How to be a CEO when AI breaks all the old playbooks | Sequoia CEO Coach Brian Halligan

Transcript

The thing about being a founder CEO is there’s no one there to rescue you. Your parents aren’t going to rescue you. Your VC is not going to rescue you. That hits you when you hit your first crisis. Starting a company has never been easier. Scaling one into a durable, high-impact organization has never been harder. The number of companies formed is going to grow much more over the next 10 years relative to the last 10 years. It’s just going to be hard to stand out and really accelerate. What’s most different about what it was like to be a CEO maybe 10, 20 years ago versus today? There’s a massive tax on optionality when you can move this fast and try a lot of things. It puts pressure on the CEOs to be faster and better decision-makers. A lot of people in the world want to be founders. They want to be CEOs. I don’t think anyone can do it. People talk about 996. It’s way more than that. Founders are seven days a week. They’re always on. I text Sunday nights. It’s full contact. Do you feel like there are specific profiles or traits to be successful? I look for four things. I call it my lock algorithm. Today my guest is Brian Halligan, co-founder and longtime CEO of HubSpot. I asked Brian to come on this podcast because he is, more than anyone I’ve met, a student of the job of a CEO. After leaving HubSpot last year, he became the in-house CEO coach at Sequoia, where he brings together dozens of top CEOs to learn from each other. He does one-on-one coaching with some of the world’s top CEOs. He also hosts a popular podcast called Long Strange Trip, where he interviews some of the world’s most successful CEOs. In this conversation, we unpack what it takes to be a successful CEO in today’s era. Let’s get into it after a short word from our wonderful sponsors. Applications break in all kinds of ways. Crashes, slowdowns, regressions, and the stuff that you only see once real users show up. Sentry catches it all. 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And all of this is powered by feature flags that are tied to real-time data, so that you can roll out safely, target precisely, and learn continuously. Datadog is more than engineering metrics. It’s where great product teams learn faster, fix smarter, and ship with confidence. Request a demo at datadoghq.com slash Lenny. That’s datadoghq.com slash Lenny. Brian, thank you so much for being here, and welcome to the podcast. Thanks for having me, Lenny. It’s my pleasure. I want to start with something that I’ve heard your board members say. The way they described you is as someone with a perpetual state of constructive dissatisfaction. Do you think this is a core foundational trait of successful CEOs, successful leaders? By the way, I like that description. When she, the woman named Lori Norrington, who’s a Southwest chair, said that, I liked it. I took it as a compliment. And I liked it. As I spend most of my time these days coaching very fast-growth CEOs, they all are like that. They’re all in a state of perpetual dissatisfaction, but in a positive way. One of the things, by the way, I like about the current crop of CEOs is they don’t really take stock of what they’ve done and feel it. They’re always a little dissatisfied with where they are and very focused on the end state. And I’ve been surprised at how humble this generation of CEOs is. I think of my generation of CEOs as being, I don’t know, humble wasn’t the first word that would come out of your mouth when you describe my generation. But this generation, I feel like, is different. And I’ve been impressed with it. Okay. I have a bunch of questions along these lines, because, one, you’ve been a CEO of an incredibly successful company for a long time, for about 20 years before you moved on to this new chapter. Now you work with a bunch of CEOs. You’re Sequoia’s in-house CEO coach. There’s a few things that I’ve heard you do. One is you gather groups of CEOs. And what I’ve read is that you have two tables. You have the kids’ table and the adults’ table. The kids’ table is CEOs of companies that are under about 100 employees. The adults’ table is over 100 employees. So let me ask you this: when you look at CEOs that move from the kids’ table to the adults’ table, other than they scale and grow, what is it that these CEOs that graduate from the kids’ table to the adults’ table do differently? The adults are really focused on, and all they really want to talk about is, their exec team. Their direct reports, how do you build your exec team, that next level down, org design. You would be surprised how much they think about that. And on average, I would say the adults are spending half their time just recruiting and interviewing. It’s pretty all-consuming. And I remember that from that phase in HubSpot’s growth. And it surprises people, like, wow, my job is really just to interview and hire. I didn’t know that was going to be the case. So that is one thing as they are making that transition. And I would just say, in general, people are very bad at this, and HubSpot was too. I think CEOs and everyone dramatically overrate their ability to interview and overrate their gut feeling and underrate a really high-quality blind reference. I interviewed Dave, the CEO from MongoDB, the other day. And he had an interesting study. On average, over his 10-year lifespan as the CEO of Mongo, there were two C-levels turned over per year. That’s a lot of turnover at the top. And I didn’t keep track of it like Dave, but I think HubSpot was similar. And all of these startups are similar, too. And so people are working on that and struggling with it. That is one thing in common with all of them. What do you do when you coach someone on that? When you’re like, okay, you think you’re amazing at interviewing? You think you know who’s going to work out? What advice do you give them to help them develop that skill? I think even me, I’ve been doing this for 150 years, I still think I overrate my ability to interview someone and really know if they’re a good fit. I give a couple pieces of advice. Parker Conrad has a good hack that I like. Before he’s got a C-level interview with a CFO, Chief Product Officer, whatever, he has them sign an NDA and sends them the last board deck or the board memo or some important doc. And he schedules a half-hour interview with them. And he just has a chat about the deck. And if they’re just very complimentary and it’s so great, you’re doing this amazing thing, it’s a major red flag to him because he wants someone that will challenge him and not a yes person. And I thought that was a pretty good hack to get inside someone’s head and how they think and how they’ll interact with you. Getting on a whiteboard and working through a problem, I think, is always a good thing. I think the standard interview of walking through your background, I don’t think is all that valuable. And I coach people to do blind references, find someone you know that worked with them. Before he's got a C-level interview with CFO, Chief Product Officer, whatever, he has him sign an NDA and sends them the last board deck or the board memo or some important doc. And he schedules a half-hour interview with them. And he just has a chat about the depth. And if they're just very complimentary and it's so great, you're doing this amazing thing, it's a major red flag to him because he wants someone that will challenge him and not a yes person. And I thought that was a pretty good hack to get inside someone's head and how they think and how they'll interact with you. Getting on a whiteboard and working through a problem, I think, is always a good thing. I think the standard interview of walking through your background is not all that valuable. And I coach people to do blind references, find someone that worked with them. VCs are good at this, by the way. And I get a lot of these, and you can tell some of them are like, we've already decided, we're checking the box, versus they're asking me hard questions about this person. And one of my favorite questions people ask is, would you enthusiastically rehire this person for that role, which I think is a really good question. On a scale of one to 10, how likely is it that you'll try to rehire this person back for me down the road? I think those types of questions are good. So not mailing in on those blind references, I think, is really good. My other piece of advice, and no one listens to me on this, is hire slow and fire fast. People hire fast and fire slow. If I had to guess, Lenny, within 18 months after you hire a C-level exec, at least 50% of the time they're gone. There's a high mortality rate on them. It's harder than people think. And so what you're saying here is there's only so much you can actually do to increase those odds. I think you can. And I think the blind references are key. I think doing real interactive work on a project together is key. I'll tell you one other thing we learned at HubSpot about this. We would have a candidate come in, let's say a head of engineering. And we'd have eight people interview them, and our scale is one to four. And let's say four people were four out of four and four people were two out of four. So that's candidate A, and then the next candidate comes in. Eight people interview them, and everyone's a three out of four. Almost every time we hired the three out of four, the person with the least amount of weaknesses. And we changed it, and we went with the spikier people. We went with people with weaknesses. We want people to challenge stuff. And that has worked out quite well. Our hit rate at HubSpot has improved. We also have shrunk the pool of people on that interview panel from eight to four. We just hired a head of product, and there were just four of us that interviewed them. I think that worked too. So I think there's things you can do to get better at it for sure. Okay. This is incredibly tactical and useful on the references piece. The toughest part is getting people to be honest because there's very little upside to them to say negative things about people. Is there anything that you've learned to help get real honest answers from folks you call for references? Well, I can just say, because I don't do this a lot anymore, but when people call me, I can tell what they've already decided. Mm-hmm, when they're really just looking for, when they ask me for the strengths and weaknesses, I'm like, they've already decided. When they ask me something hard, like on a scale of one to 10, how likely are you to hire them again, stuff like that, that kind of gets at the core, or were they the top 1% of your employees? That's a good question. Oh, were they top 10? That type of question is pretty good. So when I'm on the other side of it, I like when those types of questions come up. I'll tell you the other mistake everyone makes. I made it, all the CEOs were making it. You're hiring for whatever, head of engineering, and you're blown away by the resume. You're 50 employees and you're hiring this person who's been at Microsoft the last 10 years and has a fancy title and fancy division at Microsoft, and you hire them. There's just a massive impedance mismatch when you hire them on what their expectations are, what your expectations are, and the extent that you've got your shit together. You definitely don't if you're 50 or 500 employees, and they expect you to have your act together. And so that is another, avoid the big company hire. We hired so many people from Salesforce and Google, Microsoft, like a hundred percent attrition rate on all those folks. Something that I've seen at a lot of companies is there's phases of like, okay, now it's the McKinsey cohort comes in and we think that's going to be the answer. And that's the Apple group, and then that didn't work out, then the Amazon group. The McKinsey one never works. It never works. It never works. By definition, they would fail on my spectrum. Most founders are like me. They are skeptical of conventional wisdom. They're unhappy with the way the world works in some way. And so they're kind of far on that spectrum of rethinking conventional wisdom. And almost by definition, somebody who goes to work for McKinsey is very conservative in their outlook. And so I think that almost always fails. We're on this hiring kind of thread, so let me keep following this conversation. I read somewhere that you recommend building your team like the 2004 Red Sox. What does this mean? I'm a big sports fan, and big Boston Red Sox hadn't won, Lenny, a World Series in 86 years since they traded the Andrew. And they finally broke through and they finally won it in 2004. And the way they won it was they had a team of a bunch of homegrown, really high-quality, inexpensive talent that they drafted and came through the farm system. And then they got a few free agents like David Ortiz that a lot of people have heard of that they paid a fair amount of money to. Peter Martinez and Curt Schilling were kind of the canonical older, been there, done that, bigger company folks. And they mixed really nicely. The culture really worked. And I think that's the key. I think people underrate their homegrown talent, almost across the board, they underrate it. And I think you want that mix. You don't want to hire a whole bunch of been there, done that. You don't want to hire none of them. I imagine this is public, but you're now part owner of the Red Sox. I am part owner of the Red Sox, yes. Okay. I have questions for you along those lines. Okay. That's amazing advice. What I'm taking away here is people see all these fancy logos, amazing person, VP, this, that, Salesforce, Amazon, Google, whatever. And what you're saying here is don't underestimate the power of someone internal rising to the occasion. Yeah. If you look at HubSpot, half the management team are folks who have been there for approximately 150 years, which I like. And same with Apple, a lot of those people are homegrown. And so is there any tips here for doing this well? Is it just give people a chance? I tend to give people a chance. It's like if you're interviewing someone that's homegrown and they're VP for that C-level job versus hiring someone from the outside. Now, hiring someone from the outside, they're very good at interviewing from a big company. They look fancy. They're shiny. You haven't seen their warts. It's hard to figure out their warts unless you're very good at blind referencing. So you tend to overrate them and underrate your homegrown. So if it's pretty close, I think you give your homegrown a shot at it. What's interesting to me, Lenny, is Brian Chesky sort of rethought a lot of this stuff. And he's like, everyone's over-rotating to the experienced talent and management teams and delegation. I think he's mostly right about that. People haven't really followed that. People are hiring people from the outside quite a bit. That's kind of the standard part of the playbook that all of them are following now. It's a little different. It's actually quite different than what Brian's espousing. Going back to the conversation around CEOs, a lot of people listening to this podcast, just a lot of people in the world want to be founders. They want to be CEOs. It's hard to figure out their awards unless you're very good at blind referencing. So you tend to overrate them and underrate your homegrown. So if it's pretty close, I think you give your homegrown a shot at it. What's interesting to me, Lenny, is Brian Chesky rethought a lot of this stuff. And he's like, everyone's over-rotating to the experienced talent and management teams and delegation. I think he's mostly right about that. People haven't really followed that. People are hiring people from the outside quite a bit. That's the standard part of the playbook that all of them are following now. It's a little different. It's actually quite different than what Brian's espousing. Going back to the conversation around CEOs, a lot of people listening to this podcast, just a lot of people in the world, want to be founders. They want to be CEOs. At the same time, you look at Elon, you look at Jensen, you look at Steve Jobs, you look at you. A lot of people are like, I can't. I'm not this person. I'm not going to be as good as them. There's no world where I'm this good. Do you feel like there are specific profiles or just traits that you have to be born with to be a successful CEO? Or do you think it's all learnable? Anybody can be successful if they really work hard? At Sequoia, I meet all these CEOs coming in. And I have a little root-like algorithm in my head. And I look for four things. I call it my LOCK algorithm. L is for lovable. And Steve Jobs, you would say, is rough and maybe not lovable, but he would inspire followership. You would want to follow him. And so could I envision a 28-year-old me graduating from business school, going to work for this person? Would I crawl across broken glass? That's question one. Two is just obsession. Are they deeply obsessed with this problem? I'm a little negative on people who came up with this problem to solve six months ago and started a company. I like people with deep founder-market fit. They've been thinking about it for a long time and have evidence in their lives of going deep down, obsessively down a rabbit hole, because that's what it takes to be a founder CEO. The C is something I wouldn't have thought of, but this is a Sequoia thing, like chip on the shoulder. Pretty much all of them have a bit of a boulder on their shoulder. And I have a bit of a chip on my shoulder too. And the K is just for deeply knowledgeable about the domain. And so I look for that. If I were to stick an S on it, I would say student. I look at Winston Weinberg from Harvey or James from Profound or Gabe from Rogo, some of these new, very fast-growing companies. They're students of the game. They're not just know-it-alls. They're deep, deep, deep, deep students of the game. And they're like LLMs. They're constantly, constantly learning. And it's not just learning stuff from me and their peers, but they go way back in time and have a lot of history on stuff. So those are some of the, that's my little criteria I use when I'm evaluating CEOs. What do you look for, by the way? You've interviewed a ton of folks like me. What do you think's in common? Of successful founders? Oh my God. I wish I had my succinct answer. I would ask, I would go to LennyBot.com and be like, what is the common pattern across these folks? One that you didn't mention that I think is interesting, I did some research on this recently with Terence Rohan, one is just extremely ambitious, just trying to do something really wild that most people are like, that's crazy. You're not going to get a subscription service for all music in the world. What are you doing? And you're not going to build it. I agree with that. And is it learnable? I noticed a lot of the CEOs struggling with a couple of things. Let's say you're Winston, you're late twenties, you've never managed a team. You've probably never even been captain of a sports team before. And in order to scale, you have to give people feedback constantly. And it's very unnatural. It's like, I'm going to give this VP I hired a bunch of feedback, positive and negative. And if you don't get good at that, you really pay the price later. That's something I think they have to learn. They all have to learn to get a good bullshit detector. They're constantly being spun. Everyone's trying to sell to them. The org is always trying to sell to them. So that's something they have to develop over time. They have to all get good at the inspiration thing over time. You're Winston. You've never had to inspire anyone in your entire life. You went to school and you're a lawyer for a few years and you started this thing. Inspiration wasn't your thing. So there are certain things you have to learn on that startup-to-scale-up path. And the best ones learn it very fast. This is extremely interesting and useful. So LOCK with an S at the end, just to mirror back what you're sharing. When you were saying you evaluate CEOs, is this for investing as a, okay. So when you're helping Sequoia decide, should we invest in this company, what you look for is LOCK. I like the S, so I'm going to include it there. So are they lovable? Are they inspiring? Are they obsessed with this problem they're going after? Do they have a chip on their shoulder? Are they extremely knowledgeable about the problem they're going after? And it sounds like not just the problem, but studying companies, business strategy, things like that. And then S was a student. I guess that's what S is. Student is studying this, being a founder, being a CEO. Okay, so I guess going back to the question, do you think, just to put it very simply, do you think CEOs are born or do you think they're made? Can anyone turn into an amazing CEO? I don't think anyone can do it. I don't think it's just anyone. I will say I've noticed that. So another little rubric I have, and I don't see a lot of these, but Brett Taylor's one, there's a few out there that are in Sequoia's portfolio. I call them, back to the baseball thing, a five-tool player. In baseball, when you rank a player, it's can they hit, can they hit with power, can they run, can they catch a ball, can they throw the ball. And they rate them one to 10 at each. And it's very rare that you have a five-tool player, extremely rare. And the thing that's new now is there are five-tool CEOs. Brett Taylor's one. You can code, you have taste, you have vision, you can sell the product, you can convince employees, this kind of super CEO. And there's a bunch of them now. And I don't know, I didn't see a lot of those. That certainly wasn't Steve Jobs. He wasn't programming. It wasn't Jeff Bezos. I think there's a new breed that's quite impressive. These folks you mentioned, were this good before AI became a thing? I imagine AI helps more CEOs fill the gaps that they have. I think AI, it's hard to fill the gap. This guy's a developer, he's brilliant, genius-level, obsessive, but can he convince, can he sell? Can he convince an investor to give him a lot of money at a high valuation? Can he convince brilliant employees to leave OpenAI and join him? Can he convince some big skeptical Fortune 500 enterprise to buy his product? Being able to do that and have taste and be able to code really well at next levels, I think, is rare. I actually think it might be the other way, though, where mere mortals like me, who can code, all of a sudden we're going to be able to build stuff. I think it goes the other way. I love this list you shared of things that you find CEOs most have to learn: BS detection, inspiring people, giving hard feedback. What's the one thing that most often people who become CEOs, founders, have to work on? Is there a most common thread of, here's the thing you probably need to work on most? It's that feedback thing. All of the CEOs are building their teams, and so many are like, I have a co-founder that runs product and engineering, but I need that co-founder to step aside and be the CTO and the thinker to code really well at next levels, I think, is rare. I actually think it might be the other way, though, where mere mortals like me, who can code, all of a sudden we're going to be able to build stuff. I think it goes the other way. I love this list you shared of things that you find CEOs most have to learn: BS detection, inspiring people, giving hard feedback. What's maybe the one thing that most often people that become CEOs, founders, have to work on? Is there a most common thread of, here's the thing you probably need to work on most? It's that feedback thing. All of the CEOs are building their teams, and so many are like, I have a co-founder that runs product and engineering, but I need that co-founder to step aside and be the CTO and the thinker and the labs person. And I need to hire somebody who can actually run the engineering machine. So many of the CEOs are going through that right now. That's a tricky transition. So many of the CEOs are layering folks. You hired that early head of sales. He hired 10 people, but just can't quite figure out the sales profile, can't quite unpack the sales process, can't quite forecast accurately. We need to layer the person. Those types of conversations are very tricky and quite unnatural for homo sapiens to have if you're 25 and you've never done anything like that before. So I see the best ones getting really good at that and studying it. And it's super uncomfortable, but they have to suck it up and get good at it. What do you find most helps them build these skills, get better at this? Is there some tidbits of advice you give them? Is it something that they study to improve? I think misery loves company on this. So what I do, the kids table is 15 CEOs of companies under a hundred employees, and the adults table are CEOs of companies over a hundred employees, about 15 of them. They talk about this with each other. It's a safe space, and I can weigh in, but it's actually much more effective when their peers weigh in. I think misery really does like company on stuff like this. They learn from each other. Okay. So essentially it's find peers to talk to and share and be more open. And the reason I break it out is the problems with the kids table are very different than the problems of the adult table. And they all rhyme. They rhyme a lot. So you teach a course at MIT around scaling startups, and it's specifically around scaling, not startups, not starting the company. And you have this quote in your syllabus: starting a company has never been easier. Scaling one into a durable, high-impact organization has never been harder. Why is that the case? I mean, has it ever been easier to start a company? That's absolutely true. And the flip side of that is, I mean, the number of companies formed is going to mushroom over the next 10 years relative to the last 10 years. And the last 10 years compared to the previous 10 years has mushroomed. I just think in my life, like I'm old. And when I was a kid, I'd walk into CVS, corner drug store, and I want to buy a toothbrush. There are four or five there. You pick one. And in the nineties or 2000, you go to Amazon, there are four or 5,000 toothbrushes. It's more 5,000 companies creating those toothbrushes. It got much, much easier to make stuff, and even technology. AWS just made it easier to start a software company. So it's a huge jump back then when we started up to about 2006, but now it's going to be an even bigger jump. So it's easier to start. Now there's so much noise and competition. It's just going to be hard to stand out and really accelerate and scale. So that's why I say it's never been easier to start. There's never been more competition. It's never been harder to scale. And a big part of this is distribution, essentially breaking through the noise, is what I'm hearing. It's hard to learn that. You didn't grow up doing distribution. You don't know. So they're all learning it, and the ones that learn fast, it's like a learning game. The faster you learn, the better you do. Along these lines, I said you tweeted this recently where people talk about which jobs AI is going to replace, and you said that sales is maybe the last job AI will replace. Why do you think that's the case? Well, if you look inside a typical enterprise, where's AI really working? Let's say inside a HubSpot, software development's working incredibly well, customer support incredibly well, legal starting to work incredibly well, but there really aren't apps in the rest of the org that have really changed things a lot. And then the go-to-market side has been slow, really just support. There isn't a canonical marketing or sales, or maybe the BDR is the first one, but I think ye olde enterprise sales, where there's actual trust built up between two carbon-based life forms, I think will be very, very, very late to go in the white-collar world. I also think a lot about the go-to-market. I think the go-to-market is going to get turned on its head. When we started HubSpot, if I think of the way the funnel worked, you want to get found in Google, someone clicks on a blue link, they land on your website, they go down the rabbit hole, they clicked on contact sales. They wait until that sales rep's ready, go down that rabbit hole. And I think it's going to get turned on its head where people are evaluating a product. They start in Gemini, or they start in Anthropica, they start in ChatGPT, and ChatGPT knows everything on your website, everything beyond that, knows all your competitors. So they will stay in there and do lots more research and be incredibly well educated. So your website's a lot less important. And they go to your site. I think sites will change where you're going to have a really high-quality avatar that knows everything about your products, knows everything about your company and your pricing and packaging, and you can have a high-quality conversation with that person. That person will get stored in your CRM and will get scored as a good-quality conversation. And then the sales rep will follow up. But that sales rep will bring an avatar with them on every sales call. You don't have to wait for their SE. They'll have their own SE that's all-knowing that will follow them through the process. So go-to-market hasn't changed much yet. But I think over time, it's going to change a lot. This avatar just understands. So this is the buyer has their own little agent that comes with them, or on HubSpot, you have this avatar that walks you through the sales process. I think both. I think me as a knowledge worker, what I really want as a homo sapien is I have a Delphi clone that I really like. Same. It's actually quite good. Yeah. You have one too. Yeah. Yeah. Where do people find yours? They find it on my footer. They can find it on Delphi. Okay. We'll link to it. Yeah. And what I want is connect that thing to my email, into my granola, into my plod, and it knows everything about me. And then when I go to a meeting, Lenny, I want to invite that thing to my meeting. So it's sitting there in the Zoom meeting, not just taking notes like granola, it's a participant. So if I forgot something, I ask it a question. If somebody else forgot, I think every knowledge worker will have one of these in three, four, or five years. But mine was more on the go-to-market side, where I think every website will change, and there'll be an all-knowing avatar on that homepage. And if it's a considered purchase, I think it gets handed off to a sales rep. That sales rep has a conversation, but when that sales rep's on Zoom, they have their SE avatar, this all-knowing. And so I think this stuff all changes a lot in the next few years, but it hasn't really unlocked yet. What are we going to be doing in this world? These two bots chatting with each other? It's going to be great, Lenny. You and I are going to be sitting, relaxing on a month-long vacation, sending our avatars to all meetings. Go buy me some HubSpot seats, please. I think this is why CloudBot was so popular. I think this is essentially what they're building, this idea, which is now called Moldbot, which might be changing will change, and there'll be an all-knowing avatar on that homepage. And if it's a considered purchase, I think it gets handed off to a sales rep. That sales rep has a conversation. But when that sales rep's on Zoom, they have their SE avatar of this all-knowing. And so I think this stuff all changes a lot in the next few years, but it hasn't really unlocked yet. What are we going to be doing in this world? These two bots chatting with each other? It's going to be great, Lenny. You and I are going to be sitting on, relaxing on, a month-long vacation, sending our avatars to all meetings. Go buy me some HubSpot seats, please. I think this is why CloudBot was so popular. I think this is essentially what they're building, this idea, which is now called Moldbot, which might be changing again. It's this personal little agent that can go do stuff for you. Totally. So you're talking about the future of go to market as this world where there are these little bots and agents that are doing things for you on both sides. When you look at companies today that you work with that are doing well, especially AI-driven companies, what are they doing differently in terms of go to market that is working really well? Honestly, the only thing that's different today, it's exactly the same as it's been for a hundred years, except they call their SCs or their system consultants forward deployed engineers. The rest of it is the same. I thought it would be totally different in AI. I'm working with all these companies. They're hiring all the same folks, running the same enterprise sales processes. So it hasn't changed that much, at least on the enterprise side. It actually hasn't. I spent the first 10 years of my career at a company called PTC, which is an enterprise sales machine. Enterprise sales hasn't changed that much since the 1990s. Okay. And so forward deployed engineer, very hot term. The idea there is they come work with the customer and help them implement this thing. And that's come up a lot on this podcast. Just with AI tools, rarely are they just plug and play. You can't just set up some agent that figures everything out. It takes a lot of onboarding and integration. Is it actually a different thing at all versus sales engineering in the past, things like that? I think it's a solutions consultant, sales engineer, technical. They help you implement it. They connect all your systems. They customize it. It's different. You're training it in a different way. But I think, anyway, I think the term is fine. I'm being light on it because, boy, it looks similar, except that role has a different name to it. Got it. So if anything, the advice I'm hearing here is just lean into this. Continue to lean into this idea of having your employees help the customer onboard, be successful, integrate all that stuff. I think the thing that will change first is the top of the funnel around getting found. Instead of Google, you've got to get found in these. Yeah. AEO. Yeah, that's going to be really important, and the way you build your website is very different to optimize for it. And then I think your homepage is totally different. I think you land on an avatar and have a conversation with them versus going through all the pages on your site. I think the top of the funnel is about to change a lot. Is anyone doing this well yet? This idea of this avatar, or is this just in the future? This is a two-star program. HubSpot does it. We built one. It's working. Okay, okay. Let me ask one more question around CEO stuff, and then I want to move on to Halliganisms. All right. How is just being a CEO different than it was? So you've been doing this for 20-ish years. Yeah. What's most different about what it was like to be a CEO maybe 10, 20 years ago versus today? What am I seeing? Yeah. Actually, Winston from Harvey said this a year ago, and I was like, that's bullshit. But I actually think he was right. You can just do a lot more. You've got AI agents doing stuff. Everyone's more productive. The software developers are more productive. Something that used to take you a year takes two months now. And so the amount of projects and the amount of stuff you can do is much, much more. I think he's right. I think that's a little dangerous. Let's say you found your beachhead market, and that beachhead market is really good and it's very deep. There's a lot of work to do. I think what's dangerous for companies is that they hop to that second act too quickly, and they lose focus on that first act. And this isn't a completely perfect analogy, but you think of OpenAI and ChatGPT, and it's a consumer app that's doing incredible. And they're doing lots and lots and lots and lots of other things. And then Gemini comes out, and they've focused back on the core. I think there's a lot of competition. Everything's moving fast. I do think people get more done, and I think that impacts everything. The planning cycles used to be a year. I think the planning cycles now are three months long. Yeah, that's a big change. I think it puts pressure on the CEOs to be faster and better decision-makers. I just think of times in HubSpot when things slowed down and there was churn. It was usually my fault. It was because there were some hard one-way-door-type decisions on my desk. And maybe every year I would sit down and I'd open that one-way door or close it. And it just freed everyone up, and we just started moving so much faster. I think people need to be making those decisions and walking through those doors much more quickly than they used to. I think that's new and different, different. I was someone who always valued optionality. I think there's a massive tax in optionality when you can move this fast and try a lot of things. So I do think the job's changing a lot. Yeah. And there are so many reasons this is happening. One is just technology. Every week there's a new shift in what is possible. Yeah. So if you're spending all these months thinking and planning, what a waste of time it ends up being because so much is changing. And I know, yeah, it's hard to keep up. Luckily, we got some sweet podcasts to check out to keep up to date with what's happening. We'll link to yours, of course. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercel, Platt, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, SCIM, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed-stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unlocking growth. They're essentially Stripe for enterprise features. Visit WorkOS.com to get started, or just hit up their Slack support, where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and a smooth developer experience. Go to WorkOS.com to make your app enterprise-ready today. Let's talk Halliganisms. Essentially, these are nuggets of wisdom and advice that you find yourself sharing often. You've written about a bunch of these online. And so let me just go through them, and then just share the synopsis of the advice and the lesson around this Halliganism. The first is when you have to eat a s**t sandwich, don't nibble. Okay, I completely stole this from Ruth Porat, the CEO, the CFO of Google. I saw her quote somewhere. I'm like, that's it. She's put a perfect thing on it. And I'll give you an example where I think this will play out over the next couple of years. I think within the next couple of years, there'll be a real retrenchment in valuations, and some will live up to valuations a lot. Well, if I look at the public markets, they're very tight right now. It's like the anti-bubble. I look at private valuations. It's a real bubble. I think there's a reckoning somewhere down the road. And a lot of companies are going to have to do layoffs. It's never fun. It's usually the worst thing in the history of your life. And the temptation is to do, well, just do a little one now and we'll grow into it. And then they do another one in six months and then another one. I think with everything, including this type of thing, it's just rip the darn Band-Aid off, this will play out over the next couple of years. I think within the next couple of years, there'll be a real retrenchment in valuations, and some will live up to valuations a lot. Well, if I look at the public markets, they're very tight right now. It's the anti-bubble. I look at private valuations. It's a real bubble. I think there's a reckoning somewhere down the road. And a lot of companies are going to have to do layoffs, a lot. It's never fun. It's usually the worst thing in the history of your life. And the temptation is to do, well, just do a little one now and we'll grow into it. And then they do another one in six months and then another one. I think with everything, including this type of thing, it's just rip the darn Band-Aid off, tell everyone the bad news. They're adults. They can handle it and get it done. And I think people avoid that. I think that's good advice Ruth Porat's giving. Because you're going to have bad news to deliver. Bad shit's going to happen to your company, even though it looks like it's going amazing right now. Weird stuff's going to happen and you're going to have to deal with it. And we had a lot of weird stuff happen at HubSpot. And there's a basketball coach named Mike Shischewski. He's Duke's basketball coach, all-time winningest college basketball coach ever. If you go to a Duke basketball game, you can hear him yelling from the sidelines, let's play, let's play. And what's going on there is when a college basketball player is playing in the game and takes a shot and clanks it off the rim and misses it, they have a strong tendency to go play overly aggressively on defense in the backcourt and many times compound their error by making a foul or something like that. And what he wants is for people to make their error, forget about it, and move back down the other side of the court and run the play. And so we used, actually, there were times in HubSpot's history where we had Mike Shischewski's face on a huge slide in front of the company meeting saying, next play, because there was an unforced error and we needed to deal with it and move on. Is there a story of that that comes to mind that is interesting and worth getting into? There's a lot of them, but I remember in 2000, it was the end, it was the last day of March in 2019, and we had a really bad outage all day, and we never really had one of those. And it was bad. Customers were unhappy. A lot of customers canceled. I had a lot of customers yelling at me. And I remember that company meeting, I cried in front of the whole company. I couldn't believe it happened to us. And I remember using the next play slide on that one. Yeah. Most of the, we made a lot of mistakes at HubSpot. A lot of bad things happen to companies, and most of them were self-inflicted. And a lot of them are the old saw, like companies are far more likely to die of overeating than indigestion. Usually it was we were trying to do too much. I haven't heard that version. I've always heard most companies have suicide versus homicide, indigestion. That's true too. Oh man. Okay. So next halogenism, never waste a good crisis. There's something that people hear. I'm curious, what's the lesson here? And then is there an example of this where you learned this lesson? I'll just follow on to most of the good things that happened in HubSpot came out of a crisis because we would take pretty drastic measures to fix it and make sure we didn't do the same thing again. And so in this particular case, we really rethought how we deployed software, how we thought about making software in a way that was incredibly healthy. And we haven't had a serious outage since. The quality is much better. And kind of an interesting thing with HubSpot is we started as a marketing software company, and we pivoted. We had Salesforce kind of come into our market. We put in a CRM. And one thing that we, if your marketing software goes down, if there's a bug in the workflows or something like that, it's bad, but you survive it. You wait a little bit. If your CRM goes down, particularly the last day of the quarter, you're really impacting your customer's ability to do business. So that was a mindset shift that we hadn't quite come to terms with, of how important we were to our customers. And so we made a lot of changes based on that crisis. Good things come out of crisis. Usually very good things came out of crises. So there's a lesson there. Something's going wrong. Is it just overcorrect? Use this as a way to get things? Yes, we always overcorrected. Yeah, we purposely swung the pendulum hard the other way. Hmm. Which connects to the first halogenism of if you're eating a shit sandwich, no nibble, just, it's almost like go all the way, go even further. Yes. Make it really obvious to everyone what's going on. Hmm. Okay. Another halogenism. If you want to kill a plant, have two people water it. I love this one. It's very true. Let's say, Lenny, you bought a new beautiful plant for your office. And then you went away for a month to Turks and Caicos because your AI agents were doing your podcasts, and you asked two of your friends, hey, would you mind watering my plant? And there's one of two outcomes. What happens to the plant? The plant would either be overwatered and die or not watered at all and die. And every CEO in the adults' table has gone through this, and they are religious about the DRI. Everyone talks about DRI at the kids' table, but once it gets to the adults' table, people get deep religion on it. And I think it makes sense. When you're small and you're in startup mode, everyone's in the room, everyone knows exactly what's going on. So let's say you're running a pilot project with a big account. You're running that pilot project. Everyone's on the same page, a salesperson and service person, developer, everyone's on the same page, and you go out and do it. Yes, Qtobel. When you get to scale, you get a sales organization, you get your forward deployed engineer organization, you've got product management organization, you've got some developers working on it. Everyone's separate. No one knows really what's going on in the other departments. And so let's say you want to really have a good pilot process. You want to rethink it because you're scaling. Everything important happens cross-functionally inside a company at scale, and you need someone powerful to own it. So let's say it's a salesperson. They need the power to tell people in other divisions what to do, even if they don't own it. So almost every CEO I deal with is a zealot on the DRI idea. And it doesn't bite you until you get to some sort of scale. And to be super clear about that advice here, it's one person is responsible for a goal, a metric, some outcome you want, versus you may feel like, okay, we have two people on this. It'll be awesome to work together. Your advice here is that doesn't work. Committees never work. Yes. Yes. And DRI is directly responsible individual. Hmm. The way I always thought about this is just having someone's ass on the line for something makes them so motivated to get it done versus spreading the responsibility and the upside and the downside. It just doesn't work. I totally agree with you. Awesome. Okay. Another algorithm. I don't know if you put it this way. The way I think about it is this idea of there's no such thing as a silver bullet. It just takes a lot of lead bullets to get something done. I think the way you wrote about it is it's always one step forward, two steps back. Talk about your advice there. Yeah. I always thought incorrectly that we would have one hire or one investor or one event or one product release that would, I was wrong about this, but it'd be a silver bullet. And the reality inside the HubSpot machine, the way it felt to me, it looks from the outside like over a long time, up and to the right and smooth, but inside it was two steps forward, one step back, two steps forward, one step back, two steps forward, one step back. And a lot of times it was a crisis that caused that step back. So we just didn't have that. I there's no such thing as a silver bullet. It just takes a lot of lead bullets to get something done. I think the way you wrote about it is it's always one step forward, two steps back. Talk about your advice there. Yeah. I always thought, incorrectly, that we would have one hire or one investor or one event or one product release that would, I was wrong about this, but it'd be a silver bullet. And the reality inside the HubSpot machine, the way it felt to me, it looks from the outside, over a long time, up and to the right and smooth, but inside it was two steps forward, one step back, two steps forward, one step back, two steps forward, one step back. And a lot of times it was a crisis that caused that step back. So we just didn't have that. The thing about being a founder CEO is there's no one, especially when you're in your twenties, there's no one there to rescue you. Your parents aren't going to rescue you. Your VC is not going to rescue you. Your teacher, your thesis advisor, you're on your own, and you got to figure it out. And that hits you when you hit your first crisis. It's on you. You can get some help, but it's on you. Sometimes they have you in their corner, if they're lucky, at Sequoia. I can't solve it. Oftentimes I can be the shoulder they cry on, and I can give them advice, but it's still on them. Do you feel like too many people start companies? When someone comes to you, like, hey Brian, should I start a company? I have this idea. Do you often just say, no, you have no idea what you're getting into. This is going to be much more painful. I heard Jensen Wong say that. Like, I wouldn't start NVIDIA if I had to do over. If someone asked me that question, I would start HubSpot over. It was very hard. There were a lot of sacrifices. It wasn't glamorous at all. But at the end of the day, I'm incredibly proud of it. And on my deathbed, I'm going to look back and really enjoy it. And the Dalai Lama has a good expression, live a good life so you can live it again on your deathbed. And I'm really glad I did it. But I do talk a lot of that, that some opportunity, they don't want to waste the opportunity, so I think that mindset's right. But people today are much more hardcore than they were in my era. I worked hard, and I was probably 60 to 70 hours a week the entire time, never really turned it off, but that's kind of how I thought about it. It's different now. People are much more focused, and I think Elon's inspired people. I had a startup back in the day, nowhere near as successful as HubSpot, but the way I thought about it is, let me just give it everything I have and see what I can do. This isn't a shot. This is my chance. Let me just give it all. Forget balance. Just go for it seven days a week for a while, and then you scale back. And it's just such an empowering thing to do for a while. Let me just try. I'll give it everything. This won't be forever. Yeah. And I know you've written about this. Balance for CEOs is not, you should not have work-life balance if you want to be incredibly successful. I don't know if that's always true, but how do you talk about that to founders? I don't know any of the founders I work with that have work-life balance. By the way, this is not something I recommend. I didn't have it. I don't think my co-founder Dharmesh had it. The only CEO I know, and he's unusual in this way, is Kareem from Clay. He's like, nope, you need balance. Take the weekends. He's got a different mindset. I'm going to have him on my pod to talk about his mindset, but he's sort of the outlier. Everyone else is really, really obsessed, and they really don't have much of a life. It did take them a long time to find product-market fit. It did definitely pre-AI. I wonder if there's a correlation. But it did work out so great, so it is a good lesson. Okay, a few more here. One is a math formula: EV is greater than TV is greater than MEV. What is that? Okay. EV is enterprise value. TV is your team's value. MEV is your value. And as HubSpot was scaling, and we had a lot of people who were VPs in different roles, and they started to get good-sized organizations, where they would fall down was they didn't solve for EV, but they'd solve for TV over EV. They'd solve for their own team. So let's say they ran sales. Let's say, I just want bookings to be as high as possible because I get paid on bookings, and the service team can handle all the downstream problems I created. Marketing to sales, between every department, this happened. The kind of immature managers who didn't scale really solved for themselves, and some, as they solved for themselves, kind of sub-optimized for their peers, and their employees would notice it and complain about it. It would be fine in the short term, but it would show up. And the place it would show up, Lenny, was we did, and I think a lot of companies do this now, but we did a quarterly employee net promoter. We did a quarterly customer net promoter survey and a quarterly employee one, and we would have people rate it by the department they're in. And one interesting thing about that, so it's like sales and service and engineering, all the different departments, and we had an overall net promoter score, and then each department had a net promoter score. Let's just take sales. Sales net promoter score was like 65, 62, 68, 30. Oh, that's a big drop. And then you read the comments, and it was not good. A lot of complaints about the leader of that, and a lot of the complaints were a little bit of this TV thing. And then we'd give feedback to that VP, would help them, we'd give them all the comments, be like, you got this. And then a quarter later, it went from 30 to negative 5. They almost never recovered. You lose your team, you kind of can't, it's hard to get them back. And that's why I say, hire slow, fire fast. And this doesn't show up in the first 100, 150 employees. Everyone's solving for EV. But as it gets bigger, and the CEO doesn't know anyone, and there's a couple layers between you and the employees, they tend to solve for TV. So we always put on the wall, solve for EV over TV over ME. And then we added CV in front of EV: solve for the customers first, then for HubSpot, then the employee, then yourself. That was very helpful to us. Yeah. I imagine everybody listening, working at a big company, understands this, where you have goals, you get your KPIs and your performance reviews based on what impact you drive, if you hit your goals, and so everyone's incentives are focused on my goals, and drive those, and I don't care about other people's goals, the company's goals. Steve Jobs had an interesting line. He says, you don't work for your boss, you work for Apple. I thought that was pretty good. I heard that after I was CEO of HubSpot, but that kind of captures the sentiment, and that's how I felt about HubSpot. You work for HubSpot first, and then you work for your boss. This is hard because people's performance reviews are based on their goals, KPIs. It's always like, here's what I got to drive. Other than putting posters on the wall, and this is our, just HubSpot growth above all is what matters, our customers, I guess in your case, is there anything tactically that was useful in helping people put enterprise value first? This was explicitly called out in the form for the employee. When you got your review, this was part of it. So they'd get a score of one to, I forget, 10 on that. I would talk about it constantly. And when we first started HubSpot, I ran it a little bit like Jensen runs NVIDIA, where I didn't do one-on-ones, and I gave a lot of good and bad feedback publicly in large management team meetings. And I definitely would go out of my way to criticize people if I felt like they were solving for TV over EV, and people got a sense for that. And then every quarter we did a really well-produced company meeting. We spent a lot of time on it. At the end of the company meeting, we gave out, we called them the Champagner Awards. It was a bottle of Veuve that my co-founder and I signed, and we'd read something nice about them and give it to them. And usually there was an EV theme in that. So we did different things to kind of beat that into people's heads. Amazing. So here is, just celebrate people that it constantly. And when we first started HubSpot, I ran it a little bit like Jensen runs Nvidia, where I didn't do one-on-ones, and I gave a lot of good and bad feedback publicly in large management team meetings. And I definitely would go out of my way to criticize people if I felt like they were solving for TV over EV, and people got a sense for that. And then every quarter, we did a really well-produced company meeting. We spent a lot of time on it. At the end of the company meeting, we gave out what we called the Champagner Awards. It was a bottle of Veuve that my co-founder and I signed, and we'd read something nice about them and give it to them, and usually there was an EV theme in that. And so we did different things to beat that into people's heads. Amazing. So here is just celebrate people that focus on this and also include it in their valuation performance reviews. Yeah, okay. That's a good segue to another halogenism where you talk about how companies are either customer-centric, employee-centric, or investor-centric, and it's really important to know which you are. And you guys actually shifted there. What's your insight there? Okay. We were very employee-centric, more than customer-centric, in the first several years of HubSpot. So much so that the company was number one on Glassdoor's Best Place to Work. I was the number one CEO in Glassdoor, and as I look back at that, I'm not sure that's a good thing. Wanting to be liked, I don't think, is a good feature of a CEO, and wanting to be the best place to work probably isn't the right way to go. If you look at Tobi from Shopify, his scores aren't that good, but that company is doing really, really well. And so we over-indexed on it. And part of the reason we over-indexed on it is my co-founder was really strong in this, and we had an incredibly powerful head of HR named Katie Burke, and we just worked on it. We spent a lot of time on it. And when we'd have a management team meeting, and let's say it's four hours long, two of the four hours would be on employee stuff. And at some point I was like, why are we spending so much time on employee net promoter scores? Let's say our employee net promoter score was 60 and our customer net promoter score is 25. I was like, I would give up 10 points of employee net promoter score to get 10 points of customer net promoter score. And so over some time, we shifted the center of gravity to customers. We still, of course, worried about employees, but the center of gravity from HubSpot moved very much to customers. And we did that in a few ways. Every time we had a management team meeting, we had our management team meetings once a month, not once a week, and we would have a customer panel come on. In that customer panel, I would run the panel and ask very tricky questions to the customers and pull out the bad news from that. And then we still do this. We have a customer panel at our board meetings. Our whole board can ask questions, and my favorite question is, what do you love about HubSpot? And then what do you hate about HubSpot? And they look at their shoes, and they're like, come on. And it's a great way. So the employee's voice is here. Those company meetings, we have the customers in the company meetings. We changed the comp plan so the management team got paid not on revenue but on retention and net promoter score. And so we worked very hard and swung the pendulum to customer-centric. But I do think companies have one center of gravity or another. There's a really interesting thread throughout this conversation of just what do you want to change how you operate. You have to go really far to a whole other and almost overcorrect. It's really interesting, just how much work it takes to change culture, to change norms. And the bigger it is, the more obvious you have to make it. And the other thing about being a CEO is you got to say the same thing over and over and over and over and over again. It just doesn't sink into people's heads. You have to just be incredibly repetitive on it before it sinks in. Same thing with marketing, but internally that happens. The other weird thing about being a CEO is as it gets bigger, when it's small everyone's giving you shit, and you're all on the same level. But as it gets bigger, you didn't interview everyone. You had thousands of employees. You don't know everyone. And people put you on a pedestal that you don't deserve. And let's say you're in the hallway and you're just kind of shooting the shit with a bunch of people, and you're like, it'd be cool if we had a product that doesn't fuck it up. Somebody inevitably would go home and build that thing. It'd be like, Brian wants this. This is a big initiative. So people really lock in on what you said, and it turns out you have to be very repetitive. You have to be very careful what you say. Darmesh was on the podcast, your illustrious co-founder, and he developed the whole system to avoid the sort of thing, flash tags. We had a whole system because we would say something on an email to the management team or a Slack, and everybody would be like, okay, this is what they want, let's do it. And sometimes it is like, you need to do this, and sometimes it is like, we should talk about doing this, and sometimes it is, this is just an FYI, we're thinking about it. And because it got big, we came up with that rubric. We needed to tag each email with how do you want me to get this done this week, or is this something we should talk about, or is this something that's just FYI, I'm thinking about. That's what I was like. One of them is plea. I'm pleading you to do this. I'm not telling you to do this. I'm just pleading that you do what I ask. Oh man, okay. I like this. All this all connects. And by the way, you guys were co-founders for 20 years. You shared something before we started recording. Darmesh famously did not ever want direct reports. He's just like, Brian, I want to start this with you, but I don't want to ever manage anyone. And you were talking about how you had to take on engineering, which didn't make any sense. Oh, I'm an engineer. I can code, but it's not good. And so when we started the company, he's like, I was a CEO before. I was terrible at it. I want to do it again. You're going to be the CEO. I'm like, great. And he's like, and by the way, I'm not going to have any direct reports. I'm like, well, it's just the two of us, so don't worry. But it's like, no, ever, never. I'm like, yeah, yeah. And then we get 10, 12 people, we're starting to hire engineers and onboard them and making big decisions, and I would go to him and be like, well, can you manage him? He's like, don't you remember I told you I don't want to have any direct reports? It's like, surely you were kidding when you said that. He said nope. Darmesh Shah has never had a single direct report at HubSpot. Incredible. I don't know. It's just like a dream, a dream, a way to operate. I love that you made it possible for him, and it created all this opportunity for him to tinker. Yes, yes. Freedom to really think and be creative. Yeah. I'm excited to get him back on the podcast someday. We're going to link to that episode. Maybe a last question. I'm curious if there's anything else you think we missed. As a company grows and scales, the job of a CEO changes. You've written a bit about this, of just how different the job is when you're a starter versus a scale-up. What are some of the things that most change where your time goes as a CEO as the company grows? I clicked on this earlier, but that inspiration thing. I have a little rubric where it's like, in the startup phase it's 90% perspiration, 10% inspiration. You get to the scale-up phase, it's 90% inspiration, 10% perspiration. And over time, you're doing every job in a startup, and you still need to be very attached to it, and you still need to talk to customers. You can't give it up. But man, you have to let go of so much stuff over time in order for the organization to scale. And I have trust issues. I only trusted a small number of people at HubSpot to be a DRI, to really drive something important. It drove people crazy that I didn't have a larger trust surface. Every one of the CEOs I work with has the same problem, and that's a scaling limit. That was the limit for me. I wasn't trusting enough. Brian, I feel like I could chat with you for hours. There's a whole list of halogenisms I'm going to link to that we didn't even touch on. But before we get to our very exciting lightning round, is there anything else that you think we should chat about, anything you want to leave listeners with? I would say if you're a CEO and you're interested in scaling, I think the Halogen, as opposed to all the mistakes I made in my 15 years being CEO, I tried to summarize in there to help you avoid them. And I have a pod. You should first listen to Lenny's pod because it's amazing, but I have a pod just for crazy that I didn't have a larger trust surface. Every one of the CEOs I work with has the same problem, and that's a scaling limit. That was the limit for me. I wasn't trusting enough. Brian, I feel like I could chat with you for hours. There's a whole list of Halogenisms I'm going to link to that we didn't even touch on, but before we get to our very exciting lightning round, is there anything else that you think we should chat about, anything you want to leave listeners with? I would say, if you're a CEO and you're interested in scaling, I think the Halogen, as opposed to all the mistakes I made in my 15 years being CEO, I tried to summarize in there to help you avoid them. And I have a pod. You should first listen to Lenny's pod because it's amazing, but I have a pod just for CEOs called Long Strange Trip where I interview CEOs about this. Lenny's interviewing me about being a CEO. I get to interview other people about being. I'm kind of a CEO geek these days. And the name of the podcast is a Grateful Dead reference, which we haven't touched on, but you're a huge deadhead, as they say. Yes, that could be a whole other podcast conversation. I think they're sure actually, because I wrote a book called Marketing Lessons from the Grateful Dead, and there's so much. The Grateful Dead were the ultimate Silicon Valley startup. They started in 1964. Do you know where they started, Lenny? No. Palo Alto. Their early concerts were at Stanford, were all over Silicon Valley. They're a Silicon Valley company. They were very first-principles in their thinking. They created a new category, a new way to distribute their music. They disintermediated the ticketing companies. Very innovative. Steve Jobs and Jerry Garcia are very similar in my mind, real crass people. So I think of them as a great Silicon Valley success story. You said you had a whole book about this. What's the book called, just in case people want to do your marketing lessons from the Grateful Dead? Amazing. And I read that you bought Jerry Garcia's guitar for a large sum at some point. Yes, I did, and I consider myself the steward of his guitar. It gets played, like Dead and Co played it, and there's a million Grateful Dead cover bands that let them play it, but I'm taking care of it for the deadheads. What's one nugget of wisdom or lesson that people can take away from the Grateful Dead for startups? Okay, people talk about spiky teams. The Grateful Dead team was interesting. Garcia himself was a bluegrass guy. He was a banjo player. And then Bob Weir, recently passed, was kind of a country crooner, liked country music. Then their bass player was an avant-garde jazz trombonist, Phil Lesh. And their keyboard player was a guy named Ron McKernan, Pigpen, and he was a harmonica guy. And the drummer was a marching band drummer. So, spikiest of spiky teams came together and made a new genre. They created a new category of music. It wasn't rock and roll, wasn't Rolling Stones, it wasn't Buddy Holly. It was this new thing. And then they called it a jam band because they played rock and roll in a bluesy, open, organic, kind of jazzy way. So, spiky teams in creating categories: underrated. Incredible. Are you one of these people that have been to 100 Grateful Dead concerts? Makes sense. Okay, this could be a whole podcast, but we're going to move along. Okay, with that, we've reached our very exciting lightning round. Brian, are you ready? Let's do this. Fire it up. I've watched you do the lightning round so many times. I'm psyched. I'm flattered. Unsurprising questions: what are two or three books that you find yourself recommending most to other people? I haven't read a book in a long time. I listen to podcasts, I'm on X, I talk to a lot of other CEOs. I can't remember the last time I actually sat down and read a book. Much respect. I had Marc Andreessen on recently, and I don't know if you've heard his whole thing on what he consumes. He talks about how he has a very barbell strategy to media. It's either Twitter or books that are 10 years or older. And I've heard him say that. I'm hearing, yeah, I kind of stopped reading. I looked at that. I was getting ready for this, Lenny, and I was like, I can't remember the last book I read. I think this is going to make a lot of people feel better that don't read books. All right, this is okay. Favorite recent movie or TV show you really enjoyed? I love the new Ken Burns, very long, very good Revolutionary War documentary. He's a craftsperson. It's exceptionally well done, and what I like about it is America is really a disruptor startup. So many startup lessons from those. They're gutsy. Talk about two steps forward, one step back. They got into the details of how George Washington ran the army. We were very close to losing that war most of the time. Two steps forward, ten steps back. Two steps forward, ten steps back. Lots of lead bullets. Unless we had alliances, like we had alliances with the French, we were screwed. So I love that. It's a long one, but it's really good. How long is this? What are we getting? Probably 10-plus hours. 10-plus hours. What? It's a lot. But worth it is what I'm hearing. I'm in Boston. It's Revolutionary, surrounded by history. All right. Favorite product you recently discovered that you really love? I love my Delphi clone. I teach a course called Scaling Entrepreneurial Ventures, and I don't do office hours. I have Delphi do my office hours. Very happy with that. My favorite feature of Delphi, and again, lennybot.com, there's my Delphi. I know we both have little bots. The voice feature is the coolest thing, right? Great, not good, great. I can't wait. I had video. They got rid of it. They're going to bring it back. Can't wait till I have this video. My least favorite, my lowest-MPS product is my Sonos system. You have Sonos? I do, and I get you. Yes, painful. Yeah, it's so good in so many ways and so annoying in so many ways, but we still use it. There's nothing better. You're not a competitor. You and I should start a Sonos competitor. No, we should not. That's bad. I'm not doing this. And just to be clear what these bots are, just so people understand how cool this is: my entire thing on every single podcast, like this one, is going to be sucked into it, and every single newsletter, and you just talk to it and ask it, like how do I find product-market fit, and it's based on everything I've ever shared. Here's your steps. Okay, what's even better about it is you can go to ChatGPT and say, what would Lenny think about this? What it's added is the ability to put a bunch of documents in there that aren't on the internet. I put my lectures in there, and there's a new feature where it asks you questions and it kind of interviews you. So it's pretty proprietary. It's getting better. I like it a lot. Yeah, to that point, I haven't promoted this feature of it, but it's trained on all my paid content too. So even if you're not a paid subscriber, you get access to all the things I've ever shared. No, let's not tell too many people that, because one day I'm going to paywall it in the near future anyway. Enough about that. Do you have a favorite life motto that you find yourself coming back to in work or in life? This isn't lightning, but four years ago I had a very bad snowmobile accident. Drove a snowmobile up a cliff. The snowmobile smashed into a million pieces at the bottom of the cliff. So did I. I laid at the bottom of that cliff for a while. I was unconscious for a long time. I woke up, and I didn't think I had my phone, so I sat there for a long time like I'm probably going to die tonight. No one knows where I am. It's frigid out. It's in Vermont, and I'm going to freeze to death. And sitting there for a couple hours, I finally was like, oh, I do have my phone, dialed 911. By the way, 911, amazing service. And so the helicopters came in and took me out, took me to the hospital, and lots of surgeries, and I was kind of out of commission for a year. And you can't see it, but I got metal all over me, all in me. Life's short. Life's short. And I made some decisions at the bottom of that cliff. One of the decisions I made at the bottom of that cliff was I don't really like being CEO of an 8,000-person company. It doesn't really suit me. My harmonic motion is off. I don't love the day-to-day. If I make it out of here alive, I'm out. And so that's exactly what happened. The first big thing that happened coming out of that was I gave the job to Yamini, who's still the CEO doing a great job. So life's short. Don't waste it. I heard this story, but it's just as powerful hearing it again. Why do you think it takes people, why does it take a moment like that to help someone realize this, I need to change? Or just, I think people think they're I got metal all over me, all in me. Life's short. Life's short, and I made some decisions at the bottom of that cliff. One of the decisions I made at the bottom of that cliff was, I don't really like being CEO of an 8,000-person company. It doesn't really suit me. My harmonic motion is off. I don't love the day-to-day. If I make it out of here alive, I'm out. And so that's exactly what happened. The first big thing that happened coming out of that was I gave the job to Yamini, who's still the CEO, doing a great job. So life's short. Don't waste it. I heard this story, but it's just as powerful hearing it again. Why do you think it takes people, why does it take a moment like that to help have someone realize this, I need to change, or just, I think people think they're going to live forever, and they're not. As somebody who's 58, yeah, life's very short, and I'm much more intentional about the decisions I make, much more intentional about the people I hang out with today than I was before that, and I really try to work on things that bring me joy, like this pod. Same. I appreciate it. I read the 20 broken bones in this accent. A lot of broken bones, a lot of metal. I got 33 screws in me, one loose one up here, Lenny. Same. Okay, last question. We talked a bit about the Red Sox. You're a part owner of the Boston Red Sox now. What's something that would surprise people about how a baseball team is run, or just what it's like on the inside of a team like the Red Sox? It's not as profitable as people think. People think these rich guys come in and buy these teams, but the way the league is set up and the way the economics are set up, it's not a profitable endeavor, whereas other leagues are much, much more profitable. Baseball's also deeply flawed. It doesn't have a salary cap, and so you've got the Dodgers, who I take my hat off to, have a 400 million dollar payroll, and the Miami Marlins are like a hundred million dollar payroll. In other leagues, that all kind of balances out pretty well. Baseball, it's set up incorrectly. I think it'll correct in the next couple years, but it's a broken model. Intriguing. Stay in AI SaaS if you want to make money, is what I'm hearing. Vertical SaaS. Brian, this was incredible. Covered almost everything I was hoping to cover. Two final questions: where can folks find Aline if they want to reach out, where they find the bot, how do they work with you if they wanted to, or do I have to be a Sequoia founder? And then how can listeners be useful to you? I came with two things. I would love folks to listen to Longstream Trip, my pod, and I'd get some comments, but not a ton. Lenny, you have more comments than yours. I'm jealous. I'd like feedback on how I'm doing. It's very new, and I just started a couple months ago. It seemed like it's going pretty well, but it's my family and Sequoia people giving me feedback. I'd like to see how all of you, what you think about it. So that would be spectacular. All right, so hop on your YouTube and leave some comments about what they think. The real, real honest feedback. Okay. Brian, thank you so much for doing this. Appreciate it. Appreciate it. Thank you. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennys podcast.com. See you in the next episode. with delightful APIs, comprehensive docs, and a smooth developer experience. Go to WorkOS.com to make your app enterprise-ready today. Let's talk Halliganisms. Essentially, these are nuggets of wisdom and advice that you find yourself sharing often. You've written about a bunch of these online. And so let me just go through them and then just share kind of the synopsis of the advice and the lesson around this Halliganism. The first is when you have to eat a s**t sandwich, don't nibble. Okay, I completely stole this from Ruth Porat, the CEO, the CFO of Google. I saw her quote somewhere. I'm like, that's it. She's put a perfect thing on it. And I'll give you an example where I think this will play out over the next couple of years. I think within the next couple of years, there'll be a real retrenchment in valuations and some will live up to valuations a lot. Well, and like if I look at the public markets, they're very tight right now. It's like the anti-bubble. I look at private valuations. It's like a real bubble. I think there's a reckoning somewhere down the road. And a lot of companies are going to have to do layoffs a lot. It's never fun. It's usually the worst thing in the history of your life. And the temptation is to do, well, just do a little one now and we'll grow into it. And then they do another one in six months and then another one. I think with everything, including this type of thing, it's just rip the darn bandaid off, tell everyone the bad news. They're adults. They can handle it and get it done. And I think people avoid that. I think that's good advice Ruth Porat's giving. Because you're going to have bad news to deliver. Bad shit's going to happen to your company, even though it looks like it's going amazing right now. You're going to, weird stuff's going to happen and you're going to have to deal with it. And we had a lot of weird stuff happen at HubSpot and and there's a basketball coach named Mike Shischewski. He's Duke's basketball coach, all-time winningest college basketball coach ever. If you go to a Duke basketball game, you can hear him yelling from the sidelines, let's play, let's play. And what's going on there is when a college basketball player is playing in the game and takes a shot and clanks it off the rim and misses it, they have a strong tendency to go play overly aggressively on defense in the backcourt and many times compound their error by making a foul or something like that. And what he wants to do is people to make their error, forget about it and move back down the other side of the court and run the play. And so we used, we actually, there were times in HubSpot's history where we had the Mike Shischewski's face on a huge slide in front of the company meeting saying next play because there was an unforced error and we need to deal with it and kind of move on. Is there a story of that that comes to mind that is interesting and worth getting into? There's a lot of them, but I remember in 2000, it was the end, it was the last day of March in 2019 and we had a really bad outage like all day and we never really had one of those. And it was bad, customers were unhappy, a lot of customers canceled. I had a lot of customers yelling at me and I remember that company meeting, I cried in front of the whole company. It couldn't believe it happened to us. And I remember using the next, the next play slide on that one. Yeah. Most of the, we made a lot of mistakes at HubSpot. A lot of bad things happened to companies and most of them were self-inflicted and a lot of them are the old, the old saw like companies are far more likely to die of, of, of over-eating than into digestion. Usually it was, we were trying to do too much. I haven't heard that version. I've always heard most companies that have suicide versus homicide, uh, indigestion. That's true too. Oh man. Um, okay. So, uh, next halogenism, uh, never waste a good crisis. There's something that people hear. I'm curious, just, just kind of like, what's the, what's the lesson here? And then is there an example of this with that, uh, that where you learn this lesson? I'll just follow on to most of the good things that happened in HubSpot came out of a crisis because we would take, you know, pretty drastic measures to fix it and make sure we didn't do the same thing again. And so in this particular case, we really rethought how we deployed software, how we thought about making software in a way that was incredibly healthy. And I mean, we, we haven't had a serious outage since, um, the quality is much better. And it kind of, kind of an interesting thing with HubSpot is we started as a marketing software company and we pivoted, we had Salesforce kind of came into our market. We put it into CRM. And one thing that we, if, if your marketing software goes down, like if your workflow, that there's a bug in the workflows or something like that, it's bad, but you survive it. You wait a little bit. If your CRM goes down, particularly the last day of the quarter, you're really impacting your customer's ability to do business. So that was like a mindset shift that we hadn't quite come to terms with of how important we were to our customers. And so we made a lot of changes based on that crisis. You know, good things come out of crisis. Usually very good things came out of crises. So there's a lesson there. Something's going wrong. Is it just like overcorrect? Like use this as a way to get things? Yes, we always overcorrected. Yeah, swung the, we almost, we purposely swung the pendulum hard the other way. Hmm. Which connects to the first, uh, halogenism of, uh, if you're eating a shit sandwich, no nibble, just, it's almost like go all the way, go even further. Yes. Make it really obvious to everyone what's going on. Hmm. Okay. Another halogenism. If you want to kill a plant, have two people water it. I love this one. It's very true. Let's say, Lenny, you bought a new beautiful plant for your office. And then you went away for a month to Turks and Caicos because you're AI agents doing your podcasts and you asked two of your friends, Hey, can you, would you mind watering my plant? And there's one of two outcomes. What happens to the plant? The plant would either be overwatered and die or not watered at all and die. And every CEO in the adults table has gone through this and they are religious about the DRI. Like everyone talks about DRI in the, in the kids table, but once it gets to the adults table, like people get deep religion on it. And, and I think it makes sense. Like when you're small and you're in startup mode, everyone's in the room, everyone knows exactly what's going on. So let's say you're running a pilot project with a big account. You're running that pilot project. Everyone's on the same page, a salesperson and service person, developer, everyone's on the same page and you go out and do it. Yes. Qtobel. When you get it scale, you get a sales organization, you get your forward deployed engineer organization, you've got product management organization, you've got some developers working on it. Everyone's kind of separate. No one knows really what's going on in the other departments. And so let's say you want to really have a good pilot process. You want to rethink it because you're scaling. Everything important happens cross-functionally inside a company at scale and you need someone powerful to own it. So let's say it's a salesperson. They need the power to like tell people in other divisions what to do, even if they don't own it. So almost every CEO I deal with is like a zealot on the DRI idea. And it doesn't bite you until you get to some sort of scale. And to be super clear about that advice here, it's one person is responsible for a goal of the metric, some outcome you want versus you may feel like, okay, we have two people on this. It'll be awesome to work together. Your advice here is that doesn't work. Committees never were. Yes. Yes. And DRI is directly responsible individual. Hmm. The way I always thought about this is just having someone's ass on the line for something makes them so motivated to get it done versus like spreading, you know, the responsibility and the up and the upside and the downside. It just doesn't work. I totally agree with you. Awesome. Okay. Another algorithm. I don't know if you put it this way. The way I think about it is this idea of there's no such thing as a silver bullet. There just, it just takes a lot of lead bullets to get something done. I think the way you wrote about it is it's always like one step forward, two steps back. Talk about your advice there. Yeah. I always thought incorrectly that we would have one hire or one investor or one event or one product release that would, I was wrong about this, but it'd be a silver bullet. And like the reality inside the HubSpot machine, the way it felt to me, it looks from the outside like over a long time up into the right and smooth, but inside it was two steps forward, one step back, two steps forward, one step back, two steps forward, one step back. Um, and a lot of times it was a crisis that caused that step back. Um, so we just didn't have that. I, in the thing about being a founder CEO is there's no one, especially when you're in your twenties, there's no one there to rescue you. Your parents aren't going to rescue you. Your VC is not going to rescue you. Your teacher, your thesis advisor, you're kind of on your own and you got to figure it out. And that kind of hits you when you hit your first crisis. Like it's on you. You can get some help, but it's on you. Sometimes they have, uh, you in their corner. If they're lucky at Sequoia. I can't solve it. Oftentimes I can be the shoulder they cry on and I can give them advice, but it's still on them. Do you feel like too many people start companies just like, like when someone comes to you, like, Hey Brian, should I start, should I start a company? I have this idea. Do you often just like, no, you don't have no idea what you're getting into. This is going to be much more painful. I heard Jensen Wong say that. Like I wouldn't start NVIDIA if I had to do over. I, that, if someone asked me that question, I would start HubSpot over. It was very hard. Um, there were a lot of sacrifices. It wasn't glamorous at all. But in the end of the day, I'm incredibly proud of it. And you know, I've, you know, on my death bed, I'm gonna look back and be, and really enjoy it. And the Dalai Lama has got a good expression, like live a good life so you can live it again on your death bed. And I'm really glad I did it. But I do talk a lot of fat, a lot of that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that that some opportunity they don't want to waste the opportunity so I think that mindset's right but people today are much more much more hardcore than they were in my era like I worked hard and I was probably I was 60 to 70 week hours a week the entire time never really turned it off but that's kind of how I thought about it it's different now people are much more focused and I think Elon's inspired people like I had a starter back in the day and nowhere near as successful as HubSpot but the way I thought about it is let me just give it everything I have and see what I can do this isn't a shot this is my chance let me just give it all like forget balance just go for it seven days a week for a while you know and then you scale back and it's just like such an empowering thing to do for a while just like let me just try I'll give him a bit this won't be forever yeah and I know you've written about this just like balance for CO is not you should not have work-life balance if you want to be incredibly successful I don't know if that's always true but just what's I don't know how do you talk about that to founders I don't know any of the founders I work with that have work-life balance by the way this is not something I recommend um I didn't have it I don't think my co-founder Dharmesh had it none of the see the only CI CEO I know and he's he's unusual in this way is Kareem from clay he's like nope you need balance take the weekends like he's got a different mindset I'm gonna have him on my pod to to talk about his mindset but he's sort of the outlier everyone else is really really obsessed and they really don't have much of a life it did take them a long time to find product market fit it did definitely free AI I wonder if there's a correlation but it did work out so great so it is it is a good lesson okay a few more here one is uh it's a math formula EV is greater than TV is greater than MEV what is that okay EV is enterprise value TV is your team's value MEV is your value and as HubSpot was scaling and we had a lot of people who were VPs in different roles and they started to get good size organizations where they would fall down was they didn't solve for MEV but they'd solve for TV over EV it's all for their own team so let's say they ran sales let's say I just want bookings to be as high as possible because I get paid on bookings and the service team can handle all the downstream problems I created uh marketing to sales between every department this happened in the kind of immature managers who didn't scale really saw for themselves and some as they saw for themselves kind of sub optimized for their peers and their employees would notice it and complain about it um it would be fine in the short term but it would show up and the place it would show up Lenny was we did and I think a lot of companies do this now but we did a quarterly employee net promoter we did a quarterly customer net promoter survey and a quarterly employee one and we would we would have people rate it by the department they're in and one interesting thing about that so it's like sales and service and engineering all the different departments and we had an overall net promoter score and then each department had a net promoter score and let's just take sales sales net promoter score was like 65 62 68 30. oh that's a big drop and then you read the comments and it was not good a lot of complaints about the leader of that and a lot of the complaints were a little bit of this tv thing um and then we give feedback to that vp would help them we give them all the comments be like you got this and then a quarter later and from 30 to negative 5. it almost they almost never they never actually recovered you lose your team you kind of can't it's hard to get them back um and that's why i say you know hire slow fire fast and this doesn't show up in the first 100 150 employees everyone's solving for ev but as it gets bigger and the ceo doesn't know anyone and there's a couple layers between you and the employees they tend to solve for tv so we always put on the wall solve for ev over tv over me and then we added cv in front of ev solve for the customers first then for spot than the employee than yourself um that was very helpful to us yeah uh i imagine everybody listening working at a big company understands this where you have goals you get your kpis and your performance reviews based on what impact you drive you have if you hit your goals and so you know everyone's the incentives are focused on my goals and drive those and i don't care about other people's goals the company's out goals steve steve jobs had an interesting line he says you don't work for your boss you work for apple i thought that was pretty good and that's i i heard that after i was ceo of hubspot but that kind of captures the sentiment and that's how i felt about hubspot you work for hubspot first and then you work for your boss this is hard because you know people's performance reviews are based on their goals kpis it's always like here's what i got to drive uh other than putting posters on the wall and this is our just hubspot growth above all is what matters our customers i guess in your case is there anything tactically that was useful in helping people purchase enterprise value this was explicitly called out in the form for the employee you know when you got your review this was part of it and so they get they get a score of one to i forget 10 on that i would talk about it constantly and when we first started hubspot i ran it a little bit like jensen runs nvidia where i didn't do one-on-ones and i gave a lot of good and bad feedback publicly in large management team meetings and i definitely would go out of my way to criticize people if i felt like they were solving for tv over ev and people got a sense for that um and then every quarter we did like a really well produced company meeting we spent a lot of time on it at the end of the company meeting we we gave out we called them the champagner awards was a bottle of vuv that my co-founder and i signed and we'd read something nice about them and give it to them and usually there was an ev team in that and so we did different things to kind of beat that into people's heads amazing so here is just celebrate people that focus on this and also include it in their valuation performance reviews yeah okay that's a good segue to another halogenism where you talk about how companies are either customer-centric employee-centric or investor-centric and it's really important to know which you are and you guys actually shifted there what's what's your insight there okay we were very employee-centric um more than customer-centric in the first several years of hubspot it's so much so that we the company was number one on glass door's best place to work i was the number one ceo in glass door and as i look back at that i'm not sure that's a good thing like wanting to be liked i don't think is a good feature of a ceo and wanting to be the best place to work probably isn't the right way to go like if you look at toby from shopify his scores aren't that good but that company is doing really really well um and so we over indexed on it and part of the reason we over indexed on it is is my co-founder was really strong in this and we had an incredibly powerful head of hr named katie burke and we just worked on it we we spent a lot of time on it and when we'd have a management team meeting and let's say it's four hours long like two of the four hours would be on employee stuff and at some point i was like why are we spending so much time on employee net promoter scores like let's say our employee net promoter score was 60 and our customer net promoter score is like 25 i was like we need to take i would give up 10 points of employee net promoter score to get 10 points of of customer net promoter score and so over some time we shifted the center of gravity to customers um and worried we still of course worried about employees but the center of gravity from hubspot moves very much to customers and we did that in a few ways like every time we had a management team meeting we had our management team meetings once a month not once a week and we would have a customer panel come on in that customer panel i would run the panel and ask very tricky questions to the customers and pull out the bad news from that and then we we still do this we have an we have a uh sorry customer panel at our board meetings our whole board can ask questions and my favorite question is what do you love about hubspot and then and then what do you hate about hubspot and they kind of look at their shoes and they're like come on and it's a great way so so the employees voice is here those company meetings we have the the customers in the company meetings we changed the comp plan so the management team got paid not on revenue but on retention in that promoter score and so we worked very hard and kind of swung the pendulum to customer centric uh but i do think companies have one certain gravity or another there's a really interesting thread throughout this conversation of just what do you want to change how you operate you have to go really far to a whole other and almost over correct to like yeah it's really interesting of just how much work it takes to change culture to change norms and the bigger it is the more obvious you have to make it and out and the other thing about being a ceo any is you got to say the same thing over and over and over and over and over again it just doesn't sink into people's heads you have to just be incredibly repetitive on it before it sinks in same thing with marketing but internally uh that happens the other weird thing about being a ceo any is as it gets bigger like when it's small everyone's giving you shit and like you're all on the same level but as it gets bigger you didn't interview everyone you had thousands of employees you don't know everyone and people put you on a pedestal that you don't deserve and let's say you're in the hallway and you're just kind of shooting the with a bunch of people and you're like ah it'd be cool if we had a product that it doesn't it up somebody inevitably would go home and build that thing it'd be like brian wants this is a big initiative so people really lock in on what you said and it turns out you have to be very repetitive you have to be very careful what you say darmesh was on the podcast your uh illustrious co-founder and he developed the whole system to avoid the sort of thing flash tags or it's like this is just an fyi we had a whole system because we would say something on an email to the management team or a slap and everybody like okay this is what they want let's do it and sometimes it is like this is you need to do this and sometimes it is like we should talk about doing this and sometimes it is this is just kind of an fyi we're thinking about it and because it got big we came up with that rubric uh we needed to tag each email with how do you want me to get this done this week or is this something we should talk about or is this something that's just fyi i'm thinking about that's what i was like like one of them is plea i'm pleading you to do i'm not telling you to do this i'm just pleading that you do what i ask oh man okay i like this all this all connects and by the way you guys were co-founders for 20 years um you shared something before we started recording so darmesh famously did not ever want direct reports he's just like brian i want to start this with you but i'm not i don't want to ever manage anyone and you were talking about how you had to take on engineering which didn't make any sense oh i'm an engineer but i'm i can i can code but it's not good and so when we started the company he's like i was a ceo before i was terrible at i want to do it again you're gonna be the ceo i'm like great and he's like and by the way i'm not gonna have any direct reports i'm like well it's just the two of us so don't worry but it's like no ever never i'm like yeah yeah and then you know we get 10 12 people we're starting to hire engineers and onboard them and making up big decisions and i would go to him and be like well can you manage him he's like don't you remember i told you i don't want to have any direct reports it's like surely you were kidding when you said that he said nope is there dharmesh shah has never had a single direct report at hubspot incredible i don't know it's just like a dream a dream a way to operate uh i love that you made it possible for him and it created all this opportunity for him to tinker and yes yes freedom of really think and be creative yeah i'm excited to get him back on the podcast someday we're gonna link to that episode maybe a last question i'm curious if there's anything else you think we missed as a as a company grows and scales the job of a ceo changes you've written a bit about this of just like how different the job is when you're a starter versus a scale up what are some of the things that most change where your time goes as a ceo as the company grows i clicked on this earlier but that inspiration thing like i have a little rubric where it's like in the startup phase it's 90 perspiration 10 inspiration you get the scale up phase it's 90 inspiration 10 perspiration and over time you're doing every job in a startup and you still need to be very attached to it and you still need to talk to customers you can't give it up but man you have to let go of so much stuff over time in order for the organization to scale and i had a i have trust issues like i only trusted a small number of people that have spot to be a dri to really drive something important it drove people crazy that i didn't have a larger trust surface um every one of the ceos i work with has the same problem and that's a that's a scaling limit that was the limit for me um i wasn't trusting enough brian i feel like i could uh chat with you for hours there's a whole list of halogenisms i'm going to link to that we didn't even touch on but before we get to our very exciting lightning round is there anything else that you think we should chat about anything you want to leave listeners with i well i would say if you're a ceo and you're interested in scaling i think the halogen as opposed to like all the mistakes i made in my 15 years being ceo i tried to summarize in there to help you avoid them and i have a pod you should first listen to lenny's pod because it's amazing but i have a pod just for ceos called long strange trip where i interview i interview ceos about this so lenny's interviewing me about being a ceo i get to interview other people about being i'm kind of a ceo geek these days and the the name of the podcast is a grateful debt reference which we haven't touched on but you're a huge deadhead as they say yes that could be a whole other podcast conversation i think they're sure actually because i wrote a book called marketing lessons from the grateful dead and there's so much the grateful dead were like the ultimate silicon valley startup they started in 1964. do you know where they started lenny um no palo alto their early concerts were at stanford were all over silicon valley they're a silicon valley company they were very first principles in their thinking they created a new category a new way to distribute their music they disintermediated the uh the ticketing companies very innovative steve jobs and jerry garcia are like very similar in my mind real crass people so i think of them as a great silicon valley success story uh you said you had a whole book about this uh what what's the book called just in case people want to do your marketing lessons from the grateful dead dead amazing and i read that you bought jerry garcia's guitar for a large sum at some point yes i did and i consider myself the steward of his guitar um it gets played like dead and co played it and there's a million grateful dead cover bands that let them play it but i i'm taking care of it for for the deadheads what's like one nugget of wisdom or lesson that people can take away from the grateful dead for startups okay people talk about spiky teams the grateful dead team was interesting garcia himself was a bluegrass guy he was a banjo player and then bob weir recently passed was kind of a country crooner like like country music then their their bass player was a avant-garde jazz trombonist phil lesh and their um keyboard player was a guy named ron mckernan pig pen and he was like a harmonica guy and the drummer was like a marching band drummer and so spikiest of spiky teams came together and made a new genre they created a new category of music it wasn't rock and roll wasn't sort of rolling stones it wasn't buddy holly it was like this new thing and then they called it a jam band because they played rock and roll in a bluesy open organic kind of jazzy way and so spiky teams in creating categories underrated incredible are you one of these people that have been to like 100 grateful dead concerts makes sense okay uh this could be a whole podcast but we're gonna we're gonna move along um okay with that we've reached our very exciting lightning round brian are you ready let's do this fire it up i've watched you do the right lightning round so many times i'm psyched i'm flattered uh unsurprising questions uh what are two or three books that you find yourself recommending most other people i haven't read a book in a long time i listen to podcasts i'm on x i talked to a lot of other ceos i can't remember the last time i actually sat down and read a book much respect i had mark endreysson on recently and i don't know if you've heard his whole thing on how what he consumes he talks about he has a very barbell strategy to media it's uh either twitter or books that are 10 years or older and i've heard him say that i'm hearing um yeah i kind of stopped reading i looked at that i i was getting ready for this lenny and i was like i can't remember the last book i read i think this is going to make a lot of people feel better that don't read books early all right this is okay um favorite recent movie or tv show you really enjoyed i love the new ken burns very long very good revolutionary war documentary um he's a craftsperson it's exceptionally well done and what i like about it is america is really like a disruptor startup like so many startup lessons from those they're gutsy talk about two steps forward one step back like they got into the details of how george washington ran the army we were very close to losing that war most of the time and two steps two steps forward ten step back two step forward ten steps back lots of lead bullets a slot in the in like unless we had alliances like we had alliances with the french we were screwed uh so i love that that it's a long one but it's really good how long is this what are we getting probably 10 plus hours 10 plus hours what uh it's a lot uh but uh worth it is what i'm here i'm in boston you know it's revolutionary surrounded by history all right uh favorite product you recently discovered that you really love i love my delphi clone i teach a i teach course uh called scaling entrepreneurial ventures and um i don't do i don't do office hours i have delphi do my officers very happy with that the my favorite feature of delphi and again lennybot.com there's my delphi i know we both have little bots uh the voice feature is the coolest thing right great not good great i can't wait i had video they get rid of it they're gonna bring it back can't wait till i have this video my least favorite my lowest mps product is my sonos system you have sonos i do and i i get you yes painful yeah it's like so good in so many ways and so annoying in so many ways but like we still use it you know there's nothing better you're not a competitor you and i should start us on this competitor no we should not that's a bad i'm not doing this and just to be clear what these bots are just so people understand how cool this is so my industry on every single podcast like this one is going to be sucked into it and every single newsletter and you just talk to it and ask it like how do i find product market fit in it's based on everything i've ever shared here's here's your steps okay what's even better about it is is you because you can go to chat gpt and say what would lenny think about this what it's added is the ability to put a bunch of documents in there that aren't on the internet like i put my lectures in there and there's a new feature where it asks you questions and it kind of interviews you and so it's a it's pretty proprietary it's it's getting better i like it a lot yeah to that point the uh i haven't uh uh promoted this feature of it but it's trained on all my paid content too so even if you're not a paid subscriber you get access to all the things i've ever shared no don't tell let's not tell too many people that because it's one day i'm going to pay wallet in the near future anyway enough about that lightningbot.com do you have a favorite life motto that you find yourself coming back to in work or in life this isn't lightning but four years ago i had a very bad snowmobile accident drove a snowmobile up a cliff the snowmobile smashed into a million pieces at the bottom of the cliff so did i go to the cliff and i laid at the bottom of that cliff for a while i was unconscious for a long time i woke up and i didn't think i had my phone so i sat there for a long time like i'm probably gonna die tonight no one knows where i am it's frigid out it's in vermont and i'm gonna freeze to death and i sitting there for a couple hours i finally was like oh i do have my phone dialed 911 by the way 911 amazing service and so the helicopters came in and took me out took me to the hospital and lots of surgeries and i was kind of out of commission for a year uh and you can't see it but i got metal all over me all in me life short like life short and i i made some decisions at the bottom of that cliff that the one of the decisions i made at the bottom of that cliff was i don't really like being ceo of an 8 000 person company doesn't really suit me like my harmonic motion is off i don't love the day-to-day if i make it out of here alive i'm out and so that's exactly what happened like the first big thing that happened coming out of that was i gave the job to yamini who's still the ceo doing a great job so life's short don't waste it i heard this story but it's just as powerful hearing it again what um why do you think it takes people why does it take a moment like that to help have someone realize this i need to change you know or just like i think people think they're going to live forever and they're not um as somebody who's 58 yeah life's very short and i'm much more intentional about the decisions i make much more intentional about the people i hang out with today than i was before that and i really try to work on things that bring me joy like this pot same i i appreciate it um i read the 20 broken bones in this accent a lot of broken bones a lot of metal i get 33 screws in me one loose one up here lenny same okay uh last question we talked a bit about the red sox you're a part owner of the boston red sox now what's something that would surprise people about how a baseball team is run or just what it's like you know on the inside of a team like the red sox it's not as profitable as people think people think like these rich guys come in and buy these teams but the way the league is set up and the way the economics are set up it's not it's not a profitable endeavor whereas like other leagues are much much more profitable um baseball's also also deeply flawed it doesn't have a salary cap and so you've got the dodgers who i take my hat off to have like a 400 million dollar payroll and the miami marlins are like a hundred million dollar payroll and in other leagues that all kind of balances out pretty well baseball sort of it's it's set up incorrectly i think it'll correct uh in the next couple years but um it's kind of it's a broken model intriguing uh stay in ai sast if you want to make money is what i'm hearing vertical sass uh brian this was incredible uh covered almost everything i was hoping to cover uh two final questions where can folks find a line if they want to reach out where they find the bot where do they how do they work with you if they wanted to or do i have to be a sequoie founder uh and then how can listeners be useful to you i came with two things i would love folks to listen to longstream trip my pod and i would i'd get some comments but not a ton like lenny you have more comments than yours i'm jealous i'd like just feedback on how i'm doing like it's very new and i just started a couple months ago it seemed like it's going pretty well but like it's my family and sequoia people giving me feedback i'd like to see how all of you what you think about it so that would be spectacular all right so hop on your youtube and leave some comments about what they think the real real honest feedback okay uh brian thank you so much for doing this appreciate it appreciate it thank you bye everyone thank you so much for listening if you found this valuable you can subscribe to the show on apple podcast spotify or your favorite podcast app also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at lenny's podcast.com see you in the next 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