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

0:00 The thing about being a founder, CEO is there's no one there to rescue you. Your parents aren't gonna rescue you, your BC's not gonna rescue you. That kinda 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 the 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 nine. It's way more than that. 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.

1:01 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.

1:26 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 error, 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.

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3:49 Request a demo at datadog hq dot com slash lenny. That's datadog hq dot com slash lenny. Brian, thank you so much for being here and welcome to the podcast. Thanks me, Lenny. It's my pleasure. I wanna start with something that I've heard your board members the way they described you.

4:10 Is uh someone with a perpetual state of constructive dissatisfaction. Do you think this is a core foundational kind of uh trait of successful COs, successful leaders? By the way, I like that description. I uh when she the uh woman named Lori Noring Norrington, who's the subsequent chair said that I like it. I took it as kind of a compliment. Um And I I and I liked it. And as I so I spend most of my time these days coaching

4:36 Very fast growth CEOs. They all are kinda 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

4:55 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. Ін I've been surprised at how humble. this generation is of CEOs. And I think of my generation of CEOs as being

5:14 I don't know, I wouldn't s 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 It's 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 CO of an incredibly successful company for a long time for about twenty years before you move on to this new chapter.

5:35 Now you work with a bunch of COs. You're the you're Sequois in house CO coach. There's a few things that I've heard you do. What is you gather groups of COs And uh what I've read is that you have kind of

5:48 Two tables. You have the kids' table and the adults' table. They could stable SOs that are. companies that are about under a hundred employees, the adult table is over a hundred employees. Uh so let me ask you just When you look at COs that move from

6:01 It gets table to the adult table, other than just, you know, they scale and and grow. What is it that these COs that graduate from kids to adults table Uh do differently. The adults are are really focused on

6:15 And all they really want to talk about is their exact team. They're director ports, 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

6:31 half their time just recruiting and interviewing. It's pretty all consuming. And I remember that from that phase and up spots growth. And it surprises people like wow, my job is really just to interview and hire. I didn't know that was gonna be the case. Um, so that is one that they kind of are Making that transition and and I would just say in general

6:53 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?

7:07 In underrates A really high quality blind reference. And I interviewed Uh Dave The CEO from

7:18 MongoDB the other day. And he had an interesting stat on average over his like ten year lifespan As a CEO of MongoDo. There were two C level Two C levels turned over per year.

7:31 That's a lot of turnover at the top. And I didn't keep track of it like Dave, but I'm Think HubSpot was kinda similar. In all of these startups Are kinda similar to

7:43 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?

7:56 What advice do you give'em to help them develop that skill? I think even me, I've been doing this for a hundred and fifty years, I still think I overrated 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

8:17 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

8:34 And if they're just very complimentary and it's so great and you're doing this gr 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.

8:52 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

9:16 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 ten, 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.

9:40 on those blind references, I think, are Is really good. My other piece of advice, and no one listens to me on this, is hi uh is hire slow and fire fast. Um People hire fast and fire slow. Oh.

9:55 And if I had to guess Lenny. With eighteen months after you hire a C level exec, At least fifty percent of the time they're gone. There's just I mortality rate on them. It's it's harder than people think.

10:10 And what so what you're saying here is there's only so much you can actually do to Increase those odds. I think you can. I I I think you can you can um I think the blind references are key. I think doing like real interactive working on a project together.

10:25 I'll tell you one other thing we learned at HubSpot about this. Like we would have a candidate come in, let's say uh head of engineering. It would have like eight people interview them. And our scale's one one to four. And let's say four people were four out of four.

10:40 And four people were two out of four. So that's Canada A. And then the next candidate comes in, eight people interview them, and everyone's a three I'm four. Almost every time we hired the three out of four. Like the person with the least amount of weaknesses. And we changed it and we we went with the spikier people. We went with people with weaknesses. We went with people with challenge stuff.

11:02 And that has worked out quite well. Like our hit rate and hub spots improved. We also have shrunk the the the pool of people on that interview panel from eight to like four. Like we just hired a ahead of product and there were just four of us that interviewed him. I think that worked too. Um, so I think there's things you can do to get better at it, for sure.

11:21 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?

11:35 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.

11:47 Go ahead. 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 ten, how likely are you to hire them again? Stuff like that that kinda gets at the core or

12:02 Were they the top one percent of your employees? That's a good question. Oh. Were the top ten. 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 go up. I tell you the other mistake everyone makes.

12:20 I made and all all the CEOs were making now. Is You're hiring for the whatever, head of engineering. And you're blown away by the resume. Like you're fifty employees and you're hiring this person. who's been at Microsoft the last ten years and is a fancy title

12:36 Yeah, 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 get your shit together. It's just you don't. You definitely don't. Uh if you're fifty or five hundred employees and they expect you to have your act together.

12:58 And so that is another Like avoid the big company hire. Like we hired so many people from Salesforce and Google, Microsoft. Like a hundred percent. 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

13:15 A cohort comes in and we think that's gonna 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.

13:26 It never works. Like by definition, they would fail on my spectrum of like Most founders are like me, like they are skeptical of dimensional wisdom. They're unhappy with the w world works in some way. And so they're kind of far on that spectrum of of rethinking conventional wisdom. And almost by definition, somebody who goes to work for McKinsey is very conservative in their own. Um so I think that almost always fails.

13:50 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 two thousand four Red Sox. What does this mean? And then well.

14:04 I'm a big sports fan, a big Boston Red Sox and the Boston Red Sox hadn't won any world series In eighty six years since they trained the internet. And they finally Broke they finally won it in two thousand and four. And the way they won it was they had a team of a bunch of home grown

14:21 really high quality Inexpensive talent that they Drafted and came through the farm system. And then they got a few free agents like David Ortiz that a lot of people have heard of that they paid a fair amount of money to. Peter Martinez P Peter Martinez

14:35 And Kurt Schilling were kind of the canonical older Ben that and they're done that bigger company folks and they mixed really nicely. The culture really worked. And I think that's the key. I think people underrated Their home grown talent. Like almost across the board they underrated. And I think you want that mix. You don't want to hire a whole bunch of men that have done that. You don't want to hire none of them.

14:57 I don't I imagine this is public, but you're now a part owner of the Red Sox, is that 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

15:20 uh rising to the occasion. Yeah, if you look at HubSpot, like half the management team Or folks that have been there. For approximately one hundred and fifty years. Which I like. And same with like you look at Apple, a lot of those people are home grown.

15:32 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 home grown in their VP for that C level job. versus hiring someone from the outside. I 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 wards. It's hard to figure out their wards unless you're very good at Line referencing.

15:55 So you tend to overrate them and underrate your homegrown. So if it's pretty close, I think you give your home grown a shot at it. Uh what's interesting to me, Lenny, is you know, the Brian Chesky sort of rethought a lot of this stuff. And He's like everyone's over rate. over rotating to the home grown to the um

16:15 you know, experienced talent and management teams and delegation. I mean, if 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. Actually quite different than what Brian's espousing. Going back to the conversation around COs

16:35 A lot of people listening to this podcast, just a lot of people in the world want to be founders. They want to be COs. At the same time. You look at Elon, you look at Jensen, you look at Steve Jobs, you look at you. 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.

16:51 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 square and meet all these CEOs coming in. And I have a little

17:07 R like algorithm in my head. And I look for four things. I call it my lock. algorithm. L is for lovable. And

17:19 You know, Steve Jobs you would say is Kinda rough and maybe not lovable. But he would inspire followership. You would want to follow him. And so Could I envision a

17:29 Twenty eight year old me graduating from business school going to work for this person. When I crawl across broken glass. That's question one. Two is just obsession. Are they deeply obsessed with this problem? Did they I I'm a little negative on people who came up with this problem to solve six months ago and started a company. I like people with deep founder market fit. Who've been thinking about him for a long time and have evidence in their lives of going deep down obsessively down a rabbit hole. Because that's kinda what it takes to be a founder CEO.

18:02 The C is something I wouldn't have thought of, but this is a Sequoia thing, like chip on the shoulder. Pretty much all of them have a bit be like a boulder on their shoulder. And I I have a bit of a chip on my shoulder too. And the K is just for Deeply knowledgeable about the domain.

18:19 And so I kinda look for Bad. Um If I were to stick an S on it.

18:25 I would say student. Like I look at Winston Weinberg from um Harvey or James from Profound or Gabe from Rogo, some of these new very fast growing companies, they're students of the game.

18:43 They're not just learn it all. They're Deep, deep students of the game. And they're l they're like LLMs. They're constantly, constantly learning. And it's not just learning stuff from me and their peers, but they go way back in time and have a lot of history on stuff.

18:58 So those are some of the Th that's kind of my little criteria I use when I'm evaluating CEOs. What do you look for, by the way? You've interviewed you've interviewed a ton of folks like me What do you think's in common? Of what successful founders. Oh my God. I wish I had the uh my succinct answer. I would ask I would go to Lennybot.com and be like, What is the common pattern across these folks?

19:19 One that you didn't mention that I think is interesting. I did some research on this recently with uh Terrence Rohan. When it's just extremely ambitious. Just trying to do something really wild that most people are like, That's like crazy. You're not gonna like get a subscription service for all music in the world, that's just what you do and do it and you're gonna go through that. It and like is it learnable? I noticed some of the a lot of the CEOs struggling with a couple of things. Like let's say you're

19:45 Your Winston, your late twenties. You've never managed a teen We're probably never even captain of the sports team before. And In order to scale, like you have to give people feedback like constantly.

19:59 Yeah, it's very unnatural to like I'm gonna give this a 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.

20:12 Uh that's something I think They have to learn. They all have to learn to get a good bullshit detector. They're constantly being spun. Everyone's trying to sell to them. The org is always trying to sell to them. So that's sort of something they have to develop.

20:27 Yeah, 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 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 kinda learn on that startup to scale up path.

20:48 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 COs, is this for like investing as a Okay. helping Sequoia decide should we invest in this company.

21:05 What you look for is uh lock so uh I like the yes, I'm gonna include it there. So are they lovable? Are they inspiring? Uh Oh, are they obsessed with this problem they're going after? Uh do they have a chip on their shoulder?

21:17 Are they extremely knowledgeable about the problem they're going out? 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.

21:30 the s uh the being a founder, being a CO. Okay. So I guess going back just to the question, do you think Just to put it very simply, do you think COs are are born or do you think they're made? Can anyone Turn into an amazing C.

21:44 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 Erin Squid's portfolio.

21:59 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?

22:08 Can they catch a ball, can they throw the ball? And they they rate'em 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 kinda new now are there are five tool CEOs.

22:22 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.

22:32 China's super CEO and there's a bunch of them now. And I don't know. I didn't see a lot of those. That's that certainly wasn't Steve Jobs. He wasn't writing pro he wasn't programming Um It wasn't Jump Bezos.

22:46 Uh You know, I think there's kind of a new breed that's quite impressive. These folks you mentioned, uh were this good before AI became a thing. I imagine AI helps more COs

22:56 Fill the gaps that they have. I think yeah, it's har it's hard to fill the gap. Um You know, this guy's a developer, he's Brilliant genius level obsessive. But can he convince can he sell?

23:09 Can you 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 you convince some big skeptical Fortune five hundred enterprise to buy his product like

23:25 Do be 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 kinda code.

23:38 All of a sudden we're gonna be able to build stuff. I think it kinda goes the other way. I love this list you shared of things that you find COs most have to learn. Uh BS detection. uh inspiring people, giving hard feedback. What's maybe like the one thing that most often people that become COS founders have to work on? Is there like a most common thread of like here's the thing you probably need to work on most.

24:00 It's that feedback thing. Wait, 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 kinda step aside. and be the CTO and the thinker and the labs person and I need to hire

24:19 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.

24:34 Mm-hmm. hire ten 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. Yeah, those types of conversations are very tricky and quite unnatural for Homo sapiens to have. If you're

24:54 You know, you're twenty five and you've never done anything like that before. So I see the best ones getting really good at that and studying it. It and it's it's super uncomfortable, but they have to kinda suck it up and get good at it. What do you find most helps them build these skills, get better at this? Is there some kind of tidbits of advice you give them? Is it something that they study to Improve. I I think misery loves company on this, so what I do Like the kids table is fifteen CEOs of companies under a hundred employees.

25:22 And the adults table are COs of companies, over a hundred employees, about fifteen 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.

25:40 I so essentially it's find peers to talk to and share and be more. And the reason I break it out is like the problems with the kids table are very different than the problems at the adult table. Um And in all they all rhyme they rhyme a lot. Mm. 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

26:03 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, h has it ever been easier to start a company? It's absolutely true. And the flip side of that is

26:21 I mean how many companies is m the the the the number of companies formed is going to mushroom over the next ten years relative to the last ten years in the the last ten years pretty Compared to the previous ten years is much. I just think in my life like I'm old. And when I was a kid, I'd walked into C V S corn drug store and I want to buy a toothbr toothbrush.

26:43 There are four or five there. You pick one. And You know, in the night in like the nineties or two thousand, you go to Amazon, there are four or five thousand toothbrushes. Four or five thousand companies great in those toothbrushes. It got much, much easier to make stuff.

26:58 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 two thousand six. But now it's gonna be a even bigger job. So it's easier to start. Now there's so much noise in in con 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.

27:22 And a big part of this is is distribution, essentially breaking through the noise is what I mean. It is hard to learn that. You didn't grow up doing distribution. You don't know. So they'll they're all learning it. Um and the ones that learn fast. It's like a learning game, the faster you learn.

27:37 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 sh said that uh sales Is

27:48 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?

28:00 Let's say inside a hotspot, software development's working incredibly well. Uh customer support. Incredibly well. Um legal. Start to work incredibly well.

28:12 But there really aren't apps like in the rest of the org that have really changed things a lot. And then the go to market side's been kinda slow. uh really just support. Like there isn't like a canonical marketing or sales or

28:26 Maybe the BDR is the first one. But I think ye old enterprise sales where there's actual trust built up between two carbon based life forms, I think will be very, very, very late to go in the white collar world. I also I think a lot about the go to market. I think the gutter market's gonna get turned on its head like

28:48 When I we started HubSpot. If I think of the way the funnel. You wanna 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.

29:03 And I think it's gonna get turned on its head where people Or evaluating a product. They start in Gemini or they start in Anthropic, or they start in Chat G P T. And Yeah, for example, Chat Chipotine knows way a bunch of your

29:15 He knows everything on your website, everything beyond that, knows all your competitors. So they they will stay in there and do lots more research and be incredibly well educated. So your website's a lot less important. And they go to your site. I think sites will change where you're going to have a really high quality avatar. that knows everything about your products, knows everything about your company and your pricing and packaging. And you can have a high quality conversation with that person.

29:40 That person that will get stored in your CRM in in will get um you know, score this is 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 SC. 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. The Zavatar just understands. So this is uh the buyer has their own little agent.

30:08 That comes with them or On HubSpot, you have this avatar that walks you through the sales process. I think both. I think me as a knowledge worker Like what I really want as a homeless APN is I have like a Delphi clone that I really like. Same. It's actually quite good.

30:28 Yeah, yeah. Yeah, where's where do people find yours? Uh they find it on my footer, they can find it on Delphi. We'll link to it. Yeah. And

30:38 What I want is like connect that That thing to my E nail into my granola, into my plod, in It knows everything about me. And then when I go to a meeting Lenny, I want to invite I wanna invite that thing to my meeting. So it's sitting there in the Zoom meeting.

30:53 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. And

31:04 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 trap's on Zoom,

31:20 They have their S E avatar that's kind of all annoying. 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

31:35 Just not. Relaxing on a month long vacation, sending our avatars to all the ease. Go buy me some hub subspot seats, please. Uh. I think this is why Cloud Bob was so popular. I think this is essentially what they're building is this idea, which is now called MoldBot, which might be changing again.

31:53 Uh It's just like this personal agent that can go do stuff for you. Totally. So you're talking about the future of go to market. is this world where there's these little bots and agents that are doing things for you both on both sides.

32:05 When you look at companies today that you work with that are doing well That are Especially AI driven companies. What are they doing different? in terms of go to market that is working really well.

32:15 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 scene. I thought it would be totally different in AI and work with all these companies.

32:31 They're hiring like all the same folks running the same enterprise sales processes. So it hasn't changed that much, at least on the enterprise side. It actually hasn't shi I spent the first ten years of my career at a company called PTC. It's like an enterprise sales machine. Enterprise sales hasn't changed that much since the nineteen nineties. Okay. And so for a deployed engineer, uh very hot term.

32:52 Uh the idea there is they come work with the the cust 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 plugging play. You can't you can't just like set up some agent that figures everything out. Takes a lot of onboarding and integration. Is it actually a different thing at all? Other versus like sales engineering in the past, things like that. Solutions consultant, sales engineer, 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

33:22 I th well, anyway, I think the term is fine. I 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

33:37 having your employees help the customer on board to be successful integrate all that stuff. I think the thing that will change first is the top of the funnel around getting bound in Set of Google you gotta get found in in in these Yeah, A E L. Yeah, that's gonna be really important in the way you build your website is very different for that to optimize for it.

33:57 Um And then your I think your home page is totally different. I think you land on an avatar and have our conversation with them versus you're going through all the pages on your site. I I think the top of the funnel's about to change a lot. Hm. Has anyone doing this well yet? This idea of this avatar or is this just kind of a in the two star program. Hubbutt does it. We built we built one. It's working. Okay. Okay.

34:19 Um, let me ask one more question around CO stuff and then I wanna move on to halogenisms. Alright. How is just being a CO different than it was. So you've been doing this for twenty ish years. Yeah.

34:34 What's like most different about what it was like to be a CO maybe ten, twenty years ago versus today? When I see yeah, as I've 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 the stuff, everyone's more productive, the software developers 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.

35:03 As 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. 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 Open AI and ChatGPT and its consumer app is doing incredible.

35:28 And they're doing lots and lots and lots and lots of other things, and then Gemini comes out. And they've kind of focused back on The core. Uh I think there's a lot of competition, everything's moving fast. I I do think people get more done.

35:41 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

36:00 Like 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.

36:15 And You know, maybe every year I would sit down and I'd And open that one way door or close it. And it just freed everyone up and we just started moving so much faster. I think people need to be making those decisions and walking through those doors. much more quickly than they used to I think that's new and different different

36:35 I was someone who always valued optionality. I think there's a massive tax and optionality when you can move this fast and try a lot of things. So I do think the job's changing a lot. Yeah, and there's so many reasons this is happening. One is just Technology is just Like every week there's a new

36:51 Shift in what is possible. Yeah. Just like What a waste of time it ends up being'cause so much is changing and I know. Yeah, it's hard to keep up. I have to do it.

37:03 Luckily we got some sweet podcasts to check out. Uh 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, Vercelle, Platt, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, skim, barback, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed stage startup trying to land your first enterprise customer, or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready and unlocking growth.

37:48 They're essentially stripe for enterprise features. Visit WorkOS.com to get started, or just hit up their Slack support where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best, with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workOS dot 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

38:23 This halogenism. The first Is When you have to eat a shit sandwich. Don't nibble.

38:29 Okay, completely stole this from Ruth Porat, the CEO uh CFO of Google. I saw her quote somewhere, I'm like, That's it. She's put put a perfect thing on it. And I'll give you an example where I think this will play out over the next couple of years. I think Within the next couple years. There'll be a real retrenchment in valuations and some some will live up to valuations a lot more.

38:53 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.

39:11 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 in

39:31 I think people avoid that. I I think that's good advice, Ruth. Good poor, it'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 get it?

39:43 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 HubSpot and Yeah. And there's there's a basketball coach named uh

39:57 My 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.

40:10 Let's play! Let's play. And what's going on there is when a college basketball player Is playing in the game and takes a shot. And clank it off the rim and misses it.

40:23 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 cour side of the court and run the play.

40:40 And so We used we actually there were times in HubSpot's history where we had the Mike Sheshevsky's face on a huge slide in front of 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 a story of that that comes to mind that is uh interesting and worth getting into?

40:59 There's a lot of'em, but I remember in two thousand it was the end it was the last day of March in two thousand nineteen. And We had a really bad outage, like All day. And we never really had one of those.

41:14 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. We couldn't believe it happened to us. And I remember using the next the next play.

41:32 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

41:41 Most of them are self like that. And a lot of them are the old the old saw like uh companies are far more likely to die of of of overeating the indigestion. Usually it was when we were trying to do too much. I haven't heard that version. I've always heard

41:55 Most companies die of suicide versus homicide. Oh man. Um okay, so uh next halogenism. Uh never waste a good crisis. It's something that people hear

42:09 I'm curious just w just kind of like what's the what's the lesson here and then is there an example of this with that uh that where you learn this lesson. I'll just follow on to most of the good things that happened in Husband 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 in a way that was incredibly healthy and

42:39 I mean we ne we haven't had a serious outage since Um the quality is much better. And it kinda kind of an interesting thing with HubSpot is we started as a marketing software company. And we pivoted We had Saleforce kinda came into our market. We pivoted into CRM. And

42:55 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.

43:14 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 yeah. Good things come out of crisis us usually very good things come out of crises. So there's the lesson there, something's going wrong.

43:29 Is it just like overcorrect? Like use this as a way to always overcredi. Yeah, swung them we almost we uh purposely swung the pendulum hard the other way. Mm. Which can Connects to the first uh halogenism of

43:41 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. Mm. Okay. Another algorithm, if you want to kill a plant, have two people water it. But I love this one. It's very true. Let's say, Lenny, you bought a new beautiful plant for your office.

44:01 And then you went away for a month to Turks and Caicos because your AI agents doing your podcast. And you ask two of your friends, Hey, can you Would you mind? Watering my plant. And there's one of two outcomes when it happened to the planet.

44:14 The plant would either be overwatered and die or not watered at all and die. In every CEO In the adults table has gone through this in they are religious about the D R I like.

44:26 Everyone talks about D R I 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

44:42 A pilot project with a big account. You run that pilot project, everyone's on the same page, salesperson, service person, developer, everyone's on the same page. And you won't do it yes, you will both. When you get it scale, you get a sales organization, you get your four deployed engineer organization. You've got your product management organization, you've got some developers working on it.

45:00 Everyone's kinda 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.

45:17 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.

45:31 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.

45:47 Committees never work. Yes. Yeah. Yes. It's in DRI's directly responsible individual. Mm-hmm. The way I always uh thought about this is just having someone's ass on the line for something. Uh

45:58 makes them so motivated to get it done versus like spreading, you know, the responsibility and the up and the 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 it just takes a lot of lead bullets to get something done.

46:18 I think the way you wrote about it is it's always like one step. Forward, two steps back. Talk about your voice there. Yeah, I always thought incorrectly that we would have one hire or one investor or one event or One product release that

46:33 would uh I was wrong about this, but it'd be a silver bullet in in like the reality inside the Up spot machine, the way it felt to me. It looks from the outside like Over A long time up and to the right.

46:46 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 in A lot of times it was a crisis that caused that step back. Um so We just didn't have that I in

47:02 The thing about being a founder CEO is is no one Especially if you're you're in your twenties, no one there to rescue you. Your parents aren't gonna rescue you, your VC's not gonna rescue you. Your teacher. your thesis advisor, you're kinda on your own and you gotta figure it out. And

47:18 That kinda 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 at Sequoia. Uh huh. I can solve it oftentimes. I can be the shoulder they cry on and I can give them advice, but it's still on them.

47:33 Do you feel like too many people? start companies just like like when someone comes to you like, Hey Brian, should I start should I start company on this idea? Do you often just like No. You don't have no idea what you're getting into. This is gonna be much more painful. I heard Jensen Wong say that, like I wouldn't start NVIDIA if I had it to do over. I

47:51 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. And all

48:03 Yeah, but in the end of the day I'm incredibly proud of it. And You know, I'm you know, on my deathbed I can look back and be and really enjoy it and 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.

48:17 But I do talk. A lot of fat a lot of fanners out of it. Like The obsession is real. It's It's you have to be deeply obsessed in all these All these founders

48:29 And CEOs I talked to. I mean pop people talking about nine nine six. It's way more than that. Yeah, I mean the founders are seven days a week. They're always on.

48:39 I text from Sunday nights. Um It's full contact in I think what's going on there, particularly now, is people just see this massive platform change, massive opportunity. They don't wanna waste the opportunity. So I think that mindset's right. But people today are much more

48:55 much more hardcore than they were in my era. Like I worked hard. I was probab my was sixty to seventy week hours a week. the entire time. Never really turned it off, but that's kinda 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

49:14 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. Scale back. Um And and it's just like such an empowering thing to do for a while. Just like let me just try. I'll give him my bet. This won't be forever.

49:33 Yeah. And I know you've written about this just like a balance for CO is not you should not have worry like balance. If you Want to be Uh incredibly successful.

49:44 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 like balance. Th by the way, this is not something I recommend. Um I didn't have it.

49:57 I don't think my co founder Darmesh had it. None of the C the only CI CEO I know And he's he's unusual in this way is Karim 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 part to to Talk about his mindset.

50:14 But he's sort of outlier everyone else's 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 wonder if there's a correlation. But it did work out. So we're great.

50:32 So it is a it is a good lesson. Okay, uh a few more here. One is uh it's a math formula. E V is greater than T V is greater than M E V. What is that?

50:43 Okay. E V is enterprise value, T V is your team's value, M V is your value. And As Hud Fought with scaling. And we had

50:56 A lot of people Who were VPs. in different roles and they started to get good size organizations. Where do they would fall down? was

51:07 They didn't solve for me V. But it's all for T V over E V. 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.

51:20 And the service team can handle all the downstream problems I created. Uh Marketing to sales I between every department this happened. And the kind of immature managers who didn't scale really saw for themselves and sub as they saw for themselves kind of sub optimized for their peers. And the emplo and their employees would notice it and complain about it.

51:41 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 promoted survey and a quarterly

51:55 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.

52:07 And we had an overall Net promoter score and then each department had a net promoter score in Let's just take sales. Sales net promoter score was like sixty five, sixty two, sixty eight. Thirty.

52:20 Mm. That's a big draw. And then you read the comments and it was Not good, and a lot of complaints about the leader of that. And a lot of the complaints were a little bit of this T V thing.

52:33 Um And then we give feedback to that V P Would help them. We give them all the comments, be like You got this. And then a quarter later.

52:42 From thirty to negative five. It almost they almost never they never actually recovered. You lose your team, you kinda can't It's hard to get them back. Um

52:52 And that's why I say You know, hire slow, fire fast. And this doesn't show up in the first hundred, hundred fifty employees. Everyone's solving for EV, but it as it gets bigger. And the CO doesn't know anyone and there's a couple of layers between you and the employees. They tend to solve for T V, so we always put On the wall, soft for E V

53:12 over T V over Mee and then we added C V in front of E V solve for the customers first. Then perhaps but then the employee than yourself. Um that was very helpful to us.

53:22 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

53:38 I don't care about other people's goals, the company's uh 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 Mobspot, but That kinda 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

53:58 Performance reviews are based on their goals, KPIs, it's always like here's what I gotta drive. Uh other than putting posters on the wall, misses our just pop spot. 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 route you know, when you got your review, this was part of it. So they get

54:21 They get a score of one to them. I forget ten on that. I would talk about it constantly in I when we first started HubSpot. I ran it a little bit like Jensen runs NVIDIA where I didn't do one on ones and I gave a lot of

54:36 And I definitely would Go out of my way. To criticize people if I felt like they were solving for T V over E V. And people got a sense for that. Um, and then every quarter we did like a really well produced company meeting.

54:54 We spent a lot of time on it. And at the end of the company meeting we we gave out we call them the champagne awards, was uh bottle of oo 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 E V 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

55:14 Focus on this. And also included in their Valuation performance reviews. Yeah. Okay.

55:20 That's a good segue to another halogenism. Where you talk about how Companies are either Customer centric. Employee centric or investor centric.

55:30 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. W so much so that we the company was number one on Glassdoor's best place to work. I was the number one CO in Glassdoor. As I look back at that.

55:50 I'm not sure that's a good thing, like Wanting to be liked I don't think is a good Feature of a CEO. And wanting to be the best place to work probably isn't the right way to go. Like if you look at Toby from Shopify.

56:03 His scores aren't that good, but that company's doing really, really well. Um And so we overindexed on it. And part of the reason we over indexed on it is is my co-founder was really strong in this, and we had an incredibly powerful and an HR named Katie Burke. And

56:19 We just worked on it. We we spent a lot of time on it. And when we'd have a management team meeting And let's say it's four hours long, like two of the four hours would be on employee stuff. And at some point I was like, why are we spending so much time on employee net promoter scores? Like, let's say our employee net promoter score was sixty. And our customer net promoter score is like twenty five.

56:42 I was like We mean to take W I would give up ten points of employing that promoter score to get ten points of of customer net promoter score. And so over

56:53 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 Hudson was very much to customers. And We did that in a few ways. Like every time we had a management team meeting

57:09 We had our management team meetings once a month, not once a week. And we would have a customer panel come on. in that customer panel, I would run the panel and ask very tricky questions to the customers and Pull out the bad news from that. And then we we still do this. We have an emplo we have a uh sorry customer panel at our board meetings.

57:27 Our whole board can ask questions and My favorite question is what do you love about HubSpot? And then. And then what do you hate about HubSpot? And they kinda look at your shoes and come on And it's a great way. So so the employees' voice is here. Those company meetings, we have the the the customers in the company meetings.

57:45 We change the comp plan. So the management team got paid Not on revenue, but on retention and that promoter score. And so we worked very hard and kind of swung the pendulum to customer centric. Uh but I do think companies have one center of gravity or another.

58:00 There's a really interesting thread throughout this conversation of just when you wanna change how you operate, you have to go really far to a whole other and to 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 sings in. Same thing with marketing, but internally.

58:32 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.

58:49 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 is a big initiative. So people really lock in on what you say. And it turns out you have to be very repetitive and you have to be very careful what you say. Darmesh was on the podcast. You're uh illustrious co founder and he

59:16 Developed the whole system to avoid this sort of thing, flash tags. Or it's like an FYI. We had a whole system'cause we would say something on an email to the management team where it's flat. And everyone 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

59:36 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 It'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 l this all this all connects.

1:00:02 And by the way, you guys were co founders for Twenty years Um you shar something before we started recording. So f 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 wanna ever manage anyone. And you were talking about how you had to take on engineering, which didn't make any sense.

1:00:19 Mm I'm an engineer but I'm I can I can code, but it's not good. And so when we started the company's like and I I was the CEO before, I was terrible at it, I want to do it again. You gave me the CEO. I'm a great means like and by the way

1:00:32 I'm not gonna have any direct reports, I'm like, Well it's just the two of us, so don't worry about it's like, No ever Never. Like, yeah, yeah, yeah. And then we've got ten, twelve 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

1:00:53 What every direct reports is like. Surely you were kidding when you said that, he said, Nope. Is there Dermez Shah? has never had a single direct report at UpSpot. Incredible. I don't uh it's just like a dream. A dream

1:01:06 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 innovate. Yeah, I'm excited to get him back on the podcast someday. We're gonna get a link to that episode. Maybe a last question. I'm curious if there's anything else you think we missed.

1:01:22 Mm. As a As a company grows and scales, the job of a CO 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

1:01:34 And where your time goes is a See how as the company grows. We clicked on this earlier, but that inspiration thing I I I have a little rubric where it's like in the startup phase it's ninety percent perspiration, ten percent inspiration.

1:01:50 You get the scale up phase, it's ninety percent inspiration, ten percent persp 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 tr I have trust issues.

1:02:13 Like I only trusted a small number of people that have spot to be a DRI to really drive something important. It drove people crazy that I didn't have a a larger trust surface. Um, every one of the CEOs I work with has the same problem. And That's a that's a scaling limit. That was the limit for me.

1:02:31 Um I wasn't trusting enough. Brian, I feel like I could uh chat with you for hours. There's uh a whole list of haliganisms I'm gonna 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

1:02:46 think we should chat about anything you wanna leave a listener to it. I well I would say if you're a CEO And you're interested in scaling I think the halligan as opposed to like all the mistakes I made in my fifteen years of being CEO, I tried to summarize them there. To help you avoid them.

1:03:02 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. Right interview. I interview CEOs about this. So when he's interviewing me about being a CEO, I get to interview other people about being a C I'm kind of a CEO geek these days. And the the name of the podcast is the Grateful Dead reference. Which uh we haven't touched on, but you're huge.

1:03:22 Deadhead. 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 dad

1:03:36 were like the ultimate Silicon Valley startup. They started in nineteen sixty four. Do you know where they started, Lenny? Um no. Palo Alto. The early concerts were at Stanford were

1:03:50 All over Silicon Valley. They're a Silicon Valley company. They were very first principles in their thinking. They created a new category, a new way to distribute their music. It disintermediated the uh The ticketing companies Very innovative. Steve Jobs and Jerry Garcia are like

1:04:06 very similar in my mind, real crafts people. So I think of them as a great Silicon Valley success story. Uh you said he had a whole book about this. Uh what what's the book called just in case people want to dig it. 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.

1:04:30 Mm. Um It gets played like Dent Co played it. And There's a million Grateful Dead cover bands that let them play it, but I I'm taking care of it for For the deadheads.

1:04:41 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 teen was interesting. Garcia himself. Was a bluegrass guy. He's banjo player.

1:04:56 And then Bob Weir. recently passed was kind of a country Kruner. Yeah. Like country music.

1:05:04 then their their Uh bass player was a avant garde jazz tromboneist, Phil Lash. In there. Um keyboard player was a guy named Ron McKernan, Pig Pen. And he was like a harmonica guy.

1:05:18 And the drummer was like a marching band drummer. And so Spikyest 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 Study Hollywood.

1:05:34 And then They called it a jam band'cause they played rock and roll in a losy. Open, organic kind of. Jazzy way. And so spiky teams in creating categories.

1:05:46 Underrated. Incredible. Are you one of these people that have been to like a hundred Grateful Dead concerts, by the way? Makes sense. 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?

1:06:05 Mm. Let's do this. Fire it up. I've watched you do the right lightning round so many times. I'm flattered. Uh unsurprising questions. Uh what are two or three books that you find yourself recommending most to other people? I haven't read a book in a long time. I listen to podcasts.

1:06:20 I'm on X. I talked to a lot of other CEOs. I can't remember the last time I actually sat down and read a book. Much respect. I had Mark 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.

1:06:35 It's uh Either Twitter or books that are ten years or older and nothing between that. I'm hurt. Um yeah, I kinda stopped reading. I 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.

1:06:53 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.

1:07:09 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.

1:07:28 Most of the time. And Two steps. Two steps forward, ten steps back, two steps forward, ten steps back. Lots of lead bullets. A lot in like

1:07:38 And like unless we had alliances, like we had alliances with the French, we were screwed. Uh so I love that. Not It's a long one, but it's really good. How long is it? What are we getting into? Probably ten plus hours. Ten plus hours. It's a lot.

1:07:53 Uh but uh worth it is what I'm hearing. I'm in Boston, you know, it's surrounded by history. Yeah. All right. Uh favorite product you recently discovered that you really love? I love my Delphi clone. I teach a I teach course.

1:08:07 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, Lenybot.com is my Delphi, though we both have little bots. Uh the voice feature is the coolest thing, right? Just not good, great. I can't wait I hand video, they get rid of it, they're gonna bring it back, can't wait till it has video.

1:08:30 My least favorite, my lowest MTS product is my Sono system. You have shown us? I do and I I get you. Yes. People. Yeah. It's like so good in so many ways and so annoying in so many ways. Annoying. But like we still use it, you know, there's nothing better. Not a competitor. You and I should start a song as 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

1:08:52 understand how cool this is. So minus train 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 fit in space

1:09:04 Shared. Here's Here's your steps. Okay, what's even better about it is is you because you can go to ChatGPT and say, What would Lenny think about this? What it's added is the ability to put a bunch of documents in there that aren't on the internet. Like I put my My lectures in there.

1:09:19 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 Getting better, I like it a lot. Yeah, to that point, the Uh

1:09:30 I have an up uh uh promoted this feature of it, but it's trained on all my paid content too. So even if you're not a paid subscriber, you get access to all of the things I've ever shared. No, don't tell let's not tell too many people that'cause it's one day I'm gonna pay wallet in the near future. Anyway, enough about that. Leninbot.com. Do you have a favorite life motto that you find yourself

1:09:49 Coming back to In work or in life. This isn't lightning, but Four years ago. I had a very bad snowmobile accident, drove a snowmobile off a cliff.

1:10:00 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.

1:10:10 For a while. I was unconscious for a long time and woke up. And I didn't think I had my phone, so it sat there for a long time like I'm probably gonna die tonight. No one knows where I am. It's Fridge it out. It's in Vermont.

1:10:26 And I'm gonna freeze to death. And I sitting there for a couple of hours, I finally was like, Oh, I do have my phone. Dial nine one one, by the way, nine one one. Amazing service. And so the helicopters came in.

1:10:38 Yeah, took me out, took me to the hospital. And lots of surgeries and I was kinda out of commission for a year. Uh and I you can't see it but I got metal. All over me. All in me. Life short.

1:10:50 Like Life short. And I I made some decisions at the bottom of that cliff. The the one of the decisions I made at the bottom of that cliff was I don't really like being CEO of an eight thousand person company. Doesn't really suit

1:11:04 Me like my harmonic motion is 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.

1:11:16 Coming out of that was I gave the job to Yamani, who's still the CEO, doing a great job. A life short, don't waste it. I heard the story, but it's just as

1:11:25 How full hearing it again. What um why do you think it takes people why does it take a moment like that to help Yeah, someone realize This is I need a change, you know, or just like I think people think they're gonna live forever and

1:11:38 They're not. Um, as somebody who's fifty eight. 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.

1:11:55 Mm. Like this button. Same. I I appreciate it. Same. Um I read that you had twenty broken bones in this accident. Lot of broken metal. A lot of metal. I get thirty three screws in me. One loose one up here, then he

1:12:10 Mm-hmm. 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 w how a baseball team is run or just what it's like you know on the inside of a Team like the Red Sox.

1:12:27 It's not as profitable as people think. People think like these rich guys come in and buy these teams, but The way the lee is set up and the way the economics are set up. It's not. It's not a profitable endeavor. Whereas like

1:12:43 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. Like a four hundred million dollar payroll in the Miami Marlins.

1:12:59 Like a hundred million dollar payroll. 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 The next couple of years, but um it's kinda

1:13:12 It's a broken model. Intriguing. Uh Stay in AI SAS if you want to make money, is what I'm hearing. Vertical sass.

1:13:21 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 they How do they work with you if they wanted to, or did they have to be a Sigui Founder?

1:13:33 Uh and then how can listeners be useful to you? I can do this two things. I would love folks to listen to Longstrand Shit, my pod. And I would I get some comments, but not a ton. Like Lenny, you get more comments than yours, I'm jealous. I 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.

1:13:52 But like it's my family and Sequoia people giving me feedback on I 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 fate. Okay, here it comes. Uh, Brian, thank you so much for doing this.

1:14:10 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.

1:14:28 You can find all past episodes or learn more about the show. at Lenny's podcast dot com. See you in the next episode.

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