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

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 kind

of hits you when you hit your first crisis.

>> Starting a company has never been easier. Scaling one into a durable, high

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 the last 10 years. It's just

going to be hard to stand out and really accelerate. What's most different about

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 and 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 cos. I don't

founders. They want to be cos. I don't

think anyone can do it. People talk

about 996. It's way more than that.

Founders are 7 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

successful? I look for four things. I

call it my lock algorithm.

Today my guest is Brian Hallagan, 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.

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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 described you is uh someone with a perpetual state of constructive dissatisfaction.

Do you think this is a core foundational kind of uh trait of successful co successful leaders?

>> By the way, I like that description. I

when she did a woman named Lori Norington who's sub chair said that I like it. I took it as kind of a

like it. I took it as kind of a compliment. Um, and I and I liked it.

compliment. Um, and I and I liked it.

And as I so I spend most of my time these days coaching very fast growth CEOs. They all are kind of like that. Um, they're they're all in

kind of a state of perfeual 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 they've done and and feel it.

They're always a little bit dissatisfied with where they are and very focused on the end state. And I've been surprised at how humble this generation is of

CEOs. And I think of my generation of

CEOs. And I think of my generation of 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 is different.

Um and I've been impressed with it.

>> Okay. I have a bunch of questions along these lines. Um because one you've been

these lines. Um 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

chapter. Now you work with a bunch of CEOs. You're the you're Sequo's in-house

CEOs. You're the you're Sequo's in-house coach. There's a few things that I've

coach. There's a few things that I've heard you do. One is you gather groups of cos and uh what I've read is that you have kind of two tables. You have the

kids table and the adults table. The

kids table of cos that are companies that are about under 100 employees. The

adults table is over 100 employees. Uh

so let me ask you just when you look at cos that move from the kids table to the adult table other than just you know they scale and grow. What is it that these cos that graduate from kids to

adults table uh do differently?

>> The adults are are really focused on and all they really want to talk about is their exec team, their direct reports. How do you build our exec team?

reports. How do you build our exec team?

That next level down org design. You

would be surprised how much they think about that. And on average, I would say

about that. And on average, I would say the adults are spending half their time just recruiting and interviewing. It's pretty all-consuming

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. Um 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 HubSpot

was too.

I think 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 uh Dave, the CEO from MongoDB the other day and he had an interesting stat. On average over his

interesting stat. On average over his like 10year lifespan as a CEO of there were two sea level two sea 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'm 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 uh as one thing in common like 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 over ability to interview someone uh and really know if they're a good fit. Um,

I give a couple pieces of advice. Parker

Conrad has a good hack that I like. Uh,

before he's got a sea level interview, 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 halfhour 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 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.

Um, getting on a whiteboard and working through a problem, I think, is always a good thing. I think the standard

good thing. I think the standard interview of walking through your background, I don't think is all that valuable. Um, and I coach people to do

valuable. Um, and I coach people to do blind references. Find someone you know

blind references. Find someone you know that work 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

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

that role?" which I think is a really good question. On a scale of 1 to 10,

good question. On a scale of 1 to 10, how likely is it that you'll try to rehire this person back from me down the road? I think those types of questions

road? I think those types of questions are good. So, not mailing in on those

are good. So, not mailing in on those blind references, I think, are is really good. My other piece of advice, and no one listens to me on

this, is is hire slow and fire fast. Um

people hire fast and fire slow. Uh, and

if I had to guess, Lenny, within 18 months after you hire a seale exec, at least 50% of the time they're gone. There's this there's high

gone. There's this there's high mortality rate on them. It's it's harder than people think.

>> And what so what you're saying here is there's only so much you can actually do to increase those odds.

>> I think you can I I I think you can you can um I think the blind references are key. I think doing like real interactive

key. I think doing like real interactive working on a project together. I'll tell

you one other thing we learned at HubSpot about this like we would have a candidate come in let's say a head of engineering and we'd have like eight people interview them and our scale is one 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, like the person with the least amount of weaknesses and we changed it and we we went with the spikier people. We went with people with weaknesses. We went with people

with weaknesses. We went with people with challenge stuff. And that has worked out quite well. Like our hit rate at HubSpots improved. We also have shrunk the the pool of people on that

interview panel from eight to like four.

Like we just hired a a head of product and there were just four of us that interviewed them. I think that worked

interviewed them. I think that worked too. Um, so I think there's things you

too. Um, 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, uh, the

useful. On the references piece, uh, 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

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 if they've already decided. Mhm.

decided. Mhm.

>> When they're really just looking for like when they ask me for the strengths and weaknesses, I'm like or they've already decided. When they ask me

already decided. When they ask me something hard like on a scale of 1 to 10, how likely are you to hire them again? Stuff like that that kind of gets

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.

your employees? That's a good question.

Oh, were they top 10? Oh, you know, that type of question is pretty good. Uh, so

when I'm on the other side of it, I like when I like when those types of questions come up. I tell you the other mistake everyone makes I made and all

the CEOs are 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 has a fancy title and 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 in the in the extent that you've got your together.

It's just you don't you definitely don't uh if you're 50 or 500 employees and they expect you to have your act together and so that is another like avoid the big company hire like we hired

so many people from Salesforce and Google Microsoft like 100% you know attrition rate on all those folks. Something that I've seen at

those folks. Something that I've seen at a lot of companies is there's like phases of like, okay, now it's like the McKenzie a cohort comes in and we think that's going to be the answer and then it's the Apple group and then that

didn't work out. Then the Amazon group, >> the Mackenzie one never works. It never

works.

It never works. Like by definition, they would fail on my spectrum of like most founders are like me. Like they are skeptical of conventional wisdom.

They're unhappy with the world works in some way. And so they're kind of far on

some way. And so they're kind of far on that spectrum of of rethinking conventional wisdom. And almost by

conventional wisdom. And almost by definition, somebody who goes to work for McKenzie is very conservative in their outlook. Um, and so I think that

their outlook. Um, and so I think that almost always fails.

>> We're on this hiring kind of thread, so let me keep following this conversation.

Uh, I read somewhere that you recommend building your team like the 2004 Red Sox.

What does this mean? I'm a Well, I'm a big sports fan. a big Boston Red Sox and the Boston Red Sox hadn't won Lenny a World Series in 86 years since they traded

>> 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 that a lot of people have heard of that they paid a fair amount of money to Pedro Martine Pedro Martinez as and Kurt Schilling

were kind of the canonical older been that 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

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 been there done that. You

don't want to hire none of them.

>> I don't I imagine this is public but you're now a part owner of the Red Sox.

Is that >> I am the part owner of the Red Sox. Yes.

>> Okay. I have questions for you along those lines. Okay.

those lines. Okay.

>> Okay. That's uh that's amazing advice.

Uh kind of what I'm taking away here is people see all these fancy logos, amazing person, VP this, that at Salesforce Amazon Google whatever.

And what you're saying here is uh don't underestimate the power of someone internal uh rising to the occasion.

>> Yeah. If you look at HubSpot, like half the management teams are folks that have been 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

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 seale job versus hiring someone from the outside. You hire someone from the

outside. You hire someone from the outside. They're very good at

outside. They're very good at interviewing from a big company. They

look fancy. They're shiny. You haven't

seen their warts. Hard to figure out their warts unless you're very good at plan referencing. And so you tend to

plan referencing. And so you tend to overrate them and underrate your homegrown. So, if it's pretty close, I

homegrown. So, if it's pretty close, I think you'd give your homegrown shot at it. What's interesting to me, Lenny, is,

it. What's interesting to me, Lenny, is, you know, Brian Chesy sort of rethought a lot of this stuff. And he's like, everyone's over over rotating to the home grow to the um, you know,

experienced talent and management teams and delegation. And I think he's mostly

and delegation. And I think he's mostly right about that. People haven't really followed that. People are, you know,

followed that. People are, you know, they're 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

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

CEOs. A lot of people listening to this podcast, there's a lot of people in the world want to be founders. They want to be CEOs. At the same time, you look at

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

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 learnable? Anybody can be successful

all learnable? Anybody can be successful if they really work hard in school. I

meet all these CEOs coming in and I have a little like algorithm in my head and I look for four things. I call it my lock

algorithm. L is for lovable.

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

this person? Would I crawl across broken glass? That's question one.

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 who'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 kind of 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 be like a boulder on their shoulder. And I

I have a bit of a chip on my shoulder, too. And the K is just for deeply

too. And the K is just for deeply knowledgeable about the domain. And so I kind of look for that. Um, if I were to

stick an S on it, I would say student.

Like I look at Winston Weinberg from um 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 learn it alls. They're deep, deep, deep students

alls. They're deep, deep, deep students of the game. And they're they're like LLMs. They're constantly constantly learning. and it's not just learning

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's kind of my little criteria I

use when I'm evaluating CEOs. What do

you look for, by the way? You've

interviewed 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 uh 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 Terren Rohan. When it's just extremely

Terren Rohan. When it's just extremely ambitious, just trying to do something really wild that most people are like that's crazy. You're not going to 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? Do it and you're going to do

doing? Do it and you're going to do that.

>> And like is it learnable? I know notice some of the a lot of the CEOs struggling with a couple things. Like let's say you're you're Winston, your late 20s, you've never managed a team. you're

probably never even captain of a sports team before.

And in order to scale, like you have to give people feedback like constantly and it's very unnatural. It's like I'm going to give this this VP I hired a bunch of

feedback, positive and negative. And if

you don't get good at that, you pay really pay the price later.

That's something I think they have to learn. They all have to learn to get a

learn. They all have to learn to get a good 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 sort of something they have to develop, you know, over time. They

have to all get good at the inspiration thing over time. Like you're you're Winston. You've never had to inspire

Winston. You've never had to inspire anyone in your entire life. You know,

you're you went to school and you're a lawyer for a few years and you started this thing. Like inspiration wasn't your

this thing. Like inspiration wasn't your thing. So there's certain things you

thing. So there's certain things you have to kind of learn on that startup to scale up path and the best ones learn it very fast.

>> This is extremely interesting and useful. So lock uh with an s at the end

useful. So lock uh with an s at the end just to kind of mirror back what you're sharing. So what you and when you were

sharing. So what you and when you were saying you evaluate cos is 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 uh

locks I like the s I'm going to include it there. So are they lovable? Are they

it there. So are they lovable? Are they

inspiring? Uh, oh, are they obsessed with this problem they're going after?

Uh, do they have a chip on their shoulder? Are they extremely

shoulder? Are they extremely knowledgeable about the problem they're going after? And it sounds like not just

going after? And it sounds like not just the problem, but just the studying company's business strategy, things like that.

>> And then S was a student. I guess that's what S is student is studying this uh 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 are born or do you think they're made? Can anyone turn into an amazing student?

>> I don't think anyone can do it. I don't

think it's just anyone. I I will say I've noticed that so another little rubric I have and I don't see a lot of these but like Brett Taylor's one.

There's a few out there that are in Koa's portfolio. I call them a back to

Koa's portfolio. I call them a back to the baseball thing, a 52 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 they rate them kind of one to 10 at each. And 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 are five tool CEOs like Brett Taylor's one. You can code, you have

Taylor's one. You can code, you have taste, you have vision, you can sell the product, you can convince employees 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 certainly wasn't Steve Jobs.

those. That certainly wasn't Steve Jobs.

He wasn't writing pro, he wasn't programming. Um, it wasn't Jeff Bezos.

programming. Um, it wasn't Jeff Bezos.

Uh, you know, I think there's kind of a new breed that's quite impressive.

>> These folks you mentioned, uh, were this good before AI became a thing. I imagine

AI helps more cos fill the gaps that they have.

>> I think it's it's hard to fill the gap of, you know, 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? Um, can he convince some big skeptical Fortune 500

enterprise to buy his product? Like

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 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 cos most have to learn. Uh BS detection, uh inspiring people, giving heart feedback.

What's maybe like the one thing that most often people that become cos founders have to work on? Is there like a most common thread 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

machine. Like so many of the CEOs are going through that right now. Uh that's

a tricky transition. So many of the CEOs are layering folks like 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 profile. Can't quite unpack the sales process. Can't quite forecast

sales process. Can't quite forecast accurately. We need to layer the person.

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. 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

give them? Is it something that they study to improve? I

>> I think misery loves company on this. of

what I do. Like the kids table is 15 CEOs of companies under 100 employees and the adults table are CEOs of companies over 100 employees about 15 of

them. They talk about this with each

them. They talk about this with each other. It's kind of a safe space and I

other. It's kind of 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

in. I think misery really does like company on stuff like this. They learn

from each other.

So essentially it's find peers to talk to and share and be component of >> and the reason I break it out is like the problems at the kids table are very different than the problems at the adult table. Um and and they all they all rhy

table. Um and and they all they all rhy 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 uh 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? It's

a company? It's >> absolutely true.

>> And the flip side of that is I mean, how many companies is the the the number of companies formed is going to mushroom over the next 10 years relative to the last 10 years. And the

the last 10 years compared to the previous 10 years is mushroom. I just

think in my life like I'm old and when I was a kid I'd walked into CVS corn drugstore and I want to buy a tooth toothbrush

there four or five there you pick one and you know in the n in like the 90s or 2000s you go to Amazon there are four or 5,000 toothbrushes four or 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 like a huge jump back

company. So, it's like a huge jump back then when we started up about 2006, but now it's going to be an even bigger jump. So, it's easier to start now.

jump. So, it's easier to start now.

There's so much noise in in con in uh 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

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

more competition. It's never been harder to scale.

>> And a big part of this is is distribution essentially. Breaking

distribution essentially. Breaking through the noise is what I'm hearing.

>> And it's hard to learn that like you didn't grow up doing distribution. You

don't know. So they they're all learning it. Um and the ones that learn fast,

it. Um and 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 saw you tweet this recently where uh people talk about which jobs AI is going to replace and you uh said that sales is maybe the last

job AI will replace. What 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 of HubSpot, software development is working incredibly well.

Uh customer support incredibly well.

Um legal starting to work incredibly well, but there really aren't apps like in the rest of the org that have really changed things a lot. And in the go to market side's been kind of slow uh

really just support like there isn't like a canonical marketing or sales or maybe the BDR is the first one but I think ye 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 white collar world. I also I think a lot

about the go to market.

I think the go to market's going to get turned on and said like when I 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 Anthropic or they start in chat BT and you know for example chat knows way about It knows everything on your website,

everything beyond that knows all your competitors. So they they will stay in

competitors. So they 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 that will get stored

person. that person that will get stored in your CRM and and will get um you know scored this is good quality conversation and then the sales rep will follow up but that sales rep will being an avatar

with them on every sales call you won'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 understand so this is uh 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 I I I I think both. I think me as a knowledge worker, >> like what I really want as a homo sapien is I have like a deli clone that I really like.

>> Same.

>> It's actually quite good.

>> Yeah. Where where do people find yours?

>> Uh they find it on my footer. They can

find it on >> del. We'll link to it.

>> del. We'll link to it.

>> Yeah. And what I want is like connect that that thing to my email into my granola into my plaude and it knows everything about me. And then when I go

to a meeting, Lenny, I want to invite I want to invite that thing to my meeting.

So it's sitting there in the Zoom meeting. It's not just taking notes like

meeting. It's not just taking notes like granola. It's a participant. So if I

granola. It's a participant. So if I forgot something, I asked it 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 there'll be a 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 that's kind of all knowing. 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

world? These two bots chatting with each other.

>> It's going to be great, Lenny. You and I are gonna be like sitting on a >> podcasting kickos relaxing on a monthlong vacation sending our avatars to all the meetings.

>> Go buy me some Hub Hubspot seats, please. I think this is why Cloudbot was

please. I think this is why Cloudbot was so popular. I think this is essentially

so popular. I think this is essentially what they're building is this idea which is now called Moldbot, which might be changing again. Uh it's just like this

changing again. Uh it's just like this personal little 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 on both sides. When you look at companies today

sides. When you look at companies today that you work with that are doing well that are especially AIdriven 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 100 years except they call their sees or their system consultants for deployed engineers. the rest of it is

deployed engineers. the rest of it is the same. I thought it would be totally

the same. I thought it would be totally different in AI. I'm working with all these companies. They're hiring like all

these companies. They're hiring like all the same folks and 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 like an enterprise sales machine. Enterprise

sales hasn't changed that much since the 1990s.

>> Okay. And so, for a deployed engineer, very hot term. Uh the idea there is they come work with the the c the customer and help them implement this thing. And

that that's come up a lot on this podcast just with AI tools. Rarely are

they just plug-and-play. You can't you can't just like set up some agent that figures everything out. Takes a lot of onboarding and integration. Is it

actually a different thing at all other versus like sales engineering in the past things like that?

>> It's a solutions consultant sales engineer. They're technical. They help

engineer. They're technical. They help

you implement it. 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 I'm

sort of 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 uh continue to lean into this idea of having your employees help the customer on board, be successful, integrate, all

that stuff. I think the thing that will

that stuff. I think the thing that will change first is the top of the funnel around getting found in instead of Google, you got to get found in in in these >> Yeah. AEO.

>> Yeah. AEO.

>> Yeah, that's going to be really important. And the way you build your

important. And the way you build your website is very different for that to optimize for it. Um and then your I think your homepage is totally different. I think you land on an avatar

different. I think you land on an avatar and have a conversation with them versus you're going through all the pages on your site. I I think the top of the

your site. I 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 kind of a in the future?

>> If you start a program, HubSpot does it.

We built we built one. It's working.

>> Okay. Okay. Um let me ask one more question around CO stuff and then I want to move on to haganisms. >> All right.

>> Um >> how is just being a CEO different than it was? So you've been doing this for

it was? So you've been doing this for 20ish years.

>> Yeah.

>> Um what's like most different about what it was like to be a CEO maybe 10 20 years ago versus today? One of my CEO, I was actually Winston from um Harvey said

this like a year ago and I was like that's But I actually think he was right. He's like you can just do a

was right. He's like you can just do a lot more. I mean you've got AI agents

lot more. I mean you've got AI agents doing stuff. Everyone's more productive.

doing stuff. Everyone's more productive.

The software developers are more productive. Like something that used to

productive. Like 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

more. I think he's right. I think that's a little dangerous. Like let's say you 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

do. I think what's dangerous for companies is they hop to that second act too quickly. Uh and they lose focus on

too quickly. Uh and they lose focus on that first act. And this isn't a completely perfect analogy but like you think of OpenAI and CHPT and it's a consumer app is doing incredible and they're doing lots and lots and lots and

lots of other things and then Gemini comes out and they've kind of focused back on the core. Uh I think there's a lot of competition. Everything's moving

fast. I 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

year. I think the planning cycles now are 3 months long.

Yeah, that's a big change. I think it puts pressure on the CEOs to be faster and better decision makers. Um

decision makers. Um like I just think of times in HubSpot when things slowed down and there was churn. It was usually my fault. It was

churn. It was usually my fault. It was

because there were some hard, you know, one-way door type decisions on my desk.

And, you know, maybe every year I would sit down and I' I'd open that oneway 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

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's so many reasons this is happening. One is just technology is

is happening. One is just technology is just like every week there's a new shift in what is possible.

>> So, if you're spending all these months thinking and planning just like what a waste of time it ends up being cuz 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

happening. We'll link to yours, of course. Here's a puzzle for you. What do

course. Here's a puzzle for you. What do

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let's talk hagganisms. 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. Um, and so let me just go through them and then just share share kind of the synopsis of the advice and the lesson around this halaganism.

The first is when you have to eat a sandwich, don't nibble. Okay, 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

somewhere. I'm like, that's it. She's

put put a perfect thing on it. And I'll

give you an example where I think this will play out over the next couple years. I think within the next couple

years. I think within the next couple years there'll be a real retrenchment in valuations and some some will live up to valuations a lot won't 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 do another and then they do another one in six months and then another one. I think with everything

another one. I think with everything including this type of thing is just rip the darn band-aid off. Tell everyone the bad news. They're adults. They can

bad news. They're adults. They can

handle it and get it done. Um and I think people avoid that. I I think that's good advice Ruth Ruth Porat's giving because you're going to have bad news to deliver. Bad shit's going to happen to your company. Even if it looks

like it's going amazing right now, you're gonna weird stuff's going to happen and you're gonna have to deal with it. And and we had a lot of weird stuff happen at Hub

HubSpot and and there there's a basketball coach named uh Mike Shashesky.

He's Duke's basketball coach, all-time winningest college basketball coach ever. If you go to a Duke basketball

ever. If you go to a Duke basketball game, you can hear him yelling from the si 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 back court and many times compound their error by making a foul or something like that. And what he wants to do is people

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 Shasheesky'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 uh interesting and worth getting into? There's a lot of them, but

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 um it was bad. Customers were unhappy. A

lot of customers canled. I had a lot of customers yelling at me. And I remember that company meeting. I cried in front of the whole company. He couldn't

believe it happened to us. And I

remember using the next the next play um slide on that one. Um yeah,

>> most of we made a lot of mistakes at HubSpot. A lot of bad things happen to

HubSpot. A lot of bad things happen to companies and most of them are self-inflicted >> and a lot of them are the old the old saw like companies are far more likely to die of

of of overeating than indigestion.

Usually it was trying to do too much. I

haven't heard that version. I've always

heard most companies die of suicide versus homicide.

Indigest too.

>> Oh man. Um, okay. So, uh, next hagganism. Uh, never waste a good

hagganism. Uh, never waste a good crisis. This something that people hear.

crisis. This 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 that where you learned those lessons? I'll

just follow on to most of the good things that happened at housewife 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

thing again. And so in this particular case, we really rethought how we deployed software, how we thought about making software in in a way that was incredibly healthy.

And I mean, we we haven't had a serious outage since. Um the quality is much

outage since. Um the quality is much better. And kind of an interesting thing

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 came

into our market we pivoted into CRM and one thing that we if if your marketing software goes down like if your workflow 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 customers 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

that crisis. You know, good things come out of you. Usually very good things came out of crisis.

>> So there's a lesson there. Something's

going wrong. Is it just like overcorrect? Like use this as a way to

overcorrect? Like use this as a way to >> we always overcorrected. Yeah. Swung the

we almost we purposely swung the pendulum hard the other way. M which

connects to the first uh halaganism of uh if you're eating a sandwich, don't nibble. Just it's almost like go

don't nibble. 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 hagganism. 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 Caos because your AI agents doing your podcast and you asked two of your

friends, hey, can you would you mind watering my plant and there's one of two outcomes would happen to the plant. The

plant would either be over watered 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 DRRI. Like everyone talks about DRRi 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

big account. You're running that pilot project, everyone's on the same page, a salesperson, a service person, developer, everyone's on the same page, and you go out and do it. You execute

well. When you get it scale, you get a sales organization, you've got your forward deploy and engineer organization, you've got your product management organization, you 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

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 crossf functionally inside a company at scale and you need someone powerful uh to own it. Uh, so let's say it's a salesperson.

it. Uh, 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 is like a zealot on the

DRRi idea. And it doesn't bite you until

DRRi idea. And it doesn't bite you until you get to some sort of scale. And to be super clear about the advice here, it's one person is responsible for a goal, a metric, some outcome you want versus uh

it may feel like, okay, we have two people on this, it'll be awesome, they'll work together. Your advice here is that doesn't work. Committees never

work. Yes. Yes. It's in DRRI is directly responsible individual.

>> The way I always uh thought about this is just having someone's ass on the line for something uh 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. Uh another algism, 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

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.

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 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 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. Um, and a lot of

times it was a crisis that caused that step back. Um, so we just didn't have

step back. Um, so we just didn't have that. I And the thing about being a

that. I And the thing about being a founder CEO is there's no one, especially when you're in your 20s, 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 you in their corner if they're lucky at Sequoa. Plug

>> I can't oftenimes. 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 of this idea?" Do you often just like

idea?" Do you often just like >> No, you don't have no idea what you're getting into. This is going to be much

getting into. This is going to be much more painful. I heard Jensen Hong say

more painful. I heard Jensen Hong say that like I wouldn't start Nvidia if I had it 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.

hard. Um there were a lot of sacrifices.

It wasn't glamorous at all and but in the end of the day I'm incredibly proud of it and you know you know on my death bed I'm going to look back and be and really enjoy it. And the

Daly Lama's got a good 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 f lot lot of founders 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 talk 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. Um,

it's full contact. And I think what's going on there, particularly now, is 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 era. Like, I worked hard. I was probably

era. Like, I worked hard. I was probably I was 60 to 70 week hours a week for the entire time. Never really turned it off,

entire time. Never really turned it off, but that's kind of how I thought about it. It's different now. People are much

it. It's different now. People are much more focused. And I think Elon's

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 is nichot. This is

my chance. Let me just give it all like forget balance. Just go for it seven

forget balance. Just go for it seven days a week for a while. You know, then you scale back. Um and it's just like such an empowering thing to do for a while. Just like let me just try. I'll

while. Just like let me just try. I'll

give it my 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 uh 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 Dash had it. None of the C the only CI C 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 going to have him

different mindset. I'm going to 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.

We're definitely pre AI.

>> Wonder if there's a correlation, but it did work out. So,

>> great.

>> So, it is a it is a good lesson. Okay.

Uh a few more here. One is uh it's a math formula. EV is greater than TV is

math formula. EV is greater than TV is greater than me. What is that?

>> Okay. EV is enterprise value. TV is your team's value. Me is your value. And as

team's value. Me 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 goodsiz organizations where they would fall down was they didn't solve for me but they'd solve for

TV over EV. It's all for their own team.

So let's say they ran sales. and 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 and the kind of immature managers who didn't scale really saw for themselves and sub as they saw for themselves kind of

suboptimized for their peers and the 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

departments. And we had an overall net promoter score. And then each department

promoter score. And then each department had a net promoter score. And let's just take sales. Sales net promoter score was

take sales. Sales net promoter score was like 65, 62, 68, 30. Ooh, that's a big drop. And then you read the comments and

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

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 from 30 to neg

five. It almost they almost never they

five. It almost they almost never they never actually recovered. When 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 higher slow fire fast. And this

doesn't show up in the first 100 150 employees. Everyone's solving for EV,

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 MV, and then we added CV in front of EV. Solve for the customers first,

of EV. Solve for the customers first, then for HubSpot, then the employee, then yourself. Um, that was very helpful

then 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 if you hit 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 company's 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

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

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 or customers I guess in your case. Is there

anything tactically that was useful in helping people prioritize 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

it. And so they get they get a score of one to I forget 10 on that. I would talk about it constantly and I 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

prodduced company meeting. We spent a lot of time on it and at the end of the company meeting we we gave out we called them the champagne awards was a bottle of VUV that my co-founder and I signed and would 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 hagganism 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. 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

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. Um,

and so we overindexed 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 name, Katie Burke, and we just worked on it. We we spent a lot of time on it. And when we have a management

on it. And when we 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

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 moved very much to customers. And we did that in a few ways

customers. And we did that in a few ways like every time we had a management team meeting. We had our management team

meeting. We had our management team meets 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 we still do this

we have an employ we have a uh sorry 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 and then what do

you hate about HubSpot and they kind of look at your shoes and you're like come on and it's a great way so so the employees voices here those company meetings, we had the the the customers

in the company meetings. We changed the comp plan. So the management team got

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 kind of swung the pendulum to customer centric. Uh but I do think

companies have one center of gravity or another.

>> There's a really interesting thread throughout this conversation of just when do you want to change how you operate? you have to go really far to a

operate? you have to go really far to a whole other and almost overcorrect 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 and the other thing about being a CEO Lenny 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 and like you're all on the same level, but as it gets bigger, you didn't interview everyone. You thousands of

interview everyone. You 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

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 d somebody inevitably would go home and build that thing and

be like, Brian wants this. This is a big initiative. So people really lock in on

initiative. So people really lock in on what you say. And it turns out you have to be very repetitive and you have to be very careful what you say.

>> Dares was on the podcast, your uh illustrious co-founder and he developed a whole system to avoid this sort of thing. Flash tags or it's like this is

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 Slack and everyone be like okay this is what they want. Let's do it. And sometimes it

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 of 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 >> it 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 This all this all connects. And by the way, you guys were

connects. And by the way, you guys were co-founders for 20 years. Um you shared something before we started recording.

So Dash famously did not ever want direct reports. He's just like, "Brian,

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.

>> Well, 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, "I was a CEO before. I was terrible at it. I want

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,

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

reports." I'm like, "Well, it's just the two of us, so don't worry about it."

He's like, "No, ever. Never." I'm like, "Yeah, yeah, yeah." And then, you know, we got 10 12 people and we're starting to hire engineers and on board them and making our big decisions. And

I would go to him and be like, "Well, can you manage them?" He's like, "Don't you remember I told you I won't have any direct reports?" He's like, "Surely you

direct reports?" He's like, "Surely you were kidding when you said that." He

said, "Nope." So, Der Sha has never had a single direct report at HubSpot.

>> Incredible. I don't 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. And

>> it's a free month to really think and be creative.

>> Yeah. I'm excited to get him back on the podcast someday. We're going to link to

podcast someday. We're going to link to that episode. Maybe a last question. And

that episode. Maybe a last question. And

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 scaleup. What

are some of the things that most change where your time goes as a CEO as the company grows? We clicked on this

company grows? We 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 at HubSpot to be a DRRi to really drive something important that drove people crazy that I didn't have a 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 a limit for me. Um, I wasn't trusting enough.

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 haggis 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 halaganism post is like all the mistakes I made in my 15 years being CEO. I tried to summarize in there. to

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

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 the Grateful Dead reference, which we haven't touched on, but you're a huge >> dead head as they say.

>> That could be a whole other podcast conversation. I think there should

conversation. I think there should 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

startup. They started in 1964. Do you

know where they started, Lenny?

>> Um, no. PaloAlto.

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 craft 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?

this. Uh what what's the book called?

Just in case people want to dig in.

>> 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 I consider myself the steward of his guitar.

>> Um it gets played like Dead and Co played it. And there's a million

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 Dead Heads.

>> 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 kuner like like country music. Then

their their bass player was a avancgar jazz trombonist, Phil Leash. And their

um keyboard player was a guy named Ram Mccernan Pigpen. And he was like a

Mccernan Pigpen. And he was like a harmonica guy. And the drummer was like

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

new genre. They created a new category of music. It wasn't rock and roll.

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 cuz 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

underrated. Incredible. Are you one of these people that have been to like a 100 Grateful Dead concerts? Okay.

>> Makes sense. Okay. Uh, this could be a whole podcast, but we're going to we're going to move along. Um, okay. With that, we've

move along. Um, okay. With that, we've reached our very exciting lightning round. Brian, are you ready?

round. Brian, are you ready?

>> Let's do this.

>> Fired up. I've watched you do the right lightning round so many times.

>> I'm flattered. Unsurprising questions.

Uh, 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 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 Andrew 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

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 nothing.

>> I've heard him say that. I'm heard him say that. Uh, yeah. I kind of stopped

say that. Uh, yeah. I kind of stopped reading. I looked at I I was getting

reading. I looked at 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. I like, all right, this is okay.

books. I like, 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 crafts person. It's

exceptionally well done. And what I like about it is America is really like a disruptor startup. Like so many startup

disruptor startup. Like so many startup lessons from those ear they were gutsy.

Talk about two steps forward, one step back. Like they got into the details of

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, 10 steps back. Two steps

forward, 10 steps back.

>> Lots of lead bullets. a lot and like and like unless we had alliances like we had alliances with the French, we were screwed. Uh so I love that that it's a

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 into?

>> Probably 10 plus hours.

>> 10 plus hours. What a It's a lot. Uh but

uh worth it is what I'm hearing.

>> 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 deli clone. I teach a I teach a course uh called scaling entrepreneurial ventures and um I don't do I don't do office

hours. I have deli do my office hours.

hours. I have deli do my office hours.

Very happy with that.

>> The my favorite feature of deli and again lennybot.com there's my deli though we both have little bots. Uh the

voice feature is the coolest thing right just good great I can't I had video they got rid of it they're going to bring it back. Can't wait till it has video. My

back. Can't wait till it has 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. So

annoying.

>> But like we still use it, you know?

There's nothing better.

>> You're not a competitor. You and I should start as someone competitor.

>> No, we should not. That's a bad I'm not doing this. And just to be clear what

doing this. And just to be clear what these bots are just so people understand how cool this is. So my strain 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 here's your steps.

ever shared. Here's here's your steps.

Okay. What's even better about it is is you because you can go to chatbtd 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 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 of the things I've ever shared. No, don't not tell let's

ever shared. No, don't not 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. landingbot.com.

that. landingbot.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 off a cliff. The

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 unconscious for a long time. 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

I am. It's frigid out. It's in Vermont and I'm going to 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,

phone." Dialed 911. By the way, 911, amazing service. And so, the helicopters

amazing service. And so, the helicopters came in, 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

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. The the one of the decisions I

cliff. The 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.

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

I'm out. And so that's exactly what happened. Like the first big thing that

happened. Like the first big thing that happened coming out of that was I gave the job to Yam who's still the CEO doing a great job. So life's short. Don't

waste it. I've 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 is 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 somebody who's 58,

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

before that. And I really try to work on things that bring me joy, >> like this pot.

>> Same. I I appreciate it.

>> Same. Um I read that you had 20 broken bones in this accident.

>> Lot of broken bones. A lot of metal.

>> I got 33 screws in me. One loose one up here. Lenny.

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 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

more profitable. Um, baseball's also also deeply flawed. It doesn't have a salary cap. And so you've got the

salary cap. And so you've got the Dodgers, who I take my hat off to, have like a $400 million payroll, and the Miami Marlins are like a $100 million payroll. And in other leagues, that all

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

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 SAS if you want to make money is what I'm hearing.

Vertical SAS. Uh, Brian, this was incredible. Uh, covered almost

incredible. Uh, covered almost everything I was hoping to cover. Uh,

two final questions. Where can folks find you online if they want to reach out? Where do they find the bot? Where

out? Where do they find the bot? Where

do they how do they work with you if they wanted to or do they have to be a Squway founder? Uh, and then how can

Squway founder? Uh, and then how can listeners be useful to you?

>> I think there's two things. I would love folks to listen to long strange trip my pod and I would I 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 it 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

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 faith.

think. The real real honest faith.

>> Okay, here it comes. Uh Brian, thank you so much for doing this.

>> Appreciate you. Appreciate you. Thank

you. Bye everyone. Thank you so much for listening. If you found this valuable,

listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider

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

lennispodcast.com.

lennispodcast.com.

See you in the next episode.