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

00:00:00The thing about being a founder CEO isthere's no one there to rescue you. Yourparents aren't going to rescue you. YourVC is not going to rescue you. That kindof hits you when you hit your firstcrisis.>> Starting a company has never beeneasier. Scaling one into a durable, highimpact organization has never beenharder.>> The number of companies formed is goingto mushroom over the next 10 yearsrelative to the last 10 years. It's justgoing to be hard to stand out [music]and really accelerate. What's mostdifferent about what it was like to be aCEO maybe 10, 20 years ago versus today.There's a massive tax and optionalitywhen you can move this fast and try[music] a lot of things. It putspressure on the CEOs to be faster and[music] better decision makers. A lot ofpeople in the world want to be founders.They want to be cos. I don't thinkanyone [music] can do it. People talkabout 996. It's way more than that.Founders are 7 days a week. They'realways on. I text Sunday nights. It'sfull contact. Do you feel like there arespecific profiles or traits to besuccessful? I look for four things.[laughter]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 podcastbecause he is more than anyone I've meta student of the job of a CEO. Afterleaving HubSpot last year, he became thein-house CEO coach at Sequoia, where hebrings together dozens of

00:01:15top CEOs tolearn from each other. He doesone-on-one coaching with some of theworld's top CEOs. He also hosts apopular podcast called Long Strange Tripwhere he interviews some of the world'smost successful CEOs. In thisconversation, we unpack what it takes tobe a successful CEO in today's era.Let's get into it after a short wordfrom our wonderful sponsors.Applications break in all kinds of ways.Crashes, slowdowns, regressions, and thestuff that you only see once real users[music] show up. Sentry catches it all.See what happened, where, and why. downto the commit that introduced the error,the developer who shipped it, and theexact [music] line of code all in oneconnected view. I've definitely triedthe five tabs and Slack thread approachto debugging. This is better. Sentryshows you how the request moved, whatran, what slowed down, and what userssaw. Seir, Sentry's AI debugging agenttakes it from there. It uses all of thatSentry context to tell you the rootcause, suggest a fix, and even opens aPR for you. It also [music] reviews yourPRs and flags any breaking changes withfixes ready to go. Try Sentry and SERfor free [music] at centry.io/lennyand use code Lenny for $100 in Sentrycredits.

00:02:30That's sen [music]tr.io/lenny.This episode is brought to you by DataDog, now home to EPO, the leadingexperimentation and feature flaggingplatform. Product managers at theworld's best companies use Data Dog, thesame platform their engineers rely onevery day to connect product insights toproduct issues like bugs, UX friction,and business impact. It starts withproduct analytics where PMs can watchreplays, review funnels, dive intoretention, and explore their growthmetrics. Where other tools stop, DataDog goes even further. It helps youactually diagnose the impact of funneldrop offs and bugs and UX friction. Onceyou know where to focus, experimentsprove what works. I saw this firsthandwhen I was at Airbnb, where ourexperimentation platform was criticalfor analyzing what worked and wherethings went wrong. And the same teamthat built experimentation at Airbnbbuilt EPO. Beta Dog then lets you gobeyond the numbers with session replay.Watch exactly how users interact withheat maps and scroll maps to trulyunderstand their behavior. And all ofthis is powered by feature flags thatare tied to real-time data so that youcan roll out safely, target precisely,and learn continuously. Data Dog is morethan engineering metrics. It's wheregreat

00:03:45product teams learn faster, fixsmarter, and ship with confidence.Request a demo at data dogq.com/lenny.That's data dogq.com/lenny.[music]Brian, thank you so much for being hereand welcome to the podcast.>> Thanks for having me, Lenny.>> It's my pleasure. I want to start withsomething that I've heard your boardmembers, the way they described you isuh someone with a perpetual state ofconstructive dissatisfaction.Do you think this is a core foundationalkind of uh trait of successful cosuccessful leaders?>> By the way, I like that description. Iwhen she did a woman named LoriNorington who's sub chair said that Ilike it. I took it as kind of acompliment. Um, and I and I liked it.And as I so I spend most of my timethese days coachingvery fast growth CEOs. They all are kindof like that. Um, they're they're all inkind of a state of perfeualdissatisfaction, but in a positive way.One of the things, by the way, I likeabout the current crop of CEOs,

00:04:55they don't really take stock of whatthey they've done and and feel it.They're always a little bit dissatisfiedwith where they are and very focused onthe end state. And I've been surprisedat how humble this generation is ofCEOs. And I think of my generation ofCEOs as being I don't know I wouldn'thumble wasn't the first word that wouldcome out of your mouth when you describekind of my generation but thisgeneration I feel like is is different.Um and I've been impressed with it.>> Okay. I have a bunch of questions alongthese lines. Um because one you've beena CEO of an incredibly successfulcompany for a long time for about 20years before you moved on to this newchapter. Now you work with a bunch ofCEOs. You're the you're Sequo's in-housecoach. There's a few things that I'veheard you do. One is you gather groupsof cos and uh what I've read is that youhave kind of two tables. You have thekids table and the adults table. Thekids table of cos that are companiesthat are about under 100 employees. Theadults table is over 100 employees. Uhso let me ask you just when you look atcos that move from the kids table to theadult table other than just you knowthey scale and grow. What is it thatthese cos that graduate from kids toadults table uh

00:06:10do differently?>> The adults are are really focused onand all they really want to talk aboutis their exec team, their directreports. How do you build our exec team?That next level down org design. Youwould be surprised how much they thinkabout that. And on average, I would saythe adults are spendinghalf their time just recruiting andinterviewing. It's pretty all-consumingand I remember that from that phase inHubSpot's growth and it surprises peoplelike wow my job is really just tointerview and hire. I didn't know thatwas going to be the case. Um so that isone that they kind of are making thattransition and I would just say ingeneralpeople are very bad at this and HubSpotwas too.I think CEOs and everyone dramaticallyoverrates their ability to interview andoverrates their gut feeling andunderratesa really high quality blind reference.And I interviewed uh Dave, the CEO fromMongoDB the other day and he had aninteresting stat. On average over hislike 10year lifespan

00:07:25as a CEO ofthere were two sea level two sea levelsturned over per year. That's a lot ofturnover at the top. And I didn't keeptrack of it like Dave, but I'm thinkHubSpot was kind of similar. And all ofthese startups are kind of similar too.And so people are working on that andstruggling with it uh as one thing incommon like with all of them.>> What do you do when you coach someone onthat when you're like okay you thinkyou're amazing at interviewing, youthink you know who's going to work out?What advice do you give them to helpthem develop that skill?>> I think even me, I've been doing thisfor 150 years. I still think I overability to interview someone uh andreally know if they're a good fit. Um,I give a couple pieces of advice. ParkerConrad has a good hack that I like. Uh,[snorts]before he's got a sea level interview,CFO, chief product officer, whatever, hehas him sign an NDA and sends them thelast board deck or the board memo orsome important doc, and he schedules ahalfhour interview with them. And hejust has a chat about the debt. And ifthey're just very complimentary and it'sso great, you're doing this amazingthing,

00:08:40it's a major red flag to himbecause he wants someone that willchallenge him and not a yes person. AndI thought that was a pretty good hack toget inside someone's head and how theythink and how they'll interact with you.Um, getting on a whiteboard and workingthrough a problem, I think, is always agood thing. I think the standardinterview of walking through yourbackground, I don't think is all thatvaluable. Um, and I coach people to doblind references. Find someone you knowthat work with them. VCs are good atthis, by the way. AndI get a lot of these and you can tellsome of them are like, "We've alreadydecided we're checking the box versusthey're asking me hard questions aboutthis person." And one of my favoritequestions people ask is, "Would youenthusiastically rehire this person forthat role?" which I think is a reallygood question. On a scale of 1 to 10,how likely is it that you'll try torehire this person back from me down theroad? I think those types of questionsare good. So, not mailing in on thoseblind references, I think, areis really good. My other piece ofadvice, and no one listens to me onthis, is is hire slow and fire fast. Umpeople hire fast and fire slow. Uh, and

00:09:55if I had to guess, Lenny,within 18 months after you hire a sealeexec, at least 50% of the time they'regone. There's this there's [laughter]high mortality rate on them. It's it'sharder than people think.>> And what so what you're saying here isthere's only so much you can actually doto increase those odds.>> I think you can I I I think you can youcan um I think the blind references arekey. I think doing like real interactiveworking on a project together. I'll tellyou one other thing we learned atHubSpot about this like we would have acandidate come in let's say a head ofengineeringand we'd have like eight peopleinterview them and our scale is one oneto four and let's say four people werefour out of four and four people weretwo out of four. So that's candidate Aand then the next candidate comes ineight people interview them andeveryone's a three out of four. Almostevery time we hired the three out offour, like the person with the leastamount of weaknessesand we changed it and we we went withthe spikier people. We went with peoplewith weaknesses. We went with peoplewith challenge stuff. And that hasworked out quite well. Like our hit rateat HubSpots improved. We also haveshrunk the the pool of people on thatinterview panel

00:11:10from eight to like four.Like we just hired a a head of productand there were just four of us thatinterviewed them. I think that workedtoo. Um, so I think there's things youcan do to get better at it for sure.>> Okay, this is incredibly tactical anduseful. On the references piece, uh, thetoughest part is getting people to behonest because there's very littleupside to them to say negative thingsabout people. Is there anything thatyou've learned to help get real honestanswers from folks you call forreferences?>> Well, I can just say because I don't dothis a lot anymore, but when people callme, I can tell if they've alreadydecided. Mhm.>> When they're really just looking forlike [snorts] when they ask me for thestrengths and weaknesses, I'm like orthey've already decided. When they askme something hard like on a scale of 1to 10, how likely are you to hire themagain? Stuff like that that kind of getsat the core. Or were they the top 1% ofyour employees? That's a good question.Oh, were they top 10? Oh, you know, thattype of question is pretty good. Uh, sowhen I'm on the other side of it, I likewhen I like when those types ofquestions come up. I tell you the othermistake everyone makes I made and allthe CEOs are making now isyou're hiring for

00:12:26that whatever head ofengineeringand you're blown away by the resume likeyou're 50 employees and you're hiringthis person who's been at Microsoft thelast 10 years and has a fancy title andfancy division in Microsoft and you hirethem there's just a massive impedancemismatch when you hire them on whattheir expectations are what yourexpectations are in the in the in theextent that you've got yourtogether.It's just you don't you definitely don'tuh if you're 50 or 500 employees andthey expect you to have your acttogether and so that is another likeavoid the big company hire like we hiredso many people from Salesforce andGoogle Microsoftlike 100% you know attrition rate on allthose folks. Something that I've seen ata lot of companies is there's likephases of like, okay, now it's like theMcKenzie a cohort comes in and we thinkthat's going to be the answer and thenit's the Apple group and then thatdidn't work out. Then the Amazon group,>> the Mackenzie one never works.[laughter] It never works.It never works. Like by definition, theywould fail on my spectrum of like mostfounders are like me. Like they areskeptical of conventional wisdom.They're unhappy with the world works insome way. And so they're kind of far onthat spectrum of of rethinkingconventional

00:13:41wisdom. And almost bydefinition, somebody who goes to workfor McKenzie is very conservative intheir outlook. Um, and so I think thatalmost always fails.>> We're on this hiring kind of thread, solet me keep following this conversation.Uh, I read somewhere that you recommendbuilding your team like the 2004 RedSox.What does this mean? I'm a Well, I'm abig sports fan. a big Boston Red Sox andthe Boston Red Sox hadn't won Lenny aWorld Series in 86 years since theytraded>> and they finally broke they finally wonit in 2004 and the way they won it wasthey had a team of a bunch of homegrownreally high quality inexpensive talentthat they drafted and came through thefarm system and then they got a few freeagents like David Ortiz that a lot ofpeople have heard of that they paid afair amount of money to Pedro MartinePedro Martinez as and Kurt Schillingwere kind of the canonical older beenthat been there done that bigger companyfolks and they mixed really nicely. Theculture really worked and I think that'sthe key. I think people underrate theirhomegrown talent like almost across theboard they underrated and I think youwant that mix. You don't want to hire awhole bunch of been there done that. Youdon't want to

00:14:56hire none of them.>> I don't I imagine this is public butyou'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 alongthose lines. Okay.>> Okay. That's uh that's amazing advice.Uh kind of what I'm taking away here ispeople see all these fancy logos,amazing person, VP this, that atSalesforce, Amazon, Google, whatever.And what you're saying here is uh don'tunderestimate the power of someoneinternal uh rising to the occasion.>> Yeah. If you look at HubSpot, like halfthe management teams are folks that havebeen there for approximately 150 years,which I like. And same with like youlook at Apple, a lot of those people arehomegrown. And so is there any tips herefor doing this? Well, is it just likegive people a chance?>> I tend to give people a chance. It'slike if you're interviewing someonethat's homegrown in their VP for thatseale job versus hiring someone from theoutside. You hire someone from theoutside. They're very good atinterviewing from a big company. Theylook fancy. They're shiny. You haven'tseen their warts. Hard to figure outtheir warts unless you're very good atplan referencing. And so you tend tooverrate them and underrate yourhomegrown. So, if it's pretty close, Ithink you'd give your homegrown shot atit. What's interesting to me, Lenny, is,you know, Brian Chesy sort of rethoughta lot of this stuff. And he's like,everyone's

00:16:11over over rotating to thehome grow to the um, you know,experienced talent and management teamsand delegation. And I think he's mostlyright about that. People haven't reallyfollowed that. People are, you know,they're hiring people from the outsidequite a bit. That's kind of the standardpart of the playbook that all of themare following now. It's a littledifferent. It's actually quite differentthan what Brian's espousing.>> Going back to the conversation aroundCEOs. A lot of people listening to thispodcast, there's a lot of people in theworld want to be founders. They want tobe CEOs. At the same time, you look atElon, you look at Jensen, you look atSteve Jobs, you look at you. A lot ofpeople are like, I can't. I'm not thisperson. I'm not I'm not going to be asgood as them. How there's no world whereI'm this good. Do you feel like thereare specific profiles or just liketraits that you have to be born with tobe a successful CEO or do you think it'sall learnable? Anybody can be successfulif they really work hard in school. Imeet all these CEOs coming in and I havea little like algorithm in my head and Ilook for four things. [laughter] I callit my lock algorithm. L is for lovable.Andyou know, Steve Jobs, you would say, iskind of rough and maybe not lovable, buthe would inspire followership. You wouldwant to follow him.

00:17:26And so, could Ienvision a 28-year-old me graduatingfrom business school going to work forthis person? Would I crawl across brokenglass? That's question one.Two is just obsession. Are they deeplyobsessed with this problem? Did they I'ma little negative on people who came upwith this problem to solve six monthsago and started a company. I like peoplewith deep founder market fit who've beenthinking about it for a long time andhave evidence in their lives of goingdeep down obsessively down a rabbit holebecause that's kind of what it takes tobe a founder CEO. The C is something Iwouldn't have thought of, but this is asequoia thing like chip on the shoulder.Pretty much all of them have a bit belike a boulder on their shoulder. And II have a bit of a chip on my shoulder,too. And the K is just for deeplyknowledgeable about the domain. [snorts]And so I kind of look for that. Um, if Iwere to stick an S on it, I would saystudent. Like I look at Winston Weinbergfrom um Harvey or James from Profound orGabe from Rogo, some of these new veryfast growing companies. They're

00:18:42studentsof the game. They're not just learn italls. They're deep, deep, deep studentsof the game. And they're they're likeLLMs. They're constantly constantlylearning. and it's not just learningstuff for me and their peers, but theygo way back in time and have a lot ofhistory on stuff. So, those are some ofthe that's kind of my little criteria Iuse when I'm evaluating CEOs. What doyou look for, by the way? You'veinterviewed you've interviewed a ton offolks like me. What do you think's incommon>> of what successful founders? Oh my god,I wish I had the uh my succinct answer.I would ask I would go to lennybot.comand be like, what is the common patternacross these folks? One that you didn'tmention that I think is interesting. Idid some research on this recently withTerren Rohan. When it's just extremelyambitious, just trying to do somethingreally wild that most people are likethat's crazy. You're not going to likeget a subscription service for all musicin the world. That's just what are youdoing? Do it and you're going to dothat.>> And like is it learnable? I know noticesome of the a lot of the CEOs strugglingwith a couple things. Like let's sayyou're you're Winston, your late 20s,you've never managed a team. you'reprobably never even captain of a sportsteam before.And in order to scale, like you have togive people

00:19:57feedback like constantly andit's very unnatural. It's like I'm goingto give this this VP I hired a bunch offeedback, positive and negative. And ifyou don't get good at that, you payreally pay the price later.That's something I think they have tolearn. They all have to learn to get agood detector.They're constantly being spun.Everyone's trying to sell to them. Theorg is always trying to sell to them.So, that's sort of something they haveto develop, you know, over time. Theyhave to all get good at the inspirationthing over time. Like you're you'reWinston. You've never had to inspireanyone in your entire life. You know,[snorts] you're you went to school andyou're a lawyer for a few years and youstarted this thing. Like inspirationwasn't your thing. So there's certainthings you have to kind of learn on thatstartup to scale up path and the bestones learn it very fast.>> This is extremely interesting anduseful. So lock uh with an s at the endjust to kind of mirror back what you'resharing. So what you and when you weresaying you evaluate cos is this for likeinvesting as a okay so when you'rehelping Sequoia decide should we investin this company what you look for is uhlocks I like the s I'm going to includeit there. So are they lovable? Are theyinspiring? Uh,

00:21:12oh, are they obsessedwith this problem they're going after?Uh, do they have a chip on theirshoulder? Are they extremelyknowledgeable about the problem they'regoing after? And it sounds like not justthe problem, but just the studyingcompany's business strategy, things likethat.>> And then S was a student. I guess that'swhat S is student is studying this uhbeing 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 youthink they're made? Can anyone turn intoan amazing student?>> I don't think anyone can do it. I don'tthink it's just anyone. I I will sayI've noticed that so another littlerubric I have and I don't see a lot ofthese but like Brett Taylor's one.There's a few out there that are inKoa's portfolio. I call them a back tothe baseball thing, a 52 player. Inbaseball when you rank a player, it'scan they hit? Can they hit with power?Can they run? Can they catch a ball? Canthey throw the ball? And they they ratethem kind of one to 10 at each. And it'svery rare that you have a five toolplayer, like extremely rare. Andthe thing that's kind of new now arethere are five tool CEOs like BrettTaylor's one. You can code, you havetaste, you have vision,

00:22:28you can sell theproduct, you can convince employees likethis kind of super CEO. And there's abunch of them now. AndI don't know, I didn't see a lot ofthose. That certainly wasn't Steve Jobs.He wasn't writing pro, he wasn'tprogramming. Um, it wasn't Jeff Bezos.Uh, you know, I think there's kind of anew breed that's quite impressive.>> These folks you mentioned, uh, were thisgood before AI became a thing. I imagineAI helps more cos fill the gaps thatthey have.>> I think it's it's hard to fill the gapof, you know, this guy's a developer.He's brilliant, genius level, obsessive,but can he convince can he sell? Can heconvince an investor to give him a lotof money at a high valuation? Can heconvince brilliant employees to leaveOpenAI and join him? Um, can he convincesome big skeptical Fortune 500enterprise to buy his product? Likebeing able to do that and have taste andbe able to code really well at nextlevels, I think is rare. I actuallythink it might be the other way thoughwhere mere mortals like me who can kindof code all of a sudden we're going tobe able to build stuff. I think it kindof goes the other way. I love this listyou shared

00:23:43of things that you find cosmost have to learn. Uh BS detection, uhinspiring people, giving heart feedback.What's maybe like the one thing thatmost often people that become cosfounders have to work on? Is there likea most common thread of like here's thething you probably need to work on most?It's that feedback thing.All of the CEOs are building their teamsand so many are like, I have aco-founder that runs product andengineering, but I need that co-founderto kind of step asideand be the CTO and the thinker and thelabs person, and I need to hire somebodywho can actually run the engineeringmachine. Like so many of the CEOs aregoing through that right now. Uh that'sa tricky transition. So many of the CEOsare layering folks like you hired thatearly head of sales. He hired 10 peoplebut just can't quite figure out thesales profile. Can't quite unpack thesales process. Can't quite forecastaccurately. We need to layer the person.You know, those types of conversationsare very tricky and quite unnatural forhomo sapiens to have if you're, youknow, you're 25 and you've never doneanything like that before. So, I

00:24:58see thebest ones getting really good at thatand studying it. It and it's it's superuncomfortable, but they have to kind ofsuck it up and get good at it.>> What do you find most helps them buildthese skills, get better at this? Isthere some kind of tidbits of advice yougive them? Is it something that theystudy to improve? I>> I think misery loves company on this. ofwhat I do. Like the kids table is 15CEOs of companies under 100 employeesand the adults table are CEOs ofcompanies over 100 employees about 15 ofthem. They talk about this with eachother. It's kind of a safe space and Ican weigh in, but it's actually muchmore effective when their peers weighin. I think misery really does likecompany on stuff like this. They learnfrom each other.So essentially it's find peers to talkto and share and be component of>> and the reason I break it out is likethe problems at the kids table are verydifferent than the problems at the adulttable. Um and and they all they all rhythey rhyme a lot.>> So you teach a course at MIT aroundscaling startups and it's specificallyaround scaling not startups not startingthe company and you have this quote inyour uh syllabus starting a company hasnever been easier scaling one into adurable high impact organization hasnever been harder. Why is that the case?I mean, has it ever

00:26:13been easier to starta company? It's>> absolutely true. [laughter]>> And the flip side of that isI mean, how many companies is the thethe number of companies formed is goingto mushroom over the next 10 yearsrelative to the last 10 years. And thethe last 10 years compared to theprevious 10 years is mushroom. I justthink in my life like I'm old and when Iwas a kid I'd walked into CVS corndrugstore and I want to buy a toothtoothbrushthere four or five there you pick oneandyou know in the n in like the 90s or2000s you go to Amazon there are four or5,000 toothbrushes [laughter] four or5,000 companies creating thosetoothbrushes it got much much easier tomake stuff and even technology AWS justmade it easier to start a softwarecompany. So, it's like a huge jump backthen when we started up about 2006, butnow it's going to be an even biggerjump. So, it's easier to start now.There's so much noise in in con in uhcompetition, it's just going to be hardto stand out and really accelerate andscale. So, that's why I say it's neverbeen easier to start. There's never beenmore competition. It's never been harderto scale.>> And a big part of this is isdistribution essentially. Breakingthrough the noise is what I'm hearing.>> And it's hard to learn that like you

00:27:28didn't grow up doing distribution. Youdon't know. So they they're all learningit. Um and the ones that learn fast,it's like a learning game. The fasteryou learn, you know, the better you do.>> Along these lines, I saw you tweet thisrecently where uh people talk aboutwhich jobs AI is going to replace andyou uh said that sales is maybe the lastjob AI will replace. What why do youthink that's the case? Well, if you lookinside a typical enterprise, likewhere's AI like really working?Let's say inside of HubSpot, softwaredevelopment is working incredibly well.[laughter]Uh customer support incredibly well.Um legal starting to work incrediblywell, but there really aren't apps likein the rest of the org that have reallychanged things a lot. And in the go tomarket side's been kind of slow uhreally just support like there isn'tlike a canonical marketing or sales ormaybe the BDR is the first one but Ithink ye old enterprise sales wherethere's actual trust built up betweentwo carbon based life forms I think willbe very very very late to go in thewhite collar world. I also I think a lotabout the go

00:28:43to market.I think the go to market's going to getturned on and said like when I when westarted HubSpot if I think of the waythe funnel worked you want to get foundin Google someone clicks on a blue linkthey land on your website they go downthe rabbit hole they clicked on contactsales they wait until that sales rep'sready go down that rabbit hole and Ithink it's going to get turned on itshead where people are evaluating aproduct they start in Gemini or theystart in Anthropic or they start in chatBT and you know for example chat knowsway aboutIt knows everything on your website,everything beyond that knows all yourcompetitors. So they they will stay inthere and do lots more research and beincredibly well educated. So yourwebsite's a lot less important and theygo to your site. I think sites willchange where you're going to have areally high quality avatar that knowseverything about your products, knowseverything about your company and yourpricing and packaging and you can have ahigh quality conversation with thatperson. that person that will get storedin your CRM and and will get um you knowscored this is good quality conversationand then the sales rep will follow upbut that sales rep will being an avatarwith them on every sales call you won'thave to wait for their SE they'll havetheir own SE that's all knowing thatwill follow them through the process so

00:29:58go to market hasn't changed much yet butI think over time it's going to change alot this avatar just understand so thisis uh the buyer has their own littleagent that comes with them or onHubSpot, you have this avatar that walksyou through the sales process.>> I I I I I think both. I think me as aknowledge worker,>> like what I really want as a homo sapienis I have like a deli clone that Ireally like.>> Same.>> It's actually quite good.>> Yeah. Where where do people find yours?>> Uh they find it on my footer. They canfind it on>> del. We'll link to it.>> Yeah. And what I want is like connectthat that thing to my email into mygranola into my plaude and it knowseverything about me. And then when I goto a meeting, Lenny, I want to invite Iwant to invite that thing to my meeting.So it's sitting there in the Zoommeeting. It's not just taking notes likegranola. It's a participant. So if Iforgot something, I asked it a question.If somebody else forgot like I thinkevery knowledge worker will have one ofthese in three, four, five years. Butmine was more on the go to market sidewhere I think every website will changeand there'll be a an all- knowing avataron that homepage. And

00:31:14if it's aconsidered purchase, I think it getshanded off to a sales rep. That salesrep has a conversation, but when thatsales rep's on Zoom, they have their SEavatar that's kind of all knowing. So, Ithink this stuff all changes a lot inthe next few years, but it hasn't reallyunlocked yet.>> What are we going to be doing in thisworld? These two bots chatting with eachother.>> It's going to be great, Lenny. You and Iare gonna be like sitting on a>> podcasting kickos relaxing on amonthlong vacation sending our avatarsto all the meetings.>> Go buy me some Hub Hubspot seats,please. I think this is why Cloudbot wasso popular. I think this is essentiallywhat they're building is this idea whichis now called Moldbot, which might bechanging again. Uh it's just like thispersonal little agent that can go dostuff for you.>> Totally.So you're talking about the future of goto market is this world where there'sthese little bots and agents that aredoing things for you both on on bothsides. When you look at companies todaythat you work with that are doing wellthat are especially AIdriven companieswhat are they doing differently in termsof go to market that is working reallywell?>> Honestly the only thing that's differenttoday it's exactly the same as it's beenfor 100 years except they call theirsees or their system consultants fordeployed engineers. the rest [laughter]of it is the same. I thought it would betotally different

00:32:29in AI. I'm workingwith all these companies. They're hiringlike all the same folks and running thesame enterprise sales processes. So, ithasn't changed that much, at least onthe enterprise side. It actually hasn't.I spent the first 10 years of my careerat a company called PTC, which is likean enterprise sales machine. Enterprisesales hasn't changed that much since the1990s.>> Okay. And so, for a deployed engineer,very hot term. Uh the idea there is theycome work with the the c the customerand help them implement this thing. Andthat that's come up a lot on thispodcast just with AI tools. Rarely arethey just plug-and-play. You can't youcan't just like set up some agent thatfigures everything out. Takes a lot ofonboarding and integration. Is itactually a different thing at all otherversus like sales engineering in thepast things like that?>> It's a solutions consultant salesengineer. They're technical. They helpyou implement it. They connect all yoursystems. They customize it. It'sdifferent. I mean, you're training it ina different way, but I think well,anyway, I think the term is fine. I I'msort of being light on it because boy,it looks similar, except that role has adifferent name to it.>> Got it. So, if anything, the advice I'mhearing here is just lean into this uhcontinue to lean into this idea ofhaving your employees help the customeron board, be successful, integrate, allthat stuff. I think the thing that will

00:33:44change first is the top of the funnelaround getting found in instead ofGoogle, you got to get found in in inthese>> Yeah. AEO.>> Yeah, that's going to be reallyimportant. And the way you build yourwebsite is very different for that tooptimize for it. Um and then your Ithink your homepage is totallydifferent. I think you land on an avatarand have a conversation with them versusyou're going through all the pages onyour site. I I think the top of thefunnel is about to change a lot.>> Is anyone doing this well yet? this ideaof this avatar or is this just kind of ain 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 morequestion around CO stuff and then I wantto move on to haganisms.>> All right.>> Um>> how is just being a CEO different thanit was? So you've been doing this for20ish years.>> Yeah.>> Um what's like most different about whatit was like to be a CEO maybe 10 20years ago versus today? One of my CEO, Iwas actually Winston from um Harvey saidthis like a year ago and I was likethat's But I actually think hewas right. He's like you can just do alot more. I mean you've got AI agentsdoing stuff. Everyone's more productive.The software developers are moreproductive. Like something that used totake you a year takes two months now.

00:34:59And so the amount of projects and theamount of stuff you can do is much muchmore. I think he's right. I think that'sa little dangerous. Like let's say youfound your beach head market and thatbeach head market is really good andit's very deep. There's a lot of work todo. I think what's dangerous forcompanies is they hop to that second acttoo quickly. Uh and they lose focus onthat first act. And this isn't acompletely perfect analogy but like youthink of OpenAI and CHPT and it's aconsumer app is doing incredible andthey're doing lots and lots and lots andlots of other things and then Geminicomes out and they've kind of focusedback on the core. Uh I think there's alot of competition. Everything's movingfast. I I do think people get more doneand I think that impacts everything.Like the planning cycles used to be ayear. I think the planning cycles noware 3 months long.Yeah, that's a big change. I think itputs pressure on the CEOs to be fasterand betterdecision makers. Umlike I just think of times in HubSpotwhen things slowed down and there waschurn. It was usually my fault. It wasbecause there were some hard, you know,one-way door type decisions on my

00:36:14desk.And, you know, maybe every year I wouldsit down and I' I'd open that onewaydoor or close it and it just freedeveryone up and we just started movingso much faster. I think people need tobe making those decisions and walkingthrough those doors much more quicklythan they used to. I think that's newand different. Different. I was someonewho always valued optionality. I thinkthere's a massive tax in optionalitywhen you can move this fast and try alot of things. So, I do think the job'schanging a lot.>> Yeah. And there's so many reasons thisis happening. One is just technology isjust like every week there's a new shiftin what is possible.>> So, if you're spending all these monthsthinking and planning just like what awaste of time it ends up being cuz somuch is changing. And>> I know. Yeah. It's hard to keep up.>> [laughter]>> Luckily, we got some sweet podcasts tocheck out to keep up to date with what'shappening. We'll link to yours, ofcourse. Here's a puzzle for you. What doOpenAI, Cursor, Perplexity, Versel,Platt, and hundreds of other winningcompanies have in common? The answer isthey're all powered by today's sponsor,Work [music] OS. If you're buildingsoftware for enterprises, you'veprobably felt the pain of integratingsingle signon, skim, arbback, [music]audit logs, and other

00:37:29features requiredby big customers. Work OS turns thosedeal blockers into drop-in [music] APIswith a modern developer platform builtspecifically for B2B SAS. Whether you'rea seedstage startup trying to land yourfirst enterprise customer or a unicornexpanding globally, work OS is thefastest path to becoming enterpriseready and unlocking growth. They'reessentially Stripe for enterprisefeatures. Visit workos.com to getstarted or just hit up their Slacksupport where they have real engineersin there who answer [music] yourquestions super fast. Work OS allows youto build like the best with delightfulAPIs, comprehensive docs, and a smoothdeveloper experience. Go to works.com tomake your app enterprise ready. Today,let's talk hagganisms. Essentially,these are nuggets of wisdom and advicethat you find yourself sharing often.You've written a bunch of these about abunch of these online. Um, and so let mejust go through them and then just shareshare kind of the synopsis of the adviceand the lesson around this halaganism.The first is when you have to eat asandwich, don't nibble. Okay, completelystole this from Ruth Porat, the CEO, theCFO of Google. I saw her quotesomewhere. I'm like, that's it. She'sput put a perfect thing on it. And I'llgive you an example where I think thiswill play out over the next coupleyears. I

00:38:44think within the next coupleyearsthere'll be a real retrenchment invaluations and some some will live up tovaluations a lot won't and like if Ilook at the public markets they're verytight right now it's like theanti-bubble I look at private valuationsit's like a real bubble I think there'sa reckoning somewhere down the road anda lot of companies are going to have todo layoffs a lotit's never fun it's usually the worstthing in the history of your life andthe temptation is to do well just do alittle one now and we'll grow into itand then do another and then they doanother one in six months and thenanother one. I think with everythingincluding this type of thing is just ripthe darn band-aid off. Tell everyone thebad news. They're adults. They canhandle it and get it done. Um and Ithink people avoid that. I I thinkthat's good advice Ruth Ruth Porat'sgiving because you're going to have badnews to deliver. Bad shit's going tohappen to your company. Even if it lookslike it's going amazing right now,you're gonnaweird stuff's going to happen and you'regonna have to deal with it. And and wehad a lot of weird stuff happen at HubHubSpot and[sighs]and there there's a basketball coachnamed uh Mike Shashesky.

00:39:59He's Duke's basketball coach, all-timewinningest college basketball coachever. If you go to a Duke basketballgame, [snorts] you can hear him yellingfrom the si sidelines, "Let's play.Let's play. And what's going on there iswhen a college basketball playeris playing in the game and takes a shotand clanks it off the rim and misses it,they have a strong tendency to go playoverly aggressively on defense in theback court and many times compound theirerror by making a foul or something likethat. And what he wants to do is peopleto make their error, forget about it,and move back down the other side of thecourt and run the play. And so we usedwe actually there were times inHubSpot's history where we had the MikeShasheesky's face on a huge slide infront of the company meeting saying nextplay because there was an unforced errorand we need to deal with it and kind ofmove on.>> Is there a story of that that comes tomind that is uh interesting and worthgetting into? There's a lot of them, butI remember in 2000, it was the end, itwas the last day of March in 2019,andwe had a really bad outage like all day.And we never really had one of those.And

00:41:15umit was bad. Customers were unhappy. Alot of customers canled. I had a lot ofcustomers yelling at me. And I rememberthat company meeting. I cried in frontof the whole company. He couldn'tbelieve it happened to us. And Iremember using the next the next playum slide on that one. Um yeah,>> most of we made a lot of mistakes atHubSpot. A lot of bad things happen tocompanies and most of them areself-inflicted>> and a lot of them are the old the oldsaw likecompanies are far more likely to die ofof of overeating than indigestion.Usually it was trying to do too much. Ihaven't heard that version. I've alwaysheard most companies die of suicideversus homicide.Indigest too. [laughter]>> Oh man. Um, okay. So, uh, nexthagganism. Uh, never waste a goodcrisis. This something that people hear.I'm curious just just kind of likewhat's the what's the lesson here? Andthen is there an example of this thatwhere you learned those lessons? I'lljust follow on to most of the goodthings that happened at housewife cameout of a crisis because we would take,you know, pretty drastic measures to fixit and make sure we didn't do the samething again. And so in this particularcase, we

00:42:30really rethought how wedeployed software, how we thought aboutmaking softwarein in a way that was incredibly healthy.And I mean, we we haven't had a seriousoutage since. Um the quality is muchbetter. And kind of an interesting thingwith HubSpot is we started as amarketing software company and wepivoted we had Salesforce kind of cameinto our market we pivoted into CRM andone thing that we if if your marketingsoftware goes down like if your workflowif there's a bug in the workflows orsomething like that it's bad but yousurvive it you wait a little bit if yourCRM goes down particularly the last dayof the quarter you're really impactingyour customers ability to do business.So that was like a mindset shift that wehadn't quite come to terms with of howimportant we were to our customers. Andso we made a lot of changes based onthat crisis. You know, good things comeout of you. Usually very good thingscame out of crisis.>> So there's a lesson there. Something'sgoing wrong. Is it just likeovercorrect? Like use this as a way to>> we always overcorrected. Yeah. Swung thewe almost we purposely swung thependulum hard the other way. M whichconnects to the first uh halaganism ofuh if you're eating a sandwich,don't nibble. Just it's almost like goall the way, go even

00:43:45further.>> Yes. Make it really obvious to everyonewhat's going on.>> Okay. Another hagganism. If you want tokill a plant, have two people water it.>> I love this one. It's very true. Let'ssay, Lenny, you bought a new beautifulplant for your office and then you wentaway for a month to Turks and Caosbecause your AI agents doing yourpodcast and you asked two of yourfriends, hey, can you would you mindwatering my plant and there's one of twooutcomes would happen to the plant. Theplant would either be over watered anddie or not watered at all and die. Andevery CEO in the adults table has gonethrough this and they are religiousabout the DRRI. Like everyone talksabout DRRi in the in the kids table, butonce it gets to the adults table, likepeople get deep religion on it. And andI think it makes sense like when you'resmall and you're in startup mode,everyone's in the room, everyone knowsexactly what's going on. So let's sayyou're running a pilot project with abig account. You're running that pilotproject, everyone's on the same page, asalesperson, a service person,developer, everyone's on the same page,and you go out and do it. You executewell. When you get it scale, you get asales organization, you've got yourforward deploy and engineerorganization, you've got your productmanagement organization, you got somedevelopers working on it.

00:45:00Everyone'skind of separate. No one knows reallywhat's going on in the otherdepartments. And so, let's say you wantto really have a good pilot process. Youwant to rethink it because you'rescaling.Everything important happens crossffunctionally inside a company at scaleand you need someone powerful uh to ownit. Uh, so let's say it's a salesperson.They need the power to like tell peoplein other divisions what to do, even ifthey don't own it. So almost every CEO Ideal with is is like a zealot on theDRRi idea. And it doesn't bite you untilyou get to some sort of scale. And to besuper clear about the advice here, it'sone person is responsible for a goal, ametric, some outcome you want versus uhit may feel like, okay, we have twopeople on this, it'll be awesome,they'll work together. Your advice hereis that doesn't work. Committees neverwork. Yes. Yes. It's in DRRI is directlyresponsible individual.>> The way I always uh thought about thisis just having someone's ass on the linefor something uh makes them so motivatedto get it done versus like spreading,you know, the responsibility and the upand the upside and the downside. It justdoesn't work.>> I totally agree with you.>> Awesome. Okay. Uh another algism, Idon't know if you put it this way, theway I think about it is this idea ofthere's no such thing as a silverbullet. there just it just takes a

00:46:16lotof lead bullets to get something done. Ithink the way you wrote about it is it'salways like one step forward, two stepsback. Talk about your advice there.Yeah, I always thought incorrectly thatwe would have one hire or one investoror one event or one product release thatwould I was wrong about this, but it'dbe a silver bullet and and like thereality inside the HubSpot machine, theway it felt to me, it looks from theoutside like over a long time up and tothe right and smooth, but inside it wastwo steps forward, one step back, twosteps forward, one step back, two stepsforward, one step back. Um, and a lot oftimes it was a crisis that caused thatstep back. Um, so we just didn't havethat. I And the thing about being afounder CEO is there's no one,especially when you're in your 20s,there's no one there to rescue you. Yourparents aren't going to rescue you. YourVC is not going to rescue you. Yourteacher, your thesis advisor, you'rekind of on your own and you got tofigure it out. And that kind of hits youwhen you hit your first crisis. Likeit's on you. You can get some help, butit's on you.>> Sometimes they have you in their cornerif they're lucky at Sequoa. Plug>> I can't oftenimes. I can be the shoulderthey cry on

00:47:31and I can give them advice,but it's still on them.>> Do you feel like too many people startcompanies just like like when someonecomes to you like, "Hey, Brian, should Istart should I start a company of thisidea?" Do you often just like>> No, you don't have no idea what you'regetting into. This is going to be muchmore painful. I heard Jensen Hong saythat like I wouldn't start [laughter]Nvidia if I had it to do over.I that if someone asked me that questionI would start HubSpot over. It was veryhard. Um there were a lot of sacrifices.It wasn't glamorous at alland but in the end of the day I'mincredibly proud of it and you know youknow on my death bed I'm going to lookback and be and really enjoy it. And theDaly Lama's got a good expression likelive a good life so you can live itagain on your deathbed. And I'm reallyglad I did it. But I do talk a lot of flot lot of founders out of it. Like theobsession is real. It's it's you have tobe deeply obsessed. And all these allthese founders and CEOs I talk to, Imean people talk about 996. It's waymore than that. I mean the founders areseven days a week. They're always on. Itext from them on Sunday nights. Um,it's full contact. And I think what'sgoing on there, particularly now,

00:48:46ispeople just see this massive platformchange, massive opportunity. They don'twant to waste the opportunity. So, Ithink that mindset's right. But peopletoday are much moremuch more hardcore than they were in myera. Like, I worked hard. I was probablyI was 60 to 70 week hours a week for theentire time. Never really turned it off,but that's kind of how I thought aboutit. It's different now. People are muchmore focused. And I think Elon'sinspired people like>> I had a starter back in the day andnowhere near as successful as HubSpot.But the way I thought about it is let mejust give it everything I have and seewhat I can do. This is nichot. This ismy chance. Let me just give it all likeforget balance. Just go for it sevendays a week for a while. You know, thenyou scale back. Um and it's just likesuch an empowering thing to do for awhile. Just like let me just try. I'llgive it my this won't be forever.>> Yeah.And I know you've written about thisjust like balance for co is not youshould not have work life balance if youwant to be uh incredibly successful. Idon't know if that's always true butjust what's I don't know how do you talkabout that to founders?>> I don't know any of the founders I workwith that have work life balance. By theway, this is not something I recommend.Um I didn't have it. I don't think myco-founder Dash had it. None of the Cthe only CI

00:50:01C CEO I know and he's he'sunusual in this way is Kareem from Clay.He's like, "Nope, you need balance. Takethe weekends." Like, he's got adifferent mindset. I'm going to have himon my pod to to talk about his mindset,but he's sort of the outlier. Everyoneelse is really really obsessed and theyreally don't have much of a life.>> It did take them a long time to findproduct market fit.We're definitely pre AI. [laughter]>> Wonder if there's a correlation, but itdid work out. So,>> great.>> So, it is a it is a good lesson. Okay.Uh a few more here. One is uh it's amath formula. EV is greater than TV isgreater than me. What is that?>> Okay. EV is enterprise value. TV is yourteam's value. Me is your value. And asHubSpot was scalingand we had a lot of people who were VPsin different roles and they started toget goodsiz organizationswhere they would fall down was theydidn't solve for me but they'd solve forTV over EV. It's all for their own team.So let's say they ran sales.

00:51:16and say Ijust want bookings to be as high aspossible because I get paid on bookingsand the service team can handle all thedownstream problems I created uhmarketing to sales between everydepartment this happened and the kind ofimmature managers who didn't scalereally saw for themselves and sub asthey saw for themselves kind ofsuboptimized for their peers and the andtheir employees would notice it andcomplain about it. Um, it would be finein the short term, but it would show up.And the place it would show up, Lenny,was we did, and I think a lot ofcompanies do this now, but we did aquarterly employee net promoter. We dida quarterly customer net promoter surveyand a quarterly employee one. And wewould we would have people rate it bythe department they're in. And oneinteresting thing about that,so it's like sales and service andengineering, all the differentdepartments. And we had an overall netpromoter score. And then each departmenthad a net promoter score. And let's justtake sales. Sales net promoter score waslike 65, 62, 68, 30. Ooh, that's a bigdrop. And then you read the comments andit was not good. A lot of complaintsabout the leader of that. And a lot ofthe complaints were a little bit of

00:52:31thisTV thing. Um and then we give feedbackto that VP would help them. We give themall the comments be like you got thisand then a quarter later from 30 to negfive. It almost they almost never theynever actually recovered. When you loseyour team you kind of can't it's hard toget them back. Um and that's why I sayyou know higher slow fire fast. And thisdoesn't show up in the first 100 150employees. Everyone's solving for EV,but as it gets bigger and the CEOdoesn't know anyone and there's a couplelayers between you and the employees,they tend to solve for TV. So, we alwaysput on the wall, solve for EV over TVover MV, and then we added CV in frontof EV. Solve for the customers first,then for HubSpot, then the employee,then yourself. Um, that was very helpfulto us.>> Yeah. Uh I imagine everybody listeningworking at a big company understandsthis where you have goals you get yourKPIs and your performance reviews basedon what impact you drive if you hit yourgoals and so you know everyone's theincentives are focus on my goals anddrive those and I don't care about otherpeople's goals the company's goals SteveSteve Jobs had an interesting line hesays you don't work for your boss youwork for Apple

00:53:46>> I thought that was pretty good andthat's I I heard that after I was CEO ofHubSpot but that kind of captures thesentiment And that's how I felt aboutHubSpot. You work for HubSpot first andthen you work for your boss.>> This is hard because you know people'sperformance reviews are based on theirgoals, KPIs. It's always like here'swhat I got to drive. Uh other thanputting posters on the wall and this isour just HubSpotgrowth above all is what matters orcustomers I guess in your case. Is thereanything tactically that was useful inhelping people prioritize enterprisevalue?>> This was explicitly called out in theform for the employee. You know, whenyou got your review, this was part ofit. And so they get they get a score ofone to I forget 10 on that. I would talkabout it constantly and I when we firststarted HubSpot I ran it a little bitlike Jensen runs Nvidia whereI didn't do one-on ones and I gave a lotof good and bad feedback publicly inlarge management team meetings and Idefinitely would go out of my way tocriticize people if I felt like theywere solving for TV over EV and peoplegot a sense for that. Um, and then everyquarter we did like a really wellprodduced company meeting. We spent alot of time on it and at the end of thecompany meeting we we gave out we calledthem the champagne awards was a bottleof VUV that

00:55:01my co-founder and I signedand would read something nice about themand give it to them and usually therewas an EV team in that and so we diddifferent things to kind of beat thatinto people's heads.>> Amazing. So here is just celebratepeople that focus on this and alsoinclude it in their valuationperformance reviews.>> Yeah.>> Okay. That's a good segue to anotherhagganism where you talk about howcompanies are either customer centric,employee centric or investor centric andit's really important to know which youare and you guys actually shifted there.What's what's your insight there? Okay,we were very employee centric um morethan customer centric in the firstseveral years of HubSpot. So much sothat we the company was number one onglass door's best place to work. I wasthe number one CEO in Glass Door. And asI look back at that, I'm not sure that'sa good thing. Like wanting to be liked,I don't think is a good feature of aCEO. And wanting to be the best place towork probably isn't the right way to go.Like if you look at Toby from Shopify,his scores aren't that good, but thatcompany's doing really, really well. Um,and so we overindexed on it. And part ofthe reason we over indexed on it is ismy co-founder was really strong in this.And we had an incredibly powerful headof HR

00:56:16name, Katie Burke, and we justworked on it. We we spent a lot of timeon it. And when we have a managementteam meeting, and let's say it's fourhours long, like two of the four hourswould be on employee stuff. And at somepointI was like, why are we spending so muchtime on employee net promoter scores?Like let's say our employee net promoterscore was 60 and our customer netpromoter score is like 25. I was like weneed to take I would give up 10 pointsof employee net promoter score to get 10points of of customer net promoterscore. And so over some time we shiftedthe center of gravity to customers. Umand worried we still of course worriedabout employees but the center ofgravity from HubSpot moved very much tocustomers. And we did that in a few wayslike every time we had a management teammeeting. We had our management teammeets once a month not once a week. andwe would have a customer panel come onand that customer panel I would run thepanel and ask very tricky questions tothe customers and pull out the bad newsfrom that and then we we still do thiswe have an employ we have a uh sorry acustomer panel at our board meetings ourwhole board can ask questions and myfavorite question is what do you loveabout HubSpot

00:57:32and then and then what doyou hate about HubSpot and they kind oflook at your shoes and you're like comeon [laughter] and it's a great way so sothe employees voices here those companymeetings, we had the the the customersin the company meetings. We changed thecomp plan. So the management team gotpaid not on revenue but on retention andnet promoter score. And so we workedvery hard and kind of swung the pendulumto customer centric. Uh but I do thinkcompanies have one center of gravity oranother.>> There's a really interesting threadthroughout this conversation of justwhen do you want to change how youoperate? you have to go really far to awhole other and almost overcorrect tolike yeah it's really interesting ofjust how much work it takes to changeculture to change norms>> and the bigger it is the more obviousyou have to make it and and the otherthing about being a CEO Lenny is you gotto say the same thing over and over andover and over and over again it justdoesn't sink into people's heads youhave to just be incredibly repetitive onit before it sinks in same thing withmarketing but internally uh that happensthe other weird thing about being a CEOany is as it gets bigger,[snorts]like when it's small, everyone's givingyou and like you're all on the samelevel, but as it gets bigger, you didn'tinterview everyone. You

00:58:47thousands ofemployees, you don't know everyone andpeople put you on a pedestal that youdon't deserve. And let's say you're inthe hallway and you're just kind ofshooting the with a bunch of peopleand you're like, "Ah, it'd be cool if wehad a product that d somebody inevitablywould go home and build that thing andbe like, Brian wants this. This is a biginitiative. So people really lock in onwhat you say. And it turns out you haveto be very repetitive and you have to bevery careful what you say.>> Dares was on the podcast, your uhillustrious co-founder and he developeda whole system to avoid this sort ofthing. Flash tags or it's like this isjust an FYI. We had a whole systembecause we would say something on anemail to the management team or Slackand everyone be like okay this is whatthey want. Let's do it. And sometimes itis like this is you need to do this andsometimes it is like we should talkabout doing this and sometimes it isthis is just kind of an FYI we'rethinking about it and because it got bigwe came up with that rubric of we neededto tag each email with how do you wantme to get this done this week or is thissomething we should talk about or isthis something that's just FYI I'mthinking about>> it was like like one of them is plea I'mpleading you to do I'm not telling youto do this I'm just pleading that you dowhat I ask. [laughter]Oh man. Okay. I This all this allconnects. And

01:00:02by the way, you guys wereco-founders for 20 years. Um you sharedsomething before we started recording.So Dash famously did not ever wantdirect reports. He's just like, "Brian,I want to start this with you, but I'mnot I don't want to ever manage anyone."And you were talking about how you hadto take on engineering, which didn'tmake any sense.>> Well, I'm an engineer, but I'm and I cancode, but it's not good. And so when westarted the company, he's like, "I was aCEO before. I was terrible at it. I wantto do it again. You're going to be theCEO." I'm like, "Great." [snorts] Andhe's like, "And by the way,I'm not going to have any directreports." I'm like, "Well, it's just thetwo of us, so don't worry about it."He's like, "No, ever. Never." [laughter]I'm like, "Yeah, yeah, yeah." And then,you know, we got 10 12 people and we'restarting to hire engineers and on boardthem and making our big decisions. AndI would go to him and be like, "Well,can you manage them?" He's like, "Don'tyou remember I told you I won't have anydirect reports?" He's like, "Surely youwere kidding when you said that." Hesaid, "Nope." So, Der Sha has never hada single direct report at HubSpot.>> Incredible. I don't It's just like adream a dream a way to operate. Uh Ilove that you made it possible for himand it created all this opportunity forhim to tinker and Yes. And>> it's a free month to really think and becreative.>> Yeah. I'm excited to get him back on thepodcast someday. We're going to link to

01:01:18that episode. Maybe a last question. AndI'm curious if there's anything else youthink we missed. As a as a company growsand scales, the job of a CEO changes.You've written a bit about this of justlike how different the job is whenyou're a starter versus a scaleup. Whatare some of the things that most changewhere your time goes as a CEO as thecompany grows? We clicked on thisearlier, but that inspiration thing,like I have a little rubric where it'slike 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 ina startup, and you still need to be veryattached to it. And you still need totalk to customers. You can't give it up.But man, you have to let go of so muchstuff over time in order for theorganization to scale. And I had a Ihave trust issues. Like I only trusted asmall number of people at HubSpot to bea DRRi to really drive somethingimportant that drove people crazy that Ididn't have a a larger trust surface.Um, every one of the CEOs I work withhas the same problem. And that's athat's a scaling limit. That was a limitfor me. Um, I wasn't trusting enough.

01:02:33>> Brian, I feel like I could uh chat withyou for hours. There's a whole list ofhaggis I'm going to link to that wedidn't even touch on. But before we getto our very exciting lightning round, isthere anything else that you think weshould chat about? Anything you want toleave listeners with?>> I Well, I would say if you're a CEO andyou're interested in scaling, I thinkthe halaganism post is like all themistakes I made in my 15 years beingCEO. I tried to summarize in there. tohelp you avoid them. And I have a pod.You should first listen to Lenny's podbecause it's amazing. But I have a podjust for CEOs called Long Strange Tripwhere I interview I interview CEOs aboutthis. So Lenny's interviewing me aboutbeing a CEO. I get to interview otherpeople about being I'm kind of a CEOgeek these days.>> And the the name of the podcast is theGrateful Dead reference, which wehaven't touched on, but you're a huge>> dead head as they say.>> That could be a whole other podcastconversation. I think there shouldactually because I wrote a book calledMarketing Lessons from the Grateful Deadand there's so much. The Grateful Deadwere like the ultimate Silicon Valleystartup. They started in 1964. Do youknow where they started, Lenny?>> Um, no. PaloAlto.Their early concerts were at Stanford

01:03:48were all over Silicon Valley. They're aSilicon Valley company. They were veryfirst principles in their thinking. Theycreated a new category, a new way todistribute their music. Theydisintermediated the uh the ticketingcompanies, very innovative. Steve Jobsand Jerry Garcia are like very similarin my mind, real craft people. So, Ithink of them as a great Silicon Valleysuccess story.>> Uh you said you had a whole book aboutthis. Uh what what's the book called?Just in case people want to dig in.>> Marketing Lessons from the GratefulDead.>> Amazing. And I read that you boughtJerry Garcia's guitar for a large sum atsome point.>> Yes, I did. And I I consider myself thesteward of his guitar.>> Um it gets played like Dead and Coplayed it. And there's a millionGrateful Dead cover bands that let themplay it, but I I'm taking care of it for[snorts] for the Dead Heads.>> What's like one nugget of wisdom orlesson that people can take away fromThe Grateful Dead for startups?>> Okay, people talk about spiky teams. TheGrateful Dead team was interesting.Garcia himself was a bluegrass guy. Hewas a banjo player. And then Bob Weirrecently passed, was kind of a countrykuner like like country music.

01:05:04Thentheir their bass player was a avancgarjazz trombonist, Phil Leash. And theirum keyboard player was a guy named RamMccernan Pigpen. And he was like aharmonica guy. And the drummer was likea marching band drummer. And so spikiestof spiky teams came together and made anew genre. They created a new categoryof music. It wasn't rock and roll.Wasn't sort of rolling stones. It wasn'tBuddy Holly. It was like this new thing.And then they called it a jam band cuzthey played rock and roll in a bluesyopen organic kind of jazzy way. And sospiky teams in creating categoriesunderrated. Incredible. Are you one ofthese people that have been to like a100 Grateful Dead concerts? Okay.[laughter]>> Makes sense. Okay. Uh, this could be awhole podcast, but we're going to we'regoing tomove along. Um, okay. With that, we'vereached our very exciting lightninground. Brian, are you ready?>> Let's do this.>> Fired up. I've watched you do the rightlightning round so many times.>> I'm flattered. Unsurprising questions.Uh, what are two or three books that youfind yourself recommending most to otherpeople?>> I haven't read a book in a long time. Ilisten to

01:06:19podcasts. I'm on X. I talkedto a lot of other CEOs. I can't rememberthe last time I actually sat down andread a book.>> Much respect. I had Mark Andrew onrecently and I don't know if you'veheard his whole thing on how what heconsumes. He talks about he has a verybarbell strategy to media. It's uheither Twitter or books that are 10years or older and nothing.>> I've heard him say that. I'm heard himsay that. Uh, yeah. I kind of stoppedreading. I looked at I I was gettingready for this, Lenny, and I was like, Ican't remember the last book I read.>> I think this is going to make a lot ofpeople feel better that don't readbooks. I like, all right, this is okay.Um, favorite recent movie or TV show youreally enjoyed?>> I love the new Ken Burns. Very long,very good Revolutionary War documentary.Um, he's a crafts person. It'sexceptionally well done. And what I likeabout it is America is really like adisruptor startup. Like so many startuplessons from those ear they were gutsy.Talk about two steps forward, one stepback. Like they got into the details ofhow George Washington ran the army.We were very close to losing that warmost of the time. And two steps, twosteps forward, 10 steps back.

01:07:34Two stepsforward, 10 steps back.>> Lots of lead bullets. a lot and like andlike unless we had alliances like we hadalliances with the French, we werescrewed. Uh so I love that that it's along one, but it's really good.>> How long is this? What are we gettinginto?>> Probably 10 plus hours.>> 10 plus hours. What a It's a lot. Uh butuh worth it is what I'm hearing.>> I'm in Boston. You know, it'srevolutionary surrounded by history.>> All right. Uh favorite product yourecently discovered that you reallylove?>> I love my deli clone. I teach a I teacha course uh called scalingentrepreneurial venturesand um I don't do I don't do officehours. I have deli do my office hours.Very happy with that.>> The my favorite feature of deli andagain lennybot.com there's my delithough we both have little bots. Uh thevoice feature is the coolest thing rightjust good great I can't I had video theygot rid of it they're going to bring itback. Can't wait till it has video. Myleast favorite my lowest MPS product ismy Sonos system. You have Sonos?>> I do. And I I get you.>> Yes. Painful.>> Yeah. It's like so good in so many waysand so annoying in so many ways. Soannoying.>> But like we still use it, you know?There's nothing better.>> You're not a competitor. You and Ishould start as someone competitor.>> No, we should not. That's a bad I'm notdoing this.

01:08:49And just to be clear whatthese bots are just so people understandhow cool this is. So my strain on everysingle podcast like this one is going tobe sucked into it and every singlenewsletter and you just talk to it andask it like how do I find product marketfit and it's based on everything I'veever shared. Here's here's your steps.Okay. What's even better about it is isyou because you can go to chatbtd andsay what would Lenny think about this.What it's added is the ability to put abunch of documents in there that aren'ton the internet. like I put my mylectures in there and there's a newfeature where it asks you questions andit kind of interviews you and so it's ait's pretty proprietary. It's it'sgetting better. I like it a lot. Yeah.To that point, the uh I haven't uh uhpromoted this feature of it, but it'strained on all my paid content, too. So,even if you're not a paid subscriber,you get access to all of the things I'veever shared. No, don't not tell let'snot tell too many people that becauseit's one day I'm going to pay wallet inthe near future. Anyway, enough aboutthat. landingbot.com.Do you have a favorite life motto thatyou find yourself coming back to in workor in life?>> This isn't lightning, but four yearsago,I had a very bad snowmobile accident.Drove a snowmobile off a cliff. [snorts]The snowmobile smashed into a millionpieces at the

01:10:04bottom of the cliff. Sodid I.And I laid at the bottom of that clifffor a while.I was unconscious for a long time. wokeup andI didn't think I had my phone. So, I satthere for a long time like I'm probablygoing to die tonight. No one knows whereI am. It's frigid out. It's in Vermontand I'm going to freeze to death. And Isitting there for a couple hours. Ifinally was like, "Oh, I do have myphone." Dialed [snorts] 911. By the way,911, amazing service. And so, thehelicopters came in, took me out, tookme to the hospital, and lots ofsurgeries. And I was kind of out ofcommission for a year. Uh, and you can'tsee it, but I got metal all over me, allin me. Life short, like life short. AndI I made some decisions at the bottom ofthat cliff. The the one of the decisionsI made at the bottom of that cliff was Idon't really like being CEO of an 8,000person company. Doesn't really suit me.Like my harmonic motion is off. I don'tlove the day-to-day. if I make it out ofhere alive,I'm out. And so that's exactly whathappened. Like the first big thing thathappened coming out of that was I gave[snorts] the job to Yam who's still the

01:11:19CEO doing a great job. So life's short.Don't waste it. I've heard the story,but it's just as powerful hearing itagain. What um why do you think it takespeople why does it take a moment likethat to help have someone realize thisis I need a change, you know, or justlike>> I think people think they're going tolive forever andthey're not. Um as somebody who's 58,yeah, life's very short and I'm muchmore intentional about the decisions Imake, much more intentional about thepeople I hang out with today than I wasbefore that. And I really try to work onthings that bring me joy,>> like this pot.>> Same. I I appreciate it.>> Same. Um I read that you had 20 brokenbones in this accident.>> Lot of broken bones. A lot of metal.>> I got 33 screws in me. One loose one uphere. Lenny.>> Same. [laughter]Okay. Uh last question. We talked a bitabout the Red Sox. You're a part ownerof the Boston Red Sox. Now, what'ssomething that would surprise peopleabout how a baseball team is run or justwhat it's like on the inside of a teamlike the Red Sox?>> It's not as profitable as people think.People think like these rich guys comein and buy these teams, but the way theleague is set up and the

01:12:35way theeconomics are set up,it's not it's not a profitable endeavor.Whereas like other leagues are much muchmore profitable. Um, baseball's alsoalso deeply flawed. It doesn't have asalary cap. And so you've got theDodgers, who I take my hat off to, havelike a $400 million payroll, and theMiami Marlins are like a $100 millionpayroll. And in other leagues, that allkind of balances out pretty well.Baseball sort of it's it's set upincorrectly. I think it'll correct uh inthe next couple years, but um it's kindof it's a broken model.>> Intriguing. Uh, stay in AI SAS if youwant to make money is what I'm hearing.Vertical SAS. Uh, Brian, this wasincredible. Uh, covered almosteverything I was hoping to cover. Uh,two final questions. Where can folksfind you online if they want to reachout? Where do they find the bot? Wheredo they how do they work with you ifthey wanted to or do they have to be aSquway founder? Uh, and then how canlisteners be useful to you?>> I think there's two things. I would lovefolks to listen to long strange trip mypod and I would I get some comments butnot a ton. Like Lenny, you have morecomments than yours. I'm jealous. I'dlike just feedback on how I'm doing.Like it's very new and it just started

01:13:50acouple months ago. It seemed like it'sgoing pretty well, but like it's myfamily and Sequoia people giving mefeedback. I'd like to see how all of youwhat you think about it. So that wouldbe spectacular.>> All right. So hop on your YouTube andleave some comments about what theythink. The real real honest faith.>> Okay, here it comes. Uh Brian, thank youso much for doing this.>> Appreciate you. Appreciate you. Thankyou. Bye everyone. Thank you so much forlistening. If you found this valuable,you can subscribe to the show on ApplePodcast, Spotify, or your favoritepodcast app. Also, please considergiving us a rating or leaving a reviewas that really helps other listenersfind the podcast. You can find all pastepisodes or learn more about the show atlennispodcast.com.See you in the next episode.