She Turned "Art Isn't Serious" Into a $6M Startup | Kendall Warson - Cohart

Shamil Malachiyev: Hello, everyone. Our guest today has spent years in the art industry, curating shows with over 200,000-person audiences across North America and Asia while managing a network of over 500 international artists. Now, having raised over $6 million, she is building Cohart, a platform that provides the easiest way today to buy, sell and discover art online. From Brooklyn, New York, please welcome Kendall Warson.

Kendall Warson: What an intro. I love it.

Shamil Malachiyev: I did my preparation. Can you tell us a bit about your mission at Cohart? What are you trying to bring into this world?

Kendall Warson: Absolutely. As you mentioned, I used to build these traveling immersive art shows throughout the US and throughout Asia. I got to work with a lot of artists one on one and realized that the majority are small to medium-sized business owners. They're doing everything from invoicing to filing taxes, and most of them don't have a central system to do that. They're really using this hodgepodge of multiple tools and software systems. Only 14% of artists have galleries. So 86-plus percent are using this assemblage of systems that don't really work for them.

So when we were looking at the mission statement and just thinking about art, it was: how do these people really sell art? And it's fundamentally pretty broken. As an artist, there's no good way to find a distribution channel to sell, to manage your business. And at the same time, I'm a millennial, and looking around and seeing my friends think about art, it was sort of the last vertical that felt inaccessible. You look at music or travel or food or fashion, and there are so many ways to feel confident about other cultural mediums. But with art, the majority of people don't feel like collectors. It still feels like a fancy word, a sort of unattainable identity.

So mission-statement-wise, it was: selling is broken, but so is buying, and so is discovering. Can we build a new type of platform that really brings collecting into the next generation and helps broaden the market? Ultimately we all own art. We all have stuff on our walls, but so few of us have a positive experience when we're buying and collecting. So we're trying to address both sides of the equation and build a category-defining company that brings collecting, selling and discovery into the next chapter of the market.

Shamil Malachiyev: What I've noticed in my life is that people who are very creative tend to lack business savviness. Without a platform like this, how would painters and artists go about presenting their work? Where do you go?

Kendall Warson: It's so interesting. There's this saying that if people are still using Venmo for a purchase outside of a friend-to-friend transaction, there's an opportunity there. And we started to see that with artists. People are selling $5,000 paintings and sending it in a DM on Venmo. That's crazy. They don't have a central place to send a credible invoice, no way to track that buyer's information and put them into a funnel, no place to store their email. Today, most artists get an MFA. They study art, then a master's in art, and there's no business course. It's sort of: get a gallery, or that's it.

Shamil Malachiyev: Go outside and post your work near the park to showcase.

Kendall Warson: Exactly. Galleries aren't necessarily bad actors, but they do take 50-plus percent of your sales. So even if you are selling with a gallery and you are successful in getting representation, it's still pretty hard to make your business work. But what's been really interesting is Instagram has disrupted this market tremendously. Artsy came out in, I think, 2008, and that was the first revolutionary platform for moving the art world online. People could post work online, and all of a sudden access broadened. Then Instagram started to disrupt it around 2014, 2015, and artists realized: I can have my own distribution channel, I can sell directly.

That's really what we've been picking up on, navigating that generation of artists. If they have their own distribution channel, how are they doing everything else? Can we centralize that, and then ultimately build the best distribution channel that's focused on art? The short answer is there's no good system today, and that's why we're building this. A lot of artists need it. They don't want to spend time on admin. They want to make art and connect with their audiences, and they don't have the tools, resources and education to streamline a business operation on their own.

Shamil Malachiyev: What do you think affects the overall demand for art transactions? Are there any trends?

Kendall Warson: The word Cohart is about art discovery through the lens of human connection and community. Fundamentally, what we are working on is a socially signaled marketplace, a space where you can see who's collecting from whom and driving scarcity through signaling. It's something we see in a lot of other markets: StockX famously started building price graphs, or Google Maps, where you can see who's going to different places and what the reviews are.

When you look at art online, it's just this JPEG at a price point. How do you know that should be $5,000 or $50,000 or $50? How do you know that artist is credible? There's just no way to perceive value. So the dream and the big vision for Cohart is that you see a piece of art and you can see the artist's history, you can see who they're connected to. I can see what you're collecting. And if you're a hot collector who's made some great investments, people will follow you, you'll have a halo effect, and you'll drive more traffic and visibility to the artists you collect from.

That's how the traditional art world works, and we're trying to move that behavior online. The traditional art world is very much in person. It's driven by fairs and gallery shows and auction houses, and it's very much a see-and-be-seen scene. Who's there? Which critic is there? Who's collecting first? How are you driving scarcity around a certain number of artists? A lot of artists in that more traditional system have a limit on how many paintings they make, because they want to drive scarcity. The gallerists work with them to make sure there's a certain number of collectors collecting the work and only a certain amount available, because you want the supply constrained so the demand grows.

The whole network is fueled by that social side of things, and value is ultimately what's driven from that whole network effect. That's something we're really excited about disrupting. In general, the art market has been a very relationship-fueled market, and that's what drives all the trends fundamentally.

Shamil Malachiyev: How important is the role of storytelling? Because usually you don't just compare two paintings on technique. Well, to some extent. But what really drives the value is the personal story, what it represents. Is that something you encourage people on your platform to do?

Kendall Warson: Fundamentally, storytelling is branding. Say you're in a Walgreens and you see a Revlon lipstick, or a Tommy Hilfiger shirt. You're going to have seen that billboard image of the brand. Tommy Hilfiger has a lifestyle, an aspirational persona, and wearing the logo kind of justifies spending a certain amount of money on that garment. But if it doesn't have a logo, if you've never heard the story of Tommy Hilfiger, it's just this $120 shirt, and it's like: why would you buy it?

For art, there's this white-cube tradition: present your work in an opaque box, don't say what the price is, don't have an accessible website online. The traditional ethos is to be discreet. And I just think it's really hard to connect with buyers when you're presenting your work like that. The opposite approach is much more of a brand-driven storytelling approach, where an artist really communicates their story. They have ownership over their message. They brand their art with their personality. All of our successful artists are at the forefront of their brand: they spend 50% of their time marketing, 50% of their time making work, and they're proud to talk about it.

It's one of those things where once you meet them and hear the story, you want to buy it. If you connect with them and end up buying the piece, you tell your friends about it, and you have this emotional resonance with that object. That's so powerful in terms of unlocking more demand for your work. I think the most successful artists of the subsequent generations will be owners of their brand and their story. That's very different from the gallery model, where someone else had ownership of your brand and you never really had the capacity to tell your own story. But that's what we're all looking for in the next generation. We want to feel connected to the work itself.

Shamil Malachiyev: If you ask a lot of younger people what they think about collections and art, they'd probably remember the NFT craze, the rise and the crash of the NFT era. Has this affected much of what Cohart was trying to be?

Kendall Warson: To me, the NFT craze was almost an example case study of the fact that collecting is social. People want to collect together, they want to buy into value together, and they want to feel recognized for what they're spending money on as part of a communally or socially validated experience. We originally started in early 2021, when all of that was booming. I've worked with a lot of digital artists throughout my career, and we see it as a super credible medium. Digital art is just as credible as physical art.

I think for us, we see a bit of a difference between Web2 and Web3 communities. A lot of Web2 people are on Instagram, for example, whereas Web3 was mostly Twitter. And when you're building a company, you have to choose. You have to get really focused about a distribution channel, a marketing approach and your messaging. We decided to take a step towards the Web2 audience, not disassociating from the Web3 audience, but really talking to physical art as a medium, because we felt there was a big opportunity there. When we were fundraising, a lot of people at that time were asking: why do you want to do physical art? Why wouldn't you just double down on digital art? And then after the bubble popped, people came back to us: okay, actually. It's been interesting to watch.

NFTs are exemplary of the fact that we do want to see who's collecting from whom, and we want to be part of this communal collecting experience. But that can apply to physical art just as much as it applies to digital art.

Shamil Malachiyev: I was thinking about how the TV series The Queen's Gambit affected the whole world of chess and the number of people getting into it. After the NFT craze went down, did you have a lot of people who now knew how to collect but wanted something that holds? Because sometimes it's a gamble, and if you switched from digital to traditional, you'd still have an incredible painting with a story. Did you see people switching?

Kendall Warson: It's a great question. I think so. It's like what you mentioned with The Queen's Gambit. It's a pathway towards a conversation about chess, and it makes chess feel more attainable. That's also kind of an inaccessible game; it has this prestige around it. But when you learn about the game, all of a sudden you feel more empowered to talk about it, and it feels more attainable to call yourself a chess player or to explore the game more.

The same thing has happened with art. People are treating fashion, like sneaker collecting, as a way to express themselves. A lot of people are building up more of a digital brand, and that's pretty creative. The more you're expressing yourself creatively, the more you open yourself to art and feel empowered to start thinking about collecting. So of course NFTs had an impact on that.

In our early user interviews there was a really profound story where this guy was saying that with art collecting, you kind of need someone to hold your hand a little bit and guide you through. And once you're there, it's like: wow, there's this whole world I can immerse myself in and be a part of. It's not that the door is closed, it just seems like it is. So the more awareness you have, and the more people demystify it for you, the more pathways there are for people to feel empowered to experience art. You don't need to collect to go to a fair or a gallery show, but so many people are just scared to walk through the door, because the industry has been so intimidating, and that's been purposeful. It's not the consumer's fault. It's the capital-A Art World and how it's been structured. But I fundamentally think that's shifting as we find more ways to express ourselves creatively, as these digital trends take off, and as we try to spend more time doing things that fulfill us and round out our identity outside of work.

Shamil Malachiyev: How long did it take from when you conceived the idea of Cohart until you actually took the first physical step?

Kendall Warson: That's the hardest part, right? Building a company is really challenging. The day-to-day is very challenging. But the first step, that leap of faith, incorporating a company, telling people you're starting something, is daunting, because a lot of people are naysayers, kind of following the herd.

For me, it took some time to build up my confidence to feel like this is something I really want to do. At my previous startup, I was the first employee. So I'd seen the whole thing grow, and I was almost operating as a CEO within that company, but I didn't call myself a CEO. I sort of thought someone else would have the idea and I could execute it. But I saw in that company this massive market opportunity for something like Cohart to exist and carry the art work forward. My sister's a venture capitalist, so I called her and said, I have this idea. And she said, being a founder is the hardest job in the world. You can do it, but it's going to be really, really hard. Not very inspiring. But I love challenging things. As a founder, you're attracted to things that push you.

After that conversation, I started to explore it. And then I met Shyevin, who is really my better half and my counterpart. When you have a partner, it helps crystallize momentum and helps you keep pushing forward. We spent about six months talking to people and trying to navigate: how do we position this? What's the opportunity? How are we going to stay focused? We started doing these talks with our audience, these user interviews, and it went from three people on a Zoom to a hundred. This was during COVID. We were talking about these prototypes and people were saying, we really want you to build this. Hearing that validation was extremely motivational for us, and that's what catalyzed our first angel check. Once you have a little bit of money in the bank and a Delaware C Corp, it's pretty real. At that point it happened before we knew it.

But Shyevin and I hadn't even met each other in person. It was all amidst the pandemic. We were just going back and forth on Zoom, and we were a year and a half into the company before we met in person, which is kind of shocking. But that's the COVID era of these startups, which is very different, I think, from how it would work today.

Shamil Malachiyev: Looking back at the whole history of working with Shyevin, what are the tricks and secrets that made your co-founder relationship work?

Kendall Warson: It's a relationship. If you think about friendship or a romantic relationship or the relationship with yourself, there's always work associated. You need to spend time on the relationship. You need to communicate. You need to reflect and invest in developing it. That's something I didn't really realize when we got started. I sort of thought, it's a business partner, things just happen and it grows. But she's in Asia, I'm in the US, she's a little bit older than I am. I was in my mid-20s at the time, and we come from very different backgrounds. Very different people, very different personalities, which is what makes it great. But in the early days, when there are really high highs and really low lows, if your relationship isn't strong, it can really throw you off.

And because we're not technical, we always had a third person who would come in and be the CTO or the technical person. We had a couple of instances where at one point that person was closer to her, and at another point closer to me. It kind of threw off our balance and equilibrium. So we worked with an executive coach and did a lot of founder relationship-building together, which was very helpful.

Shamil Malachiyev: What did that look like?

Kendall Warson: It's like founder therapy. It's a safe space. It's like couples therapy, right? You go in and you talk about what you're feeling with one another: how you need to feel more supported, insecurities you might have, challenges you're facing. And because the coach is trained in relationship management, they're able to guide that conversation and make a really safe space for you to be extremely transparent and get everything off your chest, versus holding it in.

It created this environment for us to now have an extremely open line of communication at all times. We're always listening to each other and able to express ourselves. And it creates a lot of mutual respect, where we both know our end goal is the same, and to get there we're going to have to compromise and concede and listen to one another and be effective partners. That is easier said than done when things get super stressful. But all in all, it's hard to be a solo founder, and if you have a partner, it really helps you get through those times that are extremely challenging, when you don't know what's going on, you don't know why you did this, it's not working, things are stuck. To have someone you can call and just talk to, someone who's not your sister, not your boyfriend, not a family member, someone who really understands and is in it with you: I think that's been instrumental for us. Our relationship and our partnership has been what's gotten the company to this stage.

Shamil Malachiyev: Looking back at the way you were raised as a child: if you could change something about the way you were raised, would you change anything, and what would it be?

Kendall Warson: I hope my parents don't listen to this. No, I think everyone has that story in their head, right? When they're a kid and they grow up, everyone has a chip on their shoulder. In the realm of spiritual work it's called your conditioning: how were you conditioned to think a certain way? And there's always some resentment people have. Most of the time it's "I wasn't raised to be ambitious enough" or "I was raised to be too ambitious". It's a story that we tell ourselves as children.

I've done a lot of that reflecting and understanding of the way I was raised, and that gets you to a certain point. And then you have to stop blaming your parents. You've got to take your deck of cards and deal your own hand. If you want to change the deck of cards, you have to go out and find new cards. Sitting there expecting something to change about your past is sort of pointless.

That said, I do think I was raised to be a founder. I had a unique childhood. As a young woman, my mom was the breadwinner of the household. She wasn't really handed anything in life and built a really successful corporate career from scratch. Seeing a female role model persevere through challenges, especially in those days, she was in banking, a very gendered industry. In her day she was the only woman in the room 95% of the time. Seeing her go through that and then tell me every day, you can do anything, you can be anything: it fundamentally changed the way I see the world. I see opportunities, I take risks, and I'm someone who is very much driven by a big vision. I think I can do anything. And that's a rare trait, especially for women, who are often taught not to take as many risks. My sister and I both share that, and it's all attributed to her. I'm really grateful that's been my experience.

Shamil Malachiyev: In order to get support and love at a young age, were there any requirements for you and your sister? You have to perform well, you have to get the best grades, you have to be the leader of the soccer team?

Kendall Warson: For sure. Again, I hope they don't listen to this.

Shamil Malachiyev: We'll keep it down.

Kendall Warson: We were raised, not strictly, but I'd say there was a high bar in our household. My parents didn't have much handed to them at all. They both worked, and they both have great work ethics. My whole extended family has, the right word is the opposite of entitled. It's a grit, a perseverance: you earn your reward, and if you don't show up to the table, what are you doing? You're wasting an opportunity. Life is this incredible experience that we have, and if you work hard, so much crystallizes from that. That's what creates opportunity, ways to be financially independent, have a family, live a great life. That discipline and that attitude was ingrained in me and my sisters at a very young age. And it could be represented in a grade: if you get a B, it's "what's going on?", because that's a symbol.

For me it was really hard, because I love photography. Going into college, everyone asks, what's your favorite class? I'd say photography, and everyone's kind of laughing at you, because it doesn't feel credible. I wanted to go to art school. I went to a summer program at Rhode Island School of Design when I was 16, and it was the first time I felt like I was really good at something. I got all A-pluses. I was just so engaged. I didn't have any art training. We didn't have crayons in our household growing up; it wasn't a crafty household. So my technique wasn't that good, because I didn't grow up drawing. But I really wanted to be a fashion designer. I had this vision and this dream of doing it. And I felt kind of laughed at by my family and the school environment I was in growing up.

I think I became a much more crystallized human at a younger age, because I had to fight against this perception of art not being a credible thing to do with your life. I put a stake in the ground and fought really hard to make it work, and I ended up going to art school. I went to Parsons, and I'm definitely the only one in my extended family to go to design school. In my whole family history, I think I'd be the only person. And showing up at design school, I recognized: I've made this insane decision not to study business and to study design. I need to make this work.

Part of what motivates me with Cohart is that I believe art is a big opportunity, that everyone buys art and there's a lot of business abundance there. And there's this perception that it's just this lolly-dolly thing where people aren't serious and they're not credible business people, and therefore: why would you talk about art? Why would you make art? Why would you collect art? There's a lot of shame associated with it. So my chip on my shoulder with Cohart is ultimately about proving that's not true, proving that there's something here that has just been societally perceived in a way that makes it feel like it's not a good way to spend your time.

Shamil Malachiyev: What would it have meant for you to get that support from your parents, for that younger Kendall to hear: you can do arts, you can choose, we'll still love you regardless, you don't have to be Warren Buffett?

Kendall Warson: This is like my therapy session. I think I wouldn't be doing this if that were the case. I think I would have felt more comfortable. And to be a founder, you need to be uncomfortable. One of my good friends always asks, what are you mad at? And that's what really catalyzes innovation and grit in times when things are tough, when you're building something. So in a lot of ways, I'm really grateful that I had an uphill battle when I was a kid. For me, I saw it as an uphill battle. I don't think my parents did. But to declare, "I actually think I'm going this way, and you guys want me to go that way": I learned how to make decisions and how to be my own person at a younger age. If they had overly supported me, I probably wouldn't have taken it as seriously as I did.

I was really focused in college. I still partied and had friends, but I was the number-one student in my class, and I had a full-time job at my dream company while I was still in school. By the time I was 23, I had lived the whole life map I'd drawn for myself. I wanted to go to Parsons, I wanted to work at Marc Jacobs and Diane von Furstenberg, I wanted to be this famous fashion designer. And I was at Marc Jacobs and Diane von Furstenberg. I did it. I persevered. And I was young enough that I'd hit this amazing chapter break and realized I had a whole other chapter ahead of me. What do I want this to be about? Do I want to stay in fashion, or should I do something else in art and find my own path in entrepreneurial pursuits?

I just think it's important to recognize that your parents give you some type of a container, but you don't need to stay in that container. You can build your own. And it's helpful sometimes if you're in the wrong one when you grow up and you have that friction, because it makes you a stronger person.

Shamil Malachiyev: That's what I see from talking to founders. In my career, 90% of what I do is have discussions with various founders about their startups. And what I've noticed is we have very similar trauma, very similar things that build the grit and the perseverance. Most of us have learned to lose the blame toward our parents for not giving us everything we wanted as children, and that allows us to be okay with this level of stress and responsibility. And looking at your story, I can see you've combined the two. You wanted art, they wanted business. Your sister went business, VC. And you combined the business acumen and the art inspiration to create Cohart.

Kendall Warson: Ultimately, if I think about it now: in design school I was a leg ahead of other people, because I had the business sensibility from my parents. I kind of had both educations in this Venn diagram ingrained in me at a really young age. And now I feel like I'm uniquely positioned to address this opportunity specifically because of my own personal background, my backstory. If I was too artsy, I probably wouldn't do it.

And you see the flip side. A lot of people have tried to democratize art collecting with these platforms, and the people aren't from the art world at all. They don't understand the dynamics of the market. I've seen three cases of companies where these guys get to a point of financial freedom, they've been in consulting or banking or some industry where you can make a lot of money, and then they start to collect, and they're like: collecting's hard. I'm going to change it. I'm going to build this art platform that democratizes art collecting. We've seen it multiple times. It just doesn't work, because people assume all you have to do is stick a JPEG and a price point online and that's democratization. It's not how people buy art online, and it doesn't work that way.

So it's been really powerful for me to be formed the way I am as a human. What I'm doing is such a personal experience and a personal pursuit. And it has to be, because it's so challenging. You need to be fundamentally a little bit crazy to really go after something and try to change this old, antiquated market on your own or with your co-founder. You have to believe it's possible and that you're the person to do it. That's the founder story you have to wake up breathing and living every day. That's what will make you successful, because you'll persevere and get through all the challenges and catalyze the opportunity.

Shamil Malachiyev: It's interesting, because what you're currently doing almost looks like you're helping that younger Kendall combine the art and the business. Your platform goes to the people who do art, and business is hard, and it's like: this is how you do business. This is how you combine the business aspect with it.

Kendall Warson: Totally. And that's something I've done a lot with my executive coach. What's it called, EFT or something. It's when you recall moments from when you're younger, and you're able to be compassionate with that younger self and understand that the behavior you're carrying forward isn't something you need to hold on to anymore.

That was really helpful for me with fundraising, because you're in your own head and people say no, no, no all the time. And it kind of takes you back to these moments where you feel inadequate, where you feel like you couldn't do it as a kid. You have to learn how to be with those versions of yourself and let go of the ones that aren't relevant to you anymore. I think that helps you decipher what information you take in from other people, because everyone just has subjective opinions. That doesn't mean what you're doing isn't valuable. But in your head, it can start to feel like that over time.

Shamil Malachiyev: Yeah. "I'm not enough." Every no lands as: yes, of course, because I'm not enough, I don't deserve this. Part of why I love this game is that sometimes you have to work on yourself to transform yourself. Take cold outreach. It seems like something incredibly uncomfortable to do. You put yourself in such a vulnerable position. It ties to a lot of things: I'm scared to be seen, I'm scared of receiving a no, am I enough? How did you go through the transformation where the business requires it, you just have to do it, and it's also an incredible opportunity for personal growth?

Kendall Warson: The long story is that after my first chapter break, so to speak, mid-20s, I quit the startup where I was the first employee, and I had a little bit of an identity crisis, a quarter-life crisis. I had been pursuing this thing, I told my family I was going to do it, I was kind of angry at everyone, and I did all the things. And I didn't really feel better. I didn't hit nirvana. I thought: what is this? I just worked so hard, I pushed up this mountain, I got here, and now what?

So I took some time to reflect and do some inner work for about eight months. I was consulting. I had my own LLC where I would help people build websites. I'm really good at visual design; I can do it in my sleep. So I would make money doing that a couple of hours a week, and the rest of the time I spent reading. I went to this retreat center and worked there for a little bit. I was able to decompress from that first chapter of my life and figure out: why was I angry? What was I going up against? And that ultimately was me becoming a human and understanding what my path was. I released a lot of the blame, like you talked about.

I got to the point where I was looking ahead, thinking about building a company, and it just kind of hit me. I met Shyevin, I saw that opportunity, and it all crystallized and catalyzed in a way that felt very different from that first chapter of my life, when I was in this battle going uphill. This was more like I was being called. It felt like it was flowing through me, very organic and natural, which was really cool. A lot of the dots were just connecting for me.

And I knew it was going to be hard. My sister has really been a guide for me in the whole experience, and she said: Kendall, you should probably go work at Google for a little bit, or go to HBS, get an MBA, build up a network, because to be a founder, you really need a network to get this thing to go. And I was like, yeah, screw it. She said, not everyone knows what Parsons is, or Marc Jacobs. She was so right. We went out to fundraise and: okay, we don't have anyone to talk to. We're not going to have a mentor we can call up who'll introduce us to the right pre-seed investor. But I knew there were workarounds. We were just going to have to work harder.

We've pitched probably 400 plus, maybe 500 investors. It's been insane, because we started so cold without any type of connection. And we're doing something that isn't a traditionally sexy, venture-backable market. There hasn't been a billion-dollar exit in the art space, so people look on Crunchbase and go: eh, not a lot of comparables here.

So we went out and joined all of these founder communities. A lot of them have directories with experts and mentors, and I would contact basically every single person who had "investor" anywhere in their bio, and specifically targeted people of color and women. I said: hey, I'm an underrepresented founder looking to connect with underrepresented investors. Can I talk to you for 15 minutes? And that worked really well. It opened up a lot of doors to conversations with total strangers. Some of them went very south, and some people were very mean to me. But a lot of people would end up saying: Kendall, I think you have an infectious passion here. There's something here. Let me introduce you to my friend. And it was this chain: one person introduces you to another person, then another. All of a sudden you're on the seventh link of that chain that came through one cold outreach, and you get your first $50K investment. Like Steve Jobs said, you can't connect the dots looking forward, but looking backwards, that worked because of that first conversation I had.

So I learned to be extremely generous with my time. That's something I have as a core value now, and I work on being really generous with people who are looking to connect with other folks. That's not what you're taught. You're taught as a founder to be really efficient and hyper-prioritize. And generally that's just not what served me in opening up doors. The kind of random conversations I've had with people, listening more than talking, being really generous, this sort of abundance mindset, has been what shaped and catalyzed those moments.

We met our lead investor because someone recommended I speak to this engineer, and I thought: we don't really need an engineering person right now, we have a lot of engineers. My co-founder asked, why would you take that call? But I get on the call, I talk to him, and he says: you know what, I really should introduce you to my friend who just got back from Art Basel. I meet his friend, who's a partner at this fund, and he ends up leading our seed round. If you're being hyper-efficient with your time, and I do think that's important, you miss those. There's something about human generosity where, if you're really open and seeing the dots connect, there's just more opportunity and luck that comes your way.

So I try to remind myself of that with cold outreach. As you know, it's really hard, and people are inundated with information online today. But there's a way to craft a message that resonates with folks. You have to hit the right note where people are open and think: okay, this is interesting. I'll give this woman 10 minutes of my time. And then you really try to capitalize on those 10 minutes, and it can open up tons and tons of doors.

Shamil Malachiyev: How do you go about that structure? For all of the founders now thinking: that's interesting, I'll try it.

Kendall Warson: I actually think it's something I'm very good at now. I've gotten to the point of crafting this as a skill through a lot of trial and error with investors. That whole underrepresented founder, underrepresented investors approach is what opened up and created a network for us on that front. And cultivating the network is just as important as catalyzing it: giving those investors updates, keeping a Rolodex of everyone's names written down and how you met them, following up and saying thank you for introducing me to this person. Going back to those people is really, really valuable, because it closes the gap and builds the circle around you, and it keeps getting stronger and stronger.

With cold outreach now, we're obviously less on the investor side. We're doing it more for our go-to-market, and a big unlock for us has been art fairs. Art fairs have this whole stratification system, and you want to get to the tier one, but you kind of have to start at the bottom and climb up. And it's really interesting being a startup, because you don't want to come out and say, we'll sponsor your fair for a hundred K. We don't have that money. So you have to pitch this really creative partnership approach, where they feel like they want you to be at the fair, and they want to introduce their galleries and their artists to you as a distribution channel.

So we have really leaned on content, as I know you do too. We would reach out to the fair directors on Instagram and LinkedIn and basically say: we'd love to have you be a thought leader, someone who can share your insights with our community. And it's genuine. These fair directors are at the forefront of the industry, and like most people, in this conversation right now included, people want to talk about their own experiences and they want a platform to grow their own brand. So that has, maybe 85% of the time, opened up doors and positioned us in a way where we can end up being partners for these fairs versus being sponsors. We've used that across many different paths.

You sort of have to start with giving something before you expect to receive something. And I think you have to play to people's egos a little. You have to make people feel special and heard. If you're able to do that successfully, they'll identify you as a friend versus this person in their ear who wants something from them. So again, it's going back to being generous: with your time, with your ask, with your give. Think about receiving that message: what would you want it to say? A lot of founders aren't thinking like that. They just think: I have this product, of course people want to use it. Maybe they do, but they're not going to pay attention to you until you really warm up to them and they see you as someone they can trust.

Shamil Malachiyev: And I think this is something a lot of founders don't understand. They only look at the startup as business metrics: users, revenue. But in reality, we're all humans. We each have 80, some 100 years of life here, and whatever we do, in the end it's not going to matter much. But we have the opportunity to play this game any way we want, with so many people playing in this sandbox of a world. If you allow yourself to be that kid with excited eyes, trying to learn what other people are playing, it makes it easier to reach out, to be more curious, and to treat everyone else as human beings first.

Kendall Warson: Absolutely. And also, drink your own Kool-Aid: talk to people when they reach out to you, too. I try to be really thoughtful when founders reach out about investor connections, and sometimes it's like, oh, I have to spend 15 minutes writing this introduction. But there's something about that generosity where you just can't understand how it's going to come back to help you, but it will. It compounds. There's something underlying our human experience that rewards that type of behavior. And I think you really need to lean on that as a founder, because again, it's an uphill battle and you need as much tailwind as you can get.

Shamil Malachiyev: What do you think about the role of luck in the world? What do you think luck is, and how do you maximize your chances of getting lucky?

Kendall Warson: There was a really interesting study, I don't know if it was in The New York Times, where they were looking at people who identify themselves as lucky or unlucky, and they gave everyone the same quiz.

Shamil Malachiyev: The newspaper one. I heard the one with the newspaper: count the pictures.

Kendall Warson: Yeah, exactly, the newspaper. As you read the newspaper, the people who actually read it picked up on the messages that said "this is part of the experiment". But a lot of people skimmed through it, the ones who consider themselves unlucky, and they weren't looking for that sort of hidden message.

To me, that's very true. A lot of people identify as being kind of a victim, like the world is against them, and they're waiting for things to come to them. Versus people who are looking for opportunities, really reading the fine print, immersing themselves in learning and connecting dots between other people. Those are the folks who are lucky. But I don't know if it's this magical thing. I think it's just that you bring this energy to the world, people are excited by it, and it opens up more doors.

My grandpa always said: you make your own luck. And I kind of think it's true. If you work harder than other people, and you show up for other folks, and you go above and beyond, like writing a handwritten letter, those types of things have a profound impact on how people see you as a human being. I have a really good friend who just asked me to be her bridesmaid, and she put the "will you be my bridesmaid" in a fortune cookie and took me to dinner. I felt like I was getting proposed to. What an amazing way to ask a friend. I'll just never forget it. I was so touched by it, and it was so thoughtful.

And she's someone who, I think, looks like a lucky person on the outside. She's happy, she's joyous. It seems like life comes easy to her. But she wakes up every day and goes for a run, and she chooses to be happy and chooses to be positive and optimistic. She's always trying to see the opportunities and the connections. The way she got her job at the VC firm she works at now: she was the chief of staff at another fund, writing newsletters for their community, and one of the newsletter submissions was a role at this new fund. And she thought: I was going to put this in the newsletter, but can I just apply for it? She's like, I'm just going to do it myself. And now she's a partner there. She didn't go to HBS or Stanford. She went to a great school and worked really hard, and she just persevered. She found a good opportunity and a path, and she took the shot. To me, that looks like luck on the outside. But it really comes down to hard work, believing, and just having hope and faith that the dots might connect in a way that's favorable.

Shamil Malachiyev: It's the same in my mind with what people call high vibrations. How do you get yourself into that state? It's all about the state of mind, because as your grandfather said, we create our own way of approaching the world, and that shapes how the world sees us and reacts to us. Physicists look at the universe and it's all waves, it's particles, there are fourth and fifth dimensions, and we don't understand how this works. But there is something about our attitude in terms of what we attract into our lives, the way we feel and think about things. And there are still a lot of times when we fall into being victims, when things don't go our way. Everybody has that every once in a while, and usually it's when there are just too many responsibilities, because when you're in a victim state, you don't have to deal with responsibilities. Did you find any good ways of picking yourself back up, getting back in the saddle, during those times when it feels like the world's against you?

Kendall Warson: That's a good question. Well, first, I think it's a muscle. The first time you get knocked down, it hurts pretty bad. You're sort of banged up a little bit. Now, when it happens to me, my recovery time is so fast, and I almost kind of laugh through it, because I see it happening. But in the early days, it just hurt. People reject you, say kind of mean things to you: why are you doing this? Or you think you're going to get to a yes, and all of a sudden you get a no. You're on your tenth meeting, you thought it was locked in, and it just goes out completely. And especially with fundraising, it's like someone is punching you in the face. It's just so painful.

In the beginning, I would talk to my sister, and she would just say: I told you it's the hardest job. You feel kind of stupid complaining when you realize, okay, I'm trying to do something that's really hard. And I have some very funny stories, especially with fundraising. I would watch the Arnold Schwarzenegger videos where he says: when you hear no, you have to hear yes. He gives really good motivational speeches. I would just be on YouTube at night by myself in bed, like: okay, just start to hear yes when people say no. And I kind of rewired my brain a little bit, to the point where if someone shuts me down now, I kind of think they're crazy. It's weird. I sort of believe they're missing an opportunity. I'm not going to let them get me down.

So that's how I think about it now. If I get punched in the face now, it hurts less, and I'm able to get up much faster. It still happens all the time. Every day I have a high high, and I always have a low low as a founder. And whenever I have a big one, it can happen in my personal life too, I try to really weather the storm and stay kind of calm. I do a lot of stuff for myself. I run a lot. I play soccer four times a week. I journal, I meditate, I do a lot of breathing exercises, I walk my dog. There's basic stuff like that that really does help you keep a stable nervous system, which you need in order to stay sane, and in order to get back up after you've been punched.

And I also kind of let myself feel it now. When someone really does say no, or it's just a tough day, I'm just like: okay, fuck. Let it happen, feel it, and just be okay with it. It's hard. What can you learn from this experience? How can you grow? Let yourself process it a little bit. Don't try to just shut it out immediately, or go drink, or try to make yourself feel good all of a sudden. Just feel it for a little bit. It makes it feel less scary and less intense, when you realize: okay, that was something that happened, and it doesn't have to take up a huge part of myself. The more you look at something, the more you give it attention, the smaller and smaller it gets, if you don't want it to sit within you anymore. So I try to treat that as an introspective thing, in order to stay sane and keep going and not be affected by all the nos.

Shamil Malachiyev: Sometimes I think of what's called the internal family systems idea in psychology, where you kind of have this little baby. I have a baby Shamil who I just have to pick up and say: just cry, it's fine, we'll get to it, I'm here, the leader's here, we'll get through it. It's okay to spend an hour just feeling like shit. And sometimes I'd have a low-motivation morning. I envision this version of me going to the gym straight away, sitting down at the table, doing a podcast, having the internal team meeting, meeting with three clients, doing everything, still having a lot of time, looking at my partner and thinking: how do I make her happy, do this one small thing. And I'm lying there thinking: it's so easy, everything is right there, I know how to do it. What is stopping me? Why am I not doing it?

What I found for me is, as you said, a muscle. First thing, I switch off thinking. I'm that person now, in that moment. Grab my gym bag, regardless of how I feel, put the shoes on, hop in the car, and I'm in the gym. Next, come home, coffee, sit down at the computer, delete anything distracting, games, anything, and do a bit of work. After a while, it's like you've changed into a completely new person. Is that the way it worked for you too?

Kendall Warson: Yeah, completely. There's such a big difference between thought and action and how you're feeling. And the thought piece can go in circles sometimes. Oh, I have to do my board deck. Jeff Bezos said the easiest way to be stressed out is to procrastinate. If you just start a little bit, if I just take some bullet points on my phone about what my deck's going to be about, I'll feel way better. It's little steps: taking action, going outside, going for a walk, putting yourself in the mode of doing the thing. Sit down at your computer, get rid of the distractions, and then it kind of flows. If you're in bed just sulking, of course you're not going to want to go to the gym. But you put on the outfit, you go get your gym bag, and that helps you get things moving.

That's why soccer has been really helpful for me. So often I'm just so tired. I always play at night, and you've had this long day, and you think: I don't want to go run around. But then you go out there and you put on your little shin guards, and somehow you're just in this uniform, you're off your phone, you're totally disconnected, and then you feel so much better. It's really important to just get over that hump when you're in your thoughts, when you're kind of running yourself in a circle. Put on the outfit, take action, and generally you can get out of your own head pretty quickly.

Shamil Malachiyev: You've also mentioned meditation. How does that happen for you?

Kendall Warson: I've had an interesting journey with meditation. When I was doing a lot of the inner work and working at the retreat center, I was in this tiny house, and there was no technology. I was off my phone, doing a lot of meditation and processing and reading. And there was this guy at the center I would ask questions, and he would answer my question with another question, which would just spin me up.

I think of it like a muscle. I really learned how to meditate there. And when you're meditating, it's the stillness. A lot of people are really good about routine and habit. I'm not a habitual person. I like the diversity of every day. I do go for a walk every morning with my dog, and I play soccer. Those are my two things. But I have a different coffee order most of the time, I wear different outfits. I like to have nuance in my day. So for meditation, I'm not a sit-down-at-3-p.m.-every-day person. But I will notice when I'm overwhelmed or feeling anxious, and I'll know I need to spend 15 minutes completely silent and meditate, essentially. And I'm somehow able to access that same headspace of being in that retreat center. My pool is so deep now, because I really carved this deep pool, and I can just go straight there. I pop back out, and I'm good. So I don't think I have a normal relationship with it. It's just something I'm able to access if I put myself in that position and lock in. And it's really helpful and healthy for me as a mechanism to recenter and get grounded.

Shamil Malachiyev: If I look at two complete opposites: there are people who are extremely creative from childhood. And then, something I saw studying in England at an international college with a lot of kids from China, first-place nationwide mathematics Olympiad people, there are those who are very structured. Everything has to be disciplined: what I do, when I do it. I would always find that so hard. For me, if everything in your day is structured, it's almost like: what's the point of living? You know exactly what it's going to be like for the next 60 years. There is no life in it. But at the same time, you're trying to build a business, which is something very structured that cannot operate in complete chaos. How do you force yourself into structure when you need to?

Kendall Warson: I think everyone is different. Everyone has their own approach to what structure looks like. I grew up with a lot of structure. I am someone who is very disciplined naturally, so I don't need as much of a push to get in. And I'm also so passionate about what I'm doing that if I start, I'll work for six hours straight. So I actually need more structure around release of energy, more structure around non-work, because my default is to work 24/7.

My structure is: on Saturdays, I don't work. I don't look at my computer. Sundays, I'll work for a couple of hours just to get caught up for the week. And I'm very serious about walking. I walk at least 10,000 steps a day, and even if I'm on a trip, I'll walk in circles around the airport. I need it to clear my head. I also have a lot of structure around talking to my family. I try to call my parents at least every day or every other day.

And that has actually helped create more focus within my company, the more I'm focused on myself and on my health. Ironically, every hour I'm not walking or playing soccer or talking to my family, I'm mostly doing Cohart. I think that's inevitable as a founder: so much of your time, so much of your energy. The hard thing is just not letting it absorb your whole life. It's almost better to have some boundaries around your personal life and your health that keep you sane and keep you focused on feeding the engine itself that's building the company.

Shamil Malachiyev: When you go for walks, is it mostly music, podcasts? What do you listen to?

Kendall Warson: Total psycho. No audio at all. It's just me and, I mean, I live in New York, right? In Brooklyn there's so much stimulation, and I just love being outside. I love seeing the cars, hearing the sounds, seeing the birds, walking over the gross trash. It centers me to be very present. And I try to do no audio, and it's totally changed my life. Something about walking processes a lot of thoughts for you, so you come back and everything feels distilled. Whenever I'm feeling anxious, it feels like everything's clustered. It's tight, it's stuck. And walking somehow dismantles it all and makes it feel like a pond again, a still ocean, which is the state I'm always trying to regulate toward. And everyone's different. Some people need more activity, some people need less activity and more reflection time, more journaling, talking to friends, more social time, more alone time. You just have to figure out what your formula is to find that equilibrium.

Shamil Malachiyev: What are you most excited about right now?

Kendall Warson: I'm really excited about where our company is. We have the first semblance of product-market fit, where things are working, people are now paying for the product, and we have recurring revenue. It's really exciting. Every day there's something. Yesterday we just had the first $70,000 sale processed through our invoice system. We're kind of a pass-through on transaction volume, we're not really making revenue off that, but it's a signal that we're getting high-quality businesses to use the software, because they have high-value sales. And we also now have fairs approaching us that are tier-one fairs in our world.

So for me, it's a really exciting time in our business. We've figured a lot of things out through trial and error. And I'm really excited about how I've grown as a person throughout the experience. I'm really proud of myself, and I'm really proud of my relationship with my co-founder, with my team. We have so much opportunity ahead of us. And I think it's important to take stock and to recognize and reflect on how much you evolve throughout this experience, because you have to reflect in order to catalyze the next wave forward. I'm kind of in that state now, where it feels like a really great shift, and I'm fully showing up for it. We're all 110% there and excited to carry things forward into the future.

Shamil Malachiyev: I feel like you'd be an amazing performance coach. The way you've gone through the transformation: a lot of people I talk to are still struggling in a way, deep in the work and the stress, without having the opportunity to understand who they really are and to grow from the place of: this is what I love to do, and this is what I want to do.

Kendall Warson: It's very different when you're digging down versus being pulled up. It's a different feeling. It's like trying to exercise when you're in shape versus not in shape. It's painful trying to run when you haven't run in a while, and when you're in shape and you're running, it feels like it's flowing through you. So I think a lot of it's muscle at the end of the day. You've got to get in the zone of knowing that you're growing with the thing that you're building, and it takes time. It's not going to happen overnight. But you've got to celebrate the wins and celebrate the milestones. And then, whenever you get punched in the face, just get back up and keep going.

Shamil Malachiyev: I want to thank you so much for taking the time today, because I know you have a very busy day. I hope this is not going to be the last podcast we do together, because there are a lot of interesting parts of your journey that I would personally, selfishly, really like to explore further. Thanks so much for taking the time.

Kendall Warson: Thank you, Shamil. It's great to be on with you, and I'm really excited about what you're building with the podcast, and honored to be part of it.

Shamil Malachiyev: That was a really good conversation.

Kendall Warson: Thank you. You're a great conversationalist, and you led the conversation. I didn't think it was going to go that way at all. I was reflecting on it myself, and I actually learned a lot from talking through some of those things.

Shamil Malachiyev: Because it's always different, and I like to not keep a tight structure and just go with the flow. The best conversations I have are usually with founders I've known for five, seven years, where we go really deep, because we've all done some reflection and really understand ourselves. And I really felt that in conversation with you too. A lot of times it would be really hard to go into the depth of what it takes and what transformations are required. With you it was absolutely fantastic. Not only have you been there, you've grown from it, you've transformed, and now you're using that to propel yourself forward.

Kendall Warson: You kind of have to. Otherwise, I don't know where else the energy comes from. Thank you so much, Shamil. It was awesome being on with you, and I really appreciate you inviting me on.

Shamil Malachiyev: Thanks so much for being generous with your time. I wish you all the best with Cohart, and I'll continue following your story. Have a great soccer practice, and an amazing wedding coming up too.