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You're listening to the Travis Makes Money podcast presented by GoHighLevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet, just go to gohighlevel.com travis.
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What's going on everybody? Welcome back to the Travis Makes Money podcast where it's a mission to help you make more money. Today on the show I'm talking to my new friend Chris Kaufman. Chris is a Detroit based creative leader, entrepreneur, investor and author. As co founder and former chief creative officer over at StockX, he helps scale the marketplace to its $3.8 billion. That's billion with a B $3.8 billion valuation serving customers in 200 plus countries, which I don't know if you know how many countries are in the world, but that's like all of them. So 200 plus countries and territories. In 2020 Stock StockX reported 1.8 billion in GMV and 7.5 million plus trades. Chris, the bestselling author of Empathy at Work and advises and invests in early stage companies. His work blends brand building, culture, design and practical empathy to help leaders build high trust, high performance teams. Chris, what's up dude? Welcome to the show.
C
Hey Travis, good to be here.
B
So you are entrepreneur through and through and now you are an investor and really advisor, somebody who breathes the entrepreneur spirit and helps other people do the same. Where did this start for you? What was the first time you ever made a dollar that got you really excited?
C
So the very first time was when I got a paper route when I was 10 and a couple things about a paper route and I obviously their paper routes are not what they used to be, but for me it was really one of the first places where I had to learn serious time management, had to learn some discipline because you go to school all day and then you get home and there's a stack of papers on the porch. They're not assembled, right? Like you gotta assemble em, you gotta pack them, you gotta bag them and then you got to get them in saddlebags on your bike and go around the neighborhood and deliver them. And then at the end of the month you go around the neighborhood and you knock on every door and you collect $3 for the paper. And that's, you know, that's what it was back then for the month. But you know, a couple things you learn is one suddenly like you're the only 10 year old in the neighborhood, a neighborhood who has money, which is kind of a fun spot to be in because then you can start buying things. And when you're 10, you know, I'm buying baseball equipment and football equipment and, you know, stuff that 10 year olds wanted. But it, you know, it was the first time that I really learned, like, how much work goes into making a dollar. When you're delivering a newspaper all month and it's $3 per house, you're certainly not getting that whole $3. Right. That's part of that goes to the publisher and they got to cover their costs. I mean, you're probably walking away with a dollar of that one. You learn how much labor goes into that over the course of a month, whether that is in this outside of Detroit. So whether it was 12 inches of snow on the ground in the middle of January or 95 degrees in the middle of July or August, you had to get out there and deliver the papers. And then come into the month, you realize how hard it is to collect $3 from people and you really start to appreciate what goes into it. And like, you know, people see you out there, they wouldn't answer the door. You'd have to come back multiple times. But it was also probably the first time that I had a moment that was like, there has to be a better way to make money than this because it was a lot of work for not a ton of money.
B
Yeah, you know what, that's the, the first taste of freedom, the first taste of making a little bit of money. When you, when you start looking at what you did to make the money, that. That's exactly what happened with me, man. I was like, I was doing landscaping as a, you know, teenager. That was the same thing. It's like you put in all this, this, this labor, these actual manual labor hours, and then you look at how much money that you made and it's like, God, that's gotta be. I gotta, I gotta figure out a better way to do this. It seems like. Seems like all these people that have a bunch of money aren't out here, like mowing lawns every day like I am. So there' a better way to do this. Did you, did you feel like you caught that entrepreneurship bug at that point, or were you kind of heading toward a traditional career path? You know, high school, college age?
C
I mean, I probably started to catch a little bit of the itch at that point. You know, I did that for a few years. And at 10, you're not necessarily thinking about scalability of revenue and things like that. But, but there is a part of it where you kind of start to look at other People making money and how they're making money and what is scalable and ultimately what's that thing that you can do where you're going to make money in your sleeve. And over time you kind of start to think about that. I think one moment where I kind of had that first aha moment around entrepreneurship, starting a business, not necessarily scaling something, but like having really significant upside on something was in high school. And I, I will preface this with I was not the kind of kid who would ever have a fake id. Like I was in art club and physics club and one of the editors of the school paper. I was like working on a school paper till like 7 o' clock at night and all kinds of other things. But there were a lot of kids that I went to high school with that were the kind of kids who wanted fake IDs. And, you know, this was mid-90s. There weren't a lot of kids who had a copy of Photoshop and there certainly weren't a lot of, you know, 14, 15, 6 year, 16 year olds who were good at it. But I was, and other kids figured this out. Especially as I was doing things, you know, like the school newspaper and, you know, working on computer graphics and art class. I, it, it came to someone's head that was like, hey, could you like put my face on an id? I was like, sure. Like, that's true. For what?
B
Yeah.
C
Which spun into this thing which was like, I can, I can make these IDs, I can charge people for them. I mean, it was back when it was just a laminated card. So I had like the, you know, Gateway 2000 computer and the Epson inkjet printer and a refurbished laminator. And I was making these kids at high school IDs for 50 bucks a pop. And it probably took me 10 minutes to make one. And I think that was the first moment where I was like, this probably isn't a long term sustainable business, but there are better ways to make money than delivering, you know, papers and sweltering heat or frigid cold.
B
Yeah, yeah. So high school age, still hustling, still always got something that you're working on. What did that translate to post high school?
C
Well, you know, then I went into undergrad and I.
B
For business or entrepreneurship or no.
C
So I did my bachelor's degree in fine art, studio art with a graphic design concentration.
B
Okay.
C
I was always in.
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interested in art and design. And I think in, in the 90s when, you know, it was like this perfect storm of the intersection of fine and conceptual art with the rise of the computer and computer graphics. And it was these two things that I fell in love with that I could, you know, really like meld together.
B
Yeah.
C
And I, I was just super interested in that. And I, you know, I went down that path and originally thought that I might go into advertising or something and then decided that that wasn't for me. But like having a, like the entrepreneurial itch. In college, there was, you know, there was even a part of me that was, you know, like when I made projects, I was making them for like through the lens of how does this apply to business? Is this scalable? Does this have commercially applicable use? I think I was thinking about these things from a different angle than some of the other people who were just kind of in the art school to become artists. I really started thinking about how art and business and design intersect at a relatively early age. And more importantly started thinking about how can you use design as a business discipline to solve problems, create businesses, drive revenue, and ultimately build teams and create products that customers are interested in using. And design is such a big part of that.
B
So after undergrad, did you get a job, like bridge the gap for us between college and StockX?
C
So in college I, you know, like, I worked pretty much full time through college. I did a lot of freelance work, a lot of, you know, picked up design projects. And then while I was finishing college, I landed an internship at Quicken Loans. And I was supposed to be working on like UI UX research projects, kind of facilitating focus groups, doing one on one interviews. And what happened pretty early on was I was facilitating some of those interviews, sitting in on some of them, observing, taking notes, kind of hearing about where customers were getting stuck, challenges. They were having things that they were encountering in the mortgage industry that they absolutely hated. And this was 2006, so the iPhone did not exist yet. There's no such thing as apps really. But some of these processes were starting to come Online. And Quicken was a pioneer with that. It was something that Dan Gilbert felt really passionate about pretty early. But I would go through these user tests and instead of just taking notes and saying these are things people are struggling with, I would go back to the computer and I would create a design mockup that solves some of the problems. I might look at one of our landing pages or our emails and say, okay, we heard this feedback. What if we change these things? What if we move these buttons? What if we made this flow more clear? And it wasn't long before someone on the marketing team there said, wait a minute, would you rather just do product design stuff like work on the website and the landing pages and the emails and the blog and all these other things? We could use more help there. And you seem to understand that side of the business. So, long story short, I hired on as interactive design director right out of my internship, had just finished undergrad. And, you know, that was a place that give Dan a lot of credit, especially in the early days, like, very nimble, very entrepreneurial spirit. People had a lot of autonomy, they could take risk. And what happened was I was working on a project with a couple other people internally that was called Quizzle. And it was essentially, we created this credit report score financial management tool basically to get people mortgage ready. Because we were throwing away a lot of mortgage leads because people's DTI was slightly off, their credit score needed to improve by a couple points. And instead of throwing those leads away, we decided, what if we could incubate these people? Some of these people are like three points away on a credit score from qualifying. You know, let's, let's give them some pointers, let's help them consolidate debt, get the mortgage ready. So we, we end up spinning that out into its own companies. You know, stayed within the Quicken family of companies, did that for a few years, and that ultimately got acquired by Bankrate. I ended up doing the agency thing after that for about 11 months. And I confirmed my suspicions. I was not built for the agency world. I, you know, I didn't really want to do client work on that level. I love doing client work now because I get to pick clients that I actually love the work they're doing and I like working with them. It's a way more personal process. But, you know, something about like big agency client work was not for me. Which then led to starting another business called up to that. Essentially it was an idea around creating a social calendar for iPhone and Android. You know, at the time, everything in the social landscape was either past tense or present tense. So you were, you know, you were on Facebook, you're on gowala, you're on Foursquare, you were talking about the things that you were doing right now or the things that you already did. But there was no future tense social platform to plan the things that you wanted to do with your friends. So, you know, our idea was something future looking. You'd talk about the things that you'd be doing tomorrow, this weekend, next week, and you could actually make plans around that. And, you know, we did that for four or four and a half years, got up to a couple million active users. Never really hit a point of saturation, but, you know, Dan was our biggest investor in that too, and.
B
Really?
C
Yeah, and you know, like, he, he kind of stuck with the things that we were building over the years, which was, you know, super cool. And, you know, he, he knew these teams well, and I think he had a lot of trust in, you know, what we were doing from a team perspective. We, we didn't always have the product idea figured out, like, things like that. But yeah, so I would say, like, team is so important. But, you know, long story short, we got to a point where growth had plateaued. We started shopping the business around. We, you know, talked to a bunch of the big tech companies, you know, looking for an acquisition situation. And ultimately Yahoo made us an offer to acquire the company. We were ready to move to the west coast, and a couple days before that deal was supposed to close, Dan asked to meet with us. And he basically said, hey, the Yahoo deal isn't sitting right with me. You're Detroit guys. You told me you always wanted to be here creating jobs, building businesses, helping revitalize the city. How the heck are you going to do that in California? We said, well, we're not, but Silicon Valley acquisition looks pretty good on a resume and we're kind of out of money and we got bills to pay. And he said, you know what, like, tell Yahoo the deal is off. Show up here Monday morning. You guys can have a few desks outside my office and you can start working on something else. You build it, I'll fund it. And during that conversation, which, you know, we were back to, back to back startups at this point. All of us. Yeah, we didn't necessarily have another startup idea. You know, Dan mentioned this idea about, like, what if you applied stock market mechanics to a secondary retail market. We have no idea what that means.
B
Can you say that in English, please?
C
Yeah, whole idea like that, that's that's all I've got. But I think you guys can figure it out. And for some crazy reason we bailed on Yahoo. We showed up that Monday morning and started working on what eventually became StockX.
B
No way. That's crazy, dude. I mean props to somebody like Dan, dude. I mean like that speaks volumes for like the type of leader that, that, that he was to be able to just continually like even even though it wasn't like in direct benefit to his core business, you know what I mean? Just seems like something like somebody you want to get around. Which is I think when, when, when younger people, because we have a lot of younger people listening to the show ask for advice around like, well, what should I start doing? How should I start making money? And it's like I tend to push back against this idea of like really, really early entrepreneurship anymore the more that I've been around a lot of other people because of stories like this, because I hear like, could you have just like gone out as a 22 year old and started a company and could it have been successful? Yes. I'm not pretending like that is a path that's not available. However, like the volume of learning that you were able to do on somebody. This episode of the show is brought
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El's dime. While they were paying you to learn from them in a exponential way is. Is so much more valuable in your 20s than it. Than it is sometimes to just go start your own thing. I think it's wildly underrated because of the glorification of entrepreneurship that's happened in the last couple of decades. But I also just love that story for so many reasons. And that's one of them to me, is that you're able to just get aligned with somebody who is really smart guy, making a lot of big moves already really successful, and then saw something in you guys enough to be able to just say, I just want you to work with me. I want you to continue working with me. Doesn't matter. Like, money is off the table. Whatever it takes, like, here's an idea, run with it. And then it actually turns into this, you know, $4 billion company.
A
So.
B
So at the time when you started it, what did it was. Was collectibles sort of on the horizon? Like, what were you thinking in terms of what's our. What's our, like first go to market on this?
C
So we looked at all kinds of things that sold for a premium on the secondary market. And now these are products that people are passionate about. They're made in somewhat limited supply, they have high demand, they sell out quickly. And then you have the price premium that comes with that. So we were looking at anything that these stock market mechanics could be applied to. And by stock market mechanics, I mean transparency, anonymity, and authenticity. When you buy a share of stock on any of the trading platforms, you have no doubt that it's real. You have no idea who you're buying it from, and you know exactly what the last person paid for it. So you can make intelligent buying and selling decisions. And we wanted products where these same core tenets could apply to. So start ended up starting with sneakers. And the biggest reason we started with sneakers was because very early on we discovered that about 70% of sneakers on the secondary market were brand new in the box, which meant we could go after 70% of that market. We didn't have to worry about selling used shoes. We didn't have to worry about doing condition grading. And most importantly, if you had only brand new products, it meant you only had to have one product page for everything. One set of photos, one description. Right. People didn't have to do like they were doing on ebay and write a description. They didn't have to take photos. They literally just had to come on StockX, create an account and click a sell button and say, I have this. I'm gonna sell it for whatever the current bid is and the transaction would complete. And that, that was a really powerful part of the platform.
B
Yeah. The removal of friction.
C
Yeah, yeah. And I think, you know, like, looking forward to getting to the point where we, we did collectibles there. There were some missteps, in my opinion. So we went from doing sneakers to going into watches and bags, and then we got into streetwear after that. If we had a do over, I think we would absolutely start with sneakers. Go super deep on sneakers instead of trying to go wide as early as we did. And then the next vertical, 100% should have been streetwear. Same customer base, tons of overlap. You're marketing to the same demographic. You're just, you know, you're, you're saving and expediting so much time and resources and, you know, pulling from the same knowledge base there. And then I think we should have went into collectibles because there's a lot of overlap there, especially, you know, with supreme and Bear Brick and some of those things. It. And then maybe considered some of the other things. But we, we had this like super passionate user base and customer base. Yeah. They were already into sneakers. Most of them were already into streetwear, and many of them were all into collectibles. And I think like, we should have just went after those big three categories right away and got really good at them before we did anything else.
B
Yeah, yeah. And the, you know, hindsight's always 20 20, but I think you guys did a pretty good job of figuring it out. I'm curious, I'm curious on the sort of the, the alchemy here. Like, what, what year was this that you launched the initial version of the platform?
C
First version launched in 2016.
B
Okay. Okay.
C
So we, we started working on it early 2015. It took us about 11 months to build.
B
Okay, so do you view the. Because, you know, two, like a decade or two decades before some, somewhere in there, the timing might not have been super great because I felt like there was sort of like a lull culturally in, in the collectibles space. It was like it was really big in like, you know, the 80s or whatever. And then there was sort of like a drop in interest. And then in the last decade, decade and a half, it's, It's. It's exploded more. Do you view StockX as like, being one of the reasons for that? Just because of the, The. The barrier, the barrier of like finding them or getting involved became easier because of your platform? Or do you view that as like this, this industry was sort of taking off already and we just provide and we sort of piggybacked on the tidal wave of the collectible space.
C
Again, I think that is probably more accurate now. We were a vehicle that. I think we probably expedited some of what was happening anyway because we were giving people a tool that one gave them access. It democratized some of this market. It allowed things to move a little more quickly in the direction that they were probably going in anyway. But the timing was really important because all industries and markets, they ebb and flow. They're cyclical. What happened with the collectibles markets and trading cards especially was like you said, you had this huge movement in the 80s. You had a ton of activity. There were a lot of things on the market, but something that we never really knew was how much of certain things were on the market, especially with trading cards. You know, I think we always assumed that there were far fewer of almost everything than there really were.
B
Yeah.
C
And. And the Internet didn't exist to essentially bring transparency to this. So, you know, if I had a Ken Griffey Jr. Rookie card, I assumed that I was the only person in the world that had a Ken Griffey Jr. Rookie card because I was the only person in my neighborhood that had one. You'd go to a local trading card show, you may see a couple. It wasn't a ton. And then all of a sudden the Internet is out there and the Beckett guide is online and ebay pops up, and all these things are happening in the 90s, and people start realizing, like, there are tens of thousands, if not hundreds of thousands of some of these things that we thought there were only 10 of. And that has a really detrimental impact, not only on a market like that, but on a culture like that, because losing that scarcity takes away a lot of the desirability of those products. So, you know, fast forward to a point where StockX comes in, these markets have leveled out, and now the Internet has started doing the opposite. Where in the beginning it was really revealing that there really wasn't as much scarcity in some of these products as we thought. Now, especially with sneakers, we're finding some of these products are a lot more rare than we realized. And with some of these things they have, you know, one, they have a limited life and two, there are products that are constantly coming out of the market from a dead stock or new in the box perspective. So say you have 50,000 pairs of shoes just floating out there that are brand new in the box and they, they, you know, they have this value, value and desirability that people are looking for. Well, the second somebody puts one of those pairs of shoes on their feet, that's one fewer pair of those shoes that are in the market. And that's happening all the time. And if Nike or Adidas or another manufacturer isn't constantly restocking these things, which typically they're not, the inventory is going to go down, the value is going to go up. And with something like StockX, you're actually tracking these things. You can actually see the sales volume, you can see what they're selling for. You can get a pretty accurate idea of how many of these products are actually floating around in the world.
B
Yeah, yeah, man. Chris, I wish we had a lot more time here because this conversation is fascinating to me, but I want to be respectful of your time here. I know you just came out with a book recently, Empathy at Work. Can you give us just a 30 second overview of this? Where can people go get that and then we'll get out of here?
C
Yeah. So it is really a culmination of things that I learned over the course of my career, things I learned in one of my grad programs. I did a master of Science in learning and org change at Northwestern. And through that I started looking at all of these concepts, models, frameworks, anecdotal things over the course of my career and thought, gosh, leading with empathy is a really powerful tool. And I think there's evidence that supports that. Not only is it good for morale, but it leads to improved innovation, increased creativity, it reduces attrition, it's good for the long term sustainability of the business. So the idea was kind of put together a guidebook that, you know, brand new leaders could learn from CEOs, entrepreneurs, you know, really use it as a tool to think about as you're building teams, as you're creating team dynamics, you know, as you're figuring out what those mission, vision and values are. You can really use this as a companion guide to figure out some of those things. And also use it as a guidebook to decide what kind of leader you want to be.
B
Well, you've heard it. You've heard it from Chris, specifically on this show, of how many things that he's touched in his career, the success of being able to achieve. So empathy at work. Go pick up a copy of his book as soon as you possibly can, Chris. Appreciate you taking the time. I know you're a busy guy. Don't take that for granted. Everybody else listening. Remember, money only solves your money problems, but it's easier to solve the rest of your problems with money in the bank. So let's solve that one first here on the Travis Makes Money podcast. Thanks for tuning in. Catch you guys next time. Peace.
Guest: Chris Kaufman (Co-founder & Former CCO of StockX, Author of Empathy at Work)
Date: March 6, 2026
Host: Travis Chappell
This episode features a deep-dive conversation with Chris Kaufman, Detroit-based entrepreneur, creative leader, and co-founder of StockX. Chris recounts his entrepreneurial journey from childhood hustles to founding a multi-billion dollar marketplace and shares insights about making money by removing friction and leading with empathy. The discussion covers lessons from early jobs, the founding and scaling of StockX, the timing of cultural shifts in collectibles, and the vital role of empathy in high-performing teams.
(01:06 – 07:08)
“When you’re delivering a newspaper all month … you’re certainly not getting that whole $3. Right. You learn how much labor goes into that.” — Chris Kaufman (02:35)
“There are better ways to make money than delivering papers in sweltering heat or frigid cold.” — Chris Kaufman (07:04)
(07:19 – 12:13) [Main content resumes at 10:34]
“I really started thinking about how art, business, and design intersect at a relatively early age.” — Chris Kaufman (11:09)
(12:13 – 19:09)
“Instead of just… taking notes…I would create a design mockup that solves some of the problems.” — Chris Kaufman (12:48)
“You build it, I’ll fund it.” — Dan Gilbert, recounted by Chris Kaufman (17:38) “We showed up… and started working on what eventually became StockX.” — Chris Kaufman (18:52)
(19:09 – 29:41)
“They literally just had to come on StockX, create an account, and click a sell button… That was a really powerful part of the platform.” — Chris Kaufman (26:24)
“If we had a do-over… the next vertical, 100% should have been streetwear. Same customer base, tons of overlap.” — Chris Kaufman (27:23)
(28:41 – 33:16)
“We always assumed there were far fewer of almost everything than there really were.” — Chris Kaufman (30:40)
“With something like StockX, you’re actually tracking these things. You can see the sales volume, … pretty accurate idea of how many products are actually floating around in the world.” — Chris Kaufman (32:46)
(33:16 – 34:44)
“Leading with empathy is a really powerful tool. Not only is it good for morale, but it leads to improved innovation, increased creativity, reduces attrition … it’s good for the long-term sustainability of the business.” — Chris Kaufman (33:40)
The conversation is candid, practical, and inspiring—reflecting both Travis’s curiosity and Chris’s willingness to share concrete lessons, not just victories but pivots and mistakes. The focus stays on actionable entrepreneurial insights, team-building with empathy, and creating value by reducing friction—for customers and for teams.
For anyone interested in unconventional ways to generate wealth, scalable business models, leadership, or the intersection of tech/design and commerce—this is a must-listen episode filled with actionable wisdom.