The Exchanges

Q So you exited from Traffic Marketplace, and then you went to shift?

A Uh, so there's actually a lot more in between. Um, so, so Traffic Marketplace was really my first, uh, angel investment, and I put, put some of my, kind of, very limited, uh, funds at the time into the company, and, and saw a nice return, and thought, hey, I kind of like this angel investing thing. Um, yeah, after, uh, After working at Traffic Marketplace for a little while after the acquisition, uh, was involved with a company called, uh, called Tag World, which was a social networking site that I started with, co-founded with a few other partners. Um, this is back when MySpace was really the dominant, uh, player in the social networking space, and so, My space was, was, was significantly larger than we were, but, um, so we were, we were playing in that space, um, uh, you know, did that for, uh, for several years, and then ended up selling the company to, uh, to Viacom.

AI assessment note: “so there's actually a lot more in between.”

Q Did the, did the bubble affect you much being in the industry at the time, or, or did you manage to avoid it?

A Um, you know, I mean, I wasn't running the show at iWin. I was one of the more junior people there at the time, so, um, you know, I, I think, uh, I mean, look, there were, there were meetings that were had internally where there were discussions of, you know, IPOs for iWin and a variety of other things, and so in that sense, I think, you know, It did affect me and the company in the, in the sense that just people's expected valuations for these things, you know, went way down and the IPO window closed as well, um, for a pretty significant period of time. But that said, you know, the, the exit for, um, you know, for the founders and investors for, you know, both Iowan and Traffic Marketplace were very good. So, um, couldn't complain. Um, you know, it ended up

AI assessment note: “It did affect me and the company in the, in the sense”

Q So there's always another startup to be. But now as chairman of swift, of swift shift, and as an angel investor, uh, You, you sit on both sides of the table, really. So what would you say is the most valuable insight that you've gained from experiencing the side of the entrepreneur and the side of the investor?

A Um, I'd say that you, I'd say the main thing is that you just end up having a lot more empathy for, for everyone in the whole ecosystem, right? Because you realize as an entrepreneur, you know, sometimes Sometimes when you just, when you start a company for the first, second, or even third time, you're, you know, there, there can be a lot of thought of, of, you know, oh, you know, these VCs who are shooting me down left and right, which, you know, happens, happens to this day, you know, more often than not. You know, as an entrepreneur, you know, sometimes it can be easy to think like, oh, you, you know, These guys are, are, are tough to deal with, and, and you, some people get into the attitude of, you know, ah, VCs are, are, are the worst, and it's just not the case, you know. I mean, VCs and angel investors are, are, are people just like, you know, entrepreneurs are, and they're trying to, you know, do as well as they can for their, uh, for their LPs, right, or for themselves if they're investing their own money. So, you know, By doing, by doing investing on your own, you start to realize that, you know, you, you have a lot of concerns and, and entrepreneurs, like, it's great when entrepreneurs are very open with you and tell you about what you're, tell you about what you're doing and keeping you updated. So I'd say as an entrepreneur, you have a lot more empathy for your in…

AI assessment note: “the main thing is that you just end up having a lot more empathy”

Q Did the, did the bubble affect you much being in the industry at the time, or, or did you manage to avoid it?

A Um, you know, I mean, I wasn't running the show at iWin. I was one of the more junior people there at the time, so, um, you know, I, I think, uh, I mean, look, there were, there were meetings that were had internally where there were discussions of, you know, IPOs for iWin and a variety of other things, and so in that sense, I think, you know, It did affect me and the company in the, in the sense that just people's expected valuations for these things, you know, went way down and the IPO window closed as well, um, for a pretty significant period of time. But that said, you know, the, the exit for, um, you know, for the founders and investors for, you know, both Iowan and Traffic Marketplace were very good. So, um, couldn't complain. Um, you know, it ended up

AI assessment note: “It did affect me and the company”

Q So you exited from Traffic Marketplace, and then you went to shift?

A Uh, so there's actually a lot more in between. Um, so, so Traffic Marketplace was really my first, uh, angel investment, and I put, put some of my, kind of, very limited, uh, funds at the time into the company, and, and saw a nice return, and thought, hey, I kind of like this angel investing thing. Um, yeah, after, uh, After working at Traffic Marketplace for a little while after the acquisition, uh, was involved with a company called, uh, called Tag World, which was a social networking site that I started with, co-founded with a few other partners. Um, this is back when MySpace was really the dominant, uh, player in the social networking space, and so, My space was, was, was significantly larger than we were, but, um, so we were, we were playing in that space, um, uh, you know, did that for, uh, for several years, and then ended up selling the company to, uh, to Viacom.

AI assessment note: “there's actually a lot more in between”

Q And when you, when you made these exits, I mean, does it feel incredible as an entrepreneur? Does it, do you get that feeling of immense achievement, or do you get the feeling of actual loss? Some people describe it as kind of selling a baby type thing. Do you know what I mean? Um, Which one do you fall on? Do you get quite sad, or is it exciting?

A Uh, to be, you know, to be perfectly blunt, you know, I, I, um, I mean, I, I love doing startups, I love investing in them, and being involved as an entrepreneur, but, um, You know, ultimately I would say it's more the former, because I, I view it as, it's kind of a means to an end. Um, and ultimately the, the goal is to, um, you know, the goal is to build something, um, that you're excited about, that creates value, you know, for, for users and, you know, of course for investors and, uh, hopefully founders as well. Um, and so I, I think, you know, having been through a few exits, um, it might, I'd say the feeling is more relief. I think a lot of other entrepreneurs would probably say the same thing, just because you get to a point, especially, you know, going through, you know, a due diligence process, which is, um, which is challenging, right?

AI assessment note: “I'd say the feeling is more relief.”

Q Do you agree with the school of thought that says that kind of failure is a good thing and that, you know, failure is necessary for any great entrepreneur, or do you think it can be a good thing, but it's not necessary? Do you, which side do you fall on?

A Um, probably on the it's not necessary side. I think, uh, I think you, um, I forget who said it. There's a funny quote about, um, about failure I read recently, and again, I'm forgetting who said it, but, um, it's very easy, uh, after you've been massively successful to say that failure is a great thing, and I think that it's somewhat, um, It's somewhat self-selecting, right? Because the people who are inevitably being, you know, interviewed by major media outlets, um, have been successful, um, you know, either as entrepreneurs or, uh, um, investors in this world. And so, you're not really, you're, you're hearing the perspectives of, of the winners. Um, there are a lot of people out there that have failed in their startups, and it's, it's not, um, it's not a fun thing. I think that, um, I, I think that you learn enough lessons along the way in a startup that, uh, You learn enough lessons along the way, I would say, where, you know, you, you are very much challenged. Um, I, I'd say having to fail is not necessarily, um, something that, that is a good thing necessarily.

AI assessment note: “probably on the it's not necessary side”

Q And when you, when you made these exits, I mean, does it feel incredible as an entrepreneur? Does it, do you get that feeling of immense achievement, or do you get the feeling of actual loss? Some people describe it as kind of selling a baby type thing. Do you know what I mean? Um, Which one do you fall on? Do you get quite sad, or is it exciting?

A Uh, to be, you know, to be perfectly blunt, you know, I, I, um, I mean, I, I love doing startups, I love investing in them, and being involved as an entrepreneur, but, um, You know, ultimately I would say it's more the former, because I, I view it as, it's kind of a means to an end. Um, and ultimately the, the goal is to, um, you know, the goal is to build something, um, that you're excited about, that creates value, you know, for, for users and, you know, of course for investors and, uh, hopefully founders as well. Um, and so I, I think, you know, having been through a few exits, um, it might, I'd say the feeling is more relief. I think a lot of other entrepreneurs would probably say the same thing, just because you get to a point, especially, you know, going through, you know, a due diligence process, which is, um, which is challenging, right?

AI assessment note: “ultimately I would say it's more the former... I'd say the feeling is more relief.”

Q Do you agree with the school of thought that says that kind of failure is a good thing and that, you know, failure is necessary for any great entrepreneur, or do you think it can be a good thing, but it's not necessary? Do you, which side do you fall on?

A Um, probably on the it's not necessary side. I think, uh, I think you, um, I forget who said it. There's a funny quote about, um, about failure I read recently, and again, I'm forgetting who said it, but, um, it's very easy, uh, after you've been massively successful to say that failure is a great thing, and I think that it's somewhat, um, It's somewhat self-selecting, right? Because the people who are inevitably being, you know, interviewed by major media outlets, um, have been successful, um, you know, either as entrepreneurs or, uh, um, investors in this world. And so, you're not really, you're, you're hearing the perspectives of, of the winners. Um, there are a lot of people out there that have failed in their startups, and it's, it's not, um, it's not a fun thing. I think that, um, I, I think that you learn enough lessons along the way in a startup that, uh, You learn enough lessons along the way, I would say, where, you know, you, you are very much challenged. Um, I, I'd say having to fail is not necessarily, um, something that, that is a good thing necessarily.

AI assessment note: “probably on the it's not necessary side”

Q So there's always another startup to be. But now as chairman of swift, of swift shift, and as an angel investor, uh, You, you sit on both sides of the table, really. So what would you say is the most valuable insight that you've gained from experiencing the side of the entrepreneur and the side of the investor?

A Um, I'd say that you, I'd say the main thing is that you just end up having a lot more empathy for, for everyone in the whole ecosystem, right? Because you realize as an entrepreneur, you know, sometimes Sometimes when you just, when you start a company for the first, second, or even third time, you're, you know, there, there can be a lot of thought of, of, you know, oh, you know, these VCs who are shooting me down left and right, which, you know, happens, happens to this day, you know, more often than not. You know, as an entrepreneur, you know, sometimes it can be easy to think like, oh, you, you know, These guys are, are, are tough to deal with, and, and you, some people get into the attitude of, you know, ah, VCs are, are, are the worst, and it's just not the case, you know. I mean, VCs and angel investors are, are, are people just like, you know, entrepreneurs are, and they're trying to, you know, do as well as they can for their, uh, for their LPs, right, or for themselves if they're investing their own money. So, you know, By doing, by doing investing on your own, you start to realize that, you know, you, you have a lot of concerns and, and entrepreneurs, like, it's great when entrepreneurs are very open with you and tell you about what you're, tell you about what you're doing and keeping you updated. So I'd say as an entrepreneur, you have a lot more empathy for your in…

AI assessment note: “main thing is that you just end up having a lot more empathy”

Q so. I think it's clearly paying off though, because according to my research, you've had 10 exits so far. Uh, now I don't know if that's quite accurate or not as of today. Um, but, anyway, leading me to ask, how do you pick the right startup to back? Are there aspects that you focus on particularly, or do you look at the company as an, as a whole overview?

A You know, it's one of those things where I think, I think with me and, and none of these, um, none of these comments are, are, are groundbreaking and are, and are kind of cliches, I would say, but I mean, it really starts with team, right? That's the most important thing for me is just the founding team over product. Um, well, I would say it needs to be an idea or product that, Seems compelling to me. So that's obviously a, um, a preliminary hurdle that you have to get over. But, you know, if you look at the, at the business and you think, okay, or at least this is, this is the way I look at it, you know, and you think, okay, this business has the potential to, um, you know, to be successful or get to a certain point where investors would be happy. Um, and then from there, so much of it is, Again, at least for me, less about trying to poke, you know, holes in, in the business model or talk about kind of, you know, what are you going to do if X, Y, or Z happens? Because, you know, ultimately the people running these businesses know more about them than, than I do.

AI assessment note: “it really starts with team, right? That's the most important thing for me”

Q so. I think it's clearly paying off though, because according to my research, you've had 10 exits so far. Uh, now I don't know if that's quite accurate or not as of today. Um, but, anyway, leading me to ask, how do you pick the right startup to back? Are there aspects that you focus on particularly, or do you look at the company as an, as a whole overview?

A You know, it's one of those things where I think, I think with me and, and none of these, um, none of these comments are, are, are groundbreaking and are, and are kind of cliches, I would say, but I mean, it really starts with team, right? That's the most important thing for me is just the founding team over product. Um, well, I would say it needs to be an idea or product that, Seems compelling to me. So that's obviously a, um, a preliminary hurdle that you have to get over. But, you know, if you look at the, at the business and you think, okay, or at least this is, this is the way I look at it, you know, and you think, okay, this business has the potential to, um, you know, to be successful or get to a certain point where investors would be happy. Um, and then from there, so much of it is, Again, at least for me, less about trying to poke, you know, holes in, in the business model or talk about kind of, you know, what are you going to do if X, Y, or Z happens? Because, you know, ultimately the people running these businesses know more about them than, than I do.

AI assessment note: “it really starts with team, right? That's the most important thing for me”