# Scaling Strategy: CEO Traits, Hiring, and AI GTM

**Podcast:** Lenny's Podcast: Product | Growth | Career
**Published:** 2026-02-15

## Transcript

The thing about being a founder, CEO is there's no one there to rescue you.
Your parents aren't gonna rescue you, your VC is not gonna 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 gonna be hard to stand out and really accelerate what's most different about what it was like to be a CEO maybe 10, 20 years ago versus today.
There's a massive tax 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 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.
Bike Tech Sunday nights.
It's full contact.
Do you feel like there are specific profiles or traits to be successful?
I look for four things.
I call it my lock algorithm.
Today my guest is Brian Halligan, co-founder and longtime CEO of HubSpot.
I asked Brian to come on this podcast because he is more than anyone I've met, a student of the job of a CEO.
After leaving HubSpot last year, he became the in-house CEO coach at Sequoia, where he brings together dozens of top CEOs to learn from each other.
He does one-on-one coaching with some of the world's top CEOs.
He also hosts a popular podcast called Long Strange Trip, where he interviews some of the world's most successful CEOs.
In this conversation, we unpack what it takes to be a successful CEO in today's era.
Let's get into it after a short word from our wonderful sponsors.
Applications break in all kinds of ways: crashes, slowdowns, regressions, and the stuff that you only see once real users show up.
Sentry catches it all.
See what happened, where, and why.
Down to the commit that introduced the air, the developer who shipped it, and the exact line of code, all in one connected view.
I've definitely tried the five tabs and slack thread approach to debugging.
This is better.
Sentry shows you how the request moved, what ran, what slowed down, and what users saw.
Sear, Sentry's AI debugging agent takes it from there.
It uses all of that Sentry context to tell you the root cause, suggest a fix, and even opens a PR for you.
It also reviews your PRs and flags any breaking changes with fixes ready to go.
Try Sentry and Sear for free at Sentry.io slash Lenny and use code Lenny for $100 in Sentry Credits.
That's SCNTRY.io slash Lenny.
This episode is brought to you by Datadog, now home to EPO, the leading experimentation and feature flagging platform.
Product managers at the world's best companies use Datadog, the same platform their engineers rely on every day to connect product insights to product issues like bugs, UX friction, and business impact.
It starts with product analytics, where PMs can watch replays, review funnels, dive into retention, and explore their growth metrics.
Where other tools stop, Datadog goes even further.
It helps you actually diagnose the impact of funnel drop-offs and bugs and UX friction.
Once you know where to focus, experiments prove what works.
I saw this firsthand when I was at Airbnb, where our experimentation platform was critical for analyzing what worked and where things went wrong.
And the same team that built the experimentation at Airbnb built Epo.
Data Doc then lets you go beyond the numbers with session replay.
Watch exactly how users interact with heat maps and scroll maps to truly understand their behavior.
And all of this is powered by feature flags that are tied to real-time data so that you can roll out safely, target precisely, and learn continuously.
Datadog is more than engineering metrics.
It's where great product teams learn faster, fix smarter, and ship with confidence.
Request a demo at Datadog HQ.com/slash Lenny.
That's datadog HQ.com slash Lenny.
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're someone with a perpetual state of constructive dissatisfaction.
Do you think this is a core foundational kind of uh trait of successful CEOs, successful leaders?
By the way, I like that description.
I uh when she did the woman named Laurie Nearing Norrington, who's some chair said that I like it.
I took it as kind of a 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 perfection, 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 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 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.
Um, and I've been impressed with it.
Okay.
I have a bunch of questions along 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 move on to this new chapter.
Now you work with a bunch of CEOs.
You're the your Sequoia's in-house CEO coach.
There's a few things that I've heard you do.
One is you gather groups of CEOs.
And 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 are CEOs that are companies that are about under 100 employees, the adult table is over 100 employees.
Uh so let me ask you just when you look at CEOs that move from the kids table to the adults table, other than just, you know, they scale and grow.
What is it that these CEOs 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 that next level down, org design?
You would be surprised how much they think about that.
And on average, I would say the adults are spending half their time just recruiting and interviewing.
It's pretty all consuming.
And I remember that from that phase in HubSpot's growth.
And it surprises people, like, wow, my job is really just to interview and hire.
I didn't know that was going to be the case.
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 SAT on average over his like 10-year lifespan as a CEO of Mongo, there were two C level, two C levels turned over per year.
That's a lot of turnover at the top.
And I didn't keep track of it like Dave, but I'm thinking 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, is 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 gonna work out?
What advice do you give them to help them develop that skill?
I think even me, I've been doing this for 150 years.
I still think I overrate my ability to interview someone 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 C level interview with CFO, chief product officer, whatever.
He has him sign an NDA and sends them the last board deck or the board memo or some important doc.
And he schedules a half hour interview with them.
And he just has a chat about the deck, and if they're just very complimentary and it's so great, and 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 interview of walking through your background, I don't think is all that valuable.
Um, and I coach people to do 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 questions people ask is, would you enthusiastically rehire this person for that role?
Which I think is a really good question.
On a scale of one to 10, how likely is it that you'll try to rehire this person back from me down the road?
I think those types of questions are good.
So not mailing it in on those blind references, I think are really good.
My other piece of advice, and no one listens to me on this, is uh is hire slow and fire fast.
Um, people hire fast and fire slow.
Uh and if I had to guess, Lenny, with 18 months after you hire a C-level exec, at least 50% of the time they're gone.
There's this I 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 think you can you can um I think the blind references are key.
I think doing like real interactive working on a project together is key.
I'll tell you one of the things we learned at HubSpot about this.
Like we would have a candidate come in, let's say a uh head of engineering, and we'd have like eight people interview them in our scales one to 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 want people to challenge stuff.
And that has worked out quite well.
Like our hit rate and HubSpot'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 there were just four of us that interviewed them.
I think that worked 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 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 if they've already decided.
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 something hard, like on a scale of one to 10, how likely you are to hire them again, stuff like that, that kind of gets at the core.
Or were they the top one percent of 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 all 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 your 50 employees and you're hiring this person who's been at Microsoft the last 10 years and is 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 shit 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 a lot of companies is there's like phases of like, okay, now it's like the McKinsey, 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 McKinsey 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 what world works in some way.
And so they're kind of far on that spectrum of rethinking conventional wisdom.
And almost by definition, somebody who goes work for McKinsey is very conservative in 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?
And the well, I'm a big sports fan, a big post for med so in the Boston Red Sox hadn't won Lenny a World Series in 86 years since they traded Andrew.
And they finally broke and they finally won it in 2004.
And the way they won it was they had a team of a bunch of homegrown, really high quality, inexpensive talent that they drafted and came through the farm system.
And then they got a few free agents like David Ortiz that a lot of people have heard of that they paid a fair amount of money to.
Pedro Martini and Pedro Martinez and Kurt Schilling were kind of the canonical older Ben that done that bigger company folks.
And they mixed really nicely.
The culture really worked.
And I think that's the key.
I think people underrate their homegrown talent, like almost across the board, they underrate it.
And I think you want that mix.
You don't want to hire a whole bunch of men that have done that.
You don't want to hire none of them.
I don't I imagine this is public, but you're now part owner of the Red Sox.
Is that I am a part owner of the Red Sox, yes.
Okay.
I have questions for you along 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 team 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 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 and they're VP for that C level job versus hiring someone from the outside.
Yeah, hire someone from the outside.
They're very good at interviewing from a big company, they look fancy, they're shiny.
You haven't seen their awards, hard to figure out their awards unless you're very good at blind referencing.
So you tend to overrate them and underrate your homegrown.
So if it's pretty close, I think you give your homegrown a shot at it.
Uh what's interesting to me, Lenny, is you know, Brian Chesky sort of rethought a lot of this stuff.
And he's like everyone's over over rotating to the home grown, to the um, you know, experienced talent and management teams and delegation.
I mean, I think he's mostly right about that.
People haven't really 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 it's a little different.
It's actually quite different than what Brian's espousing.
Going back to the conversation around CEOs, a lot of people listening to this podcast, just a lot of people in the world want to be founders.
They want to be CEOs.
At the same time, you look at Elon, you look at Jensen, you look at Steve Jobs, you look at you.
A lot of people are like, I can't, I'm not this person.
I'm not, I'm not gonna 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 if they really work hard.
And Skoa meet all these CEOs coming in, and I have a little root like algorithm in my head.
And I look for four things.
I call it my lock algorithm.
L is for lovable.
And 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 class?
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 have 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 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 knowledgeable about the Dane.
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 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 of the game.
And they're they're like LLMs that are 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'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 Lenybot.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 uh Terence Rohan.
One is just extremely ambitious, just trying to do something really wild that most people are like, that's a crazy.
You're not gonna like get a subscription service for all music in the world.
That's just what do you want to do it?
You're gonna go.
And like, is it learnable?
I know notice some of the a lot of the CEOs struggling with a couple of 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.
Like, I'm gonna 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 good bullshit detector.
So 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 anyone in your entire life.
You know, you're a you went to school and you're a lawyer for a few years and you started this thing like inspiration wasn't your 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, just to kind of mirror back what you're sharing.
So which and when you're saying you evaluate CEOs, 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'll uh I like the S.
I won't get included 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 knowledgeable about the problem they're 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 uh a student.
I guess that's what S is student is studying this uh the 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 CEO?
I don't think anyone can do it.
I don't think it's just anyone.
I I will say I 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 Aaron Sequoia's portfolio.
I call them a back to the baseball thing, a five-tool player.
In baseball, when you rank a player, it's can they hit?
Can they hit with power?
Can they run?
Can they catch a ball?
Can they throw the ball?
And they they rate them kind of one to ten 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 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.
He wasn't writing pro he wasn't 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 CEOs fill the gaps that they have.
I think yeah, 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 and a high valuation?
Can he convince brilliant employees to leave open AI 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 gonna 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.
Uh BS detection, uh, 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 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 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 process, can't quite forecast accurately.
We need to layer the person.
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 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 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 company on stuff like this.
They learn from each other.
So essentially it's fine peers to talk to and share and be incredible.
And the reason I break it out is like the problems with the kids' table are very different than the problems of the adult table.
Um and they all 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 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 so easy.
Absolutely true.
And the flip side of that is I mean, how many companies is the the number of companies formed is going to mushroom over the next 10 years relative to the last 10 years.
And the last 10 years pretty compared to the previous 10 years is much room.
I just think in my life, like I'm old, and when I was a kid, I'd walked into CVS corn drug store, and I want to buy a toothbrush 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 greater than its 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 an even bigger jump.
So it's easier to start.
Now there's so much noise and in constant in uh competition, it's just gonna be hard to stand out and really accelerate and scale.
So that's why I say it's never been easier to start.
There's never been more competition, it's never been harder to scale.
And a big part of this is is distribution, essentially breaking through the noise, is what I'm gonna saying.
It's hard to learn that.
Like you didn't grow up doing distribution.
You don't know.
So they're all learning 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 gonna replace.
And you uh said that uh 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 a HubSpot, software development's 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 has 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 think a lot about the go to market.
I think the go to market's gonna get turned on its head.
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 ChatGPT.
And you know, for example, ChatGPT knows way about your, he knows everything on your website, everything beyond that, knows all your competitors.
So they will stay in there and do lots more research and be incredibly well educated.
So your website's a lot less important.
And they go to your site.
I think sites will change where you're going to have a really high quality avatar that knows everything about your products, knows everything about your company and your pricing and packaging.
And you can have a high quality conversation with that person.
That person that will get stored in your CRM in and will get um, 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 won't have to wait for their SE.
They'll have their own SC 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 gonna change a lot.
Does 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 think both.
I think me as a knowledge worker, like what I really want as a homeless safety in is I have like a Delphi clone that I really like.
Same.
It's actually quite good.
Yeah, uh, you have.com.
Yeah, where's where do people find yours?
Uh they find it on my footer, they can find it on Delphi.
Yeah, we'll link to it.
Yeah.
And what I want is like connect that 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, Lenny, I want to invite, I want to invite that thing to my meeting.
So it's sitting there in the Zoom meeting, not just taking notes like granola.
It's a participant.
So if I forgot something, I 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 home page.
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.
And so I think this stuff all changes a lot in the next few years, but it hasn't really unlocked yet.
What are we gonna be doing in this world?
These two bots chatting with each other.
Which gonna be great, Lenny.
You and I are gonna be like sitting on the person cakeos relaxing on a month-long vacation, sending our avatars to all the meetings.
Go buy me some hubs, hubspot seats, please.
I think this is why CloudBot was so popular.
I think this is essentially what they're building, is this idea, which is now called Moltbot, which might be changing again.
Uh, it's just like this person, a 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 both sides.
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's different today, it's exactly the same as it's been for a hundred years, except they call their SCEs or their system consultants for deployed engineers.
The rest of it is the same.
I thought it would be totally different in AI.
I'm working with all these companies.
They're hiring 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, uh, very hot term.
Uh, the idea there is they come work with the the custom 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.
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.
I think it's a solutions consultant sales 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.
Uh uh, 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 onboard and be successful integrate all that stuff.
I think the thing that will change first is the top of the funnel around getting found instead of Google, you got to get found in these Yeah, AEO.
Yeah, that's gonna be really important.
And the way you build your website is very different for that to optimize for it.
Um then your I think your homepage is totally different.
I think you land on an avatar and have a conversation with them versus you're going through all the pages on your side.
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 case?
Hubspot does it.
We built we built one, it's working.
Okay.
Okay.
Um, let me ask one more question around CEO stuff, and then I want to move on to halogenisms.
All right.
How is just being a CEO different than it was?
So you've been doing this for 20-ish 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 C, you know, as actually Winston from um Harvey said this like a year ago, and I was like, that's bullshit.
But I actually think he was right.
He's like, you can just do a lot more.
I mean, you've got AI agents doing stuff, everyone's more productive, the software developers are more 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 a little dangerous.
Like, let's say you found your beachhead market, and that beachhead market is really good and it's very deep, and there's a lot of work to do.
I think what's dangerous for companies is they hop to that second act 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 ChatGPT, 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 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.
Um I just think of times in HubSpot when things slowed down and there was churn.
It was usually my fault.
It was because there were some hard, you know, one-way door type decisions on my desk.
And you know, maybe every year I would sit down and I'd I'd open that one-way door or close it.
And it just freed everyone up, and we just started moving so much faster.
I think people need to be making those decisions and walking through those doors much more quickly than they used to.
I think that's new and different different.
I was someone who always valued optionality.
I think there's a massive tax on 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.
Yeah.
So 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.
And I know.
Yeah, it's hard to keep up as a card.
Luckily, we got some sweet podcasts to check out to keep up to date with what's happening.
We'll link to yours, of course.
Here's a puzzle for you.
What do OpenAI, Cursor, Perplexity, Vercell, Plat, and hundreds of other winning companies have in common?
The answer is they're all powered by today's sponsor, Work OS.
If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, skim, RBAC, audit logs, and other features required by big customers.
Work OS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SAS.
Whether you're a seed stage startup trying to land your first enterprise customer or a unicorn expanding globally.
Work OS is the fastest path to becoming enterprise ready and unlocking growth.
They're essentially strike for enterprise features.
Visit workOS.com to get started, or just hit up their Slack support where they have real engineers in there who answer your questions super fast.
Work OS allows you to build like the best with delightful APIs, comprehensive docs, and a smooth developer experience.
Go to workOS.com to make your app enterprise ready today.
Let's talk 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.
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 those halogenism.
The first is when you have to eat a shit sandwich, don't nibble.
Okay, I completely stole this from Ruth Porat, the CEO, the CFO of Google.
I saw her quote somewhere.
I'm like, that's it.
She's putting a perfect thing on it.
And I'll give you an example where I think this will play out over the next couple of years.
I think within the next couple of years, there'll be a real retrenchment in valuations.
And some will live up to valuations a lot.
Well, and like if I look at the public markets, they're very tight right now.
It's like the anti bubble.
I look at private valuations, it's like a real bubble.
I think there's a reckoning somewhere down the road.
And a lot of companies are gonna 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, 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.
Um, and I think people avoid that.
I think that's good advice, Ruth Ruth Porrot's giving.
Because you're gonna have bad news to deliver, bad shit's gonna happen to your company, even though it looks like it's going amazing right now.
You're gonna weird stuff's gonna happen and you're gonna have to deal with it.
And and we had a lot of weird stuff happen at Hub's HubSpot, and there's there's a basketball coach named uh Mike Sheshewski.
He's Duke's basketball coach, all-time winningest college basketball coach ever.
If you go to a Duke basketball game, you can hear him yelling from the side sidelines, Next play, next play.
And what's going on there is when a college basketball player is playing in the game and takes a shot and clanks it off the rim and misses it, they have a strong tendency to go play overly aggressively on defense in the backcourt, and many times compound their error by making a foul or something like that.
And what he wants to do is people to make their error, forget about it, and move back down the other core 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 Sheshewski'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 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 canceled.
I had a lot of customers yelling at me.
And I remember that company meeting.
I cried in front of the whole company.
I couldn't believe it happened to us.
And I remember using the next the next play um slide on that one.
Um, yeah.
Most of the we made a lot of mistakes at HubSpot.
A lot of bad things happened to companies, and most of them are self-inflicted.
And a lot of them are the old, the old saw, like uh companies are far more likely to die of of overeating than into digestion.
Usually it was we were trying to do too much.
I haven't heard that version.
I've always heard most companies die of suicide versus homicide.
Uh-huh, indigestion.
That's true too.
Oh man.
Um, okay.
So uh next halogenism, uh, never waste a good crisis.
There's something that people hear.
I'm curious, just kind of like what's the what's the lesson here?
And then is there an example of this with that uh that where you learn those lessons?
I'll just follow on to most of the good things that happened in HubSpot came out of a crisis because we would take, you know, pretty drastic measures to fix it and make sure we didn't do the same thing again.
And so in this particular case, we really rethought how we deployed software, how we thought about making software in a way that was incredibly healthy.
And I mean, we know we haven't had a serious outage since um the quality is much better.
And it kind of kind of an interesting thing with HubSpot is we started as a marketing software company and we pivoted.
We had Salesforce kind of came into our market.
We pivoted in CRM.
And one thing that we 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.
Uh, you know, good things come out of crisis.
You usually very good things came out of crises.
So is the lesson there?
Something's going wrong.
Is it just like overcorrect?
Like use this as a way to always overcorrected.
Yeah.
Swung the, we almost we uh purposely swung the pendulum hard the other way.
Which can connect to the first uh halogenism of uh if you're eating a shit sandwich and a 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 halogenism if you want to kill a plant, have two people water it.
I love this one.
It's very true.
Let's say, Lenny, you bought a new beautiful plant for your office, and then you went away for a month to Turks and Caicos because your AI agents doing your podcast, and you asked two of your friends, hey, can you would you mind watering my plant?
And there's one or two outcomes when happen to the plant.
The plant would either be overwatered and die or not watered at all and die.
And every CEO in the adults table has gone through this and they are religious about the DRI.
Like everyone talks about DRI in the in the kids' table, but once it gets to the adults table, like people get deep religion on it.
And 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 run that pilot project, everyone's on the same page, a salesperson, service person, developer, everyone's on the same page, and you go out and do it.
Yes, you don't bell.
When you get it scale, you've got a sales organization, you've got your forward-deployed engineer organization, you've got your product management organization, you've got some developers working on it.
Everyone's kind of separate.
No one knows really what's going on in the other departments.
And so let's say you want to really have a good pilot process, and you want to rethink it because you're scaling.
Everything important happens cross-functionally inside a company at scale.
And you need someone powerful uh to own 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 DRI 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 to work together.
Your advice here is that doesn't work.
Committees never work.
Yes.
Yeah.
Yeah.
Yes.
It's in DRI 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 alleganism, 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 it just takes a lot of lead bullets to get something done.
I think the way you wrote about it is it's always like one step forward, two steps back.
Talk about your advice there.
Yeah, I always thought incorrectly that we would have one hire or one investor or one event or one product release that would uh I was wrong about this, but it'd be a silver bullet.
And like the reality inside the HubSpot machine, the way it felt to me, it looks from the outside like over a long time up 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 that.
I in the thing about being a founder, CEO is there's no one, especially if you're you're in your 20s, is no one there to rescue you.
Your parents aren't gonna rescue you, your VC is not gonna rescue you, your teacher, your thesis advisor, you're kind of on your own and you got to figure it out.
And that kind of hits you when you hit your first crisis, like it's on you.
You can get some help, but it's on you.
Sometimes they have uh you in their corner if they're lucky at Sequoia, blood plug.
I can't solve it oftentimes.
I can be the shoulder they cry on, and I can give them advice, but it's still on them.
Do you feel like too many people start companies just like 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 gonna be much more painful.
I heard Jensen Wong say that.
Like, I wouldn't have started NVIDIA if I had it to do over.
I uh that if someone asked me that question, I would start HubSpot over.
It was very hard.
Um, there were a lot of sacrifices.
It wasn't glamorous at all.
But in the end of the day, I'm incredibly proud of it.
And, you know, I've, you know, on my deathbed, I'm gonna look back and be and really enjoy it.
And the Dalai 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 a 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 talked to.
I mean, pop 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 60 to 70 week hours a week for the entire time.
Never really turned it off, but that's kind of how I thought about it.
It's different now.
People are much more focused.
And I think Elon's inspired people.
Like, I had a starter back in the day, uh, nowhere near as successful as UpSpot.
But the way I thought about it is let me just give it everything I have and see what I can do.
This isn't the shot.
This is my chance.
Let me just give it all like forget balance, just go for it seven days a week for a while.
You know, and then you scale back.
Um and it's just like such an empowering thing to do for a while.
Just like, let me just try.
I'll give it my this won't be forever.
Yep.
And I know you've written about this, just like a balance for CEO 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 Garmesh had it.
None of the C the only CI CEO I know, and he's he's unusual in this way, is Kareem from Clay.
He's like, nope, you need balance, take the weekends.
Like he's got a different mindset.
I'm gonna have him on my pod to 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.
I did definitely free AI to dig along.
I wonder if there's a correlation, but it didn't 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 T V is greater than M E V.
What is that?
Okay.
EV is enterprise value, T B is your team's value, me V is your value.
And as HubSpot was scaling, and we had a lot of people who were VPs in different roles, and they started to get good sized organizations.
Where they would fall down was they didn't solve for me v, but it's all for TV over Eevee.
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 some as they saw for themselves, kind of suboptimized for their peers.
And the employee and their employees would notice it and complain about it.
Um it would be fine in the short term, but it would show up.
And the place it would show up, Lenny, was we did, and I think a lot of companies do this now, but we did a quarterly employee net promoter.
We did a quarterly customer net promoter survey and a quarterly employee one.
And we would we would have people rate it by the department they're in.
And one interesting thing about that, so it's like sales and service and engineering, all the different departments.
And we had an overall net promoter score, and then each department had a net promoter score.
And let's just take sales.
Sales net promoter score was like 65, 62, 68, 30.
Ooh, that's a big drop.
And then you read the comments, and it was not good.
A lot of complaints about the leader of that.
And a lot of the complaints were a little bit of this TV thing.
Um, and then we give feedback to that VP, would help them.
We give them all the comments, be like, you got this.
And then a quarter later, from 30 to negative five.
It almost, they almost never, they never actually recovered.
You lose your team, you kind of can't, it's hard to get them back.
Um, and that's why I say, you know, hire slow, fire fast.
And this doesn't show up in the first hundred, 150 employees.
Everyone's solving for EV, but as it gets bigger, and the CEO doesn't know anyone, and there's a couple layers between you and the employees, they tend to solve for TV.
So we always put on the wall, solve for Eevee over TV over me be, and then we added CV in front of Eevee.
Solve for the customers first, then for HubSpot, then the employee, 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.
You have 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 out goals.
Steve Steve Jobs had an interesting line.
He says, You don't work for your boss, you work for Apple.
I thought that was pretty good.
And that's I I heard that after I was CEO of HubSpot, but that kind of captures the sentiment.
And that's how I felt about HubSpot.
You work for HubSpot first, and then you work for your boss.
This is hard because you know, people's performance reviews are based on their goals, KPIs.
It's always like, here's what I got to drive.
Uh, other than putting posters on the wall, and this is our just HubSpot growth above all, is what matters, 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 got 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 in a little bit like Jensen runs NVIDIA, where I didn't do one-on-ones and I gave a lot of good and bad feedback publicly in large management team meetings.
And I definitely would go out of my way to criticize people if I felt like they were solving for TV over EV, and people got a sense for that.
Um, and then every quarter we did like a really well-produced company meeting.
We spent a lot of time on it.
And at the end of the company meeting, we we gave out we call them the champagner awards, which was a bottle of VOOV that my co-founder and I signed, and we'd read something nice about them and give it to them.
And usually there was an EV team in that.
And so we did different things to kind of beat that into people's heads.
Amazing.
So here is just celebrate people that focus on this and also include it in their valuation and performance reviews.
Yeah.
Okay.
That's a good segue to another halogenism where you talk about how companies are either customer-centric, employee-centric, or investor-centric.
And it's really important to know which you are.
And you guys actually shifted there.
What's what's your insight there?
Okay, we were very employee-centric.
Um, more than customer-centric in the first several years of HubSpot.
It's so much so that we the company was number one on Glassdoor's best place to work.
I was the number one CEO in Glassdoor.
And as I look back at that, I'm not sure that's a good thing.
Like wanting to be liked, I don't think is a good feature of a CEO.
And wanting it to be the best place to work probably isn't the right way to go.
Like if you look at Toby from Shopify, his scores aren't that good, but that company is doing really, really well.
Um so we overindexed on it.
And part of the reason we over indexed on it is my co-founder was really strong in this, and we had an incredibly powerful NFHR at NKD Burke.
And we just worked on it.
We we spent a lot of time 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 uh net promoter score is like 25.
I was like, we need to take I would give up 10 points of employee net promoter score to get 10 points of of customer net promoter score.
And so over some time, we shifted the center of gravity to customers.
Um, and where 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.
Like every time we had a management team meeting, we had our management team meetings once a month, not once a week.
And we would have a customer panel come on.
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 employee, we have a uh sorry, a customer panel at our board meetings, where 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 like, come on.
And it's a great way.
So the employees' voices here, those company meetings, we have the the customers in the company meetings.
We changed the comp plan.
So the management team got paid not on revenue, but on retention and that promoter score.
And so we work 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 what do you want to change how you 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 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, Annie, is as it gets bigger.
Like when it's small, everyone's giving you shit.
And like you're all on the same level.
But as it gets bigger, you didn't interview everyone, you had thousands of employees, you don't know everyone, and people put you on a pedestal that you don't deserve.
And let's say you're in the hallway and you're just kind of shooting the shit with a bunch of people, and you're like, ah, it'd be cool if we had a product that did that.
Somebody inevitably would go home and build that thing and 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.
Darmesh 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 just an FYI.
We had a whole system because we would say something on an email to the management team or Slack, and everyone would be like, okay, this is what they want, let's do it.
And sometimes it is like, this is you need to do this, and sometimes it is like we should talk about doing this, and sometimes it is this is just kind of an FYI, we're thinking about it.
And because it got big, we came up with that rubric 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?
So he was like, like one of them is plea, pleading you to do.
I'm not telling you to do this, I'm just pleading that you do what I ask.
Oh man, okay.
I like this all this all connects.
And by the way, you guys were co-founders for 20 years.
Um, you shared something before we started recording.
So Darmesh famously did not ever want direct reports.
He's just like, Brian, I want to start this with you, but I'm not, I don't want to ever manage anyone.
And you were talking about how you had to take on engineering, which didn't make any sense.
Oh, I'm an engineer, but I'm I can I can code, but it's not good.
And so when we started the company, it's like I was a CEO before, I was terrible at it, I want to do it again.
You're gonna be the CEO, I'm like, great.
And he's like, and by the way, I'm not gonna have any direct reports.
I'm like, well, it's just the two of us, so don't have to worry about it.
It'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 onboard them and making up big decisions.
And I would go to him and be like, Well, can you manage him?
He's like, Don't you remember?
I told you what I mean.
Surely you were kidding when you said that.
He said, Nope.
Because Darmesh Shah has never had a single direct reported up spot.
Incredible.
I don't uh it's just like a dream, a dream, a way to operate.
Uh, I love that you uh made it possible for him and it created all this opportunity for him to tinker and yes, it's a freedom up to really think and be creative.
Yeah, I'm excited to get him back on the podcast someday.
We're gonna link to that episode.
Maybe a last question.
I'm curious if there's anything else you think we missed.
As a as a company grows and scales, the job of a CEO changes.
You've written a bit about this of just like how different the job is when you're a starter versus a scale-up.
What are some of the things that most change on where your time goes as a CEO as the company grows?
I clicked on this earlier, but that inspiration thing, like I have a little rubric where it's like in the startup phase, it's 90% perspiration, 10% inspiration.
You get the scale-up phase, it's 90% inspiration, 10% perspiration.
And over time, you're doing every job in a startup, and you still need to be very attached to it and you still need to talk to customers.
You can't give it up.
But man, you have to let go of so much stuff over time in order for the organization to scale.
And I had a try I have trust issues.
Like I only trusted a small number of people at HubSpot to be a DRI and really drive something important.
It drove people crazy that I didn't have a larger trust surface.
Um, every one of the CEOs I work with has the same problem.
And that's a that's a scaling limit.
That was a limit for me.
Um, I wasn't trusting enough.
Brian, I feel like I could uh chat with you for hours.
There's a whole list of halogenisms 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 with us, Nedjuh?
I well, I would say if you're a CEO and you're interested in scaling, I think the Halligan as opposed to all the mistakes I made in my 15 years being CEO.
I tried to summarize them there to help you avoid them.
And I have a pod.
You should first listen to Lenny's pod because it's amazing, but I have a pod just for CEOs called Long Strange Trip, where I interview I interview CEOs about this.
So Lenny's interviewing me about being a CEO, I get to interview other people about being a CEO.
I'm kind of a CEO geek these days.
And the the name of the podcast is a grateful debt reference, which uh we haven't touched on, but you're a huge deadhead, as they say.
That could be a whole other podcast 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.
You know where they started, Lenny?
Um, no.
Palo Alto.
Their early concerts were at Stanford, were all over Silicon Valley.
They're a Silicon Valley company.
They were very first principals 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 crafts 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's the book called, just in case people want to dig 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 Grateful Dead cover bands that let them play it, but I I'm taking care of it for the Deadheads.
What's like one nugget of wisdom or lesson that people can take away from the Grateful Dead for startups?
Okay, people talk about spiky teams.
The Grateful Dead team was interesting.
Garcia himself was a bluegrass guy.
He was a banjo player.
And then Bob Weir recently passed, was kind of a country crooner, like country music.
Then their their uh bass player was an avant-garde jazz trombonist, Phil Lesh.
And their um keyboard player was a guy named Ron McKernan, Pig Pen, and he was like a harmonica guy.
And the drummer was like a marching band drummer.
And so spikiest of spiky teams came together and made a new genre.
They created a new category of music.
It wasn't rock and roll, wasn't sort of Rolling Stones, it wasn't Buddy Holly.
It was like this new thing.
And then they called it a jam band because they played rock and roll in a bluesy, open, organic kind of jazzy way.
And so spiky teams in creating categories, underrated.
Incredible.
Are you one of these people that have been to like a hundred Grateful Dead concerts?
By the way, okay.
Okay.
Uh this could be a whole podcast, but we're gonna we're gonna move along.
Um, okay.
With that, we reached our very exciting lightning round.
Uh Brian, are you ready?
Let's do this.
Fire it up.
I've watched you do the right lightning round so many times.
I'm flattered.
Um, 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 listened to podcasts, I'm on X, I talked 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 Andrewson on recently, and I don't know if you've heard his whole thing on how what he consumes.
He talks about he has a very barbell strategy to media.
It's uh either Twitter or books that are 10 years or older.
And I've heard we're not gonna say that.
I'm hearing him say that.
Um yeah, I kind of stopped reading.
I looked at that, I I was getting ready for this, Lenny, and I was like, I can't remember the last book I read.
I think this is gonna make a lot of people feel better that don't read books are like, all right, this is okay.
Um favorite recent movie or TV show you've 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's really like a disruptor startup, like so many startup lessons from those ear they're gutsy.
Talk about two steps forward, one step back.
Like they got into the details of how George Washington ran the army.
We were very close to losing that war most of the time.
And two steps, two steps forward, 10 steps back, two steps forward, 10 steps back.
Lots of lead bullets.
A lot in like in like unless we had alliances, like we had alliances with the French, we were screwed.
Uh so I love that.
That it's a long one, but it's really good.
How long is this?
What are we getting into?
Probably 10 plus hours.
10 plus hours.
Whatever.
It's a lot.
Uh, but uh worth it is what I mean.
I'm in Boston, you know, it's revolutionary war.
Surrounded by history.
All right.
Uh, favorite product you recently discovered that you really love.
I love my Delphi clone.
I teach a I teach course uh called Scaling Entrepreneurial Ventures.
And um, I don't do I don't do office hours.
I have Delphi do my office hours.
Very happy with that.
The my favorite feature of Delphi and again, LennyBot.com, there's my Delphi, though we both have little bots.
Uh the voice feature is the coolest thing, right?
Great, not good, great.
I can't wait.
I had video, they get rid of it, they're gonna bring it back.
Can't wait till 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.
Yeah, it's like so good in so many ways and so annoying in so many ways.
Oh annoying.
But like we still use it, you know, there's nothing better.
You're 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 what these bots are, just so people understand how cool this is.
So minus training on every single podcast, like this one is gonna be sucked into it, and every single newsletter.
And you just talk to it and ask it like, how do I find product market fitness based on everything I've ever shared?
Here's here's your steps.
Okay, what's even better about it is is you because you can go to ChatGBT 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 the things I've ever shared.
Nah, that's not tell, let's not tell too many people that because it's one day I'm gonna pay wallet in the near future.
Anyway, enough about that.
Lenningbot.com.
Do you have a favorite life motto that you find yourself coming back to in worker in life?
This isn't lightning, but four years ago, I had a very bad snowmobile accident, drove the 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.
I woke up and I didn't think I had my phone.
So I sat there for a long time.
I'm like, I'm probably gonna die tonight.
No one knows where I am.
It's frigid out, it's in Vermont, and I'm gonna freeze to death.
And I sitting there for a couple hours, I finally was like, Oh, I do have my phone.
Dialed 911, by the way, 911, amazing service.
And so the helicopters came in, 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 I you can't see a bucket metal all over me, all in me.
Life short, like, life short.
And I I made some decisions at the bottom of that cliff.
That the one of the decisions I made at the bottom of that cliff was I don't really like being CEO of an 8,000 person company.
Doesn't really suit me.
Like my harmonic motion is off.
I don't love the day to day.
If I make it out of here alive, I'm out.
And so that's exactly what happened.
Like the first big thing that happened coming out of that was I gave the job to Yamani, 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 gonna live forever, and they're not.
Um, as somebody who's 58, yeah, life's very short, and I'm much more intentional about the decisions I make, much more intentional about the people I hang out with today than I was before that.
And I really try to work on things that bring me joy, like this pot.
Same.
I I appreciate it.
Um, I read that you had 20 broken bones in this accent.
A lot of broken bones, a lot of metal.
I got 33 screws in me, one loose one up here, Lenny.
Same.
Okay.
Uh last question.
We talked a bit about the Red Sox.
You're uh 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 deeply flawed.
It doesn't have a salary cap.
And so you've got the Dodgers, who I take my hat off to, have like a $400 million payroll, and then Miami Marlins are like a hundred million dollar payroll.
And in other leagues, that all kind of balances out pretty well.
Baseball sort of it's it's set up incorrectly.
I think it'll correct uh in the next couple of years, but um, it's kind of it's a broken model.
Intriguing.
Uh stay in AI SAST if you want to make money, is what I'm hearing.
Vertical SAS.
Uh Brian, this was incredible.
Uh covered almost everything I was hoping to cover.
Uh, two final questions.
Where can folks find any line if they want to reach 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 Sequoia founder?
Uh, and then how can listeners be useful to you?
I think there's two things.
I would love folks to listen to Longstream Shrimp, my pod.
And I would I'd get some comments, but not a ton.
Like Lenny, you have more comments than yours.
I'm jealous.
I'd like just feedback on how I'm doing.
Like it's very new.
And it just started a couple of months ago.
It seemed like it's going pretty well, but like it's my family and Sequoia people giving me feedback on it.
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 uh what they think.
The real, real honest face.
Read feedback.
Okay, cups.
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, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.
Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast.
You can find all past episodes or learn more about the show at Lenny's Podcast.com.
See you in the next episode.