The Philosopher CEO | Clay Co-Founder Kareem Amin

Summary

Podcast Summary

Podcast: Long Strange Trip: CEO to CEO with Brian Halligan
Episode: The Philosopher CEO | Clay Co-Founder Kareem Amin
Host: Sequoia Capital
Date: July 23, 2026
Guests: Kareem Amin (Co-founder & CEO, Clay), Brian Halligan (Host)

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Overview

This episode features Kareem Amin, co-founder and CEO of Clay, in a deep and candid conversation with Brian Halligan. Titled "The Philosopher CEO," the episode explores the unconventional leadership philosophy that has defined Clay’s rise, Kareem’s personal journey through five years in the “desert” before finding product-market fit, and the core beliefs that shape his day-to-day approach. The episode is a rich blend of tactical insights, career reflections, and nuanced commentary on what it means to lead a modern, fast-growing tech company outside Silicon Valley’s orthodoxy.

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Key Themes and Discussion Points

1. Authenticity and Building from a Place of Wholeness

• Kareem’s Motivation: Kareem shares how his drive originally stemmed from “a place of lack”—trying to prove himself due to a tumultuous, multicultural upbringing and a desire to be loved for big achievements ([03:01]). Over time, he intentionally shifted to building from a place of wholeness and acceptance.

  “If you can do something really big, then you'll be loved. ... But I think you create a lot of damage along the way. 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.” (Kareem, [03:01])

• Building Genuine Relationships: Success for Kareem means genuinely caring about others’ success—even when nurturing an agency channel:

  “I want to make these people successful. And they felt that genuineness... we were just kind of on that journey with them, truly.” ([00:00], [39:01])

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2. Competitive Fire vs. Present-Minded Calm

• Contradictory Traits: Despite being perceived as “laid back,” Kareem underscores his quiet intensity—a relentless urge to keep trying, particularly when losing ([01:58]).

  “When someone beats me in something, I automatically get charged up rather than charged down... I can see that difference and how close we were and how we can kind of get there next time.” (Kareem, [01:58])

• Present Over Anxiety: Kareem has worked intentionally to avoid the typical CEO’s future-focused anxiety:

  “At the end there's nothing at the end of success... it's just right now, like, how do I feel right now? ... If I wasn't enjoying it at the end, you get to the end and you didn't enjoy it.” ([04:48])
  “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." ([06:54])

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3. Rejecting the CEO Playbook (996 and Performative Hustle)

• Challenging Industry Norms: Kareem pushes back on the “996” culture and myth of the chip-on-the-shoulder CEO:

  “The dominant narrative around how to build things... 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?” ([10:56])

• Consistency over Extremism:

  “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.” (Kareem, [11:18])

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4. Finding Product-Market Fit: The 5-year ‘Desert’

• Commitment and Introspection: Clay wandered through years of pivots and uncertainty before “committing”—a lesson about choosing focus over chasing ever-bigger ambitions.

  “We had a lot of really good ideas. We did a little bit of each... 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.” ([16:32])

• The Hard Part:

  “What was hard was having the courage for people... to be like, hey, we're just gonna pick this thing. I don't care how silly it sounds. ... When I decided to commit, I stopped listening to everybody. ... If you listen to the wrong people at the time, when it's like a small idea, you kill it.” ([19:13])

• Timing and Market:

  “Once we committed, it almost worked instantaneously.” ([17:53])

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5. Philosophy of Category Creation (“Go To Market Engineer”)

• Observing, Not Forcing: Kareem describes category creation as “naming something that’s already happening and giving it a fuzzy boundary” ([28:01]).

  “You can’t create a category. You can take something that is happening and name it. ... For us, the way we did it was one, we started noticing people use the term GTM instead of sales... We used to have like a term called customer engineer... The best categories are like two words stuck together.” ([28:14])

• Title Before Category:

  “We thought about it as a title, and I knew that one day it would be the category.” ([36:09])

• Letting Others Own It:

  “We try to not take credit for it or be involved in the conversation and we leave the conversation open.” ([34:10])

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6. Channel Building with Agencies

• Playbookless, Genuinely Relationship-Driven:

  “We were being honest and genuinely authentic. The mission is, how do we help companies grow? ... Actually, I want to make these people successful. ... We built genuine, authentic friendships with a lot of the people. ... 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.” ([38:29])

• “Helping, not Selling”:
  Kareem and team would literally go above and beyond, e.g., visiting a user’s house to solve problems ([00:00], [39:01]).

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7. Handling Pricing Backlashes

• Transparency as Disarmament: When a controversial pricing change attracted criticism:

  “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 I think maybe unusual and surprising to people, it disarms them.” ([41:21], [42:44])

• Data-Driven & Honest:

  “It was like 70% neutral, some negative people. ... We haven't seen kind of that negativity show up in the numbers.” ([40:48])

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8. Operating and Leadership Style

• Momentum Detective:

  “I’m a momentum detective. ... Every time 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 going.” ([43:21])

• People and Apologies:

  “I’m the only CEO [my Head of People] has worked with that has apologized. ... Apologizing doesn't mean necessarily 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.” ([47:01])

• No Exec Meetings, Just-In-Time:

  “We don’t have an exec team meeting... Call me whenever, and then we resolve it. Otherwise, people wait for the meeting, as you know.” ([48:10])

• Forgiveness and Culture:

  “I have very high standards and at the same time, I'm very forgiving. ... The way that I'm interacting with people at work... this is a microcosm... if you can't forgive your coworker... how are we going to make this work?” ([56:19])

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9. Philosophy, Devotion, and Discipline

• Devotion as Motivation:

  “Devotion is as good as discipline. You can't just use some of these tools without understanding both. ... You need the whole toolkit.” ([60:52])

• Skepticism of CEOisms:

  “Hire slow, fire fast—you don't believe in that. ... At some point, you shut down internally, you stop like thinking about the situation. You're just following the rule.” ([59:17])

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10. Self-Awareness, Introspection & The CEO’s Mind

• On Trust Circles:

  “I have like trust issues for sure. ... There's real trust, which I have with a handful of people.” ([52:59])

• On Company Culture as a Founder’s Exaggeration:

  “I feel like people seem really open and enjoy working together... that's the feedback that we constantly hear is that people are having fun.” ([55:22])

• On "Elephants in the Room":

  “Nothing is happening and it's just your anticipation of the problem. ... You're creating the problem because you're seeing this thing in your head that isn't even happening in reality.” ([65:17])

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Notable Quotes & Memorable Moments

• On Ambition vs. Contentment
  “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.” (Kareem, [04:48])

• On Leading with Contrarianism
  “My nature is a little bit contrarian. When everybody's doing one thing, it stops being appealing. ... I'm like an indie person probably versus a pop person.” (Kareem, [10:00])

• On ‘The Desert’
  “We wandered through the desert for a long, long time and then you found product market fit and it really ripped.” (Brian, [14:33])

• On Engineering Category Creation
  “The best categories, I think, are like two words stuck together.” (Kareem, [28:14])

• On Pricing Transparency
  “It literally was word for word what we were saying internally in our meetings. ... Belief equals trust.” (Kareem, [42:42])

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Timestamps for Key Segments

| Timestamp | Segment | |---------------|----------------------------------------------------------------------------------------------| | 00:00–02:40 | Kareem’s approach to customer and founder relationships (genuine investment in user success) | | 03:01–06:28 | The roots of Kareem’s ambition and shift to building from wholeness | | 06:40–08:45 | Anxiety, present-moment thinking, Buddhist philosophy | | 10:00–14:33 | Contrarian leadership and skepticism of hustle culture | | 14:33–20:00 | The five-year journey to product-market fit and the psychology of persistence | | 28:01–34:10 | Creating and propagating "Go To Market Engineer" as a category and title | | 38:29–39:54 | Building the agency channel through authentic friendships and grassroots relationships | | 40:43–42:44 | Handling pricing change backlash with radical transparency | | 43:21–47:01 | Kareem’s operating style: "Momentum Detective," apologizing, and trust-building | | 48:10–49:15 | No fixed “exec meetings”; preferring open, just-in-time decision making | | 55:16–56:07 | Company culture as an exaggeration of the founder's traits | | 65:17–65:48 | "No elephant in the room; the elephant is in your mind"—calling out organizational anxiety |

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Conclusion

This episode challenges canonical startup and CEO playbooks, favoring a compassionate, introspective, and often counterintuitive approach to leadership. Kareem Amin operates in ambiguity, builds on trust, and isn’t afraid to blend forgiveness, devotion, and discipline as the situation requires. He combines present-mindedness with a relentless, competitive drive, and his strategies for category creation, partner enablement, and team alignment are rooted in both philosophical reflection and tactical clarity.

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Final Quote:
“Be yourself. Everyone else is taken.” (Oscar Wilde, invoked by Brian, [66:41])

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For further listening:

• Listen to previous episodes for more on redefining what it means to be a CEO in the current era of tech.
• Recommended for founders, execs, and those reconsidering what a leader can be in modern tech organizations.

Transcript

[Kareem]

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]

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 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. You had to 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]

He loses quite a bit, and he

[Brian]

said, you're relentless and positive, and no one tries harder. Where does that come from?

[Kareem]

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

[Brian]

I'm going to call BS on his behalf.

[Kareem]

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]

He said, you guys wager, and the wagers increase and that you're like, let's go again. Let's go again.

[Kareem]

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. Sometimes I'm playing actually with Varun against someone else, and. 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 and how close we were and how we can kind of get there next time, whereas he want. He thinks it's less fun and, like, we should switch teams.

[Brian]

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

[Kareem]

Well, that's a deep cut.

[Brian]

Yeah, let's go.

[Kareem]

You really went there.

[Brian]

Yeah. I'm kind of studying CEOs, and I kind of want to see, like, what are the patterns?

[Kareem]

Yeah.

[Brian]

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

[Kareem]

I'll tell you. Kind of like where I've gotten to after thinking about that or analyzing. 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 traveling across different countries, very loud. Lots of things happening. And 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. 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 it. 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 of. 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. 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, 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 nightmare scenario in your head trying to prove something and doing so many things in the world.

[Brian]

How did you get over that?

[Kareem]

There were many insights.

[Brian]

You sound like people I know who go to Hoffman.

[Kareem]

Yeah.

[Brian]

Did you go to Hoffman? No. Okay. You sound like a Hoffman alum.

[Kareem]

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, like, how do I feel right now? Why am I doing, 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. And also I took the risk of saying that may end up leading to the ambition disappearing or, you know, 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. This is the feedback I feel like

[Brian]

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. I think most founders are probably anxious folks.

[Kareem]

Very anxious right now.

[Brian]

You're not?

[Kareem]

I'm not, no. At least not in this particular way. My anxiousness is more existential.

[Brian]

Tell me about that.

[Kareem]

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 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, 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.

[Brian]

It's a very Buddhist thought. Living in the Buddhist.

[Kareem]

It is a very Buddhist thought.

[Brian]

Be calm with yourself.

[Kareem]

And it. But I actually.

[Brian]

I bet no CEOs are like that except for you.

[Kareem]

I actually think so.

[Brian]

The funny thing, Jack Dorsey, probably.

[Kareem]

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. It doesn't mean you. 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, like, what's happening.

[Brian]

Do you dip back into this? You meditate? You have a practice every day?

[Kareem]

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

[Brian]

We'll get into that. Yeah,

[Kareem]

I find that I come in and out of it. But, you know, again, like, 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 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 path. You know, I can't teach you one way or another. You just have to see what it's like by living.

[Brian]

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

[Kareem]

Yeah, please.

[Brian]

I was negative on it. And I was like, kareem's not motivated. He's too laid back. He doesn't have a chip on his shoulder. And Alfred Linnitzikoi 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 was just like flies in the face of the narrative I had about what a successful tech fellow.

[Kareem]

I think I'm doing it on purpose. I mean, I'll just say it. That's I. But it's not. Not to like rub people the wrong way or to like push it in their face. But one, it's probably just like 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. But also, but. 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 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. There's a little bit of a bit though, for sure. Like it's 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]

I see.

[Kareem]

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]

What do you mean by that?

[Kareem]

The damage.

[Brian]

You brought that up twice.

[Kareem]

Basically take something like, hey, the only way to build is 996, blah, blah, blah, right? 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. 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 like honest to where you're at and what you need to do.

[Brian]

And.

[Kareem]

And sometimes you do need to work 9, 9, 6. But to me that was like, well, maybe you don't have a moat or maybe you need to do something so extraordinary, right, 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.

[Brian]

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. Yeah. I think it's interesting you took two days out of your schedule to do that.

[Kareem]

Yeah, I thought that was interesting too.

[Brian]

Yeah.

[Kareem]

Yeah.

[Brian]

Why? It's like you don't have a lot of shit going on. Varun's doing everything.

[Kareem]

He's amazing. Yeah, let's make him CEO, everyone. 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 like, ideas. So 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? 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? 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]

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. 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?

[Kareem]

Well, you heard earlier I'm incapable of giving up.

[Brian]

I did. But you sold businesses before.

[Kareem]

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 didn't want to do that.

[Brian]

Okay.

[Kareem]

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. That's usually the door is right next to you. But I have this issue actually, even with people at the company where 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]

Or you're not.

[Kareem]

Or you're not. But the difference between those two things is very hard to tell 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 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 and not facing the hard thing. So one, you need to give it enough time to tell yourself for sure.

[Brian]

Was it actually five years is a long time?

[Kareem]

Oh, yeah.

[Brian]

So.

[Kareem]

Well, back to the five years is not that there was. I think the five years was a combination really of us. It was a spiritual journey. I like that you call it the long, you know, the strange long trip

[Brian]

or the long strange trip you've had a very long, strange trip.

[Kareem]

Yes, it is a very long, strange trip. But for me, it was actually mostly around deciding and committing to what we're building. 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? 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, 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. It just took some time for everybody else to hear about it, but once we committed, it almost worked instantaneously.

[Brian]

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

[Kareem]

Right?

[Brian]

But sometimes not a dip. Sometimes it just keeps going.

[Kareem]

Right.

[Brian]

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]

Yeah, tremendous, tremendous doubt, 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, 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's 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, 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]

We didn't listen to 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. Well, it's really, I think companies, this founder just 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]

Well, I think it's like.

[Brian]

Because everyone can do that.

[Kareem]

Yeah. Well, let me tell you what I think about this, because it's like, if you're like, you know, 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. 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 to, hey, it's not about what you know, I tell people. It's not about what Karim wants because I don't want you to listen to me. I want you to do the right thing, right? So. 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. Unless there's only very few times where I will tell you 100%, this is what I need you to do.

[Brian]

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, 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?

[Kareem]

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.

[Brian]

You know, it's loud.

[Kareem]

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.

[Brian]

Okay, 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 it'd be like, okay, there's four decisions that need to be made. Or 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.

[Kareem]

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

[Brian]

and don't want to make trade offs.

[Kareem]

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 like the path of clarity. The generative phase is messy. So I'd say that like I am capable of holding that mess and two

[Brian]

contradictory ideas in your head and continue to not. I would ask people to do it and they do it for a little while and be like, I don't want

[Kareem]

to do that anymore because it's extremely painful.

[Brian]

It hurts their head.

[Kareem]

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]

Yeah, okay. Just going back to your seven year, five years through the desert. In your two years, at some point you said you had a very broad vision and then you're like, this one use case is going to work.

[Kareem]

Yeah.

[Brian]

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 narrowing.

[Kareem]

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 perceived 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]

I find you intense, which I still

[Kareem]

am, but it's like contained and directed and hopefully like more, you know, something that I like to open up when necessary. But on the, on the point of like picking. So I would say that it was actually my co founder, Nikolai, who identified this segment and, and use case. And I was finding it very challenging to commit to this. And I think he was too. Cause I'm like, how is this related to like, you know, we wanted to give the power of programming to more people. 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 were like, okay, let's just commit power and flexibility 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 people. 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, 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]

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 Engineer. It appears to be really working. Everybody and their brother asked me how to create a category and there's a little bit of magic in it. 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]

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

[Brian]

That's what we did.

[Kareem]

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, okay, 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? We used to have like a term called customer engineer where it was just like, it's kind of like forward deployed engineer. And we're like, 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 like Roomba, which, what would you call it before you invented like a vacuum? You know, it would be really hard to name it.

[Brian]

Yep. Who came up with the name? And when you came up with it, you're like, we're going to create a category around it or did it just sort of started happening?

[Kareem]

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

[Brian]

Fine.

[Kareem]

And then I was like, let's just call them Go to market engineers as

[Brian]

opposed to now that you might have called it forward deploy an engineer.

[Kareem]

Yeah, or customer engineer. But we wanted it to be unique to our thing and actually credit to 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? 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. 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, we'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 over simplicity? 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, hard to

[Brian]

use in plg typically don't fit right. Or not hard to use, but powerful.

[Kareem]

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 like idea of like 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 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 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.

[Brian]

What's this got to do with go to marketing?

[Kareem]

So let me bring it back for you. But this is welcome to my mind.

[Brian]

Okay, I like it.

[Kareem]

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 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 salespeople. If you're in, go to market. And it needs to be super simple and it's seed 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.

[Brian]

Easy fell out of it.

[Kareem]

Yes.

[Brian]

The name, how did it propagate? So you called your folks GTM engineers.

[Kareem]

Yeah. So the Go to Market engineers. This is a. 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.

[Brian]

We did something very similar like 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.

[Kareem]

Right.

[Brian]

And outbound marketing was a word. Inbound wasn't right. But we just flogged it. Like we wrote a book, we wrote articles, we did a conference.

[Kareem]

So we took the exact opposite approach. And again, which is like, don't. I mean, some people don't even know that we came up with this. Right. So it's kind of like you need to think of concentric circles that it's going to involve. 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]

This is the same as us. Like, we educated and we gave them everything they needed to create an inbound marketing agency.

[Kareem]

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 using, 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. It'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 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, 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]

Turns out people are followers.

[Kareem]

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.

[Brian]

Okay. So you come up with a clever name.

[Kareem]

Right.

[Brian]

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]

I would say it quickly spread in certain areas. 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]

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

[Kareem]

Yeah.

[Brian]

And so we were aggressive with it. We didn't want to lose that.

[Kareem]

That makes sense.

[Brian]

Yeah.

[Kareem]

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]

We didn't think of it that way. We thought of it as like a new way to market.

[Kareem]

Right.

[Brian]

Yours is more a title. It was different.

[Kareem]

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 earn 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. 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.

[Brian]

We played these same games. They worked. Yes, things work.

[Kareem]

And then we just help them. But. 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]

Another thing you have in common with HubSpot is the whole agency thing. We started as direct, 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 great name. 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 him. But we also had a weekend. You could do anything you wanted on the weekends or after hours, kind of like Google's 20% time. And one weekend he started calling on him. And you 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 these people and take care of them. 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.

[Kareem]

Yeah, it's very hard. I mean, and I don't know that we've fully cracked that, but I think that I would say a big part of this was Varun as well. 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 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 claim. 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. So we built genuine, authentic friendships with a lot of the people. And some people left their job to start clagencies. Yeah. And we were just kind of on that journey with them, truly.

[Brian]

Yeah.

[Kareem]

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

[Brian]

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 your philosophy around it.

[Kareem]

I would say the backlash is minimal, or at least we perceive it to be minimal.

[Brian]

We did something loud to me.

[Kareem]

Right. I think we did a bunch of like analysis around, like sentiment analysis on some of these things. And we're like. It was like 70% 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 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

[Brian]

dealt with it, I think that's the interesting part.

[Kareem]

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. Okay. 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. So we're like, hey, we bundled credits, credits cost data and what value we provide. And we were big enough at this point to, 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]

Splitting, compute and splitting the data.

[Kareem]

Right, exactly.

[Brian]

Got it.

[Kareem]

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

[Brian]

to people, it disarms them.

[Kareem]

Yeah. And it goes back to the belief equals trust.

[Brian]

It's not even correlated with. It's like equals it.

[Kareem]

It equals trust. 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 going to actually show all of our work even though it's long, and then other people will actually read it and digest it.

[Brian]

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]

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 going.

[Brian]

Oh, so you don't hop on where the momentum's hot, you hop on when it's starting to wane.

[Kareem]

Yes. So. 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 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. 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. 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. I'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 were like, what about our tables? Well, we don't want this to have table limits. No row 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 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 audiences, which we were talking about before, 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 this for so long.

[Brian]

Yeah. Momentum Detective, I love that.

[Kareem]

Right.

[Brian]

You're good at branding, by the way. Apparently all your agencies, all that stuff. You're very clever at it. You've got kind of two modes.

[Kareem]

Yeah, 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 funk. And I remove that advice on how

[Brian]

to do that for other CEOs.

[Kareem]

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. 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.

[Brian]

Just very tactically, like your day, do you leave a lot of open time to Momentum Surf? Are you packed every half hour?

[Kareem]

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, talking to partners.

[Brian]

All the things.

[Kareem]

All the things. And then once I do that for some period of time, 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 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]

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 you block that kind of thing.

[Kareem]

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 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 and then process that and then come up with a decision rather than. You can't just rely on your firsthand experience of like 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 play around with it. And with kind of like let's say playing around with lms there's so many people experimenting. I'm trying to soak that in. The firsthand knowledge is limited.

[Brian]

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]

So the, these are just tactical things.

[Brian]

Yeah, the tactical things people ask me all the time.

[Kareem]

So right now I probably have seven direct reports. I've been limiting. I'm actually just so I, I've. 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

[Brian]

our first five years.

[Kareem]

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 seventy people. I see without a head of ENG until last September.

[Brian]

Okay. That was a lot.

[Kareem]

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. I wanted to keep that.

[Brian]

Stay close to it.

[Kareem]

Yeah.

[Brian]

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]

Yes.

[Brian]

It's a little salt. They're. They can be draining.

[Kareem]

Very draining.

[Brian]

Where are you on that?

[Kareem]

I think that it's draining. I've removed one on ones I. I have one on ones with. So now actually my. 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 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 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.

[Brian]

You're expanding weekly one on ones.

[Kareem]

I'm deleting all of those.

[Brian]

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. 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]

Interesting.

[Brian]

Similar.

[Kareem]

Yeah. So did you. Did you change that as people talk to you about it?

[Brian]

I tried to. It didn't.

[Kareem]

Yeah.

[Brian]

Honestly, it didn't really work. Trust is hard to build with me.

[Kareem]

Yeah. I think that I have a similar thing. I'm not. I have like trust issues for sure.

[Brian]

Yeah.

[Kareem]

But it's like different. I mean there's different levels of trust. So there's like real trust, which I have with a handful of people.

[Brian]

That's what I'm talking about.

[Kareem]

Yeah. That's what people have said to me is that I'm too forgiving. So I'd say I have like one. 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, you know, give you tons of like, I'm. I'm actually angry right now. I'm annoyed over time.

[Brian]

Do you hold on to people too long?

[Kareem]

Definitely. But it has worked out sometimes.

[Brian]

Okay.

[Kareem]

I keep hearing, you know, people are like, it's never worked out. I 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. With the wrong context, you get the worst out of someone. So there have been situations where something seemed completely off and I listened to this person did the exact opposite of what everybody. I'll give you an example. That would seem absurd. Someone did something wrong and it doesn't matter what the details are, but I gave them an increase in salary.

[Brian]

Why?

[Kareem]

Now that seems crazy.

[Brian]

Seems like something a contrarian CEO would do.

[Kareem]

Now that person is one of the best, 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.

[Brian]

Okay, fine.

[Kareem]

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]

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.

[Kareem]

Right. That's good. Yeah, I told them that. I feel like it's a.

[Brian]

By the way, I agree.

[Kareem]

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's. People are having fun and sometimes they.

[Brian]

That's you.

[Kareem]

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 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. Patient. With things that are not right.

[Brian]

It's not a dip. It's going to keep going.

[Kareem]

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]

Where did that come from?

[Kareem]

The very forgiving part.

[Brian]

High standards. Is that Mom? Is that dad? Where's that?

[Kareem]

Yeah, I think the. I mean, the high standards, I feel like it's like, taste. My parents, like, have high standards. 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 if you can't forgive your coworker for some infraction or some random thing they said to you or some 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 the stakes might be lower in some ways. That's why we have. 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. Sometimes people are going through crazy cycles of emotional things because I made some random comments 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, like, people's emotions around very silly things, 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 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. 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'll 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 specific set of problems.

[Brian]

Hire slow, fire fast.

[Kareem]

Yeah, hire slow, fire fast.

[Brian]

You don't believe in that. You obviously don't. You just said the fire.

[Kareem]

Yeah, yeah, yeah. I also think, I 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]

What other CEOism do you think are stupid a lot?

[Kareem]

Like, I think driving people really hard without paying attention to like, for example. I'll give you one example. People come in and they're like, AI is going to create a ton of productivity. We should lay out fire 20% 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 management, it's like the principal agent, problem management versus workers, where you're like, why aren't people thinking correctly? Why aren't they 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 rather my definition of fun is very broad, obviously. So type two fun is fun. For me, climbing something is fun. But I think motivating people through either just greed or fear or discipline

[Brian]

is

[Kareem]

not always the optimal. You need the whole toolkit. So like, another word for discipline could

[Brian]

be the fear and greed thing. Those are the.

[Kareem]

Those are all levers, by the way. Yes.

[Brian]

How do you think about that?

[Kareem]

I believe in the full spectrum of the thing. So it's like devotion is as good as discipline. 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. 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, 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.

[Brian]

I had Jack Dorsey on a few weeks ago. You two rhyme. He's an original thinker. He's not Central casting for CEOs. He's laid off a big chunk of his employees. But I think he's really retooled the way the company works. He's put AI in the center and he's delegating a lot of decisions to the center, the people around the outside. He's rethought his org chart, compensation. He's sort of reimagining it. I assume you're following some of that. What's your take?

[Kareem]

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 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 principle 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]

I don't think he was covering it up.

[Kareem]

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.

[Brian]

I think he's actually doing the thing.

[Kareem]

Yeah. And I think that's probably right.

[Brian]

And do you think he's on the right track. 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 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]

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

[Brian]

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.

[Kareem]

I can't believe he told you that.

[Brian]

How does that apply to being a CEO?

[Kareem]

That was an off the cuff comment. But if I remember correctly, I have a Q and a. 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]

Yeah.

[Kareem]

You know, so one of the things.

[Brian]

Calling them out.

[Kareem]

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. How does that manifest? What do we want? What behavior do we want?

[Brian]

Yep.

[Kareem]

And I think a lot of the times.

[Brian]

So you're calling the elephant in the room out. What about the elephant?

[Kareem]

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]

What do you want to do when you're old and gray like me? What's next for you?

[Kareem]

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, like, generative ambient music. I've been doing a bunch of stuff like that already.

[Brian]

Okay.

[Kareem]

I don't know. There's something around, like, creating soundscapes and getting into, like, 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 it. You're expanding kind of, like, your sound vocabulary.

[Brian]

Okay.

[Kareem]

Yeah.

[Brian]

I appreciate your coming on. It's a wonderful conversation. Congrats on all your success.

[Kareem]

Thank you. Thank you.

[Brian]

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. 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. I think it goes, be yourself. Everyone else has taken. I think it was Oscar Wilde who said it. I leave that with you. I hope you can be yourself because everyone else has 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 tend 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 are we lit? 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. 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. Hope you liked it. I really enjoyed him. See you next.