The Philosopher CEO | Clay Co-Founder Kareem Amin

Intro

Kareem Amin: I was like, I’m doing what I think is interesting, and I hope that is aligned with what makes Clay successful. I’m interested in that, but actually I want to make these people successful. And they felt that genuineness. And we did really crazy—you know, Varun, I think he was talking to someone on WhatsApp, and the person was having trouble fixing something on Clay. And he was like, “I’m coming over to your house right now.” And the guy was like, “Don’t come.” He was like, “No, I’m coming.” And they became really good friends. And we were just kind of on that journey with them, truly.

Brian Halligan: Hey everybody, we have Kareem, the founder CEO of Clay on today. Clay is ripping. He’s doing a nice job there. He is a very interesting cat. You’re about to find out. He’s kind of a philosopher, monk-like CEO, and he’s coloring way outside the lines. I think you’re gonna like it.

Main conversation

Brian Halligan: I did a bunch of work to prep, but the best prep was I got a little chance to engage with Varun, your head of go-to-market, and he said—he talked about your padel game that you guys play a lot of padel, and he says he absolutely crushes you.

Kareem Amin: He loses quite a bit.

Brian Halligan: [laughs] And he said you’re relentless and positive and no one tries harder. Where does that come from?

Kareem Amin: I just want to correct the record before we move on.

Brian Halligan: [laughs] I’m gonna call BS on his behalf.

Kareem Amin: Yeah, I have a video of him lying on the floor literally with his ankle almost broken, because he thought the ball was going one way and it went the other, and it just messed with his mind.

Brian Halligan: He said you guys wager and the wagers increase and that you’re like, “Let’s go again! Let’s go again!”

Kareem Amin: Well, I think—yeah, I think maybe what he’s talking about is that I—you know, especially in sports or things like that, when someone beats me in something, I automatically get charged up rather than charged down. Sometimes I’m playing actually with Varun against someone else and if we lose, he wants to change teams, which really baffles me.

Brian Halligan: Okay.

Kareem Amin: That actually really gets to me, because when I lose, I’m like—you know, especially in a game where you’re losing by just one or two points and you can almost see it going your way, I can see that difference and how close we were and how we can kind of get there next time. Whereas he wants—he thinks it’s less fun and we should switch teams.

Brian Halligan: Where does that come from? Little Kareem, where did you get so competitive? Where does the drive come from?

Kareem Amin: Well, that’s a deep cut.

Brian Halligan: Yeah, let’s go.

Kareem Amin: You really went there.

Brian Halligan: Yeah. I’m kind of studying CEOs, and I kind of want to see, like, what are the patterns?

Kareem Amin: Yeah.

Brian Halligan: A lot of CEOs are immigrants. Is it sort of an immigrant edge?

Kareem Amin: I’ll tell you kind of like where I’ve gotten to after thinking about that or analyzing it. It sounds a bit banal, but I think I had an unusual childhood, let’s just say. Just, like, parents divorced, both really great parents, just big divorce. And, you know, traveling across different countries.

Brian Halligan: Loud.

Kareem Amin: Very loud. Lots of things happening. And, like, my introspection is that the ambition comes from, you know, like a really simple thing, right? Like, if you can do something really big, then you’ll be loved, right? And a big part actually of while building the company that I feel like I’ve come to understand, but also resolve and calm down, is that—one thing that I’ve actually told people at work is that a lot of people think you should build from a place of lack. Or, you know, you have a chip on your shoulder, you need to prove something, and you can definitely build great things that way. But I think you create a lot of damage along the way. And to me, I’ve decided to create from a place of wholeness. So I’m like, I don’t need anything. I’m not trying to prove anything. I’m already loved by myself and others, and I don’t need to prove anything. So to me, it’s actually more of a game. And that’s why I often kind of talk about having fun or just how to enjoy the process. Because it’s actually your life. And otherwise you’re in this  just nightmare scenario in your head trying to prove something and doing so many things in the world.

Brian Halligan: How did you get over that?

Kareem Amin: There were many insights along the way.

Brian Halligan: You sound like people I know who go to Hoffman.

Kareem Amin: Yeah.

Brian Halligan: Did you go to Hoffman?

Kareem Amin: No.

Brian Halligan: Okay, you sound like a Hoffman alum.

Kareem Amin: Yeah. Well, I think it’s just if you investigate that over and over again, and you see—okay, you know, I remember raising funding the first time, like, the first large round of funding that we raised. And I started to imagine kind of what that would look like in the future. Well, let’s say now the company is really successful, right? Or I have, you know, hundreds of millions of dollars. How does it feel? And I think it felt empty. So I kind of realized that there’s nothing at the end of success. There’s nothing on that other side that I’m chasing, and that it actually is just right now. Like, how do I feel right now? Why am I doing it? You know, every step of the way, if I wasn’t enjoying it at the end—you get to the end and you didn’t enjoy it, right? And so just playing that forward, I realized okay, what if I decide to enjoy myself right now?

And also, I took the risk of saying that may end up leading to the ambition disappearing or, you know, not doing whatever I want it to. But I was willing to take that risk, because it felt more honest to me. I think my top commitment is to reality, which I think is a helpful commitment if you’re an entrepreneur. You need to see what life is actually like and what is actually happening. And I committed to that and I was like, I’ll go wherever that path goes.

Just a small note actually on the reality thing, because I often talk to people and they’re like, “Hey, I’m not getting any feedback.” And I’m like, “Life is feedback. You’re constantly getting an unbelievable amount of feedback. I can just help you tweak it, understand it, but if I’m the one who’s giving you feedback all the time, it’s not gonna work. You know, this is the feedback.”

Brian Halligan: I feel like humans either live in the past, live in the present and live in the future. Founders tend to live in the future and they’re anxious about it.

Kareem Amin: Right.

Brian Halligan: I think most founders are probably anxious, anxious folks.

Kareem Amin: Very anxious right now.

Brian Halligan: You’re not.

Kareem Amin: I’m not, no. At least not in this particular way. My anxiousness is more existential.

Brian Halligan: Tell me about that.

Kareem Amin: But I’ll give you an insight that I had about living in the future. I was on this silent retreat and, like, you know, crazy things happened and I had these big realizations. And then on day seven out of ten, I was like, “Oh, I can’t wait to go back home and tell everybody about all these things that I realized.” And I was just imagining it and just completely letting go of the place that I was at. And then I realized every time you’re picturing the future or living in the future, you’re just accelerating your own time that you’ve got here and you’re accelerating towards death. So to me, that kind of feels like the Freudian death wish where you’re just imagining something that is not here, that is going to happen in the future, and you’re always there. And then I instantly kind of had this felt experience of …

Brian Halligan: It’s a very Buddhist thought, living in the present.

Kareem Amin: It is a very Buddhist thought.

Brian Halligan: Be calm with yourself.

Kareem Amin: But I actually …

Brian Halligan: I bet no CEOs are like that except for you.

Kareem Amin: I actually think so. The funny thing …

Brian Halligan: Jack Dorsey, probably.

Kareem Amin: Yeah, there’s a lot of CEOs that have the—or come to these thoughts at different moments. I think it just depends when do they come to it, by the way. Sometimes people come to it after they sell their company. Or, you know, you have a lot of star athletes or Olympic athletes who are like, after they’re done, they come back and recognize this. But I do think a lot of people actually have some forms of these thoughts. It doesn’t mean you’re—it means you have clarity of mind for the ambition, for the future thinking. But what I experienced then was a felt experience of what it’s like to actually be there, and then being really grateful for the boredom, where I’m like, oh wow, I’m so grateful to be bored because I’m here. And then I try to carry that with me. I think it actually leads you to make better decisions that are less rushed, less confused about, like, the nature of what’s happening.

Brian Halligan: And do you dip back into this? Do you meditate? You have a practice every day?

Kareem Amin: No. So that’s the interesting thing. I used to have a practice every day when things were more challenging.

Brian Halligan: We’ll get into that.

Kareem Amin: Yeah. I find that I come in and out of it. But, you know, again, some of the thoughts that I’ve come to are, like—the end goal of that is to really merge it into your day-to-day life. And so the practice is remembering it when you should be anxious or when something is going wrong. So I’m like, okay, I’m practicing it right now. And the goal, what I really like about some of these traditions is that they’re like, here are all these tools, and then at the end they’re like, drop the tools. There is no path, you know? I can’t teach you one way or another. You just have to see what it’s like by living.

Brian Halligan: I’ve met with you a few times, but I was on the Sequoia team. I’ll tell you my reaction.

Kareem Amin: Yeah, please.

Brian Halligan: I was negative on it.

Kareem Amin: Yeah.

Brian Halligan: And I was like, Kareem’s not motivated, he’s too laid back, he doesn’t have a chip on his shoulder. And Alfred Lin at Sequoia gives me crap for this still. I obviously had it wrong. Do you think a lot of people read you wrong that way? You had a narrative that just, like, flies in the face of the narrative I had about what a successful tech founder looks like.

Kareem Amin: I think I’m doing it on purpose. I mean, I’ll just say it. But it’s not to, like, rub people the wrong way or to push it in their face, but one, it’s probably just my nature is a little bit contrarian. Like, I find when everybody’s doing one thing, it stops being appealing. I’m like an indie person probably versus a pop person. And I was worried about that for a while. I’m just like, am I just trying to—is that just a way of generating being noticed? But when I’ve been in situations where I felt kind of like aligned with what people were saying, I’ve actually been okay with it. So I’ve proven to myself that it’s not just a bit.

Brian Halligan: There’s a little bit of a bit, though.

Kareem Amin: For sure. Like, nothing is one thing or another. There’s a little bit of a bit. I try to catch myself when I’m enjoying it too much and rein it back in.

Brian Halligan: I see.

Kareem Amin: But there’s a little bit of a part that has fun with it. I think that the dominant narrative around how to build things, one, doesn’t really appeal to me. I don’t think it’s the only way. I also think it creates a lot of damage that isn’t being seen around. And it’s just like, is this actually better for the world?

Brian Halligan: What do you mean by that, the damage? You brought that up twice.

Kareem Amin: Like, basically, take something like, hey, the only way to build is nine-nine-six, blah, blah, blah, right? And it’s like, what does that do to people who only see that, and new people who have no idea what works and what doesn’t and are just copying whatever other people are saying? And by the way, you need to work extremely hard. And in fact, I’ve been working extremely hard for extremely long. And I just value consistency, for example. And what I found is more useful. And I found that you need to tell a story that is actually honest to where you’re at and what you need to do. And sometimes you do need to work nine-nine-six. But to me that was like, well, maybe you don’t have a moat or maybe you need to do something so extraordinary that it requires that sacrifice from you and everybody around you.

But a lot of the times it’s just performative. And what does it do to the people that are in this situation, right? And what they force their employees to do. And then what they, you know, pass on to the next generation of founders and how they build. We were just looking at this case study—and these are kind of like raw, unfiltered thoughts. But when you look at a business, let’s say you look at Apple …

Brian Halligan: I actually think it’s interesting. You’re here in Boston because you’re at Harvard Business School for McKinsey two-day deep dive for scaling companies. I think it’s interesting you took two days out of your schedule to do that.

Kareem Amin: Yeah, I thought that was interesting, too.

Brian Halligan: Yeah. Why? It’s like you don’t have a lot of shit going on? Varun’s doing everything?

Kareem Amin: He’s amazing. Yeah, let’s make him CEO. So I did one at Stanford a couple of years ago with Varun, and initially we were super skeptical, but it was super generative actually for us, mainly just taking the time together. And occasionally, one, I roll the dice, but two, I find that when I’m in a space alone and being fed information, then I get a lot of ideas. So it’s mainly for me. And especially like I’m in a little room alone, you know, there’s no distractions. And I think it’s an important time right now to think clearly, especially about, you know, what is your value prop? Like, what are you really doing?

It’s kind of funny to me that a lot of times what you think you’re doing is not actually what you’re doing or what customers value.

Brian Halligan: What do you mean by that?

Kareem Amin: Like, for example, take Duolingo, right? Is it really teaching you how to learn a language? I don’t know many people that have fully learned the language from Duolingo. Or is it kind of like an edutainment game? Or is it maybe a motivational thing that helps you kind of remember that you want to learn this? Here’s a little bit. Or maybe it, like, helps you stop being anxious. I’ve seen a lot of people just needing to do it to calm themselves down. But if your company thinks that they’re really teaching a language, then you would make certain choices that are different than if you think it is a tool to kind of get you excited about learning some new material at a basic level.

Anyway, I think you should be really clear about what your company actually is doing versus what you want it to do or think that it should do versus what your customers actually are getting value from. And those things need to align.

Brian Halligan: I’m gonna come back to some of this, your philosophies, and you’re kind of like a CEO monk to me. But just to give the audience some context, like, you’ve had a—it’s an unusual journey. People call it a seven-year overnight success. You kind of wandered through the desert for a long, long time, and then you found product-market fit and it really ripped. There’s a lot of founders who are going through that desert. Let’s call it you did it for five years.

Kareem Amin: Yeah.

Brian Halligan: What was that like? Why didn’t you give up?

Kareem Amin: Well, you heard earlier I’m incapable of giving up.

Brian Halligan: I did, but you sold businesses before.

Kareem Amin: Yeah, well, I thought—I mean, that’s right, but that was just like my first attempt, and I think I learned, one, that was a mistake. I wouldn’t want to do that.

Brian Halligan: Okay.

Kareem Amin: And number two, I think you need to keep going at something to really, you know—well, you shouldn’t keep repeating the same things. Usually the door is right next to you. But I have this issue, actually, even with people at the company where, you know, you’re doing something for a year or two, suddenly it gets boring, for example, or you think you’ve mastered it or you’re like, I should go to this other company and lead this thing. But you’re just at the cusp of actually getting to the point where it gets interesting.

Brian Halligan: Or you’re not.

Kareem Amin: Or you’re not. But the difference between those two things is very hard to tell.

Brian Halligan: Yeah.

Kareem Amin: And you need to often push through. The hard part is the part where you think you’re getting bored, or you think—you know, because you give yourself a lot of—I actually called it, like—this feeds into your monk idea, but like the devil is a shapeshifter, you know? So it’s kind of like the thing that’s whispering in your ear like, “Hey, it’s actually you’re bored, or this thing isn’t aligned with your interests, or you should do this or that,” those are all different ways of procrastinating and not facing the hard thing. So one, you need to give it enough time to tell yourself for sure.

Brian Halligan: Five years is a long time.

Kareem Amin: Oh yeah. The five years is not that. I think the five years was a combination really of—it was a spiritual journey. I like that you call it, you know, the Strange Long Trip or the Long Strange Trip.

Brian Halligan: And you’ve had a very long, strange trip.

Kareem Amin: Yes.

Brian Halligan: Yeah.

Kareem Amin: It is a very long, strange trip. But for me, it was actually mostly around deciding and committing to what we’re building. Like, we had a lot of really good ideas. We did a little bit of each, and a lot of them have actually become companies. And I’m friends with the people whose companies they’ve become. And all of our analysis of them was correct. We’re like, this is what’s gonna happen. It’ll stop at this point because of this. But then you get into a place where you’re like, okay, what’s—especially with venture capital, you’re like, what’s the biggest thing that I can do? What is the most impactful thing that I can do?

And I think if your ambition is really big, this is one of the pitfalls that you can fall into. Where my co-founder and I were like, no, we’re trying to do the biggest thing that we can do. And so we would keep changing it to be like, well, if we pointed here, it would be even bigger. Meanwhile, stuff is happening in the market, so technology is changing. So we keep being like, oh, now we could do this even bigger thing. And at some point I was like, it doesn’t actually matter. I’m not trying to do the biggest thing. I’m just going to do what is available right now in front of me and commit, regardless of where that goes.

And so, you know, yes, it’s five years, but really there was two years of us building, two years of us kind of being confused, and then we kind of decided and rebuilt a few things and committed. And then we started seeing kind of the results immediately. It just took some time for everybody else to hear about it. But once we committed, it almost worked instantaneously.

Brian Halligan: I kind of think of everything as, like, you’re going along, you’re making a mess, it’s a dip, and then you come out the other side.

Kareem Amin: Right.

Brian Halligan: But sometimes it’s not a dip.

Kareem Amin: Yeah.

Brian Halligan: Sometimes it just keeps going.

Kareem Amin: Right.

Brian Halligan: Did you have doubts that it might keep going? And did people around you say, like, “What are you doing? You’re really talented, you could be doing any number of things.”

Kareem Amin: Yeah, tremendous doubts, for sure. I think people were—yes, people would say that but, you know, I would say that people typically—especially like me and my co-founder Nicolae, they thought we were some of their smarter friends, right? And felt like we should be able to do whatever we want. And so when we were in that loop, it was also painful because we’re like, hey, we know that we should be able to do this. Everybody else is telling us that. And in fact, we have a lot of signals, like we raised money, when we talk to customers, they’re really impressed. So what is the actual problem? Like, why isn’t it working? And that took a lot of introspection. But I also think that, like, at some point I feel like we identified what the issue is around commitment and deciding to do something.

And I’ve said it in other places. Like, I think I realized, okay, there is a lot of stuff that people don’t talk about in building a company. They just say it’s hard. But what is actually hard? Like, in this case, what was hard was having the courage for people that are perceived to be a certain way or smart or whatever to be like, hey, we’re just gonna pick this thing. I don’t care how silly it sounds. I don’t care about the shame if it fails publicly. I don’t care actually what you think about it.

In fact, when I decided to commit, I stopped listening to everybody. I was like, I’m not listening to you. I’m not listening to my customers, by the way, who are wrong about what they want or how—if you listen to the wrong people at the time when it’s like a small idea, you kill it.

Brian Halligan: We didn’t listen to the customer for, like, the first seven years. I was a customer. We just blocked out what they wanted. We built what I wanted. And then we flipped it and it became a CRM company, and we’re very customer-centric now. I think founders talk about “Just focus on the customer.” I don’t think that’s right a lot of times in the early days of a startup.

Kareem Amin: Well, I think it’s like …

Brian Halligan: Because everyone can do that.

Kareem Amin: Yeah. Well, let me tell you what I think about this, because it’s like in computer science, hill climbing, right? You need to pick the right hill, and then listening to customers is kind of fine-tuning it.

Brian Halligan: Yeah.

Kareem Amin: But also, I think the reason people talk about listening to customers so much, my sense is as the company grows, you start to have your own kind of like dynamics, and it’s a reminder that, hey, it’s not about what—you know, I tell people it’s not about what Kareem wants, because I don’t want you to listen to me. I want you to do the right thing, right? And what I’m telling you is a proxy to what I think is the right thing. But if I tell you to build a feature and it’s the wrong feature and you think it’s the wrong feature and you know what the right feature is, then what I want is Clay to succeed. I don’t want you to do what Kareem—so, you know, people had to be reminded you can’t use “Kareem told me X” as an argument to do something. There’s only very few times where I will tell you a hundred percent, this is what I need you to do.

Brian Halligan: Okay. I went to a presentation that Elon gave once, and he did this thing where he drew all these vectors up, and they were all different sizes, and they were pointing in different directions. He’s like, the magic behind my companies is I just get the darn vectors aligned. Have the strongest ones I can, and when they’re perfectly aligned, things hum. How in your world do you get the darn vectors to align? Or you don’t care that much about it?

Kareem Amin: No, I think that that is the generally right sentiment. But I think there’s many, many different ways to build a company, right? And it depends on what it is that you’re building and the conviction that you have in that. So sometimes in a lot of these companies, there’s a master plan and it’s like, here’s where we’re getting to, here’s step one, fill in the blanks, right? And this is where we’re aligned here. I think a lot of times you discover things as you’re building. So for me, I think there’s two different time periods. There’s a period where we don’t know exactly what’s going on, and people closest to the problem might have more of a sense. And then when you hear it from them, for me, I would say one of my superpowers is when you tell me something that I think is capital T Truth, I hear it and it sticks, you know?

Brian Halligan: It’s loud.

Kareem Amin: Yeah, it’s loud. And then when I repeat it to other people, they remember it. We’re there. So once that happens, then we align everything towards that and we’re super clear. So there’s periods of, like, total alignment. Everybody’s pushing in the same direction. This is the singular goal. And there’s other periods where you need some slack, you need some ability for people to make choices, and you need to know which one you’re in.

Brian Halligan: Okay, I’m gonna just stick on this for a second. Varun talked about how you operate very well in gray situations—ambiguity, uncertainty—and you value that in employees. What I found is when things were very gray inside of HubSpot, things slowed down.

Kareem Amin: Right.

Brian Halligan: And people would say, “You need to clear the fog.” They’d literally say that to me, and I’d be like, “Okay, we have to—there’s four decisions that need to be made—” or typically, there’s one big decision we need to make. It’s like, “Brian, you need to make a damn decision so we can break all these ties and move.” So I was a little bit more—I was like, I let it get gray, but man, the black and white really helped us move.

Kareem Amin: I actually agree with you. I really value nuance is what I think he’s trying to say. And so, you know, sometimes there’s a decision and you know the decision, but you’re not making it. And you need the courage to make it, or you don’t have enough information, or sometimes not making a decision is the correct decision. But it’s more about the clarity of you, if you know what that is and you’re just avoiding it, or maybe it’s a really hard call and you don’t want to make …

Brian Halligan: Maybe it’s tough trade-offs.

Kareem Amin: Yes, tough trade-offs. You don’t want to do it, right? So I think if you know that, then you need clarity and you need to make it happen. This is kind of like what I tell people around this is we all create, we all love startups. They’re doing new things. And then as it becomes a big company, now we hate the big company. But the way it becomes a big company is through this, you know, somewhat of the path of clarity. The generative phase is messy. So I’d say that, like, I am capable of holding that mess.

Brian Halligan: Two contradictory ideas in your head.

Kareem Amin: Yes. And continue to hold them.

Brian Halligan: Most people are not. I would ask people to do it, and they do it for a little while and be like, “I don’t want to do that anymore.” [laughs]

Kareem Amin: Because it’s extremely painful.

Brian Halligan: It hurts their head.

Kareem Amin: Yes, it hurts their head. It’s difficult. It requires difficult conversations. So I don’t think everybody can do it, but I do think that the more you trust people with that, some segment of them will value that. And I remember, like, being an employee and I would have valued that.

Brian Halligan: Yeah. Okay, just going back to your five years through the desert and your two years. At some point you said this one—you had a very broad vision, and then you’re like, “This one use case is gonna work.”

Kareem Amin: Yeah.

Brian Halligan: And you picked it: outbound sales, marketing, whatever you want to call it, go-to-market engineer, eventually. Did that kind of hurt you that you had this big, broad platform-y thing and then, like, we’re gonna really narrow.

Kareem Amin: Yeah, for sure. Yeah, that was very, very difficult. And I’d say that—well, I’ll say two things. So one is that, you know, it’s interesting that you perceive me as this or, like, people perceive me as this before. My friends actually in the past perceived me as extremely aggressive, really intense. And people can’t even imagine that right now.

Brian Halligan: I find you intense.

Kareem Amin: Which I still am, but it’s, like, contained and directed and hopefully more, you know, something that I like to open up when necessary. But on the point of picking, so I would say that it was actually my co-founder Nicolae who identified this segment and use case. And I was finding it very challenging to commit to this. And I think he was, too, because I’m like, how is this related to—like, you know, we wanted to give the power of programming to more people.

Brian Halligan: Yeah.

Kareem Amin: And that still lives on in the fact that we called it go-to-market engineering.

Brian Halligan: Yes.

Kareem Amin: And to, like, the idiosyncratic way in which all the features are built to give you that maximum power and flexibility. But we would yo-yo between kind of like maximum power and flexibility and, hey, it should just work out of the box simplicity. And at some point we were like, okay, let’s just commit.

Brian Halligan: Power and flexibility.

Kareem Amin: And to the power and flexibility, which was the exact opposite of what everybody believed would work and what customers said. Like, I’ll give you—everybody has copied this waterfall enrichment concept, right? But you know what? If you talk to customers, they’re like, “Listen, I just want the number of people that work at a company. I don’t care where you’re getting it from. I just want to wave a magic wand and do that.” And my argument has been like, once the technology is there for that, we will do that. But at the moment, the best technology is put everything together, give you transparency and speed up that process. That’s what actually solves the problem. You can say, like, “I want to go from New York to London in one hour,” but I can’t do that for you. So what’s the next best thing?

Brian Halligan: We have a couple of things in common between the companies. Very early we said we’re gonna create this category called “inbound marketing.” It really worked. You’ve done the same thing with go-to-market engineer. It appears to be really working.

Kareem Amin: Yeah.

Brian Halligan: Everybody and their brother asked me how to create a category. And there’s a little bit of magic in it.

Kareem Amin: [laughs] Right.

Brian Halligan: Can you talk about how you did it, the decision on the name, how you propagated it, advice for so many founders who want to do this?

Kareem Amin: You know, the common advice about this is don’t do it, right? And it’s very challenging, which it is. I don’t think you can create necessarily a category. You can take something that is happening and name it.

Brian Halligan: That’s what we did.

Kareem Amin: Right. And then give it—like, put a circle around it and give it some fuzzy boundaries, which is important. And then allow something that’s already happening. It’s kind of like a wave and you’re like, okay, I’m gonna name this wave. I’m gonna give it credibility. But for us, the way we did it was one, we started noticing people use the term “GTM” instead of “sales” in the most forward-looking organizations and the ones that would adopt us. So we decided to use that. And then we were like, well, what are they doing there? We used to have a term called “customer engineer,” where it was just kind of like forward-deployed engineer. And we’re like, well, what if you—actually the best categories, I think, are like two words stuck together, right? Because I think language is evolving. Like, imagine if you had a Roomba, what would you call it before you invented a vacuum? You know, it would be really hard to name it.

Brian Halligan: Yep. Who came up with the name? And when you came up with it, were you like, “We’re gonna create a category around it,” or did it just sort of start happening?

Kareem Amin: No. So Varun and I were chatting about what we should call our own people who are helping customers.

Brian Halligan: Fine.

Kareem Amin: And then I was like, “Let’s just call them go-to-market engineers.”

Brian Halligan: As opposed to now they might have called it forward deployment engineer.

Kareem Amin: Yeah. Or customer engineer. But we wanted it to be unique to our thing—and actually credit to Mike Vernall, who was one of our early investors. I would meet with him and he’d be like, “We should own a title.” And I was like, “Well, how are we gonna do that?” You know? And so when we were talking about this, we’re like, okay, it’s go-to-market engineer. Let’s call our own team go-to-market engineers, because they’re helping you think about your go-to-market in a systematic way.

So basically, I think it needs to connect to some of the core assumptions about your product. So if you think about Clay, by the way, most of the decisions are obvious. So this is where the clarity is important. I think people get really confused when they hear me say, like, you should live in ambiguity, all that stuff. There are certain things that need to be super clear, and living in the ambiguity allows you to one day get to the clarity.

So for us, some of the decisions that we made that are super important are we are going be for a technical user. We’re gonna call them the go-to-market engineer. We’re gonna be the most powerful and the most flexible. We’re not going to own the data, we’re going to be a data marketplace, and we’re going to charge in usage and not seats.

Brian Halligan: Clear.

Kareem Amin: Right. Now those decisions do not change and have not changed. And actually, if you look at the product, all the decisions are super clear if you go back to that. And we’re like, hey, does it make it more powerful? Does it make it more flexible? Oversimplicity. One of our things is power and flexibility over simplicity, not because we don’t want it to be simple, but when they conflict, we give you power because it’s a technical user. Now we can also sell it to you in a particular way—and it was super important for me for it to be PLG, by the way. That’s another reason why it took so long, because this is a very difficult product to make it usable.

Brian Halligan: Hard to use and PLG typically don’t fit.

Kareem Amin: Right.

Brian Halligan: Or not hard to use, but powerful.

Kareem Amin: Powerful, yeah. And so needed to be a type of customer who can pick it up and hack around with it.

Brian Halligan: Yeah.

Kareem Amin: And then the usage-based meant—I really like this thing that I think I was reading something a long time ago around, like, Hegel’s idea of thesis and antithesis and then leads to synthesis. So it’s like a theory of history. And then there was this guy Feuerbach who was another philosopher who was also talking. He kind of flipped around his whole thesis and was like, you know, Hegel’s thing is like we’re going towards God or Geist or whatever. And Feuerbach was like, actually, we’re already the complete thing, and we are projecting—like, the idea of God is like our own projection of our own misgivings and things like that.

Brian Halligan: Wait, what’s this got to do with go-to-market engineering?

Kareem Amin: So let me bring it back for you. But welcome to my mind.

Brian Halligan: Okay, I like it.

Kareem Amin: So to me, the interesting thing—this is more of a fact that I think is interesting. But the interesting thing is, like, taking something and then flipping it on its head is a great technique for innovation. And then taking that thing to its natural conclusion. So you can—you know, in philosophy you would, like, study these two theorists and look at their ideas. But it’s the same thing here. It’s like, hey, what if we took—everybody told me that you should sell to salespeople if you’re in go-to-market and it needs to be super simple and it’s seat-based. Flip everything around, you have a new product, right? Now is this a better product than the old generation of products? You have to have a thesis around that as well. Which we do. But I think that’s kind of the approach that I took at the time that helped us make all of the other decisions later easy.

Brian Halligan: Fell out of it.

Kareem Amin: Yes.

Brian Halligan: The name, how did it propagate? You called your folks GTM engineers.

Kareem Amin: Yeah. So the go-to-market engineers, I think this is very subtle and very tricky, right? Because if you go out—I think you guys did a different thing where you were like, we are going to, like, go out and talk about this and be loud.

Brian Halligan: We did something very similar. Like, there was SEO and blogging and all this stuff. And we said, that’s inbound marketing.

Kareem Amin: Right.

Brian Halligan: And by the way, what was good about it was there was an enemy. No one liked outbound marketing.

Kareem Amin: Right.

Brian Halligan: And outbound marketing was a word. Inbound wasn’t.

Kareem Amin: Right.

Brian Halligan: But we just flogged it. Like, we wrote a book, we wrote articles, we did a conference.

Kareem Amin: So we took the exact opposite approach.

Brian Halligan: Exactly opposite.

Kareem Amin: And again, which is like, don’t—I mean, some people don’t even know that we came up with this, right? It’s kind of like you need to think of concentric circles, that it’s gonna evolve. So we talked to agencies who are already doing this work, and we started talking about how our own team is called go-to-market engineers. They started adopting it because it was a cool term and showed up on their LinkedIn. And then we basically empowered them with all the information, all the things to make them more successful and look good. And because they needed business. So here’s a big …

Brian Halligan: This is the same as us. Like, we educated and we gave them everything they needed.

Kareem Amin: Yes.

Brian Halligan: To create an inbound marketing agency.

Kareem Amin: Exactly. The only part is that we try to not take credit for it or be involved in the conversation and we leave the conversation open—and this may be part of the ambiguity thing. So we’re not like, “Here’s what a go-to-market engineer is.” We’re letting the market evolve, and it’s actually broadening. As it should. You know, if you’re using Claude, you’re a go-to-market engineer. Good market engineering, and why I think the category is a category, is that it’s a point of view on the world.

Brian Halligan: Yeah.

Kareem Amin: It’s not a technology. And it’s like, how do you run your go-to-market team where you build tools, where you test hypotheses? And then with AI, it makes all of that much, much easier since code is cheap, right? So first the agencies. And again, obviously, you know this because it’s like agencies need the work. So they’re gonna be—if you were targeting companies, no one wants to tell you how they grew. In fact, our new kind of internal tagline for Clay is go-to-market infrastructure: to grow in ways your competitors can’t. That’s the whole point of it. It’s like, how do you do something that no one can copy, right?

Brian Halligan: Turns out people are followers.

Kareem Amin: Right. But the thing is that’s why you need to build a system that you can update quickly because just the path to people copying you is gonna be fast. And you need to understand your business well enough to come up with the next hypothesis, or AI needs to understand your business well enough.

Brian Halligan: Okay. So you came up with a clever name.

Kareem Amin: Right.

Brian Halligan: You called your people that, you started educating the agencies on it. They liked the name, they started using it, and it just sort of slowly spread. Is that kind of how you did it?

Kareem Amin: I would say it quickly spread in certain areas.

Brian Halligan: Yeah.

Kareem Amin: And then we provided some scaffolding around—like we published a couple of articles, but we tried to stay in the background of this.

Brian Halligan: Yeah. We did not. We were competing with content marketing at the time.

Kareem Amin: Yeah.

Brian Halligan: And so we were aggressive with it. We didn’t want to lose that kind of battle.

Kareem Amin: That makes sense. Yeah. I think the main thing is that we came up with a—I don’t know if you guys thought about it as a title or a category. We thought about it as a title, and I knew that one day it would be the category.

Brian Halligan: We didn’t think of it that way. We thought of it as like a new way to market.

Kareem Amin: Right.

Brian Halligan: Yours is more a title. It was different.

Kareem Amin: Yeah. So we thought about it as a title, and we wanted the people to call themselves that. And so we were focused on that. And then the idea was that we earned the right to call it a category. And by the way, I think time really matters in all of these things. It’s the storytelling. So if you go too early and start telling the story, in fact, people push back against you. So you need to pick the moment where there’s so many people who are invested in this. You know, we had our own community round. So there are people who we’ve proven—and by the way, we have organic—the other thing that we did that’s super important, by the way, is we have Clay Clubs in over, like, 80 places in the world.

Brian Halligan: We played these same games, and they worked.

Kareem Amin: Yeah.

Brian Halligan: These things work.

Kareem Amin: And then we just help them. But the key thing around that is, like, now that people have actually made a lot of money from it and that it’s helpful to them, you call it the category. And it’s important that the category is bigger than you. That’s, I think, the last piece that’s super clear and continues to evolve, right?

Brian Halligan: Another thing you have in common with HubSpot is the whole agency thing was the second—we started as direct.

Kareem Amin: Yeah.

Brian Halligan: And I was the first salesman. And we were quite good at it, actually. And then we had this one sales rep named Pete Caputa. And …

Kareem Amin: Great name.

Brian Halligan: Yeah. And we had a lot of agencies interested. And I remember it was like two, three years in, I was like, the product’s not ready for someone else to sell it. It’s not mature enough. It’s like, don’t call on them. But we also had, like, a weekend—you could do anything you wanted on the weekends or after hours. It’s kind of like Google’s 20 percent time.

Kareem Amin: Yeah.

Brian Halligan: And one weekend he started calling on them, and you could just look at the histogram of the numbers, and it’s typically a bell curve. But he was like 4x the next month in revenue. I was like, I guess Pete was right. And then we started building a whole program. It’s like a separate company to engage with these people and take care of them.

Kareem Amin: Yeah.

Brian Halligan: How did that happen to you? And advice for people who want to create an alternate—so many people come to me and want to create a second channel. And it’s very hard.

Kareem Amin: Yeah, it’s very hard. I mean, you know, I don’t know that we’ve fully cracked that, but I think that I would say, like, a big part of this was Varun as well. Like, we were in WhatsApp groups with people who own agencies. I feel like the answer that I think people don’t really want to know is there’s no playbook. We were being honest and genuinely authentic. The mission is how do we help companies grow? And we’re gonna help you grow no matter what. Back again to some of my pieces around, like, how I was operating. I was not operating—and maybe you were reading this correctly, I’m not like, “I am trying to make Clay successful,” I was like, I’m doing what I think is interesting, and I hope that is aligned with what makes Clay successful. I’m interested in that, but actually, I want to make these people successful. And they felt that genuineness, and we did really crazy—you know, Varun, I think he was talking to someone on WhatsApp, and the person was having trouble fixing something on Clay. He was like, “I’m coming over to your house right now.”

Brian Halligan: Yeah.

Kareem Amin: And the guy was like, “Don’t come.” He was like, “No, I’m coming.” And they became really good friends. So we built genuine, authentic friendships with a lot of the people, and some people left their job to start Claygencies.

Brian Halligan: We had the same.

Kareem Amin: Yeah. And we were just kind of on that journey with them, truly.

Brian Halligan: Yeah.

Kareem Amin: I think if in our heads we were thinking hey, we’re trying to create this category and we need them to do X, Y and Z—people are very good people readers, by the way, and they can read your intention. Similar to VCs, right? Their top thing is they can read your intention. So if you’re gonna go there and fake confidence, that’s not gonna work. You need to truly believe that you have the magic sauce.

Brian Halligan: Another thing that everyone’s coming to me asking about is pricing, and you guys announced a pricing change. You caught a bunch of heat for it, and you responded in an interesting way. All CEOs seem to go through, like, getting punched in the face by the market. And you just kind of got punched. I don’t actually care that much about the pricing.

Kareem Amin: Right, right.

Brian Halligan: Talk about the backlash to it, and talk about what you did and kind of your philosophy around it.

Kareem Amin: I would say the backlash was minimal, or at least we perceived it to be minimal.

Brian Halligan: It felt loud to me.

Kareem Amin: Right. I think, like, we did a bunch of analysis around, like, sentiment analysis on some of these things and it was like 70 percent neutral, you know, and some negative people. And so I think all the people that were quite negative or loud about it had some self-interest. So, you know, they owned something where it would benefit them for this to not work. We haven’t seen kind of that negativity show up in the numbers. So that’s another way in which I know. But the way that we dealt with it …

Brian Halligan: I think that’s the interesting part.

Kareem Amin: Yeah. And, you know, I don’t know, there’s like a huge backlash against Ferrari’s new, like, electric thing. And by the way, I was reading there was a huge backlash when they had their SUV—which they don’t call an SUV, it’s an FUV or whatever—but now it’s completely sold out.

Brian Halligan: Okay.

Kareem Amin: So anyway, back to our pricing change. The things that help us withstand something like that is like, one, what is our conviction in our thinking, right? So we’re like, hey, we bundled credits. Credits cost data and whatever value we provide. And we were big enough at this point, and thought that we were well known enough that we can break it up into two axes, and then make it so that it’s clear what you’re paying where, and also make it cheaper.

Brian Halligan: Splitting compute and splitting the data.

Kareem Amin: Right, exactly. And so now that we have compute and data, and we trusted the sophistication of our customers to eventually understand that, and also understand that it’s truly in their benefit. Like, we calculated it and we’re like, this will be cheaper for you on the short term. And on the long term, we should all make more money, right? But the other thing is that we were absolutely transparent in our document. It couldn’t be more transparent. It literally was word for word what we were saying internally in our meetings. And that’s a common thing for us in the way that we operate, and I think maybe unusual and surprising to people.

Brian Halligan: Yeah, it disarms them.

Kareem Amin: Yeah. And it goes back to this …

Brian Halligan: Transparency equals trust. It’s not even correlated with it, it equals it.

Kareem Amin: It equals trust.

Brian Halligan: Yeah.

Kareem Amin: And in order to do that, you need the right channel and you need to be talking to the right people. Otherwise, the transparency could actually be damaging to you. But I think that’s like where the nuance—believing in nuance, and that even though everybody wants you to speak in bite-sized pieces, we’re like, hey, we’re gonna actually show all of our work even though it’s long. And then other people will actually read it and digest it.

Brian Halligan: Yeah, I thought that was very well handled. I want to kind of shift to kind of you as CEO. What’s your day like?

Kareem Amin: I have, like, two terms for it. One is I’m a momentum detective, right? So I just go around the company and …

Brian Halligan: I love this.

Kareem Amin: Yeah, I find momentum is so hard to get if you lose it. And so anytime you see an area of the company losing momentum, that’s where your focus should be, because sometimes you just need to grease it and then it keeps going.

Brian Halligan: Oh, so you don’t hop on where the momentum’s hot, you hop on when it’s starting to wane.

Kareem Amin: Yes. Well, it’s both, right? You want to know the places where it’s hot, but often those places don’t need you. What is the unique thing that you can do as a CEO, right?

I’ll give you a couple of examples of things that, for example, I’ve done that created momentum and then places where I’ve, like, kept the momentum going. But, you know, the go-to-market engineering, right, like, getting that right. And then, you know, we had Mishti and Varun write that article, but getting that and putting this is what we’re doing, push through with it. And then we came up with this concept of go-to-market alpha. I was talking to a friend of mine and we were like, “Hey, this is the term.” And then I went back and I was talking to a couple of people. It resonated with them and we’re like, this is it. Now we use this in all of our language. And, you know, people initially were like, “Alpha? That sounds like really nerdy.”

Brian Halligan: Your customers are nerdy.

Kareem Amin: Right. Or just like it’s too finite. And I’m like, people will get it from finance. You don’t even need to know. As soon as I say it, people say, “Oh yeah, you need to have some competitive advantage, but it’s a better word for it.”

So we have a couple of these things where every once in a while there’s one idea that generates momentum. I’ll give you another idea. We needed a feature that we call “audiences,” which, you know, allows you to have, like, a concept of a company or a person in the product so that you can aggregate signals on it. And it’s backed by a CRM. So we’re not building a CRM, it’s backed by that. But to get that going in the company was incredibly challenging. You know, people are like, “What about our tables?” Well, like, we don’t want this to have table limits, no row limits, no cell size limit. A lot of the limits, we just removed it.

So I had to motivate it in a different way. It wasn’t getting traction, which is kind of interesting, but I had to motivate it by saying, okay, we need signals, which is we already have data. We need data changing over time. And so let’s build signals. That was okay. People got that. And we then were selling signals, and we started beating companies that only sold, like, job changer signals. Then the team themselves realized well, what if you have five signals? What are you gonna aggregate it up? Well, you need this concept of an audience, which we were talking about before. And I think it’s kind of, again, the storytelling. I should have been telling that story before but, like, leading the team so that they believe themselves and they have the momentum is very different than me being like, “You need to build this feature.” So one of the things I think you realize as CEO is that you are sometimes way ahead of everybody else.

Brian Halligan: Yeah.

Kareem Amin: Because you’re getting input from so many places, not just because you’re smarter or whatever it is, but you’re just getting—your purview is larger, and that’s all you’re thinking about all day. And you have an intuition for this that you’ve built over time, because I’ve made a huge number of mistakes everywhere, but I’ve also been doing this for so long.

Brian Halligan: Yeah, Momentum Detective. I love that.

Kareem Amin: Right.

Brian Halligan: You’re good at branding, by the way.

Kareem Amin: Apparently.

Brian Halligan: All your claygencies, all that stuff. You’re very clever at it. You’ve got kind of two modes.

Kareem Amin: Yeah, I think there’s that one, and then there’s really—it really is mainly around, like, people are in some kind of, you know, funk and I remove that.

Brian Halligan: Advice on how to do that for other CEOs?

Kareem Amin: So actually my head of people told me that I’m the only CEO that she’s worked with that has apologized. And I would say that that’s one very helpful technique. Like, someone was telling me, for example, they had, like, a bunch of problems, right? And it was like, there are many problems that seem like they’re the problem, but often if you listen, and apologizing doesn’t mean necessarily that, you know, that the whole organization is wrong. It might be that we didn’t listen to you, or we didn’t treat you in the way that made you feel respected. And once that calms down, we can then deal with the actual problem. And people are very sensitive to that.

Brian Halligan: Just very tactically, like your day, do you leave a lot of open time to momentum surf? Are you packed every half hour?

Kareem Amin: It goes in phases. So most of my days for a very long time were packed, like, every 30 minutes, every 20 minutes, and it’s complete context switching. So, you know, it’s recruiting, product decision making, listening to someone, removing a problem, comp issues, you know, talking to partners. So it was …

Brian Halligan: All the things.

Kareem Amin: All the things. And then once I do that for some period of time, you know, typically if that happens too many weeks in a row, I need to stop, delete everything, and leave a ton of space. Like, we run the company in just-in-time decision-making. So, like, some unusual things that we do, which we will eventually introduce, but not yet, is we don’t have an exec team meeting, which I think people find bizarre. How do you stay aligned? All that stuff. We call—we have open space. Call me whenever and then we resolve it. Otherwise people wait for the meeting, as you know. But yeah, I think that the open space is my preference. And the other way where everything is packed works, but it typically means things aren’t, like—people don’t have the information for them to make distributed decision-making, and I need to control everything in order to make things work. But it’s exhausting and you can only do for—sometimes it’s necessary, but you can only do it for, you know, months at a time.

Brian Halligan: And where do you get your think time in? Or, like, I want to go really deep on and build an agent for myself. Like, where do you—how do you fit that in? Is that weekends or …

Kareem Amin: That has to be after work, weekends, et cetera. But I also—like, I would say I’m unusual in that my thinking—like, for example, I go out dancing with my friends, and I’m thinking and I’m also talking to them about it. And so I’m—I tend to like movement actually and doing things. Or you’re on a hike. Those are helpful. But again, like, sometimes I actually think—again, this is maybe counterintuitive but, like, you don’t want to look at something directly to see it. You might want to squint at it because it’s too much. So I get information through other people, and then process that and then come up with a decision rather than—you can’t just rely on, like, your firsthand experience of, like, you know, I built a lot of the initial product with my co-founder, so I remember everything about it. But I try to make decisions now without needing to—you know, like, if someone tells me there’s an issue with a feature, I can simulate it in my head and use it. I don’t need to, like, play around with it. And with kind of like, let’s say playing around with LLMs, there’s so many people experimenting and trying to soak that in. The first-hand knowledge is limited.

Brian Halligan: Do you have one-on-ones or you’re like—yeah, what do you think about that? How many direct reports do you do one-on-ones?

Kareem Amin: So the …

Brian Halligan: These are just tactical things.

Kareem Amin: Yeah, yeah. The tactical things.

Brian Halligan: People ask me all the time.

Kareem Amin: So right now I probably have seven direct reports. I’ve been limiting. I’m actually just—so I’ve gone back and forth, and I’m trying to put everybody in the same meeting and have, like, one-on-ones once a month. But again …

Brian Halligan: We did exactly that for our first five years.

Kareem Amin: Yeah, go back to just-in-time processing. Just if you need something, come to me is the easiest way. But I did manage the whole engineering team up to 70 people.

Brian Halligan: I see.

Kareem Amin: Without a head of Eng until last September.

Brian Halligan: Okay, that was a lot.

Kareem Amin: Yeah, so I tend to—and just through the managers, but I had, like, pretty much a direct relationship with almost all the engineers because I wanted to keep that.

Brian Halligan: Stay close to it.

Kareem Amin: Yeah.

Brian Halligan: I didn’t do one-on-ones for the longest time, and then I did one-on-ones every week. I really wish I didn’t.

Kareem Amin: Yeah.

Brian Halligan: It’s a little—they can be draining.

Kareem Amin: Very draining.

Brian Halligan: Where are you on that?

Kareem Amin: I think that it’s draining. I’ve removed one-on-ones. I have one-on-ones with—so now actually, my new one-on-ones are with people that are not reporting to me, where I’m like, these are top priorities for the company. So I have a one-on-one with our head of sales because I’m like, we need to stay aligned, right? If there’s a thing where we’re doing some new project, I’d rather have one-on-ones with that person. So I’m trying to do it actually in places where I feel—like, the reason I have it with our head of sales is our sales team is growing so tremendously, and I’m the person who’s communicating the culture, and I want to make sure we stay aligned. And then any issues can be brought up and dealt with quickly. But I don’t need that with my head of engineering.

Brian Halligan: So you don’t have standing weekly one-on-ones?

Kareem Amin: I’m deleting all of those.

Brian Halligan: Yeah. Got it. Let’s just talk about trust. People used to complain to me that I trusted the handful of people and really over-indexed on their input. And it sounds like you’re a person who gets a lot of input from a lot of places and then maybe didn’t trust—my trust circle was small and people complained about that.

Kareem Amin: Interesting, yeah.

Brian Halligan: Similar?

Kareem Amin: Yeah. And did you change that as people talked to you about it?

Brian Halligan: I tried to. It didn’t …

Kareem Amin: Yeah.

Brian Halligan: Honestly, it didn’t really work. Trust is hard to build with me.

Kareem Amin: Yeah. I think that I have a similar thing. I’m not—I have trust issues, for sure.

Brian Halligan: Yeah.

Kareem Amin: But it’s different. I mean, there’s different levels of trust, so there’s like real trust, which I have with a handful of people.

Brian Halligan: That’s what I’m talking about.

Kareem Amin: Yeah. People have said to me is that I’m too forgiving. So I’d say I have—like, one thing that I’m trying to change is being forgiving, forgiving, forgiving and then explode, right? Because I’ve been super annoyed, and feel like I’ve given too much. So I’m trying to, you know, give you tons of, like—I’m actually angry right now, I’m annoyed over time.

Brian Halligan: Do you hold on to people too long?

Kareem Amin: Definitely. But it has worked out sometimes.

Brian Halligan: Okay.

Kareem Amin: I keep hearing, you know, people are like, “It’s never worked out.” I would say that as an organization, we believe in you. We want it to work out, and we’re constantly assuming the best intentions. And sometimes—because, you know, it’s sometimes the person, sometimes the context, right? So you can get the wrong—with the wrong context, you get the worst out of someone. So there have been situations where something seemed completely off and I, like, listened to this person, did the exact opposite of what everybody—you know, like, I’ll give you an example that would seem absurd, right? Someone did something wrong, and it doesn’t matter what the details are, but I gave them an increase in salary.

Brian Halligan: Why?

Kareem Amin: Right? Now that seems crazy. Because I …

Brian Halligan: Seems like something a contrarian CEO would do. [laughs]

Kareem Amin: [laughs] Now that person is one of the best performing people in the company, right? And the reason is I realized there was—it was out of, like …

Brian Halligan: Structural things held them back.

Kareem Amin: And it was partially out of the fact that they were not being paid correctly.

Brian Halligan: Oh, okay. Fine.

Kareem Amin: But you could have been like, wow, this person is really—and you’re just like, you shouldn’t reward something when someone does the wrong thing, but actually sometimes you can fix it.

Brian Halligan: Okay. I’ve heard you—or maybe everyone told me that a company exaggerates a founder’s traits. What traits are you happy it’s exaggerating of yours? And what traits are you like, “I wish it wouldn’t?” [laughs]

Kareem Amin: Right. That’s good. Yeah, I told them that. I feel like it’s a …

Brian Halligan: By the way, I agree.

Kareem Amin: Usually it’s like where I get surprised by people. So I do feel like people seem really open and enjoy working together. And it’s very—at least that’s the feedback that we constantly hear is that people are having fun, and sometimes they …

Brian Halligan: That’s you.

Kareem Amin: Yeah, they’re like, you know, there’s an absurdist kind of like feeling to the company. It feels like—I don’t know, it’s like a postmodern painting, you know, there’s stuff. And then everything has its counterpoint. You just need to be conscious of what it is. And I do think—like, I really value patience, as can be seen by the five-year thing. And I think sometimes we are too patient with things that are not right.

Brian Halligan: It’s not a dip, it’s just gonna keep going.

Kareem Amin: Yeah, it’s not good enough. And I think—like, I have very high standards, and at the same time I’m very forgiving. And so I think that …

Brian Halligan: Where did that come from?

Kareem Amin: The very forgiving part?

Brian Halligan: High standards. Is that mom? Is that dad? Where’s that?

Kareem Amin: Yeah, I think the—I mean, the high standards, I feel like it’s taste. My parents have high standards, and the forgiving part, yeah, it probably is like, my dad is very forgiving. But I think it also is back to kind of like, why are we doing this?

Brian Halligan: Yeah.

Kareem Amin: Which I don’t know that everybody is thinking about until later. The way that I’m interacting with people at work—you know, one of the things I think about is—I’ve talked about this, for example, at the company, right? And it’s like, if you can’t forgive your coworker for some infraction or some random thing they said to you or some, like, small competitive nature thing that you’re doing, how are we going to actually forgive people in the world? How are we going to make this work? This is a microcosm. Everything that is happening in your personal life as a problem is probably happening at work as well. Just at work, we can give you feedback and, you know, the stakes might be lower in some ways, right?

And that’s why we try to cover therapy, we try to cover coaching. We give coaching to people who are not leaders, because often it’s ICs who are going through kind of—you know, sometimes people are going through crazy cycles of emotional things because I made some random comment passing by, or someone said something to them and then it really gets in their head. And how much time are we wasting on this versus doing productive work? So on the one hand, you can be like, hey, we’re a company that is trying to, you know, maximize shareholder value and dominate the world and make as much money as possible. You’re probably wasting a shit ton of money by not dealing with people’s emotions around very silly things.

Brian Halligan: Mm-hmm.

Kareem Amin: And also by perpetuating kind of like—I actually think what—this is a pet theory that I have, is that very few people get to this stage of company, right? And when you’re in it, you know, you’re kind of trying to stay exactly on the line of success. So you don’t want to try too many crazy things. You want to focus on your product and what’s unique about you. And so you get this wisdom from other people who have done it, and it’s all kind of like—we call it “couch wisdom,” you know? It’s not really studied. It’s like what this person did before, and therefore they’ll give you some advice, you will do it, and you will get the exact same problems that they had. So sometimes we’re trying different things. You know, people tell me like, hey, you should hire fast, fire fast. Well, that has a specific set of problems.

Brian Halligan: Hire slow, fire fast.

Kareem Amin: Yeah, hire slow, fire fast.

Brian Halligan: You don’t believe in that?

Brian Halligan: You obviously don’t. You just said the …

Kareem Amin: Yeah, yeah, yeah. I also think that there’s a lot of moments where we should make decisions faster around that, but I just don’t believe in these rules of thumb that I think at some point you shut down internally. You stop, like, thinking about the situation. You’re just following the rule.

Brian Halligan: What other CEO-isms do you think are stupid?

Kareem Amin: A lot.

Brian Halligan: Like?

Kareem Amin: I think driving people really hard without paying attention to—like, I’ll give you one example. Like, people come in and they’re like, “AI is gonna create a ton of productivity. We should lay off, fire 20 percent of the team.” Without knowing what you’re actually doing. And that’s what it makes people like ICs think execs are dumb, right? Because they’re going to meetings together, they hear some other person did this, you just go and do it. And I think there’s a huge lack of empathy for the team—and I feel it sometimes, too. It’s like the principal-agent problem, management versus workers, where you’re like, why aren’t people thinking correctly? Why aren’t they, you know, taking action? Why aren’t they owning this? Well, their incentives aren’t aligned for that.

Anyway, I also think that thinking of work—this is a big one for me—like, my definition of fun is very broad, obviously. So, like, type two fun is fun for me. Climbing something is fun. But I think motivating people through either just greed or fear or discipline is not always the optimal. You need the whole toolkit. So, like, you know, another word for discipline could be …

Brian Halligan: The fear and greed thing. Those are the …

Kareem Amin: All levers, by the way. Yes.

Brian Halligan: How do you think about that?

Kareem Amin: I believe in the full spectrum of the thing. So it’s like devotion is as good as discipline. Like, you can’t just use some of these tools without understanding both motivating your team to win, but also create, like, a place that you actually want to be in. So my point is, there’s something about business—this is again some of my own—that feels like you’re just trying to take this thing and hand it to someone else. Like, it’s like a musical chairs thing, right? So the best businesses—I’ve said this at the beginning—like Apple. It’s like well, who’s actually doing all of the stuff? It’s like Foxconn. Like, here’s this beautiful business that has all the numbers are going correct, but it’s because I can squeeze my suppliers in this way. Now I’m not gonna think about that supplier. It’s kind of like throwing your rubbish somewhere else and you’re like, that’s in China or that’s over there. And what I’m thinking about is like, hey, we live in the world together. What happens if I win but you lose? It’s fine. Like, I guess you’ll—you can just jump off, and maybe you’ll not get caught and no one will worry about it. But I don’t want to do that, because I don’t want to live with myself in this way.

Brian Halligan: Okay. I had Jack Dorsey on a few weeks ago. You two rhyme. He’s an original thinker. He’s not central casting for CEOs. And, you know, he’s laid off a big chunk of his employees, but I think he’s really retooled the way the company works. And, you know, he’s put AI in the center, and he’s delegating a lot of decisions to the center. The people are on the outside. He’s rethought his org chart, compensation. He’s sort of reimagining it. I assume you’re following some of that.

Kareem Amin: Yeah.

Brian Halligan: What’s your take?

Kareem Amin: I think that, you know, it’s hard with, like, public companies, too, because it’s like, what is the narrative versus what’s reality? I do think that sometimes you do need to retool the company, and maybe you hire too many people, or maybe things are changing. And we don’t have really good ways in general to say the truth without people—again, I really think it is this principal-agent problem, right? It’s like whatever you say is being parsed to be like, is it what you really said or does it mean something else? Are you covering up something?

Brian Halligan: I don’t think he was covering it up.

Kareem Amin: Yeah. So that’s what I mean. I’m just like, I think that you could take it at face value and be like, this is actually what he’s doing.

Brian Halligan: I think he was actually doing the thing.

Kareem Amin: Yeah. And I think that’s probably right.

Brian Halligan: And do you think he’s on the right track? Like, he’s got two layers of—like, he’s got a big team working on trying to make all his systems legible, get everything in that legible system. His people are really responsible for making that system as legible as it can be, and then building agents on top of it, and just turning over a lot more of the decision-making over time to—he calls it the intelligence.

Kareem Amin: Yeah, it’s a really hard thing for me to comment on just because I haven’t actually thought about it deeply enough.

Brian Halligan: Yep. Okay, I got a couple more. Just bringing you back to the philosopher king, you’ve got a line, “There’s no elephant in the room, the elephant is in your mind.”

Kareem Amin: I can’t believe he told you that. [laughs]

Brian Halligan: How does that apply to being a CEO?

Kareem Amin: That was an off-the-cuff comment, but if I remember correctly, I have, you know, a Q&A every—it used to be every week, now it’s every other week. And it’s optional, and people show up and we talk about anything. And I think my leadership style or communication style in general is to call the thing out that you might be wondering, and assume that you are a smart person and not kind of like dance around it. And so typically what we do in these meetings is just be like, here are all the things that you might be worried about. So every week actually in my all hands, I talk to people on the team constantly, and I hear various things from them about what’s happening in the company, how’s the culture changing or not changing. And I try to bring these things up so that we can all be aware of them.

Brian Halligan: Yeah.

Kareem Amin: You know, so one of the things …

Brian Halligan: Calling them out.

Kareem Amin: Yeah, calling them out like, hey, people feel like we’re stepping on each other’s toes. And I’m like, okay, let’s discuss that. How does that manifest? What do we want? What behavior do we want?

Brian Halligan: Yep.

Kareem Amin: And I think a lot of the times …

Brian Halligan: So you’re calling the elephant in the room out. What about the elephant in the head?

Kareem Amin: Right. So a lot of the times nothing is happening, and it’s just your anticipation of the problem. Or sometimes we call this like you’re bringing baggage from another company where something happened to you and then you’re like, hey, I don’t trust you guys yet. And so you’re creating the problem because you’re seeing this thing in your head that isn’t even happening in reality. So I’m just like, tell us what’s actually going on so that you don’t work based on some perceived reality that isn’t even real.

Brian Halligan: What do you want to do when you’re old and gray like me? What’s next for you?

Kareem Amin: It’s hard to think about the future, but I happen to be an electrical engineer by training, and I have also been playing more music recently. So I want to be doing a lot of generative ambient music.

Brian Halligan: Okay.

Kareem Amin: I’ve been doing a bunch of stuff like that already.

Brian Halligan: Okay.

Kareem Amin: I don’t know, there’s something around, like, creating soundscapes and getting into that place where, you know, you can’t really—music is all about predicting kind of the next sound. But I’ve really been enjoying this idea of, like, if you can’t predict it, but it’s still like good, what does—you’re expanding kind of like your sound vocabulary.

Brian Halligan: Okay.

Kareem Amin: Yeah.

Brian Halligan: I appreciate your coming on. It was a wonderful conversation. Congrats on all your success.

Kareem Amin: Thank you. Thank you.

Outro

Brian Halligan: Hey everybody. I hope you liked that episode with Kareem. I really enjoyed the conversation. I have a lot of takeaways. I’m gonna give you my three, and I’m gonna give you a couple of stories of my own that tie in. Two nights ago I had dinner with Kareem and David Solomon from Goldman Sachs and Tarek, the CEO of Kalshi. And my takeaway from the dinner was, holy crap, are these three Homo sapiens different! And holy crap, is their CEO playbook different.

And it reminds me of an old quote. You know, I think it goes, “Be yourself, everyone else is taken.” I think it was Oscar Wilde who said it. I leave that with you. I hope you can be yourself because everyone else is taken. There’s a lot of ways to do this. I’m trying to look for the one way. The truth is there’s a lot of ways to be successful as a CEO.

The second thing, he’s sort of a philosopher, and he reminded me of something I’ve been working on. And people say folks who live in the past tend to kind of be depressed, and folks who live in the future tend to be anxious, and folks who live in today seem to be a little bit happier.

I myself tend to live in the future, and I’m kind of anxious. And I remember when my anxiety peaked, and this may be happening to you, so I relay it. I remember doing a company meeting around 100, 150 employees, and just looking out and seeing, oh my gosh, there’s so many people relying on me to make really good decisions. They’re taking care of their kids, they’re paying their mortgages, they’re taking care of their parents in a lot of cases.

It wasn’t actually in the tough times at the beginning. It was when we were actually scaling and starting to do pretty well that my anxiety increased. Anyway, if that’s you, this is just a reminder, living in the present is a good place to be. I’m trying to do more of that myself. Kareem gave me a really good reminder of that.

The third thing is I like his line, “devotion versus discipline.” It’s really hard to scale a startup without real devotion from your employees, and your vision and your story has to be really compelling. If it’s not, you should work on that.

You yourself need to be really compelling. You need to inspire followership. You want people to want to kind of walk across broken glass to work for you. And, like, your company probably has stuff hanging on the walls, you know, slogans and things you come up with, your culture code stuff. It’s incredibly important that you don’t just talk the talk, but actually walk the walk on those slogans.

I’ll leave you with those three. Hope you liked it. I really enjoyed him. See you next time.