Brian Halligan on What It Takes to Be a CEO Now That Starting a Company Is Easy and Scaling One Is Hard
Lenny's Podcast
Brian Halligan co-founded HubSpot and ran it as CEO for about 15 years. He is now Sequoia's in-house CEO coach. He runs peer groups of founders, does one-on-one coaching, and hosts a CEO-focused podcast called Long Strange Trip. Lenny Rachitsky invited him on as someone who studies the CEO job closely. The conversation keeps returning to one tension that Halligan puts in his MIT course syllabus: starting a company has never been easier, and scaling one into a durable, high-impact organization has never been harder. His answers mix hiring tactics, a framework for judging founders, predictions about how AI will change go-to-market, and a set of "Halliganisms," lessons he drew from mistakes at HubSpot.
A "perpetual state of constructive dissatisfaction"
Lenny opened with a phrase one of HubSpot's board members used to describe Halligan: a perpetual state of constructive dissatisfaction. Halligan said he took it as a compliment. He sees the same trait in the fast-growing CEOs he now coaches. They rarely pause to take stock of what they have accomplished and stay focused on the end state.
He also said he has been surprised by how humble this generation of CEOs is. "Humble" was not the first word that would come to mind for his own generation, in his view, and he has been impressed by the difference.
The kids table and the adults table
At Sequoia, Halligan gathers CEOs into two groups. The "kids table" is about 15 CEOs of companies under 100 employees. The "adults table" is about 15 CEOs of companies above that size. He splits them because the problems at each stage are very different, although they rhyme a lot within each group.
When Lenny asked what distinguishes CEOs who graduate to the adults table, Halligan said the adults mostly want to talk about their executive team: how to build it and how to design the next layer of the org. He estimates they spend about half their time recruiting and interviewing. He remembers this from HubSpot's own growth, and says it surprises CEOs to discover that their job has become mostly interviewing and hiring.
He thinks most people, HubSpot included, are bad at it. CEOs overrate their ability to interview and their gut feel, and underrate a high-quality blind reference. He cited MongoDB CEO Dev Ittycheria, who told him that across roughly ten years as CEO, about two C-level executives turned over per year. Halligan didn't track HubSpot's number but suspects it was similar. His own rough guess is that at least half of C-level hires are gone within 18 months.
Hiring tactics: reading the board deck, blind references, and "spiky" candidates
Halligan admitted that even after many years, he still overrates his own interviewing ability. He offered several practices he considers better than the standard walk-through of a candidate's background.
The first comes from Parker Conrad. Before a C-level interview, Conrad has the candidate sign an NDA, sends them the latest board deck or memo, and schedules a half-hour conversation about it. If the candidate is purely complimentary, Conrad treats that as a major red flag, because he wants someone who will challenge him rather than a yes person. Halligan likes this as a way to see how someone thinks and how they will interact with you. He also recommends working through a problem together at a whiteboard.
The second is taking blind references seriously: find someone you know who worked with the candidate. From receiving many of these calls, Halligan says he can tell when the caller has already decided and is just checking a box. A caller who asks only for strengths and weaknesses has usually decided. The questions he finds revealing are harder ones. Would you enthusiastically rehire this person for that role? On a scale of 1 to 10, how likely are you to try to hire them back from me later? Were they in the top 1% of people you worked with? The top 10%?
The third is a change HubSpot made to how it read interview panels. Say one candidate for head of engineering gets four scores of 4 out of 4 and four scores of 2 out of 4 from eight interviewers, and another candidate gets 3 out of 4 from everyone. HubSpot almost always used to hire the consistent 3, the person with the fewest weaknesses. It switched to favoring the "spikier" candidate with real strengths and real weaknesses, and Halligan says its hit rate improved. HubSpot also shrank panels from about eight interviewers to about four. He noted a recent head-of-product hire was interviewed by only four people, and he thinks that worked.
His last piece of advice is one he says no one follows: hire slow and fire fast. Most people do the opposite.
Beware the big-company hire, and build like the 2004 Red Sox
Halligan called the big-company executive a mistake he made and says current CEOs are making too. A 50-person company hires someone with a fancy title from ten years at Microsoft. The result is a large impedance mismatch. The hire expects a company that has its act together, and a company of 50 or 500 people usually doesn't. HubSpot hired many people from Salesforce, Google, and Microsoft, and Halligan described attrition among them as essentially 100%.
Lenny mentioned the pattern of companies cycling through a McKinsey cohort, then an Apple cohort, then an Amazon cohort. Halligan said the McKinsey version "never works." His reasoning is that founders are, almost by definition, skeptical of conventional wisdom and unhappy with how some part of the world works, while someone who chooses to work at McKinsey tends to be conservative in outlook.
His alternative model is the 2004 Boston Red Sox, a team he now partly owns. That team broke an 86-year championship drought with a core of homegrown, high-quality, inexpensive players from its farm system, plus a few well-paid veterans such as David Ortiz, Pedro Martinez, and Curt Schilling. Halligan's point is that the mix worked and the culture held. Companies underrate homegrown talent "almost across the board." You don't want an entire team of been-there-done-that hires, and you don't want none. He noted that about half of HubSpot's management team has been there a long time, and pointed to Apple as another company with many homegrown leaders.
On how to act on this, he said an outside candidate usually interviews well, looks shiny, and hasn't shown you their warts, which you can only find through good blind referencing. So if an internal VP and an outside candidate are close, he would give the internal person the shot. He mentioned that Brian Chesky has argued companies over-rotate toward experienced outside management and delegation. Halligan thinks Chesky is mostly right, but observes that most CEOs he works with still follow the standard playbook of hiring heavily from outside.
The LOCKS framework for evaluating founders
Asked whether great CEOs share specific traits, Halligan described the rubric he uses when evaluating founders for Sequoia. He calls it his "LOCK" algorithm and added an S during the conversation:
- Lovable. He means inspiring followership rather than being nice. Steve Jobs may not have been lovable, but people wanted to follow him. Halligan's test: would a 28-year-old version of himself, fresh out of business school, crawl across broken glass to work for this person?
- Obsessed. He is wary of founders who came up with their problem six months ago. He prefers deep founder–market fit and evidence in someone's life of going obsessively down rabbit holes.
- Chip on the shoulder. He says he wouldn't have come up with this one himself; it is a Sequoia idea. Nearly all the founders have one, sometimes "a boulder," and he says he has one too.
- Knowledgeable. They know the domain deeply.
- Student. He named Winston Weinberg of Harvey, James Cadwallader of Profound, and Gabe Stengel of Rogo as deep students of the game. They constantly learn from him and from peers and also study history. He compared them to LLMs in how they keep absorbing information.
Lenny added a trait from his own research: extreme ambition, meaning an attempt at something most people would call crazy.
Born or made, and what founders must learn
Halligan does not think anyone can become a great CEO. He described a new kind of founder he calls the "five-tool" CEO, borrowing from baseball scouting, where a five-tool player who can hit, hit for power, run, catch, and throw is extremely rare. Bret Taylor is his example: someone who can code, has taste and vision, can sell the product, and can convince employees. Halligan says there are now several of these in Sequoia's portfolio, and he didn't see many before. In his view, neither Steve Jobs nor Jeff Bezos fit that profile.
Lenny suggested AI might help CEOs fill their gaps. Halligan was skeptical about the hard parts. A brilliant developer still has to convince investors to fund them at a high valuation, persuade top people to leave OpenAI and join them, and win over a skeptical Fortune 500 buyer. He thinks the effect may run the other way: "mere mortals" like himself, who can code a little, will suddenly be able to build things.
He listed several skills most founders have to learn. They must give constant positive and negative feedback, which feels unnatural to someone in their late 20s who has never managed a team or even captained a sports team. They must develop a good BS detector, because employees and outsiders are always trying to sell to them. And they must learn to inspire. His example was Winston Weinberg, who was a lawyer for a few years before founding Harvey and had never needed to inspire anyone.
Of these, feedback is the most common challenge he sees. Many CEOs are working through the same hard conversations. One is asking a co-founder who runs product and engineering to step into a CTO/"labs" role so an operator can be hired to run the engineering machine. Another is "layering" an early sales hire who built a team of ten but can't define the sales profile, unpack the process, or forecast accurately. Halligan calls these conversations uncomfortable and "unnatural for homo sapiens," and says the best CEOs study how to have them and get good at them.
What helps most, in his experience, is peers. He can weigh in at the kids and adults tables, but it is more effective when other CEOs do. "Misery loves company," he said, and the groups serve as a safe space.
Why starting is easy and scaling is hard
Halligan explained the syllabus line with an analogy from his own life. As a kid, a drugstore offered four or five toothbrushes. By the 1990s or 2000s, Amazon offered four or five thousand, made by thousands of companies. Making things got much easier. AWS did the same for software companies around the time HubSpot started, around 2006, and he expects the current jump to be even bigger. He predicts the number of companies formed will "mushroom" over the next ten years, as it did over the last ten. The result is so much noise and competition that standing out and accelerating is harder than ever.
Lenny framed this as largely a distribution problem. Halligan agreed and added that founders didn't grow up doing distribution. Scaling becomes a learning game, and the ones who learn fastest do best.
Why enterprise sales may be the last white-collar job AI replaces
Halligan had tweeted that sales may be the last job AI replaces. Inside HubSpot, he said, AI is working "incredibly well" in software development and customer support, and is starting to work well in legal. On the go-to-market side, progress has been slow beyond support, with perhaps the BDR role as the first to change. He believes traditional enterprise sales, built on trust between "two carbon-based life forms," will be very late to go.
He does expect the go-to-market funnel to be turned on its head. When HubSpot started, buyers searched Google, clicked a blue link, explored the website, filled in a contact-sales form, and waited for a rep. He predicts buyers will instead start research in ChatGPT, Gemini, or Anthropic's assistant. These tools already know everything on your website and about your competitors, so buyers will arrive much better educated and websites will matter less. He expects homepages to feature a high-quality avatar that knows the product, company, pricing, and packaging and can hold a real conversation. That conversation would be stored and scored in the CRM, and a human rep would follow up for considered purchases. On every sales call, the rep would have an all-knowing AI sales-engineer avatar instead of waiting for a human SE.
He tied this to what he wants as a knowledge worker. He has a Delphi clone of himself that he likes, and he wants it connected to his email and meeting-notes tools so it knows everything about him and can join meetings as a participant rather than a note-taker. He predicts every knowledge worker will have something like this in three to five years. Lenny compared this to the popularity of the personal agent project Clawdbot, since renamed. When Lenny asked if anyone was doing the homepage avatar well yet, Halligan said HubSpot has built one and it is working.
The first thing he expects to change is the top of the funnel: being found in AI assistants instead of Google (Lenny called this AEO), which changes how websites should be built.
"Forward deployed engineers" are sales engineers with a new name
Asked what AI-native companies are doing differently in go-to-market today, Halligan answered bluntly that almost nothing has changed. He expected things to be totally different in AI. Instead, the companies he works with are hiring the same kinds of people and running the same enterprise sales processes. The main difference is that sales engineers or solutions consultants are now called "forward deployed engineers." He spent the first ten years of his career at PTC, which he called an enterprise sales machine, and says enterprise sales hasn't changed much since the 1990s. He grants that these engineers may configure and train the product differently, and he's fine with the term. But in his view, the role looks very similar to what it replaced.
How the CEO job has changed: speed, focus, and the tax on optionality
The biggest change from 10 or 20 years ago, in Halligan's view, came from something Winston Weinberg told him about a year earlier. He was skeptical at first but now agrees: you can simply do much more. Agents and more productive developers mean something that took a year may now take two months.
He sees danger in this. A company with a deep, promising beachhead market may jump to its second act too quickly and lose focus on the first. He offered an imperfect analogy: OpenAI pursued many things beyond ChatGPT, then, when Gemini came out, refocused on the core.
He also thinks planning cycles have shrunk from a year to about three months. That puts pressure on CEOs to make decisions faster and better. Looking back, he said slowdowns at HubSpot were usually his fault, because hard one-way-door decisions were sitting on his desk, sometimes for as long as a year. Once he made them, everyone moved much faster. He said he always valued optionality, but now thinks there is "a massive tax" on optionality when you can move this fast and try so many things.
Halliganisms: "When you have to eat a sandwich, don't nibble" and "Next play"
Lenny walked through several of Halligan's "Halliganisms," which Halligan describes as a summary of the mistakes he made in 15 years as CEO.
The sandwich line comes from Google CFO Ruth Porat. Halligan applied it to a situation he expects: a retrenchment in valuations within the next couple of years. He described public markets as tight, "the anti-bubble," and private valuations as "a real bubble," and expects a reckoning in which many companies will need layoffs. The temptation is to do a small layoff, hope to grow into it, and then do another six months later. His advice is to rip the band-aid off, tell people the bad news because they are adults who can handle it, and get it done.
He paired this with Duke basketball coach Mike Krzyzewski's sideline call of "next play." A player who misses a shot tends to overcompensate on defense and compound the error with a foul. Krzyzewski wants the player to forget the miss and run the next play. At times, HubSpot put Krzyzewski's face on a slide at company meetings after an unforced error.
His example was the last day of March 2019, when HubSpot had a bad, day-long outage, something it had never really experienced. Customers were unhappy, many canceled, and many yelled at him. He said he cried in front of the whole company at the next company meeting, and used the "next play" slide. He added that most of the bad things that happened to HubSpot were self-inflicted. Companies, he said, are more likely to die of overeating than indigestion, usually from trying to do too much.
"Never waste a good crisis"
Halligan said most of the good things that happened at HubSpot came out of crises, because the company took drastic measures to fix problems and prevent a repeat. After the 2019 outage, HubSpot rethought how it built and deployed software. He says it hasn't had a serious outage since, and quality is much better.
The crisis also forced a mindset shift. HubSpot started as marketing software and pivoted into CRM after Salesforce entered its market. A bug in marketing workflows is bad but survivable. A CRM outage on the last day of a quarter directly hurts customers' ability to do business. The company hadn't fully absorbed how important it had become to its customers. Halligan said HubSpot "always overcorrected," deliberately swinging the pendulum hard the other way so everyone could see what was changing.
"If you want to kill a plant, have two people water it"
If you leave for a month and ask two friends to water your plant, Halligan said, it will either be overwatered or not watered at all, and it dies either way. Every CEO at his adults table has learned this and is "religious" about the DRI, the directly responsible individual. Kids-table CEOs talk about DRIs, but it doesn't bite until a company reaches scale.
His explanation: in a small company everyone is in the room. On a pilot with a big account, sales, service, and engineering all know what's going on. At scale, those functions become separate organizations that don't know what the others are doing. Yet everything important at scale happens cross-functionally, so one powerful person must own it, with the authority to tell people in other divisions what to do even though they don't report to that person. Committees, he agreed with Lenny, never work.
No silver bullets, and no one coming to rescue you
Halligan said he used to believe, wrongly, that one hire, one investor, one event, or one product release would be a silver bullet. From outside, HubSpot's trajectory looked smooth and up and to the right. From inside, it felt like two steps forward and one step back, over and over, often because a crisis caused the step back.
He added that founder CEOs, especially in their 20s, learn during their first crisis that no one will rescue them: not parents, not VCs, not a thesis advisor. You can get help, but it is on you. Even in his coaching role, he said, he can be a shoulder to cry on and offer advice, but the responsibility stays with the founder.
Asked whether he talks people out of starting companies, Halligan said he does, often. He noted that he'd heard Jensen Huang say he wouldn't start Nvidia again. Halligan said that he himself would start HubSpot again, even though it was very hard, involved many sacrifices, and wasn't glamorous. He cited a line he attributes to the Dalai Lama about living a good life so you can live it again on your deathbed.
On work intensity, he said the founders he works with go well beyond "996." They work seven days a week, are always on, and text him on Sunday nights. He attributes this to founders seeing a massive platform shift and not wanting to waste the opportunity, and he thinks that mindset is right. By his account, he worked 60 to 70 hours a week and never really turned off, but today's founders are "much more hardcore," which he suspects Elon Musk has inspired. He said he doesn't recommend it and didn't have work-life balance himself. The one exception he knows is Kareem Amin of Clay, who tells people to take weekends; Halligan plans to interview him about that. Lenny joked that Clay took a long time to find product-market fit, though it worked out.
EV > TV > ME, and how HubSpot enforced it
This formula stands for enterprise value over team value over "me" value. As HubSpot scaled, Halligan said, VPs with sizable organizations often failed by optimizing for their own teams rather than the company. A sales leader paid on bookings might maximize bookings and leave service to deal with the downstream problems. Similar conflicts arose between marketing and sales and between other departments. Employees noticed and complained.
It showed up in HubSpot's quarterly employee net promoter survey, broken down by department. If sales had been running at 65, 62, 68 and suddenly dropped to 30, the comments were usually about the leader, often about this kind of team-first behavior. HubSpot shared the feedback with the VP and tried to help. But Halligan said the score would typically fall further, to around −5, the next quarter, and leaders almost never recovered. Once you lose your team, he said, it's hard to get them back, which is another reason to fire fast. He said this doesn't appear in the first 100 to 150 employees but emerges once layers form between the CEO and staff. HubSpot later added CV, customer value, at the front: customers first, then HubSpot, then the team, then yourself.
Halligan also quoted Steve Jobs's line that you don't work for your boss, you work for Apple. On making the principle concrete, he described several practices. The principle was an explicit scored item in performance reviews. He repeated it constantly. Early on, he ran HubSpot somewhat like Jensen Huang runs Nvidia, without one-on-ones, giving good and bad feedback publicly in large management meetings and going out of his way to criticize people who put their team over the company. At each well-produced quarterly company meeting, the co-founders handed out "champagne awards," signed bottles of Veuve with a note read aloud, and usually one recognized enterprise-first behavior.
Employee-centric vs. customer-centric
Halligan believes every company has one center of gravity: customers, employees, or investors. For its first several years, HubSpot was more employee-centric than customer-centric. It was ranked the number-one place to work on Glassdoor, and he was the top-rated CEO there. Looking back, he's not sure that was good. He no longer thinks wanting to be liked is a good trait in a CEO, and he pointed to Tobi Lütke of Shopify, whose ratings aren't great while the company does very well. HubSpot over-indexed partly because his co-founder was strongly focused on it and because it had a powerful head of HR, Katie Burke. In a four-hour management meeting, about two hours would go to employee topics.
Eventually he asked why they spent so much time on employee NPS. If employee NPS was 60 and customer NPS was 25, he said he would trade ten points of the former for ten of the latter. Several changes moved the center of gravity. HubSpot's management team met monthly, and each meeting included a customer panel where Halligan asked pointed questions to surface bad news. Board meetings also got customer panels, where his favorite questions are what customers love and what they hate about HubSpot. Customers appeared at company meetings. Management compensation shifted from revenue to retention and customer NPS.
Lenny noticed a pattern: changing culture seems to require overcorrecting. Halligan agreed and added two observations about the CEO role at scale. First, you have to say the same thing "over and over and over" before it sinks in. Second, people put you on a pedestal you don't deserve. A casual hallway remark along the lines of "it'd be cool if we had a product that did X" could send someone home to build it as "a big initiative Brian wants." So CEOs must be repetitive and careful about what they say. HubSpot responded with a tagging system, which Lenny said co-founder Dharmesh Shah had described, to label each message by intent: something that must get done, something to discuss, or just an FYI.
Halligan also told the story of Dharmesh's condition for co-founding HubSpot. Dharmesh had been a CEO before, considered himself bad at it, wanted Halligan to be CEO, and said he would never have direct reports. Halligan assumed he was joking. When HubSpot reached 10 or 12 people and needed someone to manage engineers, Dharmesh reminded him of the promise. Halligan, who is an engineer but says his own coding isn't good, ended up managing them. According to Halligan, Dharmesh has never had a single direct report at HubSpot, which freed him to think and be creative.
From perspiration to inspiration, and the limits of trust
On how the CEO's time shifts with scale, Halligan used his own rubric. The startup phase is 90% perspiration and 10% inspiration, and the scale-up phase is the reverse. In a startup you do every job, and even later you must stay close to the work and keep talking to customers. But you also have to let go of a great deal for the organization to scale.
He was candid that this was his own limit. He said he has trust issues and trusted only a small number of people at HubSpot to be DRIs for important work, which drove people crazy. Every CEO he works with has the same problem, and he considers it a scaling limit.
The Grateful Dead as a Silicon Valley startup
Halligan's podcast title references the Grateful Dead, and he wrote a book, Marketing Lessons from the Grateful Dead. He calls the band the ultimate Silicon Valley startup. They started in 1964 in Palo Alto, played early shows around Stanford and the Valley, thought from first principles, created a new category, found new ways to distribute their music, and disintermediated ticketing companies. He sees Jerry Garcia and Steve Jobs as similar craftspeople. He bought one of Garcia's guitars and describes himself as its steward. Dead & Company and many cover bands have played it.
His main lesson from the band is about spiky teams. Garcia was a bluegrass banjo player. Bob Weir, who Halligan noted recently passed, came from country music. Bassist Phil Lesh was an avant-garde jazz trombonist, keyboardist Ron "Pigpen" McKernan was a harmonica player, and the drummer came from marching band. Together they created a new genre, the jam band: rock and roll played in a bluesy, open, jazzy way. For Halligan, spiky teams are underrated in creating categories.
Lightning round: no books, Ken Burns, Delphi, and a snowmobile accident
Halligan said he can't remember the last book he read. He gets information from podcasts, X, and other CEOs. His recent favorite viewing was Ken Burns's long documentary on the American Revolution, "probably 10 plus hours." He admires Burns's craft and sees America as a disruptive startup. The war, as he described it, was "two steps forward, ten steps back," the country came very close to losing most of the time, and it depended on alliances like the one with France.
His favorite product is his Delphi clone, which handles office hours for his course, Scaling Entrepreneurial Ventures. He especially likes the voice feature, looks forward to video returning, and values being able to upload documents that aren't on the internet, such as his lectures, plus a feature where it interviews him. His lowest-rated product is his Sonos system. Lenny agreed it is good in many ways and annoying in many others, and both admitted they still use it.
His life motto came from a snowmobile accident about four years earlier in Vermont. He drove off a cliff and lay unconscious at the bottom for a long time. When he woke, he initially thought he didn't have his phone and expected to freeze to death overnight. After a couple of hours he realized he did have it and called 911. A helicopter took him to the hospital. He had many surgeries, was out of commission for about a year, and now has 33 screws in him. At the bottom of that cliff, he decided he didn't enjoy being CEO of an 8,000-person company and would step down if he survived. He handed the job to Yamini Rangan, who he says is still CEO and doing a great job. His motto is simply that life is short. He thinks people act as if they'll live forever. At 58, he says he is much more intentional about his decisions and the people he spends time with, and tries to work on things that bring him joy.
On the Red Sox, he said owning a baseball team is less profitable than people assume because of how the league's economics are structured. He considers baseball flawed without a salary cap, contrasting the Dodgers' roughly $400 million payroll with the Marlins' roughly $100 million. He thinks the model is broken and predicts it will be corrected in the next couple of years.
He closed with a request. Long Strange Trip started only a couple of months ago, and most of his feedback so far comes from family and Sequoia colleagues. He asked listeners to tell him honestly what they think of it.
The thing about being a founder CEO is there's no one there to rescue you. Your parents aren't going to rescue you. Your VC is not going to rescue you. That kind of hits you when you hit your first crisis.
Starting a company has never been easier. Scaling one into a durable, high impact organization has never been harder.
The number of companies formed is going to mushroom over the next 10 years relative to the last 10 years. It's just going to be hard to stand out and really accelerate.
What's most different about what it was like to be a CEO maybe 10, 20 years ago versus today?
There's a massive tax and optionality when you can move this fast and try a lot of things. It puts pressure on the CEOs to be faster and better decision makers. A lot of people in the world want to be founders. They want to be CEOs. I don't think anyone can do it. People talk about 996. It's way more than that. Founders are 7 days a week. They're always on. I text Sunday nights. It's full contact.
Do you feel like there are specific profiles or traits to be successful?
I look for four things. I call it my LOCKS algorithm.
Today my guest is Brian Halligan, co-founder and longtime CEO of HubSpot. I asked Brian to come on this podcast because he is, more than anyone I've met, a student of the job of a CEO. After leaving HubSpot last year, he became the in-house CEO coach at Sequoia, where he brings together dozens of top CEOs to learn from each other. He does one-on-one coaching with some of the world's top CEOs. He also hosts a popular podcast called Long Strange Trip where he interviews some of the world's most successful CEOs. In this conversation, we unpack what it takes to be a successful CEO in today's era. Let's get into it after a short word from our wonderful sponsors.
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Brian, thank you so much for being here and welcome to the podcast.
Thanks for having me, Lenny.
It's my pleasure. I want to start with something that I've heard your board members, the way they described you, is someone with a perpetual state of constructive dissatisfaction. Do you think this is a core foundational kind of trait of successful CEOs, successful leaders?
By the way, I like that description. When she did, a woman named Lori Norington who's sub chair said that, I like it. I took it as kind of a compliment, and I liked it. And as I, so I spend most of my time these days coaching very fast growth CEOs. They all are kind of like that. They're all in kind of a state of perpetual dissatisfaction, but in a positive way.
One of the things, by the way, I like about the current crop of CEOs, they don't really take stock of what they've done and feel it. They're always a little bit dissatisfied with where they are and very focused on the end state. And I've been surprised at how humble this generation is of CEOs. And I think of my generation of CEOs as being, I don't know, humble wasn't the first word that would come out of your mouth when you describe kind of my generation, but this generation I feel like is different. And I've been impressed with it.
Okay. I have a bunch of questions along these lines, because one, you've been a CEO of an incredibly successful company for a long time, for about 20 years before you moved on to this new chapter. Now you work with a bunch of CEOs. You're Sequoia's in-house coach. There's a few things that I've heard you do. One is you gather groups of CEOs, and what I've read is that you have kind of two tables. You have the kids table and the adults table. The kids table is CEOs of companies that are under about 100 employees. The adults table is over 100 employees. So let me ask you, when you look at CEOs that move from the kids table to the adults table, other than just, you know, they scale and grow, what is it that these CEOs that graduate from the kids to adults table do differently?
The adults are really focused on, and all they really want to talk about is, their exec team, their direct reports. How do you build our exec team? That next level down org design. You would be surprised how much they think about that. And on average, I would say the adults are spending half their time just recruiting and interviewing. It's pretty all-consuming, and I remember that from that phase in HubSpot's growth, and it surprises people, like, wow, my job is really just to interview and hire. I didn't know that was going to be the case. So that is one that they kind of are making that transition.
And I would just say in general people are very bad at this, and HubSpot was too. I think CEOs and everyone dramatically overrate their ability to interview and overrate their gut feeling and underrate a really high quality blind reference.
And I interviewed Dev, the CEO from MongoDB, the other day and he had an interesting stat. On average over his like 10-year lifespan as a CEO, there were two C-levels turned over per year. That's a lot of turnover at the top. And I didn't keep track of it like Dev, but I think HubSpot was kind of similar. And all of these startups are kind of similar too. And so people are working on that and struggling with it as one thing in common with all of them.
What do you do when you coach someone on that, when you're like, okay, you think you're amazing at interviewing, you think you know who's going to work out? What advice do you give them to help them develop that skill?
I think even me, I've been doing this for 150 years, I still think I overrate my ability to interview someone and really know if they're a good fit. I give a couple pieces of advice.
Parker Conrad has a good hack that I like. Before he's got a C-level interview, CFO, chief product officer, whatever, he has them sign an NDA and sends them the last board deck or the board memo or some important doc, and he schedules a half-hour interview with them. And he just has a chat about the deck. And if they're just very complimentary and it's so great, you're doing this amazing thing, it's a major red flag to him because he wants someone that will challenge him and not a yes person. And I thought that was a pretty good hack to get inside someone's head and how they think and how they'll interact with you.
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. And I coach people to do blind references. Find someone you know that worked with them. VCs are good at this, by the way. And I get a lot of these and you can tell some of them are like, "We've already decided, we're checking the box," versus they're asking me hard questions about this person. And one of my favorite questions people ask is, "Would you enthusiastically rehire this person for that role?" which I think is a really good question. On a scale of 1 to 10, how likely is it that you'll try to rehire this person back from me down the road? I think those types of questions are good. So not mailing it in on those blind references, I think, is really good.
My other piece of advice, and no one listens to me on this, is hire slow and fire fast. People hire fast and fire slow. And if I had to guess, Lenny, within 18 months after you hire a C-level exec, at least 50% of the time they're gone. There's this high mortality rate on them. It's harder than people think.
And 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 think the blind references are key. I think doing like real interactive working on a project together.
I'll tell you one other thing we learned at HubSpot about this. We would have a candidate come in, let's say a head of engineering, and we'd have like eight people interview them, and our scale is one to four, and let's say four people were four out of four and four people were two out of four. So that's candidate A. And then the next candidate comes in, eight people interview them, and everyone's a three out of four. Almost every time we hired the three out of four, like the person with the least amount of weaknesses. And we changed it and we went with the spikier people. We went with people with weaknesses. We went with people with challenge stuff. And that has worked out quite well. Our hit rate at HubSpot improved. We also have shrunk the pool of people on that interview panel from eight to like four. We just hired a head of product and there were just four of us that interviewed them. I think that worked too. So I think there's things you can do to get better at it for sure.
Okay, this is incredibly tactical and useful. On the references piece, the toughest part is getting people to be honest, because there's very little upside to them to say negative things about people. Is there anything that you've learned to help get real honest answers from folks you call for references?
Well, I can just say, because I don't do this a lot anymore, but when people call me, I can tell if they've already decided. When they're really just looking for, like, when they ask me for the strengths and weaknesses, I'm like, oh, they've already decided. When they ask me something hard, like on a scale of 1 to 10, how likely are you to hire them again? Stuff like that that kind of gets at the core. Or were they the top 1% of your employees? That's a good question. Oh, were they top 10? That type of question is pretty good. So when I'm on the other side of it, I like when those types of questions come up.
I'll tell you the other mistake everyone makes, I made, and all the CEOs are making now is you're hiring for that, whatever, head of engineering, and you're blown away by the resume. Like you're 50 employees and you're hiring this person who's been at Microsoft the last 10 years and has a fancy title and fancy division in Microsoft, and you hire them. There's just a massive impedance mismatch when you hire them on what their expectations are, what your expectations are, and the extent that you've got your together. You definitely don't if you're 50 or 500 employees, and they expect you to have your act together. And so that is another, like, avoid the big company hire. We hired so many people from Salesforce and Google, Microsoft, like 100% attrition rate on all those folks.
Something that I've seen at a lot of companies is there's like phases of, okay, now the McKinsey cohort comes in and we think that's going to be the answer, and then it's the Apple group, and then that didn't work out. Then the Amazon group.
The McKinsey one never works. It never works. It never works. By definition, they would fail on my spectrum of, like, most founders are like me. They are skeptical of conventional wisdom. They're unhappy with how the world works in some way. And so they're kind of far on that spectrum of rethinking conventional wisdom. And almost by definition, somebody who goes to work for McKinsey is very conservative in their outlook. And so I think that almost always fails.
We're on this hiring thread, so let me keep following this conversation. I read somewhere that you recommend building your team like the 2004 Red Sox. What does this mean?
Well, I'm a big sports fan, a big Boston Red Sox fan, and the Boston Red Sox hadn't won, Lenny, a World Series in 86 years since they traded... and they finally broke, they finally won it in 2004. And the way they won it was they had a team of a bunch of homegrown, really high quality, inexpensive talent that they drafted and came through the farm system, and then they got a few free agents like David Ortiz that a lot of people have heard of that they paid a fair amount of money to. Pedro Martinez and Curt Schilling were kind of the canonical older, been there, done that, bigger company folks, and they mixed really nicely. The culture really worked, and I think that's the key. I think people underrate their homegrown talent, almost across the board they underrate it, and I think you want that mix. You don't want to hire a whole bunch of been there, done that. You don't want to hire none of them.
I imagine this is public, but you're now a part owner of the Red Sox. Is that...
I am a part owner of the Red Sox. Yes.
Okay. I have questions for you along those lines. Okay. That's amazing advice. 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 don't underestimate the power of someone internal rising to the occasion.
Yeah. If you look at HubSpot, like half the management team are folks that have been there for approximately 150 years, which I like. And same with, like, you look at Apple, a lot of those people are homegrown.
And so are there any tips here for doing this well? Is it just like give people a chance?
I tend to give people a chance. It's like if you're interviewing someone that's homegrown, their VP, for that C-level job versus hiring someone from the outside. You 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 warts. Hard to figure out their warts unless you're very good at blind referencing. And so you tend to overrate them and underrate your homegrown. So if it's pretty close, I think you give your homegrown a shot at it.
What's interesting to me, Lenny, is, you know, Brian Chesky sort of rethought a lot of this stuff. And he's like, everyone's over-rotating to the experienced talent and management teams and delegation. And I think he's mostly right about that. People haven't really followed that. People are, you know,
they're hiring people from the outside quite a bit. That's kind of the standard part of the playbook that all of them are following now. It's a little different. It's actually quite different than what Brian's espousing.
Going back to the conversation around CEOs. A lot of people listening to this podcast, there's a lot of people in the world want to be founders. They want to be CEOs. At the same time, you look at Elon, you look at Jensen, you look at Steve Jobs, you look at you. A lot of people are like, I can't. I'm not this person. I'm not going to be as good as them. There's no world where I'm this good. Do you feel like there are specific profiles or just like traits that you have to be born with to be a successful CEO or do you think it's all learnable? Anybody can be successful if they really work hard in school.
I meet all these CEOs coming in and I have a little like algorithm in my head and I look for four things. I call it my LOCK algorithm. L is for lovable. And you know, Steve Jobs, you would say, is kind of rough and maybe not lovable, but he would inspire followership. You would want to follow him. And so, could I envision a 28-year-old me graduating from business school going to work for this person? Would I crawl across broken glass? That's question one.
Two is just obsession. Are they deeply obsessed with this problem? I'm a little negative on people who came up with this problem to solve six months ago and started a company. I like people with deep founder market fit who've been thinking about it for a long time and have evidence in their lives of going deep down obsessively down a rabbit hole because that's kind of what it takes to be a founder CEO.
The C is something I wouldn't have thought of, but this is a Sequoia thing, like chip on the shoulder. Pretty much all of them have a bit, be like a boulder on their shoulder. And I have a bit of a chip on my shoulder, too. And the K is just for deeply knowledgeable about the domain.
And so I kind of look for that. If I were to stick an S on it, I would say student. Like I look at Winston Weinberg from Harvey or James from Profound or Gabe from Rogo, some of these new very fast growing companies. They're students of the game. They're not just learn-it-alls. They're deep, deep, deep students of the game. And they're 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. So, 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 a ton of folks like me. What do you think's in common
of what successful founders? Oh my god, I wish I had my succinct answer. I would go to lennybot.com and be like, what is the common pattern across these folks? One that you didn't mention that I think is interesting, I did some research on this recently with Terren Rohan, is just extremely ambitious, just trying to do something really wild that most people are like, that's crazy. You're not going to get a subscription service for all music in the world. What are you doing? Do it and you're going to do that.
And like is it learnable? I notice a lot of the CEOs struggling with a couple things. Like let's say you're Winston, you're late 20s, you've never managed a team. You're probably never even captain of a sports team before. And in order to scale, you have to give people feedback constantly and it's very unnatural. It's like I'm going to give this VP I hired a bunch of feedback, positive and negative. And if you don't get good at that, you really pay the price later.
That's something I think they have to learn. They all have to learn to get a good BS detector. They're constantly being spun. Everyone's trying to sell to them. The org is always trying to sell to them. So, that's sort of something they have to develop, you know, over time. They have to all get good at the inspiration thing over time. Like you're Winston. You've never had to inspire anyone in your entire life. You went to school and you're a lawyer for a few years and you started this thing. Inspiration wasn't your thing. So there's certain things you have to kind of learn on that startup to scale-up path and the best ones learn it very fast.
This is extremely interesting and useful. So LOCK with an S at the end, just to kind of mirror back what you're sharing. So when you were saying you evaluate CEOs, is this for investing? Okay, so when you're helping Sequoia decide should we invest in this company, what you look for is LOCKS. I like the S, I'm going to include it there. So are they lovable? Are they inspiring? Are they obsessed with this problem they're going after? Do they have a chip on their shoulder? Are they extremely knowledgeable about the problem they're going after? And it sounds like not just the problem, but just studying companies' business strategy, things like that. And then S was student. I guess that's what S is, student is studying being a founder, being a CEO. Okay. So, I guess going back just to the question, do you think, just to put it very simply, do you think CEOs are born or do you think they're made? Can anyone turn into an amazing student?
I don't think anyone can do it. I don't think it's just anyone. I will say I've noticed that, so another little rubric I have, and I don't see a lot of these, but like Bret Taylor's one. There's a few out there that are in Sequoia's portfolio. I call them, back to the baseball thing, a five-tool player. In baseball when you rank a player, it's can they hit? Can they hit with power? Can they run? Can they catch a ball? Can they throw the ball? And they rate them kind of one to 10 at each. And it's very rare that you have a five-tool player, like extremely rare. And the thing that's kind of new now is there are five-tool CEOs, like Bret Taylor's one. You can code, you have taste, you have vision, you can sell the product, you can convince employees, like this kind of super CEO. And there's a bunch of them now. And I don't know, I didn't see a lot of those. That certainly wasn't Steve Jobs. He wasn't programming. It wasn't Jeff Bezos. You know, I think there's kind of a new breed that's quite impressive.
These folks you mentioned were this good before AI became a thing. I imagine AI helps more CEOs fill the gaps that they have.
I think it's hard to fill the gap of, you know, this guy's a developer. He's brilliant, genius level, obsessive, but can he sell? Can he convince an investor to give him a lot of money at a high valuation? Can he convince brilliant employees to leave OpenAI and join him? Can he convince some big skeptical Fortune 500 enterprise to buy his product? Being able to do that and have taste and be able to code really well at next levels, I think is rare. I actually think it might be the other way though, where mere mortals like me who can kind of code, all of a sudden we're going to be able to build stuff. I think it kind of goes the other way.
I love this list you shared of things that you find CEOs most have to learn. BS detection, inspiring people, giving hard feedback. What's maybe the one thing that most often people that become CEOs, founders have to work on? Is there a most common thread of, here's the thing you probably need to work on most?
It's that feedback thing. All of the CEOs are building their teams and so many are like, I have a co-founder that runs product and engineering, but I need that co-founder to kind of step aside and be the CTO and the thinker and the labs person, and I need to hire somebody who can actually run the engineering machine. So many of the CEOs are going through that right now. That's a tricky transition. So many of the CEOs are layering folks. Like you hired that early head of sales. He hired 10 people but just can't quite figure out the sales profile. Can't quite unpack the sales process. Can't quite forecast accurately. We need to layer the person. You know, those types of conversations are very tricky and quite unnatural for homo sapiens to have if you're 25 and you've never done anything like that before. So, I see the best ones getting really good at that and studying it. It's super uncomfortable, but they have to kind of suck it up and get good at it.
What do you find most helps them build these skills, get better at this? Are there some kind of tidbits of advice you give them? Is it something that they study to improve?
I think misery loves company on this. Part of what I do, the kids table is 15 CEOs of companies under 100 employees and the adults table are CEOs of companies over 100 employees, about 15 of them. They talk about this with each other. It's kind of a safe space and I can weigh in, but it's actually much more effective when their peers weigh in. I think misery really does love company on stuff like this. They learn from each other.
So essentially it's find peers to talk to and share and be a component of.
And the reason I break it out is the problems at the kids table are very different than the problems at the adult table. And they all rhyme, they rhyme a lot.
So you teach a course at MIT around scaling startups and it's specifically around scaling, not starting the company, and you have this quote in your syllabus: starting a company has never been easier, scaling one into a durable, high-impact organization has never been harder. Why is that the case?
I mean, has it ever been easier to start a company? It's absolutely true. And the flip side of that is, I mean, the number of companies formed is going to mushroom over the next 10 years relative to the last 10 years. And the last 10 years compared to the previous 10 years mushroomed. I just think in my life, like I'm old, and when I was a kid I'd walk into CVS, the corner drugstore, and I want to buy a toothbrush, there are four or five there, you pick one. And you know, in like the 90s or 2000s you go to Amazon, there are four or 5,000 toothbrushes, four or 5,000 companies creating those toothbrushes. It got much, much easier to make stuff. And even technology, AWS just made it easier to start a software company. So, it was a huge jump back then when we started up about 2006, but now it's going to be an even bigger jump. So, it's easier to start now. There's so much noise in competition, it's just going to be hard to stand out and really accelerate and scale. So, that's why I say it's never been easier to start. There's never been more competition. It's never been harder to scale.
And a big part of this is distribution essentially. Breaking through the noise is what I'm hearing.
And it's hard to learn that. Like you didn't grow up doing distribution. You don't know. So they're all learning it. And the ones that learn fast, it's like a learning game. The faster you learn, you know, the better you do.
Along these lines, I saw you tweet this recently where people talk about which jobs AI is going to replace and you said that sales is maybe the last job AI will replace. Why do you think that's the case?
Well, if you look inside a typical enterprise, where's AI really working? Let's say inside of HubSpot, software development is working incredibly well. Customer support incredibly well. Legal starting to work incredibly well, but there really aren't apps in the rest of the org that have really changed things a lot. And the go-to-market side's been kind of slow, really just support. There isn't a canonical marketing or sales, or maybe the BDR is the first one, but I think ye olde enterprise sales, where there's actual trust built up between two carbon-based life forms, I think will be very, very, very late to go in the white-collar world.
I also think a lot about the go-to-market. I think the go-to-market's going to get turned on its head. When we started HubSpot, if I think of the way the funnel worked, you want to get found in Google, someone clicks on a blue link, they land on your website, they go down the rabbit hole, they click on contact sales, they wait until that sales rep's ready, go down that rabbit hole. And I think it's going to get turned on its head where people are evaluating a product, they start in Gemini or they start in Anthropic or they start in ChatGPT, and, you know, for example, ChatGPT knows way more about you. It knows everything on your website, everything beyond that, knows all your competitors. So they will stay in there and do lots more research and be incredibly well educated. So your website's a lot less important. And they go to your site, I think sites will change where you're going to have a really high-quality avatar that knows everything about your products, knows everything about your company and your pricing and packaging, and you can have a high-quality conversation with that person. That will get stored in your CRM and will get, you know, scored, this is a good quality conversation, and then the sales rep will follow up, but that sales rep will have an avatar with them on every sales call. You won't have to wait for their SE. They'll have their own SE that's all-knowing that will follow them through the process. So go-to-market hasn't changed much yet, but I think over time it's going to change a lot.
This avatar, just to understand, so this is the buyer has their own little agent that comes with them, or on HubSpot, you have this avatar that walks you through the sales process?
I think both. I think me as a knowledge worker, what I really want as a homo sapien is, I have like a Delphi clone that I really like.
Same.
It's actually quite good.
Yeah. Where do people find yours?
They find it on my footer. They can find it on Delphi.
We'll link to it.
Yeah. And what I want is connect that thing to my email, into my Granola, into my Plaud, and it knows everything about me. And then when I go to a meeting, Lenny, I want to invite that thing to my meeting. So it's sitting there in the Zoom meeting. It's not just taking notes like Granola. It's a participant. So if I forgot something, I ask it a question. If somebody else forgot... I think every knowledge worker will have one of these in three, four, five years. But mine was more on the go-to-market side, where I think every website will change and there'll be an all-knowing avatar on that homepage. And if it's a considered purchase, I think it gets handed off to a sales rep. That sales rep has a conversation, but when that sales rep's on Zoom, they have their SE avatar that's kind of all-knowing. So, I think this stuff all changes a lot in the next few years, but it hasn't really unlocked yet.
What are we going to be doing in this world? These two bots chatting with each other.
It's going to be great, Lenny. You and I are gonna be sitting on a...
Podcasting, kicking back, relaxing on a monthlong vacation, sending our avatars to all the meetings.
Go buy me some HubSpot seats, please. I think this is why Clawdbot was so popular. I think this is essentially what they're building, this idea, which is now called Moltbot, which might be changing again. It's just this personal little agent that can go do stuff for you.
Totally.
So you're talking about the future of go-to-market is this world where there's these little bots and agents that are doing things for you on both sides. When you look at companies today that you work with that are doing well, that are especially AI-driven companies, what are they doing differently in terms of go-to-market that is working really well?
Honestly the only thing that's different today, it's exactly the same as it's been for 100 years, except they call their SEs, or their system consultants, forward deployed engineers. The rest of it is the same. I thought it would be
totally different in AI. I'm working with all these companies. They're hiring like all the same folks and running the same enterprise sales processes. So, it hasn't changed that much, at least on the enterprise side. It actually hasn't. I spent the first 10 years of my career at a company called PTC, which is like an enterprise sales machine. Enterprise sales hasn't changed that much since the 1990s.
Okay. And so, forward deployed engineer, very hot term. The idea there is they come work with the customer and help them implement this thing. And that's come up a lot on this podcast just with AI tools. Rarely are they just plug-and-play. 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 versus like sales engineering in the past, things like that?
It's a solutions consultant, sales engineer. They're technical. They help you implement it. They connect all your systems. They customize it. It's different. I mean, you're training it in a different way, but I think, well, anyway, I think the term is fine. 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 continue to lean into this idea of having your employees help the customer onboard, be successful, integrate, all that stuff.
I think the thing that will change first is the top of the funnel around getting found. Instead of Google, you got to get found in these...
Yeah. AEO.
Yeah, that's going to be really important. And the way you build your website is very different to optimize for it. And then I think your homepage is totally different. I think you land on an avatar and have a conversation with them versus you're going through all the pages on your site. I think the top of the funnel is about to change a lot.
Is anyone doing this well yet, this idea of this avatar, or is this just kind of in the future?
If you start a program, HubSpot does it. We built one. It's working.
Okay. Let me ask one more question around CEO stuff and then I want to move on to Halliganisms.
All right.
How is just being a CEO different than it was? So you've been doing this for 20-ish years.
Yeah.
What's most different about what it was like to be a CEO maybe 10, 20 years ago versus today?
One of my CEOs, it was actually Winston from Harvey, said this like a year ago and I was like, that's... But I actually think he was right. He's like, you can just do a lot more. I mean, you've got AI agents doing stuff. Everyone's more productive. The software developers are more productive. Like something that used to take you a year takes two months now. And so the amount of projects and the amount of stuff you can do is much, much more.
I think he's right. I think that's a little dangerous. Like let's say you found your beachhead market and that beachhead market is really good and it's very deep. There's a lot of work to do. I think what's dangerous for companies is they hop to that second act too quickly and they lose focus on that first act. And this isn't a completely perfect analogy, but you think of OpenAI and ChatGPT, and its consumer app is doing incredible, and they're doing lots and lots of other things, and then Gemini comes out and they've kind of focused back on the core.
I think there's a lot of competition. Everything's moving fast. I do think people get more done and I think that impacts everything. Like the planning cycles used to be a year. I think the planning cycles now are 3 months long. Yeah, that's a big change. I think it puts pressure on the CEOs to be faster and better decision makers.
Like I just think of times in HubSpot when things slowed down and there was churn. It was usually my fault. It was because there were some hard, you know, one-way door type decisions on my desk. And, you know, maybe every year I would sit down and I'd 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. I was someone who always valued optionality. I think there's a massive tax in optionality when you can move this fast and try a lot of things. So, I do think the job's changing a lot.
Yeah. And there's so many reasons this is happening. One is just technology is just like every week there's a new shift in what is possible. So, if you're spending all these months thinking and planning, just like what a waste of time it ends up being, because so much is changing.
I know. Yeah. It's hard to keep up.
Luckily, we got some sweet podcasts to check out to keep up to date with what's happening. We'll link to yours, of course.
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Let's talk Halliganisms. Essentially, these are nuggets of wisdom and advice that you find yourself sharing often. You've written about a bunch of these online. And so let me just go through them and then just share kind of the synopsis of the advice and the lesson around this Halliganism. The first is: when you have to eat a sandwich, don't nibble.
Okay, completely stole this from Ruth Porat, the CFO of Google. I saw her quote somewhere. I'm like, that's it. She's put a perfect thing on it. And I'll give you an example where I think this will play out over the next couple years. I think within the next couple years there'll be a real retrenchment in valuations, and some will live up to valuations, a lot won't. And like if I look at the public markets, they're very tight right now. It's like the anti-bubble. I look at private valuations, it's like a real bubble. I think there's a reckoning somewhere down the road and a lot of companies are going to have to do layoffs. A lot.
It's never fun. It's usually the worst thing in the history of your life. And the temptation is to do, well, just do a little one now and we'll grow into it, and then do another, and then they do another one in six months and then another one. I think with everything, including this type of thing, is just rip the darn band-aid off. Tell everyone the bad news. They're adults. They can handle it, and get it done. And I think people avoid that. I think that's good advice Ruth Porat's giving because you're going to have bad news to deliver. Bad shit's going to happen to your company. Even if it looks like it's going amazing right now, weird stuff's going to happen and you're gonna have to deal with it. And we had a lot of weird stuff happen at HubSpot.
And there's a basketball coach named Mike Krzyzewski. 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 sidelines, "Next play. Next play." And what's going on there is when a college basketball player is playing in the game and takes a shot and clanks it off the rim and misses it, they have a strong tendency to go play overly aggressively on defense in the back court, and many times compound their error by making a foul or something like that. And what he wants is people to make their error, forget about it, and move back down the other side of the court and run the play.
And so there were actually times in HubSpot's history where we had Mike Krzyzewski's face on a huge slide in front of the company meeting saying "next play," because there was an unforced error and we need to deal with it and kind of move on.
Is there a story of that that comes to mind that is interesting and worth getting into?
There's a lot of them, but I remember it was the last day of March in 2019, and we had a really bad outage, like all day. And we never really had one of those. And 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 play slide on that one.
We made a lot of mistakes at HubSpot. A lot of bad things happen to companies and most of them are self-inflicted, and a lot of them are the old saw, like, companies are far more likely to die of overeating than indigestion. Usually it was trying to do too much.
I haven't heard that version. I've always heard most companies die of suicide versus homicide. Indigestion too. [laughter] Oh man. Okay. So, next Halliganism: never waste a good crisis. This is something that people hear. I'm curious, just kind of, what's the lesson here? And then is there an example of this where you learned those lessons?
I'll just follow on to... most of the good things that happened at HubSpot came out of a crisis, because we would take, you know, pretty drastic measures to fix it and make sure we didn't do the same thing again. And so in this particular case, we really rethought how we deployed software, how we thought about making software, in a way that was incredibly healthy. And I mean, we haven't had a serious outage since. The quality is much better.
And kind of an interesting thing with HubSpot is we started as a marketing software company, and Salesforce kind of came into our market, we pivoted into CRM. And if your marketing software goes down, like if there's a bug in the workflows or something like that, it's bad, but you survive it, you wait a little bit. If your CRM goes down, particularly the last day of the quarter, you're really impacting your customers' ability to do business. So that was like a mindset shift that we hadn't quite come to terms with, of how important we were to our customers. And so we made a lot of changes based on that crisis. You know, usually very good things came out of crisis.
So there's a lesson there. Something's going wrong. Is it just like overcorrect? Like use this as a way to...
We always overcorrected. Yeah. We purposely swung the pendulum hard the other way.
Which connects to the first Halliganism of if you're eating a sandwich, don't nibble. It's almost like go all the way, go even further.
Yes. Make it really obvious to everyone what's going on.
Okay. Another Halliganism: if you want to kill a plant, have two people water it.
I love this one. It's very true. Let's say, Lenny, you bought a new beautiful plant for your office and then you went away for a month to Turks and Caicos because your AI agent's doing your podcast, and you asked two of your friends, hey, would you mind watering my plant? And one of two outcomes would happen to the plant. The plant would either be overwatered and die or not watered at all and die.
And every CEO in the adults table has gone through this and they are religious about the DRI. Like everyone talks about DRI in the kids table, but once it gets to the adults table, people get deep religion on it. And I think it makes sense. Like when you're small and you're in startup mode, everyone's in the room, everyone knows exactly what's going on. So let's say you're running a pilot project with a big account. You're running that pilot project, everyone's on the same page, a salesperson, a service person, developer, everyone's on the same page, and you go out and do it. You execute well.
When you get to scale, you get a sales organization, you've got your forward deployed engineer organization, you've got your product management organization, you got some developers working on it. Everyone's kind of separate. No one knows really what's going on in the other departments. And so, let's say you want to really have a good pilot process. You want to rethink it because you're scaling. Everything important happens cross-functionally inside a company at scale, and you need someone powerful to own it. So let's say it's a salesperson. They need the power to tell people in other divisions what to do, even if they don't own it. So almost every CEO I deal with is like a zealot on the DRI idea. And it doesn't bite you 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 it may feel like, okay, we have two people on this, it'll be awesome, they'll work together. Your advice here is that doesn't work.
Committees never work. Yes. DRI is directly responsible individual.
The way I always thought about this is just having someone's ass on the line for something makes them so motivated to get it done, versus spreading, you know, the responsibility and the upside and the downside. It just doesn't work.
I totally agree with you.
Awesome. Okay. Another Halliganism. 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. It just takes a lot of lead bullets to get something done. I think the way you wrote about it is it's always like one step forward, two steps back. Talk about your advice there.
Yeah, I always thought incorrectly that we would have one hire or one investor or one event or one product release that would be a silver bullet. I was wrong about this. And the reality inside the HubSpot machine, the way it felt to me, it looks from the outside like over a long time up and to the right and smooth, but inside it was two steps forward, one step back, two steps forward, one step back, two steps forward, one step back. And a lot of times it was a crisis that caused that step back. So we just didn't have that.
And the thing about being a founder CEO is there's no one, especially when you're in your 20s, there's no one there to rescue you. Your parents aren't going to rescue you. Your VC is not going to rescue you. Your teacher, your thesis advisor. You're kind of on your own and you got to figure it out. And that kind of hits you when you hit your first crisis. Like, it's on you. You can get some help, but it's on you.
Sometimes they have you in their corner if they're lucky, at Sequoia. Plug.
I can oftentimes be the shoulder they cry on and I can give them advice, but it's still on them.
Do you feel like too many people start companies? Like when someone comes to you like, "Hey, Brian, should I start a company on this idea?" Do you often just like...
No, you have no idea what you're getting into. This is going to be much more painful. I heard Jensen Huang say that, like, I wouldn't start Nvidia if I had it to do over. [laughter] If someone asked me that question, I would start HubSpot over. It was very hard. There were a lot of sacrifices. It wasn't glamorous at all. But at the end of the day I'm incredibly proud of it, and you know, on my death bed I'm going to look
back and be and really enjoy it. And the Dalai Lama's got a good expression, like live a good life so you can live it again on your deathbed. And I'm really glad I did it. But I do talk a lot of founders out of it. Like the obsession is real. You have to be deeply obsessed. And all these founders and CEOs I talk to, I mean people talk about 996. It's way more than that. I mean the founders are seven days a week. They're always on. I get texts from them on Sunday nights.
It's full contact. And I think what's going on there, particularly now, is people just see this massive platform change, massive opportunity. They don't want to waste the opportunity. So, I think that mindset's right. But people today are much more hardcore than they were in my era. Like, I worked hard. I was 60 to 70 hours a week for the entire time. Never really turned it off, but that's kind of how I thought about it. It's different now. People are much more focused. And I think Elon's inspired people like
I had a startup back in the day and nowhere near as successful as HubSpot. But the way I thought about it is let me just give it everything I have and see what I can do. This is my shot. This is my chance. Let me just give it all, like forget balance. Just go for it seven days a week for a while. You know, then you scale back. And it's just such an empowering thing to do for a while. Just like let me just try. I'll give it my all, this won't be forever.
Yeah.
And I know you've written about this, just like balance for CEOs is not... you should not have work-life balance if you want to be incredibly successful. I don't know if that's always true, but how do you talk about that to founders?
I don't know any of the founders I work with that have work-life balance. By the way, this is not something I recommend. I didn't have it. I don't think my co-founder Dharmesh had it. The only CEO I know, and he's unusual in this way, is Kareem from Clay. He's like, "Nope, you need balance. Take the weekends." Like, he's got a different mindset. I'm going to have him on my pod to talk about his mindset, but he's sort of the outlier. Everyone else is really, really obsessed and they really don't have much of a life.
It did take them a long time to find product market fit. We're definitely pre-AI. [laughter]
Wonder if there's a correlation, but it did work out. So,
Great.
So, it is a good lesson. Okay. A few more here. One is a math formula. EV is greater than TV is greater than me. What is that?
Okay. EV is enterprise value. TV is your team's value. Me is your value. And as HubSpot was scaling and we had a lot of people who were VPs in different roles and they started to get good-sized organizations, where they would fall down was they didn't solve for me, but they'd solve for TV over EV. It's all for their own team. So let's say they ran sales and say, I just want bookings to be as high as possible because I get paid on bookings, and the service team can handle all the downstream problems I created. Marketing to sales, between every department this happened, and the kind of immature managers who didn't scale really solved for themselves, and as they solved for themselves, kind of suboptimized for their peers, and their employees would notice it and complain about it. It would be fine in the short term, but it would show up.
And the place it would show up, Lenny, was we did, and I think a lot of companies do this now, but we did a quarterly customer net promoter survey and a quarterly employee one. And we would have people rate it by the department they're in. So it's like sales and service and engineering, all the different departments. And we had an overall net promoter score, and then each department had a net promoter score. And let's just take sales. Sales net promoter score was like 65, 62, 68, 30. Ooh, that's a big drop. And then you read the comments and it was not good. A lot of complaints about the leader of that. And a lot of the complaints were a little bit of this TV thing. And then we'd give feedback to that VP, would help them. We'd give them all the comments, be like, you got this. And then a quarter later, from 30 to negative five. They almost never actually recovered. When you lose your team, it's hard to get them back. And that's why I say, you know, hire slow, fire fast.
And this doesn't show up in the first 100, 150 employees. Everyone's solving for EV, but as it gets bigger and the CEO doesn't know anyone and there's a couple layers between you and the employees, they tend to solve for TV. So, we always put on the wall, solve for EV over TV over MV, and then we added CV in front of EV. Solve for the customers first, then for HubSpot, then the employee, then yourself. That was very helpful to us.
Yeah. I imagine everybody listening working at a big company understands this, where you have goals, you get your KPIs, and your performance reviews are based on what impact you drive, if you hit your goals. And so, you know, the incentives are focus on my goals and drive those, and I don't care about other people's goals, the company's goals.
Steve Jobs had an interesting line. He says, you don't work for your boss, you work for Apple. I thought that was pretty good. I heard that after I was CEO of HubSpot, but that kind of captures the sentiment. And that's how I felt about HubSpot. You work for HubSpot first and then you work for your boss.
This is hard because, you know, people's performance reviews are based on their goals, KPIs. It's always like, here's what I got to drive. Other than putting posters on the wall, and this is our, just, HubSpot growth above all is what matters, or customers I guess in your case, is there anything tactically that was useful in helping people prioritize enterprise value?
This was explicitly called out in the form for the employee. You know, when you got your review, this was part of it. And so they'd get a score of one to, I forget, 10 on that. I would talk about it constantly. And when we first started HubSpot, I ran it a little bit like Jensen runs Nvidia, where I didn't do one-on-ones and I gave a lot of good and bad feedback publicly in large management team meetings, and I definitely would go out of my way to criticize people if I felt like they were solving for TV over EV, and people got a sense for that. And then every quarter we did a really well-produced company meeting. We spent a lot of time on it, and at the end of the company meeting we gave out, we called them the champagne awards, a bottle of Veuve that my co-founder and I signed, and we'd read something nice about them and give it to them. And usually there was an EV team in that. And so we did different things to kind of beat that into people's heads.
Amazing. So here it's just celebrate people that focus on this and also include it in their evaluation, performance reviews.
Yeah.
Okay. That's a good segue to another Halliganism, where you talk about how companies are either customer-centric, employee-centric, or investor-centric, and it's really important to know which you are, and you guys actually shifted there. What's your insight there?
We were very employee-centric, more than customer-centric, in the first several years of HubSpot. So much so that the company was number one on Glassdoor's best place to work. I was the number one CEO on Glassdoor. And as I look back at that, I'm not sure that's a good thing. Like wanting to be liked, I don't think is a good feature of a CEO. And wanting to be the best place to work probably isn't the right way to go. Like if you look at Tobi from Shopify, his scores aren't that good, but that company's doing really, really well. And so we overindexed on it. And part of the reason we overindexed on it is my co-founder was really strong in this, and we had an incredibly powerful head of HR named Katie Burke, and we just worked on it. We spent a lot of time on it. And when we'd have a management team meeting, and let's say it's four hours long, two of the four hours would be on employee stuff.
And at some point I was like, why are we spending so much time on employee net promoter scores? Like let's say our employee net promoter score was 60 and our customer net promoter score is like 25. I was like, I would give up 10 points of employee net promoter score to get 10 points of customer net promoter score. And so over some time we shifted the center of gravity to customers. We still of course worried about employees, but the center of gravity at HubSpot moved very much to customers.
And we did that in a few ways. Like every time we had a management team meeting, our management team meets once a month, not once a week, we would have a customer panel come on, and I would run the panel and ask very tricky questions to the customers and pull out the bad news from that. And we still do this, we have a customer panel at our board meetings. Our whole board can ask questions, and my favorite question is what do you love about HubSpot, and then what do you hate about HubSpot? And they kind of look at their shoes and you're like, come on. [laughter] And it's a great way. So the employees hear those voices. At company meetings, we had the customers in the company meetings. We changed the comp plan, so the management team got paid not on revenue but on retention and net promoter score. And so we worked very hard and kind of swung the pendulum to customer-centric. But I do think companies have one center of gravity or another.
There's a really interesting thread throughout this conversation of just, when you want to change how you operate, you have to go really far to a whole other side and almost overcorrect. It's really interesting 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've got to say the same thing over and over and over and over and over again. It just doesn't sink into people's heads. You have to just be incredibly repetitive on it before it sinks in. Same thing with marketing, but internally that happens.
The other weird thing about being a CEO, Lenny, is as it gets bigger, like when it's small, you're all on the same level, but as it gets bigger, you didn't interview everyone. With thousands of employees, you don't know everyone, and people put you on a pedestal that you don't deserve. And let's say you're in the hallway and you're just kind of shooting the breeze with a bunch of people and you're like, "Ah, it'd be cool if we had a product that did..." somebody inevitably would go home and build that thing and be like, Brian wants this. This is a big initiative. So people really lock in on what you say. And it turns out you have to be very repetitive and you have to be very careful what you say.
Dharmesh was on the podcast, your illustrious co-founder, and he developed a whole system to avoid this sort of thing. Flash tags, or it's like, this is just an FYI. We had a whole system, because we would say something on an email to the management team or Slack and everyone would be like, okay, this is what they want, let's do it. And sometimes it is like, you need to do this, and sometimes it is like, we should talk about doing this, and sometimes it is, this is just kind of an FYI, we're thinking about it. And because it got big, we came up with that rubric. We needed to tag each email with: do you want me to get this done this week, or is this something we should talk about, or is this something that's just FYI, I'm thinking about it.
It was like, one of them is plea: I'm not telling you to do this, I'm just pleading that you do what I ask. [laughter] Oh man. Okay. This all connects. And by the way, you guys were co-founders for 20 years. You shared something before we started recording. So Dharmesh famously did not ever want direct reports. He's just like, "Brian, I want to start this with you, but I don't want to ever manage anyone." And you were talking about how you had to take on engineering, which didn't make any sense.
Well, I'm an engineer and I can code, but it's not good. And so when we started the company, he's like, "I was a CEO before. I was terrible at it. I don't want to do it again. You're going to be the CEO." I'm like, "Great." And he's like, "And by the way, I'm not going to have any direct reports." I'm like, "Well, it's just the two 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're starting to hire engineers and onboard them and make our big decisions. And I would go to him and be like, "Well, can you manage them?" He's like, "Don't you remember I told you I won't have any direct reports?" I'm like, "Surely you were kidding when you said that." He said, "Nope." So, Dharmesh Shah has never had a single direct report at HubSpot.
Incredible. It's just like a dream way to operate. I love that you made it possible for him, and it created all this opportunity for him to tinker. Yes.
It's a free mind to really think and be creative.
Yeah. I'm excited to get him back on the podcast someday. We're going to link to that episode. Maybe a last question, and I'm curious if there's anything else you think we missed. As a company grows and scales, the job of a CEO changes. You've written a bit about this, of just how different the job is when you're a startup versus a scaleup. What are some of the things that most change, where your time goes as a CEO as the company grows?
We clicked on this earlier, but that inspiration thing. I have a little rubric where in the startup phase, it's 90% perspiration, 10% inspiration. You get to the scale-up phase, it's 90% inspiration, 10% perspiration. And you're doing every job in a startup, and over time 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 have trust issues. Like I only trusted a small number of people at HubSpot to be a DRI, to really drive something important. That drove people crazy, that I didn't have a larger trust surface. Every one of the CEOs I work with has the same problem. And that's a scaling limit. That was a limit for me. I wasn't trusting enough.
Brian, I feel like I could chat with you for hours. There's a whole list of Halliganisms I'm going to link to that we didn't even touch on. But before we get to our very exciting lightning round, is there anything else that you think we should chat about? Anything you want to leave listeners with?
Well, I would say if you're a CEO and you're interested in scaling, I think the Halliganisms post is all the mistakes I made in my 15 years being CEO. I tried to summarize them in there to help you avoid them. And I have a pod. You should first listen to Lenny's pod because it's amazing. But I have a pod just for CEOs called Long Strange Trip, where I interview CEOs about this. So Lenny's interviewing me about being a CEO; I get to interview other people about being a CEO. I'm kind of a CEO geek these days.
And the name of the podcast is a Grateful Dead reference, which we haven't touched on, but you're a huge Deadhead, as they say.
That could be a whole other podcast conversation. I think there should be, actually, because I wrote a book called Marketing Lessons from the Grateful Dead, and there's so much. The Grateful Dead were like the ultimate Silicon Valley startup. They started in 1964. Do you know where they started, Lenny?
No.
Palo Alto. Their early concerts were at Stanford, all over Silicon Valley. They're a Silicon Valley company. They were very first principles in their thinking. They
created a new category, a new way to distribute their music. They disintermediated the ticketing companies, very innovative. Steve Jobs and Jerry Garcia are very similar in my mind, real craft people. So, I think of them as a great Silicon Valley success story.
You said you had a whole book about this. What's the book called? Just in case people want to dig in.
Marketing Lessons from the Grateful Dead.
Amazing. And I read that you bought Jerry Garcia's guitar for a large sum at some point.
Yes, I did. And I consider myself the steward of his guitar.
It gets played, like Dead & Company played it. And there's a million Grateful Dead cover bands that let them play it, but I'm taking care of it for the Deadheads.
What's one nugget of wisdom or lesson that people can take away from The Grateful Dead for startups?
Okay, people talk about spiky teams. The Grateful Dead team was interesting. Garcia himself was a bluegrass guy. He was a banjo player. And then Bob Weir, who recently passed, was kind of a country crooner, like country music. Then their bass player was an avant-garde jazz trombonist, Phil Lesh. And their keyboard player was a guy named Ron McKernan, Pigpen. And he was like a harmonica guy. And the drummer was like a marching band drummer. And so the spikiest of spiky teams came together and made a new genre. They created a new category of music. It wasn't rock and roll. It wasn't sort of the Rolling Stones. It wasn't Buddy Holly. It was like this new thing. And then they called it a jam band, because they played rock and roll in a bluesy, open, organic, kind of jazzy way. And so spiky teams in creating categories, underrated.
Incredible. Are you one of these people that have been to like 100 Grateful Dead concerts? Okay.
Makes sense. Okay, this could be a whole podcast, but we're going to move along. Okay. With that, we've reached our very exciting lightning round. Brian, are you ready?
Let's do this.
Fired up. I've watched you do the lightning round so many times.
I'm flattered. Unsurprising questions. What are two or three books that you find yourself recommending most to other people?
I haven't read a book in a long time. I listen to podcasts. I'm on X. I talk 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 Marc Andreessen on recently, and I don't know if you've heard his whole thing on what he consumes. He talks about how he has a very barbell strategy to media. It's either Twitter or books that are 10 years or older, and nothing else.
I've heard him say that. Yeah. I kind of stopped reading. I was getting ready for this, Lenny, and I was like, I can't remember the last book I read.
I think this is going to make a lot of people that don't read books feel better. Like, all right, this is okay. Favorite recent movie or TV show you really enjoyed?
I love the new Ken Burns. Very long, very good Revolutionary War documentary. He's a craftsperson. It's exceptionally well done. And what I like about it is America is really like a disruptor startup. There are so many startup lessons from those early years. They were gutsy. Talk about two steps forward, one step back. They got into the details of how George Washington ran the army. We were very close to losing that war most of the time. And it was two steps forward, 10 steps back. Two steps forward, 10 steps back.
Lots of lead bullets. A lot. And unless we had alliances, like we had alliances with the French, we were screwed. So I love that. It's a long one, but it's really good.
How long is this? What are we getting into?
Probably 10 plus hours.
10 plus hours. It's a lot. But worth it, is what I'm hearing.
I'm in Boston. You know, it's revolutionary, surrounded by history.
All right. Favorite product you recently discovered that you really love?
I love my Delphi clone. I teach a course called Scaling Entrepreneurial Ventures, and I don't do office hours. I have Delphi do my office hours. Very happy with that.
My favorite feature of Delphi, and again, lennybot.com, there's my Delphi, we both have little bots. The voice feature is the coolest thing. Just great. I had video, they got rid of it, they're going to bring it back. Can't wait till it has video. My least favorite, my lowest NPS product, is my Sonos system. You have Sonos?
I do. And I get you.
Yes. Painful.
Yeah. It's so good in so many ways and so annoying in so many ways. So annoying.
But we still use it, you know? There's nothing better.
There's not a competitor. You and I should start a Sonos competitor.
No, we should not. That's a bad idea. I'm not doing this. And just to be clear what these bots are, just so people understand how cool this is: every single podcast like this one is going to be sucked into it, and every single newsletter, and you just talk to it and ask it, like, how do I find product-market fit, and it's based on everything I've ever shared. Here's your steps.
Okay. What's even better about it is, 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 lectures in there, and there's a new feature where it asks you questions and it kind of interviews you, and so it's pretty proprietary. It's getting better. I like it a lot. Yeah.
To that point, I haven't 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, let's not tell too many people that, because one day I'm going to paywall it in the near future. Anyway, enough about that. lennybot.com. Do you have a favorite life motto that you find yourself coming back to in work or in life?
This isn't lightning, but four years ago, I had a very bad snowmobile accident. Drove a snowmobile off a cliff. The snowmobile smashed into a million pieces at the bottom of the cliff. So did I. And I laid at the bottom of that cliff for a while. I was unconscious for a long time. Woke up, and I didn't think I had my phone. So, I sat there for a long time like, I'm probably going to die tonight. No one knows where I am. It's frigid out. It's in Vermont, and I'm going to freeze to death. And I was sitting there for a couple hours. I finally was like, "Oh, I do have my phone." Dialed 911. By the way, 911, amazing service. And so, the helicopters came in, took me out, took me to the hospital, and lots of surgeries. And I was kind of out of commission for a year. And you can't see it, but I got metal all over me, all in me. Life's short, like, life's short. And I made some decisions at the bottom of that cliff. One of the decisions I made at the bottom of that cliff was, I don't really like being CEO of an 8,000-person company. Doesn't really suit me. My harmonic motion is off. I don't love the day-to-day. If I make it out of here alive, I'm out. And so that's exactly what happened. The first big thing that happened coming out of that was I gave the job to Yamini, who's still the CEO, doing a great job. So life's short. Don't waste it.
I've heard the story, but it's just as powerful hearing it again. Why do you think it takes a moment like that to have someone realize, I need a change, you know?
I think people think they're going to live forever, and they're not. As somebody who's 58, yeah, life's very short, and I'm much more intentional about the decisions I make, much more intentional about the people I hang out with today than I was before that. And I really try to work on things that bring me joy,
like this pod.
Same. I appreciate it.
Same. I read that you had 20 broken bones in this accident.
Lot of broken bones. A lot of metal.
I got 33 screws in me. One loose one up here, Lenny.
Same. Okay. Last question. We talked a bit about the Red Sox. You're a part owner of the Boston Red Sox. What's something that would surprise people about how a baseball team is run, or just what it's like on the inside of a team like the Red Sox?
It's not as profitable as people think. People think these rich guys come in and buy these teams, but the way the league is set up and the way the economics are set up, it's not a profitable endeavor. Whereas other leagues are much, much more profitable. 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, with like a $400 million payroll, and the Miami Marlins are like a $100 million payroll. And in other leagues, that all kind of balances out pretty well. Baseball is set up incorrectly. I think it'll correct in the next couple years, but it's kind of a broken model.
Intriguing. Stay in AI SaaS if you want to make money, is what I'm hearing. Vertical SaaS. Brian, this was incredible. We covered almost everything I was hoping to cover. Two final questions. Where can folks find you online if they want to reach out? Where do they find the bot? How do they work with you if they wanted to, or do they have to be a Sequoia founder? And then, how can listeners be useful to you?
I think there's two things. I would love folks to listen to Long Strange Trip, my pod. I get some comments, but not a ton. Lenny, you have more comments than me. I'm jealous. I'd like just feedback on how I'm doing. It's very new, it just started a couple months ago. It seems like it's going pretty well, but it's my family and Sequoia people giving me feedback. I'd like to see what all of you think about it. So that would be spectacular.
All right. So hop on YouTube and leave some comments about what you think. The real, honest feedback.
Okay, here it comes. Brian, thank you so much for doing this.
Appreciate you. Appreciate you. Thank you.
Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
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