Invest Like the Best with Patrick O'Shaughnessy - Kareem Amin - The Unusual Approach to Company Building - [Invest Like the Best, EP.478]

Episode Date: June 16, 2026

My guest today is Kareem Amin, co-founder and CEO of Clay. Clay has become one of the fastest-growing software companies of the last few years, valued at over four billion dollars. It helps companies find their best customers and reach them at scale. But this conversation is about a lot more than Clay. Kareem is one of the most original thinkers I know.  We talk about the statues he keeps at the center of how he runs Clay — truth, justice, and courage — and what those words demand of him in practice. We talk about risk, ambition, and what he learned about both on a ten-day silent meditation retreat.  I've had a lot of conversations with Kareem over the years. This is one I'll remember. Please enjoy this unique conversation with Kareem Amin. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠.  ----- WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like The Best (00:02:29) Kareem Amin (00:03:07) Clay's Origin (00:10:50) Truth, Courage and Justice (00:16:09) Adulation (00:18:28) Risk, Courage & Self-Respect (00:21:14) Jony Ive & Steve Jobs (00:21:42) Role of Introspection (00:23:08) Lack to Wholeness (00:27:27) The Day Five Insight (00:29:57) Running a Startup Unusually (00:34:41) Learning from Magicians (00:36:27) Music's Role in Your Life (00:39:38) Making People Feel Something New (00:41:20) Vision in Company Building (00:44:29) Wealth & What It's Taught You (00:47:40) All Problems Are Communication Problems (00:52:14) Death Doula & Scaling (00:55:06) The Kindest Thing

I know firsthand how complex the tech stack is for asset managers. And seemingly every new tool and data source makes the problem even worse, adding more complexity, more headcount, and more risk. Ridgeline offers a better way forward, one unified platform that automates away all that complexity across portfolio accounting, reconciliation, reporting, trading, compliance, and more. All at scale. Ridgeline is revolutionizing investment management, helping ambitious firm scale faster, operate smarter, and stay ahead of the curve. See what Ridgeline can unlock for your firm. Schedule a demo at Ridgeline. Apps.com. Open AI, cursor, anthropic, perplexity, and Versel all have something in common. They all

use WorkOS. And here's why. To achieve enterprise adoption at scale, you have to deliver on core capabilities like SSO, Skim, Rback, and Audit logs. That's where WorkOS comes in. Instead of spending months building these mission critical capabilities yourself, you can just use WorkOS APIs to gain all of them on Day Zero. That's why so many of the top AI teams you hear about already run on WorkOS. WorkOS is the fastest way to become enterprise ready and stay focused on what matters most, your product. Visit workOS.com to get started. Felix by Rogo is a personal finance agent that turns a single prompt into finished client ready work using your firm's own templates, context, and standards. Send Felix an email like, take these comments and turn them for me, or update my

tracker with the context of these emails, or run the ability to pay math on this buyer, and Felix sends back finished PowerPoint decks, Excel models, and sourced research. Felix works the way your team already does, delivering work quickly and accurately around the clock. Learn more at rogo.a.ai slash Felix. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people-shaping business and investing. You can find Colossus, along with all of our podcasts at colossus.com.

Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Some may maintain positions in the securities discussed in this podcast. To learn more, visit PSUM. My guest today is Karim Amin, co-founder and CEO of Clay. Clay has become one of the fastest growing software companies of the last few years, valued at over $4 billion.

It helps companies find their customers and reach them at scale. But this conversation is about a lot more than Clay. Karim is one of the most original founders and thinkers that I've met recently. We talk about the statues he keeps at the center of how he runs Clay, truth, justice, and courage, and what those words demand of him in practice. We talk about risk, ambition, and what he's learned about both. I've had a lot of conversations with Karim over the years, and this is one that I'll remember. Please enjoy this great conversation with Karim Amin.

Can you describe the long-stranged journey you've been on, why you started, and then what it was like to exist and have done some interesting stuff when this thing happened and then how you took advantage of it? I find the two-chapter stories so interesting. We started with the really abstract ambition of how do we give the power of programming, to more people. My co-founder, Nicola and I, we worked in product, even though we both studied engineering. I think it was really just, hey, you're in the 21st century. You have computers that can do things for you, and if you can't tell them what to do, then you can't capture any of the value that's being created. We had a lot of ideas, and we wanted to build them, and every time we tried to build something, it was taking so long. I was also starting to play around with producing music, and I really like

tools like Ableton Live. I have an idea. I can extract it from my mind. and into the machine. And we were also in this kick of like looking at the history of computation, things like in the 1960s, the mother of all demos, just seeing the fluidity of the interaction between you and a computer needs to be super fluid for it actually to lead you to the next stage of thinking. You need low latency between. I have an idea it happened. And because we were coding, we felt that adrenaline that everybody's feeling right now, which is, hey, I can tell the machine to do something and it does. In the 21st century, the material, is computation. If in the past it was oil or steel or whatever it is, today it's computation. So the more

we can give that to more people, the more interesting things happen, the more egalitarian it is. It's kind of interesting because that was our desire and there were no LLMs, which we started off by thinking about the terminal and we're like, how do we reinvent the terminal where engineers are spending all of their time? And then we're like, well, that's just going to speed up engineers. We need to find something that gives that power to more people. In 2017, we started thinking, do we give it to engineers or non-engineers? Do we give it to consumers or business users? We ended up deciding business users for a variety of reasons.

Within that, we're like, okay, which department in a business actually has a ton of ideas but isn't able to execute them and landed on sales and marketing where we think people are really creative, but they don't have the ability to turn a lot of their ideas into reality. I'll give you one example that's real today that is kind of, wild, but we have one company that sells to businesses that have a lot of garbage. So now they're using Google, what's called satellite view, to see which areas have a lot of accumulation of garbage, and then they figure out, okay, that's a good business to sell to. That's an idea that you might have, but it might be super hard to execute that at scale. And now something like Clay can

actually translate that for you. Because of that, because of the whole intention around Clay was how do we give the power of programming to people? That's kind of how the name came, because we're like, okay, it's go-to-market, but now you're an engineer. We came up with that before it was really possible to use LLMs to fully code, but it was how do you systematically think about a problem and break it down and then execute it? We've also kept that ethos in the company. That's what makes us really different than everybody else in our space. There are simple things that we've been saying out loud, but I think people don't really believe

that that's why it works. So one is it's a creative task. So if it's a creative task, we need to leave it somewhat open-ended. A lot of companies that counterposition to Clay or in the space are like, hey, what you really want is salespeople are, people have literally used the word coin operated. So what you need is something that's super easy to use. It gives you the answer. It tells you who you're selling to and what you're saying, and it just works.

Whereas we think you always need in sales to find go-to-market. Alpha. How are you different than everybody else? Otherwise, it's just noise. In order to do that, you need to have a really powerful tool that allows you to experiment quickly and try things out and see what works. So we built that instead, which was very counterintuitive. Describe the take off of chapter two of now LLN's come out, what that moment felt like, what the subchapters have been since. Yeah. What's interesting in that story that is maybe worth talking a bit more about is that This was back in 2022. We had made a decision to say, okay, we are targeting go-to-market teams, specifically sales.

Specifically, we're going to start with outbound. Specifically, we're going to start with people who want to get data from lots of different data providers in order to do outbound. In fact, it's going to be agencies and not startups. And we're going to do a lot of what we're doing and support them in public and build a community. So we took a lot of decisions that I think were not. obvious. The main thing that happened was really the courage and commitment, I think, to making those decisions that actually allowed the company to take off. Because the company was already taking off before ChatGPT came out. We were well set up to include LLMs in Clay because, one,

we were set up to allow any integration to anything. And two, we were a coding-like product just designed with go-to-market primitives. As soon as we had LMs, it just boosted everything. So for Clay, there were three core assumptions that we made. And I actually think this is how to build a really big company and one that grows really quickly. So we went from one to 100 in two years, but that wouldn't work if we weren't pointing in the right direction.

So you need to kind of set everything up so that you're pointing in the right direction so that when the wave comes, you go with it and you're not fighting it. For us, we made a couple of decisions, One, people in go-to-market are creative, and so we're going to give them the most powerful tool. If you were going to give the most powerful tool instead of the simple out-of-the-box tool, then you need to find the right customer or user for it. For that, we said, okay, we're doing it for RevOps, which is an existing kind of role.

And we're going to call the subset or the word jobs to be done go-to-market engineering, to give it a framing. This is the tasks to be done, are all the things that you need to do, the activities to grow, your business, remove any obstacles to growth. The last part was we're going to charge for usage instead of proceed because we're trying to get more productivity. So if you have fewer people, we didn't want that to be something that is an anti-incentive for us. If you just look at those three decisions, almost every other decision in the company falls immediately out of those. Anyone can come up with what we should do next if you believe these three things. That's the best way

also to run a company that's growing really quickly because I have to just communicate to you these are the three things that we're assuming and whenever you're making a decision, check to see if it works within these three concepts. I feel like people don't talk enough about the things that actually matter in building a business. I had this dream actually where

it was kind of like a vision where I saw lots of statues in a modern city, but I was wondering like, oh, we don't build statues anymore. But I'm like, if you look at old republics, they would have statues for concepts like courage or integrity or justice. And there are like gods for these different things. And I feel like we've forgotten these abstract kind of ideas that matter in the moment when you're building a company.

It was actually, hey, you need courage to make a leap and commit to these ideas. and then see what is the logical conclusion if we take these ideas seriously all the way to the end. If you could put three statues off the elevator in the lobby, what three would you build? Courage, truth, and justice are the ones that come to mind.

Say like one click more about each, why those, sir? I think courage because one thing that I think a lot about is I think capitalism rewards risk more than anything else. I think a lot of people think it's like meritocracy

or hard work, which I think is silly. there are a lot of people working really hard and not making a lot of money. So it's not hard work. There's some correlation there, but it's definitely not just that. It doesn't just reward skill. There's a lot of really skilled people. There are people who do things that I can't even dream of. You're eating a sword or you're like juggling and they're not making as much money as someone doing a YouTube video.

It's clear again that that's not the case. I do think it rewards risk. which makes sense. I don't have like a strong comment on whether that's good or bad. I'm just trying to figure out what's actually happening. There's a lot of people

who think they're taking risks but aren't taking real risks. I talked to one founder who went to a good school, then went to YC, and then was telling me about his company and he's like, we serve sales and we serve recruiting.

And I was like, you have to pick one. This is where you're actually providing value. In picking, committing yourself to serve some group of people in some specific way. For me, at least my definition of risk or how I've experienced it is you need to not know what's going to happen genuinely.

You're going to discover something new. I think it needs to be coupled with a high potential for shame. It needs to be you can fail in a way that feels scary or maybe associated with shame. And when you're doing that, you're genuinely about to discover something new and learn from it.

And that's when you can take it. real risk. And to do that, you then need to have many traits. One of them is courage. It's amazing. How about truth and justice? Let's take justice for a second. I want to live in a stable society that allows me to kind of like have the time and space to think of things. I think the world is pretty crazy. I went to see this movie called Stop Making Sense. I was downstairs in the movie theater. I had a joint that I was about to smoke and I was trying to light it up, but I didn't have a lighter. I asked a guy who was standing there. I was like, hey, can I borrow your lighter? And he was like, sure, can I ask you a question? And I was like, yeah, of course. And he was

like, what is this? And I was like, what do you mean this whole thing? He was like, yeah, what is this? And I was like, well, that's a big question. I think, like, the world is a mysterious and amazing place and I feel like there's so much to know. We're just starting to make progress on how wonderfully weird it is. And we should be spending more time like exploring that. And to do that, I feel like we need stability. So to get stability, I think you need to have justice between people. I think there's no stable way for some group of people to dominate others. It just doesn't work. No matter how, strong you think you are, the other person is a tremendous nuisance if they feel like they're treated unfairly. So there's no stable configuration around that. And if you're thinking about the economy

or like countries, you can't bluster your way out of it. You can't say we're the strongest. Even when I'm saying that, I have to remember when I have power over people, you tend to be like, they must do what I want because I want them to because I control this. It's just not a stable configuration. You can get by for a little bit and then you get tremendous pushback. So I think that having the value of justice, one thing I think about is like how do you treat people with respect and fairness all the time in every situation, whether you're hiring them or firing them or you're disagreeing over what they should be doing? So I think that that maybe is low it's fueling this democratization. even people are stable in a place where they feel like they have the opportunity to get what you've gotten to

as long as there's some fair chance for that. And they're okay with what they've gotten if they feel like, hey, this is what's available to me at the moment. This is just kind of like an internal thing that I've had. I used to play soccer. Even on my team, if I feel like we fouled the other team and we could get away with it, I would have like a really weird thing of integrity. This feels off. Do you have a sense of where that came from?

nature, nurture. It feels like it's some intuitive knowing for myself that I'm a long-term greedy person. One of the things we talk a lot about to the company is like, how do you be long-term greedy? And I think the only way to be long-term greedy is to stay in integrity for people to feel like there's justice all the way along. I think it's also just like a belief in yourself. You don't have to cheat in the short term to get something. You're going to win. Let's say you're playing a soccer game. you feel like you cheated or like this wasn't fair and then you won. It doesn't feel as good. I did hear your interview with Brian to ask you the statement he made around getting to $100 billion and...

People are my shit. Yeah. I actually felt like I related and we're obviously in a much smaller spot. But even early on when we raised our Series A, I remember having that sensation of, If you're doing this to get adulation or to get prestige or to make some money, there's no end to that. It's kind of like an empty thing that passes. The only judge of anything is yourself and your own self-respect. You have to be doing it so that you feel like what you've done is interesting and worthwhile. When you're an ambitious person, your judgment is actually way higher than anyone else because you know everything that you're thinking and you know everything that you've done. So I know everything that I'm thinking about or doing, and my standards are higher than anyone else.

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It's like a cleansing function or something. Like whatever lasts in my brain through that hour like I want to write down. When we last word together, this is the one thing I wrote down, which was this notion of optimizing for self-respect over everything else as like the North Star for behaving. I'm curious how that relates back to risk and courage. Do you think those things are related? Do you think it's possible to help people become more courageous and take more risk? For sure. I think in order to do that, you just need to understand your mind and your motivations more and be more honest about them. So again, back to the saying simple things honestly,

it's very hard to admit to yourself, I think, why you're doing something. Even if you look at the narratives for companies, none of them have any relation to the motivation of the founders, and we don't talk about that in public. For me, for example, it's like, why am I building a company? Do I think that I will be more liked or loved if I do something that is a success, a world-class level? Can I get that now? I've had friends come up to me that are like, hey, I don't care if you succeed or fail. I love you.

And I was like, wow, that's actually helpful. I didn't think it would be, but it's feeding. Some part of my desire must be fueled by that, but I can get that right now. And now I can start to take real risks where I'm thinking about the business and not trying to fill this particular need. VCs have this common trope that is, hey, we invest in someone that has a chip on their shoulder or has some kind of lack that they're trying to fulfill. And this is common across creative work.

The trope is like you're depressed or you're anxious or whatever, and you're trying to fill that, and you're actually afraid to lose that depression or anxiety or whatever it is because you feel like you'll be less productive or creative. Through my journey, I had this moment where I was like, you know what, I'm not going to create from a place of lack anymore. And I went around probably pretty annoyingly telling people, I have everything I need.

I'm good. Post-black. Post-slack, yeah. It's a great negotiation leverage because there's nothing you can give me. I feel great. I'm already complete. From there, you can still create.

I think people are misunderstanding, tremendously misunderstanding this, in my opinion. If we were in a post-scarcity world, no one will do anything. Everybody will just be hanging out. And I was like, have you been to Burning Man? People are still doing stuff, and they have things.

You can create from a place of wholeness, and in fact, you will be less destructive in the world. I think you'll create less damage. We keep thinking here like, hey, let's think of our customers. What are we trying to give them? Why do people keep saying customers first? It's because when you're in a company, things start to happen where it's like this person's thinking about their career or this person wants to please this other person.

They're not thinking about the customer. They're just thinking about the internal dynamics. The more hole you can be, I think, the more risks you can take and the more courage you will have because you have nothing to lose. It's funny to me that perhaps the most interesting duo in modern business history, Johnny Ive and Steve Jobs, were like almost undoubtedly creating from this generative place. I don't know if they've used the same terminology or something, but you read it all. Like it's all there. They're the most adored, but maybe the least emulated. It demands the question the things that got you to this sense of wholeness from this place of lack. There's been much strange debate about the role of introspection in business and in general. Naively, I would say, say it's introspection, it's a key tool in the toolkit to get from one to the other. Curious what your experience has been or what you would offer about that. I kind of understand the motivation here because one thing I talk a lot about here and have

thought for myself is the amount of work that doing versus meta-analysis can sometimes flip. So you should be like 90% of the time doing and then 10% of the time meta-analysing. At work, we've had this happen a lot and I talk to the team a lot about it where people are like, hey, what is going to happen in one year? Why are we building this feature instead of that feature? And I'm like, is that stopping you from taking the next step in your job? If not, then you're procrastinating. My sense is his conversation around that. I think his example was Walmart. If you're trying to build more Walmarts, yes, you should always be thinking about, wake up in the morning, build more Walmarts. But at some scale, when Walmart is affecting all of us, if you don't think

about why you're building Walmart or what more Walmarts do to us or to a shared environment, that responsibility is on you. I think that the more you make and the more successful you become, it is part of your responsibility back to all of us to think about what you're doing, that you're our representative now. You're not a completely independent actor. And in fact, we have the power to pull some of that stuff back from you. So is there anything that you did in particular, going from kind of lack to wholeness. For me, I think the introspection is, it was a journey to kind of understand, like, why ambition? So I was suspicious of my own ambition. I was like, what am I trying to get out of this? Part of why the company took some time

to take off was because I was grappling with that. And that led me to investigate which parts of me are trying to kind of be expressed through this. And that was just my own personal interest. I just found that I couldn't just do something without understanding my motivation for it. Because I was looking at people who are further ahead in my field. If you're a great business person or you built a great company, I was like, do I want that? I think it's also coming from like valuing my time and myself. I was having this experience where I'm like, what if I took myself really seriously? You could take yourself lightly and just be like, well, these are just thoughts.

I want to do something big. So do other people? Or take it really seriously and be like, why do I want to do that? What would I actually offer the world if I was able to do that? And then thinking like, hey, you can succeed and create a lot of damage in the world. I think a lot about death when you're deathbed. Like, what are you thinking? How does it feel in that moment, if you had a moment to reflect, how do you judge yourself?

And there's like the experience of every day and living a life that you feel is worthwhile on a day-to-day basis. And there's also like, how did you impact the world if you did impact it? And I wanted to make sure that I felt like I really grappled with that correctly. And I didn't just try to accumulate resources and just be like, hey, I did something big. I accumulated some resources. It does go back to this like justice principle. It's like if you're going to do something big, you need to kind of think about the consequences of you taking that role because it's just the role. It's a really cool thought exercise to say, okay, play out the thing I'm doing to its natural extreme.

Do I want that state? No one does that. I had one time where I remember when I was much younger, I was like, oh, like, I want to make a lot of money and then I'll be a philanthropist. And I'm like, is that actually useful? There are a lot of philanthropists. Is it working? Are they actually impacting the world? Could we move faster in some other kind of formula or like setup? Or is it just that I want the control to pick the causes that I want? Maybe one more thing on the death thing that I think is kind of interesting was like my own insight that I had. I went on this 10-day silent retreat a while back. I thought I was going to just go think it was not that. It was kind of like a spiritual experience. It was called Herodaya, not like a Vapasna.

Their approach, there is like a non-dual approach to meditation where typically you kind of like meditate on your breath or some object. Whereas in non-dual traditions, it's called the direct path. And in the direct path, you meditate on the space between the breaths or you ask the question, who am I? A very frustrating question. I would say I would not recommend. But anyway, I'm doing this thing.

On the fifth day, I have like this big insight where I'm like, I figured it out. I got it. Then on the seventh day, I'm like, okay, well, what now? I start imagining going back and telling my friends about this insight, but I'm like, oh, I'm not here. I'm just imagining the future. I kept wanting to go towards the end. And then I had this big flash of insight that I try to remember.

but it said whenever you're picturing the future or anticipating the future, it's kind of like Freud's death drive. The only thing that happens in the future is you die, the far future, whatever it is. And so you're accelerating that. And as soon as I had that thought, it's kind of the death drive.

Thinking about the future is the death drive. And so I immediately felt back in my own body in the moment and felt the boredom of where I was. And I was like, wow, this is such delicious boredom. I finally got that insight, which is I'm so grateful to be bored right now because it's so amazing. I also realized that I have this scarcity, like food scarcity. I was thinking constantly about food and where am I going to eat. And then I just had this one P and it exploded in my head.

I was like, this is too much. I can't. But I realized that I have an accumulation tendency where I'm like, where's the food going to come from? And in the company, I noticed I'm like, where's the next ARR going to come from? Now I'm aware of that and I'm like aware of when I have enough. and then I can take more risk. I don't need to accumulate something that's way beyond actually what we need.

What was the day five insight, or was that the insight itself? It's hard to describe because it's an experiential thing. I think it was a momentary experience of like this understanding what matters or something like that because I felt like,

oh, I'm connected to all things. Really bizarrely just feeling like, hey, I am a component or like a part of this whole thing and I'm connected to all things and they all matter. I had kind of this thought of, one, I'm no better and no worse than anyone else.

But also, it made me feel like this real empathy when I see someone who's suffering. I'm just like, oh, they're also me. Not I empathize with them as if I was them. I'm like, this is actually me. That's kind of like a really out there thought or a belief. Strange thing is it's actually not at all. Like it's like the longest lasting set of beliefs in the deepest, richest, philosophical traditions.

Yeah. Today it's still. This is abstract idea today. Yeah. It's still like niche. It used to be kind of like a common thing supported with religion. But to me, what was crazy wasn't the idea. It was the experience of really feeling that.

And then knowing that when I hear something in Buddhism, there's just freedom of all beings or knowing that the suffering of one person is the suffering of everyone. So back to the justice thing. Well, I can't solve everybody's problems. And in fact, that would be hurting me to try to help someone when I don't have capacity. But to really know every single person, they're carrying it for me rather than they fucked up or they screwed up. And I'm better because I worked hard and did X, Y, and Z. Just to bring it back to our statutes, is that then truth, the day five insight?

Is that just truth? Yeah. if we go back to capital T truth, it's understanding that. And then I understand why in philosophical traditions, or even in religions, they're like remembrance. I can get that momentary understanding, but then remembering it in the moment when I'm making a decision about my business or about like my personal life is very tricky. But I do think that that is what's necessary for us to get to the next stage of what's

interesting in the world. There's so many mysteries, so many interesting things. and I feel probably like many other people that were squabbling in circular ways around the same nonsense. My real anger is like, what are we doing? We're wasting our human potential, wasting our time.

If I hear and digest all of that and then I imagine, okay, this guy is now running a software startup. I might imagine that that startup is run in some unusual ways. So I'm curious what those are and why you arrive at unusual ways of running the business. Yes, there are some unusual ways of running the business.

Yes, there are some unusual ways in which we run the business, but also I think it's important to be careful of how much you push ideas onto other people or project onto them your beliefs and also to remember what context you're working on. It's almost like telling a story. If this is the normal way to run a business and then you think that it's this completely bizarre way over here, you also need to take the steps to tell the story. And I think it's a normal way. And I think it's It's the same in like product development. I can't just give you a product that you have no context for.

You don't even understand how to interact with it. It's like, hey, these are my personal beliefs and my interest that are underlying some of the normal activities that we do. And then there's adjustments that we make. I'd say the first and most important way is that it's a felt experience in the company of how we treat people and how we think about their personal development. but there are concrete ways in which it shows up. One way is that we over-invest in things that people typically under-invest in. We've over-invested in recruiting, in brand,

in content, in community building. We've hired people who are very overqualified in some of these roles who are doing it for the first time. For example, we published an article about this with one person who was an early employee, Mishdi. She took a content role. She would have never taken a content role.

it's typically kind of not the most highly paid thing in a company or it's extra and we compensated her like a PM and we're like go do it so we take those kinds of risks and then we stick with it I think another thing by the way with risks is when you couple risks and courage the next part is commitment you actually need to kind of follow through to see what actually ends up happening you can't just quit in the beginning we take that seriously and if we see somebody is really skilled or has some star potential, we stay with it for way longer than most. Everybody talks about hiring fast and firing fast.

We've had people who nine months in were floundering. And we're like, this person is excellent. I know they are. But what's going on here? Is it the role? Is it the context? Is it our decision making that's limiting them? Eventually, we find an amazing spot for that person

and they become a superstar 50% of the time. The other 50% of the time, this person might be really special, but we just can't create the conditions for them or they're too far away. One thing that I've talked to my co-founder, Varunat is like, we're never pissed off when someone doesn't work out. We're like, hey, you're just, we're here and you're here, maybe along the journey one day you'll get there, but you're not getting there fast enough.

You don't have what we need at this moment. So I don't even have an opinion on whether you're good or bad. People are like, this person was good, this person was bad. Were you good in the moment that we needed you to be? You might also be super skilled, but you just didn't perform here. I've had people who are incredible. I know they're incredible, and they couldn't perform here for a variety of reasons. And they've gone to other places and done a really good job.

So I think it's important to be nuanced. There are some other things where I think some of the things that people have covered about us in the past is. I like clowning, for example. I discovered clowning. So it's clowning. Exactly. I think I was an SF at a party, and someone was telling me that they were going to go to this clowning workshop. And I was like, what is that?

I think of it as like edgy improv. There's kind of like four types of clowning, physical clowning, which is the one you would imagine when you think of clowning. There is emotional range. Let me make you happy, that make you sad, then make you happy so you can feel the full range. There's the jester, which is like telling truth to power. Then there's the trickster, which I think is pretty interesting, which is how do I tell you like spiritual truths through jokes? You realize, hey, everything does change. That's like a truth about the world, but I get you to experience that.

We are really into magicians at Clay. We incorporate it into our events or things that we do, and we take risks. Our brand takes a lot of risks. Way more risks than, I think, general B2B brands, and that's why people love the brand and the company. It's authentic to us, but it's also honest. It's trying to really cut through and be like, hey, we think you'll be interested in this and we're not hedging.

I think a lot of times people are authentic but hedging. So they're not really saying what they want to say because they're afraid of the consequences. Or if you weren't from magicians. I actually think the trickster thing is the thing that's been a common thread between us. There's this place called 69 Atlantic that we had been going to like,

it's a small speakeasy magic, close-up magic. There was like 23 spaces in the back of this bookstore. and they get like world-class magicians every month. And the thing that I remember from these really incredible magicians is it's not just a slate of hand thing. There's a storytelling component. It's kind of wild. A lot of them are telling a story of like a deep understanding

of how your mind works or how the world works where they're like, hey, I'm showing you this thing and really what they're trying to do is to spark curiosity. We're going to do something about this at Clay. We're calling it re-enchanting the world. In a world where there is AI, it's literally magic in some form. And to remember that this is magic, a lot of these things that we're sitting in front of are still magic. It's pretty wild.

And to re-enchant the world again and not make it like this boring place where you think you understand how it works, because you really don't. So I think they're doing simple things to reignite that feeling of wonder. And I think if you take that feeling of wonder actually in your everyday, life, you're a more friendly person because you're not like, oh, I understand how this person works, or I understand how this is, you're like more curious. It makes you more curious about our customers and makes us interact in a more pleasant way because we're like, oh, there's stuff to learn here. I think what I've been actually getting from this magic stuff is been like remembering what it feels like to be like, I have no idea how it's working. I can't even begin to comprehend how to think about it.

I know that it's a trick, but I can't figure it out. For whatever reason, this makes me wonder the same question about music, the role that music plays and has played in your life? And what you've learned from your many, many experiences with music? Well, I'm a dilettante musician, but I actually just started a band. I was talking to another famous musician who was calling me because he's starting a company,

and I'm like, wow, I'm going the opposite direction, man. But I was reading this piece that was super interesting for me. And one of the key things I think with music versus other things is time. You can't listen to a song without time. time is actually a core component and silence as a core component like the spaces between things so it's a good reminder that those are like

fundamental things that you have to work with it's like very zen where the room isn't is where we are if this room was full of things we couldn't sit in here and we only think about making things we don't think about removing things and we don't think about things unfolding I think video is also like that

but a painting isn't you can see it all at once so I think about narrative how are you telling the story how are you bringing people along with you on the journey? You can't tell everyone everything all at once. It's overwhelming because you've had time to process. They haven't. This piece that I was reading, it was talking about endings.

We always think about beginnings, but we don't really think about endings. When you're starting a company or not, well, what about all the people that I'm going to fire it? And so many crazy things genuinely happen. As soon as you have a large number of people, you're dealing with a microcosm of humanity. You're running like a mini-society. So it was like, hey, we can look to music to think about the different forms of endings and learn from that.

Some songs end as just like repeating and it goes down in volume. Some things end suddenly. It's like a whimper or intensity. You can think of these as different ways to end something. Another one that I think is really cool. This was an essay that I read that was called The Emancipation of Dissinence, which first of all is a really cool title. But it was theorizing the history of music as a history of accepting more sounds as music. So in the beginning it was just maybe drumming.

First it's like the tonic. You play the C and then the C an octave above. And then it was adding the fifth. That's why it's called the perfect fifth. a lot of Baroque music had that. And then people started adding the third, which is what creates chords, minor and major chords. And initially that was resisted.

People were like, what the hell is this? This feels off. But then you add the seventh where you get jazz. And people were like, that's unacceptable. Like this is not music. And then eventually you start to add more and more tones. So this was arguing for, in Western music, there's 12 notes. But in Arabic music or Indian, there's 24.

And there's other scales that you can use that have even more tones. you can use microtones. Now that you have electronic music, you can make any kind of sound. I think this idea of accepting more sounds as music is actually a helpful product principle, just a way of being where you can start to think, what are all these other ways of being that you think are off

that actually could be productive or useful if you put them in the right context? It seems also like an interesting throughline is in the world we're going into how important it will be to make people feel something, but maybe also something new. If we can create anything, the logos of it all is,

yeah, whatever, you can create anything you want, that the pathos becomes really important on top of that. Insights for music is like, make people feel something new. We use this a lot, bring it back, I guess, to the business. I'm telling people like,

hey, we're not building a microwave. Microwaves are useful, but they're commoditized. You just go and say, hey, one minute, heat it. It does what it needs to do. There's no difference between most of them. But we're building a, guitar. With a guitar, there's just six strings and 12 frets, but you could spend your whole life

just getting better at that, and you can only be playing one style of music, and it's still like new. If you bring that to sales or go-to-market things, it can feel like a crazy stretch. If you actually respect that discipline and be like, hey, what is the ultimate version of sales? Marketing or customer success, that's why it's called go-to-market, in my opinion, is just like, how do I take the thing that I made and give it to you when you need it. If I really truly was like, hey, what's the idealized form of this? That's what it is. It's raining. I bring an umbrella. You were like, great. Thank you. That's what you actually want to get to. And I think there's a place where I made something, especially as people make so many new things and you happen to need it and it's very niche.

And I'm able to find you and give it to you without necessarily manufacturing that desire in you. Ideally, if you need something, we can get it for you because we happen to be making it. We're thinking about all of the creative ways to figure that out. One really interesting conversation you and I've had before is about the role of vision in company building and the leader's responsibility or lack thereof to have one in the first place or to have one sometimes. I'd love you to riff on the leader's role and responsibility to have or not have a vision. I think when we were having that discussion too, my instinct is to go one level deeper, or at least that's how it's coming up in me. Let's turn it back to one of our statues, truth. You need to say the truth. So if you don't

have a vision, then you don't have a vision. If you do have a vision, then you do have a vision. I think it's important to not say something that actually isn't happening. That's my answer to that, is that I do think ultimately you need to have some guiding principle or some compass, but you don't need that at all times and you don't need to force it. If you just know what the next step is, you should take the next step. And sometimes things happen in all kinds of ways. Most of medical discoveries are complete coincidences. So many of the most advanced things, the cosmic microwave background, complete coincidence. You couldn't have gone out and said, I want to discover the cosmic microwave background. There's so many of these things. And so I think we're telling ourselves

a story that is not true about the nature of discovery and how it happens. And, And I think we do a disservice to everybody when we go back and retell the story in a way that is not honest because it confuses the people who are on the path of figuring it out. So for me, a much more honest version, let's say you're starting a company and you don't know what to do. So many people have that problem. You're like, okay, I want to start a company. I don't even know why I want to start a company, but I feel like this is what I want to do. You don't need to have a reason. And then you can go and start doing things.

And once you find something, you can be like, okay, and this is interesting to me now. All the stories of greatness are like, I was 13 and I saw this one thing and then I dedicated my whole life to it. And I think that happens and it also happens in other ways. Optimized for discovery rather than destination would be like one way to think about it. Leave the space for the opportunity to discover. If you do have a vision, you should be clear about that and clear how confident you are in that. And if you don't have a vision, I don't think that's a problem. I think you can take the next step and allow the vision to come.

In Native American traditions, there are things called vision quests where you go and fast for a few days and you're asking for a vision. Sometimes you need to do things in order to get the vision of what you're supposed to do. And by the way, in companies, it also could change over time. So you might have a vision and then either the vision is wrong or a lot of companies who started five, six years ago that are confused now because things have changed. Well, it's time to change the vision. and you don't need to settle on a new one immediately. You can say, hey, we don't know what we're doing right now, and we can take the immediate next step in what we're doing right now

and wait to receive that vision. Do you feel like you have a vision right now? Yeah. Right now I feel pretty clear, and within the scope of what we're doing, what the vision is. We're helping every company in the world find who their best customer is and find more of them and accelerate that. What about the notion of wealth?

You've also in these two chapters had this interesting, experience of now because of Clay's success, you've achieved a level of wealth that by any measure is extraordinary. What has that process been like and what has it taught you? That's a very taboo topic. I know. That's why it's interesting. My experience is the initial thing that I had thought is true is that if you're not feeling whole in yourself, there's no amount of wealth that fills that. It doesn't change that because it's a continuous competitive game. It's a loop. I was telling someone, if you want to raise $100 million, you need to first feel like you don't need that. Paradoxically, also that you already have that.

In order to raise money, you need to be like, I have $100 million in my bank account. How does that feel? Act accordingly. Because you need to act like you don't need it and you have the confidence. Maybe my own core wounding is I have this super heightened self-reliance where I feel like I don't need other people and I can do everything my which is partially why I think it's helpful to be an entrepreneur. And what I've been doing is dialing that down to be like, no, I'm interconnected with people. I do need people. In fact, I need help. I need support. I also rely on so many things. But I think what material abundance gives you is

the reality also of your time back. And I'm choosing, for example, to build this company. I don't have to. I don't need anything. I don't need it to succeed more. I don't need to make more money or whatever it is, I'm choosing what I want to be doing with my time. And that goes back to that kind of that truth part that's really empowering. I can make my own choices and I can test things out in the world and see if they work or not. I'm not scared or worried about what happens. But I also needed to have that point of view in order to get here. Having the opportunity to like choose what I do with my time and to like take bigger swings, that feels really important. And then it's like, what responsibility do I owe back to society?

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competitive edge. Visit ridgelineapps.com to see what they can unlock for your firm. You also want sent to be that all problems are communication problems. I'm curious how you've gotten better or what you've learned about not falling into that trap. It's not that all problems are communication problems. It's that we might have a disagreement or different needs, but often we can't resolve it because we're making assumptions about each other, we're doing all kinds of game theory things about what would happen if you did this, if I did that, rather than being able to explain clearly.

And even within that, I think it's kind of like in negotiations. You might have different strategies, but my strategy is to be as clear as possible about what I want, what I think you want, and then what the possible options, assuming that you are really intelligent, can read and have access to the same information as me. I need to know what you want and what are the options available. And then we might still disagree, but at least we are disagreeing from a place

of clarity rather than from a place of misunderstanding. That's very, very difficult to do. Let's say we're asking someone to leave clay, which I think is a difficult thing. You can do it in a way, I think that in most cases, as long as the person is in a shared reality with us, in a way that is based on clear communication. Do you think it's working here? I don't for these reasons. What do you think? And maybe you're like, no, it is working. And I was just like, okay, let's bridge the gap because we can get to a place where it's like, I don't want to be giving you negative feedback every single day. That's not fun for me. I can't imagine that it's fun for you. So then why do you want to be here? And here are the gaps between us. At one point, I told someone, hey, listen,

I've lost faith in the ability for you to bridge the gap. I'm the CEO, so it's not a good situation for you. It doesn't make sense. And even if you think you can get there, I'm taking responsibility for that. I'm not saying that this is rational even. It's just, I can't do it. And that's it. In that case, it doesn't really make sense for you to continue working here. And I want to share that with you because I want to be like direct and clear about it and also own up that this is my call. Like any relationship, there's no compulsion. A lot of people actually really appreciate that and are just like, okay, I get it. I wish that it. I wish that it, was different, but it's not, so I'm going to do something else. Most times, if someone's leaving,

what are they worried about? They're worried about what are you going to say in the future to other people. So I tell them, hey, if someone calls me up, I'm going to say, it didn't work in these ways, but I think these are their strength. Here are the gaps that we have in our organization that didn't support them. How do you not think about that? When I call up a reference is like, can you tell me what was wrong with your company at the time? Because it wasn't perfect. It's always about someone else. It's obviously not true. There are times when my management skills weren't there to handle this particular person or the company itself was not working.

And so it creates a really bad vibe for everybody inside. When things are working, things are working. When things are hard, only a few people can handle that. The reason I'm saying these things, by the way, is I'm like, these are the things that I think are actually interesting. Part of my experience of building a company was I just wanted to know through building it and being given the hard choices of how to relate to people or given a quick profit versus a long profit,

what would I do? And what's the experience that other people who are making these choices are facing? And I think we're not talking about these things because the risk is too high, right? Like if I talk about what I'm doing, and a company and how I'm treating people, maybe someone will sue you

or customers will lose faith in you. I really feel like companies are built through rules of thumb where I'm like, hey, how do you scale from 100 to 300? And then I talk to five people who've done it and they tell me. And by the way, I've done things that are completely the opposite of that. And it's worked. And the reality is back to the risk.

When you're going from 150, for example, to 300 people, you don't want to take the risk of doing something new. You're like, these people did it. But then you're going to get the same problems that they had. So many people told me there would be all these weird problems scaling 50 to 300 people. None of them happened. We have some other things that happened, but I didn't have the typical problems because I didn't do it the typical way.

As we approached the end, I have one more question about endings. I'm realizing I take a lot of notes after our various meetings over the years. The first time we met, the idea that I remember writing down was, you told me something like, you wish that there was something like a death dula for companies. And then earlier today, we were talking about this idea that scaling isn't just some universal good. So these are related in my mind. And I'd love you to end by just riffing on this death dula and scaling concept. I'm just like, why are we not talking about whether it is good to scale every business?

People talk about it a little bit in this like really boring, super worn out way of, should you raise VC capital or should you bootstrap, completely not interesting ways of talking about it, but it's like if you had a donut business, should you try to scale it? What does scaling it entail? What do you lose when you scale it? Should we be as a society incentivizing all? all businesses to scale. And we all know this problem, which is like, hey, this restaurant was really

good. Now it sucks. So because I think there's a life cycle to things and maybe part of this meditation retreats and thinking about the death thing, I've been thinking about like, is there a life cycle to companies and should we just be okay with that? I'll pick Microsoft for a second because I think it's an easy example, but hopefully they don't hate me for this. You have an initial, put a computer on every desk. I remember that mission. When I was a kid, you did put a computer on every desk. But now the mission is devices and services and do cool things. Once you achieve a mission, the idea of a company, I think, started in the 1500s.

I think it was the East India company or something. So you get together for a purpose and then you do it. And then should you disband or should you keep like the minimal number of people? I think the crypto people have had some of these ideas. Okay, you built the layer. Now you move on to the next layer. I do think it's worthwhile as all this disruption is happening to start thinking about the new ways of doing this. I'm curious about it. A death dula for companies is, hey, if your company has achieved its mission,

should we help it pass? Maybe it should have children and people come out and they do cool stuff, but maybe we can institutionalize these things rather than trying to scale things that become zombies or become worse versions of their former selves and then complain about it when we're incentivizing everybody to scale no matter what. I wake up every day, and I think, how do I make more clay? I literally think about it. It's consuming all of the CPU time in my brain. In my friend group, they're all thinking about this because I just keep talking to them about it. So if that's what's happening, should we set up some kind of structures to be like, well, what happens when you scale everywhere?

I don't just care about scaling. I care about how is this creating value in the world. People are talking about there's, I don't know, 1,500 unicorns. If some of them are zombies, how can we help them? Diet of nice stuff. You need some grieving. You need a possibility to move on. We don't have support for that for companies.

And I think it's because no one talks about endings. When you and I are together, I feel like we always talk a little bit about Clay and a lot a bit about even more interesting things. And Clay is very interesting. This has been yet another example of one of those conversations. I've loved having it. When I do these, I ask everyone the same traditional final question. What is the kindest thing that anyone's ever done for you?

The one that's coming to my mind immediately I had already mentioned, actually. but it's a few friends have come up to me before Clay succeeded and were like, hey, you don't need to do anything. We just love you anyway. And then I realized, I don't care what they're doing. I don't care what they achieve. I just implicitly like this person and love them. And knowing that I had that and then I could give that back to myself as well without any achievement, because I think my childhood wounding was feeling like, oh, I must achieve in order to have care and love. And I was like, I actually don't need that. It created a ton of clarity

where I was like, oh, I'm doing things because I want to, not because I need something from it. So I think Clay is just the output of a lot of thoughts and things, and we're doing it in a way, for me, I hope, where I'm not attached. I'm not attached because I don't need anything from it.

I wanted to evolve the way it wants to evolve. Take you so much for your time. Yeah, thank you, Pat. If you enjoyed this episode, visit colossus.com. find every episode of this podcast complete with hand-edited transcripts. You can also subscribe to Colossus, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at colossus.com slash subscribe.

You know how small advantages compound over time. That's true in investing and just as true in how you run your company. Your spending system is your capital allocation strategy. Ramp makes it smarter by default. Better data, better decisions, better economics, over. over time. See how at ramp.com slash invest. As your business grows, Vanta scales with you, automating compliance and giving you a single source of truth for security and risk. Learn more at vanta.com slash invest. Every investment firm is unique and generic AI doesn't understand your process. Rogo does. It's an AI platform built specifically for Wall Street, connected to your data, understanding your process and producing real outputs. Check them out at

rogo.a.i slash invest. The best AI and software companies from open AI to cursor to perplexity, use WorkOS to become enterprise ready overnight, not in months. Visit WorkOS.com to skip the unglamorous infrastructure work and focus on your product. Ridgline is redefining asset management technology as a true partner, not just a software vendor. They've helped firms 5X in scale, enabling faster growth, smarter operations, and a competitive edge. Visit Ridgelineapps.com to see what they can unlock for your firm.