Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

Your parents aren't going to rescue you. Your B.C. is not going to rescue you.

“That kind of 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 mushroom over the next 10 years relative to last 10 years. It's just going to be hard to stand out and really celebrate 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 and optionality when you can move this fast and try a lot of things. Let's get 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 on the nights.

It's full contact.

“Do you feel like there are specific profiles or traits to be successful?”

I look for fourth thing. I call it my luck algorithm. May my guest as 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 host 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. Century catches it all.

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That's data.hq.com/lany. 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 the way they describe

you is someone with a perpetual state of constructive dissatisfaction. Do you think this is a core foundational kind of trait of successful co-successful leaders? By the way, I like that description. When she did the one-day and work-worry-nearing story to me, she said that I like it.

I took it as kind of a compliment and I liked it. As I've been most of my time these days coaching very fast-gross CEOs, they all are kind of 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. They don't really take stock of what they've done and feel it.

They're always a little bit dissatisfied where they are and very focused on the end state.

CEOs as being, I don't know, I wouldn't humble wasn't the first word that would come out

of your mouth when you describe kind of my generation, but this generation I feel like is different, and I've been impressed with it. 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 move on to this new chapter. Now you work with a bunch of CEOs, your sequoise in-house co-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 of CEOs that are companies that are about under 100 employees, the adult table is over 100 employees. So let me ask you just, when you look at CEOs that move from the kids table to the adult

table, other than just, you know, they scale and grow, what is it that these CEOs that graduate from kids to adults table do differently? The adults are really focused on, and all they really could talk about is they're exact team. They're direct reports, how do you build their exact team at next level down or 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 and upspot'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 that they kind of are making that transition. And I would just say in general, people are very bad at this and upspot was too.

I change CEOs and everyone dramatically overrates their ability to interview and overrates their gut feeling and underrates a really high quality blind reference. And I interviewed Dave the CEO from MongoDB the other day. And he had an interesting study on average over his 10 year lifespan as a CEO of Mongo. There were two C-levels, two C-levels turned over per year.

That's a lot of it turned over at the top. And I didn't keep track of it like Dave, but I think HubSpot was kind of similar. And all of these startups are kind of similar too. And so people are working on that and struggling with it as one thing in common like with all of 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've over a ability”

to interview someone and really know if there are good fit. I give a couple pieces of advice. Parker Conrad has a good hack that I'd like, before he's got a C-level interview, CFO, she brought tough sword ever. He has some sign in NDA and sends them the last board deck or the board memo or some

important dock. And he schedules a half hour interview with them and he just has a chat about the debt. And if they're just very complimentary and it's so great, you're doing this amazing thing, it's a major right 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 it's always a good thing.

I think the standard interview of walking through your background. I don't think it's all that valuable. And I coach people to do blind references, find someone you know that work with them. DCs 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 a hard

questions about this person. And one of my favorite questions people ask is, would you infuse you absolutely rehired

“this person for that role, which I think is a really good question?”

On a scale of one to ten, 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, or is really good. My other piece of advice and no one listens to me on this is higher slow and fire fast.

People hire fast and fire slow. If I had to guess Lenny with the 18 months after you hires, he level exec, at least 50% of the time they're gone. I wore tallity right on them, it's harder than people think.

odds.

“I think you can, I think the blind references are key, I think doing like real interactive”

working on a project together, I'll tell you one of the things we learned in Hubspawn about this, like we would have a candidate come in, let's say a head of engineering. We would have like eight people in every of them, in our scales 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 in every of them,

and everyone's a three out of four. All's every time we hired the three out of four, like the person with the least amount of weaknesses. And we changed it and we went with the spike here, people, we went with people with weaknesses, we went with people with challenge stuff, and that has worked out quite well,

like our hit rate and Hubspawn's improved. We also have shrunk the pool of people on that interview panel from eight to like four,

like we just hired a head of product, and they were just four of us, they never viewed them.

I think that worked too.

“So I think there's things you could need 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, and when they're really just looking for like, when they ask me for the strengths and weaknesses, I'm like, are they've already decided? When they ask me something hard, like, on a scale of 1 to 10, I'll like 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? Oh, you know, that type of question is pretty good.

So when I'm on the other side of it, I like when those types of questions are well. I tell you the other mistake, everyone makes, I made all of the CEOs we're making now, is you're hiring for that whatever, head of engineering, and you're blown away by the resume, like you're 50 employees and you're hiring this person who's been at Microsoft the last 10 years, and is a fancy title, and is fancy division in 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, in the extent that you get your shit together, is just, you don't, 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, like, a void, the big company hire, like we hired so many people from sales for us in Google Microsoft, like 100% you know, attrition rate on all those folks.

Something that I've seen that a lot of companies is there's like phases up like, okay, now it's like 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 the Namazag group.

The McKinsey one never works. It works. It never works. Like by definition,

they would fail on my spectrum of like, most founders are like me, like they are skeptical like conventional wisdom, they're unhappy with the world works in some way, and so they're kind of far on that spectrum of rethinking conventional wisdom, and almost by definition, some of you go to work for McKinsey is very conservative in the rub. So I think that all this 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 sportsman, a big postroom, that says in the Boston Red Sox, hadn't won when they were World Series in 86 years since they traded the rub. And they finally broke, 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, and a lot of people have heard of that they paid a fair amount of money to pay to a martinian, paid to a martinian as in Kurt Shilling, we're kind of the canonical older Ben Nat, and they're done that bigger company folks. And they mixed really nicely the culture really work. And I think

“that's the key. I think people underrate their homegrown talent, like almost across the board,”

they underrated. And I think you want that mix. You don't want to hire a whole bunch of Ben they're done that. You don't want to hire none of them. I don't imagine this is public, but you're now part owner of the Red Sox, is I'm part owner of the Red Sox. Okay, I have questions for you

along those lines. Okay, that's that's amazing advice. Kind of what I'm taking away here is people

Sally's fancy logos, amazing person, VP this that sells for Samazon Google, whatever, and which

Yeah, if you look at HubSpot, like Hat the Management team are folks who demand there for approximately

150 years, which I like. And same with like you look at Apple, a lot of those people are homegrown.

“And so is there any tips here for doing this? Well, is it just like give people a chance?”

I tend to give people a chance. It's like if you're interviewing someone that's homegrown in their VP for that sea level job versus hiring somewhere from the outside, I hire somewhere from the outside. They're very good in interviewing, from a big company, though, advanced to either shiny, you haven't seen their wards hard to figure out their wards unless you're very good at flying referencing. So you tend to

overrate them and underrate your homegrown. So if it's pretty close, I think you give your homegrown

a shout out of it. What's interesting to me, Lenny, is Brian Chesky's sort of rethought a lot of

this stuff. And he's like everyone's overrote to the homegrown, to the experience talent, management teams, and delegation. And if he's mostly right about that, people haven't really followed that. People are, you know, there are people from the outside quite a bit. That's kind of a standard part of the playbook that all of them are following down. It's a little different. Actually, quite different than what Brian's is bouncing. 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, I'm not going to be as good as them. How, there's no world where I'm this good. Do you feel like

“there are specific profiles or just like traits that you have to be born with to be a successful”

CEO? Or do you think it's all earnable? Anybody can be successful if they really work hard. And so go ahead and meet all these CEOs coming in. And I have a little route like algorithm in my head. And I look for four things. I call it my locked algorithm. L is for lovable. And you know, Steve Jobs, you would say is kind of 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? Did they, 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. When we're 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 kind of what

it tastes to be a founder CEO. The C is something a wouldn't have thought of, but this is a Sequoia thing like chip on the shoulder. Pretty much all of them have a bitten me like 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 vein. And so I kind of look for that. If I were to stick an ass on it, I would say student. Like I look at Winston Weinberg from Harvey or James from Profound or Gabe from Rogos.

Some of these new very fast growing companies. They're students of the game. They're not just learn at all. They're deep, deep students of the game. And they're like LLMs. They're constantly constantly learning. And it's not just learning stuff for 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 kind of my little criteria I use when I'm evaluating C. 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 what successful founders? Oh my god. I wish I had the, 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 Terrence 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 like get a

subscription service for all music in the world. That's just what are you doing? You're going to recognize that. Is it learnable? I know there's some of a lot of the CEO struggling with a

couple of things. Like let's say you're, you're Winston, you're late 20s. You've never managed to

team. You're probably never even in captain of this sports team before. And in order to scale,

“like you have to give people feedback like constantly, you know, it's very unnatural in terms of like”

I'm going to give this VPI hired a bunch of feedback positive and negative. And if you don't get good at that, you really pay the price later. But that's something I think they have to learn. They all have to learn to get a good bullshit detector to constantly being spun. Everyone's trying

develop over time. They have to all get good at the inspiration thing over time. Like you're Winston,

you've never had to inspire anyone in your entire life. You know, you went to school in your

lawyer for a few years and you started this thing. Inspiration wasn't your thing. So there's certain

“things you have to kind of learn on that startup to scale up path in the best ones learned at”

very fast. This is extremely interesting and useful. So lock with an S at the end just to kind of mirror back what you're sharing. So which, and when you're saying you evaluate CEOs, this for like investing as a okay. So when you're helping Sequoia decide should we invest in this company? What you look for is locks. I like the S. I'm going to include it there. So are they lovable or they inspiring? Oh, are they obsessed with this problem they're going after? Do they have a chip on

our shoulder? Are they extremely knowledgeable about the problem they're going out? And it sounds like not just the problem, but just the 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 just 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'm known as at so another little rubric I have. And I don't see a lot of these, but like Brett Taylor's one is a few out there that Aaron Sequoia's portfolio. I call them back to the baseball thing, a five to a player. In baseball when you rank a player, it's can they hit, and they hit would power, can they run, and they catch a ball, can they throw the ball, and they rate them kind of one to ten to each. It's very rare that you

have a five-tool player, like extremely rare. And the thing that's kind of new now are there five-tool CEOs, like Brett Taylor's one, you can code, you have tastes, you have vision, you can sell the product, you can give in some toys, like 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's certainly one of the Steve Jobs. He wasn't

“ready. He wasn't programming. It wasn't Jeff Bezos. You know, I think this is kind of a new breed.”

This is 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 it's hard to fill the gap. You know, this guy's a developer. He's a pretty genius level obsessive, but Kenny can he sell. Can he convince an investor to give him a lot of money and a high valuation? Can he convince brilliant employees to leave open AI and join him? Can he convince some basic skeptical,

fortune 500 enterprise to buy his product, like be able to do that and have tastes 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 kind of code, all of a sudden we're going to be able to build stuff. I think it kind of 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 like

the one thing that most often people that become CEOs founders have to work on is they're like

“a most common threat of like 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 kind of 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 like so many of the CEOs are going through that right now. That's a tricky transition. So many of the CEOs are layering folks like you hire 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. You know, those types of conversations are very tricky

and quite unnatural for homo sapiens to have. If you're, you know, 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 it's super uncomfortable, but they have to kind of 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 kind of 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 like the kid's table is 15 CEOs of companies under 100 employees

with each other. It's kind of a safe space. And I can weigh in, but it's actually much more effective

“when there appears way in. I think misery really does like company on stuff like this. They learn”

from each other. So essentially it's fine peers to talk to and share and be a company. In the reason I break it out is like the problems with the kid's table are very different than the problems of the old table. And they all run, 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. Started your 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? It's absolutely true. In the flip side of that is I mean how many companies is the number of companies formed is going to mushroom over the next 10 years relative to last 10 years. And the last 10 years period compared to the previous 10 years is mushroom. I just think in my life like a mole and when I was a kid and walked into

CVS corn drug store and I wanted my toothbrush. There are four or five there. You pick one and you know in the night in like the 90s or 2000s you got Amazon there are four or five thousand toothbrushes. It's four or five thousand 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 like a huge jump back then when we started up to about 2006. But now it's going to be

even bigger jump. So it's easier to start. Now there's so much noise in in constant competition.

“It's just going to be hard to stand out and really celebrate in scale. So that's why say it's”

never been easier to start. There's never been more competitions, never been harder to scale.

And a big part of this is is distribution essentially breaking through the noise is what I've asked. It is hard to learn that. Like you didn't grow up doing distribution. You don't know. So they're all learning it. In the ones that learn fast. It's like a learning game. The faster you learn you know the better you do. Along these lines I say tweet 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 like where's AI like really working? Let's say inside a HubSpot software development. We're incredibly well. Customer support incredibly well. Legal started to work incredibly well.

But there really aren't apps like in the rest of the org that are really changed things a lot.

And in the go to market science being kind of slow. Really just support like there isn't like a

“canonical marketing or sales. Maybe the BDR is the first one. But I think the old 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 way color world. I also I think a lot about the go to market. I think the go to market is going to get turned on and said like when we started HubSpot if I think of the way the funnel worked. You want to get found in Google. Someone click 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 rips ready. Go down that rabbit hole. And I think it's going to get turned on and said where people are evaluating a product. They start in Gemini or they start in Anthropica. They start in Chatchett BT. And for example, Chatchett BT knows way about sure. It 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 is 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. Know everything about your company and your pricing and packaging. And you can have a high quality conversation with that person. That person that will get stored in your CRM and will get, you know, scored. This is a good quality conversation. And then the sales

rep will follow up. But that sales rep will be an avatar with them on every sales call. You want to wait for the RSE. They'll have their own SC that's all knowing that will follow them through the process. So go to work and 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, like when I really want as a home on safety end is I have like a Delphi clone that I really like. Same. It's actually quite good. Yeah, we have

Yeah. We'll link to it. Yeah. And what I want is like connect that thing to my email into my granola into my plot and it knows everything about me. And then when I go to a meeting, I want to invite, I want to invite that thing to my meetings. So it's sitting there in the Zoom meeting. It's not just taking notes like granola. It's a participant. So if I forgot something I asked

“a question if somebody else forgot, like, I think every knowledge worker will have one of these in”

three, four, five years. But mine was more on the go to market side where I think every website will change and they'll be an all-knowing avatar on that home page. And if it's a considered purchase, I think it gets handed off to a sales trap, that sales trap has a conversation, but when that sales trap is on Zoom, they have their SE avatar that's kind of all-knowing. So I think this stuff all changes a lot in the next three years, but it hasn't really unlocked yet. What are we going

to be doing in this world? These two bots chat and we each other? What's going to be great, lady? You and I are going to be like, six non, four-part chat. Three cakeos relaxing on a mobile location, sending our avatars to all meetings. Go buy me some hotspots, seats, please. I think this is my Cloudbot was so popular. I think this is essentially what they're building is this idea, which is now called moldbot, which might be changing again.

It's just like this personal agent that can go do stuff for you, totally. So you're talking about the future of go-to-market is this world where there's these little bots and agents that are doing things for you both on some websites. When you look at companies today that you work with that are doing well, that are 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”

was different today, it's exactly the same as it's been for a hundred years, except they call their SECs or their system consultants for deployed engineers. The best thing is the same. I thought it would be totally different in AI and work with all these companies. They're hiring like 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 in my career

to come to call PTC, which is like an enterprise sales machine. Enterprise sales hasn't changed that much since the 1990s. Okay, and so for deployed engineer, a 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-in play. You can't just set up some agent that figures everything out, takes a lot of onboarding and integration. Is it actually a different

“thing at all? The first is like sales engineering in the past. I think it's a solution to this consultant”

sales engineer. Okay, technical. They help be implemented. They connect all your systems. They customize it. It's different. I mean, you're training it in a different way. But I think, well, anyway, I think the term is fine. I'm sort of being light on it because boy, it looks similar except that role as a different name to it. Got it. So if anything that advice I'm hearing here is just lean into this, continue to lean into this idea of having your employees help the customer on

onboard, be successful and I agree. All that stuff. I think the thing that will change first is the

top of the funnel around getting bound in set of Google. You got to get found in these. Yeah. Yeah. Yeah. That's going to be really important in the way you build your website is very different for that to optimize for it. And then you're, I think, your home page is totally different. I think you land on an avatar and ever conversation with them versus you're going through all the pages on your side. I think the top of the funnel is about to change a lot.

Is anyone doing this well yet? This idea of this avatar is just kind of a, and if you start to work on it, but does it? We built, we built one. It's working. Okay. Okay. Let me ask one more question about CO stuff and then I want to move on to how organisms. All right. How is just being a CO different than it was? So you've been doing this for 20 years. What's like most different about what it was like to be a CO maybe 10, 20 years ago

versus today? One of my C, as actually Winston from Harvey said this like a year ago and I was like that's bullshit, but I actually think it was right. He's like, you can just do a lot more. I mean, you've got a age of doing stuff. Everyone's more productive. Software developers more productive. Like something that used to take you a year or takes two months now. And so the amount of projects in the amount of stuff you can do is much, much more. I think he's right. I think that's a little

dangerous. Like let's say you've found your beach head market and that beach head market is really good and it's very deep. There's a lot of work to do. I think what's dangerous for companies 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 like you think of Open AI and Chechie Beauty and it's consumer

app is doing incredible. And they're doing lots and lots and lots and lots and lots and lots and lots

and they've kind of focused back on the core. I think there's a lot of competition everything

“is moving fast. I do think people get more done. And I think that impacts everything. Like 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. Like I just think of times in HubSpile when things slowed down and there was turn. 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 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 the doors much more quickly than they used to. I think that's

new and different and different. I was someone who always valued optionality. I think there's a

massive tax and 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's so many reasons this is happening. One is just technology is just like every week there's a new shift in what is possible. Yes. If you're spending all these months thinking and planning, just like what a waste of time it ends up being because so much is changing. I know. Yeah, it's hard to keep up. Luckily we got some sweet podcast to check

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Let's talk halogenisms. Essentially, these are nuggets of wisdom and advice that you find yourself sharing often. You've written a bunch of these about a bunch of these online. And so let me just go through them and then just share a share of the synopsis of the advice in the lesson around

“this halogenism. The first is, when you have to eat a shit sandwich, don't nibble. Okay,”

completely stole this from Ruth Porath, the CEO of Google. I saw her quote somewhere. I'm like, "That's it, she's just 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 and valuations in some, some will live up to your valuations a lot wall. And like if I look at the public markets, they're very tight right now. It's like the anti-bumble.

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 do another one and 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 with reports, giving. As you're going to have bad news to the liver, bad shit's going to happen here, company, even the little thing'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 up to Hubspot. And there's a basketball coach name, Mike Sheshefty. He's Duke's basketball coach all-time winning his college basketball coach ever.

If you go to a Duke basketball game, you can hear me yelling from the sidelines. That's play. That's play. And what's going on there is when a college basketball player is playing 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 back court. And many times compound 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 and Hubspot's history where we had the Mike Sheshefty's face on a huge slide in front of the company meeting saying next play because there was an unports there 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 last day of March in 2019 and we had a really bad out-itch 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 play slide on that one. Yeah. We made a lot of mistakes that Hubspot, a lot of bad things happened to the companies and most of them were self-inspected. And a lot of them are the old saw, like, companies were far more like they did dive of overreacting than in suggestion. Usually, it was we were trying to do too much. I haven't heard that version. I've always heard most companies

that I have suicide versus homicide. I was into justice. I just do too. I'm not afraid of it.

Oh, man. Okay, so next, Haliganism, never wasted good crisis. There's something that people

hear. I'm curious, just kind of like, what's the lesson here? And then there's an example of this with that, where you learn this lesson. I'll just follow on to most of the good things that happened and 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 haven't had a serious outage since the quality is much better. You know, kind of an interesting thing with Hubspot as we started as a marketing software company. And we pivoted. We had Salesforce kind of came into our market. We pivoted in CRM. And one thing that if you're marketing software goes down, like, if you're workflow at this above and 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 come out of crisis. So the lesson there, some things going wrong, is it just like over-correct, like use this as a way to

always over-corrected. Yeah. Swung the, we almost, we purposely swung the pendulum hard the other way.

Which connects to the first haliganism of if you're doing a shit sandwich in a nipple, just it's almost like go all the way, go even further. Yes. Make it really obvious to everyone what's going on.

“Okay. Another haliganism. 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 Cacos because you're a age and steering your podcast. And you ask two of your friends, "Hey, can you, would you mind watering my plant?" And this water of two outcomes would happen to the plant. The plant would either be overwatered and die or not watered all and die. And every CEO in the adult

stable has gone through this and they are religious about the DRI. Like everyone tells it would DRI in the kids table, but once it gets to the adult's table, people get deeper, legit on it. And I think it makes sense. Like when you're small and you're in start of 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 run that pilot project. Everyone's on the same page,

salesperson, and service person, developer, everyone's on the same page. And you go out and do it. Yes, you do well. When you get it's scale, you get a sales organization, you get for a deployed engineer organization, you get product management organization, you get 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 and 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

one person is responsible for a goal of metric. Some outcome you want versus it 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. Communities never work. Yes. Yeah. Yes. It's in DRI directly responsible individual.

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 that 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 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 higher or one investor or one event or one product release that I was wrong about this, but it would be a silver bullet. And like the reality inside the upspot 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. 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 I'm about being a founder CEO is there's no one especially when you're in your 20 is no one there to rescue you. Your parents aren't going to rescue you. Your BC 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 you in their corner. They're like, yeah, that's the go. Yeah. Well, like, I can't stop it off. And then as 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 company on 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 what long to do that. Like, I would start in the end if I had it to do over. That if someone asked me that question, I would start up spot over. It was very hard. 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, my deathbed, I'm going to look back and be in really enjoyed. And the Dalai alum is going to get expression like, 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

“a lot of fenders out of it. Like, the obsession is real. It's, it's, you have to be deeply obsessed.”

And all these, all these founders and CEOs I talked to, I mean, people talk about 996.

It's way more than that. I mean, the founders are seven days a week. They're always on.

I text from them on Sunday nights. It's full contact. And I think what's going on there, particularly now as people just see this massive platform change, massive 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 ear. Like, I worked hard. I was probably, my was 60 to 70 week hours a week, the entire time. Never really turned it off. But that's kind of like

thought about it. It's different now. People are much more focused. And I think Elon's inspired people like, I had to start it back in the day. And nowhere near a successful as helps put. But the way I thought about it is, let me just give it everything I have and see what I can do. This is the shot. This is my chance. Let me just give it all. Forget balance. Just go for it. Seven days a week for a while. You know, 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 it a minute. This won't be forever.

“Yep. And I know you've written about this. Just like balance for CO is not. You should not”

have more like balance if you want to be incredibly successful. And 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

how any of the founders I work with that have work like balance. By the way, this is not something I recommend. I didn't have it. I don't think my co-founder Darmash had it. None of the see it. The only CICL I know. And he's unusual in this way is Korean from clay. He's like, no, you need balance. Take the weekends. Like, he's got a different mindset. I'm going to have them on my pod to talk about his mindset. But he's sort of the outlier everyone else is really, really

obsess and they really don't have much of a life. It did take them a long time to find product market fit. It did bring a lot. It did bring a lot if there's a correlation. But it did work out. So it's a great. So it is a good lesson. Okay. A few more here. One is it's a math formula.

TV is your team's value. Me, V is your value. And as I thought 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. Let's get paid on bookings. And the service team can handle

all of the downstream problems I created, marketing to sales. Between every department this happened in the kind of immature managers who didn't scale really soft for themselves. And as they soft themselves kind of suboptimized 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 down, but we did a quarterly”

employee nepper mode. We did a quarterly customer nepper mode survey and a quarterly employee one. And we would we would have people braided by the department they're in. And one interesting thing about that. So there's like sales, the service, and engineering, all the different departments. And we had an overall nepper mode of score and then each department had a nepper mode of score. And let's just take sales. Sales nepper mode of score was like 65, 62, 68, 30, oh, that's a big drop.

And then you read the comments and it was not good. And 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 can 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 five. And almost they almost never, they never actually recorded.

“I mean, lose your team. You kind of can't. It's hard to get them back. And that's why I say,”

you know, higher slow fire fast. And this doesn't show up in the first 150 employees, everyone's solving for EV, but as it gets bigger. And the CO does a no-one in 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 maybe. And then we added CV in front of EV, solve for the customers first, then perhaps, but then the employee, then yourself. That was very helpful to us.

Yeah. I imagine everybody listening working in 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 have your goals. And so, you know, everyone's the incentives are focus on my goals and drive those. And I don't care about other people's goals, the companies about goals. These team jobs had an interesting line. Because you don't work for your boss, you work for Apple.

I thought that was pretty good. And that's, I heard that after, I would say, I'm as fat,

“but that kind of captures the sentiment. And that's how I felt about Hubsby. You work for Hubsby 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. Other than putting

posters on the wall, and this is our just Hubsby growth above all is what matters. Our customers, I guess, and you're okay. Is there anything tactically that was useful in helping people prioritize enterprise value? This was explicitly called out in the form for the employee group. You know, when you get 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 Hubsby,

I ran it a little bit like Jensen runs in video where I didn't do one of ones, and I gave a lot of good and bad feedback publicly in large management meetings. And I definitely would go out of my way. It's a criticized people. I felt like they were solving for TV over ED, and people got a sense for that. And then every quarter we did like a really well-produced company meeting. We spent a lot of time on it. And at the end of the company meeting, we gave out,

we called it in the Champaignor Awards. It was a bottle of booze 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 ED 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 in their valuation performance reviews. Yeah. Okay. This is 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 the company was number one

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's doing really, really well. And so we over-indexed on it. And part of the reason we over-nate in next on it

is my co-founder is really strong in this. And we had an incredibly powerful and a major in

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, like two of the four hours would be I'm placed up.

“And at some point, I was like, why are we spending so much time on employee-net promoters scores?”

Like, let's say our employee-net promoter score was 60. And our customer-net, a net promoter score was like 25. I was like, we mean to say, 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. And we still, of course, we're worried about employees, but the center of gravity from HUD Fund was very much customers. And we did that in a few ways. Like, every time we had

a management team meeting, we had a management team use once a month, not once a week. And we would

have a customer panel come on. And 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 or a 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 kind of look at their shoes and they're like, come on. And it's the great way. So the employees' voices

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 in that promoter score. And so we weren't very hard and kind of swung the pendulum to customer centric. But I do think companies have one sort 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 over-correct to like, yeah, it's a really interesting. I've just come much work it takes to change culture to change arms. And the bigger it is, the more obvious you have to make it. And the other thing about being in the CEO and he is, you got to see the same thing old for an 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 and he 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 know, 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 just kind of shoot and shit with a bunch of people and you're like, yeah, be cool if we

had a product that it does or does it up. Somebody inevitably would go home and build that thing. It'd be like Brian wants this as a big initiative. So people really lock in on what you said.

“And it turns out you have to be very repetitive and you have to be very careful what you say.”

Dimash was on the podcast, your illustrious co-founder and he developed a whole system to avoid the sort of thing flash tags or it's like, it's just an FYI. We had a whole system because we would say something on an email to the management team or it's flat and it would be like, okay, this is what they want. Let's do it. And sometimes it is like, this is what you need to do this. And sometimes it is like, we should talk about doing this. 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. 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? And what it is like, like, one of them is plea, pleating you to do. I'm not telling you to do this. I'm just pleating that you do what I ask. Oh man, okay. There's all this all connects. And by the way, you guys are co-founders

for 20 years. You shared something before we started recording. So Dimash famously did not ever want direct reports. He's just like, right, I want to start this video, but I don't want to ever ban in January. And you're talking about how you had to take on engineering, which didn't make any sense. Oh, I'm an engineer, but I'm, and I can code, but it's not good. And so when we started the company, he's like, and I was a CEO before it was terrible at everyone doing it again. You need me to see

it on the 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 about it. It's like, no, ever. Never. I'm like, yay. And then you

get 10 to 12 people who are starting to hire engineers and onboard them and making out big decisions.

you when Emily direct reports is like, "Surefully, you were kidding when you said that." He said,

"Nope. Is there a Dermesh Shah has never had a single direct report at Upspot?"

Incredible. I don't. It's just like a dream, a way to operate. I love that you made it possible for him. And it created all this opportunity from the Tinker and in the frame of a 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 in 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 started versus a scale-up. What are some of the things that most change where your time goes as a CEO is the company grows? We clicked on this earlier, but that inspiration thing, like I have a little lubric 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 and a startup and you still need to be very attached to it

“and you still need to talk to customers and 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. I have trust issues. I only trust it a small number of people that have spot to be a VRI and really drive something important. It drove people crazy that didn't have a larger trust service. And every one of the CEOs they work with has the same problem. And that's a scaling limit. That was a 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 how I get as I'm going to link to that when 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 with us next week? I would say if you're a CEO and you're interested in scaling, I think that the halligan is supposed to like all the mistakes I made in my 15 years of being CEO.

“I tried to summarize in there. So I hope 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 LongStrangeTrip,

right in review. I hear review CEOs about this. So Lenny's interviewing me about being a CEO. I get to interview other people about these. I'm kind of a CEO geek these days. And the name of the podcast is a grateful debt reference, which we haven't touched on by your huge debt head. 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 debt and there's so much

a grateful debt. We're like the ultimate Silicon Valley startup. They started in 1964. 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 the ticketing companies, very innovative. Steve Jobs and Jerry Garcia

“are like very similar in my mind. Real-class 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 marketing lessons from the grateful debt? Amazing. 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-plated. And there's a million grateful debt cover bands that left them flat, but I'm taking care of it for for the deadheads. What's like one nugget of wisdom or lessen that people can take away from the grateful debt for startups? Okay, people talk about spiky teams. The grateful debt team was interested in Garcia himself was a bluegrass guy. He was

a bandro player. And then Bob weir recently passed was kind of a country cruner like like country music. Then their their base player was a avant-garde jazz trombones fell less in their keyboard player was a guy named Ramakura and pickpen and he was like a harmonica guy. And the drummer was like a marching band drummer. And so spiky us of spiky teams came together and made a new genre that created a new category of music. It wasn't rock and roll. It 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 any of these people that have been to like a hundred

Okay, with that we reached our very exciting lightning ground. Brian, are you ready? Ooh, that's too this. Fire it up of what you do right? Like around so many times. I'm flattered on surprising questions. 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 thought to a lot of other CEOs. I can't remember last time I actually sat down and read a book.

Much respect. I had Mark Dendrison 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 either Twitter or books that are 10 years or older. I've heard him say that. I'm her. Yeah, I kind of stopped reading. I looked at that. I was getting ready for this landing and I was like, I can't remember

“where 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. 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 crass person. It's exceptionally well done. And when I like about it, it is America's really like a disruptor startup, like so many startup lessons from those group. There are 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 forward. Ten steps back. Two steps back. Two steps back. Two steps back. Two steps back.

Lots of lead bullets. A lot in like, unless we had alliances like we had alliances with the French, we were screwed. 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 with a lot, but worth it is what I mean.”

I'm in Boston, you know, it's a revolutionary round of my history. All right. Favorite product,

you recently discovered that you really love. I love my Delphi clone. I teach a, I teach a course called Scaling Entrepreneurial Ventures. And I don't, I don't do avasaurus. I have Delphi doom around avasaurus. Very happy with that. The my favorite feature of Delphi and again, Lennybot.com is my Delphi. I know that we both have a little bot. The voice features, the cool thing. Right. Great. I can't, I had video. They get rid of it. They're going to bring it back.

Can't wait till I ask video. My lead's favorite. My lowest empty as product is my sonos system. You have sonos? I do. And 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. Not a

“competitor. You and I should start a sonos competitor. No, we should not. That's a bad. I'm not doing”

this. And just to be clear with these bots are just so people understand how cool this is. So my industry, not every single podcast like this one is going to be sucked into it and every single news that are and you just talk to it and ask it like how do I find product market fit in space 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 you between say what would Lenny think about this? What it's

added is the ability to put a bunch of documents in there that are on the internet. Like I put my live lectures in there. And there's a new feature where it asks you questions and it kind of interviews you. And so it's pretty proprietary. It's getting better. I like it a lot. Yeah, to that point, the I have an pop 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 of the things I've ever shared.

That's not tell. Let's not tell too many people that because it's one day I'm going to pay all it in your future. Anyway, enough about that. Let me buy.com. Do you have a favorite life motto that you find yourself coming back to in worker and life? This isn't lightning, but four years ago, I had a very bad snowmobile accident drove a snowmobile out of cliff. That snowmobile

smashed into a million pieces at the bottom of the cliff. So did I. And I laid at the bottom of that

cliff for a while. I was trying to catch a falling time. It 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 gonna freeze to death. And I sit in 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 I took me out, took an hospital and lots of

surgeries. And I was kind of out of commission for a year. And you can't see up, I got metal all over me, all in me. Life short, like, life short. And I made some decisions at the bottom of that cliff.

person company. Doesn't really suit me. Like, my harmonic motion is off. I don't love the day today. 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 Yomini, who's still the CEO, doing a great job. So life short, don't waste it. I heard the 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 a change, you know, or just like, I think”

people think they're going to live forever. And they're not. Um, as some of the 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 appreciate it. 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,

let me. 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 like these rich guys come in and buy these teams. But the way the lead is set up and the way the economics are set up is not it's not a profitable endeavor where it's 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,

I like a 400 million dollar payroll and then Miami Marlins, I like a hundred million dollar

payroll. And it's another lease that all kind of balances out pretty well. Baseball sort of it's set up incorrectly. I think it'll correct in the next couple of years. But it's kind of

“it's a broken mall intriguing. Stay in AI SaaS. If you want to make money is what I'm hearing.”

Vertical SaaS. Brian, this was incredible. Uh, covered almost everything I was hoping to cover. Two final questions, where can folks find a line if they want to reach out where they find the bot where they how do they work with you if they want it to or they have to be so quite founder. Uh, and then how can listeners be so to you? I came as two things. I would love folks to listen to a long-strain trip, my pod. And I would get some comments, but not a ton, like any more

comments in yours and just, I'd like to just feedback on how I'm doing, like it's very new. And I just started a couple of months ago. It seemed like it's gone pretty well. But like, it's my family and so quite a people giving me feedback on, I'd like to see how all of you what you think about it. So that would be spectacular. All right. So how do you even leave some comments about what they think? The real, real honest face, the real

earned. Okay, here comes Brian, thank you so much for doing this. Appreciate, appreciate you. 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 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 episode.

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