Building HubSpot to $30 Billion Through Culture | Full Interview

How long had you been CEO and obviously founder, but before the snowmobile accident and what were you thinking before the snowmobile accident? What were you thinking after? And tell us all about it.

So I was Huntpud CEO for 15 years, and I was snowmobiling one day and I basically went off the cliff. My son was driving and that's kind of the breaking the gas backwards and hit the gas at the wrong time. We went up over the lip and just, just lost gravity. I just, I remember going over and just like, oh, my God. And then, you know, your brain just gets shut up. I don't remember flying down, a mile down, smashing snowmobiles in a thousand pieces. We were in a thousand pieces. And I remember sitting there like, I get out of this thing. I'm going to make some changes.

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All right, so this week we have my friend Brian Halligan, who is the executive chairman of HubSpot and is the founder and was the CEO for 15 years before stepping into the exec chairman role. And Brian, in addition to being the father of inbound marketing, you know, is also just an amazing leader. He's a CEO coach now and you know, it's not his career that makes him interesting, even though it's incredible. Founder of a climate change firm, professor at mit, senior advisor at Sequoia. It's that he can kind of look into your soul when it comes to leadership and just help. And he's got this incredible piece of writing. He's written a couple of books. Huge Grateful Dead fan, but he's Written.

A couple huge, huge. Deadhead.

Deadhead, Deadhead.

I think he'd be upset if we left that off the resume.

I agree with you. I think he's been to like hundreds of concerts, hundreds of Grateful Dead concerts, but then most recently just published this thing of everything he's ever learned from leading at HubSpot. And we have a goo guys shout out in there.

I mean crazy. And like his journey is the, the near death experience.

Oh yeah. The real kinship with you, Alex, which was amazing.

Like, I mean, just to think about his journey and like what you said, like, it's one thing to see it all on, on paper, but like the person he is and like, you know, at this end of it now he's coaching CEOs, which I think is freaking amazing, you know, because like who. There's not many people that are actually qualified to do this stuff.

And.

And this guy. This guy's one of them.

Alex. I just thought about this. We talk about this a lot. He might be, he's. He's kind of a modern day Bill Campbell. Right. If you really think about it, I think that that actually might be the reason he's so cool. He's kind of, you know, this generation. I don't know. I think he's on his way.

Do you think he'll call himself a glue guy?

I think as you pointed out, you know, it's hard to be a self proclaimed glue guy. But I hope he starts to embrace that because I think, I think he's a glue guy for leaders and a glue guy for people. I do.

I couldn't agree more. I hope that people realize that like being glue guy doesn't mean you have. You can still be like to your point, Shane, like you can be the leader, you can be the star and still be a glue guy. In fact, I think the best teams. That's the case.

Love it. Onto our conversation with Brian.

How are the glue guys doing?

Great. Thank you for joining us, Brian. We appreciate you, man.

We were very happy that in the halogenisms that, you know, kneading glue guys showed up and we were wondering if that was a recent addition or if that's something you always had.

It was a recent addition. I had. I. Well, Robbie told me about podcasts, of course, and I've been listening to really enjoying it. You guys are terrific. And it was a recent addition. But it's true, I think of like in HubSpot, like your head of sales is kind of the star of the company and closing big deals and posting big numbers but as a company goes from like startup mode, like hundred people to scale up more than a thousand people, the leverage really shifts to the glue guy or gal that works for that head of sales. And the glue guy can keep the whole complicated system in his head and moves all the knobs and dials around, allocates the resources wisely. That's kind of where the leverage shifts and startup from startup to scale up mode. And we had a couple at upspot that I wouldn't be sitting here on this call without.

I think it's funny because in the sports world, it's no different. Like, these guys that are important in the building sometimes aren't the same people that, that, like the media or fans think that are important like that. Again, to go to the stats, like, fan. Just especially today, like with fantasy sports, all they do is see the stats and like, hey, think and think that these guys are important. And those aren't necessarily the people that are celebrated as important inside the building or that have the biggest. Are the biggest contributors to culture and like the, the backbone of a team or like the soul of the team. And so it's funny, but, like, in buildings, they are celebrated. Right? Like, you're in Boston, like Matthew Slater, the longtime Patriot. Like, I mean, he was the backbone of that team.

Yes.

And you'll never hear him get. I do TV for a living. You'll never hear him get talked about on TV by like, national media like that. But, you know, he certainly was a guy like, I think the longest captain ever in Patriot history.

Yeah. You know, one of the nice things about me and Boston is we won a lot of championships and had a lot of teams.

Here we go.

Yeah, I know a lot of we there from the guy who, you know, is the founder of HubSpot, talking about the Boston sports. Okay, fine.

I get asked a lot about this, about sports fans, and everybody thinks Philly fans are the worst. Everybody thinks, like Raider fans are the worst. And I universally, definitely it is like Boston fans, Patriot fans, the worst. And, and it's just the fact that they've been so spoiled with six freaking titles in the last 20 years. Like, if, if they were bad, I think everybody would universally know them to be the worst fan base. Just my just one man's opinion is.

That the Boston Celtics won the. Recently won the championship. And I feel like the team is kind of. I think it's a glue guy team like Al Horford, Drew Holiday are like really, really glue guys. And even Tatum, who's, you know, front and center, he Wasn't shooting well in the championship, and he just rebounded and passed. He turned out to be, you know, he put his ego aside and kind of did the blue guy thing in the championship. And I think championships are won by the blue guys as much as the stars.

It's funny you say that. We text about that team a lot. Ravi especially.

I dislike the Celtics intensely, but I like that team. But because I think Jrue Holiday, Derek White, Al Horford, those guys are. They're amazing. They're amazing. So, Brian, you know the thing you didn't. Board meetings. I'm not going to text you. I'm going to tell you. You supposedly would bring in like, eight or 10 people from the company into the board meeting and have people in the board see them. And that's not like bringing in one person from the company or bringing in, like, I have the executives there every time. It was like a rotating cast of people that were really good and impactful, and all of a sudden you'd bring them to the board meeting, which that is unusual.

The other thing we do in board meetings that's great is we have customer panels. So we get a board meeting next week, San Francisco. We get a panel with five customers on. There will be an hour and 15 minutes, and the board members can ping them with questions and, you know, really get in there with them. And I love. That's my favorite thing we do every management team meeting, every company meeting, we have customers come and talk. I thought that. I have found that to be. I did a lot of stupid things at HubSpot. I think that was one of the smarter things I did.

What's the most interesting thing you learned from your customers that you didn't know or maybe overthought or underthought?

The first thing is, like, they would come in and unless they were well coached, they would definitely blow smoke up your backside. And so it would take a few questions and some prodding for me to be brutally honest with us. We're not here to hear the good news. That's certainly one thing we heard. And every time we do it, we hear about big problems, either in our contracts or the way our processes work or where a product works or part of a product we thought was great, wasn't great. We learn all kinds of stuff. And they'll come this time and be like, okay, we have all this new AI functionality in a product. Are you using it? Is it working? Do you like it? What's missing? What do you see around the corner?

It's fabulous for Us one thing that's crazy about that. Brian, I was just thinking as you were talking, it's weird. Like customers of HubSpot, if you think about it, like, they have the power. Right. You know, they are the customer, yet even they, in a moment where they are asked just like, human nature, their nature is to be nice and not give you the feedback. And they're in like the power position. Right. And it actually goes to like, think about the. How hard it is for someone who's not in the power position to ever tell you the truth about something you need to get better at. Just human nature wise. We so badly want to be like, liked that even when you're the customer. Right. Your first reaction is like, let me just tell you the good stuff. So you really have to dig for feedback if, especially if you're in any position of power.

And it was very much the case for us. Like, we would do 360 degree reviews of our employees once a year. And mine would be very rosy because people would, you know, you know, they would want to tell me what I want to eat. People would tell me what I want to eat.

And you're perfect, as we know. Yeah.

Anyway, this one year, my co founder, Dharma, I said, hey, can you just do the review for me? Instead of like a normal process. So he did a survey of like 20 of the employees, the tech team, the board, some customers. And he asked him two questions. First question was, on a scale of 1 to 10, how likely are you to refer Brian as CEO of HubSpot? And the second question was, why did you give that answer? And people wrote novels, like novels in the comments. And. And then he collated it took him a while. And he gave me the report. The front page was like my results and the kind of a histogram of my scores. And then it was a long report and I was going through it, I was on page 10, and it was like each page was a feature. Like, Brian's good at explaining what HubSpot is. Brian's good at setting the tone on the culture. And then he would take quotes, direct quotes, and like paste them in. So it's really like, oh, okay, really get it. And like, I'm 10 pages in. I'm pretty sure I was the best CEO ever. Page 11 came and that was the bugs. That was the first bug. And there were 11 pages of bugs after that. And I don't drink scotch. I'm not like a brown liquor guy. I remember at the end of it just thinking, I'm so bad at Being a. I drank 2 inches of straight down the scotch. Deepaks of breakfast of champions.

A couple thoughts on that. Like, I can only imagine. And Shane, you could tell me this. Like, if a coach did that, by the way, was it anonymous?

Yep.

Okay. Like if you. I could not imagine a co. Like if a head coach did that exact same thing. First off, you're totally right. Like you're never going to make everybody happy. There are going to be a certain amount of people that don't feel like they're being utilized.

Right.

Or don't mesh with your. Your style and are going to be pissed off about it. Right. Like, and I also think that the objective is to not necessarily, necessarily be liked. Right. From a head coach. Right. Like, that's not that the, that's not what you're there to do is to, you know, obviously be liked by your employees. Like, certainly you want to build healthy culture and if there's things that are very glaring. But I so like, I don't know how I feel about that. Like, certainly as like the starter I could be like, oh, this coach is awesome. The backup quarterback probably like thinks this guy sucks. I'm better. Why isn't he playing me? You know? And then so how objective were you like with that? I guess as you got like, especially even some of the bugs, like, I mean, I like, you kind of have to take it with a grain of salt. Right. Like again, there's going to be disgruntled employees at any company, certainly of scale.

We do it every year. It's paintball every year. I post posted on the wiki so everyone can see it in the company. And my reaction to it the first couple of years was to try to fix my bucks. I think it's natural. And then over time, like, the same bugs would show up every year. And like if I put a dollar in, a dollar's worth of calories into fixing a bug, I might get a dollar and one cent out. But like, I found that if I focus on my strengths and lean into a strength and I put a dollar into a strength, I could get 10, $10 out. Like just much more leverage. And over time, I kind of gave up on fixing my weaknesses and just tried to hire around all the weaknesses and that ended up working for me. I think the conventional wisdom is fix your bugs, but for me, I just live with them.

Brian, do you. Can you give us some examples of what some of those bugs were just like, you know, what were people saying you needed to get better at?

I can just be very Passionate about things and excited, and I can push people pretty hard. And I'm aggressive, you know, Like, I really want to win, and I'm not really the guy. I'm, like, I'm out front and I'm pushing and some of that aggression, some, like, pushing and, you know, that's not good enough. Like, I pushed pretty hard, and I got a lot of feedback. It turns out people didn't like that.

You got told that passion was a negative, a bug.

I think some of my features were also bugs.

Do you think there's something to the fact that you said, like, everybody, all the. There's an employee review, right? So all these employees are doing a review, and that here is the head of the company. The founder is stepping up and doing his own review and making it public. And do you think, regardless of what you did with the bugs or the features, like, do you think. I think that there's, like, power in that example, right? Like, as a tone for the company that, like, no one's above this. We all need to get better.

I don't know for sure. That was my plan. Like, so I would post the entire 20, 21 pages, and then I would write a one page, like, my plan for the year. And I remember one of the years was, Brian's got to grow up and be the leader. HubSpot needs to scale to the next level. That was sort of the title of it. And then I had, like, here are the things I'm working on, and the only ones, like, here are the bugs I'm going to fix. The later ones are, here are the strengths I'm going to make better. And I. I got to believe that some of the people saw it and said, if he's working on himself, I should work on myself.

What'd your board say? Your board say this is, like, not the strong, you know, Spartacus that we. That we need. Do they appreciate that? I mean, did you ever get questions in board meetings about, are you sure you want to show everything here?

Yeah, I gave it to the board. They all got the full report. I don't know if they read through the whole thing. They got my summary, and then I would report out to the board on it every year. And I think the transparency built trust with the board, and I think the transparency built trust the employees. I think that maybe some of the board members thought it was weird, but I'm a little weird. Fine.

Right on that. One of the things you wrote about in the Halliganisms, which I'd recommend everyone read, you know, all the lessons you've learned from, you know, building HubSpot and then also being the exec chair. You talked about imposter syndrome a lot in there. Or you talked about it in there, and you sort of made this very interesting thing of, like you said, you still feel it, right? You know, you're a successful company. You're like, I feel weird writing this right now. And, I mean, you look like you're 35, but, you know, you're older than that. So I think to have. To have the imposter syndrome. How did you have the imposter syndrome and still feel comfortable being yourself? So what I mean by that is, if a board member is telling you to do something, if employees are telling you to do something and you have imposter syndrome, how did you still have the strength to kind of just do it your own way when you. In the back of your mind, you're kind of like, I don't even know what I'm doing. Do you see what I'm saying, Ravi?

You know, when I really feel imposter syndrome, I like the most in this.

Equoya partner meeting right now.

Like, I'm on the podcast.

Join the club, Ryan. You and me both, brother.

Yeah, trust me, all. All 20 of our listeners aren't okay. They're shooting. They're shooting this podcast to, like, you know, Pluto, to see if there's any intelligent life. That's what this podcast is being used for. All right? So don't worry about that. My mom is not. My mom is not worried about you, Brian. She's really impressed by you.

Okay, I will tell you about the sort. So I do still have imposter syndrome. I'm not kidding about, but I would say in terms of, like, being. I remember it was like, two years in the HubSpot, I joined a CEO group. And I don't know if NBA teams do this, but, like, it's a group of startups that are scaling 10 CEOs, and you meet once a quarter for a day. And eight of the CEOs were kind of central casting. They looked like CEOs. They sounded like CEOs. Like, that's what I should be. I should be just like those guys. And then one of them was a guy named Colin Engel, who. Who started iRobot, which makes the Roomba vacuum cleaner. You guys might have the Roombas. And the other was a guy named Russ Wilcox, who. He made the glass for the Kindle. This is, like, long time ago. And I was trying to be like, the other eight and it was. These two were. They're quirky, really quirky guys. And then we got to see each other's service once a quarter. I look at everybody's summers, and the two quirky guys were crushing it. And the central casting CEOs were kind of with it. And I. I remember at one point I. I had a conversation with myself, like, why am I trying to be like those guys? It should be like, Russ, it should be light calling. And I. I'm a little quirky, and I'm like, I'm just gonna be myself, like, whatever. And people will put up a bit. And it turns out they were willing to put up with it. And it's like, there's a great quote. I forget who did the quote, but, like, be yourself. Everyone else is taken. And so I have tried to be myself more as time's gone on. And just my co founder, for sure, it's himself. He is extra duty quirky.

Those guys are the ones, like, the examples, like, Colin and Russ were, like, good, like, for you, an example of, like. Because you even said it. Like, I think in the face of imposter syndrome, there's nothing better than, like, the balls to just say, like, I'm weird and like. And own it. Right? Like, that's like the exact. That's where you need to be, you know? But, like, those guys, were that for you?

No, Alex, I mean, like, we've all. We've talked about this before on the, on the pod. We've all gone through that. I mean, when you got drafted, number one, you felt like you had to act like Manning.

Yeah, I wasn't enough. Yeah, I got.

You had to be Peyton Manning, you know, And Ravi, I'm sure, you know, when you got into the CEO seat, you know, you're looking around and, you know, you probably talked a little bit different, dress a little bit different. I mean, you may have put on a collar for once.

Dude, I wore a collar every day at Instacart. No, I had to. I had, you know, presented feeling. Now I'm supposed to, you know, dress down a little bit.

Wait, did you guys have imposter syndrome? Shane, did you have it? Did he go away? No.

But in a weird way, it's what drove me. The. The insecurity drove me. Every year. I was. I was terrified. I'm like, this is the year they're going to find out. This is the year. This is the year the curtain's going to be ripped away and everyone's going to say, aha. I knew it. I Knew it. So like that was. I was driven by fear and someone is going to out me as this imposter, this fraud. And I'm national player of the year fraud. I'm 6 pick of the draft fraud. All rookie team fraud, right? And like we talk about, you know, so we talk about these bands of going back and forth between overrated, underrated. You know, I'll never forget when I signed my big contract. I signed a six year, $36 million contract back in 2005. It was, it was the last time you get a six year deal. And there was a quote in the paper, a national paper that said, you know, some would think this, this contract for Badier is too much, but you know what? Sometimes you just got to pay your. And I'm like, I knew it. Everyone thinks I'm a bomb. Like, I'm not kidding. So like I, like I. I reach my dream. I may. I make more money than I ever thought I would make. And like, it's the pinnacle of my career. And I'm thinking to myself, there, there it is. I knew it. They knew I was a bum. And after that, like, I had a guaranteed contract so they couldn't fire me. So like, I was, I was good and I relaxed, but a hundred percent, I was driven, like by imposter syndrome.

And Brian, you know, it's funny, it's always hard to tell stories after these guys because it's like when I was in the NBA, when I was in the NFL, I can be like, you know, when I was at Instacart, you know, but it's funny, you know, you know Claire Hughes Johnson, right?

I know her very well.

So Claire is former COO of Stripe and like very good friend of mine. Sounds like a very good friend of Brian's, but also like mentor or whatever.

She found my board. She is, yeah.

Oh, I didn't know that. Lucky you. I. So Shane, when I got named coo, I. I had to make like a tough personnel decision. Okay. So I called Claire and you just talked about the same thing of like, you know, did you feel imposter syndrome? So I was like, shit, I'm talking to Claire like she's CEO of Stripe. Like, I really look up to her. I'm gonna like, get her advice, but I'm also gonna like, show that I know what I'm doing. So same thing. She's like, I'm like, I have this thing I have to do. Like, you know, she's like, okay, well what are you gonna do about it? So I was like, well, I'm planning on letting this person go, and here's what I'm gonna say. And literally, Claire's response after I went through, like, my talk, she was like, you're not really going to say that, are you? Right. Like, literally that was her response. And I. I thought I was like, you know, ready to do it. And I was like, no, no, obviously not. You know, but then she was.

She.

What she said was, same thing. She's like, what do you actually think? What do you actually think? What do you. Do you think this is a good idea? And I was like, yes. She's like, why? And I told her. She's like, just say that. Don't go through your whole bullshit. Like, just. Just like, say what you think. And I think the same thing of, like, learning from somebody that you really look up to that, like, all you have to do is, like, say what you think that is the best you can do. The best version that you can bring is that she helped me so much, but it took her kind of asking the, like, are you a fucking idiot? Like, are you really going to. You're not really going to say that, are you? So I think you need those kinds of people, you know, as well.

So, Brian. So, like, we all have our stories. I call it get into your game.

Okay?

We finally got to our game. All right? Our game might not be, like, shooting. We might be going to the rack. You know, we're defending, like, but we all got to our game, you included. So talk about how you can help people in your world get to their game. What's the messaging? You know, how do you. How do you get people to focus on what they can do and their capability and their potential and their strengths versus, like you said, I'm not going to worry about mitigating my weaknesses.

Okay? I'll tell you what I'm working on these days. So I'm chairperson, my company, and I started this Climate venture fund, and then I work at Sequoia Capital, and almost everything I do is just coaching other CEOs. I'm basically a CEO, professional CEO, coach, and I have doing as a hobby, and now I just kind of do it and I love it. And it's mostly for startups that are going through the same journey HubSpot went through. And I made a lot of mistakes and I get a lot of joy and I feel like giving something back to the universe for helping me. And I'll give you an example of how I do it. I just got off of college just before this with what I call the kids table.

You should explain this.

So I have two tables. I have the kids table and the adults table. You know what I mean by the kids table? At Christmas, you have the kids table.

Totally, yes.

Anyway, the kids table are companies in Sequoia's portfolio that are between 5 and 50 million growing, whatever, 200. They're ripping in the adult stable, you know, 50 to 500 million growing very fast. And they. And when you're growing fast, you have, it turns out you have a lot of problems and you have, they all have the same problems, the same size. So I, I just got off the kids table, which are, I don't know, eight or nine companies. And half of it is everyone's just complaining about their employees. And the other half are some good ideas and best practices, what people are working on that are kind of helping them break through to the next level. So that, that' of what I'm up to these days is kind of CEO coaching. And I'm, I'm finding it's very rewarding, actually. I like it a lot.

You do, you do these calls together?

Yeah.

So there's, there's some connection in this for them too, right? Like they're not alone in there.

Yes, very much. Misery loves company.

Yeah, for sure. Groups suck.

Yes. It's terrific. And I was in, I was, I, I mentioned I was in the CEO group with Colin Engle, the Irobot guy, and Russ. That was terrific. I was in one when HubSpot was bigger with like the founders of Slack and Shopify and Atlassian and that was terrific too. Great. Great place to really feel like an imposter, by the way, when you're in those groups.

Brian, how do you actually do. If you take what Shane just asked, and I totally get your CEO coaching and I, you know, I, I'm longing for the day that you invite me to the kids in the adults table to like join you as a co coach. But I'm just waiting to see if I can earn that someday. But separately, how do you actually do it? Like, how do you get someone to see what their strengths and weaknesses are and then how do you get them to lean into the strength? Because it is, like you said, natural to try and fix the weaknesses. So what are some of the tactics you use when you're coaching?

Honestly, those calls, I open it up to what are problems people are having and everyone's having problems and they're all having the same types of problems. Like everyone is behind on sales rep hiring. Like every single company is behind sales repairing. So it's like, okay, what did you do? And that's why we thought behind sales repairing, how did you fix that? So it's things like that where I think it's better is in the one on ones. And so like I, the CEO, there's a terrific company called Harvey. I love the company and it's an agent that lawyers use to make themselves much more productive. And it's one of the AI application companies that is really working and first time CEO company is ripping and he's learning it and he's got venture capitalists on his board and they're helpful but they've never seen the movies. So he, he can be quite vulnerable. With me, it's like, this is, I'm really stressed about this. Should I be stressed about this? And I can be really straight with him in talk, talking through it. That, that is super rewarding that part of the kind of one on one coaching.

Do you think you could have done it when you were younger?

No.

Why?

I hadn't made all the mistakes, you know, I hadn't, I hadn't learned all this stuff. So I'm able to impart some of that on these founders as part of.

This coaching to these employees. We've talked about this. Like there is a, there's a lot of people out there that claim to know what, how the hell to run a company. Right? But there's like very few people like yourself that have like been to the top of Everest. Like very few and yet lots, lots of, lots of experts out there. And like we've talked about this whole like founder mode versus manager mode essay. I think it's a fascinating discussion. I also think it's kind of like the dumbest thing ever. That there is one way to do this thing, you know, this insane thing that there's only one way to prescribe and you have to be like one or the other. Like, do you, is this something that founders are even talking about? Like, and obviously you're dealing with. They're all at a different place in their journey. Right? Like in time and space. Like, is this something that there's always been, I guess this classic pushback on as they scale that they, they have to build more bureaucracy and from a manager mode kind of perspective, a more like classically trained, I guess, manager. Like, I don't know, are these things you talk about, if that makes any sense.

Everyone's talking about founder road. Like everyone's talking about, everyone's using it. Yeah, it's front and center. I think what's good that's happening right now is there's been kind of a classic playbook of how to be a CEO and people have just kind of done it the same way. And founder mode came out. There's other stuff that's come up. Like the way Bezos ran Amazon was different and his leadership principles were kind of different in the way Jensen Huang runs Nvidia is very different. And so there's all these new playbooks coming out about how CEOs actually did it that are really divergent from what consensus is. So I think there's kind of a rethinking of what it's like to be a CEO, how you run a company, what those best practices are. And I got Jensen came and spoke at an event Sequoia had. I don't know Jensen, but he did a little huddle after with a bunch of people and I asked him, you know, you've got all these unusual best practices. Like one of his best practices, he doesn't do one on one meetings, which is kind of classic Silicon Valley, one on ones once a week with our employees. He, he doesn't have small like team meetings. Every meeting is large. He doesn't have like eight direct reports. He has like 60 direct reports, 50 reports. He does something interesting in feedback. He gives positive and negative feedback in front of everyone. Conventional wisdom is if negative feedback in private, positive feedback in public. So you sort of rethought some of the basics of how they teach you to be a manager in Silicon Valley. And I, and a lot of it kind of resonated with me. And I asked him like, you've got a very unusual approach. If and when you step down from Nvidia and a new CEO takes over, will they take over your operating system? They should know. He's like, I designed this for myself, it works perfectly for me. The next person should come in and do it however they think they should do it. So I think there's a wholesale kind of rethinking of the role of the CEO, how they do it. And I think it's really positive development. Certainly Elon Musk runs his companies in a very unusual way and some of them are working really well. Some obviously.

Is that something I was going to say that the CEOs ask you? Like, I'm sure, like if. I mean, you dealt with imposter in general. We all talked about it. I'm sure these CEOs are dealing with it in the moment and are asking questions. Do they need to be more. Do they need to do it a certain way. So is that, is that a narrative that you hear and like push back against?

I try not to impose, like, here's how you do it. Because I do think everyone should. Jensen said something interesting. He said, no, the next person to do it. And he said, it's almost like you're, you're designing a race car for yourself that fits you perfectly and all your idiosyncrasies perfectly. So I try to be a little less prescriptive. I say, well, here's how we do it at HubSpot. But a lot of times in these calls I hear, like on this call we just had this guy named Kareem, terrific guy. He runs a company called Clay. Clay is ripping Terrific company, great CEO. And he was talking about how he hired and it was really different than what I expected. And he just wasn't doing it the way everyone else did it. And he knew how everyone else did it and he kind of invented a new way to do it and he shared it with everyone. And my inclination was like, you go for it. Commissioner Whistle was probably wrong about this stuff. You might have it right. Maybe somebody should copy it. So I try not to impose, like, here's how to do it. And if somebody's doing something a little bit weird that sounds like, know, conventional. Wilson might be wrong, you might be right. I encourage it.

The other approach that people, you know, oftentimes talk about, you talk about Playbook. It's almost like they're trying to design like a company where if you just hot swapped out the CEO with somebody else, that everything would keep going because it's like the company is the unit and everything is like that. And I think that just ignores reality. Like, that's not how things work. People don't work for companies, they work for people. Right. And I think that the Jensen thing like that, honestly that to me, this, my annoyance on some of the stuff with Founder Mode is I just don't think it's unique to a founder necessarily. I think it's unique to a person. Like, I think that, I think Nikesh Arora at Palo Alto Networks is running it like he owns the business or like he owns a lot of it, rather than just like, you know, is entering as a manager. And so, you know, Fiji at Instacart, like, you know, they were running it like they believe it and like they have the moral authority. And so at least to me, I think one big thing that I believe in is like, you have to make it your own because you have to make it authentic to you. Otherwise you're not leading in a way that's actually true to yourself. And so I actually like the idea of, like, do it your own way, but I just think it's something that's specific to the leader rather than specific to a founder.

I'm going to push back on that, though. Like, to an extent. Yes.

Right.

You take too much ownership. All right, Brian, you talked about this in your latest paper. Right. And you are not in inspiration mode anymore. You know, you are. This. This is my company. This is my company. Right. This is my vision. Right. And so it's.

It's a.

It's a. I mean, you see it more than I do in Silicon Valley. But it's very, very difficult to lead people once they feel they're living someone else's vision in someone else's dream versus having ownership in what we're trying to create here.

One of the things I actually was going to ask you guys about. So back to the Boston sports, the Red Sox. Part of the reason Boston sports fans are incorrigible is we didn't win a world series for 86 years and we're as passionate Red Sox fans. We finally won in 2004.

I do appreciate that you said we about the losses, too. Like, when I was at Duke, one thing that would happen is people would say we about the basketball team and they about the football team. They lost, we won. And you're just like, no, you can't do that. You're we on both. So I do appreciate you saying, okay.

That was a quick pickup. But kind of the magic of that team was it was a whole bunch of people that were growing up through their system. They grabbed them out of friggin high school, the minors, and then they had Kurt Schilling and Pedro Martinez and David Ortiz, who were expensive free agents. And it was that mixture of homegrown and veteran talent, not a lot of it, but enough veteran talent that really pushed them over the edge. I always thought HubSpot worked best. We had one or two sort of free agents from the outside that we hired from whatever, salesforce.com or something, but mostly homegrown. Like, if you look at the HubSpot management team today, it is pretty much homegrown. There's two kind of veteran free agents. How was it like that in the NFL and how is it like that in the NBA on the homegrown versus, like, what was the deal with it?

I think it's there. Absolutely. Like, even just to go back to the college football dynamic, that's changed now with the transfer portal. Like, look at these schools like Florida State and Colorado that have, like, gone all in on the transfer portal, where they get 50 new kids a year. Like, the entire. Even just to go back to the college football dynamic. That's changed now with the transfer portal. Like, look at these schools like Florida State and Colorado that have, like, gone all in on the transfer portal, where they get 50 new kids a year. Like, the entire roster turns over. These literally are mercenaries, right? And there's not a lot of success and there's, like, pushback against some of these. Like, certainly there's a balance to your point. Like, you know, you do have to go be selective in free agency, but a lot of your culture, again, in the heart of your team, needs to be, you know, developed from the ground up. And then pro sports. I think it's a huge. A huge balancing act. Like, they're the, you know, obviously, I think teams that are far more active in free agency and going out and getting these players and trying to do the quick fix. And then there's these organizations that don't and add little pieces to it. Again, I think about your Patriots that, like, the core of that locker room, like the Teddy Bruskies and like, you know, the guys that, like, were the heartbeat of that, and then they would add little pieces. Oh, we can go trade for Randy Moss, because, like, again, our culture is set. And now he's going to come in and kind of that presence is so strong that he's going to have to, you know, adapt to us as opposed to, like, the other way around. But I think the great organizations find that balancing act. Absolutely. And I think the struggling ones, you go. You OD on, like, the mercenary. Like, I. I think it's a. It's a tough battle to climb. Tough hill.

Shane, you had that with the. With. With your teams.

Look, I'm a good guy, but I was kind of a mercenary when I went to the Miami Heat, okay? So, you know, LeBron James, Dwyane Wade, Chris Bosh, they get together, they have the big parade. Not four, not five, not six, not seven. Okay. On paper, that that team was so talented, right? You have first ballot, you know, generational players, and they found out the hard way that talent isn't enough. You know, they got beat in the finals by Mavericks team that had, you know, two hall of Famers, but a bunch of guys that just play together and play their roles. And I give LeBron, Dwayne and Chris a lot of credit. They learned a lot.

Okay?

For as great as they were, they learned, hey, like it's not just about our skill, right? And you know, I saw that if the Miami Heat would have won that championship, there's no way I would have gone to Miami. I was a free agent, I was going to San Antonio, but I thought, yeah, these guys are going to win, I can help them win. And so it's the right place for me. So when I went, you know, I was really amazed by sort of the humility, but also just the drive those, those guys had and the organization had. And again, I think they overthought the amount of, of glue guys that it took to get it done. And so, and we had tremendous glue guys in that locker room, like trim, like hall of Fame Idonis Haslam and Mike Miller, Mario Chalmers, you know, Rashard Lewis, you know, Ray Allen at the end of his career, amazing glue guy. And we put together a team that was truly a team, right? And the beauty of that team was that, you know, as great as the hall of Famers were, the big three were, you know, they were part of a well oiled machine. And we went back to back championships, go to, go to three finals. You know, at the end we were a little bit tired and lost the Spurs. But it was an amazing lesson that yes, you got to have horses, you got to have horses to get in the race, right? But it takes really a team, it takes everybody's talents to reach the pinnacle. And so it was fun to live that and to see it live.

Shane, just for the digression, can you tell us, you talked about the big three. Can you tell us about the little 12 and the origin of that nickname?

So that's a good, you know, so you know, obviously we all know who the stars are. All right, so HubSpot, it's, you know, head of sales and the sales team, they're all the kind of the, the athletes, the jocks. And so same thing happened in Miami with the big three, okay? And those guys are awesome teammates, but they were divas and they got special, you know, they were divas and we called them on it. But it was, you know, every team has like special fan appreciation night. And for us it was Casino Night. And Casino Night is like the one night where they, they serve like the, the fan base, like free alcohol. They open up the arena and we play table games. So like we're all out there like in the mask, people are pretty loose. All right, so I got women like grabbing my ass and like, you know, it's crazy. I'm looking around and I don't see the big three, all right? I don't see LeBron, D. Wade and, and, and Chris in this meat market that we're thrown out to, you know, once a year to thank our fans, which is awesome, but it gets handsy. And so I look around, I'm like, where are the big three at? And someone said, oh, they had a private reception with a select group of courtside season tickets before this, before the Vegas night. And I'm like, what is this shit? What is this? This is a dichotomy. This is unfair. I say, well, what do we have here? We got the big three and the little 12. So that's how the little 12 was born. And it became a thing. And so as much as we love the big three, we told them, you cannot win without the little 12. And we, and that, you know, I should have trademarked that. But that was from Vegas night and a few handsy, you know, season ticket holders.

Halligan, speaking of legends, you know, stepping out, we got to talk about you stepping out of HubSpot, out of the CEO role, right? And going into. By the way, I'm sort of high ego that you didn't fight with my classification of you as a legend.

I. By the way, there's a great, great. It was so smooth, that transition right there.

Ravi, you call me lynching all the time. Like I'm used to it.

I, I love it, I love it, I love it. Look, you gotta, you gotta own, have your game. But I think that maybe a few things. One, how long had you been CEO and obviously founder, but before the snowmobile accident and where were, what were you thinking before the snowmobile accident? What were you thinking after? And tell us all about it. Obviously we have Alex here who had, you know, kind of a life threatening injury as well and a really impactful one. And so there's, there's a lot here.

Okay, I'll tell you the snowmobile. So I was Hug Putt CEO for 15 years and I was snowmobiling one day and I basically went off the cliff. My son was driving and I was on the back and there was a big curve coming up. I tapped him on the helmet and I said, you know, it's big turn coming. You slow down. I still build a lot and you heard me, sugar said in, in. He had the snowbill a lot. It's not his fault. He got kind of breaking the gas backwards, hit the gas at the wrong time. We went up over the lip and just, just lost gravity. I Remember going over and just like, oh my God. And then, you know, your brain just gets shut up. I don't remember flying down, a mile down. Smashing snowmobiles in a thousand pieces. We were in a thousand pieces and we're lying at the bottom of the snow. We were passed out for a while. I don't know how long. I woke up first, woke him up and we worked a mess. And I just remember sitting there like, I don't think we're gonna live. Like we were in the middle of nowhere. We. We didn't have our phone. It was freezing cold and no one knew where we were. I was like, this is it. And I remember sitting there like, I get out of this thing, I'm going to make some changes and I'm going to go through all the changes I wanted to make. But one of them was like, I don't really enjoy day to day being CEO of Hubson anymore. It's got 8,000 people. It's just not the same for me. I'd like a smaller company. I'm going to, I'm going to resign if I live. And I made some other promises myself. It turned out we're sitting there for an hour and I didn't think I had my phone. I did have my phone. He's like, check again. And I had just enough bars, two bars and AT&T really saved our lives. Dialed 911911, by the way, I wish I was a startup. I would definitely invest in it. It's a fantastic service. And anyway, I remember the lady's very quick call and she's like, well, sit tight. And I was like, I can't move. I said, definitely, it's a thing. And then she called the local fire stations in Vermont, Woodstock and Bridgewater. And the volunteers know in the fire station. So then she has to figure out the mobile phones of the first responders in the area, calls them and then they take their snowmobiles around and they come and, you know, find us. So they start working on my son first. And remember the guy who found us? Because he kind of got on top of me and his face was right on top of my face. And he's like, Halligan. I said, yeah. He said it like he knew me. It's like, it's Joey. Yeah, okay. Yeah. Can you help me out? He's like, no, no, no, it's Joey. I, I mow your lawn. I, I plow your way. And I was like, can you get me out of here? He's like, yeah, yeah. So they Kind of glue us together. Helicopter us. Dartmouth University. And anyway, put Humpty Dumpy and his son back together. So you can't see it now, but, like, underneath my shirt is, like, massive scars. I don't have a leg that looks as bad as Alex, but I've got 33 screws in me, bunch of loose ones in my head, and I'm very lucky to be alive. But I guess the reason you prime the story is I. I was out of work for seven months. I couldn't work as a wheelchair. And at the. At the end of the seven months, it's like I'm just. There's a woman who's running hubs. I was doing a great job while. It's kind of like I'm out all yours. And I'm much happier not being seen, man.

I feel like there's a lot there. Did you break your tib fit, by the way? Did I? Is that right? Did you break your leg?

Yep.

Join the club. Small, small brotherhood.

Yeah.

Luckily, it's the only one.

I broke my leg looks awful. It's covered on both sides with huge stars, but nothing like yours, man. Wow. Wow.

So literally, I mean, you kind of have. I mean, different than mine. You have. You. You're laying there. I mean, like, you're like that. How long were you there before they got. They found you?

A couple hours, hour and a half. A while we sitting there in the.

Snow and while you're lying there. Distinctly one of the thoughts is that if I get out of this.

Yeah. I'm gonna make all kinds to my life. And I think it's like almost dying is kind of useful for living.

Yeah, for sure.

What else. What else did you think about? Did you have any other revelations in the snow that moment?

I just. It's some things that have changed. I'm not going to go through everything. So it's really personal, but I would just say really edited down the number of relationships I have with other humans. And anyone who wasn't sort of adding energy in my life, I edited out. And I'm much closer to my family, much closer to my son, and much closer to my very close group of friends. And that. That's been very different and it's been great.

What was that process like? So was your. With your son's injuries similar? Did you guys have.

I mean, also broke his leg, broke his knee, hit his head real bad. He had a bunch of bad injuries, too.

And so you're kind of doing rehab and healing together on this journey during.

COVID it Was this really weird time to do it. So no one can visit you in the hospital. It was a very odd time. But the nurses, I feel like, really saved my life. The doctors and the nurses were amazing.

And when did you make the official decision? Like, when did. You were like, I'm doing this, I'm stepping away. Like where in the journey.

I decided that day in the snow. And then I could really couldn't work. I couldn't. Like, I was really debilitated for a long period of time. And then maybe four or five months in, I was in a wheelchair. I could kind of get around to have my co founder come and visit me. And I was like, listen, I'm. I'm hanging him up. And he was, he was surprised and he, you know, he pushed back a little bit. I was like, I made my, made my mind up. The more interesting conversation was with the woman who was running HubSpot while I was out.

And she's still the CEO.

Yeah, a couple interesting things about that. The week before my accident, we had a board meeting. And on the agenda of the board meeting was the. Was hit by. There was Brian, Brian Dash hit by a bus. Just a stupid analogy people in business use. Like if the CEO gets it, what happens? And it was very brief conversation. We had this woman, Yamini, she's fabulous. And my co founder and I like Yami should take over. I was like, cool. And it's like, he's not going to get by us. And then snowmobile accident. And so about six months into my rehab, I called her and I was, I needed to tell her that I wasn't taking over. And I called her and it's funny, I heard her husband tell the story. She was downstairs and I texted her, hey, can you talk on the phone? And I hadn't talked to her for a long time and she looked at her husband and she said, brian wants me to call him. I think he's going to fire me. He's going to fire me. Her husband is tech cash, really funny guy and he's in the industry and he's like. She thought she was gonna get fired. She went up and had a phone call with me and I said, I'm not coming back. You're doing terrific job. I'd love you to be the CEO HubSpot. And she said, hell no. I really don't like the job. It's brutal. No, you know, we'll be, you know, I'll be your CEO or co CEO, but I'm not ready. No way. I was like, either it's you are going to hire some schmuck from the outside, so you ought to do it. She agreed to do it. And then she comes downstairs to her husband and she's crying and her husband was like, oh, he thought she got fired.

Brian, what is that? One of the things you wrote again yesterday and you've told me separately is like a lot of CEOs don't like their jobs. Like now that you've told that story, you've told it to a few people. Like they confide in you when you ask them, do you like your job? What have you learned on that? Like one, like do people not like it? Why do they stay in it? Like, what have you learned on that?

They don't like the day to day work of it. They like the mission, they like the ego, they like the brand. But for the most part, almost none of them like the work. I think most CEOs overvalue their value to over overestimate their value to the company. I won't say which company is the Sequoia company. And I was talking to the CEO, going through some hard times actually, and I said, you know, why don't you resign? Like every time I talk to you, you're complaining a lot and doesn't seem like you're happy. Like you've got a couple kids, your wife, you seem like outside of work. I kind of know him a little bit. He seems awesome and he's like, oh, the company would never survive without me. It's like you'd be surprised.

Brian, when did it change? Like when during the journey of hu spot, did it like get to a point where the, like the scale, I guess and. Or like after going public, like when did it become more negative than positive?

And some people like how many of the women around likes this phase? Fine. I kind of break it as like 1 to 10 employees. 10 to 100. 100 to a thousand. 10,000 plus. A thousand plus. 1 to 10. I would give myself like a C plus. Like I didn't. My co founder did 99% of the work in the very early stage.

How about joy though? Like how like fulfilling, how fulfilled? Like those stages, those same stages from.

That standpoint, same C plus like we didn't have it, we didn't know if it was gonna work. It's like, yeah, when we were like five employees, I would put the odds that we would have created a company where $25 billion very low. Like it wasn't going that well. 10 to 100. I was super comfortable, happy and kind of joyful. But this is starting to work. I didn't know what I was doing. I'd been in a company that size before, like a. I thought it was actually good 100 to 1000. I had some experience in there too. I kind of liked it, you know, B plus and then a thousand plus, you know, C minus. I just didn't enjoy the day to day of it. Yeah. And probably shame on me. I should have crafted like if all this founder mode stuff and Jensen Huang stuff and I have been. If all of this talk about how do you be a CEO and how do you design the job for yourself had been around then I think I would have been a little bit bolder in how I approach things. Anyway, I didn't like my job. That and most CEOs of startups, they're risk seeking the early stage people, they do it, you know, they do it for a lot of reasons. But the day to day joy of it typically isn't one of them.

Why did you stay before? Because I take your point on why other people stay. Right. All the things you said, there's ego, there's sort of overestimating your own importance. You don't strike me as actually somebody who cares a ton about what other people think. By the way. Just as an aside, every time at Sequoia we hire somebody, we write a memo with like what our thesis is for what they're going to be. And in, in Brian's memo, Pat Grady wrote it and then there's a list of, you know, pros and then risks and one of the pros for Brian is dgaf. Okay, so for those that are not inclined, you know, it stands for doesn't give a fuck. Then one of the risks for Brian was also DGAF doesn't give a fuck, which I just thought was a cool description of Brian.

But were you like both signs of that are right by the.

No, no. Having worked with you now, I can tell you I agree with that characterization, but I love it. But why were you staying before the snowmobile accident?

I have an know I'm not devoid of uh, HubSpot.