The Exchanges

Q So, so how did you, like, how did Zappos even get on your radar? Like, how did that happen?

A It almost actually didn't get on our radar, because I remember getting a voicemail from the founder of Zappos, Nick Swinmern, and he said he had this idea for selling shoes online, and we were getting random Pitches every day, and so to me, it seemed like the poster child of bad internet ideas. Who's gonna actually try on shoes without seeing them in person? Yeah. And right before hitting the delete button on the phone, he threw out a couple facts that made us change our mind. One was that footwear at the time was a forty billion dollar a year industry in the US. Yeah. And I'm not into shoes at all, so that was News to me. And then the other interesting fact was that at the time, mail order catalogs, those paper catalogs, that was actually the fastest growing segment of the footwear industry in the U S and that represented five percent. So two billion dollars a year and growing. And there's clear proof that people are willing to remotely try on shoes. And so in our minds, we thought, okay, the worldwide web, the internet is going to be much bigger than just paper Order catalogs, and so that's what made us ultimately decide to invest.

AI assessment note: “I remember getting a voicemail from the founder of Zappos, Nick Swinmern”

Q Okay. First of all, Tony, this is not how this narrative is supposed to go. I mean, you were so young and this is just three years after you graduated from college. So, I mean, was that totally overwhelming that, that, that, that happened so quickly?

A Well, the whole thing definitely seemed very surreal, but at the same time, What a lot of people don't know is the real reason why we ended up selling the company, and the real reason was because the company culture had gone completely downhill, and I myself dreaded getting out of bed in the morning to go to my own company, which is kind of a weird feeling, because when it was just five or 10 of us, and we were all friends, it was a lot of fun. We were kind of your typical dot-com startup back then. We were sleeping under our desks, had no idea what day of the week it was, working around the clock, but it was Really exciting, and it was fun growing, and as we started hiring more and more people, we eventually ran out of either friends or friends of friends, and so I had to do, figure out how to do interviews and, and so on, and not everyone we hired was good for our culture, and by the time we got to a hundred people, it wasn't any one specific hire. It was just death by a thousand, or in this case, a hundred paper cuts, and that's really what led to the sale.

AI assessment note: “Well, the whole thing definitely seemed very surreal”

Q That wasn't baked into the model from the beginning that came later?

A Yeah, so in the beginning, we always wanted to offer good service, but it wasn't until we decided we wanted to build our, that's what we actually wanted our brand to be about, that's the most important thing. It led us to do a lot of things that would not have made any sense if that wasn't our North Star, and so, uh, examples would be offering free shipping both ways, because that's obviously very expensive to do, and, um, You know, if we were just around trying to say maximize the profit margins, then we never would have gone down that path. And yes, we would have made more money in the short term during those days, but then we wouldn't have built our brand and reputation and so on. And so I think, you know, when, when you actually want your brand to stand for something or to have some sort of purpose, and in our case, it's about to be about the very best customer service and customer experience. You do things that are kind of nonsensical in some ways and that your competition would never do.

AI assessment note: “in the beginning, we always wanted to offer good service, but it wasn't until”

Q That wasn't baked into the model from the beginning that came later?

A Yeah, so in the beginning, we always wanted to offer a good service, but it wasn't until we decided we wanted to build our, that's what we actually wanted our brand to be about, that's the most important thing. It led us to do a lot of things that would not have made any sense if that wasn't our North Star, and so, uh, examples would be offering free shipping both ways, because that's obviously very expensive to do, and, um, You know, if we were just around trying to say maximize the profit margins, then we never would have gone down that path. And yes, we would have made more money in the short term during those days, but then we wouldn't have built our brand and reputation and so on. And so I think, you know, when, when you actually want your brand to stand for something or to have some sort of purpose, and in our case, it's about to be about the very best customer service and customer experience. You do things that are kind of nonsensical in some ways and that your competition would never do.

AI assessment note: “Yeah, so in the beginning, we always wanted to offer a good service, but”

Q First of all, Tony, this is not how this narrative is supposed to go. I mean, you were so young and this is just three years after you graduated from college. So, I mean, was that totally overwhelming that, that, that, that happened so quickly?

A Well, the whole thing definitely seemed very surreal, but at the same time, What a lot of people don't know is the real reason why we ended up selling the company, and the real reason was because the company culture had gone completely downhill, and I myself dreaded getting out of bed in the morning to go to my own company, which is kind of a weird feeling, because when it was just five or 10 of us and we were all friends, it was a lot of fun. We were kind of your typical dot-com startup back then. We were sleeping under our desks, had no idea what day of the week it was, working around the clock, but it was Really exciting, and it was fun growing, and as we started hiring more and more people, we eventually ran out of either friends or friends of friends, and so I had to do, figure out how to do interviews and, and so on, and not everyone we hired was good for our culture, and by the time we got to a hundred people, it wasn't any one specific hire, it was just death by a thousand, or in this case a hundred paper cuts, and that's really what led to the sale,

AI assessment note: “the whole thing definitely seemed very surreal, but at the same time”

Q Okay. First of all, Tony, this is not how this narrative is supposed to go. I mean, you were so young and this is just three years after you graduated from college. So, I mean, was that totally overwhelming that, that, that, that happened so quickly?

A Well, the whole thing definitely seemed very surreal, but at the same time, What a lot of people don't know is the real reason why we ended up selling the company, and the real reason was because the company culture had gone completely downhill, and I myself dreaded getting out of bed in the morning to go to my own company, which is kind of a weird feeling, because when it was just five or 10 of us, and we were all friends, it was a lot of fun. We were kind of your typical dot-com startup back then. We were sleeping under our desks, had no idea what day of the week it was, working around the clock, but it was Really exciting, and it was fun growing, and as we started hiring more and more people, we eventually ran out of either friends or friends of friends, and so I had to do, figure out how to do interviews and, and so on, and not everyone we hired was good for our culture, and by the time we got to a hundred people, it wasn't any one specific hire, it was just death by a thousand, or in this case a hundred paper cuts, and that's really what led to the sale.

AI assessment note: “Well, the whole thing definitely seemed very surreal”

Q You are so young. I mean, you're still in your early forties, and you've done so much. So, so where do you see yourself in, like, 20 or 30 years from now? I mean, are you still running Zappos? Are you, are you doing something else?

A Um, I know, because if you asked me 20 years ago, I mean, Zappos wasn't even around, but I would be imagining it certainly wouldn't be this, um, so I don't know, I mean, I generally don't try to think that far ahead. I guess for me, it's just making sure that I'm doing what makes me happy, and you know, so many people are unhappy at their jobs for various reasons. It could be the The work itself, the culture, uh, the lack of autonomy, you know, all those things are things that we want to, uh, hopefully show that there's a different and better way of, you know, not just work, but I just think of it as life, and, um, I know, and it helps spread that, I guess.

AI assessment note: “so I don't know, I mean, I generally don't try to think that far ahead.”