The Philosopher CEO | Clay Co-Founder Kareem Amin

23 Jul 2026 · 1 h 9 min · 22 chapters

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In short

Clay (go-to-market engineering) and Kareem Amin’s “philosopher CEO” approach—building from wholeness, committing to reality, creating categories/titles, and aligning teams through clarity while still operating in ambiguity.

Guest backgrounds

Kareem Amin is founder and CEO of Clay. He describes himself as monk-like, contrarian, and intensely reality-focused; he studies CEO patterns and credits an unusual childhood (parents divorced, traveling) with shaping ambition and introspection. He co-founded Clay with Nikolai and previously sold businesses.

Key claims

Ambition should come from wholeness, not lack; success has no “end” beyond the present—enjoy the process. “Reality” and feedback are constant; founders often live in the future and accelerate toward death. Don’t follow performative startup narratives (e.g., 996); tell an honest story and pick the right “hill.” In early startups, “customer centric” isn’t always “listen to customers” first—commit, then flip to customer-centric later.

Notable examples

Varun’s WhatsApp “I’m coming over” friendship with a Clay user; Duolingo as a value-prop misalignment example; category creation via “go-to-market engineering” and “GTM engineers” spreading through agencies/LinkedIn; pricing change handled with transparent docs and compute/data credit bundling; “momentum detective” CEO habit and “go-to-market alpha”/“audiences” feature.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Kareem's Competitive Nature

0:48 to 2:46

Kareem discusses his approach to competition and sportsmanship in Padel, revealing his drive and competitiveness.

“We have Kareem, the founder and CEO of Clayon today.”

Childhood Influences on Ambition

2:46 to 4:35

Kareem explores how his unusual childhood shaped his ambition and perspective on success.

“I'm kind of studying CEOs and I kind of want to see like what are the patterns?”

Creating from Wholeness vs. Lack

4:35 to 5:44

Kareem shares his philosophy of building from a sense of wholeness rather than lack, emphasizing self-acceptance.

“Well, let's say now the company is really successful, right?”

The Illusion of Future Success

5:44 to 7:19

Kareem reflects on the emptiness of future success and the importance of enjoying the present moment.

“or not doing whatever I wanted to, but I was willing to take that risk because it felt more honest to me.”

Reality as Entrepreneurial Feedback

7:19 to 9:10

Kareem discusses reality as a source of feedback for entrepreneurs and the importance of living in the moment.

“here and you're accelerating towards death.”

Contrarian Approach to Building

9:10 to 11:12

Kareem shares his contrarian view on traditional startup narratives, advocating for a more honest approach to building companies.

“I've met with you a few times, but I was on the Sequoia team.”

Clarifying Your Company’s Value Proposition

11:12 to 14:03

Kareem emphasizes the need for clarity on a company's actual value proposition versus assumptions about its function.

“And I just value consistency, for example, and what I found is more useful.”

The Journey of Commitment in Entrepreneurship

14:03 to 18:18

Explore the importance of commitment and perseverance in building a startup.

“Or maybe it helps you stop being anxious.”

Navigating Doubt and Decision-Making

18:18 to 24:16

Learn about overcoming doubts and the nuances in decision-making as a CEO.

“I kind of think of everything as like you're going along, you're making events, it's a dip, and then you come out the other side.”

Creating and Defining Categories in Business

24:16 to 28:00

Understand the process of creating and naming business categories for growth.

“This is kind of like what I tell people around this is we all love startups.”
Show all 22 chapters

Defining Go-To-Market Engineers

28:00 to 32:52

Learn how the term 'go-to-market engineer' was coined and its implications.

“You know, the common advice about this is don't do it, right?”

The Evolution of a Category

32:52 to 36:06

Understand the process of creating and evolving a business category.

“that helped us make all of the other decisions later easy.”

Building Relationships with Agencies

36:06 to 42:00

Explore how genuine relationships foster agency collaborations.

“aggressive with it we didn't want to lose that that makes sense yeah yeah um 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.”

The Value of Transparency in Business

42:00 to 43:10

Learn how transparency can build trust and improve company dynamics.

“Splitting compute and splitting the data.”

CEO as a Momentum Detective

43:10 to 46:12

Explore the unique role of a CEO in identifying and maintaining momentum within a company.

“I was talking to a friend of mine and we're like, hey, this is the term.”

Managing Time and Decision Making

46:12 to 49:15

Understand how to effectively manage time and decision-making processes in leadership.

“And then once I do that for some period of time, typically, you know, typically if that happens too many weeks in a row, I need to stop, delete everything and leave a ton of space.”

Building Trust and Team Dynamics

49:15 to 52:16

Discover the importance of trust and communication in team relationships.

“And with kind of like, let's say playing around with LLMs, there's so many people experimenting.”

Balancing Standards and Forgiveness

52:16 to 56:05

Examine the struggle between maintaining high standards and being forgiving as a leader.

“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 ending weekly one-on-ones I'm Deleting all of those.”

Forgiveness and High Standards in Leadership

56:05 to 58:31

Explore the balance between high standards and forgiveness in leadership.

“things that are not right it's not a dip it's gonna keep going yeah it's not good enough and And I think like I have very high standards and at the same time, I'm very forgiving.”

The Impact of Emotion on Productivity

58:31 to 1:01:42

Discuss how unaddressed emotions impact workplace productivity and dynamics.

“You want to focus on your product and what's unique about you.”

Addressing Issues as a Leader

1:01:42 to 1:04:43

Learn how to identify and address unspoken concerns in a team setting.

Future Aspirations Beyond CEO

1:04:43 to 1:06:30

Kareem shares his future aspirations and passion for music.

“And I hear various things from them about what's happening in the company.”
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Transcript

Automatic transcript. May contain errors.

0:00I 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.

0:47Hey, everybody.

0:49Brian Halligan:We have Kareem, the founder and CEO of Clayon 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 going to like it. 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. He loses quite a bit. And he said, you're relentless and positive and no one tries harder.

1:32Brian Halligan:Where does that come from? I just want to correct the record before we move on. I'm going to call BS on his behalf. 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. He said you guys wager and the wagers increase. And you're like, let's go again. Let's go again. Well, I think, yeah, I think maybe what he's talking about is that I like, you know, especially in sports or things like that. When someone beats me in something, I automatically get charged up rather than charged down.

2:10Sometimes I'm playing actually with Varun against someone else. And if we lose, he wants to change teams, which really baffles me. That actually really gets to me. Because when I lose, I'm like, here's the, 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 in how close we were and how we can kind of get there next time. Whereas he thinks it's less fun and, like, we should switch teams.

2:40Brian Halligan:Where does that come from, little Kareem? Where did you get so competitive? Where does the drive come from? Well, that's a deep cut. Yeah, let's go. You really went there. I'm kind of studying CEOs and I kind of want to see like what are the patterns? Yeah. A lot of CEOs are immigrants. Is it sort of an immigrant edge? 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 a unusual childhood. let's just say just like parents divorced both really great parents just big divorce and you know traveling across like different countries very loud lots of things happening and like my introspection is that the ambition comes from you know the if you like a really simple thing right like if you can do something really big then you'll be loved right um 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 like actually told people at work is that a lot of people think you should build from a place of lack or like 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.

4:11I'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 like often kind of talk about having fun or just like how to enjoy the process because it's actually your life. And otherwise, you're in this like, you know, just in a nightmare scenario in your head trying to prove something and doing so many things in the world. How did you get over that? um there were many insights you sound like people i know who go to hoffman yeah did you go to

4:45Brian Halligan:hoffman no okay you sound like a hoffman alum 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 at the end, 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.

5:26Like, 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 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 not doing whatever I wanted 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 going to work.

6:25You know, you're, you're, this is the feedback.

6:27Brian Halligan:I feel like humans either live in the past, live in the present, live in the future. Founders tend to live in the future and they're anxious about it. Right. I think most founders are probably anxious, anxious folks. Very anxious right now. You're not. I'm not, no. I, at least not in this particular way. My anxiousness is more existential. Tell me about that. But I'll give you like an insight that I had about living in the future. I was on the silent retreat and on like, you know, crazy things happened and I had these like big realizations. And then on day seven out of 10, I was like, oh, I can't wait to go back home and tell everybody about all these things that I realized.

7:11And 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, 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 like 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...

7:39Brian Halligan:It's a very Buddhist thought living in the present. It is a very Buddhist thought. Be calm with yourself. and it but I actually I bet no CEOs are like that except for you I actually think so the funny thing Jack Dorsey probably yeah there's a lot of CEOs that have the or like come to these thoughts at different moments it's 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 who are 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.

8:13It 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 um i i think it actually leads you to make better decisions that are less rushed less confused about like the nature of like what's happening do you dip back into this do you meditate you have a practice every day no so that's the interesting thing i used to have a practice every day when things were more challenging um we'll get into that yeah um i find that i come in and out of it but you know again like some of the thoughts that i've come to our 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 I really what I really like about some of these traditions is that at the end they're like here are all these tools and then at the end they're like drop the tools there is no 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.

9:31Brian Halligan:I've met with you a few times, but I was on the Sequoia team. I'll tell you my reaction. Yeah, please. I was negative on it. Yeah. And I was like, Kareem's not motivated. He's too laid back. He doesn't have a chip on his shoulder. And Alfred Lynette Sequoia gives me crap for this still. I had obviously had it wrong. Do you think a lot of people read you wrong that way? You had a narrative that was just like flies in the face of the narrative I had about what a successful tech founder looks like. I think I'm doing it on purpose. I mean, I'll just say it. But it's not to rub people the wrong way or to push it in their face.

10:09But one, it's probably just like my nature is a little bit contrarian. I find when everybody's doing one thing, it stops being appealing. I'm like an indie person probably versus a pop person but also but and and 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 um when I when I've been in situations where I feel 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 um there's a little of a bit though? For sure. Like it's nothing is one thing or another.

10:49There's a little bit of a bit. I try to catch myself when I'm enjoying it too much and rein it back in. 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 what do you mean by that you brought that up twice like basically take take something like hey the only way to build is 996 blah blah blah right um and it's like what does that do to people who only see that and like new people who have no idea what works and what doesn't are just copying whatever other people are saying um and by the way you need to work extremely hard and in fact I've been working extremely hard for extremely long.

11:40And 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 996. 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 rough unfiltered thoughts but when you look at a business let's say you look at apple i actually

12:32Brian Halligan: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. Yeah, I thought that was interesting too. Why? It's like you don't have a lot of shit going on? Varun's doing everything? He's amazing. Yeah, let's make him CEO. 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, like, ideas.

13:19So it's mainly for me. And especially, like, I'm in, like, a little room alone, you know, there's no distractions. And I think it's an important time right now to, like, think clearly, especially about, you know, what is your value prop? Like, what are you really doing? I think 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. 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 a edutainment game?

13:58Or 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 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.

14:32And those things need to align.

14:33Brian Halligan:I'm going to 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 it's 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 yeah what was that like why didn't you give up um well you heard earlier i'm incapable of giving up i did but you sold businesses before yeah well i thought i mean that's right but i was much that was just like my first attempt and i think i learned one that was a mistake i wouldn't want to do that okay um and number two i think you need to keep going at something to really you know uh well you shouldn't keep repeating the same things that's 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 like lead this thing but you're just at the cusp of actually getting to the point where it gets interesting or you're not or you're not but the difference between those two things is very hard to tell yeah and you need to often push through that the hard part is the part where you think you're getting bored or you think you know because you're you you give yourself a lot of I actually called it like um this is 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 it's actually your board or this thing isn't aligned with your interests or you should do this or that those are all different ways of procrastinating um and not facing the hard thing so one you need to give it enough time to tell yourself for sure it was it actually five years a long time oh yeah so well back to the five years is not that there's i think the five years was a combination really of us it was a spiritual journey i like that you call it the the long you you know, the strange long trip or the long, strange trip.

16:48You've had a very long, strange trip. Yes, 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 going to 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?

17:20What 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 like yes it's five years but really there was like 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.

18:14It just took some time for everybody else to hear about it. But once we committed, it almost worked instantaneously.

18:20Brian Halligan:I kind of think of everything as like you're going along, you're making events, it's a dip, and then you come out the other side. Right. But sometimes not a dip. Sometimes it just keeps going. Right. Did you have doubts that it might keep going? Yeah, tremendous doubts. And did people around you say, like, what are you doing? You're really talented. You could be doing any number of things. yeah tremendous 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 Nikolai like were like 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 like 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 we have 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 like commitment and deciding to do something and I've said it in like 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.

19:57I 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.

20:17Brian Halligan:We didn't listen to the customer like the first seven years. I was the customer. We just blocked out what they wanted. We built what I wanted. And then we flipped it and it became a serum company. And we're very customer centric now. I think companies, the founders are talking about, just focus on the customer. I don't think that's right a lot of times in the early days of a startup. Because everyone can do that. Yeah. Well, let me tell you what I think about this. Because if you're in computer science, hill climbing, you need to pick the right hill. And then listening to customers is kind of fine-tuning it.

20:48But 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 the and it's a reminder to hey it's not about what you know I tell people it's not about what Kareem wants because I I don't want you to listen to me I want you to do the right thing right so and my 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 you and you know what the right feature is, then what I want is Clay to succeed.

21:24I don't want you to do what Kareem, so, you know, people have to be reminded you can't use Kareem told me X as an argument to do something. Unless, there's only very few times where I will tell you 100 % this is what I need you to do.

21:37Brian 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 right i 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 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 right so sometimes in a lot of these companies there's like 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 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 we 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 like superpowers is when you tell me something that I think is capital T truth, I hear it and it sticks, you know?

22:50It's loud. 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 like ability for people to make choices and you need to know which one you're in.

23:11Brian Halligan:I'm going to 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. And people would say, you need to clear the fog. They'd literally say that to me. And I'd be like, okay, there's four decisions that need to be made. Typically, there's one big decision we need to make. 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.

23:48I 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 it. Maybe it's tough trade-offs. 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.

24:18This is kind of like what I tell people around this is we all love startups. They're doing new things. And then it becomes a big company. Now we hate the big company. But the way it becomes a big company is through this somewhat of the path of clarity, the generative phase is messy. So I'd say that like I am capable of holding that mess.

24:42Brian Halligan:To contradict your idea in your head. Yes. Employees 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. Because it's extremely painful. It hurts their head. 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. Yeah. Okay. Just going back to your seven years, five years through the desert in 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 going to work.

25:22Brian Halligan:Yeah. 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 platformy thing and then like we're gonna really like yeah yeah that was very very difficult and I'd say that um well I'll say two things so one is that um 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 um I find you intense which I still am but it's like contained um and directed and hopefully like more you know something that i'd like to open up when necessary um but on the on the point of like picking so i would say that um it was actually my co-founder nikolai 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 yeah and that still lives on in the fact that we called it go-to-market engineering and to like the idiosyncratic way in which like all the features are built to give you that like 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're like okay let's just commit Power and flexibility.

26:53And 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 people, everybody has copied this waterfall enrichment concept, right? But, you know, 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.

27:25That's what actually solves the problem. You can say, like, I want to go from New York to London in, like, one hour. But I can't do that for you. So what's the next best thing?

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27:34Brian Halligan:Yeah. We have a couple things in common between the companies. Very early, we said we're going to create this category called demand marketing. It really worked. You've done the same thing with go-to-market engineering. It appears to be really working. Yeah. everybody and their brother asked me how to create a category. And there's a little bit of magic in it. 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. 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.

28:10You can take something that is happening and name it. That's what we did. Right. And then give it like put a circle around it, be like here, 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, OK, I'm going to name this wave. I'm going to 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 like a term called customer engineer where it's just like it's kind of like forward deployed engineer and we're like what what if you actually the best categories i think are like two words stuck together right um because i think language is evolving like imagine if you had like a rumba what would you call it before you invented like a vacuum you know it would be really hard

29:09Brian Halligan:to name it yep who came up with the name and when you came up with you're like we're going to create a category around it or did it just sort of started happening no so varoon and i were chatting about what we should call our own people who are helping customers fine and then i was like let's just call them go-to-market engineers as opposed to now they might have called it for a deployment engineer yeah or customer engineer but we wanted it to be unique to our thing and and actually credit to uh mike vernal 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 going to do that you know and so when we were like talking about this, we're like, okay, it's go-to-market engineer.

29:44Let's call our own team go-to-market engineers because they're helping you think about your go-to-market in a systematic way. 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 to be for a technical user.

30:22We're going to call them the go-to-market engineer. We're going to 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 seeds. Clear. 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.

30:58Now, 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.

31:09Brian Halligan:Hard to use in PLG typically don't fit. Right. Or not hard to use, but powerful. Powerful, yeah. And so needed to be a type of customer who can pick it up and hack around with it. 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 that's like how it's like a theory of history. and then there was this guy Fjordbach 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 Fjordbach was like actually we're already like 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 wait what's this got to do with go to market so let me let me bring it back for you but this is welcome to my mind okay i like it so to me the interesting thing this is more of a like 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 like 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 sales people if you're in go-to-market and it needs to be super simple and it's seed-based.

32:38Flip 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. Fell out of it.

32:58Brian Halligan:Yes. The name, how did it propagate? So, okay. You called your folks GTM engineers. Yeah. So the go-to-market engineers, I think this is very subtle and very tricky. Because if you go out, I think you guys did a different thing where you were like, we are going to go out and talk about this. We did something very similar. There was SEO and blogging and all this stuff. And we said, that's inbound marketing. And by the way, what was good about it was there was an enemy. No one liked outbound marketing. And outbound marketing was a word. Inbound wasn't. Right. But we just flogged it. We wrote a book.

33:31Brian Halligan:We wrote articles. We did a conference. So we took the exact opposite approach. And again, yeah, 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 going to 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.

34:06And because they needed business. So here's a big.

34:10Brian Halligan:This is the same as us. We educated and we gave them everything they needed to create an inbound marketing agency. Exactly. And 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. If you're using Cloud, you're a go-to-market engineer. Go-to-market engineering, and why I think the category is a category, is that it's a point of view on the world.

34:40It's not a technology. 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 um first the agencies but you need it and again obviously you know this because it's like agencies need the work so they're going to be if you were targeting companies no one wants to tell you how they grew in fact you know 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

35:14Brian Halligan:do you do something that no one can copy right turns out people are followers 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 going to 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. Okay so you come up with a clever name. Right. 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 it's how you did it i would say it quickly spread in certain areas yeah and then we provided some scaffolding around um like we published a couple of articles but we tried to stay in the background of this yeah um we did not we were competing with content marketing at the time yeah and so we were aggressive with it we didn't want to lose that that makes sense yeah yeah um 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.

36:16We thought about it as a title. And I knew that one day it would be the category. We didn't think

36:21Brian Halligan:of it that way. We thought of it as like a new way to go, a new way to market. Right. So, so that yours more title is different. 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 these things it's the storytelling so if you go too early and start telling the story in fact people push back against you uh 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 like 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.

37:04Brian Halligan:We played these same games. They worked. Yes. These things worked. And then we just helped 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? Another thing you have in common with HubSpot is the whole agency thing was a sec we started as direct yes and I was the first salesman and we were quite good at it actually and then we have this one sales trip named Pete Caputa and great name yeah and and we had a lot of agencies interested and I remember was like two three years in I was like products not ready for someone else to sell it not mature enough it's like don't call on them but we also had like like a weekend you could you do anything you wanted on the weekends or after hours kind of like Google's 20 % yeah and one weekend he started calling on him and you just look at the Instagram of the numbers and it's typically a bell curve but he was like 4x the next I guess Pete was right and then we started building a whole program it's like a separate company to engage these people and take care of yeah how how did that happen to you and advice for people who want to create an alternate so many people come to me want to create a second channel and it's very hard yeah it's very hard i mean and we it's you know i don't know that we've fully cracked that but i think that um i would say like a big part of this was varoon as well like we were in whatsapp groups with people who own agencies we we i feel like the the answer that i think people don't really want to know is there's there's no playbook we were being honest and genuinely authentic.

38:54The mission is how do we help companies grow? And we're like, we're going to 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, he's, 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.

39:35And 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. We had the same. Yeah. And we were just kind of on that journey with them, truly. 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? That's their top thing is they can read your intention. So if you're going to go there and fake confidence, that's not going to work.

40:14You need to truly believe that you have the magic sauce.

40:19Brian 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 getting punched in the face by the market. And you just kind of get punched. I don't actually care that much about the pricing. Talk about the backlash to it and talk about what you did and kind of your philosophy around it. I would say the backlash is minimal, or at least we perceive it to be minimal. It's so loud to me. Right. I think like we did a bunch of like analysis around like sentiment analysis on some of these things.

40:54And we're like it was like 70 percent neutral, you know, somewhat some negative people. And I think all the people that were quite negative or loud about it had some self-interest. So, you know, they own 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 the way that we dealt with it i think that's the interesting part 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 f uv or whatever but now it's completely sold out okay um so anyway back to like our pricing change though the things that help us withstand something like that is like One, what is our conviction in our thinking?

41:43So we're like, hey, we bundled credits. Credits cost data and what 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. Splitting compute and splitting the data. Right, exactly. on it and so now that we have compute and data and we trusted the sophistication of our like 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 trans it literally was word for word what we were saying internally in our meetings.

42:35And that's a common thing for us in the way that we operate. And I think maybe unusual and surprising to people. Yeah, it disarms them. Yeah. And it goes back to this, like, really equals trust.

42:48Brian Halligan:It's not even correlated with it's like equals it. It equals trust. Yeah. And in order to do that, you need the right channel, 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 um and then other people will actually read it and digest it yeah i i thought that was very well handled um i want to kind of shift to kind of you as ceo what's your day like um i have like two terms for it one is i'm a momentum detective right so i just go around the company and i love this yeah i find momentum is so hard to get if you lose it and so anytime you see a 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 oh so you don't hop on where the momentum's hot you hop on when it's starting to wane yes so well it's both right um 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 varoon write that article but like 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.

44:20I was talking to a friend of mine and we're like, hey, this is the term. And then I went back and I was talking to a couple of people that resonated with them. And we're like, this is it. Now we use this in all of our, and you know, people initially were like alpha, that sounds like really nerdy, you know. Customers are nerdy. Right. But, 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, 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.

44:52I'll give you another idea. We needed a feature that we call audiences, which allows you to have 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. People like what about our tables well like we don't want this to have table limits no role limits no cell size limit a lot of the limits that we just remove it so I had to motivate it in a different way it wasn't getting traction which is kind of interesting but it was 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 going to aggregate it out well you need this concept of an audience which we were talking about before um and that like you know 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 even if so one of the things I think you realize CEO is that you are sometimes way ahead of everybody else 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

46:31Brian Halligan:this for so long yeah momentum detective I love that right you're good at branding by the way apparently all your clay agency all that stuff you're very clever at it uh you've got kind of two modes yeah i i think there's the 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 advice on how to do that for other ceos um so actually my head of people told me that i'm uh 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 they had like a bunch of problems right and it was like there are many there are many problems that seem like they're the problem but often if you listen and apologizing doesn't mean necessarily that something 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 just very tactically like your day do you leave a lot of open time to momentum surf are you packed every half hour 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 So, you know, it's recruiting, product decision making, listening to someone removing a problem, comp issues, you know, talking to partners.

48:09All the things. All the things. And then once I do that for some period of time, typically, you know, typically if that happens too many weeks in a row, I need to stop, delete everything and leave a ton of space. I prefer 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 exact team meeting, which I think people find bizarre. How do you stay aligned, all that stuff. 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.

48:54and the other way where everything is packed works but it's 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

49:15Brian Halligan:time 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 right how do you fit that in is that weekends or that has to be that has to be after work weekends etc 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 um but again like i i 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 um and then process that and then come up with a decision um rather than you you can't just rely on like your firsthand experience of like, I, you know, I built a lot of the initial product with my co-founder.

50:16So 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, 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. I'm trying to soak that in. The firsthand knowledge is limited.

50:38Brian Halligan:Do you have one-on-ones or you're like, you know, what do you think about that? How many direct reports do you do one-on-ones? So the... These are just tactical things. Yeah, the tactical things. People ask me all the time. 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, we did exactly that for our first five years. 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 six, 70 people.

51:18I see. Without a head of edge until last September. OK, that was a lot. 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.

51:35Brian Halligan:Stay close to it. Yeah. 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. Yes. It's a little they can be draining. Very draining. Where are you on that? 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 like doing some new project I'd rather have one-on-ones with that person so it's I'm trying to do it actually with 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 the like 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 ending weekly one-on-ones I'm Deleting all of those.

52:31Yeah.

52:33Brian Halligan: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. 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. Interesting, yeah. Similar? Yeah, so did you change that as people talked to you about it? I tried to. It didn't. Yeah. Honestly, it didn't really work. Trust is hard to build with me. Yeah. I think that I have a similar thing. I'm not, I have like trust issues for sure. Yeah. But it's like different, I mean, there's different levels of trust.

53:09So there's like real trust, which I have with a handful of people. That's what I'm talking about. Yeah, that's what you're, what people have said to me is that I'm too forgiving. So I would say I have like one kind of like 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 give you tons of like I'm actually angry right now. I'm annoyed over time. Do you hold on to people too long? Definitely. But it has worked out sometimes. I keep hearing people are like it's never worked out.

53:51I would say that we are 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 the wrong context you get the worst out of someone so there have been situations where something seemed completely off and I like listen to this person did the exact opposite of what everybody you know like I'll give you an example that would seem absurd right as someone did something wrong um and it doesn't matter what the details are but uh i gave them an increase in salary why right now that seems crazy because i seems like something contrarian ceo 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 structural things held them back and it was out of like partially out of the fact that they were not being paid correctly okay fine so but 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 okay i heard i've heard

55:03Brian Halligan: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 right that's good yeah i told him that i feel like it's uh um i thought i by the way i agree and 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 it it people are having fun um and sometimes they that's you yeah they're like you know there there's an absurdist kind of like feeling to the company it feels like put I don't know it's like a post-modern painting you know there's stuff and then everything has its counter point 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 it's not a dip it's gonna keep going yeah it's not good enough and And I think like I have very high standards and at the same time, I'm very forgiving.

56:17And so I think that.

56:19Brian Halligan:Where does that come from? The very forgiving part? High standards. Is that mom? Is that dad? Where's that? Yeah, I think the I mean, the high standards, I feel like it's like taste. My parents like have high standards. But and the forgiving part. Yeah, it probably is like my dad is very forgiving. but I think it also is like back to kind of like why are we doing this 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 co-worker 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 have like you know 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.

57:49And 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. And also by perpetuating kind of like, I actually think, this is a pet theory that I have, is that very few people get to this stage of company, right? And it's very, when you're in it, it's very, you know, you're kind of trying to stay exactly on the line of success.

58:29so 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 will 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.

58:56Brian Halligan:Hire slow, fire fast. Yeah, higher, slow, fire, fast. You don't believe in that? You obviously don't. You just said the fire. 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 thinking about the situation. You're just following the rule. What other CEO-isms do you think are stupid? A lot. Like? I think driving people really hard without paying attention to... I'll give you one example. People come in and they're like, AI is going to create a ton of productivity.

59:36We should fire 20 % of the team without knowing what you're actually doing. And that's what 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, like, the team. And I feel that sometimes, too, it's like management, you know, it's like the principal agent problem, management versus, like, workers, where you're like, why aren't people thinking correctly? Why aren't they, you know, taking action? Why aren't they, like, owning this? Well, their incentives aren't aligned for that.

1:00:12Anyway, I also think that thinking of work, this is a big one for me. rather 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 um is not always the optimal you need you need the whole toolkit so like you know another word for discipline could be the fear and greed thing that's those are the those are all levers by the way yes how do you think about that um i'm i'm uh i believe in like 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 motivate 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 like some of my own that feels like you're just trying to take this thing and hand it to someone else.

1:01:18Like it's like a musical chairs thing, right? So like 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, well, 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 going to 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 like 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'm I don't want to do that because I don't want to live with myself in this way.

1:02:04Brian 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 he's 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 put ai in the center and he's delegating a lot of decisions to the center that people are on the outside he's rethought his org chart his compensation he's sort of reimagining it i assume you're following some of that what's your take i think that you know it's hard with like public companies too because it's like you what is the narrative versus what's reality i do think that sometimes you do need to retool the company um and maybe you hire too many people or maybe things are changing um and we don't have really good ways in general to say the truth without um 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 i don't think he was covering it up 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 i think he's actually doing the thing yeah and i think that's probably right and do you think he's on the right track um like he's got two layers of like he's a crazy flat he's got a big team working on us trying to make all the 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 yeah it's a really hard thing for me to comment on just because i haven't actually thought about it deeply enough yeah 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 I can't believe he told you that.

1:04:03Brian Halligan:How does that apply to being a CEO? That was an off-the-cuff comment, but if I remember correctly, I have a Q &A every week. 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.

1:04:46And I hear various things from them about what's happening in the company. How is the culture changing or not changing? And I try to bring these things up so that we can all be aware of them. Yeah. You know, so one of the things. Calling them out. Yeah, calling them out. Like, hey, people feel like we can't, 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? And I think a lot of the times...

1:05:14Brian Halligan:So you're calling the elephant in the room out. What about the elephant in the room? So a lot of the times nothing is happening and it's just your anticipation of the problem. Fine. 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. What do you want to do when you're old and gray like me?

1:05:52Brian Halligan:What's next for you? 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. um so i want to be doing a lot of like generative ambient music okay i've been doing a bunch of stuff like that already okay i don't know there's something around like creating soundscapes and getting into uh like that place where you know you can't really i 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 but it's still like good what does you're expanding kind of like your sound vocabulary okay yeah i appreciate your coming on this is a wonderful conversation congrats on all your success thank you thank you hey everybody i hope you liked that episode with kareem i really enjoyed the conversation i have a lot of takeaways i'm going to give you my three and i'm going to give you a couple stories of my own that tie in uh two nights ago i had dinner with kareem and david solomon from Goldman Sachs and Tarek, the CEO of CalShe.

1:06:59Brian Halligan: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 the 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.

1:07:48Brian Halligan: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 increase. Anyway, if that's you, this is just a reminder.

1:08:23Brian Halligan: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. Your vision and your story has to be really compelling and 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 to talk but actually walk the walk on those slogans on the wall I'll leave you those three.

1:09:15Brian Halligan:Hope you liked it. I really enjoyed him. See you next time.

From the publisher

I had Kareem Amin all wrong. When Clay first crossed my radar, I thought he was too laid-back:  no chip on his shoulder, not the hungry founder I expected to win. Clay has since exploded.

Kareem builds from what he calls "a place of wholeness" rather than lack — nothing to prove, no enemy to beat. It makes him sound like a philosopher, but the operating instincts underneath are sharp. He spent roughly five years wandering before Clay clicked, and his takeaway is that the hard part of building isn't working hard — it's the courage to commit to one idea and stop listening to everyone else, customers included. He flipped every assumption in his market: sell to technical "go-to-market engineers," charge for usage instead of seats, pick power over simplicity.

We both created categories, in opposite ways. I flogged "inbound marketing" with a book, a conference, and relentless content. Kareem coined "go-to-market engineering" and then refused to take credit, letting agencies own it because a category has to be bigger than you. We also get into his "momentum detective" theory of the CEO job, why he's deleting his standing one-on-ones, and why apologizing is one of his sharpest tools. There's no single way to run a company. Kareem is my proof.

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