Clay’s Unusual Path to Building a Multi-Billion Dollar Company

I feel like people don't talk enough about things that actually matter in building a business. I think capitalism rewards risk. You need courage to make a leap and actually commit to these ideas, to take real risk. You need to not know what's going to happen, genuinely, so you're going to discover something new.

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. That's when you can take real risk.

Can you describe the long, strange journey you've been on—why you started, 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 story so interesting.

We started with the really abstract ambition: how do we give the power of programming to more people? My co-founder Nikolai and I had worked in product, even though we both studied engineering, and we were trying to build things. 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 liked tools like Ableton Live. I have an idea; I can extract it from my mind and into the machine. We were also on this kick of looking at the history of computation and things like, in the 1960s, the Mother of All Demos, just seeing the fluidity of the interaction between you and a computer. It needs to be super fluid for it actually to lead you to the next stage of thinking, right?

You need low latency between “I have an idea” and “it happened.” 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, it really is like the material is computation. It's kind of like if, in the past, it was oil, steel, or whatever it is, today it's computation. The more we can give that to more people, the more interesting things happen. The more egalitarian it is.

It's almost interesting because that was our desire, and there were no LLMs. We started off by thinking about the terminal, and we were like, how do we reinvent the terminal where engineers are spending all of their time? Then we were 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 consumers or business users? We ended up deciding on business users for a variety of reasons.

Within that, we were like, okay, which department in a business actually has a ton of ideas but isn't able to execute them? We 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 and kind of wild. We have one company that sells to businesses that have a lot of garbage, right? Now they're using Google's 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 at scale. Now something like Clay can actually translate that for you. Because of that—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 were 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, break it down, and then execute it? I think we've also kept that ethos in the company.

That's what makes us really different from everybody else in our space. There are little, simple things that we've been saying out loud, but I think people don't really believe that that's why it works. One is: it's a creative task. If it's a creative task, we need to leave it somewhat open-ended.

A lot of companies that counter-position to Clay, or are in the space, are like, “Hey, what you really want is salespeople who are literally coin-operated,” right? What you need is something that's super easy to use. It gives you the answer, tells you who you're selling to and what you're saying, and it just works.

Whereas we think your role in sales is to find go-to-market alpha. How are you different from 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, try things out, and see what works. We built that instead, which was very counterintuitive.

Describe the takeoff of chapter 2: okay, now LLMs come out. What happened in that moment, what did that moment feel like, and what have the subchapters been since?

What's interesting in that story, and what I think is maybe worth talking a bit more about, is that it wasn't as simple as this was back in 2022 and we hadn't 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. We're going to support them in public and build a community.”

We took a lot of decisions that I think were non-obvious. The main thing that happened was really the courage and commitment to making those decisions that actually allowed the company to take off. The company was already taking off before ChatGPT came out. We were well set up to include LLMs in Clay because, first, we were set up to allow any integration to anything, and second, we were a coding-like product designed with go-to-market primitives. As soon as we had LLMs, it just boosted everything.

There were 3 core assumptions that we made, and I actually think this is how to build a really big company and one that grows really quickly. We went from 1 to 100 in 2 years. But that wouldn't work if we weren't pointing in the right direction. You need to 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're going to give them the most powerful tool instead of the most 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 role. We're going to call the subset of jobs to be done go-to-market engineering to give it a framing, right?

The tasks to be done are all the things that you need to do, like the activities to grow your business and remove any obstacles to growth. The last part was: we're going to charge for usage instead of per seat because we're trying to get more productivity. If you have fewer people, we didn't want that to be an anti-incentive for us. If you just look at those 3 decisions, almost every other decision in the company falls immediately out of those.

Then anyone can come up with what we should do next if you believe these 3 things. I think that's the best way to run a company that's growing really quickly, because I just have to communicate to you these 3 things that we're assuming. Whenever you're making a decision, check to see if it works within these 3 concepts.

1. Courage, Truth & Justice

I feel like people don't talk enough about the things that actually matter in building a business. I had this dream—it was kind of like a vision—where I saw lots of statues in a modern city, but I was wondering, we don't build statues anymore. If you look at old republics, they would have statues for concepts like courage or integrity, and there were gods for these different things.

2. Capitalism & Risks

I feel like we've forgotten that those are the things that actually matter—the abstract ideas of courage, integrity, or justice—in the moment when you're building a company. It was actually: hey, you need courage to make a leap and actually commit to these ideas, and then see what the logical conclusion is if we take these ideas seriously all the way to the end.

If you can put 3 statues off the elevator in the lobby, what 3 would you build?

Courage, because it’s—one thing that I think a lot about is that capitalism rewards risk more than anything else. I think a lot of people think it rewards meritocracy. There are a lot of people who are 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, either. Again, there are a lot of really skilled people. There are people who do things that I can’t even dream of—they’re eating a sword or 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 as well.

I don’t have a strong comment on whether that’s good or bad. I’m just trying to figure out what’s actually happening. And so, courage is necessary to take real risk.

See.

There are a lot of people who think they’re taking risks but aren’t taking real risks, right? I talked to one founder who went to a good school, then went to Y Combinator, and then was telling me about his company. He said, “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 and actually committing yourself to serving some group of people in some specific way.

For me, at least, my definition of risk, or how I’ve experienced it, is that you need to genuinely not know what’s going to happen. So you’re going to discover something new. You also need to have—I think it needs to be coupled with—a high potential for shame. You can fail in a way that feels scary or maybe associated with shame.

When you’re doing that, you’re genuinely about to discover something new and learn from it. That’s when you can take real risk. To do that, you then need to have many traits. One of them is courage.

Let’s take justice for a second, because I want to live in a stable society that allows me to have the time and space to think of things. I think—and just to explore—the world is pretty crazy. I went to see this movie called Stop Making Sense.

I was downstairs in the movie theater, and I had a joint that I was about to smoke. I was trying to light it up, but I didn’t have a lighter, so I asked the guy who was standing there, “Hey, can I borrow your lighter?” He was like, “Sure, can I ask you a question?” 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 haven’t even smoked my joint yet.

Well, if I was just thrown into this and I was like, “What is this?” I think 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. We should be spending more time exploring that. To do that, I feel like we need stability.

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.

If you’re thinking about the economy or countries, there’s no way to—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 that when I have power over people, you tend to think, “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, how do you treat people with respect and fairness all the time, in every situation, whether you’re hiring them or firing them or disagreeing over what they should be doing? I think that maybe is what’s fueling this democratization, right? You want people to be stable in a place where they feel like they have the opportunity to get to where you’ve gotten to, as long as there’s some kind of fair chance for that. They’re okay with what they’ve gotten if they feel like, “Hey, this is what’s available to me at the moment.”

As a side note, I think this is just an internal thing that I’ve had. I used to play soccer, and even on my team, if I felt like we fouled the other team and we could get away with it, I would have a really weird feeling that my integrity was off.

Do you have a sense of where that came from?

It’s some kind of intuitive knowing for myself that I’m a long-term greedy person. This is one of the things we talk a lot about at the company: how do you be long-term greedy? I think the only way to be long-term greedy is to stay in integrity, so people feel like there’s integrity all the way along.

I think it’s also just a belief in yourself, right? You don’t have to cheat in the short term to get something. You’re going to win. Maybe one small thing about this is, let’s say you’re playing a soccer game and you feel like you cheated or this wasn’t fair, and then you won—it doesn’t feel as good.

I did hear your interview with Brian Chesky, the statement he made around getting to $100 billion and—

Feeling like—

Yeah. I actually felt like I related. We’re obviously in a much smaller spot, but even early on when we raised our Series A, I remember having that sensation of, “Oh, there’s no—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’s because you know everything that you’re thinking. You know everything—everything that you’ve done. So I know everything that I’m thinking about or doing, and my standards are higher than anyone else’s.

3. Creating from Wholeness

There’s this thing I like to do where, when I spend some time with somebody, I wait an hour and then I write down notes in my phone because I like to benefit from the hour. It’s like a cleansing function or something. Whatever lasts in my brain through that hour, I want to write down. When we last were together, this is the one thing I wrote down: this notion of optimizing for self-respect over everything else as the North Star for behaving.

Yeah.

I’m curious how that relates back to—I’ll get to truth in a second—but how optimizing for self-respect relates back to risk and courage. Do you think those things are related? The question behind the question is: how do you think it’s possible to help people become more courageous and take more risk?

I think in order to do that, you just need to understand your mind and your motivations more and be more honest about that. 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—the motivation of the founder. I think probably the honest story is a mixture of things, and we don’t talk about that in public, right?

So I think, 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 at a world-class level? Can I get that now? I’ve had friends come up to me; they’re like, “Hey, I don’t care if you succeed or fail.”

“I love you.” I was like, “Wow, that’s actually helpful.” I didn’t think it would be, but it was like, well, some part of my desire must be fueled by that, and I can get that right now. 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: “Hey, we invest in someone who has a chip on their shoulder, right? Or has some kind of lack that they’re trying to fulfill.” This is common across creative work, too. The trope is that you’re depressed or anxious or whatever, and you’re trying to fill that—and you’re actually afraid to lose that depression or anxiety 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.” I went around, probably pretty annoyingly, telling people, “I have everything I need. I’m good.”

Post-lack.

Post-lack, 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 tremendously misunderstanding this, in my opinion. It’s kind of like, well, if we were in a post-scarcity world, no one would do anything. Everybody would just be hanging out. I was like, “Have you been to Burning Man? People are still doing stuff, you know? And they have things.”

I think you can create from a place of wholeness, and in fact, you will be less destructive in the world. So I think you’ll create less damage, because we keep thinking, “Hey, let’s think of our customers. What are we trying to give them?” Stop thinking about others. In an organization, why do people keep saying “customers first”? It’s because when you’re in a company, things start to happen where this person is 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 whole 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, Jony Ive and Steve Jobs, were almost undoubtedly creating from this generative place. I don’t know if they’d use the same terminology or something, but you read it all—it’s all there. And they’re the most adored, right, 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 introspection is a key tool in the toolkit to get from one to the other. I’m curious what your experience has been, or what you would offer about that phase change.

I kind of understand the motivation here, because one thing I talk a lot about and have thought about for myself is the amount of work you’re doing versus meta-analysis. It can sometimes flip, right? You should be 90% of the time doing and 10% of the time meta-analyzing.

Sometimes at work, we’ve had this happen a lot, and I talk to the team a lot about it. People are like, “Hey, what is going to happen in 1 year? Or 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.”

I think my sense is that his conversation around that is—and also, by the way, if you’re trying to build—I think his example was Walmart, right? It was like, if you try to build more Walmarts, yes, you should always be thinking about waking up in the morning and building more Walmarts. But at some scale, once 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. You’re a representative now. You’re not a completely independent actor. And we have the power to pull some of that stuff back from you.

So, is there anything that you did in particular—

Right.

—as just about your specific story, going from kind of lack to wholeness?

4. The 10-Day Silent Retreat

Right. For me, I think the introspection was a journey to understand why ambition. I was suspicious of my own ambition. I was like, “What am I trying to get out of this?”

Actually, I think part of why the company took some time to take off was because I was grappling with that. That led me to investigate which parts of me were trying to be expressed through this. That was just my own personal interest. I found that I couldn’t do something without understanding my motivation for it, because I was looking at people who were further ahead in my field.

If you’re a great businessperson or you’ve built a great company, I was like, “Do I want that?” I think it was also coming from valuing my time and myself, really. I was having this experience where I was 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; other people want to do that, too.” Or you can 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?”

You can succeed and create a lot of damage in the world. Going back to the kind of—I was thinking a lot about death, right? If you’re on your deathbed, what are you thinking? How does it feel in that moment? If you had a moment to reflect, how do you judge yourself?

For me, there’s the experience of every day and living a life that you feel is worthwhile on a day-to-day basis. There’s also how you impacted the world, if you did impact it. I wanted to make sure that I felt like I really grappled with that correctly, and that I didn’t just try to accumulate resources and be like, “Hey, I did something big. I accumulated some resources.”

It’s funny; it does go back to this justice principle. If you’re going to do something big, you need to think about the consequences of taking that role, because it’s just a 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 stage?”

Right. Probably no one does that.

I remember when I was much younger, I thought, “Oh, 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? Or is it just that I want the control to pick the causes that I want?

Maybe one more thing about the death thing that I think is interesting was my own insight. 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 a spiritual experience. It was called Hirudaya, not Vipassana.

Hirudaya’s approach there is a nondual approach to meditation. Typically, you meditate on your breath or some object, whereas in nondual traditions—it’s called the direct path—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 not recommend it.

Anyway, I’m doing this thing. On the 5th day, I had this big insight where I was like, “I’ve figured it out. I’ve got it.” Then on the 7th day, I was like, “Okay, well, what now?” I started imagining going back and telling my friends about this insight, but I realized I wasn’t there—I was just imagining the future. I kept wanting to go toward the end.

Then I had this really big flash of insight that I tried to remember: Whenever you’re picturing or anticipating the future, it’s kind of like Freud’s death drive, right? The only thing that happens in the future is that you die, in the far future, whatever it is. So you’re accelerating that.

As soon as I had that thought—that actually thinking about the future is the death drive—I immediately felt back in my own body in the moment. I felt the boredom of where I was, and I was like, “Wow, this is such delicious boredom.”

I finally got that insight: I’m so grateful to be bored right now, because it’s so amazing. I also realized that I have this scarcity—food scarcity. I was thinking constantly about food and where I was going to eat. Then I just had this one pea, and it exploded in my head. I was like, “This is too much. I can’t eat anymore.”

But I realized that I have an accumulation tendency. With food, it’s like, “Where is the food going to come from?” And then with the company, I notice I’m like, “Where is the next ARR going to come from?” Now I’m aware of that, and I’m aware of when I have enough. Then I can take more risk.

I don't need to accumulate something that's way beyond what we actually need.

What was the day 5 insight, or was that the insight itself?

No, the day 5 insight was a momentary experience of understanding what matters, or something like that, because I felt like, “Oh, I'm connected to all things. I am a component, or a part, of this whole thing, and I'm connected to all things, and they all matter.” I had this kind of thought: “One, I'm no better than and no worse than anyone else.”

But it also made me feel this real empathy. When I see someone who's suffering, they're also me. And not like I empathize with them as if I were them. I'm like, “This is actually me.” That's kind of a really out-there thought or belief.

Strangely enough, it's actually not at all. It's the longest-lasting set of beliefs, and it's at the heart of the deepest, richest philosophical traditions.

What was crazy wasn't the idea, it was the—

Experience.

—the experience of really feeling that. And then knowing that, when I hear something in Buddhism that's just like “freedom of all beings,” or knowing that the suffering of one person is the suffering of everyone.

So, back to the justice thing: 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 the capacity. But to really know that every single person is carrying it for me, rather than thinking they messed up and I'm better because I worked hard and did X, Y, and Z.

Mhm. So, if we're back to our states, is that then truth? Is the day 5 insight—

Yeah.

Is that just true?

Yeah. If we go back to capital-T truth, it's really understanding that. And then I understand why, in philosophical traditions or even in religions, there's this idea of remembrance, right? Because I can get that momentary understanding, but remembering it in the moment when I'm making a decision about my business or my personal life is very tricky.

But I do think that is what's necessary for us to get to the next stage of what's interesting in the world. There are so many mysteries—scientific mysteries, just so many interesting things. I feel, probably like many other people, that we're squabbling in circular ways around the same nonsense. Truly, my real anger is, “What are we doing? We're wasting our time, or we're wasting our human potential. We're wasting our time.”

If I hear and digest all of that, and then I imagine, okay, this guy is now running a software startup—

Right.

I might imagine that that startup is run in some unusual ways.

Right.

And so I'm curious what those are, and why you arrived at—

Yeah.

—unusual ways of running the business.

It's back to the meta-reflection point: yes, there are some unusual ways in which we run the business. I think it's important to be careful of how much you push ideas onto other people or project your beliefs onto them, and also to remember what context you're working in. It's almost like telling a story, right?

If this is the normal way to run a business, and then you think that it's this completely bizarro way over here, you also need to take the steps to tell the story. I think it's the same in product development, right? I can't just give you a product that you have no context for. You don't even understand how to interact with it. So I think it's, “Hey, these are my personal beliefs and my interests that are underlying some of the normal activities that we do, and then there are 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 overinvest in things that people typically underinvest in. What does that mean? We've overinvested in recruiting, in brand, in content, and in community building. We've hired people who are very overqualified for some of these roles, who are doing them for the first time.

We've paid them as if they were, for example, a PM. We actually just published an article about this with one person who was an early employee, Mishti, and she took a content role. She would never have taken a content role, right? It's typically not the most highly paid thing in a company, or it's extra, and we compensated her like a PM and were like, “Go do it.”

So we take those kinds of risks, and then we stick with them. I think another thing, by the way, with risks is that when you couple risks and courage, the next part is commitment. You actually need to follow through to see what ends up happening. You can't just quit in the beginning.

5. Re-Enchanting the World

We take that seriously, and if we see that somebody is really skilled or has star potential, we stay with them for way longer than most. Everybody talks about hiring fast and firing fast. We've had people who, 9 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, I would say 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 my co-founder Varun and I have talked about is that 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 say, “This person was good; this person was bad.” Were you good in the moment that we needed you to be? Actually, 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. They've gone to other places and done a really good job. So I think it's important to be nuanced.

But then there are some other things where I think some of the things that people have covered about us in the past are, like, clowning, for example. I discovered clowning.

What's clowning exactly?

When I first heard just the word “clowning,” I was like, “What is this?” I think of it as edgy improv. There are kind of 4 types of clowning. There's physical clowning, which is the one you would imagine when you think of clowning.

There's emotional range: let me make you happy, then make you sad, then make you happy, so you can feel the full range. There's the jester, which is telling truth to power. And then there's the trickster, which I think is pretty interesting: how do I tell you spiritual truths through jokes?

You realize, “Hey, everything does change.” That's a truth about the world, but I get you to experience that. We take things like that, or we're really into magicians at Clay, and we incorporate them into our events or things that we do.

We take risks. Our brand takes a lot of risks—way more risks than I think general B2B brands. That's why people love the brand and the company. It's authentic to us, but it's also, I think, honest. 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.

Where do you learn from magicians?

I actually think the trickster thing is the common thread between us. There's this place called 69 Atlantic, and the thing that I remember from these really incredible magicians is that it's not just sleight of hand. There's a storytelling component.

A lot of them are telling a story about a deep understanding of how your mind works or how the world works. Or they're like, “Hey, I'm showing you this thing,” but really what they're trying to do is spark curiosity.

We're actually going to do something about this at Clay. We're calling it “Re-enchanting the World,” right? In a world where there is AI, it's literally magic in some form, right? There's a lot of—this is magic, right? A lot of these things that we're sitting in front of are still magic. It's pretty wild.

To re-enchant the world again and not make it this boring place where you think you understand how it works, because you really don't. I think they're doing simple things to reignite that feeling of wonder.

If you take that feeling of wonder into your everyday life, you're a friendlier person because you're not like, “Oh, I understand how this person works.” You're more curious. It makes you more curious about our customers. It makes us interact in a more pleasant way because we're like, “Oh, there's stuff to learn here.”

So what I've actually been getting from this magic stuff is remembering what it feels like to be like, “I have no idea how this is 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—

Yeah.

—your many, many experiences with music.

One of the key things with music versus other kinds of things is time. You can't listen to a song without time. Time is actually a core component, and silence is a core component—the spaces between things. So it's a good reminder that those are fundamental things that you have to work with.

It's very Zen. You know, it's like where the thing isn't—where the room isn't—is where we are, right? If this room was full of things, we couldn't sit in here. We only think about making things; we don't think about removing things. And we don't think about things unfolding, right? I think video is also like that, but a painting isn't. You can see it all at once.

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 it, and they haven't. But the piece that I was reading was talking about endings. We always think about beginnings, but we don't really think about endings.

When you're starting a company, you're not like, "Well, what about all the people that I'm going to fire?" So many crazy things genuinely happen as soon as you have a large number of people. All kinds of people get sick. People's parents—you know, you're dealing with a microcosm of humanity. You're running 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 by repeating, and the volume goes down. Some things end suddenly. Some things end with a whimper or with intensity. You can think of these as different ways to end something.

Another one that I think is really cool is an essay that I read called “The Emancipation of Dissonance,” which, first of all, is a really cool title. It was theorizing the history of music as a history of accepting more sounds as music. In the beginning, it was maybe just drumming. First, it's the tonic: you play a C and then the C an octave above. Then it was adding the fifth—that's why it's called the perfect fifth—and a lot of Baroque music had that.

Then people started adding the third, which is what creates chords, like minor and major chords. Initially, that was resisted. People were like, "What the hell is this? This feels off." Then you add the seventh, where you get jazz, and people were like, "That's unacceptable. This is not music." Eventually, you start to add more and more tones.

6. Founder's Vision & Death Doulas

This was arguing for not just the—Western music has 12 notes, but in Arabic or Indian music, there are 24, and there are 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, and 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 through-line in the world we're going into: how important it will be to make people feel something.

Right.

But maybe also something new.

Yeah.

Like, if we can create anything, the logos of it all is, "Yeah, whatever. You can create anything you want." The pathos becomes really important on top of that. And the insight from music is: make people feel something new.

We use this a lot. I'm telling people, "Hey, we're not building a microwave." Microwaves are useful, but they're commoditized, right? You just go and say, "Hey, 1 minute, heat it." It does what it needs to do. There's no difference between most of them.

But we're building a guitar, right? With a guitar, there's just 6 strings and 12 frets, but you could spend your whole life just getting better at that. You can only be playing one type of style of music, and it's still new.

I actually think if you bring that to sales or go-to-market things, it can feel like a crazy stretch. But if you respect that discipline and ask, "What is the ultimate version of sales? Or marketing or customer success?" that's why it's called go-to-market, in my opinion. It's just like, "How do I take the thing that I made and give it to you when you need it?"

And that's the—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." Right? And that's what you actually want to get to.

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.

Mhm.

And so we're thinking about all of the creative ways to figure that out.

One really interesting conversation you and I have had before is about the role of vision in company building—

Yeah.

—and the leader's responsibility, or lack thereof, to have one in the first place.

Oh, yeah.

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. Actually, let's turn it back to one of our statues: truth. You need to say the truth. 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. Don't say something that actually isn't happening.

That's my answer to that. I do think ultimately you need to have some destination, 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 medical discoveries are complete coincidences. So many of the most advanced things that we've got here—I don't know, the cosmic microwave background—complete coincidence. You couldn't have gone out and said, "I want to discover the cosmic microwave background." There are so many of these things.

I think we're telling ourselves a story that is not true about the nature of discovery and how it happens. 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, I think I'm 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. All the stories of greatness are like, "I was 13 and I was this one thing, and then I dedicated my whole life to it." I think that happens, and it also happens in other ways.

So, optimized for discovery rather than destination would be one way to think about it.

I would say leave the space for the opportunities to discover. If you do have a vision, you should be clear about that and clear about how confident you are in that. 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.

The Native American traditions that are coming up for me—I don't know why this is relevant—are like this: there are things called vision quests, where you go and fast for a few days and ask for a vision. And I think 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 the vision is wrong. A lot of companies that started 5 or 6 years ago are kind of confused now because things have changed. Well, it’s time to change the vision. You don’t need to settle on a new one immediately. You can say, “Hey, we don’t actually know what we’re doing right now.” And we can take the next step—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 about what the vision is within the scope of what we’re doing. We’re basically just helping every company in the world find who their best customer is, 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, achieving a level of wealth that, by any measure, is extraordinary. What has that process been like, and what has that taught you?

The initial thing that I had thought was true is true: 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. But what material abundance gives you is the reality of getting your time back.

I’m choosing, for example, to build this company. I don’t have to. 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.

That goes back to that truth part. It’s really empowering—I can make my own choices and 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. So, I think having the opportunity to choose what I do with my time and to take bigger swings just feels really important. And then it’s, what responsibility do I owe back to society?

You also once said to me 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. 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. 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 and what I think you want, assuming that you are really intelligent and have access to the same information as me. We need to know what you want and what the options available are, and then we might still disagree. But at least we are disagreeing from a place of clarity rather than from a place of misunderstanding.

Let’s say we’re asking someone to leave Clay. In most cases, as long as the person is in a shared reality with us in a way that’s based on clear communication, right? Like, “Hey, 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.” But I don’t know. Let’s just say, “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.”

At one point, I told someone, “Hey, listen, I’ve lost faith in your ability to bridge the gap.” And I’m the CEO, so it’s not a good situation for you. It doesn’t make sense, right? 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.

So, 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 direct and clear about it and also own up to the fact that this is my call. I think a lot of people actually really appreciate that, and they’re just like, “Okay, I get 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 you’re going to say in the future to other people, right? 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 strengths. I think here are the gaps that we have in our organization that didn’t support them.”

7. The Kindest Thing

How do you not think about that, right? When I call up a reference, it’s 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—that’s obviously not true, right? 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 that these are the things that I think are actually interesting to talk through.

Part of my experience of building a company was that 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? I think we’re not talking about these things because the risk is too high, right?

If I talk about what I’m doing in a company and how I’m treating people, maybe someone will sue you, or someone will lose customers’ faith in you. But actually, these are the interesting things. 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 5 people who’ve done it, and they tell me.

By the way, I’ve done things that are completely the opposite of that, and it’s worked. The reality is, 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 from 50 to 300 people. None of them happened. We had some other things that happened, but I didn’t have the typical problems because I didn’t do it the typical way.

As we approach 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 that you told me something like you wish there was something like a death doula for companies.

All right. I’m just like, why are we not talking about whether it is good to scale every business? Every business—I mean, people talk about it a little bit in this really boring, super-worn-out way: Should you raise VC capital, or should you bootstrap? Those are completely uninteresting ways of talking about it.

It’s as 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, as a society, be incentivizing all businesses to scale? We all know this problem, which is, “Hey, this restaurant was really good, and now it sucks.”

I think there’s a life cycle to things, and maybe part of this meditation retreat and thinking about the death thing, I’ve been thinking about whether there’s a life cycle to companies and whether we should just be okay with that.

I’ll pick Microsoft for a second. You have an initial mission: put a computer on every desk. I remember that mission, right? When I was a kid, you did put a computer on every desk. But now the mission is devices and services and doing cool things, right?

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. Should you disband, or should you keep 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 of this disruption is happening, to start thinking about the new ways of doing this. I’m curious about it. But a death doula 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 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.

When you and I are together, I feel like we always talk a little bit about Clay and a lot about even more interesting things. And Clay is very interesting.

Yeah.

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’ve already mentioned, actually, but a few friends have come up to me, especially before Clay succeeded, and were like, “Hey, you don’t need to do anything.

We just love you anyway. And then I realized, “Oh, I also don’t care what they’re doing. I don’t care what they achieve. I just implicitly like this person and love them.” Knowing that I had that, and that I could give that back to myself as well without any achievement—I think my childhood wiring was feeling like I must achieve in order to have care and love. I was like, “I actually don’t need that.”

It created a ton of clarity where I was like, “I’m doing things because I want to, not because I need something from it.” 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 want it to evolve the way it wants to evolve.

Thank you so much for your time.

Yeah, thank you, Peter.