Brian Halligan: Building HubSpot into a Multi-Billion Dollar Company

From Cambridge startup to NYSE heavyweight, HubSpot co-founder Brian Halligan reveals the sophisticated frameworks behind scaling a $30B enterprise. Now a Sequoia Capital Senior Advisor, Halligan shares rare insights into the nuanced decisions that separate exceptional companies from merely successful ones. Learn the strategic principles of modern company building, including the counterintuitive culture choices, talent algorithms, and leadership pivots that defined HubSpot's trajectory. A masterclass in scaling excellence from startup to global enterprise. Timestamps: (00:00) Intro (02:36) Halligan's life-changing snowmobile accident (09:38) Shane's life-changing medical mystery (14:38) The different phases a CEO goes through while growing companies (20:44) Lessons learned from Steve Jobs (23:18) How to hire and fire people (and when) (27:55) The problems with "Best Practices" in business (31:11) The most underrated public CEOs (and why Jerry Garcia from The Grateful Dead is on this list) (43:38) The history and future of inbound marketing (51:08) On decision making (55:18) On work-life balance (58:28) On success Newsletter The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at https://fs.blog/newsletter/ Upgrade If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠https://fs.blog/membership/⁠⁠ and get your own private feed. Follow Me: Instagram: https://www.instagram.com/farnamstreet Linkedin: https://www.linkedin.com/in/shane-parrish-050a2183/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  If I put 10 calories and try to improve the feature, I get like a thousand now. And so I more paid attention to the features and tried to get better at the features. And this took me a while to figure this out. And over time, just tried to hire people around my weaknesses. And I have plenty of them. I really looked at hiring the best I could in the areas where I was weak, rather than trying to become an expert at it. And I'll give you one area. And for years, I was convinced I was a great product designer. I'm not. I just don't have that genetic code. I was actually quite bad at it. It took a while before that feedback sort of hit me between the eyes. We started hiring people really good at it and enabling me to let go of it.

• 0:47Shane Parrish?

  Welcome to The Knowledge Project. I'm your host, Shane Parrish. In a world where knowledge is power, this podcast is your toolkit for mastering the best of what other people have already figured out. If you're listening to this, it means you're not a supporting member. Members get early access to episodes, my personal reflections at the end of episodes, which a lot of people say is quickly becoming their favorite part, no ads, exclusive content, hand-edited transcripts, and so much more. Check out the link in the show notes for more information. My guest today is Brian Halligan. Brian reshaped the way that we think about marketing, sales, and customer service. With his co-founding of HubSpot in 2006, he pioneered the concept of inbound marketing,

• 1:29Shane Parrish?

  emphasizing the importance of creating valuable content to attract customers naturally. Under his leadership, HubSpot has grown from a startup to a publicly traded company and a global leader in the industry, empowering millions of businesses to grow better. I first met Brian at a Sequoia conference where we both spoke. In the conversation, we talk about the phases of a CEO from startup to IPO, and how the skills change, why interviews are a terrible predictor of on-the-job success, and what you can do about it, why hiring panels are flawed. What changed after his near-death experience? Why Jerry Garcia from The Grateful Dead is one of the most underrated CEOs? And what you can learn from him? Why consensus is the enemy of scale?

• 2:14Shane Parrish?

  Why you need to have winners and losers? What he learned from Steve Jobs? And of course, the future of inbound marketing? It's time to listen and learn.

• 2:36Shane Parrish?

  Brian, I want to start with the role of a CEO and the journey from startup to scale up to public company.

• 2:44Speaker 00

  It's a remarkable journey. And I was on that journey for about 17 years. And a couple of years ago,

• 2:53Speaker 00

  I stepped out of that journey, Shane, in a relatively dramatic way. And you may have heard this story before. I was snowmobiling up in Vermont. And I was taking a snowmobile from Rage Water, Vermont to Woodstock, Vermont, coming to the hairy part of the trail.

• 3:14Speaker 00

  And went up over a lip. And went down on the other side and just completely lost gravity, went straight down off a cliff and smashed at the bottom. The snowmobile was in about a million little pieces. I was passed out for a long time.

• 3:33Speaker 00

  And then I woke up. It was about four in the afternoon.

• 3:39Speaker 00

  It was quite cold and nobody knew where I was. Confident I was going to die. And I sat there for a good hour thinking about, you know, if I do make it through, then what?

• 3:51Speaker 00

  And I never bring my phone when I snowmobile because in Vermont, there's no signal. The whole darn state, there's no signal. But an hour in, I'm like, maybe I'm on it. It turns out I brought it like a moron. And I checked it and dialed 911. Shane, have you ever dialed 911?

• 4:07Shane Parrish?

  I have, yeah.

• 4:08Speaker 00

  It's an amazing service. If that was a startup, I would be thrilled to invest in it. It's amazing.

• 4:15Speaker 00

  The woman was sort of very, very good. And she said, I remember she said, "Sit tight." And mind you, I have.

• 4:24Speaker 00

  I'm a mess, many, many, many broken bones. And so it's like, yeah, I'm not going anywhere. And then she called the two local fire stations and they're volunteer and there's no one there. And so then she has to track down the mobile phone numbers of all the firefighters and the rescue people. Calls them at home, they hop in their snowmobiles and they come and find me. By the time they found me, you know, it's pitch black, it's really cold out. And they said they went to work on me and kind of put Humpty Dumpty kind of back together on the side of the mountain. Toed me to a flat area, which is a few miles away. Helicoptered me to Dartmouth University. And there they really put Humpty Dumpty back together over lots of surgeries, a lot of time.

• 5:09Speaker 00

  And I remember that because that was the end of my CEO journey. I had been quietly saying to myself that I didn't love being CEO of a spot frustrated with just the core work. And I remember saying to myself at the bottom of that cliff. I make it out, I'm not coming back. And so I was out of work, a terrific woman took over for me. It's kind of a funny story about that while I was gone. And as I got back on my feet, everyone just assumed I was coming back. It's like, no, no, no, I'm not coming back. You're doing a great job. You got this. And I actually think a lot of CEOs would be a lot happier if they did something similar like that. Not the snowmobile part.

• 5:52Shane Parrish?

  I assumed, yeah. What went through your head when you, you sort of couldn't move, you're stuck in the snow? And you couldn't contact anybody like what, what are the thoughts that were going through your mind?

• 6:03Speaker 00

  I'm not super comfortable telling everyone all my thoughts on this, but a lot of thoughts around if I make it out of this somehow, someone finds me randomly. What's going to change? But then, I mean, the net net of all of them is life can be very short, very short. You never know what will happen. And don't waste it. Don't waste time doing something that doesn't make sense for you. You know, refactor your life and I refactored my personal life and I refactored my professional life pretty dramatically. And these days I really don't do anything I want to do. And I wanted to do this podcast. It's a really good podcast.

• 6:47Shane Parrish?

  Thank you. Tell me about what the changes were. Like, were they all at once? Were they slow? Like, be specific about sort of, I always wonder this because I had a near-death experience too, a couple of years ago. And I remember pondering life and thinking about, oh man, if this is the end, like, did I spend the time the way that I wanted to? And if it's not the end, like, what is it that I really want to change in life? And what impact will that have? And I've done such a better job of sort of taking care of my body and my mind and sort of self-care, if you will, just as a big word to encapsulate that. I changed a lot of relationships in my life. I sort of invested in

• 7:31Shane Parrish?

  some and then I wouldn't say broke off some, but definitely stopped investing in some. And so I'd love to hear about the specific things that you did that you sort of were like, okay, well, this is, this is the realization.

• 7:45Speaker 00

  It's exactly like that. When I say refactor relationships, I triple down on family relationships. I wouldn't say ended relationships, but I certain people that didn't give me energy in certain ways and just stopped engaging with. And it's a much smaller group I engage with these days. Professionally, I stopped my main job. I mean, I founded HubSpot 17 years earlier. It was kind of my life and everything was sort of wrapped up in it. And now chairperson, so I'm still involved, but not in the day to day. I got obsessed with, maybe similar to you, with longevity. Like, well,

• 8:24Speaker 00

  if I'm gonna live to 85, 90, I want to be very strong living to 85, 90. So basically, anything Peter Attia or Andrew Huberman said to do, I did, except they drink a little. But I basically do everything they do. Lost a lot of weight, got much better shape. And so lots and lots and lots of changes. But I think the macro one was just. Love your family. Tell your mom you love her. Hug your kids one more time today and don't waste time. Do things that really are rewarding to you.

• 8:55Shane Parrish?

  One of the big things for me was like just being home for the kids every day after school. I just made a commitment. I was like, I'm gonna be here every day when they get home. I'm not gonna push it at the office a little longer. I'll find other ways to do that because I'm also sort of balancing ambition and all this other stuff, but it wasn't gonna come at the expense of that time with them that I know inevitably I'll look back on and be like, man, I just wish for, you know, a little bit more cookies and milk.

• 9:20Speaker 00

  They say the dying wish of every man, they just want another day. And I think about that a lot. Like, what am I going to wish I had not been in my life? So Sheen, while we're on this, why don't you tell us what happened to you?

• 9:32Shane Parrish?

  I didn't know for a long time what was happening to me. I just had symptoms and they kept getting worse and worse and worse. And so like, I had a fever, then I had an earache. And this was during COVID, so everybody thought it was COVID. So I went to the doctor and they were like, oh, you don't have an ear infection, you're fine. You don't have COVID, go home, suck it up. And then I woke up on a Saturday and I remember just making a latte and then I was drinking it and it spilled down my chest.

• 10:00Speaker 00

  Okay.

• 10:01Shane Parrish?

  And I was like, what the heck? I've been drinking out of cups since I was like two, you know, rarely do I spill something. And I went, I went to the bathroom and I looked in the mirror and the left side of my face was 100% paralyzed.

• 10:16Speaker 00

  Yeah.

• 10:17Shane Parrish?

  And so I had no movement whatsoever. I felt like I was moving things, but like if I raise my eyebrows, like you can see now on YouTube, if I raise my eyebrows, this, it was actually kind of beautiful in hindsight. It was freaky when it was happening because this, and it just didn't move. And I was like, oh God, like I gotta go to the doctor. My first thought was actually not to go to the hospital, which is a little weird. So I show up at my former family doctor's office on the weekend and they're like, you need an appointment, it's Saturday. And I was like, well, I can't move my face. So I think that qualifies as like, maybe I get an appointment today. And she's like, oh my God, yes, you see the doctor right away. I go into the doctor and she's like, I think you're having a heart attack.

• 11:00Shane Parrish?

  And I was like, well, this doesn't make a ton of sense, right? Like, maybe, I don't think that's the case. However, you're the doctor. I don't know what I'm talking about. And she's like, you need to drive to the hospital. I was like, well, if you think I'm having a heart attack, why are you telling me to drive to the hospital?

• 11:16Speaker 00

  Yeah.

• 11:17Shane Parrish?

  It's like, these two things don't align. Anyway, I go to the hospital. I see a doctor right away. I mean, for all of the knocks on Canada's healthcare system, there's certain things in triage that they, they definitely see. I saw a doctor probably within three minutes of getting to the hospital. And, you know, he's like, you're not having a heart attack. I was like, thanks. And then it's like, go sit and wait for like 12 hours. Well, we handle all the other urgent people, which is fine. And so he sees me and he's like, I'm going to give you some Pragnozone and you'll be fine. And I remember going like, wait, what? Like, you're just going to give me some steroids and like, send me home? Like, nobody cares about how this happened. I'm a healthy, at the time, 42-year-old male. I'm not overweight, you know, I don't smoke, I don't excessively drink. I have nothing that would sort of indicate this.

• 12:01Shane Parrish?

  When I was in the waiting room for the 12 hours, I started talking to a whole bunch of neurologist friends. And they were like, you should get tested for these four things. And it was like HIV, Lyme disease, mono, and something else. And I was like, can I just get a requisition to get tested for this? And he's like, no, it's just like a waste of the medical system.

• 12:23Speaker 00

  Oh, man.

• 12:24Shane Parrish?

  And I was like, wait, what? Like, that doesn't make sense. He's like, go talk to your family doctor. They'll, they'll figure that out. I gotta go help other patients.

• 12:30Speaker 00

  What's your face at this point?

• 12:32Shane Parrish?

  Well, it's still paralyzed, right? So he's like, you're going to recover. He's like, you, you have a 99.8% chance of recovery. And I'm like, I'm not worried about recovery. I'm worried about what caused this. Right? Like, before we figure out the future, we have to figure out, like, what, am I doing something I need to stop? And I went to my doctor on Monday and I was like, hey, can I get a requisition for these blood tests? Which in, in the States, you just show up and do it. And in some provinces in Canada, you can just show up and do it too. But in Ontario, where I live, they won't allow you to do that. You need a requisition. Anyways, she says no, for whatever reason. She's like, if the ER doctor thought you needed it, he would have given it to you. You know, please, please fuck off politely is sort of what she said. And I was like, well, this is so weird. And I'm like, thinking about

• 13:16Shane Parrish?

  this. And then I wake up a few days later and I can't stand. Oh, man. So the backs of my knees, like if I'm moving, I'm fine. But if I stand still for like 10 seconds, I'm literally crying. There's tears coming out of my face. I've never been in so much pain. It's like somebody stabbed the back of my legs with a knife. And I was like, wow, this is like so crazy. And I'm like emailing my doctor again. And I'm like, I really think I should get tested for a whole bunch of stuff at this point. Like, I don't know what's happening. And she's like, slow knowing me. She's like, it'll get better. Just give it some time. And then like three or four days later, I wake up and I can't open my mouth. Hmm. Uh, like I have a lock jaw, basically. I can open it like a centimeter. And luckily, to cut a long story short, I end up talking to a close friend of mine who happens to be

• 14:01Shane Parrish?

  an eye surgeon. She's like, I'll give you the requisitions. She gives me the requisitions. I test positive for Lyme disease. I start the treatment for Lyme disease because when you test positive, you can actually, you can fix it. And so I start taking, I think it's doxycycline, the antibiotic, which is the treatment for that. And instant improvement. The cool part of this is I saw a neurologist in Ottawa who tested me for like 200 different things. You know, I went down to give blood and the lady's like, this is the maximum of blood we're allowed to take out of you. And I was like, oh, this does not sound really good. And I came back completely normal, aside from the Lyme disease. So I'm glad we caught it. Glad we solved it. You know, made a lot of changes after that.

• 14:45Speaker 02

  Hey, Bose here. On your next track, listen for the decisions. Distortion on the bass, the vocal right up front. Every choice deliberate. With Bose, you'll hear it all. Your music deserves Bose.

• 15:02Speaker 03

  This episode is brought to you by Michelob Ultra. Good times mean competitions between you and your friends. Like seeing who can throw some pigskin the farthest or rush the field the fastest. Winner gets an ultra because it's not just a superior like beer. It's also giving fans superior access to their favorite sporting events. Superior is worth playing for. Visit michelobultra.com/superioraccess to enter. Enjoy responsibly. Copyright 2026 Anheuser Busch InBev Michelob Ultra Beer, St. Louis, Missouri.

• 15:31Shane Parrish?

  I want to go back to you and HubSpot though. So like you've been on this journey for a long time from startup all the way to scale up to now public company sort of chairman. Walk me through the different phases a CEO goes through.

• 15:47Speaker 00

  I personally break them down like two to 20 employees, 20 to 200, 200 to 2,000, and then 2,000 plus. And I kind of grade myself in these seasons. Like I give myself a B in two to 20, like two to 20, I was doing customer development. I was the lead user of the product. I was marketing it, but I'm a crappy coder. And so the heavy lifting was really done by my co-founder. 20 to 200, I was kind of in my element. I loved it. I was an A. 200 to 2,000, maybe a B. And then 2,000 to 8,000, maybe a D. I really didn't like the work.

• 16:30Speaker 00

  And I think that's the case with a lot of CEOs and a lot of executives and a lot of people. Like people have a season that they enjoy and they get good at it. I think that's very much the case for me.

• 16:40Shane Parrish?

  Which was the one where you felt like you had to grow the most to fulfill the role?

• 16:46Speaker 00

  Really through the whole thing.

• 16:49Speaker 00

  I felt under qualifying to do it and.

• 16:53Speaker 00

  I don't know about you, but I still have imposter syndrome here on the podcast. And I had it throughout. I think one of my superpowers actually is I'm a learner and I try to get better. And I listen to other people and I take feedback pretty well. And we had a mechanism that was quite good for giving me feedback, really good, actually. My co-founder was responsible for my annual 363 review. He's super introverted, so he didn't want to go around and talk to other people. So he sent a net promoter survey out to the board, the execs, customers, a whole bunch of people, 30 different people. He got a lot of responses, maybe 25 responses. And there were two questions, Shane. One was, on a scale of one to 10, how likely do you refer Brian as CEO of HubSpot?

• 17:37Speaker 00

  And two, why did you give that answer? And people wrote novels about it. And it's hard for CEOs to get feedback, very hard. Very few people give straight feedback to the CEO. So this was a good way to get, the N was big enough that people gave very, very strong feedback. And he summarized, I gave you my net promoter score. And then I started reading my review and each page was different. So the first several pages were my features and he's a software developer. He's like, here's your features. So page number one, you're very good at explaining HubSpot's vision. And then he pulled out quotes from the novels people wrote. Page two, page one through 10 were features and they were great.

• 18:21Speaker 00

  And I was pretty confident that I was the best CEO ever invented after reading the first 10 pages.

• 18:26Shane Parrish?

  And then the bugs came.

• 18:28Speaker 00

  Page 11 was the bugs and there were 12 pages of bugs. And I was pretty convinced I was the worst CEO ever invented by the end of the 12 pages. And I remember when I finished it, I'm not a Scotch drinker, so I remember I poured a glass of Scotch. But that mechanism for getting feedback was...

• 18:48Speaker 00

  We still use it. So the current CEO gets the same type of thing and it's very, very, very useful. I think founder CEOs often have this problem that like founder CEOs like to make decisions, like to be involved with the details, like to drive things, like to be in the middle of things. And that's a great strength when you've got 10 people. But that great strength you have turns into your greatest weakness when you have a thousand people. You're trying to manage everything, trying to manage everything, know everything that's going on. And so the consistent feedback was like, how do you get yourself out of the details? How do you stop working in the business? How do you start working on the business? That was kind of a common thread that I worked on across all 17 years.

• 19:29Shane Parrish?

  Was that feedback enough for you to walk away going like, okay, I see this. People are giving me feedback. I accept it. There's some truth to this. Or was there a part of you that was like, no, they're wrong?

• 19:41Speaker 00

  It was pretty, it was pretty accurate and I'm shaking my head through most of it. In the software business, sometimes there's something that someone thinks is a bug, but it's a feature to somebody else. So some of my bugs I actually thought were features. Like I can be really passionate about something and Brian gets so passionate, it's like a little scary sometimes. I'm like, fine, if like two out of 30 of you think that and the rest think it's a good thing, I can live with that. So there were several things that I was like, that's a bug that I can live with. And every year I try to work on one or two about the bugs. If I put 10 calories and try to improve the feature, I get like a thousand out. And so I more paid attention to the features and tried to get better at the features.

• 20:26Speaker 00

  And this took me a while to figure this out and over time, just tried to hire people around my weaknesses. And I have plenty of them. I really looked at hiring the best I could in the areas where I was weak, rather than trying to become an expert at it. And I'll give you one area. Where I made a mistake on this. In the early days of HubSpot, I fashioned myself like a great product designer. I don't know why I did. I think basically because I followed Steve Jobs, everything he did, read every book about him, watched his keynotes, was obsessed with him as CEOs are my era. And I was like, I can do that. I can figure it out. I took classes and I really dug in.

• 21:04Speaker 00

  And for years, I was convinced I was a great product designer. I'm not. I just don't have that genetic code. I was actually quite bad at it. It took a while before that feedback sort of hit me between the eyes. We started hiring people really good at it and enabling me to let go of it.

• 21:22Shane Parrish?

  What are some of the lessons you took away from your sort of studying of Steve Jobs, if you will, that you used effectively?

• 21:30Speaker 00

  One of my favorite things on the interwebs is his keynote and his commencement speech at Stanford. I think it's quite good. And once in a while, I'll look back at that. He was based with cancer. And the way he approached that was really interesting. And he says it in a different way, but he didn't waste any time, that's for sure. And then HubSpot a lot is based on his work. We started the company out of Sloan while we were at business school. And at Sloan, they did field trips. And we did a field trip to the West Coast. And I remember this one day, it was a really good day. In the morning, we visited Apple. It was like a year after the iPod came out and it was on fire. And I remember Steve walked into the auditorium, it was about a hundred of us.

• 22:14Speaker 00

  And he was in a bad mood and it was pretty intimidating. And I remember he looked, he looked out and he basically was like, what are you people doing here for business school? Like, he wasn't into the whole business school thing. And one of my classmates, JP Gorski, raised his hand up high and he said, we're here from Sloan School of Management and we're studying innovation disruption. And we thought we'd learn from the best. And Steve just melted. He liked that a lot. And then he talked about how we came up with the iPod. And kernels of this very much made it into the way we thought about HubSpot. And the iPod, the way he described, was really simple. There were MP3 players before, but you had to be a real geek to use one. And very few people were buying them and you had to burn music to them. It's a pain in the neck to do it. And he said, I really wanted something simple.

• 22:59Speaker 00

  So I wanted to take an MP3 player, build a freemium app, iTunes, and then work with the record company, enable you to download a song for 99 cents a song. And he said, that's a one plus one plus one equals 10 for the consumer. And that was how we originally came up with HubSpot, like a marketer in that day and age, putting Google Analytics and a blog, social media tracking tools, and SEO tools, marketing automation, CRM, and all this stuff. And it was complicated. It was a big hairy problem. And so we used that analogy very much that Steve used. Like, how do we make it all one system where the one plus one plus one will equal 10 across all the systems? So the morning was really influential. And then that afternoon, we're kids, we're in business school.

• 23:44Speaker 00

  We visited a little startup called Salesforce.com and their CEO, Mark Benioff. And so that day was really formative in thinking about HubSpot.

• 23:53Shane Parrish?

  Oh, that's crazy. Had you guys just taken your tuition and invested in both of those companies?

• 23:57Speaker 00

  I know. That's a good point.

• 24:01Shane Parrish?

  That's crazy. So you started it in school. How did you learn how to hire and fire people? Like, how do you know you have the right fit? How do you know when it's time to move on from somebody? You know, I think about that as somebody who went from school to a large corporation and they have all these policies and procedures in place. And then now as an entrepreneur, I'm dealing with CEOs all the time who've never really hired and fired. And I'm curious as to what wisdom you can sort of pass on to people.

• 24:29Speaker 00

  Most CEOs, including myself, are quite bad at this.

• 24:35Speaker 00

  And I've identified some things that may be useful hacks, may not be useful hacks. This is also a seasoned thing. If you're hiring someone when you're 200 employees, I see the mistake everyone makes, and we made the mistake over and over and over and over again, that if you're hiring someone that you want to go from 2 to 2,000, you're just really attracted by that person who came from Google or Microsoft or whatever huge company with a huge resume and all that stuff. And once in a blue moon that'll work, but generally that's a failure condition. If you hire with a press release hire that said a couple phases over you, I don't think it normally works. Same thing for board members.

• 25:17Speaker 00

  My analogy for being a CEO is like you're an ice climber going up the ice, and it's treacherous and you could easily slip. And what you're looking for are executive members who have been up that same sheet of ice, but in the last three or four years. What you don't want is somebody who's 20 years over you or someone who spent their whole career on top of the hill looking down on the ice climbers. You want somebody just a little bit ahead of you on that ice climbing mission. So that's one thing I think people get wrong. I also think, I think most people are bad interviewers, including myself. Like I've missed a bunch. And I think the core reason for that actually isn't the interview, it's interviewees. Interviewees are so good in interviewing.

• 26:02Speaker 00

  You're interviewing a VP or a C-level person for a company like HubSpot. They're good at interviewing. And if they're not, they've been coached, they've looked on YouTube. Like, I just think everyone, including myself, overvalues their ability to select talent in the interview process. I see that as a... Overconfidence. I think also like I see it with the CEOs I work with and I see it as companies get bigger, like you've got a panel of four people evaluating Shane as a potential VP. If all four people like Shane versus two people love Shane, two people are like, eh, I'm not sure about Shane, you almost always go with the person with the least amount of weaknesses and

• 26:47Speaker 00

  that lowest common denominator hire. I think that's a failure conditions. We've noticed that over time, I take two loves and two me's over three likes. Uh, I think that's a best practice that people should be doing. And I think people should be obsessed with reference checking. Uh, yeah, calling the references, getting good at that, getting good at finding people in your network who work with them. I would guess I coached tons of CEOs on average for every director, VP, C-level person that's hired within 18 months, they're gone.

• 27:20Shane Parrish?

  How do you know when it's time to move on from somebody? Or you, I guess in a way you've either made the wrong hire or it's the wrong environment for that person to succeed, or however you want to phrase that. But how do you recognize that? I, I had a CEO the other day tell me is like the moment you start thinking about it, that's the moment to act on it. I've never seen anybody change their mind from that initial thought. How, how do you think about that? And what's your reaction to that?

• 27:44Speaker 00

  Unfortunately, that's, I feel like that's conventional wisdom and I think it's largely puts with what I've seen. I rarely change my mind on people in that kind of context. And everyone says, when you know you should move quickly. I never had. They call me weak.

• 28:05Shane Parrish?

  Have you ever regretted not moving quickly? It's sort of interesting to contrast that to sort of like Jensen, who's been talking recently about, you know, he doesn't really fire people. He's sort of like berates them into being better, uh, in, in a public way. B-rate is probably the wrong word, but he, he sort of wants to pull you towards excellence rather than, uh, fire you. But I, I don't think that's practical for most people or most organizations.

• 28:29Speaker 00

  So you and I both sat through the same Jensen presentation.

• 28:32Shane Parrish?

  Yeah.

• 28:32Speaker 00

  So I spent a lot of time thinking about CEO-ism and coaching CEOs. And there's sort of like a set of best practices for being a CEO. It's almost like a CEO unofficial school. What's confusing about the CEO school that's been around for a long time. Is arguably the two, I'm not going to say best, but two amazing CEOs are Jensen at Nvidia and Elon, it's SpaceX and that's a, that's a, that's a, that's a. And they completely ignored almost everything about CEO school, CEO lessons, CEO best practices. And I find that fascinating.

• 29:14Shane Parrish?

  Talk to me about that, right? Where maybe there is no model. We hold up this model. We teach it. It's easy to do. We say the right things, but in reality, the people that end up changing the worlds are often the opposite of all of the points that we teach. Berkshire Hathaway, for example, if you looked at their board of directors, I don't think they pass any of the, the sort of like standards that business schools would set for what an independent board looks like. And Constellation Software is another example of that. So is Shopify. All these companies that have sort of done these remarkable things, they don't look anything like what we're taught in business school.

• 29:51Speaker 00

  When Humpso was maybe like 50 employees, Shane, I joined a CEO group. And I largely joined the group because I respected one of the CEOs and I got him Colin Engle. And Colin made the Roomba vacuum cleaners at iRobot. And I, I, my, we described my relationship with him in two words, man crush. I was a fan of Colin's. And I remember this first CEO group, we met all day, once a quarter. And I remember this couple of funny things about the, the CEO group. But I joined, and I sure remember spending some time with these 10 CEOs. And two were kind of, they're quirky is the way I would describe them and very unique personalities.

• 30:33Speaker 00

  And the other were like central casting, a blue blazer, tan pants, like really central casting, backgrounds and everything. And they acted what I thought CEOs were supposed to act like. And I kind of acted like that back then. And when I looked at the numbers, we all showed each other your numbers. The two quirky founder CEOs were crushing it and the eight central castings were with me. And I was like, enough with trying to be central casting. I'm going to be exactly who I am and we're going to make everybody else work around who I am. And it's a lot easier being who you are than somebody else. Everybody else is taken. That was when I was like, I'm quirky too. I don't care that I'm quirky. I'm just going to lean into my quirkiness and be myself. And I've sort of been that way ever since. And I don't think there's a profile of CEO.

• 31:18Shane Parrish?

  You were talking earlier how you'd love to hire somebody with two, I love this person and two Matt. Is that because of that? Because the person who says all the right things, everybody's going to be okay with. But the unconventional person, you're going to get really two extremes. You're going to get love or hate.

• 31:33Speaker 00

  I think what happens as the company scales is you hire for a lack of weakness, not for spiky strengths. And that's institutionalized in the scale ups, interviewing panel and process. And I think that's a mistake. And that's one of the few things that leads to really mixed success in hiring execs in these companies.

• 31:55Shane Parrish?

  Who do you think is the most underrated public company CEOs?

• 32:02Speaker 00

  I think the guy running Uber has done a nice job. That was a very, very, very difficult thing he took over. He got it profitable. I think he's done a really, really nice job, very quietly done a very good job. How about you?

• 32:17Shane Parrish?

  Oh gosh, I think Toby is massively underrated. We were sort of talking about him during the break here. What are your thoughts on Toby?

• 32:25Speaker 00

  Toby reminds me a lot of Colin Engel, actually, just whip smart. One of the things I like about Toby and Colin is they're very first principles thinker. They don't care to receive conventional wisdom. They're going to think it through from scratch and sometimes you're going to get it wrong. But a lot of times they're going to get it right and do something really innovative and smart. Toby's got so much right. He's got some big stuff wrong, but for the most part, he's done a really, really good job. He's certainly not central casting.

• 32:56Shane Parrish?

  Yeah.

• 32:56Speaker 00

  Certainly not. And I think he's brilliant and a great CEO and he's running a great company.

• 33:01Shane Parrish?

  I like that term central casting. Another person who stands out to me, most people are probably familiar with now, but 10 years ago, nobody would have ever heard of is Mark Leonard. From Constellation Software.

• 33:12Speaker 00

  She's not really on my radar.

• 33:14Shane Parrish?

  Yeah, exactly. I think they only issued equity at the IPO and they're, I don't know, must be 50, 60 billion dollar company now.

• 33:21Speaker 00

  Amazing. See, I wouldn't put Toby in the underrated because I rate him so highly and I feel like people in my circles rate him highly.

• 33:29Shane Parrish?

  Yeah, I rate him highly too, and I still think I underrate him.

• 33:32Speaker 00

  Okay, got it.

• 33:33Shane Parrish?

  Yeah, yeah, totally.

• 33:35Speaker 00

  There's one other interesting thing that's I think relevant out of that CEO group. I remember going to the CEO group meeting, the first meeting, Jane. And what I didn't realize is there was a topic for the whole day. And one of the quirky things about HubSpot up until that point is we didn't have any HR people. We didn't allow anyone to talk about culture because we didn't think the imagery was too squishy. And I remember I arrived there on the first day, first thing that got put up was the topic of the day. And sure enough, it was culture. And I remember thinking, that's gonna be a big, big waste of time. At least I got to know my man crush. The whole morning I was pretty disengaged. And then Colin, at

• 34:19Speaker 00

  lunchtime, I remember he said to me, he's like, why aren't you engaging? You don't like the topic, do you? And I said, no, I think it's a waste of time. He said, Brian, culture. Culture is how people make decisions when you're not in the room. Culture is how companies really scale. Okay, okay, okay, okay, got it. And then the afternoon, sort of engagement. And then the next day, I go to the office, so my co-founder, Darmesh, says, how's the op- how was it? How's Colin? Like, how did it go? I said, it was really, really good. There's, there's one, they do one topic a day. He said, oh, what's the topic? I said, it's culture. He said, oh, shit, what a waste of time. I said, no, Darmesh, culture is how

• 35:03Speaker 00

  people make decisions when we're not in the room. Culture is how HubSpot's gonna scale. And he said, okay.

• 35:10Speaker 02

  Hey, Bose here. On your next track, listen for the decisions. Distortion on the bass, the vocal right up front. Every choice deliberate. With Bose, you'll hear it all. Your music deserves Bose.

• 35:26Speaker 03

  This episode is brought to you by Michelob Ultra. Good times mean competitions between you and your friends. Like seeing who can throw some pigskin the farthest or rush the field the fastest. Winner gets an ultra because it's not just a superior like beer. It's also giving fans superior access to their favorite sporting events. Superior is worth playing for. Visit michelobultra.com/superioraccess to enter. Enjoy responsibly. Copyright 2026 Anheuser Busch InBev Michelob Ultra Beer, St. Louis, Missouri.

• 35:55Speaker 00

  And it's very hard for me to assign work to my co-founder to this day. Somehow I assigned him to be the culture czar of HubSpot and he did an excellent job. And still is doing an excellent job of marshalling the culture from, you know, 50 employees, 8,000 employees. And he did two clever things. First thing he did is we're big on net promoter surveys. So he surveyed all the employees, scale them one to 10, how likely to refer HubSpot as a place to work? And then why? Again, people wrote novels about it and he kind of broke it all up into, you know, different topics. And then he wrote a PowerPoint presentation called the HubSpot Culture Code that basically described

• 36:36Speaker 00

  the relationship between employees and company and just sort of outlined how we thought about culture. And then he posted it on the internet and it blew up on the internet. But we continue to do that net promoter score once a quarter for the last 15 years. And we're tracking our net promoter score per quarter. And that's been very, very useful. Then we post every response to the net promoter survey on culture on the Wiki. And then we address the issues that come up. That best practice the serve as well. Every six months, we refactor the PowerPoint deck. It's a living, breathing document and we basically treat culture like our second product, like our product HubSpot. If it's unique relative to the competition, it's a good quality product and it delivers value.

• 37:20Speaker 00

  It's like a magnet that pulls customers in and retains them. Same thing with a culture. If it's unique relative to the competition, it's high quality and adds value. It's like a magnet that pulls in employees and retains them. And so we put a lot of thought into that culture stuff. And I think a lot about how do you take, how do you go from startup and scale up? I think a key part of that is getting your culture right and writing it down and institutionalizing it.

• 37:43Shane Parrish?

  I'm going to make a statement about culture and I'd love for you to argue, take both sides of the debate, if you will. So I'm going to say that culture is the only sustainable advantage.

• 37:53Speaker 00

  I disagree.

• 37:54Shane Parrish?

  Why?

• 37:55Speaker 00

  Let's take Uber. They had a certain culture. Dara, the new CEO came in. I'm quite sure he made massive changes to the culture the founder put together. And he thrived. I don't, I think some of the benefit, of course, is his culture. But they had major sustainable competitive advantages in that they had a fleet of drivers and customers and the network effect and software that works. And he's probably been there 10 years and I don't think it's all culture.

• 38:25Shane Parrish?

  Oh, that's interesting. So in my mind, I would sort of think of that more like they had a advantage, like an operational advantage that came from the network effect and the scale.

• 38:39Shane Parrish?

  I don't know if that would have been enough to sustain it going forward without the culture.

• 38:45Speaker 00

  Fine. I sort of agree with that. I think the best example on the other side of this is Satya. Satya is on my Mount Rushmore CEOs. A lot of people push back from me. It's like, oh, he wasn't a founder. You shouldn't be on there. He's on there for me. Because Microsoft was going very, very sideways for a long time. And he stepped in and really did change the culture in a massive company. And, and couldn't be more impressed with him and the culture change and, and how well that worked. So that's, that's my flip side of the argument is Satya.

• 39:18Shane Parrish?

  Okay. Who else is on your Mount Rushmore?

• 39:21Speaker 00

  Jerry Garcia is on my Mount Rushmore, great CEO, the aforementioned Steve Jobs on there.

• 39:28Shane Parrish?

  Why Jerry Garcia? Grateful Dead.

• 39:30Speaker 00

  Really? Why Jerry Garcia? That's the most obvious one on there.

• 39:34Shane Parrish?

  Why? No, I'm curious. I'm not a Grateful Dead. I've never, I don't think I've ever really sat down and listened to the Grateful Dead. So you're gonna have to walk me through this one.

• 39:43Speaker 00

  Okay, Jerry Garcia was the CEO cut in the cloth of Colin Engel and Toby Lukie. Really disliked conventional wisdom and kind of rethought everything from first principles, starting with the music. So they started that band in the mid 60s. And at the time, there was all kinds of rock and roll music and there was jazz music, country music and bluegrass music. And they didn't do any of that. They created a new genre of music. People refer to as jam bands now, but Garcia himself was a bluegrass player and the bass player was a jazz musician. And the keyboard player was a blues guy and Bob Weir, the singer, was kind of a country rock and roll guy. And they blended them all together and they infused this jam band mentality into it.

• 40:28Speaker 00

  And they really stretched the songs out with improvisation. So they sort of rethought the genre and made a new type of music. The product was unique and the go to market was exceptionally unique. If you think of like, when I was in high school, if I wanted to go to a Rolling Stones concert, I would call Ticketmaster. And I would wait till whatever it is, 1:30 on a Tuesday, when the Rolling Stones tickets were on sale. And I would, you know, dial away, it'd be five minutes later to dial away and it may not come through. The people who ended up buying most of the tickets were the scalpers. The scalpers had a whole bunch of people buying the tickets that sold the tickets in a markup. And so the front row of the Rolling Stones concert

• 41:11Speaker 00

  was a bunch of bankers and venture capitalists, people who could afford the tickets. And the Grateful Dead didn't like anything about that, Shane, nothing about it. They particularly didn't like a bunch of bankers and venture capitalists in the front row of their concerts. They wanted their hippie crazy fans in there. They also didn't like the distribution setup. So it's Grateful Dead and then Ticketmaster took their slice and then scalpers took their slice and then the fans. So they said, we're going to disintermediate, just like the internet did to so many things. We're going to disintermediate those two layers and we're going to sell tickets directly to customers. The way they did it was you listened to a 4015 recording that explained what was going on. And the way Shane, you would buy the tickets was you have to put a three by five card, which concert you went to.

• 41:56Speaker 00

  You can only buy four tickets per concert. Okay. So the scalpers are less insensitive. And then you had to go to the post office, get a postal money order. So just a total pain in the backside to get a postal money order. And then you had to put a self-addressed envelope and then you put a regular envelope and mailed it in. Now, how would the Grateful Dead chain decide who gets the front row seats?

• 42:19Shane Parrish?

  I have no idea.

• 42:20Speaker 00

  The way they sort of did it was that self-addressed envelope, the more beautifully you could decorate it with dancing bears and mushrooms and sprinkles.

• 42:29Shane Parrish?

  I love it.

• 42:30Speaker 00

  Yes. So they solved a bunch of problems. That's not the end of it. When was the last concert you went to, Shane?

• 42:36Shane Parrish?

  Oh God, it's been a long time.

• 42:38Speaker 00

  Did you go to Taylor Swift?

• 42:39Shane Parrish?

  No, I am a Taylor Swift fan.

• 42:42Speaker 00

  Okay, let's just say you went to Taylor Swift in Ottawa.

• 42:46Shane Parrish?

  Yeah.

• 42:46Speaker 00

  And you showed up with your giant camera and your boom microphone and you showed up there. What would have happened at the gate?

• 42:54Shane Parrish?

  They wouldn't let me in.

• 42:55Speaker 00

  Why? Why didn't she want you recording?

• 42:58Shane Parrish?

  It might affect other people's experience if I have a boom mic. I mean, you can't prevent people from recording on their phones. So at some degree, they're accepting it. The NBA actually went through this a couple of years ago. They were trying to like really block people from posting clips on social media. Then they actually embraced it and it changed the whole league.

• 43:19Speaker 00

  Mark.

• 43:19Shane Parrish?

  It got way more people, sorry, this is like a sidetrack to this, but like that change in the NBA really changed the NBA.

• 43:27Speaker 00

  Okay, pre iPhone, let's say you were going to a Rolling Stones concert and you had all that equipment you're walking. Of course they would block you. And the reason is you see the Rolling Stones in Boston and New York and then Philly and then Miami.

• 43:41Speaker 00

  The exact same concert, like they don't miss a note. They're fantastic.

• 43:44Shane Parrish?

  Same thing.

• 43:45Speaker 00

  When you walked into the Grateful Dead with your big boom mic and your big camera, they put you right in the taper section, the perfect spot to watch the concert. They said they do to tape it. And you taped it and then you went from Boston, then you went to New York, you taped it, you went to Philly, you taped it. Then you went to Miami, then you get back to your dorm room and you copied as many tapes as you could of the best concert, not the worst concert. And you gave them out to all your friends. And that was how they market. They gave away the content. They were the first inbound marketers to really nail that. They were the first real freemium model. They were the first viral marketers and the way they do it was brilliant. And it worked for them because every concert was quite unique. They're a jam band, so they've never played the same setlist twice.

• 44:30Speaker 00

  And so there was an incentive for knuckleheads like me to go from Boston to New York, that that that up and down the East Coast. In fact, I did that last week. I was at the Sphere and I saw them Friday, Saturday, Sunday. Garcia was a genius. He's a marketing genius, actually, and I think he's a music spot.

• 44:47Shane Parrish?

  That's fascinating. I'm gonna have to listen to the Grateful Dead now. I'm like.

• 44:52Speaker 00

  I'll send you some stuff.

• 44:53Shane Parrish?

  Yeah.

• 44:55Speaker 00

  I wrote a book on this called Marketing Lessons from the Grateful Dead.

• 44:58Shane Parrish?

  We started talking about inbound marketing there. I'm curious as to, you guys pioneered inbound marketing to a big extent. And definitely got the momentum rolling there. How has that changed in the past few years? And where is that going in the next few years?

• 45:15Speaker 00

  Ironically, I think it kind of went out of favor a bit over the last few years, and I think it's about to come back in favor. The things that changed about it aren't that different. Instead of like cold calling people and spamming people and advertising at people.

• 45:32Speaker 00

  In renting space on YouTube or renting space on your podcast or your blog or renting space on the New York Times, create your own New York Times, your own podcast and become your own publisher and then pull people in through Google and search and other social outlets. It works very, very, very well. You're living proof of how well it works. The things that have changed are the social media networks have changed. When we first wrote about this, before we started HubSpot, we started writing about inbound marketing. Dig and Reddit were the two big social media sites. I don't think Dig's around and Reddit's gone through all these iterations, but obviously it was Facebook and now it's TikTok, it's Instagram. It's all these new social media sites. It's YouTube. Yeah, people live in

• 46:13Speaker 00

  YouTube. It's podcasts. And so the medium isn't necessarily a long form blog like it was back when we started HubSpot. It's videos, a lot of short form videos. And so that's changed quite a bit. I think what's interesting about what's going on now is today you go to Google and you get your 10 blue links. If you look across our customers, that's 62, 63% of the inbound traffic is via Google and most of it's organic. I think over the next five years, that's going to change a lot. I think Google's going to have to change a lot. And I think people are going to spend more and more of their time inside ChatGPT and all ChatGPT's competitors. And I think when you're engaging in that way and you do a search in ChatGPT for, let's say HubSpot, it'll tell you about HubSpot and then you'll

• 46:58Speaker 00

  say, well, how does HubSpot compare it to Salesforce? It'll tell you about that. How much is HubSpot possible? It'll tell you that. Like, people know a lot about HubSpot. One of the brilliant things about Google is their blue links and they didn't mind sending you off their website. It's a very counterintuitive idea. I think that's going to start changing as consumer behavior changes and I think it'd be really interesting to see how it evolves.

• 47:17Shane Parrish?

  Do you think content is just going to get overwhelming? I mean, you can create content with like two sentences now. You can create blog posts that would rival probably the best people were putting out maybe 10 years ago with almost no effort whatsoever.

• 47:34Speaker 00

  I think you're right. And I think it's not just that, but it's going to be emails. Like, I think that the robo emailing and the BDRs, I look at lots of startups in the CRM space, as you might imagine, but there's about 48 startups building automated AI agents. I still think having a unique perspective and a unique personality.

• 47:57Speaker 00

  Is gonna work. I don't think your podcast goes away because I start something that sounds like you and I use an avatar to deliver it. I think something what you're doing will last the test of time. And I think a lot of people, particularly in scale ups, run away from their personality. They make it generic and like you have a certain vibe and a certain personality. And I think that kind of works for you and it's gonna be very hard to replicate. Quality and uniqueness never go out of style. And I think are going to be increasingly important as you know, it just fills content that's AI generated.

• 48:28Shane Parrish?

  It's almost what you said before, like lean into your individual quirkiness and your tribe will sort of find you and then go around with you. Although you had me worried, we're almost a million people on our newsletter now. I'm like, oh God, if this is going away, I got problems.

• 48:41Speaker 00

  I also think we're gonna see the trend, and I'm certainly not the first person to say this, but I think you're gonna see a lot more small, big companies and you're gonna be able to get a lot more done with a lot less people. I don't think in a billion dollar company, you're gonna need three, four, 500 person marketing organizations. I think the new tools are coming out, including HubSpot's tools and the CRM suite. I just see how incredibly powerful they are. I think you're gonna be able to scale in a whole new way. And I think the AI revolution, like when it comes to inbound, I think top of the funnel gets more difficult. I think middle of the funnel gets easier, but really high quality personalization on your website, on chat, on everything, that gets much more powerful. Top of the funnel gets more difficult.

• 49:26Speaker 00

  Yeah, I think inbound's gonna change, but I also think inbound, you're gonna kind of make a comeback.

• 49:31Shane Parrish?

  How do we do outreach in a world of AI and in a world where people are bombarded with, is it gonna be freemium and then pulling people in through that? And like the outreach is letting them know about the freemium stuff?

• 49:42Speaker 00

  You gotta get good at the branding thing, again, it turns out, because getting into your or my inbox is gonna become exceptionally difficult with all the changes Google's making to email. That's getting harder as it is, but the robo emailing is gonna go wild and the robo content's gonna go wild. So it's a little more around branding. You have to kind of be good at everything. It's like a baseball five two player. You have to be getting found in YouTube. You have to be getting found on all the social sites. Chat GPT is going to understand you perfectly well. Google's going to understand you perfectly well. And you need people tripping over here all over the place. I think people have to get comfortable with the fact they're going to have less new visitors to their website. Because Chat GPT and their ilk are going to know so much about you and not have those list of blue links. They're just going to live on there and learn so much about you.

• 50:24Speaker 00

  And then when someone's quite serious, they end up on your website and you have to get very good at personalizing that website experience. I also think people are going to end up keeping more information behind the paywall and the login wall on their websites. Because they want to keep a little bit back from Chat GPT. Because Chat GPT is going to understand the public stuff so well. I think it's going to change it a good way though.

• 50:47Shane Parrish?

  I guess the baby step that Google made on that was like when they would just show you sort of the excerpts.

• 50:53Speaker 00

  Yep.

• 50:53Shane Parrish?

  If you asked a question, it'd be like basically giving you a link, but it's like really hard to find. It's like, here's the answer to your specific question. YouTube is fascinating because unlike voice podcasts, YouTube has virality to it. So like when we do an in-person recording, the YouTube reach is larger. In some instances, not all, than our podcast reach. And so we get like 300,000 people sort of listening to a podcast episode. But on YouTube, we'll get 300 to 500 to a million.

• 51:27Speaker 00

  Nice.

• 51:28Shane Parrish?

  People, but it's YouTube's algorithm picking it up. It's like people watch this. Uh, but what we can't do is like send people off that platform. So it's really good for like stats. Like I, I was at the, the gym the other day and this guy's like, I got two million TikTok followers, but I can't do anything with them.

• 51:44Speaker 00

  Yeah.

• 51:45Shane Parrish?

  So, so I can keep them on this app and I'm really famous in this localized environment, but TikTok is 100% in control. I don't own that relationship. Same as YouTube. I don't own the relationship with the viewer. YouTube does. The minute it doesn't like me and wants to cancel me or doesn't like my content anymore, or wants to promote a different message. Whatever that algorithm is that's doing that can just like, you're gone.

• 52:09Speaker 00

  I think you're right. I thought Google was going to roll over and play dead there for a little while. Like, I moved most of my search traffic to Perplexity. Really like it. Google's kind of started and stopped a whole bunch of stuff, but recently they're making noises like they're not going to roll over and play dead to Perplexity. That's such an interesting company right now, and to watch their moves will be very, very interesting. It's a challenging time for them, but it looks like they're gonna, they're not going to let Perplexity just hoover up a bunch of their users.

• 52:36Shane Parrish?

  Hopefully not. We all want some competition here. I have a couple of random questions. I'm curious what you've learned about making decisions that you think other people miss.

• 52:45Speaker 00

  On my CEO journey, for a long time,

• 52:50Speaker 00

  I would kind of look for consensus. I think consensus is really the enemy of scale. And so I used to say, whenever we're making an important decision, there should be winners in the room and losers. We shouldn't find like that negotiated settlement that everyone's happy. Somebody should be unhappy. Three or four people should walk out unhappy, and one should walk out happy. And we're all, we're all going to be good with it. As you get bigger, this gravity pulls you towards consensus, and I think consensus is the enemy of greatness.

• 53:19Shane Parrish?

  How do you fight that?

• 53:21Speaker 00

  I write that on whiteboards. I talk about that inside of HubSpot. I try to make an example of that every time I'm in a room. I've written a bunch of blog articles about that, wiki posts about that. At one point at Sign of HubSpot, we had a terrific T O O. I love. And he had a lot of great qualities. One of his qualities I didn't love was he was a consensus person. And we had a lot of conflict over that. And so we talked about that a lot. The management team talked about that a lot. But I sort of had this thing like, there's going to be winners and losers in every argument. And if no one walks out a little bit sore, we probably made the wrong decision.

• 53:54Shane Parrish?

  So go deeper on that for a second, though. So put me in the room at one of these meetings where there's four people on one side, there's four people on the other side. How do we come to that decision? Is it the highest paid person in the room? Is it the person closest to the problem? Who actually makes that call?

• 54:11Speaker 00

  Let's just say it's my call, which is rare. And two people in the room are saying black and two people in the room are saying white. I think that the majority of CEOs are walking out of the room with the decisions gray.

• 54:23Shane Parrish?

  Trying to please everybody.

• 54:24Speaker 00

  Yeah, try to thread the needle. And I think that's a problem. It creeps in more and more, the bigger you get, the worse that problem gets. And I always tried to walk out of the room. It's like, we're gonna pick black or white. If you lose this decision, you might win the next one. Let's not get all pissed off about it. We'll all survive. And I think that's the right way to scale it.

• 54:43Shane Parrish?

  Is there anything else you've learned about decision making that you're like, oh, I wish I knew this sooner?

• 54:48Speaker 00

  I would say one thing I've learned about scaling a company, like from the outside, went from company with an idea and two employees to, you know, it's worth $30 billion and 8,000 employees and a couple hundred thousand customers. It looks like a smooth graph from the outside, but I'll tell you what, it's a grind on the inside, building up spot. It's very much two steps forward, one step back, two steps forward, one step back, two steps forward, one step back, the whole way. And there was no silver bullets along the way. There was no one higher that completely changed the game, no partnership that changed the game, no customer, no investor.

• 55:30Speaker 00

  It was all kind of two step forward, one step back, two step forward, one step back. And the other thing I would say about the journey is kind of related to that. There was definitely wartime and peacetime. When you're halfway through a two steps forward, it was peacetime. When it's one step back, it was wartime. And I love wartime. I'm definitely a wartime CEO. I hate peacetime. I really need to sit on my hands and just let it go. Like, it's going great, leave it alone. And I have a hard time doing that. And I think certain CEOs are peacetime and certain CEOs are wartime. I'm very, very, very much a wartime person. Like COVID, wartime. We made so many changes during COVID. I hated COVID and I hated being back in society, but inside of HubSpot, that was a fun chapter.

• 56:13Shane Parrish?

  What does wartime mean for you? Is that like we're fighting for our very survival? Does it mean we can just move faster and sort of ignore some of the bureaucracy? What does it mean?

• 56:24Speaker 00

  I think peacetime is bottoms up. And more consensus, a work time more top down. It's like, hey, it's work time. I don't have time to build consensus on this. This is what I think we should do. We're going left.

• 56:38Speaker 00

  And I like that about a work time and work time is like, okay. I remember 2010, the economy was shaky back then and we were a very young company. Maybe it's 2009 and our retention statistics were horrible. Everyone was canceling. Our product wasn't good back then. And we lost, I remember a thousand customers we had in the beginning of the year. We lost like 700 of them, like just terrible churn rate in 2009 and that was existential. And it was like, let's just stop the music and start over. Everything we're doing going forward has nothing to do with signing up new customers. It's like, how do we delight every new customer we have? Let's stop obsessing about how do we turn a prospect into a customer?

• 57:21Speaker 00

  Let's obsess about how do we turn a customer into a delighted customer? And so that was a crisis that really worked. We changed the culture of the company. We changed the center of gravity from prospects to customers. Never waste a good crisis. That was a really good crisis.

• 57:34Shane Parrish?

  While you're building this, how did you manage? And I don't want to say balance, it's the wrong word, but it's the word everybody understands. How do you, how did you manage work-life harmony or balance? Especially during the high pressure periods with a young family.

• 57:50Speaker 00

  I didn't. I did it very poorly.

• 57:52Shane Parrish?

  What would you go back and tell your younger self now?

• 57:54Speaker 00

  I'm really proud of it. I think my grandkids will be proud of it. And I think it took a big effort on my part to pull it off. And if I said, oh man, I wish I'd just put in 40 hours a week back then. I wouldn't be sitting on this podcast with you. We wouldn't have pulled it off. And I know that's not the popular answer. I'll probably get Hillary on Twitter for saying that. I think that's a reality at TopSpot. It was, it was a full context sport.

• 58:18Shane Parrish?

  I've noticed this thing and I think people don't like talking about it. But when you find exceptional people who've done exceptional things like yourself.

• 58:28Shane Parrish?

  They're not always the most well-rounded people in every aspect of their life. And yet, we sort of expect them to be, right? It's like, we, we love Warren Buffett, but we want him to also be a better family man. The weird thing is, the minute Warren Buffett starts doing that, he's no longer somebody we're talking about as Warren Buffett. And it's so, it goes back to those sort of like strengths and weaknesses. And my hypothesis is that people at the tail end of the curve have incredible strengths and incredible weaknesses. And by trying to address those weaknesses, whether at school, society, nudging people, we actually limit,

• 59:08Shane Parrish?

  we put a ceiling on the strengths that those people can actually deliver to the benefit of the world.

• 59:14Speaker 00

  You'll probably pillory it on Twitter for saying that, but I agree with you on that. I will give, I'll give you an example. I've never been married. I want to get married. It's on my, it's actually on my to-do list this year. I don't know if it's me this year, but I never did it. And every time I had a relationship, like HubSpot came first. And do I regret it? I don't know. I've had a really good life. I've really enjoyed the HubSpot run. I'm super proud of it. I think when I'm 85 and looking back on my life, I'll still be super proud of it. I think my grandkids will be proud of it. So yeah, I made some sacrifices. I'm okay with it.

• 59:54Shane Parrish?

  We always end the podcast with the same question. I think you'll have a really good answer to this. What is success for you?

• 59:59Speaker 00

  I think it's a really cheesy James Taylor song named "The Secret of Life is Enjoying the Passage of Time." I think he's very right about that. And think about that post my accident. I very much try to not do anything that I don't want to do, or if I'm doing it not to do it, very long. And I try to live in the present and stay out of the past too much and stay out of the future too much. I think the secret of life is about how do you set your life up so you're really enjoying that passage of time.

• 1:00:31Shane Parrish?

  That's a beautiful answer. Thank you so much for coming on the show, Brian.

• 1:00:35Speaker 00

  Thank you, sir.

• 1:00:42Shane Parrish?

  Thanks for listening and learning with us. For a complete list of episodes, show notes, transcripts, and more, go to fs.blog/podcast or just Google The Knowledge Project. Recently, I've started to record my reflections and thoughts about the interview after the interview. I sit down, highlight the key moments that stood out for me, and I also talk about other connections to episodes and sort of what's got me pondering that I maybe haven't quite figured out. This is available to supporting members of The Knowledge Project. You can go to fs.blog/membership, check out the show notes for a link, and you can sign up today. And my reflections will just be available in your private podcast feed. You'll also skip all the ads at the front of the episode.

• 1:01:28Shane Parrish?

  The Frontline Street Blog is also where you can learn more about my new book, Clear Thinking: Turning Ordinary Moments Into Extraordinary Results. It's a transformative guide that hands you the tools to master your fate, sharpen your decision-making, and set yourself up for unparalleled success. Learn more at fs.blog/clear. Until next time.