The Exchanges

Q place also for Dylan, which is obviously kind of this kind of two billion dollar moonshot, like grant kind of Elon Musk style. And Brian, we were saying that we don't talk enough about CEO comp. I wanted to, why don't we start with you, Brian, on this, given you're the best person here to speak about it. How do you think about this and how do you analyze that?

A Now, I think CEO comp is pretty broken, uh, at the moment, and there's two things that I think are pretty broken about it. The first is just everyone really relies heavily on RSUs. And when I grew up in the industry, I hate to be like, I'd be like, I'm back in the old days. Um, it was mostly ISOs. It was optioned until 2006 and regulations changed and the expensing of that changed. So the world kind of moved to RSUs. It just creates sort of a risk averse behavior in the CEO. Like it's basically cash comp goes up and down a little bit, let's say, but an ISO you're swinging for the fences. Like you've got a strong incentive to swing. And so it's really had a dampening effect on the risk-seeking behavior of a CEO that I think more companies should want, and it's kind of pervasive across the industry. So I don't like this RSU comp thing. That's the first problem I see with all this stuff. The other problem with comp is almost every company looks to CO comp, and the way it works behind the scenes is, you know, HubSpot's got a compensation committee. Everyone's got a compensation committee. And HubSpot wants to pay the CEO, let's say, at the 75th percentile of what her peers make. And so we look at 20 different peers of similar sized companies, the last thing, blah, blah, blah, blah. And we peg her at that 75th percentile, which in her case is, you know, it's twenty million bucks, a …

AI assessment note: “I think CEO comp is pretty broken, uh, at the moment”

Q place also for Dylan, which is obviously kind of this kind of two billion dollar moonshot, like grant kind of Elon Musk style. And Brian, we were saying that we don't talk enough about CEO comp. I wanted to, why don't we start with you, Brian, on this, given you're the best person here to speak about it. How do you think about this and how do you analyze that?

A Now, I think CEO comp is pretty broken, uh, at the moment, and there's two things that I think are pretty broken about it. The first is just everyone really relies heavily on RSUs. And when I grew up in the industry, I hate to be like, I'd be like, I'm back in the old days. Um, it was mostly ISOs. It was optioned until 2006 and regulations changed and the expensing of that changed. So the world kind of moved to RSUs. It just creates sort of a risk averse behavior in the CEO. Like it's basically cash comp goes up and down a little bit, let's say, but an ISO you're swinging for the fences. Like you've got a strong incentive to swing. And so it's really had a dampening effect on the risk-seeking behavior of a CEO that I think more companies should want, and it's kind of pervasive across the industry. So I don't like this RSU comp thing. That's the first problem I see with all this stuff. The other problem with comp is almost every company looks to CO comp, and the way it works behind the scenes is, you know, HubSpot's got a compensation committee. Everyone's got a compensation committee. And HubSpot wants to pay the CEO, let's say, at the 75th percentile of what her peers make. And so we look at 20 different peers of similar sized companies, the last thing, blah, blah, blah, blah. And we peg her at that 75th percentile, which in her case is, you know, it's twenty million bucks, a …

AI assessment note: “I think CEO comp is pretty broken, uh, at the moment, and there's two things”

Q underrated element of a CEO's journey. And I, I mean, I couldn't do it without my mother. And so I just knew that, uh, uh, 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?

A A 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 a hundred years ago in 1990, and I saved for 10 years, and by the time I left, there were 5000 employees. It was a great, I had a great run there. Um, and it just got very lucky landing in that spot, um, and I give my mom and Mrs. Saracen 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, they're high. The R squared on that is quite high. Uh, so I've always been overprepared 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 in the right time, I've noticed.

AI assessment note: “maybe it's half preparation, half luck, half right place at the right time”

Q Like, like, what sort of thing, if you don't remember?

A Ok, I'll give you one. I absolutely crushed my back, uh, last quarter moving a couch, and it was like I had a knife stuck in my back, and I don't want to do that again. And so I go to PT, I'm doing yoga. Like I'm obsessed now with my back and it's much better, but I want my back to be, it's like, okay. I think of it as like, you're redoing a house. You've got the crappiest room in your house. You want to go in the crappiest room and make your crappiest room, your best room. And the same thing with your body. Okay. My back is the worst part of my body. How do I make it go from the worst part of my body to the best part of my body? So like that, for example, is on my list this quarter.

AI assessment note: “Ok, I'll give you one. I absolutely crushed my back”

Q that. I should be like that. And you said before, You know, be yourself. Well, actually, I think it was Ernst Hemingway, to be fair. He said be, you know, plagiarism is a friend unless you're Bill Ackman. Uh, be yourself, because everyone, 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?

A I still don't, Harry. Uh, I still really don't. Um, 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 that 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 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. In leadership styles. And I, I tried to take the best from all of them, but I was just struck as I look back at how different they all are. So I don't think there's 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, their 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 10th. 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 start…

AI assessment note: “I still don't, Harry. Uh, I still really don't.”

Q Solving for their team over the enterprise. Do you think they know that they're doing that?

A They definitely get feedback on it. Another thing I would say, this is a little depressing, but we, we, we do net promoter surveys for the whole company. We've been doing this for. 15 years or once a quarter, we asked every, every employee scale one to 10. How likely are you to refer HubSpot as a place to work? And then why people write novels on that too? And we track it and then we track it by department. And. And the scores move around by departments. They can move around a lot. And so let's just say you've got a VP of marketing and their net promoter score for marketing is like. 55, 65, 58, 59, then boom, 30. And some feedback on that VP. And so we package all that up. We give feedback to the VP. Oh, you're solving for the team over the end. And they work on it. What I found, and it's a little depressing is. You put somebody on a recovery plan, more often than not, they don't recover, and we end up parting ways to that person. Um, once they've lost their team, they almost never can get that team back.

AI assessment note: “They definitely get feedback on it.”

Q 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 am. Yeah. So we both are. What do you think makes them successful?

A Okay. Nothing quite well. Uh, I think there's a network effect in the venture business, of course. So they have an 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, brands more valuable than others is very valuable in ventures. So that of course is given 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 Ruloff, 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 that Doug Leone gave them, and they work like, really work so, they work much harder than any other VCs have come across, and they're absolutely paranoid that they're going to lose it. They're also, 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 the failures. And I think they kind of dwell on their failures and they don't want to repeat those failures. I, 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 current cre…

AI assessment note: “where I think they're special. Is they don't take any of that for granted.”

Q but I, but again, like thinking back to the paperboy 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 Sandbox just get a seat on the rocket ship? What did you mean by sometimes the best?

A I don't think Sheryl was way off on that. And that was very much the case for me. So I remember This is really a hundred years ago, but I had three offers, um, and one was from PTC. And really my first job, Harry, was I was, uh, what they used to call a secretary. I was the secretary to the head of sales in this company, head of channels, actually, uh, and that was the offer. It was 20,000 dollars, 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 twenty billion market cap company. It's done quite well. And so I don't think Cheryl is, is far off in that hop on the rocket ship, uh, quote.

AI assessment note: “I chose the lowest paying job with the company that had the most upside”

Q that. I should be like that. And you said before, You know, be yourself. Well, actually, I think it was Ernst Hemingway, to be fair. He said be, you know, plagiarism is a friend unless you're Bill Ackman. Uh, be yourself, because everyone, 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?

A I still don't, Harry. Uh, I still really don't. Um, 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 that 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 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. In leadership styles. And I, I tried to take the best from all of them, but I was just struck as I look back at how different they all are. So I don't think there's 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, their 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 10th. 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 start…

AI assessment note: “I still don't, Harry. Uh, I still really don't.”

Q Speaking of people around you, Sequoia obviously led, uh, around. Can you talk to me about how Sequoia came into the fray and what that looked like?

A Sure. Uh, Sequoia was a big help to help. So I remember, so we're a Boston-based company, and Boston-based company is like, no one gave us a hoot. I mean, we would go out to the west coast and raise money. I remember the fundraising trips where Dharmesh and I, we'd get on the plane, We're all fired up. Like, we got this. We got 20 meetings on Sand Hill Road, up and down Sand Hill Road, and then I remember getting on the plane on the way back. We both just get crushed up and down Sand Hill Road. In this one particular trip, we had, like, whatever, 17 meetings with VCs and got 17 notes in a row. Our last meeting was a guy named Jim Getz. Jim Getz is kind of a legendary, uh, VC at Sequoia. So remember, Dharmesh wasn't with me this time, sitting in a conference room. And, uh, I was nervous, you know, 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 going to take for Sequoia to own a piece of HubSpot? And I said, really not much. Just give me a turn. I'm ready to go. I had no other options. 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, and super nice guy. And I thought we would have …

AI assessment note: “Our last meeting was a guy named Jim Getz... at Sequoia.”

Q Um, I agree with you also on the work hard. I've never seen an ethic like it. Um, fucking love Doug. Anyway, uh, can I ask another slightly personal one, but I heard that Sequoia bought some stock off you, 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?

A Yeah. It was sort of Series D. It was, uh, I forget how much they invested for it called, 40,000,250 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 route cause Salesforce.com invested in Google invested. This is before they had like big venture arms. Uh, so there just wasn't a lot of room in there and they came up with the, I thought a clever solution, which was we'll buy some of the exec team and founder shares, uh, 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 two hundred fifty million dollar valuation. Now the company's worth a hundred 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 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 goin…

AI assessment note: “Relative to my current net worth, it was very much a life-changing event.”

Q underrated element of a CEO's journey. And I, I mean, I couldn't do it without my mother. And so I just knew that, uh, uh, 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?

A A 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 a hundred years ago in 1990, and I saved for 10 years, and by the time I left, there were 5000 employees. It was a great, I had a great run there. Um, and it just got very lucky landing in that spot, um, and I give my mom and Mrs. Saracen 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, they're high. The R squared on that is quite high. Uh, so I've always been overprepared 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 in the right time, I've noticed.

AI assessment note: “Maybe it's half preparation, half luck, half right place at the right time”

Q It's fucking different. Doesn't matter. And so actually, are they a good source of cash? Are they supportive and won't throw you off a board when it's a shit quarter? And do you like working with them? I honestly say that to my, if I do anything on top of that, great. Let's have ice cream. What a win. But honestly, I don't buy the, like, am I being wrong?

A Well, I think it's important if your VCs haven't built companies before, or their pattern matching is light, they're new, um, having a great independent is worth its weight in gold. So when we were early, we had two founders on the board, we had two VCs on the board, and we had a terrific Our first independence woman named Gail Goodman that people wouldn't have heard of, but she started, she was the CEO of constant contact, which at the time was a real high flyer. And she had real operating experience that was relevant, timely. She was a couple of years up. The ice was from us. And the thing she had that was useful is that the VCs would get on me, like really grinding me about something, not growing fast enough, referring to whatever it would be. If, from time to time, if they were being too aggressive with me, she would sort of back them off. They were a little bit intimidated by her. Um, and that was very, very helpful. She gave us great operational stuff. So having other people in the room who have seen the movie is useful. And I would push back a little. Yes, everything is different post COVID. Yes, everything's different post AI. But building a team, raising money, um, you know, how do you build a category? How do you build a go-to-market machine? Like all of that, that transcends across from the friggin' 19 nineties to today so much of it. So I don't think things are tota…

AI assessment note: “And I would push back a little. Yes, everything is different post COVID.”

Q Did Figma kill the M and A market?

A It killed part of it, I think, or maybe killed part of it. Let's say you're a scale company and you're looking to buy business for 2030, forty million dollars. It's not just that it might not get approved like Figma didn't. It's, it's a 15 month cycle to find out. And so it used to be you're doing an acquisition is three or four months. Now it's like a good 15 months to get through the US, get through the UK, get through the EU. And so all that time, a lot can change. So I think you've got to think long and hard before doing a good size acquisition. Having said that, I think the smaller M&A market's going to be wide open.

AI assessment note: “It killed part of it, I think, or maybe killed part of it.”

Q Did Figma kill the M and A market?

A It killed part of it, I think, or maybe killed part of it. Let's say you're a scale company and you're looking to buy business for 2030, forty million dollars. It's not just that it might not get approved like Figma didn't. It's, it's a 15 month cycle to find out. And so it used to be you're doing an acquisition is three or four months. Now it's like a good 15 months to get through the US, get through the UK, get through the EU. And so all that time, a lot can change. So I think you've got to think long and hard before doing a good size acquisition. Having said that, I think the smaller M&A market's going to be wide open.

AI assessment note: “It killed part of it, I think, or maybe killed part of it.”

Q about security? My family lost everything when I was young and it, you know, what am I running from? A little bit is towards financial freedom of having enough to not worry for my family. Do you, do you think, do you appreciate the security that it brings or actually are you much more of a risk taker? It's like, ah, I was fine without money. I'll be fine. Whatever.

A I, I never worry that much about it. I always thought, I always thought I'd have some measure of success and I would be fine. I just always sort of had a confidence in that somewhere deep down inside. And so, yes, I'm financially secure. Fine. Uh, but I think I worried a little bit less about that than everybody else. There was something down deep inside of me that I wasn't that worried about that. I, I knew I had the ability to create something. Even when I was very young, just back to my youth, I had, I had the paper route, but I was that kid who always had a job. I worked at a gas station. I worked at a fish market. I was a bar back. I was a waiter. I did like every job you can imagine. I started a painting company. Every summer I painted about five percent of Cape Cod and just worked my way through. Every summer painted another five percent, and so I always knew that I, I was a, I would be, I would be fine financially. I just have that feeling deep down inside.

AI assessment note: “I never worry that much about it. I always thought I'd have some measure”

Q Um, I agree with you also on the work hard. I've never seen an ethic like it. Um, fucking love Doug. Anyway, uh, can I ask another slightly personal one, but I heard that Sequoia bought some stock off you, 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?

A Yeah. It was sort of Series D. It was, uh, I forget how much they invested for it called, 40,000,250 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 route cause Salesforce.com invested in Google invested. This is before they had like big venture arms. Uh, so there just wasn't a lot of room in there and they came up with the, I thought a clever solution, which was we'll buy some of the exec team and founder shares, uh, 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 two hundred fifty million dollar valuation. Now the company's worth a hundred 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 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 goin…

AI assessment note: “Relative to my current net worth, it was very much a life-changing event.”

Q Speaking of people around you, Sequoia obviously led, uh, around. Can you talk to me about how Sequoia came into the fray and what that looked like?

A Sure. Uh, Sequoia was a big help to help. So I remember, so we're a Boston-based company, and Boston-based company is like, no one gave us a hoot. I mean, we would go out to the west coast and raise money. I remember the fundraising trips where Dharmesh and I, we'd get on the plane, We're all fired up. Like, we got this. We got 20 meetings on Sand Hill Road, up and down Sand Hill Road, and then I remember getting on the plane on the way back. We both just get crushed up and down Sand Hill Road. In this one particular trip, we had, like, whatever, 17 meetings with VCs and got 17 notes in a row. Our last meeting was a guy named Jim Getz. Jim Getz is kind of a legendary, uh, VC at Sequoia. So remember, Dharmesh wasn't with me this time, sitting in a conference room. And, uh, I was nervous, you know, 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 going to take for Sequoia to own a piece of HubSpot? And I said, really not much. Just give me a turn. I'm ready to go. I had no other options. 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, and super nice guy. And I thought we would have …

AI assessment note: “Our last meeting was a guy named Jim Getz. Jim Getz is kind of a legendary”

Q that I'm building a media company. We have many people in the media company. It does millions in revenue. To me, it is building a company. Whatever that is, you said before about the importance of investors have been former CEOs and former operators. Why do you think it's so important that your VC has been a former operator or CEO? And can you just take me to that thinking?

A Okay. I remember when we were starting HubSpot, we wanted VCs who had been CEOs. And by the way, Most startups don't have a choice of, like, 20 term sheets. We certainly didn't, um, but if, if we had, uh, had the option of having a, a VC who was the CEO before, that was, we would go with that. It was a plus, if the terms were the same. And our A and our B were VCs who had been CEOs before. Pat had not, um, and he did the D, and he had an observer seat, Um, and I would say Pat was relatively quiet, but Pat figured out ways to add value that were super useful around benchmarking relative to every other tech company in the world, network with every other tech company in the world, um, and really geeking out early on unit economics for SaaS companies. So he found ways to add value where he didn't stick his nose into operational details per se. So I think, I think both can work. I think the reality is there's very few VCs today who are been that, been there, done that CEOs who have built big companies. I just, I, I, there's very, very few of them. So I don't, I don't think you can have that criteria anymore.

AI assessment note: “I don't think you can have that criteria anymore.”

Q why I sacrifice everything that I do. Literally, I never see daylight. Um, ah, and I was then reminded of what really makes me happy by my mentor, and it was going for a coffee with my mother and walking around the park, and then the money Yes, it's important to an extent, but it's not everything. If I ask you what really makes you happy, Brian, do you know?

A I don't think it's as much about things that make me happy as about being devoid of sadness or unhappiness, um, and avoiding things that irritate me or I don't enjoy the passage of time of, and so I'm trying to shed in my life People, I hate to say that, in things I don't like to do as much as I possibly can. I don't think, I'm quite sure money doesn't buy you happiness. Um, I can say I have a bunch of it now. I never had it, and I'm no happier or less happy than I was. I would give myself, like, my MPS score on my happiness is, like, between an eight and a nine. Like, pretty happy. Uh, and I've been between an eight and a nine forever. Uh, Money buys you something, money buys you convenience. It's really the only thing it buys, uh, and That's valuable. It's, it, it enables you to do things, to do less things you don't like to do. I'll give you a very good example. The one thing I've done with, you know, some of the wealth I've created is I've hired, back to my mother. When my mother was dying, she had a home health aide named Marilyn from the Philippines. I loved Marilyn. And she took care of my mother for years. She was almost part of the family. And, uh, she's just terrific, and then my mother sadly passed away, sort of loosely kept in touch with Marilyn, and then a couple years later, Harry, I had a brutal snowmobile accident. I was in the hospital for a long time, was in a…

AI assessment note: “I don't think it's as much about things that make me happy as about being devoid of sadness”

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

A Okay, this is your honor part because I'm not that good at this. So I, 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 kind of 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, it could be weeks or months before you get an email response from me. But if you happen to be engaging me on something that's on my quarterly plan, I'm back to you in half a second. Uh, so I probably am, I, I would, I would be, I, I, yeah, there would be red flags. If I were hiring me, I would have some red flags on that.

AI assessment note: “every quarter I do a quarterly plan. So I kind of grew up in sales.”

Q about security? My family lost everything when I was young and it, you know, what am I running from? A little bit is towards financial freedom of having enough to not worry for my family. Do you, do you think, do you appreciate the security that it brings or actually are you much more of a risk taker? It's like, ah, I was fine without money. I'll be fine. Whatever.

A I, I never worry that much about it. I always thought, I always thought I'd have some measure of success and I would be fine. I just always sort of had a confidence in that somewhere deep down inside. And so, yes, I'm financially secure. Fine. Uh, but I think I worried a little bit less about that than everybody else. There was something down deep inside of me that I wasn't that worried about that. I, I knew I had the ability to create something. Even when I was very young, just back to my youth, I had, I had the paper route, but I was that kid who always had a job. I worked at a gas station. I worked at a fish market. I was a bar back. I was a waiter. I did like every job you can imagine. I started a painting company. Every summer I painted about five percent of Cape Cod and just worked my way through. Every summer painted another five percent, and so I always knew that I, I was a, I would be, I would be fine financially. I just have that feeling deep down inside.

AI assessment note: “I never worry that much about it. I always thought I'd have some measure”

Q the fuck? 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 an all-star and align everyone to the same goal? Or is it like, may everyone have the same similar broad set of skills? You don't want that, because then you'll have weaknesses that aren't covered. What does that actually mean in reality?

A I think it's really underrated, and I see these startup, I spend a lot of time with founder, uh, startup founders who are CEOs. I 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 these this year. Here are the main initiatives we're going to 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 going to ignore them for another year. Once we got some discipline around that, then the effectors got aligned. The company worked a lot better.

AI assessment note: “we got into a planning cycle where we can be like, here's what our mission is”

Q Like, like, what sort of thing, if you don't remember?

A Ok, I'll give you one. I absolutely crushed my back, uh, last quarter moving a couch, and it was like I had a knife stuck in my back, and I don't want to do that again. And so I go to PT, I'm doing yoga. Like I'm obsessed now with my back and it's much better, but I want my back to be, it's like, okay. I think of it as like, you're redoing a house. You've got the crappiest room in your house. You want to go in the crappiest room and make your crappiest room, your best room. And the same thing with your body. Okay. My back is the worst part of my body. How do I make it go from the worst part of my body to the best part of my body? So like that, for example, is on my list this quarter.

AI assessment note: “Ok, I'll give you one. I absolutely crushed my back, uh, last quarter”

Q I, I totally agree with you. I, I guess my question to you is, when you think about advising young people today, there's often the 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?

A 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 to scale ups, not even startups, like it 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, and sales, and channels, and marketing. I ended up doing lots of different things. They moved into 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 opportunities, 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. 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 infor…

AI assessment note: “So for me, joining a scale up twice really informed, uh, HubSpot”

Q The final one I just have to touch on before we do discuss some of the mechanics of your leadership is, I identify myself with TwentyVC. 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?

A Okay, it's a really good point about that. I remember looking at my review, maybe 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 and how those things came together. I was quite surprised at how much those things had merged together in the employee's 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 and kind of merged together. And I, I think that probably happens with CEOs of, or founders of all companies as they scale. And it took me by surprise how much those things came together. As we, as I transitioned 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 texts yesterday. I'm still very much involved, so I, I think I'm not totally 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.

AI assessment note: “As I transitioned out, I'm still involved, so it totally hasn't happened.”

Q 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. 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 what would you advise me?

A 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, your smaller organization. But at HubSpot, if we turn someone over a year and a half in, we definitely beat ourselves out 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.

AI assessment note: “one of my biggest lessons is that's about right.”

Q You mentioned the quirkiness. Yes, I'm quirky too. I also work really hard, and I drive a very intense culture of hard work. That's not very popular in modern society with younger people. 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.

A I think you have to be yourself. You have to be, 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. Uh, and that's fine. Um, now I think you fall in a trap where everyone's similar, but, um, I think you will, it, when you're, I would be surprised if anyone you hired didn't have some red flags. Um, yeah, I would be very, everyone I'd be hired, it's like, well, they've got some strengths and some weaknesses. I think where people, I think where scale ups fall down on hiring and founders fall down on hiring is you've got You've got a panel of people who are interviewing a VP from, for, of whatever, of products, and you've got 10, eight people interview them. If, if you've got candidate, first candidate, Mary, gets four, four out of 10, 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, that's just always happens. You always have the Jane. I think you're better off with the Mary, and you want kind of spike, a spiky team with some people who…

AI assessment note: “I think you have to be yourself. You have to shave off a little”

Q that I'm building a media company. We have many people in the media company. It does millions in revenue. To me, it is building a company. Whatever that is, you said before about the importance of investors have been former CEOs and former operators. Why do you think it's so important that your VC has been a former operator or CEO? And can you just take me to that thinking?

A Okay. I remember when we were starting HubSpot, we wanted VCs who had been CEOs. And by the way, Most startups don't have a choice of, like, 20 term sheets. We certainly didn't, um, but if, if we had, uh, had the option of having a, a VC who was the CEO before, that was, we would go with that. It was a plus, if the terms were the same. And our A and our B were VCs who had been CEOs before. Pat had not, um, and he did the D, and he had an observer seat, Um, and I would say Pat was relatively quiet, but Pat figured out ways to add value that were super useful around benchmarking relative to every other tech company in the world, network with every other tech company in the world, um, and really geeking out early on unit economics for SaaS companies. So he found ways to add value where he didn't stick his nose into operational details per se. So I think, I think both can work. I think the reality is there's very few VCs today who are been that, been there, done that CEOs who have built big companies. I just, I, I, there's very, very few of them. So I don't, I don't think you can have that criteria anymore.

AI assessment note: “I think both can work... I don't think you can have that criteria anymore.”

Q Do you think the VC product is good today, Brian?

A I think it is. Um, I mean, at the end of the day, they're selling a product to their LPs, right? They're the, the customer's kind of the LP, actually. Um, And. Five percent of the VCs are incredibly successful in 90, you know, 90% or math in a decent or a lot. Very few are really successful, but they're so successful that the category writ large does pretty well. So from that perspective, I think it's a good category. I continue to invest in it. Um, If you look at it though, the small VCs are the ones where the, where the alpha is, uh, not the big ones. And VCs, there's a tendency to get bigger. But in terms of the offering to the, the, their other customer, the founders, when we did our Series A, it was a five million dollar round on a six million dollar pre-money valuation. So we sold 47, 70% of our company on Series A. That was standard, Harry. That was like standard.

AI assessment note: “I think it is. Um, I mean, at the end of the day”