craft awesome solutions for customers, and I learned a lot in that journey. So for me, joining a scale-up twice really informed, uh, HubSpot and, like, PTC and Groove are very ... Both of those companies and their DNA are very much ins- I can look at things that happened inside of HubSpot and point back to those two companies.

   29. HSHarry Stebbings8:14

       We're going to dig into each of those components. I'm glad that you did a teaser. Uh, I do have to ask though, you know, when we think about ... And I love this, uh, when we think about reflections on, you know, earlier days, but also where we are today. I think everyone's running towards and running from something. Um, uh, I know I certainly am, uh, (laughs) my therapist tells me, uh, (laughs) -

   30. BHBrian Halligan8:36

       (laughs)
3. 15:21 – 20:00

   Brian's Snowmobile Incident & CEO Exit

   1. HSHarry Stebbings15:21

      uh, what did you cut out of your life that you didn't enjoy?

   2. BHBrian Halligan15:26

      Okay. I mentioned a minute ago I had this... (laughs) It was, it was a very bad snowmobile accident, uh-

   3. HSHarry Stebbings15:32

      I love the way you're like, just like laughing. This was such a serious accident.

   4. BHBrian Halligan15:36

      Yeah.

   5. HSHarry Stebbings15:36

      When I started-

   6. BHBrian Halligan15:37

      I almost, I thought I was going to die, like went off a cliff, was in the cold dark of night in Vermont, freezing cold night. No one knew where I was.

   7. HSHarry Stebbings15:47

      And now you know what it's like to be a public markets founder in 2024. (laughs)

   8. BHBrian Halligan15:52

      And, uh, anyway, I got very lucky and was saved. Um, but while I was sitting there, I was, uh, y- you know, I was thinking a lot about my life in that moment. And I'm fairly reflective about my life, and we're just coming off the new year, so I've been thinking a lot about it. But in that moment, I thought, "If I make it alive, if I make it out of here, what should I change?" And one of the things I thought about, it, on the bottom of that cliff, was, "I don't want to be the CEO of HubSpot anymore." You know, I started this thing. It's got 7,000 people. It's a big company. It's going great. But I don't think I'm necessarily well-suited for the next phase from 7,000 to 70,000 or whatever it is, from 20 billion market cap to 200 billion market cap. Um, I didn't necessarily enjoy the work at that size as much as I enjoyed it, you know, in an order of magnitude smaller. And so I really made the decision in my head on the bottom of that cliff that night that, "If I make it out alive, once I recover, I'm gonna hand the reins off." And that's exactly what happened. I was out of work for seven months, and seven months and a day, we gave the job to, uh, Yamini, she's terrific, who's CEO of HubSpot now, and I'm chairman. And that turned out to be a very good decision for me. I'm, I'm generally quite, quite a bit hap- I didn't love the work of a big company CEO, and I don't think I was that good at it.

   9. HSHarry Stebbings17:15

      Why? (laughs)

   10. BHBrian Halligan17:18

       I like it earlier, smaller team, where I know people, I'm really viscerally in, in touch with the product and the customers. Um, I'm not worried too much about governance, about enterprise risk management, about things like that. Uh, I don't spend much time at all speaking with lawyers and law firms. I like that... I like the scale-up phase of, you know, 20 to 2,000 I think was where I was at my best. I don't think I was at my best from two of us to 20, or 2,000 to where we are today, but I think I was kind of at my best between 20 and 2,000.

   11. HSHarry Stebbings17:56

       Do you think people are destined for certain stages of company-building? You know, there's that, like, c- c- very standard statement that, like, "Oh, people are very much meant for a certain stage." Do you buy that? Or are you like, "No, I've seen many people transcend that, and it's bullshit"?

   12. BHBrian Halligan18:10

       I think it's right. Um, I didn't think so when we started the company. The, the crew we hired in, in the early days of HubSpot were terrific, very bright. And I thought, you know, if we ever make it to the size we are now, which, you know, I would have put very low odds on that, uh, it would be the same crew. And we're, I think, on our third or fourth generation of leaders at HubSpot, and there was nothing wrong with that original crew. In fact, they've gone on to do amazing things. But I just don't think they were interested in that next phase. Uh, and so, I think you do need to... I think it needs to evolve and your team needs to evolve over time. And when I look at our team, and we'll probably get into this, but we've always had an interesting mix on our executive teams of people who we've hired, kind of been that, been there, done that from the outside, and then people who kind of came up through the system. And I like it, and I know you're from the UK, so you don't know about the... We have a, we have a thing in the United States, I don't know if you've heard of it, it's called baseball.

   13. HSHarry Stebbings19:11

       Yeah.

   14. BHBrian Halligan19:12

       (laughs)

   15. HSHarry Stebbings19:12

       I, I've heard of it. It's like rounders, but you know-

   16. BHBrian Halligan19:14

       Yes. Yes.

   17. HSHarry Stebbings19:14

       ... more popular. Yeah.

   18. BHBrian Halligan19:15

       And, like, the Boston Red Sox didn't win a world championship for 84 years, very frustrating, and they've won four in the last 20. And when I look at the teams that won, they were a nice combination of people they drafted out of high school and kind of came up through their system and really got it, mixed with some free agents who were a little more expensive from other teams who had seen success before, and that mix really works. And I think that has worked for HubSpot. We've got a mix of people who kind of grew up through our system and we hired people from the outside. That's, that's proven to work pretty well, I think. I think that's a good formula.

   19. HSHarry Stebbings19:50

       I, I totally agree. It's a good formula to have the combination. It's hard to do. Uh, the final one I just have to touch on before, uh, we, we do discuss some of the mechanics of your leadership, is,

4. 20:00 – 21:59

   Life Beyond CEO

   1. HSHarry Stebbings20:01

      I identify myself with 20VC. It's all I've ever known, uh, as an adult, which is quite terrifying. Um, you'd been involved for so long, it was such a part of your identity. Was it difficult to transition out, just in terms of losing a part of your identity?

   2. BHBrian Halligan20:20

      Okay. It, it's a really good point about that. I rem- I, I remember looking at my review, maybe s- five, six, seven years in, and, and seeing comments in my review about how Brian doesn't understand that he actually is HubSpot. Like, it's embodied in him, and that every action he takes and every decision he takes is really HubSpot in how those things came together. I was quite surprised at how much those things had merged together, in the employees' mind, at least. Um, and that was actually some useful feedback and useful revelation. It made me think more carefully, carefully about my actions and my decisions I was making, because I hadn't realized those things had kind of merged together. And I, I think that probably happens with CEOs of, or, or founders of all companies as they scale, and it took me by surprise how much those things came together. As we, as I transition out, I'm still involved, so it totally hasn't happened. Like, I'm still the chairperson. I still go to the office. Um, I'm still very... I just had a, you know, a call with a bunch of, uh, execs yesterday. I'm still very much involved. So I, I think I'm not totally dis- disassociated with it, and I think that's okay. If I had just left, Harry, I think that would have been tough for me. I think you're right. I think my identity is pretty wrapped up in HubSpot, and there'd be some sadness around that, I think.

   3. HSHarry Stebbings21:57

      Yeah. I agree.

5. 21:59 – 22:42

   Elon Musk on Vacations

   1. HSHarry Stebbings21:59

      I, I always struggle to go on holiday, because suddenly you're like apart from your work, and when your work is such a large part of you, it's like, feel quite isolated and not very good. (laughs)

   2. BHBrian Halligan22:10

      Yeah. I, so it's a non-sequitur, but, uh, in the Wall Street Journal yesterday or the day before, there was an article about Elon Musk. And Elon had an amazing quote about vacations. So he works, you know, a crazy amount of hours, and he said, "Oh, yeah, yeah, vacation. That's email with a nice view." (laughs)

   3. HSHarry Stebbings22:31

      (laughs)

   4. BHBrian Halligan22:31

      I thought that was pretty funny, actually.

   5. HSHarry Stebbings22:33

      I mean, I, I love that. I'm just not going to tell it to my team here already telling me that culture is something I need to work on. Uh... (laughs)

   6. BHBrian Halligan22:41

      Yeah. (laughs)

   7. HSHarry Stebbings22:41

      Um,

6. 22:42 – 27:25

   HubSpot's Company Survey

   1. HSHarry Stebbings22:42

      I do want to touch on your leadership. You know, it was something that so many of the references that I spoke to said that we really needed to dig in on. And I think people change so much over time. So when you compare, you know, Brian Halligan that started HubSpot in 2006, to the CEO that transitioned to Yamini in 2023, what are the biggest differences in that style of leadership?

   2. BHBrian Halligan23:06

      (laughs) Okay. I mentioned reviews earlier. One thing that my co-founder... One of the best things my co-founder, Dharmesh, has done is he owned doing my annual 360-degree review. And he did it in a, uh, remarkable way. Um, and we started doing this, like, s- five, six years in. The way Dharmesh does the reviews, Dharmesh is very introverted and does not want to talk to anyone. (laughs) He really doesn't. So he does a net promoter survey on me. And so he sends a net promoter survey, "On a scale of 1 to 10, how likely are you to refer Brian as the CEO of HubSpot, and then why?" And he sends it to 30 people, board members, executive team members, frontline members, customer partners. And people score me, and then they write a novel, Harry, like a novel (laughs) about, about, uh, about me. And then Dharmesh takes a while and synthesizes it together in a really cool way. And I remember the first one I got was 20 pages. So I... Uh, a review that was 20 pages long.And I started reading it. And the first, the beginning of it is, "Here's your f- here's your score, and then here's your features." So Brian's really good at explaining the vision of HubSpot, for example. And then he would pull out direct quotes from three or four of the people who had said that theme, and I could read the quotes. Brian was his... And I'm reading through it. In the first 10 pages, Harry, I was pretty convinced I was the best CEO ever, ever (laughs) because it was all my features. I got to page 10, halfway through, and the next 10 pages were my bugs. And there was a full 10 pages of bugs with direct quotes pulled out each one. And I had a big gla- I remember this (laughs) I sat down, I had a big glass of scotch when I was done with it, pretty well convinced I was the worst CEO ever invented (laughs) . But that was a very, very, very useful exercise we went through every year, and now Yamadi goes through it, to get awesome feedback that's well-organized. And it was great. And there was infinite numbers of things I was bad at and not good at, and they were all surfaced in that process. And...

   3. HSHarry Stebbings25:24

      Wha- wha- what, what are the biggest elements that you changed on the back of those reviews?

   4. BHBrian Halligan25:29

      Yeah. I would say (laughs) , I would say the biggest one that just I couldn't put to bed, and we'd come up year after year after year was, (laughs) my thinking is, is, is the, the control-freakedness of founders is a amazing strength in startup mode. And that amazing strength of founders turns into an amazing weakness as you scale. And you're, you're more prepared than everyone, you're overthinking, and you're basically doing everyone else's job. And that just came up over and over and over and over again. Um, and I do think I improved on that, uh, over time. And what I ended up, the ki- (laughs) the thing I ended up coming to, like the same weaknesses would come up year after year. And some of the weaknesses were, or some of the bugs are like, you know, at HubSpot if there's a bug sometimes it's like, "Actually, that's the way we designed it." (laughs) Worked as designed. Um, some of the bugs were actually, I thought, features, and they'd show up on both sides. So I would pick a couple things I would work on improving, and then a lot of them I would just be like, "You know what? I'm never going to get better at that. I'm going to tr- try to hire people who map perfectly into those weaknesses." So I'm the type of person who's, who, okay, great, I've got all these weaknesses. I, I try to hire around them and I try to advise my folks to hire around them. And I lean into my strengths. So if I have a strength that's like a 10X strength, how do I make that a 100X strength? So if I've got a weakness that it's a minus 10X strength, just leave it at minus 10X 'cause I'm never gonna get it to, to plus 10X. That's kind of how I think about it.

   5. HSHarry Stebbings27:08

      I totally agree with you. Did it upset you?

   6. BHBrian Halligan27:12

      Yeah, kinda.

   7. HSHarry Stebbings27:13

      Yeah.

   8. BHBrian Halligan27:15

      Mm. Kinda. Yeah. Reading that was, uh, was a lil' upsetting, was a lil' upsetting, yeah.

   9. HSHarry Stebbings27:20

      Do you think that-

   10. BHBrian Halligan27:20

       I will say, one piece of feedback I got back then (laughs)

7. 27:25 – 30:18

   Nvidia CEO Leadership Style

   1. BHBrian Halligan27:25

      , so I've been reading about, um, Jensen Huang and Elon, 'cause they've got such unusual CEO styles that completely fly in the face of everything that any CEO coach or anything (laughs) you read about being a CEO will teach you. And one thing I, Jensen Huang's really got a very different playbook. He's the CEO of NVIDIA. Um, one of the things he does is he criticizes in public. Okay. So he's got his team. He's got 40 direct reports, (laughs) which is pretty weird, or 50 direct reports. And if somebody says something he disagrees with or does something that he didn't like, he will in front of everyone... I, I think he does it in a very nice way, but admonish them or criticize them or give them feedback, so everyone can hear it. And I remember back in the day getting feedback that I used to do that. People really did not like it. And I probably didn't deliver it as diplomatically as, uh, Jensen does. And, um, that has popped into my mind, and I sort of fixed that. I, I always try to give fee- give kind of negative feedback in private and public praise in, uh, public. Um, but I wonder about that part.

   2. HSHarry Stebbings28:37

      Do you remember-

   3. BHBrian Halligan28:37

      I think J- I think Jensen might be-

   4. HSHarry Stebbings28:39

      Did you-

   5. BHBrian Halligan28:39

      ... onto something on that. I think I could have delivered it more diplomatically. But that was one I was thinking about as I was thinking about this interview, that I wonder, I wonder about.

   6. HSHarry Stebbings28:47

      Brian, help me. I'm a young CEO. I am incredibly direct. Me and you sit down. I say, "Brian, listen, let's be honest. That was shit. You need to improve on this, this, and this, and please don't do that again." And people find me too direct and too harsh-

   7. BHBrian Halligan29:02

      Mm-hmm.

   8. HSHarry Stebbings29:02

      ... if we're honest (laughs) . Um...

   9. BHBrian Halligan29:04

      I was the same. I was the same. I got more diplo- one of the things I worked on was getting more diplomatic over time. And it d- the other thing that I didn't realize is how much, Harry, people really listen to everything you say. And so you emerge w- as the founder with the company, everything you say, people pretend like they don't listen and they push back at you, but they remember what you say. You'll run into somebody in the, uh, uh, you know, you'll be walking down Newbury Street in Boston, bump into an employee, and you'll have coffee with them, and they'll say something to you, "Remember when you said this four years ago at a company meeting?" "No, I don't remember that (laughs) at all." Uh, so people really, really listen and overindex on what you say. And so I do think getting better and more diplomatic over time did help me and helped the company.

   10. HSHarry Stebbings29:53

       Uh, uh, can I ask, you said there about the control freakedness.

   11. BHBrian Halligan29:56

       Yes.

   12. HSHarry Stebbings29:56

       I get you, but I quite like sweating the detail. And I think some of the best founders do sweat the details. You mentioned Elon. You know, when you think about Elon and his mind, I don't know if you listened to, uh, the Walter Isaacson work that he did, but he said one of the most special things about him is like the detail orientation he applies to systems, machinery, systems thinking.And I'm like,

8. 30:18 – 35:23

   Musk's Team Building Tips

   1. HSHarry Stebbings30:18

      "I think Elon sweats the details, and I think some of the best do." How do you balance sweating the details but not being too control freakish?

   2. BHBrian Halligan30:27

      I th- I, I'm not an expert on this, but I think... Okay. I will tell you the one thing I learned from Elon. So, uh, Sequoia, Sequoia has an annual... (laughs) It's- I call it a glamping event. Um, and I'm, I'm, I, Dharmesh and I, I would describe us as, as indoorsy, not outdoorsy. And so they invited us to the glamping event. And we were like, our... We debated it, like, "Should we go? It's a fucking glamping event, but great speakers. It's gonna be really good." So we went. And I'll tell you a funny story about it. But it was the first glamping event, so we went, and the first night, Harry, was freezing cold.

   3. HSHarry Stebbings31:03

      (laughs)

   4. BHBrian Halligan31:03

      Freezing cold. And (laughs) it was freezing. And we're in tents. And I'm like, "God, why did I come here?" And my, and my tent mate was John Collison from Stripe. And I just remember, I was so darn cold that night, I was tempted to be like, "Hey, John," (laughs) "should we just cozy up here so we don't freeze to death tonight?"

   5. HSHarry Stebbings31:29

      (laughs)

   6. BHBrian Halligan31:29

      I fortunately resisted that temptation. But I, I've never been as cold. Anyway, the next day, Elon, uh, spoke. And I've, I remember his presentation. You probably would forget it. And he spoke about vectors. So he's a physicist, and he thinks about vectors and their power and their strength. And he talked about how organizations have... All their people are different vectors. And in most organizations, you have some strong vectors, really strong employees, and some, mm, less strong employees. And in most organizations, your vectors are pointed all over the place. And he's like, the one thing he focuses on, if he's detailed about, is just trying to get all those darn vectors pointing in the same direction. Small vector, big vector, but all pointing in the same direction. And I kind of think about it as inside of HubSpot, there's 8,000 people, and if everyone's pointing in different directions, you add... Let's say 8,000 is each a value of one, and they're all pointing each other, um, you get a value of zero. But if you get them all pointed in the same direction, you know, the value is 8,000. How do you get as close to 8,000 as you possibly can? I remember that clearly from him. So I think he wo- he's in detail on certain things, but certainly not everything. He's CEO of X number of companies. I can't remember, five, six companies. He can't be completely in the details and everything. But it's in the details on systems thinking types of things like that.

   7. HSHarry Stebbings32:46

      It's funny, 'cause I went to a Sequoia event, and John was my tent mate.

   8. BHBrian Halligan32:49

      (laughs)

   9. HSHarry Stebbings32:49

      And he actually suggested spooning. So, uh... (imitates fart)

   10. BHBrian Halligan32:53

       (laughs)

   11. HSHarry Stebbings32:54

       (laughs) Sean's gonna listen to this and be like, "What the fuck?" (laughs)

   12. BHBrian Halligan32:58

       (laughs)

   13. HSHarry Stebbings32:59

       Uh, my, my, my question to you is just on that, like, the vectors. What does that actually mean, Brian? Sorry. Does that mean, like, set a north star and align everyone to the same goal? Or is it, like, make everyone have the same similar broad set of skills? You don't want that, 'cause then you'll have weaknesses that aren't covered. What does that actually mean in reality?

   14. BHBrian Halligan33:15

       I think it's really underrated. And I see these startup... I've spent a lot of time with founder, uh, startup founders who are CEOs, and want to go from startup to scale-up. And I think a big leap for HubSpot was when we got on this vector bandwagon, and we got into a planning cycle where we can be like, "Here's what our mission is. Let's not change that, or change it rarely. Here's what our strategy is for thes- this year. Here are the main initiatives we're gonna work on for this year. Here's how we're going to track them. Here's the infinite number of initiatives that are proposed and people are kicking around and talking about and want to do in their pet rocks that we're not doing this year, and we're just gonna ignore them for another year." Once we got some discipline around that, the, uh, th- uh, and the vectors got aligned, the company worked a lot better.

   15. HSHarry Stebbings34:00

       (laughs) Sorry. I'm still laughing about that Collison tent.

   16. BHBrian Halligan34:04

       (laughs)

   17. HSHarry Stebbings34:04

       (laughs) Uh, I mean, that really is, uh, an interesting one. Um, I, I, I think, you know, we mentioned that kind of my directness in terms of my feedback. And then I, you know... I, uh, you mentioned listening to the Scott Show from Atlassian. I speak to you. And I honestly look at other CEOs, read about other CEOs, and go, "I should be like that. I should be like that." And you said before, you know, "Be yourself." Well, actually, I think it was Ernest Hemingway, to be fair. (laughs)

   18. BHBrian Halligan34:32

       (laughs)

   19. HSHarry Stebbings34:32

       He said, "Be..." (laughs) Uh, you know, plagiarism is a friend unless you're Bill Ackman. Uh, "Be yourself 'cause everyone," (laughs) "because everyone else is taken." Um, did you always know the leader that you were? And can you take me to a time where maybe you didn't?

   20. BHBrian Halligan34:51

       I still don't, Harry. Uh... I still really don't. Um, one, uh, yeah, one thing I've learned about CEOs, they're all very, very different. And there isn't one model or one formula or one background. I've tried to look at different CEOs and come up with a rubric of, like, "This is what you look for. Here's the five questions you should ask a founder to tell if they can scale as a CEO." I haven't come up with

9. 35:23 – 40:17

   Founder vs. Professional CEOs

   1. BHBrian Halligan35:23

      that yet. In my... I had, I had, um, three CEOs prior to starting HubSpot that I worked for. One of them was an inspirational sales leader. One of them was a very detailed, uh, finance venture type person. Another was a product visionary. They could not have been more different in background and demeanor and leadership styles. And I ti- I tried to take the best from all of them. But I was just struck as I looked back at how different they all are. So I don't think there's (laughs) like, a playbook or criteria that this is what a CEO should be like. I'll tell you another story, Harry. When we had about 20 employees, I joined a CEO group. And by the way, if you're a CEO out there, CEO groups are incredibly helpful. And I joined one in Boston. It was called the High Growth CEO Group.And there were nine members of it, and they were looking for a tenth. And I interviewed to join, and I largely wanted to join because one of the members was a guy named Colin Engel, and you wouldn't have heard of Colin, but he started iRobot, the Roomba vacuum cleaner.

   2. HSHarry Stebbings36:35

      Oh.

   3. BHBrian Halligan36:36

      And I would describe my relationship with Colin in, in two words, man crush. (laughs) I really thought he was amazing. Uh, he was an MIT guy, started a company, it was public, it was a high-flyer at the time, and I just wanted to learn from him. And I, and, and, and there was another guy on there that had started a company called E Ink, called Russ Wilcox, and that was another high-flyer that you wouldn't have heard of, but they made the screens for the Kindles when the Kindle was first out. So it was on fire. And then there were a bunch of other CEOs of other kind of random companies. But I really liked those two guys. And seven of the CEOs were hired gun CEOs from the outside, kind of been there, done that, and two of them, Russ and Colin, were founders. And I remember at the time, 20 employees in, I wanted to seem like a CEO, I wanted to act like a CEO, and I wanted to be, you know, central casting. And what I noticed in those meetings was two of the companies were incredibly successful, seven were kind of going sideways. The two who were successful were founder CEOs, and those founder CEOs were really frigging quirky. Like, super quirky guys. And they're great, and the other guys acted like CEOs. And I was like, "I'm quirky inside, maybe I can just be quirky like these two." And so I tried to start being myself after that, and it paid off. Uh, trying to be (laughs) somebody else has a lot of overhead to it.

   4. HSHarry Stebbings38:03

      (laughs)

   5. BHBrian Halligan38:03

      Um, those two had a big influence on my career.

   6. HSHarry Stebbings38:05

      (laughs) I, I love that.

   7. BHBrian Halligan38:07

      Yeah.

   8. HSHarry Stebbings38:07

      And, uh, I totally agree with you on the quirkiness. I think, I think that-

   9. BHBrian Halligan38:10

      By the way, I'm just gonna ... I, I'll save you the wary of your wording. Like, are you quirky? You're quirky. (laughs)

   10. HSHarry Stebbings38:15

       Me?

   11. BHBrian Halligan38:16

       Yes. (laughs)

   12. HSHarry Stebbings38:17

       I am not quirky. (laughs)

   13. BHBrian Halligan38:19

       Yes, you are.

   14. HSHarry Stebbings38:20

       Uh, I, I, I do want to learn from you though, (laughs) and kind of start at the talent funnel. Hiring is something that I would say is my biggest weakness, honestly, actually, Brian. I have ... I hire amazing people, but I have a low hit rate. (laughs) So like 50% work out, was the review that we had. I hired 10 people in the last three months, five stayed in three months. Um, what are your biggest lessons on how to hire the best talent, and, and what would you advise me?

   15. BHBrian Halligan38:51

       Okay. One of my biggest lessons is that's about right. I used to beat myself up when we'd turn someone over, but I think most scale-ups aren't that good at hiring. Um, and I think there's a fair amount of luck involved, and have ... They don't have a great hit rate. Um, I think 50% within the first year and a half is close to what most companies are in scale-up mode. It sounds a little high for where you are, you're a smaller organization, but at HubSpot, if we turn someone over a year and a half in, we definitely beat ourselves up, and, and like all that. But when I talk to our peer companies, it's kind of ... It's high. Like, there's a lot of turnover.

   16. HSHarry Stebbings39:32

       What are the biggest hiring mistakes you made? I'm a big one for falling for logos, one, and then I also am impressed by ... This sounds st- stupid, but like big words and smart thoughts, and I don't often check the foundational skills enough.

   17. BHBrian Halligan39:49

       Okay. I would kind of frame it a different way, um, from the logo per se. I ... My analogy for being a founder CEO, trying to go from startup to scale-up, is it's like you're climbing a mountain, and it's very icy, and there's like an ice cliff in front of you to get to the top. And I think what ... And you're trying to ... You've got your pick, and you're going up the mountain,

10. 40:17 – 59:25

    Choosing Effective Board Members

    1. BHBrian Halligan40:17

       and it's treacherous. Uh, and most people fail, and there's a reason they fail. It's really hard. Um, and where I think people fall down in hiring, and they h- when they're hiring board members, they're hiring tech team members, it's not just the logo, it's ... What you want is somebody who's three years up the ice cliff from you, who's struggled through that same path. What you don't want is someone who's 10 years beyond it, or even worse, somebody who's never really climbed that ice cliff, they started their career on top, and stayed on top. And so it's not just the logo. Like, I think it's okay if you hire someone from a much, much bigger company if they have u- climbed up that ice cliff, and they have seen the lessons. And I'll, I'll give you a great example for HubSpot. Um, we hired a board member a long time ago whose name is, uh, Jay Simons. And Jay was the COO at Atlassian. You had the Atlassian founder on your podcast.

    2. HSHarry Stebbings41:22

       I know Jay well. I had Jay on. He's a-

    3. BHBrian Halligan41:25

       Oh, he's good.

    4. HSHarry Stebbings41:25

       ... absolute legend.

    5. BHBrian Halligan41:26

       Yeah. And he was ... He still is on our board. He was three years ahead of us on the ice cliff. And, you know, HubSpot's whatever, two point something billion, uh, revenue. They're four-something in r- They're a few years ahead of us on the ice cliff. He had just seen everything already. So he's on the board, we're having an issue, he had just solved that issue or just dealt with that issue. And so that recent relevance was incredibly valuable. And so that's what I would encourage. And so like HubSpot's hiring today, we're looking for a board member. I'm pretty skeptical of hiring someone who's been at Google a long time or Microsoft a long time. But if I'm looking for someone who's at ServiceNow or Intuit and ... Yeah, that's pretty interesting to me. So I'm looking for somebody a few years ahead of us.

    6. HSHarry Stebbings42:10

       Would you hire someone if you had reservations about them? I'm asking specifically, I'm, I'm hiring someone potentially now, and I'm like, (sighs) "I do have concerns." But I n-

    7. BHBrian Halligan42:20

       I don't think I ever hired anyone where I didn't have some concerns. There's always red flags.

    8. HSHarry Stebbings42:26

       And you just got over them? How often did those red flags materialize versus they didn't?

    9. BHBrian Halligan42:31

       They usually did.

    10. HSHarry Stebbings42:33

        Hmm.

    11. BHBrian Halligan42:34

        They usually did. Uh-

    12. HSHarry Stebbings42:35

        You mentioned, you mentioned, you mentioned-

    13. BHBrian Halligan42:38

        Yeah.

    14. HSHarry Stebbings42:38

        ... the quirkiness. Yes, I'm quirky too. I also work really hard and I drive a very intense culture of hard work.

    15. BHBrian Halligan42:47

        Yep.

    16. HSHarry Stebbings42:47

        That's not very popular in modern society with younger people. D- how do you think about, like, founders who are quirky showing their quirkiness in hiring? Do you know what I mean? I don't want to put people off by being too quirky up front.

    17. BHBrian Halligan43:03

        I think you have to be yourself. You have to be, you, you have to shave off a little of your hard edges probably. I had to definitely shave some of mine. But I, I was very much myself. And I think it attracted a certain type of people, and it definitely repelled a certain type of person. Like, you spent your career at McKinsey, you come in and interview with me, you're probably not that interested in working for me. You're probably not. (laughs) Uh, and that's fine. Um, now, I think you can fall in a trap where everyone's similar, but, um, I think you, I, it, when you're h- I would be surprised if anyone you hired didn't have some red flags. Um, yeah. I would be very s- Everyone that we hire it's like, "Well, they've got some strengths and some weaknesses." I think where people, I think where s- scale ups fall down on hiring and founders fall down on hiring is you've got, (laughs) you've got a panel of people who are interviewing ex, eh, eh, a VP from, for, of whatever, of product. And you've got 10, eight people interview them. If, if you've got candidate, first candidate Mary gets four, four out of ten, four out of fours, and gets four, two out of fours, and so it's mixed. And then you've got Jane who's got eight, three out of fours. You always hire the Jane. That's all, (laughs) that's just always happens. You always hire the Jane. I think you're better off with a Mary. And you want, kinda, spike, a spiky team with some people who have great strengths and great weaknesses, and you want a spike in different directions. Uh, I don't f- I think you want to avoid that lowest common denominator type of hiring.

    18. HSHarry Stebbings44:49

        I always actually say that to LPs. A lot of LPs ask me about manager selection. And I say like, "You should invest in the ones where it's like, they were terrible, they never responded to an email. But they also had Brian saying, 'They transformed my company and I couldn't have done it without them.'" That's an manager I wanna get behind.

    19. BHBrian Halligan45:06

        Yeah. I get pretty irritated though, I do think it's a signal if people take three days to respond to your email. I think that's a, a big r- that's always been a big re- red flag for me.

    20. HSHarry Stebbings45:15

        Do you think speed of response is a feature and not a bug?

    21. BHBrian Halligan45:18

        I do.

    22. HSHarry Stebbings45:20

        How do you manage it though, Brian? Like, I mean-

    23. BHBrian Halligan45:23

        Okay, this is the ironic part, 'cause I'm not that good at this. So, I, uh, I, we were just talking about, like, reflection. And I don't do, um, New Year's resolutions. But every quarter I do a quarterly plan. So I kinda grew up in sales so I, the sun rises and sets in the quarter for me. So I just wrote my quarterly plan, and I typically get about half of my quarterly, I've got like six or seven items on there. Um, and so I sit down and do those quarterly plans. Now, the tricky part with working with me is if something's not on my priority list or my quarterly plan, (laughs) it could be weeks or months before you get a email response from me. But if you happen to be engaging me on something that's on my quarterly plan, it'll be s- I'm, I'm back to you in half a second. Uh, so I probably am, I, I would, I would be, I, I, uh, yeah, there'd be red flags. If I were hiring me, I would have some red flags on that. (laughs)

    24. HSHarry Stebbings46:18

        Okay. So we have some red-

    25. BHBrian Halligan46:19

        Here's another thing I would say about prioritizing, Harry, is I think too many people run their life through Slack and through their email. And that's everyone else's priority list imposed on you. And so you're really just spending your whole time working on everyone's to-dos. And you have to do some of that, of course. And people just don't spend enough time like, "Well, what am I trying to get done this month or this quarter?" Or whatever it is, and like have their list and like, "I need to make progress on my list today, not just be responding to everybody else's emails." Uh, I think the way email and Slack and text works is you're just very reactive.

    26. HSHarry Stebbings46:52

        Brian, what's on your list today? You're not CEO of HubSpot anymore.

    27. BHBrian Halligan46:56

        (laughs) Okay. You want to know?

    28. HSHarry Stebbings46:59

        Yeah.

    29. BHBrian Halligan47:00

        My list today or this quarter?

    30. HSHarry Stebbings47:03

        Y- you choose.
11. 59:25 – 1:15:53

    Sequoia Meeting Insights

    1. BHBrian Halligan59:25

       VCs and got 17 nos in a row. Our last meeting was a guy named Jim Goetz. Jim Goetz is kind of a legendary, uh, VC at Sequoia. So I remember I was... Dharmesh wasn't with me this time. I'm sitting in a conference room and, uh, I was nervous. You know, it's Sequoia, it's like the center of capitalism, sweaty palms, sitting there waiting. Jim's kind of a legend. And Jim walks in, and as I'm shaking his hand, like my hand is moving up and down like this, he says to me, "Hey, Brian, what's it gonna take for Sequoia to own a piece of HubSpot?" And I said, "Really, not much. Just give me a term sheet, I'm ready to go." (laughs) I had no other options. (laughs)

    2. HSHarry Stebbings1:00:00

       (laughs)

    3. BHBrian Halligan1:00:03

       Uh, and so Jim kind of shook my hand. We spent a bunch of time with Jim, and then he handed me off to an up-and-coming partner named Pat Grady, who I think you know.

    4. HSHarry Stebbings1:00:11

       Yeah.

    5. BHBrian Halligan1:00:11

       And super nice guy. And I thought we would have a term sheet and we'd be done in a week. And Pat spent the next three months going through unit economics (laughs) , going through just every line of every spreadsheet. And I'll tell you one funny story about Pat. So we're in Boston and he wanted to talk about how we calculated CAC or something. By the way, during the time he dug through all that, he- he- he figured out we were calculating unit economics wrong and he got our head straight on our pricing model. He fixed a bunch of stuff during that. But I thought Pat was gonna say no as he went through all this. But my Pat Grady story is, and I think this is part of why Sequoia's successful, is he texted me and he said, "Hey, you got time tomorrow at 10?"And I said, "No, I'm tied up at 10:00. How about 11:00?" And he's like, "No, I can't do 11:00." He said, "How about 9:00 your time?" Said, "I can't do that." He said, "How about 7:00 your time?" And I said, "Well, (laughs) I'm usually just waking up, but sure." And then I thought about it, 4:00 in the morning his time. (laughs) And I was like, "Pat, do you have a life?" Anyway, we had that meeting. Pat was incredibly helpful and Sequoia was incredibly helpful, sort of rethink our pricing model and our unit economics, and really got us on a, a good path. They were, they were really good. But that was the process with Sequoia. Handshake with Goetz really was engaged. Pat dragged us through the mud, eventually got to yes, and then we did the deal.

    6. HSHarry Stebbings1:01:41

       To what extent do you think Sequoia is a needle-moving event when they invest in your company? You know, a lot of people say, like, "Oh, it's really all down to the founder. I mean, at the end of the day, cash is cash. And sure, it helps a little bit with brand, but whatever." Or is it actually, no, it really is a seismic help?

    7. BHBrian Halligan1:01:57

       For us it was huge. It was needle-moving, big need- it was a big n- one of the biggest needle movers. It was... The brand was huge for us. Um, they helped us with our business model a lot, pricing model too, their network. They do something or they did something cool back then, they called it the Sunrise Tour. So once they make the investment, they invite the leadership team to come, just meet everyone in the Sequoia community, all the right people at LinkedIn, at Google, at you name it. And so like, bam, your network gets three times bigger when they become an investor. Uh, so they were, they were kind of huge for us.

    8. HSHarry Stebbings1:02:38

       (laughs) I love that Pat, though. I always do calls with him. We, I think we have like a monthly call, and it's always at, like, 5:00 AM and he's already done a workout, and I'm like-

    9. BHBrian Halligan1:02:47

       Yep.

    10. HSHarry Stebbings1:02:48

        ... "What the fuck is wrong with you?"

    11. BHBrian Halligan1:02:49

        Yep, he's a machine. He's a machine.

    12. HSHarry Stebbings1:02:50

        He's an ab-

    13. BHBrian Halligan1:02:50

        I think they all are, by the way. (laughs)

    14. HSHarry Stebbings1:02:53

        Is that what you think makes them successful? You've worked with them for years now. What, if you were to say what makes them successful? Are you an LP in them? I know I-

    15. BHBrian Halligan1:03:01

        Yeah.

    16. HSHarry Stebbings1:03:01

        ... I am. Yeah, so we both are.

    17. BHBrian Halligan1:03:02

        Yeah.

    18. HSHarry Stebbings1:03:02

        What do you think makes them successful?

    19. BHBrian Halligan1:03:06

        Okay, I know them quite well. Uh, I think there's a network effect in the venture business, of course. So they have an unf- unfair advantage in that they did LinkedIn, they did Apple, they did all these companies. So they have that network and they have all that knowledge, and they have that brand. And so... In some industries, brand's more valuable than others. It's very valuable in ventures. So that, of course, is given. Where, where I think they're special is they don't take any of that for granted. Um, so there's a whole new crew over there that runs it, Pat and Rudolf, and they're paranoid. They don't want to lose that mantle. They know they have something fantastic that Moritz and the rest of them gave, Doug Leone gave them. And they work, like, really work h- so... I- they work much harder than any other VCs I've come across, and they're absolutely paranoid that they're going to lose it. They're also... (laughs) There's something in their genetic code where... I think this works for them, but it can be depressing if this is in your company. They don't celebrate their successes. They beat themselves up for their failures, really beat themselves up for their failures. And I think they kind of dwell on their failures and they don't want to repeat those failures. I th- I think, I think there's something in the culture there that will sustain that competitive advantage, at least through this generation. It's very... The, the current crew is really good.

    20. HSHarry Stebbings1:04:34

        I, I, I think the current crew is fantastic.

    21. BHBrian Halligan1:04:37

        Yeah.

    22. HSHarry Stebbings1:04:37

        Um, I agree with you also on the work hard. I've, I've never seen ethic like it.

    23. BHBrian Halligan1:04:42

        Yeah.

    24. HSHarry Stebbings1:04:42

        Um, (laughs) fucking love Doug. (laughs)

    25. BHBrian Halligan1:04:48

        (laughs)

    26. HSHarry Stebbings1:04:48

        Uh, anyway, uh, can I ask another slightly personal one? But I heard that Sequoia bought some stock off you-

    27. BHBrian Halligan1:04:55

        Yeah.

    28. HSHarry Stebbings1:04:55

        ... and it was one of the most costly, uh, mistakes you made, bluntly. Can you take me to that? Why you sold, and just the decision-making for you then.

    29. BHBrian Halligan1:05:05

        Yeah. It was our series D. It was, uh, I forget how much they invested, 40 c- 40 million, 250 million valuation. Like I said, if they didn't do it, every, all 17 other VCs had said no. And so we were very grateful they did it. Uh, and when they were doing it... Okay, it was a complicated round because salesforce.com invested and Google invested. This is before they had like big venture arms. Uh, and so there just wasn't a lot of room in there, and they came up with a, I thought, a clever solution, which was, "We'll buy some of the, the exec team and founder shares," um, which is very common today, of course, buying secondary. It was, it wasn't back then. And so they bought it, and if you think about that, I sold some shares at a $250 million valuation. Now the company's worth 100 times that. Uh, but I would also say I don't regret it. Uh, at the time, I don't know how much it was. Call it a million dollars. Relative to my current net worth, it was very much a life-changing event. Um, and so people think about the time value of money, the time value of money, and they think about, okay, you can get a 10% return on it. That's not how I think about it. Like, a million dollars th- then was so much more valuable to me than today, let's say. And so it was very valuable to me. It was very valuable to Sequoia and it was smart of them because they were nervous we were going to s- uh, sell to salesforce.com. Salesforce.com made an investment. They did not... They were not thrilled about that idea at the time, um, because they were worried Salesforce would come in and buy us at whatever, at, at 2X and, you know, Sequoia wants to make it 10X. Um, and so they come up with that clever solution, and I think it worked for them because it gave us a backbone. It, it, it in- and it moved our horizon from like 2 years out to like 20 years out, and really let us plan for the long term and have a st- a strong backbone if someone did come in and want to acquire it. So I... It worked for both of us.

    30. HSHarry Stebbings1:07:04

        What advice would you have for founders who are considering selling some secondaries?
12. 1:15:53 – 1:19:59

    Worst VC Meeting Ever

    1. BHBrian Halligan1:15:53

       a real ocean climate fund out there, and I wanted to have an impact on like, that's where I'm gonna spend my money. And so we've become like a magnet. If anyone's got an ocean tech startup, you know, they come to us. Um...

    2. HSHarry Stebbings1:16:06

       Final one before we do a quick fire. You mentioned like 17 VC meetings, 17 nos. What was the worst VC meeting you had?

    3. BHBrian Halligan1:16:15

       Okay. (laughs) Uh, it's with a firm here in Boston, a storied firm, and it had a storied founder. And, uh, we had pitched one of the partners several times, a guy Jeffrey, and he was interested, so we came in for the full partner pitch. And the founding partner was a little rough, and he, anyway, he sat next to me. I hadn't met him. He's kind of a legend. And I've done a lot of venture pitches. I had it down. Let's just say I'm lively, you know, in the pitch. And he fell asleep. He fell fucking sound asleep during my pitch. (laughs)

    4. HSHarry Stebbings1:16:59

       (laughs)

    5. BHBrian Halligan1:17:01

       And they sat next to him and I kind of nudged his chair, woke him up. And so we finished the pitch, and I remember Dharmesh and I looking at each other, "Well, I guess we're, that's, we're not getting a term sheet from these folks." And then ironically, they went away and came back and gave us a term sheet. Yeah, I was like, "Oh, that's strange." And then we got the term sheet, Harry. And, um, it came through fax, this is a long time ago, and we got it, and I quickly looked at it. I was like, "Oh, it looks decent." Sent it to my lawyer, and within five minutes, my lawyer called me, which is, was unusual. And he said, "Oh, I saw the term sheet." And I was like, "Yeah, how's it look?" He's like, "Did you see the pool?" And I said, "I, I didn't really take a loo- Remind me what the pool is again," is what he said. (laughs)

    6. HSHarry Stebbings1:17:47

       (laughs)

    7. BHBrian Halligan1:17:47

       'Cause it was our series A. Uh, he said, "Oh, you know, it's the amount you're, you're holding aside to hire people." He said, uh, "Did you see the size of it?" I said, "No." He said, "It's 22%." And I said, "Okay. Is that normal?" He said, "Seven or eight is normal. 22's a lot." He said, "Why don't you call them and ask about that?" Hung up the phone, called Jeffrey, and I said, "Thank you. By the way, thank you for the term sheet. Very surprised we got it after the fi- (laughs) after the founder-"

    8. HSHarry Stebbings1:18:20

       (laughs)

    9. BHBrian Halligan1:18:20

       "... firm fell asleep, but thank you. Just out of curiosity, why is there such a large pool?" He said, "Well, just in case we need to replace the CEO." I was like, "I'm the CEO." (laughs)

    10. HSHarry Stebbings1:18:34

        (laughs)

    11. BHBrian Halligan1:18:34

        "When, when were you gonna tell me that you were planning on replacing me?" He's like, "Well, there hasn't been a good time up until now, but why don't we talk about it?" So that was a bad, that was sort of a bad (laughs) experience for me with the founder falling asleep and, yeah, they wanted to replace me.

Episode duration: 1:26:38