#200 Brian Halligan: Scaling Culture from Startup to IPO

0:00:04 If I put 10 calories and try to improve the feature, I get like a thousand out.
0:00:09 And so I more paid attention to the features and tried to get better at the features.
0:00:10 And this took me a while to figure this out.
0:00:14 And over time, just tried to hire people around my weaknesses.
0:00:16 And I have plenty of them.
0:00:20 I really looked at hiring the best I could in the areas where I was weak,
0:00:21 rather than trying to become an expert at it.
0:00:23 And I’ll give you one area.
0:00:26 And for years, I was convinced I was a great product designer.
0:00:27 I’m not.
0:00:29 I just don’t have that genetic code.
0:00:31 I was actually quite bad at it.
0:00:35 It took a while before that feedback sort of hit me between the eyes.
0:00:39 We started hiring people really good at it and enabling me to let go of it.
0:00:48 Welcome to the Knowledge Project.
0:00:50 I’m your host, Shane Parrish.
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0:01:18 My guest today is Brian Halligan.
0:01:23 Brian reshaped the way that we think about marketing, sales, and customer service.
0:01:26 With his co-founding of HubSpot in 2006,
0:01:29 he pioneered the concept of inbound marketing,
0:01:34 emphasizing the importance of creating valuable content to attract customers naturally.
0:01:38 Under his leadership, HubSpot has grown from a startup to a publicly traded company
0:01:41 and a global leader in the industry,
0:01:44 empowering millions of businesses to grow better.
0:01:48 I first met Brian at a Sequoia conference where we both spoke.
0:01:55 In the conversation we talk about the phases of a CEO from startup to IPO and how the skills
0:02:00 change, why interviews are a terrible predictor of on-the-job success and what you can do about it,
0:02:05 why hiring panels are flawed, what changed after his near-death experience,
0:02:10 why Jerry Garcia from The Grateful Dead is one of the most underrated CEOs
0:02:14 and what you can learn from him, why consensus is the enemy of scale,
0:02:17 why you need to have winners and losers,
0:02:21 what he learned from Steve Jobs and of course the future of inbound marketing.
0:02:24 It’s time to listen and learn.
0:02:44 Brian, I want to start with the role of a CEO and the journey from startup to scale up to public company.
0:02:51 It’s a remarkable journey and I was on that journey for about 17 years and a couple years ago.
0:02:59 I stepped out of that journey, Shane, in a relatively dramatic way and you may have heard
0:03:06 this story before. I was snowmobiling up in Vermont and I was taking a snowmobile from
0:03:12 Rangewater, Vermont to Woodstock, Vermont, coming to the parry part of the trail
0:03:21 and went up over a lip and went down on the other side and just completely lost gravity,
0:03:28 went straight down up a cliff and smashed at the bottom. The snowmobile was in about a million
0:03:37 little pieces. I was passed out for a long time and then I woke up, it was about four in the afternoon.
0:03:45 It was quite cold and nobody knew where I was. Confident I was going to die and I sat there for
0:03:53 a good hour thinking about, you know, if I do make it through then what? And I never bring my phone
0:03:57 when I snowmobile because in Vermont there’s no signal, all darn state there’s no signal,
0:04:01 but an hour in I’m like maybe I’m on it. It turns out I brought it like a moron
0:04:09 and I checked it and dialed 911. Shane, have you ever dialed 911? I have, yeah. It’s an amazing
0:04:16 service. If that was a start-up I would be thrilled to invest in it. It’s amazing. The woman was sort
0:04:25 of very, very good at it and she says, I remember she said sit tight and mind you I have, I’m a mess,
0:04:31 many, many, many broken bones. And so it’s like, yeah, I’m not going anywhere. And then she called
0:04:37 the two local fire stations and they’re volunteer and there’s no one there and so then she has to
0:04:42 track down the mobile phone numbers of all the firefighters and the rescue people, call us them
0:04:46 at home. They hop in their snowmobiles and they come and find me. By the time they found me,
0:04:53 you know, it’s pitch black, it’s really cold out and basically they went to work on me. I kind of
0:04:58 put Humpty Dumpty kind of back together on the side of the mountain, towed me to a flat area
0:05:03 which is two miles away, helicoptered me to Dartmouth University and there they really
0:05:12 put Humpty Dumpty back together over lots of surgeries a lot of time. And I remember that
0:05:19 because that was the end of my CEO journey. I had been quietly saying to myself that I didn’t love
0:05:26 being CEO of a spot, frustrated with just the core work. And I remember saying to myself at the
0:05:33 bottom of that cliff, I make it out, I’m not coming back. And so I was out of work, a terrific woman
0:05:39 took over for me. It’s a funny story about that while I was gone. And as I got back on my feet,
0:05:43 everyone just assumed I was coming back like, no, no, no, I’m not coming back. You’re doing a great
0:05:48 job. You got this. And I actually think a lot of CEOs would be a lot happier if they did something
0:05:56 similar like that. Not some real part. I assumed, yeah. What went through your head when you sort
0:06:01 of couldn’t move? You’re stuck in the snow. And you couldn’t contact anybody like what are the
0:06:06 thoughts that we’re going through your mind? I’m not super comfortable telling everyone all my
0:06:13 thoughts on this, but a lot of thoughts around if I make it out of this somehow, someone finds me
0:06:22 randomly, what’s going to change? But then I mean, the net net of all of them is life can be very
0:06:30 short, very short. You never know what will happen. And don’t waste it. Don’t waste time doing something
0:06:37 that doesn’t make sense for you. You know, refactor your life. And I refactored my personal life and
0:06:43 I refactored my professional life pretty dramatically. And these days, I really don’t do anything I want
0:06:49 to do. And I wanted to do this podcast. It’s a really good podcast. Thank you. Tell me about
0:06:55 what the changes were. Like, were they all at once? Were they slow? Like, be specific or bear?
0:07:02 Sort of. I always wonder this because I had a near death experience to you a couple years ago.
0:07:09 And I remember pondering life and thinking about, oh man, if this is the end, like, did I spend the
0:07:15 time the way that I wanted to? And if it’s not the end, like, what is it that I really want to
0:07:21 change in life? And what impact will that have? And I’ve done such a better job of sort of taking care
0:07:27 of my body and my mind and sort of self care, if you will, just as a big word to encapsulate that.
0:07:34 I changed a lot of relationships in my life. I sort of invested in some and then I wouldn’t say
0:07:39 broke off some, but definitely stopped investing in some. And so I’d love to hear about the specific
0:07:44 things that you did that you sort of were like, okay, well, this is this is the realization.
0:07:52 It’s exactly like that. When I say refactor relationships, I triple down on family relationships.
0:07:58 I’m gonna say ended relationships, but I certain people that didn’t give me energy in certain
0:08:04 ways and just stopped engaging with. And it’s a much smaller group I engage with these days.
0:08:10 Professionally, I stopped my main job. I mean, I founded HubSpot 17 years earlier. It was kind
0:08:17 of my life and everything was sort of wrapped up in it. And now chairperson some small but
0:08:24 not in the day to day. I got obsessed with maybe similar to you with longevity, like, well, if
0:08:31 I’m going to live to 8590, I want to be very strong living to 8590. So basically anything
0:08:37 Peter Atea or Andrew Huberman said to do, I did, except they drink a little, but I basically do
0:08:42 everything they do lost a lot of week, got much better shape. And so lots and lots and lots of
0:08:48 changes. But I think the macro one was just love your family, tell your mom you love her,
0:08:54 hug your kids at one more time today, and don’t waste time. You know, do things that really
0:08:58 are rewarding to you. One of the big things for me was like just being home for the kids every
0:09:02 day after school, I just made a commitment. I was like, I’m going to be here every day when they get
0:09:07 home. I’m not going to push it at the office a little longer. I’ll find other ways to do that
0:09:12 because I’m also sort of balancing ambition and all this other stuff. But it wasn’t going to come
0:09:17 at the expense of that time with them that I know, inevitably I’ll look back on and be like,
0:09:21 man, I just wish for, you know, a little bit more cookies and milk. And they say the dying
0:09:26 wish of every man if they just want another day. And I think about that a lot, like what am I going
0:09:31 to wish I had done being in my life. So Sheen, while we’re on this, why don’t you tell us what
0:09:36 happened to you? I didn’t know for a long time what was happening to me. I just had symptoms
0:09:41 and they kept getting worse and worse and worse. And so like, I had a fever, then I had an earache,
0:09:46 and this was during COVID. So everybody thought it was COVID. So I went to the doctor
0:09:49 and they were like, oh, you don’t have an ear infection, you’re fine, you don’t have COVID,
0:09:56 go home, suck it up. And then I woke up on a Saturday. And I remember just making a latte,
0:10:03 and then I was drinking it and it spilled down my chest. Okay. And I was like, what the heck?
0:10:08 I’ve been drinking out of cups since I was like two, you know, rarely do I spill something.
0:10:15 And I went to the bathroom and I looked in the mirror and the left side of my face was 100%
0:10:21 paralyzed. And so I had no movement whatsoever. I felt like I was moving things. But like,
0:10:27 if I raise my eyebrows, like you can see now on YouTube, if I raise my eyebrows, this, it was
0:10:32 actually kind of beautiful in hindsight, it was freaky when it was happening. Because this, and
0:10:37 it just didn’t move. And I was like, Oh God, like I got to go to the doctor. My first thought was
0:10:41 actually not to go to the hospital, which is a little weird. So I show up at my former family
0:10:47 doctor’s office on the weekend and they’re like, you need an appointment. It’s Saturday.
0:10:51 And I was like, well, I can’t move my face. So I think that qualifies as like, maybe I get an
0:10:57 appointment today. And she’s like, Oh my God, yes, you see the doctor right away. I go into the doctor.
0:11:01 And she’s like, I think you’re having a heart attack. And I was like, well, this doesn’t make
0:11:08 a ton of sense, right? Like, maybe, I don’t think that’s the case. However, you’re the doctor,
0:11:12 I don’t know what I’m talking about. And she’s like, you need to drive to the hospital. I was like,
0:11:16 well, if you think I’m having a heart attack, why are you telling me to drive to the hospital?
0:11:21 Yeah, it was like, these two things don’t align. Anyway, I go to the hospital, I see a doctor right
0:11:25 away. I mean, for all of the knocks on Canada’s healthcare system, there’s certain things in
0:11:30 triage that they definitely see. I saw a doctor probably within three minutes of getting to the
0:11:34 hospital. And, you know, he’s like, you’re not having a heart attack. It was like, thanks. And
0:11:39 then it’s like, go sit and wait for like 12 hours. Well, we handle all the other urgent people,
0:11:43 which is fine. And so he sees me and he’s like, I’m going to give you some pregnant zone. And
0:11:49 you’ll be fine. And I remember going like, wait, what? Like, you’re just going to give me some
0:11:54 steroids and like send me home. Like, nobody cares about how this happened. I’m a healthy at the
0:11:58 time, 42 year old male. I’m not overweight. You know, I don’t smoke. I don’t excessively drink.
0:12:03 I have nothing that would sort of indicate this. When I was in the waiting room for the 12 hours,
0:12:07 I started talking to a whole bunch of neurologist friends and they were like, you should get tested
0:12:16 for these four things. And it was like HIV, Lyme disease, mono and something else. And I was like,
0:12:22 can I just get a requisition to get tested for this? And he’s like, no, it’s just like a waste of
0:12:26 the medical system. Oh man. And I was like, wait, what? Like, that doesn’t make sense. He’s like,
0:12:30 go talk to your family doctor. They’ll figure that out. I got to go help out their patients.
0:12:34 How’s your faith at this point? Well, it’s still paralyzed, right? So he’s like,
0:12:38 you’re going to recover. He’s like, you have a 99.8% chance of recovery. I’m like,
0:12:42 I’m not worried about recovery. I’m worried about what caused this, right? Like, before we figure
0:12:48 out the future, we have to figure out like, what am I doing something? I need to stop. And
0:12:53 I went to my doctor on Monday and I was like, Hey, can I get a requisition for these blood tests,
0:12:57 which in the States, you just show up and do it. And in some provinces in Canada,
0:13:01 you can just show up and do it too. But in Ontario where I live, they won’t allow you to do that.
0:13:07 You need a requisition. Anyways, she says no for whatever reason. She’s like, if the ER doctor
0:13:12 thought you needed it, he would have given it to you. Please, please fuck off politely is sort of
0:13:16 what she said. And I was like, well, this is so weird. And I’m like thinking about this. And then
0:13:21 I wake up a few days later and I can’t stand. Oh man. So the backs of my knees,
0:13:26 like if I’m moving, I’m fine. But if I stand still for like 10 seconds, I’m literally crying.
0:13:30 There’s tears coming out of my face. I’ve never been in so much pain. It’s like somebody stabbed
0:13:36 the back of my legs with a knife. And I was like, wow, this is like so crazy and up like emailing
0:13:41 my doctor again. I’m like, I really think I should get tested for a whole bunch of stuff at this
0:13:45 point. Like, I don’t know what’s happening. And she’s like slow knowing me. She’s like,
0:13:48 it’ll get better. Just give it some time. And then like three or four days later,
0:13:54 I wake up and I can’t open my mouth. Like I have a lock job, basically. I can open it like a
0:14:00 centimeter. And luckily to cut a long story short, I end up talking to a close friend of mine
0:14:04 who happens to be an eye surgeon. She’s like, I’ll give you the requisitions.
0:14:11 She gives me the requisitions. I test positive for Lyme disease. I start the treatment for Lyme
0:14:16 disease because when you test positive, you can actually, you can fix it. And so I start taking,
0:14:21 I think it’s doxycycline, the antibiotic, which is the treatment for that and instant
0:14:26 improvement. The cool part of this is I saw a neurologist, who tested me for like 200 different
0:14:31 things. You know, I went down to give blood and the ladies like, this is the maximum blood we’re
0:14:38 allowed to take out of you. I was like, oh, this does not sound really good. And I came back completely
0:14:43 normal aside from the Lyme disease. So I’m glad we caught it. Glad we solved it, you know,
0:14:49 made a lot of changes after that. I want to go back to you and HubSpot though. So like you’ve
0:14:56 been on this journey for a long time from startup all the way to scale up to now public company,
0:15:02 sort of chairman, walk me through the different phases a CEO goes through. I personally break
0:15:12 them out like two to 20 employees, 20 to 200, 200 to 2000, and then 2000 plus. And I kind of
0:15:19 grate myself in these seasons. Like, I give myself a B in two to 20, like two to 20, I was doing
0:15:25 customer development, I was the lead user of the product, I was marketing it, but I’m a crappy
0:15:33 coder. And so the heavy lifting was really done by my co founder. 20 to 200. I was kind of in my
0:15:42 element. I loved it. I was in a 200 to 2000, maybe a B, and then 2000 to 2000, maybe a D. I
0:15:48 really didn’t like the work. And I think that’s the case with a lot of CEOs and a lot of executives,
0:15:53 a lot of people like people have a season that they enjoy and they get good at it. I think
0:15:58 that’s very much the case for me, which was the one where you felt like you had to grow the most
0:16:06 to fulfill the role really through the whole thing. I fell under qualified to do it. And
0:16:14 I don’t know about you, but I still have imposter syndrome here on the podcast. And I had it
0:16:18 throughout. I think one of my superpowers actually is I’m a learner and I try to get better and I
0:16:25 listen to other people and I take feedback pretty well. And we had a mechanism that was quite good
0:16:30 for giving me feedback. Really good, actually. My co founder was responsible for my annual 360
0:16:35 review. He’s super introverted. So he didn’t want to go around and talk to other people.
0:16:41 So he sent a net promoter survey out to the board, the execs, customers, all bunch of people,
0:16:45 30 different people. He got a lot of responses, maybe 25 responses. And there were two questions,
0:16:52 Jane. One was on a scale of one to 10, how likely you refer Brian as CEO of HubSpot? And two,
0:17:00 why did you give that answer? And people wrote novels about it. And it’s hard for CEOs to get
0:17:05 feedback, very hard. Very few people get straight feedback to the CEO. So this was a good way to
0:17:12 get the end was big enough that people gave very, very strong feedback. And he summarized to give
0:17:20 me my net promoter score. And then I started reading my review. And each page was different.
0:17:23 So the first several pages were my features and he’s a software developer. He’s like,
0:17:28 here’s your features. So page number one, you’re very good at explaining HubSpot’s vision. And
0:17:35 then he pulled out quotes from the novels people wrote. Page two, page one through 10 were features.
0:17:40 And they were great. And I was pretty confident that I was the best CEO ever invented after
0:17:46 reading for Sunday. And then the bugs came. Page 11 was the bugs. And there were 12 pages of bugs.
0:17:52 And I was pretty convinced I was the worst CEO ever invented by the end of the 12 pages. And I
0:17:56 remember when I finished it, I’m not a Scotch striker. So I remember I poured up class of Scotch.
0:18:05 But that mechanism for getting feedback was we still use it. So the current CEO gets the same
0:18:12 type of a thing. And it’s very, very, very useful. I think founder CEOs often have this problem
0:18:17 that like, founder CEOs like to make decisions, like to be involved with the details, like to
0:18:22 drive things, like to be in the middle of things. And that’s a great strength when you get 10 people.
0:18:27 But that great strength you have turns into your greatest weakness when you have a thousand people.
0:18:31 You’re trying to manage everything, trying to manage your way to know everything that’s going on.
0:18:36 And so the consistent feedback was like, how do you get yourself out of the details? How do you
0:18:39 stop working in the business? How do you start working on the business? That was kind of a
0:18:46 common thread that I worked on across all 17 years. Was that feedback enough for you to walk away
0:18:51 going like, okay, I see this, people are giving me feedback, I accept it, there’s some truth to this?
0:18:58 Or was there a part of you that was like, no, they’re wrong? It was pretty, pretty accurate.
0:19:03 And I’m shaking my head through most of it in the software business. Sometimes there’s something
0:19:09 that someone thinks is a bug, but it’s a feature to somebody else. So some of my bugs, I actually
0:19:14 thought were features. Like, I can be really passionate about something. And probably get
0:19:21 so passionate, it’s like a little scary sometimes. I’m like, fine, if like two out of 30 of you think
0:19:25 that and the rest think it’s a good thing, I can live with that. So there were several things that
0:19:30 I was like, that’s a bug that I can live with. And every year I try to work on one or two of the bugs.
0:19:35 If I put 10 calories and try to improve the feature, I get like a thousand out. And so
0:19:41 I more paid attention to the features and tried to get better at the features. And this took me a
0:19:46 while to figure this out. And over time, just tried to hire people around my weaknesses. And I have
0:19:51 plenty of them. I really looked at hiring the best I could in the areas where I was weak,
0:19:56 rather than trying to become an expert at it. And I’ll give you one area where I made a mistake
0:20:02 on this. In the early days of HubSpot, I fashioned myself like a great product designer. I don’t
0:20:07 know why I did. I think basically, because I followed Steve Jobs, everything he did,
0:20:13 read every book about him, watched his keynotes, and obsessed with him as CEOs are my era.
0:20:18 And I was like, I can do that. I can figure it out. I took classes and I really dug in.
0:20:24 For years, I was convinced I was a great product designer. I’m not. I just don’t have that genetic
0:20:32 code. I was actually quite bad at it. It took a while before that feedback sort of hit me
0:20:36 between the eyes. And we started hiring people really good at it and enabling me to let go of it.
0:20:41 What are some of the lessons you took away from your sort of studying of Steve Jobs,
0:20:48 if you will, that you used effectively? One of my favorite things on the Interwebs
0:20:52 is his keynote. And his commencement speech at Stanford, I think, is quite good.
0:20:58 And once I’ll look back at that, he was faced with cancer. And the way he approached that was
0:21:05 really interesting. And he says it in a different way, but he didn’t waste any time. That’s for sure.
0:21:11 And then HubSpot a lot is based on his work. We started the company out of Sloan, while we were
0:21:15 business school. And at Sloan, they did field trips. And we did a field trip to the West Coast.
0:21:21 And I remember this one day was a really good day. In the morning, we visited Apple. It was like a
0:21:27 year after the iPod came out and it was on fire. And I remember Steve walked into the auditorium.
0:21:32 It was about 100 of us. And he was in a bad mood. And it was pretty intimidating.
0:21:37 And I remember he looked, he looked out and he basically was like, what are you people doing
0:21:41 here for business school? Like he wasn’t into the whole business school thing. And one of my
0:21:46 classmates, JP Gorski, raised his hand up high and he said, we’re here from Sloan School of Management
0:21:50 and we’re studying innovation, disruption. And we thought we’d learn from the best.
0:21:55 And as Steve just melted, he liked that a lot. And then he talked about how we came up with the
0:22:01 iPod. And kernels of this very much made it into the way we thought about HubSpot. And the iPod,
0:22:06 the way he described, was really simple. There were MB3 players before, but you had to be a real
0:22:11 geek to use one. And very few people were buying them. And you had to burn music to them as a pain
0:22:16 in the neck to do it. And he said, I really wanted something simple. So I wanted to take an MP3 player,
0:22:22 build a freemium app, iTunes, and then work with the record company, enable you to download a song
0:22:28 for 99 cents a song. And he said, that’s a one plus one plus one equals 10 for the consumer.
0:22:33 And that was how we originally came up with HubSpot, like a marketer in that day and age,
0:22:38 putting Google Analytics and a blog, social media tracking tools and SEO tools and marketing
0:22:44 automation, CRM and all this stuff. And it was complicated, big, hairy problem. And so we used
0:22:50 that analogy very much that Steve used, like, how do we make an all one system where the one plus one
0:22:56 will equal 10 across all systems. So the morning was really influential. And then that afternoon,
0:23:02 when kids were in business school, we visited a little startup called Salesforce.com and their
0:23:07 CEO, Mark Benioff. And so that day was really formative and thinking about HubSpot.
0:23:12 Oh, that’s crazy. Had you guys just taken your tuition and invested in both of those companies?
0:23:15 I know. That’s a good point.
0:23:22 That’s crazy. So you started it in school. How did you learn how to hire and fire people?
0:23:26 Like, how do you know you have the right fit? How do you know when it’s time to move on from
0:23:31 somebody? You know, I think about that as somebody who went from school to a large corporation,
0:23:35 and they have all these policies and procedures in place. And then now as an entrepreneur,
0:23:42 I’m dealing with CEOs all the time. We’ve never really hired and fired. And I’m curious as to what
0:23:47 wisdom you can sort of pass on to people. Most CEOs, including myself, are quite bad at this.
0:23:56 And I’ve identified some things that may be useful hacks, may not be useful hacks.
0:24:01 This is also a seasoned thing. If you’re hiring someone when you’re 200 employees,
0:24:05 I’d see the mistake everyone makes, and we made the mistake over and over and over and over and over
0:24:10 again, that if you’re hiring someone that you want to go from two to 2000, you’re just really
0:24:16 attracted by that person who came from Google or Microsoft or whatever huge company with a huge
0:24:23 resume and all that stuff. And once in a blue moon, that’ll work. But generally, that’s a failure
0:24:30 condition. If you hire the press release hire that said a couple of phases over you. I don’t think
0:24:34 it normally works. Same thing for board members. My analogy for being a CEO is like you’re an
0:24:41 ice climber going up the ice, and it’s treacherous, and you can easily slip. And what you’re looking
0:24:46 for are executive members who have been up that same sheet of ice, but in the last three or four
0:24:52 years, what you don’t want is somebody who’s 20 years over you, or someone who spent their whole
0:24:57 career on top of the hill looking down on the ice climbers, you want somebody just a little bit
0:25:00 ahead of you on that ice climbing mission. So that’s one thing I think people get wrong.
0:25:08 I also think I think most people are bad interviewers, including myself, like I’ve missed a bunch.
0:25:14 And I think the core reason for that actually isn’t the interview, it’s interviewees,
0:25:21 interviewees are so good in interviewing, you’re interviewing a VP or a C level person for
0:25:28 company like HubSpot. They’re good at interviewing. And if they’re not, they’ve been coached, they’ve
0:25:34 looked on YouTube, like, I just think everyone, including myself, overvalues their ability to
0:25:43 select talent in the interview process. I see that as a overconfidence. I think also like they
0:25:48 see it with the CEOs I work with, and I see it as companies get bigger, like you’ve got a panel of
0:25:55 four people evaluating Shane as a potential VP. If all four people like Shane versus two people
0:26:00 love Shane, two people are like, I’m not sure about Shane. You always go with the person
0:26:04 with the least amount of weaknesses and that lowest common denominator higher. I think that’s
0:26:11 a failure conditions. We’ve noticed that over time, I take two loves and two mezz over three
0:26:18 likes. I think that’s a best practice that people should be doing. And I think people should be
0:26:22 obsessed with reference checking. And yeah, calling the references, getting good at that,
0:26:29 getting good at finding people in your network. I would guess I’ve coached tons of CEOs on average
0:26:34 for every director VP, C level person that’s hired within 18 months, they’re gone.
0:26:39 How do you know when it’s time to move on from somebody? I guess in a way, you’ve either made
0:26:44 the wrong hire or it’s the wrong environment for that person to succeed or however you want to
0:26:49 phrase that. But how do you recognize that? I had a CEO the other day tell me is like the moment
0:26:54 you start thinking about it, that’s the moment to act on it. I’ve never seen anybody change
0:26:59 their mind from that initial thought. How do you think about that? What’s your reaction to that?
0:27:05 Unfortunately, I feel like that’s conventional wisdom. And I think it’s largely puts with what
0:27:12 I’ve seen. I rarely change my mind on people in that kind of context. And everyone says,
0:27:18 when you know, you should move quickly. I never had it call me weak.
0:27:24 Have you ever regretted not moving quickly? It’s sort of interesting to contrast that to
0:27:29 sort of like Jensen, who’s been talking recently about, you know, he doesn’t really fire people,
0:27:35 he sort of like berates them into being better in a public way, berate is probably the wrong word,
0:27:40 but he sort of wants to pull you towards excellence rather than fire you. But I don’t
0:27:45 think that’s practical for most people or most organizations. So you and I both sat through
0:27:51 the same Jensen presentation. Yeah. So it’s been a lot of time thinking about CEOism and coaching
0:27:58 CEOs. And there’s sort of like a set of best practices for being a CEO is almost like a CEO
0:28:03 unofficial school. What’s confusing about the CEO school that’s been around for a long time
0:28:14 is arguably the two, I’m not going to say best, but two amazing CEOs are Jensen at NVIDIA in Elon,
0:28:25 at SpaceX, etc. And they completely ignored almost everything about CEO school, CEO lessons,
0:28:32 CEO best practices. And I find that fascinating. Talk to me about that, right? Where maybe there
0:28:37 is no model, we hold up this model, we teach it, it’s easy to do. We say the right things,
0:28:42 but in reality, the people that end up changing the world are often the opposite of all of the
0:28:47 points that we teach. Berkshire Hathaway, for example, if you looked at their board of directors,
0:28:52 I don’t think they pass any of the sort of like standards that business schools would set for what
0:28:58 an independent board looks like. And Constellation Software is another example of that. So with
0:29:03 Shopify, all these companies that have sort of done these remarkable things, they don’t look
0:29:09 anything like what we’re taught in business school. When I was maybe like 50 employees, Shane, I joined
0:29:15 the CEO group. And I largely joined the group because I respected one of the CEOs and I got him
0:29:22 Colin Engel. And Colin made the room of vacuum cleaners that I robot. And I might describe my
0:29:29 relationship with him in two words, man crush. I was a fan of Colin’s. And I remember this first
0:29:36 CEO group, we met all day, once a quarter. And there’s a couple funny things about the CEO group.
0:29:44 But I joined, I sure were spending some time with these 10 CEOs. And two were kind of,
0:29:48 they’re quirky is the way I would describe them and very unique personalities. And the other were
0:29:55 like central casting, blue blazer, tan pants, like really central casting backgrounds and
0:29:59 everything. And they acted what I thought CEOs were supposed to act like. And I kind of acted
0:30:03 like that back then. And when I looked at the numbers, we all showed each other your numbers.
0:30:07 The two quirky founders CEOs were crushing it and the eight central castings were with a,
0:30:13 and I was like, enough with trying to be central casting, I’m going to be exactly who I am. And
0:30:18 we’re going to make everybody else work around who I am. And it’s a lot easier being who you are
0:30:23 than somebody else. Everybody else has taken that was when I was like, I’m quirky too. I don’t
0:30:28 care that I’m quirky. I’m just going to lean into my quirkiness and be myself. And I’ve sort of been
0:30:34 that way ever since. And I don’t think there’s a profile of CEO. You’re talking earlier, how you’d
0:30:40 love to hire somebody with two, I love this person and to Matt, is that because of that? Because
0:30:44 the person who says all the right things, everybody’s going to be okay with. But the
0:30:48 unconventional person, you’re going to get really too extremes, you’re going to get love or hate.
0:30:53 I think what happens as a company scales is you hire for a lack of weakness,
0:31:00 not for spiky strengths. And that’s institutionalized in the scale ups,
0:31:05 interviewing, panel and process. And I think that’s a mistake. And that’s one of the few things
0:31:11 that leads to really mixed success in hiring execs in these companies. Who do you think is
0:31:20 the most underrated public company CEOs? I think the guy running Uber has done a nice job. That was
0:31:27 a very, very, very difficult thing he took over. He got profitable. I think he’s done a really,
0:31:35 really nice job, very quietly done a very good job. How about you? Oh gosh. I think Toby is massively
0:31:39 underrated. We were sort of talking about him during the break here. What are your thoughts on
0:31:44 Toby? Toby reminds me a lot of Colin Engel, actually, just whip smart. One of the things
0:31:51 I like about Toby and Colin is they’re very first principles thinkered. They don’t care to receive
0:31:56 conventional wisdom. They’re going to think it through and scratch. And sometimes you’re going to
0:32:00 get it wrong. But a lot of times they’re going to get it right and do something really innovative
0:32:06 and smart. Toby’s got so much right. He’s got some big stuff wrong. But for the most part,
0:32:10 he’s done a really, really good job. He’s certainly not central casting.
0:32:15 Certainly not. But I think he’s brilliant and a great CEO and he’s running a great company.
0:32:19 I like that term central casting. Another person who stands out to me,
0:32:23 those people are probably familiar with now, but 10 years ago, nobody would have ever heard of is
0:32:30 Mark Leonard from Constellation Software. He’s not really on my radar. Yeah, exactly. I think they
0:32:36 only issued equity at the IPO and they’re, I don’t know, must be $50 to $60 billion company now.
0:32:41 See, I wouldn’t put Toby in the underrated because I rate him so highly and I feel like
0:32:47 people in my circles rate him highly. Yeah, I rate him highly too. And I still think I underrate him.
0:32:52 Okay, got it. Yeah. Yeah, totally. There’s one other interesting thing that’s, I think,
0:32:58 relevant out of that CEO group. I remember going to the CEO group meeting, the first meeting chain.
0:33:07 And what I didn’t realize is there is a topic for the whole day. And one of the quirky things about
0:33:12 HubSpot up into that point is we didn’t have any HR people. We didn’t allow anyone to talk about
0:33:16 culture because we didn’t think we could measure it. It was too squishy. And I remember I arrived
0:33:23 there on the first day. First thing that got put up was the topic of the day and sure enough, I was
0:33:29 culture. And I remember thinking that’s gonna be a big, big waste of time. At least I got to know
0:33:35 my main crush. The whole morning I was pretty disengaged. And then Colin at lunchtime, I remember
0:33:39 if he said to me, it’s like, why aren’t you engaging? You don’t like stopping here? I said,
0:33:46 no, I think it’s a waste of time. He said, Brian, culture, culture is how people make decisions
0:33:54 when you’re not in the room. Culture is how companies really scale. Okay, okay, okay, okay,
0:33:58 got it. And then the afternoon sort of engaged with it. And then the next day he’d go to the
0:34:03 office. And my co-founder, Darmesh says, how’s the, how was it? How’s Colin? Like, how did it go?
0:34:08 I said, it was really, really good. There’s, there’s one, maybe one topic a day. He said,
0:34:16 oh, it’s the topic. I said, it’s culture. Oh, shit, what a waste of time. I said, no, Darmesh,
0:34:22 culture is how people make decisions when we’re not in the room. Culture is how HubSpot’s gonna
0:34:29 scale. And he said, okay, and it’s very hard for me to assign work to my co-founder to this day.
0:34:36 Somehow I assigned him to be the cultures are HubSpot. And he did an excellent job. And still
0:34:41 is doing an excellent job of marshaling the culture from, you know, 15 employees, 8,000 employees.
0:34:47 And he did two clever things. First thing he did is we’re big on net promoter services. He
0:34:51 surveyed all the employees, scale them what to 10, how likely to refer HubSpot as a place to work.
0:34:57 And then why? Again, people wrote novels about it. And he kind of broken all up into,
0:35:04 you know, different topics. And then he wrote a PowerPoint presentation called the HubSpot Culture
0:35:09 Code that basically described the relationship between employees and a company, and just sort
0:35:14 of outlined how we thought about culture. And then he posted it on the internet and it blew up on
0:35:20 the internet. But we continue to do that net promoter score once a quarter for the last 15 years.
0:35:25 And we’re tracking our net promoter score per quarter. And that’s been very, very useful. Then
0:35:31 we post every response to the net promoter survey and culture on the wiki. And then we address the
0:35:36 issues that come up. That best practice to serve as well. Every six months, we refactor the PowerPoint
0:35:42 deck. It’s a living, breathing document. And we basically treat culture like our second product,
0:35:48 like our product HubSpot, if it’s unique relative to the competition, good quality product, and it
0:35:54 delivers value. It’s like a magnet that pulls customers in and retains them. Same thing with
0:35:58 the culture. If it’s unique relative to the competition, it’s high quality and adds value.
0:36:03 It’s like a magnet that pulls in employees and retains them. And so we put a lot of thought
0:36:06 into that culture stuff. And I think a lot about how do you take, how do you go from start and
0:36:11 scale up? I think a key part of that is getting your culture right and writing it down and
0:36:17 institutionalizing it. I’m going to make a statement about culture. And I’d love for you to argue,
0:36:21 take both sides of the debate, if you will. So I’m going to say that culture is the only
0:36:27 sustainable advantage. I disagree. Why? Let’s take Uber. They had a certain culture
0:36:34 Dara, the new CEO, came in. I’m quite sure he made massive changes to the culture the founder
0:36:41 put together. And he thrives. I think some of the benefit, of course, is his culture,
0:36:47 but they had major sustainable competitive advantages in that they had a fleet of drivers
0:36:52 and customers in the network effect and software that works. And he’s probably been there 10 years
0:36:58 and I don’t think it’s all culture. Oh, that’s interesting. So in my mind, I would sort of think
0:37:05 of that more like they had a advantage, like an operational advantage that came from the network
0:37:11 effect and the scale. I don’t know if that would have been enough to sustain it
0:37:19 going forward without the culture. Fine. I sort of agree with that. I think the best example
0:37:25 on the other side of this is Satya. Satya is on my Mount Rushmore CEOs. A lot of people push back
0:37:29 from me. It’s like, oh, I was an founder. You shouldn’t be on there. He’s on there for me
0:37:36 because Microsoft was gone very, very sideways for a long time. And he stepped in and really
0:37:43 did change the culture in a massive company and couldn’t be more impressed with him and the culture
0:37:48 change and how well that works. So that’s my flip side of the argument is Satya. Okay. Who else is
0:37:56 on your Mount Rushmore? Jerry Garcia is on my Mount Rushmore. Great CEO. The app for mentioned
0:38:02 Steve Jobs on there. Why Jerry Garcia? Grateful dead. Really? Why Jerry Garcia? That’s the most
0:38:08 obvious one on there. Why? No, I’m curious. I’m not a Grateful Dead. I don’t think I’ve ever
0:38:12 really sat down and listened to the Grateful Dead, so you’re going to have to walk me through this one.
0:38:19 Okay. Jerry Garcia was the CEO cut in the cloth of Colin Engel and Toby Lukey.
0:38:25 Really disliked conventional wisdom and kind of rethought everything from first principles,
0:38:30 starting with the music. So they started that band in the mid-60s. And at the time, there were all
0:38:35 kinds of rock and roll music, and there was jazz music, country music, and bluegrass music,
0:38:40 and they didn’t do any of that. They created a new genre of music. People refer to it as jam bands now.
0:38:47 But Garcia himself was a bluegrass player, and the bass player was a jazz musician, and the keyboard
0:38:52 player was a blues guy, and Bob Weir, the singer, was kind of a country rock and roll guy, and they
0:38:58 blended them all together, and they infused this jam band mentality into it, and they really stretched
0:39:04 the songs out with improvisation. So they sort of rethought the genre and made a new type of music.
0:39:11 The product was unique, and the go-to market was exceptionally unique. If you think of, like,
0:39:16 when I was in high school, if I wanted to go to a Rolling Stones concert, I would call Ticketmaster,
0:39:22 and I would wait till whatever it is, 1.30 on a Tuesday, and the Rolling Stones tickets were on a
0:39:26 sale, and I would dial away. I’d be five minutes late, but I’d dial away, and I may or may not
0:39:32 go through. The people who ended up buying most of the tickets were the scalpers. The scalpers had a
0:39:38 whole bunch of people buying the tickets that sold the tickets in a markup, and so the front row of
0:39:43 the Rolling Stones concert was a bunch of bankers of venture capitalists, people who could afford
0:39:48 the tickets, and the people didn’t like anything about that, Shane. Nothing about it. They particularly
0:39:53 didn’t like a bunch of bankers and venture capitalists in the front row of their concerts. They wanted
0:39:59 their hippy, crazy fans in there. They also didn’t like the distribution set up, so it was grateful
0:40:05 then, and then Ticketmaster took their slice, and then scalpers took their slice, and then the fans,
0:40:09 so they said, “We’re going to disintermediate,” just like the internet did to so many things.
0:40:14 “We’re going to disintermediate those two layers, and we’re going to sell tickets directly to customers.”
0:40:19 The way they did it was you listened to a 4015 recording that explained what was going on,
0:40:24 and the way, Shane, you would buy the tickets was you have to put a three-by-five card,
0:40:28 which concert you went to. You can only buy four tickets per concert,
0:40:34 okay, so the scalpers are less incentive, and then you had to go to the post office to get a
0:40:38 postal money order, so just a total pain in the backside to get a postal money order,
0:40:42 and then you had to put a self-address down down below, and then you put your regular envelope
0:40:48 and mail it in. Now, how would the grateful then, Shane, decide who gets the front row seats?
0:40:49 I have no idea.
0:40:53 The way they sort of did it was that self-address, they have the envelope,
0:40:58 the more beautifully you could decorate it with dancing bears and mushrooms and sprinkles.
0:41:00 I love it.
0:41:04 Yes, so they solved a bunch of problems. That’s not the end of it.
0:41:06 What was the last concert you went to, Shane?
0:41:08 Oh, God, it’s been a long time.
0:41:09 Did you go to Taylor Swift?
0:41:12 No, I am a Taylor Swift fan.
0:41:15 Okay, let’s just say you went to Taylor Swift in Ottawa.
0:41:20 And you showed up with your giant camera in your boom microphone,
0:41:24 and you showed up there. What would have happened at the gate?
0:41:25 They wouldn’t let me in.
0:41:27 Why? Why didn’t she want you recording?
0:41:30 It might affect other people’s experience if I have a boom mic.
0:41:37 You can’t prevent people from recording on their phones, so at some degree, they’re accepting it.
0:41:42 The NBA actually went through this a couple years ago. They were trying to really block
0:41:47 people from posting clips on social media. Then they actually embraced it, and it changed the
0:41:53 whole league. It got way more people. Sorry, this is a sidetrack to this, but that change
0:41:57 in the NBA really changed the NBA.
0:42:02 Okay, pre-iPhone, let’s say you were going to a Rolling Stones concert,
0:42:04 and you had all that equipment you were walking in. Of course, they would block you.
0:42:09 And the reason is you see the Rolling Stones in Boston, in New York, and then Philly, and then Miami.
0:42:14 The exact same concert. They don’t miss a note. They’re fantastic.
0:42:15 Same thing.
0:42:19 When you walked into the Grateful Dead with your big boom mic and your big camera,
0:42:23 they put you right in the Taper section, the perfect spot to watch the concert.
0:42:27 They said they did a tape it, and you taped it, and then you went from Boston,
0:42:30 then you went to New York, you taped it, you went to Philly, you taped it,
0:42:34 then you went to Miami, then you get back to your dorm room, and you copied as many tapes as you
0:42:38 could of the best concert, not the worst concert, and you gave them out to all your friends.
0:42:46 And that was how they market. They gave away the content. They were the first in-down marketers
0:42:51 to really nail that. They were the first real freemium model. They were the first viral marketers,
0:42:56 and the way they did it was brilliant. And it worked for them because every concert was quite
0:43:01 unique. They’re a jam band, so they never played the same set list twice, and so there was an
0:43:06 incentive for knuckleheads like me to go from Boston to New York, up and down these coasts.
0:43:11 In fact, I did that last week, I was at the Spear, and I saw them Friday, Saturday, Sunday.
0:43:17 Garcia was a genius. He’s a marketing genius, actually, and I think he’s a music spot.
0:43:25 That’s fascinating. I’m going to have to listen to The Grateful Dead now. I wrote a book on this
0:43:29 called “Marketing Lessons from the Grateful Dead.” We started talking about inbound marketing there.
0:43:36 I’m curious as to, you guys pioneered inbound marketing to a big extent, and definitely got
0:43:42 the momentum rolling there. How has that changed in the past few years, and where is that going in
0:43:48 the next few years? Ironically, I think it kind of went out of favor a bit over the last few years,
0:43:54 and I think it’s about to come back in favor. The things that change about it aren’t that different.
0:44:03 Instead of cold calling people, and spamming people, and advertising people, and renting space
0:44:08 on YouTube, or renting space on your podcast or your blog, or renting space on New York Times.
0:44:12 Spray your own New York Times, draw a podcast, and become your own publisher, and then pull people
0:44:19 in through Google and search and other social outlets. It works very, very, very well. You’re
0:44:23 living proof of how well it works. The things that have changed, or the social media networks
0:44:26 have changed. When we first wrote about this, before we started HubSpot, we started writing
0:44:32 about inbound marketing. Dig and Reddit were the two big social media sites. I don’t think
0:44:36 things around in Reddit have gone through all these iterations, but obviously it was Facebook,
0:44:42 and now it’s TikTok, it’s Instagram. It’s all these new social media sites. It’s YouTube. People
0:44:49 live in YouTube. It’s podcasts. The medium isn’t necessarily a long-form blog like it was back
0:44:54 when we started HubSpot. It’s videos, a lot of short-form videos, and so that’s changed quite a
0:45:02 bit. I think what’s interesting about what’s going on now is today you go to Google and you get your
0:45:09 10 blue links. If you look across our customers, that’s 62, 63% of the inbound traffic is via Google,
0:45:14 and most of it’s organic. I think over the next five years, that’s going to change a lot. I think
0:45:17 Google’s going to have to change a lot, and I think people are going to spend more and more of their
0:45:23 time inside ChatGPT, and they’re all ChatGPT’s competitors. I think when you’re engaging in
0:45:27 that way and you do a search in ChatGPT for, let’s say, HubSpot, it will tell you about HubSpot,
0:45:30 and then you’ll say, “Well, how does HubSpot compare to Salesforce?” It will tell you about that.
0:45:35 How much does HubSpot cost? It will tell you that. People know a lot about HubSpot.
0:45:38 One of the brilliant things about Google is their blue links, and they didn’t mind sending you
0:45:42 off their website. It’s a very counterintuitive idea. I think that’s going to start changing as
0:45:47 consumer behavior changes, and I think be a really interesting to see how it evolves.
0:45:52 Do you think content is just going to get overwhelming? I mean, you can create content
0:45:58 with two sentences now. You can create blog posts that would rival probably the best people we’re
0:46:03 putting out maybe 10 years ago with almost no effort whatsoever.
0:46:09 I think you’re right, and I think it’s not just that, but it’s going to be e-mails. I think that
0:46:15 the robo-emailing and the BDRs, I look at lots of startups in the CRM phases, might imagine, but
0:46:24 there’s about 48 startups building automated AI agents. I still think having a unique perspective
0:46:30 and a unique personality is going to work. I don’t think your podcast goes away because
0:46:35 I start something that sounds like you, and I use an avatar to deliver it. I think something
0:46:40 what you’re doing will last the test of time. I think a lot of people, particularly in scale-ups,
0:46:44 run away from their personality. They make it generic, and you have a certain vibe and
0:46:49 a certain personality. I think that works for you, and it’s going to be very hard to replicate.
0:46:54 Quality and uniqueness never go out of style, and I think you’re going to be increasingly
0:46:59 important as you just fill content that’s AI generated. It’s almost what you said before,
0:47:04 like lean into your individual quirkiness, and your tribe will find you and then go around with you.
0:47:08 Although you have me worried, we’re almost a million people on our newsletter now. I’m like,
0:47:13 “Oh God, if this is going away, I got problems.” I also think we’re going to see the trend,
0:47:16 and I’m certainly not the first person to say this, but I think you’re going to see
0:47:21 a lot more small big companies, and you’re going to be able to get a lot more done with a lot less
0:47:26 people. I don’t think in a billion dollar company, you’re going to need three, four,
0:47:31 five hundred person marketing organizations. I think the new tools are coming out, including
0:47:36 Upsplot Stoles and CRM Suite. I just see how incredibly powerful they are. I think you’re
0:47:42 going to be able to scale in a whole new way. I think the AI revolution, when it comes to
0:47:48 inbound, I think top of the funnel gets more difficult. I think middle of the funnel gets
0:47:54 easier. Really high quality personalization on your website, on chat, on everything, that gets
0:47:58 much more powerful. Top of the funnel gets more difficult. I think inbound’s going to change,
0:48:03 but I also think inbound is going to make a comeback. How do we do outreach in a world of AI
0:48:08 and in a world where people are bombarded with, is it going to be freemium and then pulling people
0:48:12 in through that and the outreach is letting them know about the freemium stuff? You’ve got to get
0:48:17 good at the branding thing, again, it turns out. Because getting into your or my inbox is going
0:48:22 to become exceptionally difficult with all the changes Google’s making to email that’s getting
0:48:27 part or as it is, but the robo emailing is going to go wild and the robo content is going to go
0:48:32 wild. It’s a little more around branding. You have to be good at everything. It’s like a baseball
0:48:36 5-2 player. You have to be getting found in YouTube. You have to be getting found in all the
0:48:39 social sites. ChatGBT’s going to understand you perfectly well. Google’s going to understand
0:48:43 perfectly well and you need people tripping over your all over the place. I think people have to
0:48:46 get comfortable with the fact they’re going to have less new visitors to their website because
0:48:51 ChatGBT and their ilk are going to know so much about you and not have those lists of blue links.
0:48:55 They’re just going to live on there and learn so much about you. And then when someone’s quite
0:48:59 serious, they end up on your website and you have to get very good at personalizing that
0:49:05 website experience. I also think people are going to end up keeping more information behind
0:49:11 the paywall and the login wall on their websites because they want to keep a little bit back from
0:49:15 ChatGBT because ChatGBT is going to understand the public stuff so well. I think it’s going to
0:49:20 change in a good way though. I guess the baby step that Google made on that was like when they
0:49:26 would just show you the excerpts. If you asked a question, it’d be like basically giving you a
0:49:31 link but it’s really hard to find. It’s like here’s the answer to your specific question.
0:49:38 YouTube is fascinating because unlike voice podcasts, YouTube has virality to it. So when we
0:49:47 do an in-person recording, the YouTube breach is larger in some instances, not all, than our
0:49:54 podcast reach. And so we get like 300,000 people sort of listening to a podcast episode but on
0:50:01 YouTube, we’ll get 300 to 500 to a million people. But it’s YouTube’s algorithm picking it up. It’s
0:50:06 like people watch this but what we can’t do is like send people off that platform. So it’s really
0:50:11 good for like stats. I was at the gym the other day and this guy’s like I got 2 million TikTok
0:50:17 followers but I can’t do anything with them. So I can keep them on this app and I’m really famous
0:50:23 in this localized environment but TikTok is 100% in control. I don’t own that relationship. Same
0:50:27 as YouTube. I don’t own the relationship with the viewer. YouTube does the minute it doesn’t
0:50:32 like me and wants to cancel me or doesn’t like my content anymore or wants to promote a different
0:50:37 message. Whatever that algorithm is that’s doing that can just like you’re gone.
0:50:43 I think you’re right. I thought Google was going to roll over and played that there for a while.
0:50:48 Like I moved most of my search traffic to Proplexity really like it. Google’s kind of started
0:50:52 and stopped the whole bunch of stuff but recently they’re making noises like they’re not going to
0:50:57 roll over and play dead to Proplexity. That’s such an interesting company right now and to
0:51:01 watch their moves will be very very interesting. It’s a challenging time for them but it looks
0:51:06 like they’re going to they’re not going to let Proplexity just hoover up a bunch of their users.
0:51:11 Hopefully not. We all want some competition here. I have a couple random questions. I’m curious
0:51:17 what you’ve learned about making decisions that you think other people miss. On my CEO journey
0:51:26 for a long time I kind of look for consensus. I think consensus is really the enemy of scale
0:51:30 and so I used to say whenever we’re making an important decision there should be winners in
0:51:35 the room and losers. We shouldn’t find like that negotiated settlement that everyone’s happy.
0:51:39 Somebody should be unhappy. Three or four people should walk out unhappy and one should walk out
0:51:45 happy and we’re all we’re all going to be good with it. As you get bigger this gravity pulls
0:51:50 you towards consensus and I think consensus is the enemy of greatness. How do you fight that?
0:51:56 I write that on whiteboards. I talk about that inside of HubSpot. I try to make an example of
0:52:00 that every time I’m in a room. I’ve written a bunch of blogger articles about that. We keep
0:52:05 posted about that. At one point in Signup HubSpot we had a terrific TOO I love and he had a lot of
0:52:10 great qualities. One of his qualities I didn’t love was he was a consensus person and we had a
0:52:15 lot of conflation over that and so we talked about it a lot. The management team talked about
0:52:20 that a lot but I sort of had this thing like there’s going to be winners and losers in every
0:52:24 argument and if no one walks out a little bit sore we probably made the wrong decision.
0:52:29 So go deeper on that for a second there. So put me in the room at one of these meetings
0:52:32 where there’s four people on one side. There’s four people on the other side.
0:52:36 How do we come to that decision? Is it the highest paid person in the room?
0:52:40 Is it the person closest to the problem? Who actually makes that call?
0:52:46 Let’s just say it’s my call which is rare and two people in the room are saying black and two
0:52:51 people in the room are saying white. I think that the majority of CEOs are walking out of the room
0:52:55 with the decisions great. Trying to please everybody. Yeah. Try to thread the needle and I
0:53:00 think that’s a problem. It creeps in more and more. The bigger you get the worse the problem gets
0:53:04 and I always tried to walk out of the room. It’s like we’re going to pick black or white.
0:53:09 If you lose this decision you might win the next one. Let’s not get all pissed off about it.
0:53:13 We’ll all lose our eye and I think that’s the right way to scale it.
0:53:17 Is there anything else you’ve learned about decision making that you’re like oh I wish I knew
0:53:23 this sooner? I would say one thing I’ve learned about scaling a company like from the outside
0:53:30 went from company with an idea and two employees to you know it’s worth 30 billion dollars and
0:53:36 8,000 employees and a couple hundred thousand customers. It looks like a smooth graph from
0:53:43 the outside but I’ll tell you what it’s a grind on the inside building up spot. It’s very much
0:53:48 two steps forward one step back two steps forward one step back two steps forward one step back the
0:53:55 whole way and there was no silver bullets along the way there was no one higher that completely
0:54:00 changed the game no partnership that changed the game no customer no investor. It was all
0:54:05 kind of two step forward one step back two step forward one step back and the other thing I would
0:54:11 say about the journey is kind of related to that there was definitely wartime and peacetime when
0:54:17 you’re halfway through a two steps forward it was peacetime when it’s one step back it was wartime
0:54:25 and I love wartime I’m definitely a wartime CEO I hate peacetime I really need to sit on my hands
0:54:29 and just let it go like it’s going great leave it alone I have a wartime doing that and I think
0:54:35 certain CEOs are peacetime and certain CEOs are wartime I’m very very very much a wartime person
0:54:40 like COVID wartime we made so many changes during COVID I hated COVID and I hated being back in
0:54:46 society but inside of PubSpot that was a fun job. What does wartime mean for you is that like we’re
0:54:52 fighting for our very survival does it mean we can just move faster and sort of ignore some of
0:54:58 the bureaucracy what what does it mean? I think peacetime is bottoms up and more consensus a
0:55:03 wartime more top down it’s like hey it’s wartime I don’t have time to build consensus on this this
0:55:11 is why I think we should do we’re going left and I like that about wartime and wartime is like okay
0:55:19 I remember 2010 the economy was shaky back then we were a very young company maybe 2009 and our
0:55:24 retention statistics were horrible everyone was canceling our product wasn’t fit back then
0:55:29 and we lost our remember of the thousand customers we had in the beginning of the year we lost like
0:55:38 700 of them like just terrible churn rate in 2009 and that was existential and it was like let’s just
0:55:44 stop the music and start over everything we’re doing going forward has nothing to do with
0:55:49 signing up new customers is like how do we delight every new customer yeah let’s stop obsessing about
0:55:54 how do we turn a prospect into a customer let’s obsess about how do we turn a customer into a
0:55:58 delighting customer and so that was a crisis that really worked we changed the culture of the company
0:56:03 we changed the center of gravity from prospects to customers never wasted a good crisis that was a
0:56:08 really good crisis. What you’re building this how did you manage and I don’t want to say balance
0:56:12 it’s the wrong word but it’s the word everybody understands how did you how did you manage work
0:56:18 life harmony or balance especially during the high pressure periods with a young family
0:56:24 I didn’t I did it very poorly what would you go back and tell your younger yourself no I’m really
0:56:32 proud of it I think my grandkids will be proud of it and I think it took a big effort on my part
0:56:37 to pull it off and if I said oh man I wish I just put in 40 hours a week back then I wouldn’t be sitting
0:56:41 on this podcast it would be wonderful to pull it off and I know that’s not a popular answer I’ll
0:56:47 probably get literally done Twitter for saying that I think that’s a reality it was it was a full
0:56:52 context for it. I’ve noticed this thing and I think people don’t like talking about it but
0:56:57 when you find exceptional people who’ve done exceptional things like yourself
0:57:04 they’re not always the most well-rounded people in every aspect of their life and yet
0:57:10 we sort of expect them to be right it’s like we we love Warren Buffett but we want him to
0:57:16 also be a better family man right the weird thing is the minute Warren Buffett starts doing that
0:57:21 he’s no longer somebody we’re talking about as Warren Buffett and it’s so it goes back to those
0:57:27 sort of like strengths and weaknesses and my hypothesis is that people at the tail end of the
0:57:34 curve have incredible strengths and incredible weaknesses and by trying to address those weaknesses
0:57:40 whether it’s school society nudging people we actually limit we put a ceiling on the strengths
0:57:44 that those people can actually deliver to the benefit of the world. You’ll probably
0:57:48 pillar it on Twitter for saying that but I agree with you on that. I’ll give you an example I’ve
0:57:55 never been married I want to get married so I’m like sexually on my to-do list this year I don’t
0:58:01 know it’s gonna be this year but I never did it and every time I had a relationship like I play
0:58:09 game first and do I regret it I don’t know I’ve had a really good life I’ve really enjoyed the
0:58:15 HubSpot run I’m super proud of it I think when I’m 85 and looking back on my life I’ll still be
0:58:20 super proud of it I think my grandkids will be proud of it so yeah I made some sacrifices
0:58:26 I’m okay with it we always end the podcast with the same question I think you’ll have a really
0:58:33 good answer to this what is success for you I think it’s a really cheesy James Taylor song
0:58:40 named the secret of life is enjoying the passage of time I think she’s very right about that
0:58:47 and think about that post my accident I very much try to not do anything that I don’t want to do
0:58:53 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
0:58:58 past too much and stay out of the future too much I think the secret of life is about how do
0:59:03 you set your life up so you’re really enjoying that passage that’s a beautiful answer thank you so
0:59:14 much for coming on the show Brian thank you sir thanks for listening and learning with us
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