#18 - The Big Business of Wacky Domains

I sold internet real estate to the tune of a half a billion dollars worth. dot app dot blog dot church Some of these you've probably seen, but my company was responsible for selling a lot of those. It's what's called a Ascending clock. Second price option.

The way it works is In this case, every 20 minutes it increments up and it's ascending. we'd start the betting at$200,000 times the number of betters. Six hundred thousand dollars to start. Every twenty minutes it goes up by six hundred thousand with a minimum increment of twenty percent.

you know, once we get to three point six million, it goes up higher. Your top auctions went for how much? What is it like ten million or is it more like It's over a hundred million. Oh my god. Shiel, you're here. Yeah. Did you bring your A game? Always bring my A game. Do you stretch in the mornings? Do you eat your breakfast? What do you do to to get going in the morning? I actually eat no breakfast, drink no coffee ever. So you're just a faster now. That's not what you called it. You happen to not eat breakfast. I just happened to not eat breakfast because I don't like it.

And then if I drink any coffee, I won't sleep at all like a wink at night. So no caffeine for me. I just naturally am lucky that I wake up with a lot of energy. It's awesome. Great. And so you're here to tell your story. I met you Maybe four or five years ago, I don't remember how long it was. Yeah, probably. You came over to my office and I don't even know how you got there, to be honest. I don't even know Did I reach I probably reached out to you some I don't know what, yeah. But I remember sitting at the bar in our office. I do. Yep. And you told me one of the craziest stories of how you of how someone made it that I've met here in in San Francisco. So million dollar question. You've made a million bucks. How did you do it? Yeah, so I sold internet real estate To the tune of a half a billion dollars worth.

And when I say internet real estate I mean top level domains, which is like A a domain. would be like million dot com. But a top level domain would be

The dot com part. So that all these new ones that came out. dot app dot blog dot church. Some of these you've probably seen. My company was responsible for selling A lot of those.

Gotcha. Okay. If I wanted to create Sean.com, which I do. Yeah. And was taken. And so I was like, Okay, shit, what do I want to be instead? I can do Sean One Two Three dot com. That's less cool. Could I get Sean.co, could I get Sean. XYZ app, Sean.xyz, Sean.badass, whatever, right? So these other domains, these other dot whatevers exist now. And you were responsible for selling'em to the highest bidders. That the whole class of dot like what's a what's a what's one of the famous like

Not dot com, not dot co, but like what are some of the other big ones? So dot app is a big one. A lot of these have just started to come out in the past couple of years, so you have not heard of them that much yet.app is gonna be a big one, I think. Dot blog Potentially all the blogs have gone. decreased in value since this whole thing came out. XYZ is a friend of mine owns. And he his his thing is The alphabet ends in dot XYZ. Why shouldn't you Okay. He made a bet on that. Okay. So there's a whole bunch of these that are out there and you were selling them. So let's rewind to the beginning of that. You're sitting around, where do you get the idea to even go do this? How do you even realize that this is an opportunity worth chasing? Yeah, so I just heard through the news that you could buy your own dot whatever. In twenty twelve, it was all over the news, like

People can get your own dot whatever. And so I wanted to find out more about this. And naturally there are a few things that come to mind. Like if you were doing it today, you might want to do something like in the crypto space like dot PTC. Unfortunately in twenty twelve, nobody did that. So In twenty twelve you had to apply, you had to pay pay a hundred eighty five thousand dollars to apply for your own dot whatever. So what would you apply for? So like I would I mean the first one that comes to mind is like porn, basically. What's the most popular thing on the internet, like dot XXX, porn sex, something like that, right? Because if I owned that, then every basically anybody who wants to have a porn site. Now they have an alternative to.com, which is usually taken. Exactly. They can come to me and I can sell them their other domains, essentially. That's exactly right. Yeah. I can, which is the governing body of the internet, actually made an exception and like a while ago created.xx. How do they decide which of these are going to exist? So all of the two letter ones.co

Dot. V C dot T V. They're all country codes. So dot V C is Saint Vincent in the Grenadines. Oh really? What's T V? So they so under the premise of every country can have their own. Yeah. immediately got co opted by business to be like great dot T V.

Yeah. Sports. Remember remember like ten years ago there were all these like dot L Y domains? That's Libya. You're supporting Libya. And do they get anything out of it? Yeah, they do. It's the country like the country manages them and Like if you buy a dot CO domain, that's Columbia. So nobody else could have bought it, the country owned it and they're and they sell off the different things. So how much does the coun do you know how much the country's make off? Like how much did Libya make off of all the dot LYs it sold? Do you have any idea? I don't I don't know. Think about it this way, they probably make

You know, whatever it costs. And we we could e easily do the math, but it's in the hundreds of millions that they've made. Wow. Okay. So this are the country ones. And then they started doing just words like dot app or see so the way this thing worked was in twenty twelve you'd apply for your own dot whatever. So let's say that me and you applied for dot app. You had to pay hundred eighty five thousand dollars just to apply. And by the way, they got two thousand applications, which means they made three hundred sixty million dollars in application fees. Wow. And if you were the only one that applied for dot app, you got it. It was yours. You paid a hundred eighty five K one time and then, you know, some ongoing fees, but it was yours. And then by the way, you could sell everything. Like Facebook dot app would have to pay you something per year. All these things would have to pay you. But If you, me, and let's say some third party Who should be used as a third party. So me, you, and Donald Trump get into a getting war. Me, you and Trump. So me, you and Trump all we're just doing this so I can beat Trump. So me, you, and Trump.

All want.app. So ICANN, the governing body of the internet says you guys figure it out amongst yourselves. If you can't figure it out at some later date, ICANN will hold an auction. And they'll get all the proceeds. But I can prefer is that we sort it out amongst ourselves. So what happens next? So you go to Donald Trump and you say Well we first anti up our our fee. We put we just put a hundred eighty five K in just to say That was just the application fee. Right. So that's that's basically a side cost. Right.

And and then They had a reveal. One day. They were like, Here are all the people that applied. And then we found out, ah shit. Sean applied.

Trump applied. I don't know if I'm gonna get this. So then what happens is like the three of us would like be in this what we call contention set, which means like contenders to win it. And So this happened and the players aren't like me and Trump, although kinda similar. They are they're like Google, Amazon, there's this billionaire guy who lives in the Cayman Islands, really interesting fellow. There's a company called Donuts that raised a hundred and eighty million dollar like seed round effectively. Just for this. Okay, so me and Trump we go into the bidding war. Yep.

And we've each paid our application fee. We've each paid our application fee, and then what I said was Are you a better negotiator than Trump? You wrote the order the deal, man. Are you a better negotiator? And you might say no. And the people involved again are these it's like Google And this billionaire. Right. And so what we said was we can create a fair, transparent mechanism for you guys to sort this out. The way it works is in this three party auction, it's what's called a ascending clock second price auction. Okay. So what that means, it's it's really simple. Ascending clock, it's a clock auction meaning meaning it's timed. Okay. So in this case, every twenty minutes it increments up and it's ascending. Okay. Simple.

So in a three party auction, we'd start the bidding at two hundred thousand dollars times the number of bidders. So it would be six hundred thousand dollars to start. Every twenty minutes it goes up by six hundred thousand with a minimum increment of twenty percent. You know, once we get to three point six million, it goes up higher. Okay. What's your willingness to pay? Okay. So I'm willing to pay right out the gate. And now my strategy should I be telling my topbed or my like low ball alpha. So you for the sake of this, you're gonna tell us your top bid but in the actual auction, you'd only say whether you're in an eight round or not. Okay, cool. So let's say I'm willing to pay up to ten million bucks to pay for the case. Okay, cool. Donald Trump, he says he's a billionaire. I don't actually think he has that much money. So let's say his willingness to pay is like five million bucks. Okay. And then My willingness to pay like

I think dot app has a lot of value. It's gonna have a lot of value in the future. You know, domain names are less important, but you still want your like Dot app. Your your app is what's important. And it's a memorable way for people to remember, you know, what right what the thing is. So I'm willing to pay more. I'm gonna say I'd be willing to twelve million bucks. Okay. So

In this auction, what's gonna happen is we're gonna start the bidding six hundred thousand. And we used to say yes, we're still in. We're in. Okay. So either you say You're in or you're out. And if you're out, you say what price you were in for let's say Donald Trump was actually only in for a half million bucks. In the first increment, he would say, I'm out and I'm in for five hundred thousand. Okay. So we we keep bidding, we keep bidding. And then Sean, once we get to 10 million, you're out. Right. That means I've won. Okay. And so I pay ten million bucks.

Uh okay. So you were you were willing to be in at ten. You might have continued to be in up till twelve. I would have been, but nobody nobody else is there. Yeah. Nobody knows nobody knows what your real number's gonna be. Exactly. Okay. And then so I pay ten million bucks. But the real beauty of this auction is where the ten million bucks goes. So who gets the money? Uh well nobody owns all app, so is it ICANN that gets it? I don't know. So a lot of people would think I can get some money, but actually this is a separate auction from ICANN. So in this auction, the people that get paid are you and Donald Trump. So the ten million bucks that I pay go away. Yeah. We pay we're paying you off effectively to go away. And really what this is is like any time you're splitting a partnership, this is like

a good way to do it. So like if you and me We're in business together, fifty fifty J V. Right. How would we s decide like how much would I have to pay you to like free my shares. Yeah, exactly. So we would basically do this kind of auction where like Whoever's willing to pay the most to the other person. And that's the idea behind this auction. So they actually get the money. They get the money. So I'm paying you guys each five million bucks minus my auctioneer fee, which would be in this case four hundred thousand dollars. So we took Four percent of the auction fee. Wow. So the first thing is were there people who just went into the auctions trying to get paid out, trying to lose

You had to apply Basically a year before any of this like how the auctions would work. Yeah. Oh, okay. Okay, so cool. So that already prev prevented that from happening. The second thing was Your Top auctions went for

You know, how much? What is it like ten million or is it more like a hundred million? It's over a hundred million. Wow. Yeah. So I can't talk about the exact prices on the names, but the top couple went for over a hundred million. And The cheapest one probably still went for like half million bucks. Right. Okay. So I'm fascinated, but you were sitting there and you said, Oh, cool, interesting. They're releasing these domain names. Yeah. But then we fast forwarded to and then I'm running these high stakes hundred million dollar auctions. Certainly there was something in between where you were like, Okay, how does this work? Totally Do they need an auction solution? Can I make that auction solution? You know

How did that actually how did that idea come together from the moment you were just curious about these new domains? Yeah, so it was really my co founder is like an expert in auction theory. We knew this was happening and we just like sat down and we were like, how do we devise a way for this to work? Okay. And how do we build any credibility in this industry? Nobody knows us. So We did a couple things that I think worked really well in our favor. A, like you know, our co founders and a PhD from Stanford in auction theory. And so this was just a buddy of yours, or Buddy, yeah. Actually there's another totally random story, but I met my co founder On a train in India in two thousand six. Okay.

Sat next to him. He turned out he was a friend of a friend, but he's like a German dude. Right. And I was traveling in India. We ended up on this like forty hour train ride together, became really good friends, have like worked together a bunch of time since. Wow. Okay. All right. That's amazing. Then and that's also funny how common that is, how common the randomness is. Your buddy knows a lot about auction theory. Yeah. And so how did you even know that the companies were gonna have trouble sort of sorting this out amongst themselves? Because these are billionaires and Google and Facebook, so you're not even talking to these people. How did you know that they needed this type of a solution versus We actually just Talk to them and we were like hey Do you need a solution? And most of them said no, actually.

Like they were like we don't want to work with you. And in fact Like for a long time it looked like this business was gonna be a total goose egg. You did what there? You emailed the lawyers, you were calling somebody. Like show up in person. Yep. Like so they're they had these conferences three or four times a year. We'd go to all the conferences and the domain conferences? Domain conferences. Okay. Nice. Must be a uh that sounds like a party. It was cool because they were like all over the world. Like I went to Johannesburg, Buenos Aires, Singapore. Like You don't even know if this is a business yet. You're just following your nose. You're just curious. Curious, yeah.

And so my co founder Ulrich has this like loves to tell the story of like you gotta just get in front of these people. And so I literally just like looked up everyone who had not responded to me on LinkedIn, on Facebook, whatever, and tried to find their face. Like memorize what their face looked like. And then at this conference, I would just be searching for them. And then so at one point I saw this guy that I needed to get in touch with for one of our auctions. Okay. Cause like in this three party auction, if I only have two of the three parties, I don't have an auction. I don't make any money. And these auctions some of them were like thirteen or fourteen parties. Right. So if I got if I got thirteen of the fourteen, I don't have an auction. I have no money. But if I get fourteen I'm

Really doing well. Right. So this party that I could not get in touch with, no matter how hard I tried. I was in Buenos Aires, saw this guy outside smoking. And then I was like, How do I get in touch with this guy? I don't smoke cigarettes, but I bought a pack of cigarettes. And then I just went outside and started smoking a cigarette with him. And I was like, as if I hadn't been trying to get in touch with them this whole time. I was like just shooting the shit. And then ultimately like you know, became friendly with this guy and then I was like, Oh, like you're the guy. I actually it's funny, like we're running this auction, I've been trying to get in touch with you. And then he was like way more menable. He like started he started talking. Yeah. That's okay. It's not quite like, you know, the CIA operatives that go undercover and start doing heroin to get into the cartel. But it's close. It's the closest you know I've I've heard. Okay. So you you start smoking the cigarette. So you're trying to get in touch with all these people. And then convince them that our way is the way to do it. And we had a couple of problems. It was the billionaire in the Cayman Islands I was telling you about. She did not want our auction to happen. If our auction happened

He was reasoning that the prices would go up. because people are incentivized for the price to go up because they want to sell. Right. They want to make money. Yeah. And so he Wrote. like a letter to the Department of Justice and was like, If these guys do this, would this be a bad thing. And the Department of Justice sent him basically a non response. But he publicized it as if the Department of D of Justice was against what we were doing. I see. And so that made Google a lot more suspect of us. Right. And you know, they don't want to do anything that could potentially be a foul of the Department of Justice. So

We ended up having to work our asses off to get Google. Like I spent a year like Going to Mountain View. Convincing people. Like you know Met with a lot of people at Google trying to convince them like draw on a whiteboard our solution. Right. The reality is this is better than another outcome for the Department of Justice. The other option is they could get into a room and negotiate. I don't see how that's better than this auction. And why did they ultimately come around? So how what was your pitch? You get you finally get in front of Google and you're like look you're the guy who needs to agree to do this. Yeah.

Their initial reaction you're saying was, No, we're not interested in this uh in working with you guys exactly. And if one party doesn't want to work with you guys, it doesn't work. It doesn't work. Seems like it seems like a terrible business, but I love that it worked out. So What was ultimately what was your pitch to convince them that this will be better for you than everybody free for all trying to negotiate? Okay, so a few things. Some people were worried that the price would go up based off of this. But the reality is if like everybody has a price that they're willing to pay, you're not gonna you're not gonna bid higher than the price you're willing to pay because then you might end up getting it. Right. Like if you end up winning the auction for a higher price just because you're trying to drive up the price, that doesn't make any sense. So like this whole Notion was unfounded. And you know, we were able to convince him that like we got

Google's chief economist Hal Varian involved. And It was cool. It was like a really amazing experience. And then Google tested us out first. They had us run another auction for them just see how they liked working with us. Right. And it went well. And is this a piece of software or wh how did you actually what was the product in this case? Yeah, the product is yeah, it sounds like relatively trivial. It's actually not that trivial to build. Like there's a lot of security involved. And yeah, it it is like a online portal where you can go in, make bids

See what happens. There's also, of course, like a banking component. So even to enter a bid, you have to have put down a a deposit. And we have because the bidders are so international. They're in accounts all over the world. And then even after you've bid, we have to hold a bunch of money in escrow. Right. And one of our bidders A large software company had a requirement that you couldn't use the money that they gave you to bid against them in a future auction. So we basically had to hold this money in escrow. So we're holding like hundreds of millions of dollars in escrow in accounts like in Hong Kong. That's actually pretty smart of them though to uh to to put that in. Can I tell you my bidding story like this? Yeah, I think I know the story and it's a beautiful story. So I didn't know how any of this shit works.

But four or five years ago, maybe maybe more, I don't even remember at this point, my investor Michael Birch comes to me. He's on the podcast. His episode's called The Hippie with a Billion Dollars. So he comes to me and he says, Hey, you know, this company I sold to AOL called Bebo. It's actually AOL wrote it off. This guy kind of bought it off them. He is not really doing very good with it. In fact, we're gonna sue him because he took our money. We invested in him. It's not really working out. But long story short, this company's gonna go through bankruptcy. Would we want the asset? Like we could get the domain name, we could get the servers, we can get the email list of maybe eighty to a hundred million people. Maybe there's some value in this and hey wouldn't it be be cool if we could turn this around. It was more really that. It was like cool. Yeah. That was my baby. I sold it to them. They kind of besmirched it and like maybe I'll buy it back and do it again. Like wouldn't that be cool? And I was like, I don't know. Yeah that you know, I was like interested'cause I don't know any better. And he was like, you know, most internet companies never make a comeback, but let's try it. Same sort of thing. It goes to this bankruptcy process. I don't know anything about bankruptcy, but there's like a few weeks and then it's like there's a court date in LA. We gotta go to LA and what we're gonna try to do is we're gonna try to buy it out of bankruptcy, essentially. And we we just have to pay off a few debts, you know, whatever the money we put in, that'll go to the debtors and the asset could be ours. So we go down to LA It's me, our lawyer, and our COO. And beforehand we're trying to come up with our strategy and we're like you know, chickens with our heads cut off. We're like, Well, what's it worth?

And we're like, Well who the hell knows? We had very little data, plus you're just like estimating what you think you can make it into, which is a dream, really. And we don't know who else is interested. We've seen in the data some other companies that are sniffing around because they requested some data. Oh yeah. And then you can see who opened the folders. Okay, it looks like these other companies are involved. We don't know. So we show up in LA, we go to the court. I still don't even know actually how this process is gonna work. I assume the judges is gonna say The judge immediately just says, All right, you three companies are here to buy this, go in that room over there. Sort it out amongst yourselves. This is kinda what you're talking about, right? Sort it out amongst yourselves and then come back to me and tell me who's the winner and what's the price. And we're like, What? And there's like yeah, there'll be a mediator that will sit there and like just watch the proceedings happen. Just to make sure there's no foul play. So we're like we go in this tiny room, smaller than this room, we're doing this podcast in and it's us and it's match dot com.

And then there's tagged, which is another like social network, but then lost to MySpace, lost to Facebook, and was sort of still around. And so we sit down at the table. I have no idea what's gonna happen. And I hoped it was a process like what you're talking about, with some structure. Yeah. And like, you know, whatever. And instead it's like okay. So What's the starting bid? Uh we'll start the bid at uh Hundred fifty thousand. And we're like So somebody says one hundred fifteen, we're like we'll do and they just have some minimum, like you have to go up by whatever. I was like all right, we'll do one eighty, we'll do two thirty, whatever. It just kept going up.

And did wait so at this point, did you have a number in your head? Yes. So we had in our mind we had valued the thing. We were like okay, I think this thing's probably worth, you know, just on the parts. If you just resold the parts right away. The domain name the domain, the servers, the lists, you know, stuff like that. This might be half a million bucks. Optimistically half a million, maybe it's$350. fifty thousand, whatever. We were talking about that. And then Michael, you know, in his wisdom was like look I don't think we're gonna go in and we're gonna be able to get this for like Three hundred, four hundred thousand. So like I don't think we should try to figure that out. I think we should be like, what are we willing to pay? And I think this thing's gonna go for a million bucks and I'm willing to pay a million bucks. Yeah, for him, there's emotion tied into it too. Like it was baby. So he was like I'm willing to pay a million bucks. And we're like, Okay, well, I guess that's our strategy now. So in my head, I'm like million bucks. I have no idea what these other guys are thinking. And we sit down and so it starts going up, starts creeping up. At about three hundred fifty thousand, tagged as like

You could tell this guy was like I flew to LA, I thought like nobody would be here. What the hell am I getting myself into? He was just like uh like I'm out. I don't I don't know what's going on here. Let you guys do whatever you're gonna do with this. So now it's just heads up. Us and the IAC group. And so we we continue and it just g and everybody's going up in very even increments of like whatever the first person threw out was like thirty thousand more or something like that. The next that's just how it went up every time. Every time. And uh tries to have like a poker face about themselves. And at about seven hundred thousand, they like stepped out of the room to be like we need to make a phone call. Is that okay? We're like uh the mediator was like, Yes, no problem. You can take a break. So they go out, take a phone call, and I'm huddle up with the lawyer. I'm like, Okay, this looks like this is probably what they were pre approved for.

'Cause they gotta go call their boss to figure out what they can do. They're either gonna come back and say, No, take it. Fantastic. Or they're gonna come back with a new kind of like top price in their mind. And so that's probably gonna be an even number. So just test like every time it gets to eight hundred, nine hundred, or a million, don't let them get that number. Like jump above it a little bit. A little bit. And I talked to the media, I was like, Hey, look, they can't do this again. And she's like, Yeah, okay, they're we're not gonna do any more we're not gonna do any more breaks that interrupts with. So then you knew that they had an upper limit and if you go a little bit above that upper limit, it's yours. Exactly. And I went I went outside to try to make small talk with them too, to be like what are you guys gonna do with this anyways? And they actually like like fools were telling me what they were gonna do with it, so I was like, Oh, they don't have like a robust plan. Yeah. They just wanted the SEO and they wanted some other benefits. So I was like, okay, these guys aren't serious. So that's exactly what happened. They come back in and it starts going up again and at a million our top was supposed to be a million. It was that nine hundred something and she just our lawyer just jumped and went one million and fifteen thousand. I just threw fifteen thousand on top.

And they were just like take it and we were like, Great. And they were I was like, What was your max? He's like a million was our max. And he's like, We just didn't know how far you guys would go and I told him, I was like, dude, our guys like emotionally attached to this. Like he's gonna keep going. You should just drop out now before like you know, this gets out of hand. And so they they just let us take it at our also max. And so I I just remember sitting there being like this was a crazy experience, like a crazy hand of poker I got to play. But I should have even thought in that moment, like there's gotta be a better way. And it sounds like you guys actually built a better way. But actually, like the way you guys did it is not bad. I mean, so typically in that thing, what I would have suggested is like you each put a number of. In an envelope and And that's what it is.

What you guys did allows the bidding to go higher. Right. Because There's like excitement. Like you said, like they had to go out and come back in. But like generally in auction theory, like we optimize for the fairest price. Okay. And we're not necessarily optimizing for the highest price. And that's why yours ends with the second highest price, basically. Yeah. And the reason for that is let's say if all three of you put your numbers into an envelope, you'd be thinking like what is somebody else willing to bid? Right. Instead, if it's like I'm gonna pay the second price anyway You're gonna put my max. But my max. Yeah, that's brilliant. Okay. And you didn't invent that, you just took I mean, That's like a known auction theory thing. And like eBay auctions. If you can bid as high as you want and you'll pay increment one increment over

The next high spid. Right. So that's like a standard auction theory thing. We didn't invent it. Gotcha. So you basically built this high stakes eBay. Yeah. Selling internet real estate. Yeah. Which is incredible. And you did this this whole process took about how long? So from you know, you guys have the idea to like your first auction, how long was that?'Cause I like to give people a sense of like how long business takes to actually mature,'cause when we say it sounds Bang bang bang. Yeah. I think it took like eight months and that was a very difficult eight months. Yeah. Like we really didn't think it was gonna work. And then we had no idea how much these things were worth.

Like the first auction So to give you an idea, I think we did eight names in that first auction. And we were like taking bets amongst ourselves, like how much is each of these things the first ones we did it was like dot vote, dot photography, dot now, dot red. Like the there these were the ones in the first auction that we did. And so like dot photography I'll use as an example. How much do you think dot photography went for? I don't even know what you can make off these, so I I mean I'll I'll throw a number out there just to be long. I don't know. Uh so I would say dot photography somebody's gonna pay fifteen million bucks for it. Okay. It actually went for a lot less. It was like a single digit million number. But a lot of people say that's a lot for dot photography. Like who's going to use dot photography? Yeah. Like it's such a long name. Like when you're used to like a three letter TLD or two letter even for the country codes, like dot photography is really long. But actually it turns out that photographers want to be like they like their name dot photography. Right. They don't want their name dot photo because that seems unprofessional. So they like their name dot photography or like wedding dot photography or like San Francisco wedding dot photography, all these names. I'm not going to tell you exactly how much it costs, but let's say it costs three million bucks. So when people learned of this, they were like

Somebody paid three million dollars for not photography? That makes no sense. But in that first year They were selling these names. for like fifty bucks a dot photography name. And they sold like a hundred thousand of them that first year. In the first year they made five million bucks out of it. And then if you think about it, right? It's a recurring it's like kind of like an annuity. Like obviously there's degradation over time, there's churn, but like it's pretty consistent. Right. And so that's at the tone then for you guys. Yeah. And then and there there were peaks and valleys of like after that first auction and then the first names started selling and we realized, oh shit, people want these names. Then the prices started going up. And then we had some crazy ones that were in the hundreds, as I mentioned. And then after a while when like the first several had a lot of success,'cause they were the first names, the first new names sold. And there were all these like domain squatters that were like buying them. And then when we realized like oh shit

Now there are a lot of these new names. Then people started selling them for less. Yeah, it started going. Gotcha. Okay. And so you you said those eight months were tough. What was tough and how were you feeling during that time? Like tell me some stories about it. So we didn't actually get any of the like we didn't get the biggest name folks involved in the first auction. Google, Amazon, that billionaire, none of them participated in that first auction. I see. And we were like Well, our business kinda blows if we don't get those guys in'cause like Those guys are in the bulk of the auctions. Right. So we got these like piddly ones. But not the big ones. And then we were we decided to take four percent. We had no idea how much it was gonna go for.

So and oh by the way, we had a half million dollar legal bill. And how are you paying for this? Because this is such a weird company. It's such a weird company. We didn't raise any money. We self financed, but we basically just we self financed by not paying our legal bill. Don't pay your bill. Because other than that, our only expenses were Our time. Right. And flying around to these conferences meeting people. Give people a sense of were you wealthy before this? Were you doing okay? Were you broke? Yeah, no, I w I was I was fine. Like I didn't need to the previous job was like consulting or something. Yeah, so so my background like I was in consulting before

And I'd started a bunch of other random businesses that you you know. Tell me some of them. Yeah. So What was that first foray into business for you? I'd say like first of all, like I always wanted to be like a businessman. So like I joke like on my LinkedIn it used to just say businessman. Right.'Cause I I always just wanted to be a businessman. I didn't even know exactly what it meant, or you know, whatever. Like I would always be like doing stupid shit, like fixing computers as a kid. I think a lot of people have these stories. Yep were you an eBay flipper? I've noticed this with my guests. A lot of them sold. I never I didn't do much of that. I did a little bit, but no, I wouldn't call that my profession ever. Also like a timing thing. So I s but I did sell like you know, I got a CD ROM and s made C Ds and I sold to high school kids. Like these sort of small things. Sure. And then in two thousand two or something like that. Or two thousand three maybe. The iPod Mini had just come out in four different colors. It was blue, green, yellow, and pink. And

The Apple headphones at that time were really iconic, if you remember, like in the ads. That was all the ads were. It was a silhouette. With white Exactly. So they had those iconic headphones. I got this i iPod mini from my work at the time and my headphones broke. Like they I was biking and they fell on my bicycle spokes or something and like they they broke. And so I went to the Apple store. Apple wasn't selling replacement headphones at that time. So I was like, Okay I'm just gonna make headphones that look exactly the same as those headphones. And then match them in the different colors that the iPod mini is in.

So we did that, made headphones in those different colors. I like found a cheap flight to China, flew to China. Like I didn't know anything about China, but I flew I was like I knew southern China is where like how the electronics were being made. Uh twenty two, twenty three. Uh no, actually. I wasn't even twenty two, I was twenty one, I think. Yeah. And so you you're just like, Okay, I need to go figure out where these things were made. Yeah. I need to get somebody to make these the ones I want. Actually I flew to Hong Kong. There was some like electronic show that I like read about online. I was like, I'll go to this electronic show, I'll meet somebody and that'll get me in. And so I went to this electronic show uh in Hong Kong And then I did, actually. Like I met

A bun like these electronic chairs are amazing, by the way. It's just like an insane number of people selling the same shit. And like they don't speak English at at that time. So you're just like on a calculator negotiating, like in dollars. And you're just like pointing and then like yeah, they're like eight dollars and then you're like, No, fifteen cents. Right. Yeah, yeah, yeah. The difference is like a hundred. And so ultimately I got these headphones. I got these Apple headphones for eighty cents apiece. Including packaging, everything. And I did like I at this Hong Kong fair I went and I like negotiated and then I went to visit the factory. That was awesome, by the way. And then I went to this other fair called the Canton Fair.

I've heard about this. Yeah, okay. So it's the world's largest trade fair. I think it's like it's twice a year, April and October. I think three hundred thousand people go to this fair. It's in the world's largest trade convention center. It's like massive kilometer long. My friend told me this is like hundreds of football fields or something like that. Like just the fair is so big and so it's like, Oh, I'm interested in headphones or His thing with socks. And he's like, dude, there's like thousands of sock providers in a row. Like you you'll start your morning on one side and by the end you're like it's dinner time and I'm still there's more more providers here to go talk to. You can buy literally anything from like a pencil or no not even a pencil, like to the like the Cap that holds the eraser onto your pencil. You could buy like that. Container quantities. So anyway, I went to that. It was just an amazing experience. Like for a young kid. It was my first time to a like China and

I think one thing that is common in a couple of these stories, I mean we've only touched on a couple of things you've done, but you have a willingness just to get up and go. Like just go to the convention, go to the conference. Go meet like go meet him. Yeah, just try it out'cause like what's the harm? Like the harm is you fail, but then you've learned something. And I think that like I've always been willing to try stuff and it doesn't always work. And actually I I have a poor memory of like bad stuff. So like I only remember the good stuff. But like but actually in the the auction business there definitely were hard times where like me and my co founder were like at odds with each other. We were like this is really hard and annoying. And also like, you know, living in San Francisco, our bidders are all over the world. So we're like getting on calls at three AM, like All this shit. It was just like a tense time. Especially if we knew the business wasn't gonna work. And then when we had that first auction, we were like, Oh, all right, this is happening. It's on. We're gonna convince Google. We're gonna convince everyone. And it was awesome. But anyway, going back to the the headphone business, I started buying some real estate. I grew up in Pittsburgh. I bought my first house. I was twenty two years old. We live in San Francisco now, so it is unbelievable what I paid for it. Okay, so tell me. So okay, so let me tell you about the house and you guess what I paid for. So pretty hip, like up and coming neighborhood. Now

you know, fifteen years later it's like one like probably the coolest neighborhood. At that time it was like in transition. And it was a two bedroom, one bath with a garage. Small porch yard. Guess what I paid for it. Okay, so I don't know what year this was. Sounds like it was a while back. This is two thousand like four, maybe? Thousand four. Okay. So Educated guests, I think this is gonna be very cheap. I think it's gonna be like under a hundred fifty thousand dollars, maybe under a hundred thousand dollars. So I'm gonna say like eighty grand is my guess. Okay, close. Yeah, paid forty seven thousand dollars for it. So your down payment is what? Eight grand? It's like That's like one month of rent for somebody in San Francisco. And that's you like the whole house. The whole house. Yeah. It's funny because, you know, a few years ago here, I actually like I was living with a buddy some buddies of mine were paying eight thousand bucks a month in rent. Yeah. One month. And that's sort of six months of rent was the equivalent of the house that I bought in Pittsburgh. So I bought that house you bought it to live or you bought it to rent? To rent out. Okay. And you know, kind of like

did some minor fixing ups and then ultimately rented it out, like got the rent over five years, up to like eleven hundred bucks a month. So actually it was a very fast payback on the investment. And then I actually bought another house in Pittsburgh and then ended up buying realized that there's an There's a good opportunity if you buy a multi unit. So like if you buy under a four unit it's still considered residential. Yep. So you don't have to get a commercial loan, you get a residential loan, which is favorable rates. So I started I really like the idea of buying multi-units. So I bought a three unit in Chicago. And I m I had moved to Chicago, so I bought it lived there in San Francisco. I bought a four unit. Still have that one, yeah. That's a cash cow, right? Yeah, it's it's awesome. That's awesome. Uh and it's hard to find a cash cow in the bear. Yeah, because here it's an appreciation game, not a cash flow game. But you I think you got both here. Yeah, you you know like

Again, it's like I would say being willing to just go in like sometimes like the best opportunities are like there are no pictures of this thing online. Yeah. You're like, What the hell? Like what kind of stupid real estate agent doesn't put pictures of a place and then You look inside and it's gorgeous. And then you're like, Okay, that person just lost out on like like that person lost the cellar. many hundreds of thousands of dollars because like people didn't go see this place because it didn't have you know stuff like that. It's weird. Yeah. Th those are the opportunities. So when you bought this first house. You're only twenty two years old. You're buying this place. You want to rent it out. So you're thinking already, how do I get an asset? Yeah. How do I make cash flow off of it, which a lot of people who are listening to this right now

either A are already doing that or wanna do something like that. Some of it is, yeah, I need the confidence to, you know, take the leap. But the other part is like what I call the light bulb turning on. So were you reading a book and we're like, Oh, this is this is how this strategy works, because you have a mentor where your parents are telling you what's okay. So It's really weird. Like searching the internet like crazy for this. And there was this forum do you remember Fat Wallet?

Yes. Okay, it's a fat well, it was a place where you could trade like Coupons are like the best deals. They had a forum section. And actually This forum section had this one thread about

Buying a house. And like making money by buying houses. And it had like Thousands of responses. And I read this thing religiously.

before I bought this house. And I was like, this is it, this is the first house. I'm gonna do it. And it was definitely nervous. And I pushed it on there like hey guys, this is the one I'm looking at. Here's the numbers. Yeah. Yeah. Yeah, here's the numbers. Like what do you think? That's how I learned to play poker. There's two plus two forums is this long time forum on the internet. Yeah. And that's where I look you know, I would just read this thing all night. And'cause I didn't know any friends who did this. Yeah, same. I d I didn't really know people in the in the space. Yeah, actually, you know, my my dad like knew I was interested and like he had another family like we had another family friend that was interested, so he like had me go sit down with that uncle and like just learn from him for a couple of hours what he did.

And then but then this forum is really what I what I learned a lot. Right. And so that was it. That that gave me the confidence to do it. Unbelievable. Okay, so you did the you did some real estate. What were some of the other and were there any other notable businesses you did the headphones thing? How much were you making out of the headphones thing? You sort of you get you get these. Yeah, rough numbers'cause I don't remember the specifics. You know, we're buying these things for under a buck and we sold them online for depending, we sold them for like fifteen or twenty bucks. So obviously great profit margin, but we didn't really know how to market, but this is a great crash course for me on marketing. Right. So originally we only bought

a thousand headphones. So it only actually cost a thousand dollars to set up this business.'Cause you bought the headphone. I mean, obviously there's my trip to China, whatever, whatever, but like, you know, it was under it was like a few thousand dollars maybe to set up the business. And then you know, made the website and then we were trying to figure out how to market online and I'd never done it before. And I think this was at a time where there weren't like your standard ways to do it. And like Facebook wasn't really a thing. But when Facebook launched I was actually one of the first marketers on Facebook. And so here's how it worked. Actually, I think you'll really like this. So

Facebook at that time. When they launched ads for the first time. They were ads on your campus. Because remember Facebook at that time was like only within your campus. So like I went to Carnegie Mellon University. So I had access, I could put an ad and the idea was like you'd put a flyer for a party. And it it would it this is this is how like unsophisticated they were at that time. It's insane to imagine Facebook being so unsophisticated now.

But it it was like Everybody sees it, basically. It was f everybody sees it on the campus and it was five or ten dollars per day to market to everyone on your campus. And it didn't matter what campus you were at. So what I did at that time was I got friends who went to the University of Michigan And like Ohio State. And I was just like, What are the biggest universities that I have friends at? Because that's gonna be the cheapest ad space. So I got their Facebook passwords. And I posted as if I was them these ads. And that that ended up being like a clever joke. Yeah. I love that. Yeah. And so it was like just like

It like you asked about how much money we made. I I actually don't remember, but we ended up selling eleven thous I remember our first order was t one thousand headphones. Our second order was ten thousand headphones. So we bought them for nothing, like eleven thousand bucks and then You know, we sold them for whatever, a hundred and fifty plus thousand, but we spent a lot on marketing. So it was a great side business that I would say the money was really great to me at that time in my life. Yeah, in college, it's like wow, I'm if if if they make a thousand bucks a month in college, like yeah. It's an it was an insane m it was a great amount of money, but More importantly, I learned like how to market online. Right. And and like I was we were doing all sorts of other stuff. Like at that time blogs were really popular.

And that was how a lot of people got content. And so we would do like giveaways with blogs. It was just like it it was a time to experiment. I think at that time there wasn't a lot people weren't writing a lot about how to market online. Right. And so I had to like figure it out on my own, which was awesome. Yes. That's great. And so you've done a bunch of different things. And so you've you know made a little accessories company. I think you did stock option is trading at something like that. Yeah, options trading. Yeah. So this was actually like through a friend of mine. A friend of mine really got me into this. And we basically realized that you could look at mostly internet companies, you could look at like Google Trends data. And at this time, which was like near like ten years ago, the market totally was not

Correcting for this already. Right. So we would look at Google Trends data, like make an estimate on whether there were a lot of visits to that site or not. So we would we were doing things for like Priceline.com, TripAdvisor. Travel zoo like these sites. And we basically make Guesses based on this like mainly this one data source, which was like Google Trans data. This one blue squiggly line. Yeah. And we sort of like See what the analysts had recommended.

And then we basically based on Google Trends data, we were like, Okay Do we think this company is gonna outperform this quarter? And so we would do an options trade. Literally we would do it the day of earnings. And that earnings we either had made a killing or not. But we did pretty well. And I would say like with the trends data, we were probably right. Three out of five times, which if you're trading options is pretty good. Right. And so you've dabbled in all these different things from trading to real estate to starting a you know a tech business, you're an angel investor right now. You've made a podcast and sold a podcast which nobody friggin' does. So if you haven't heard the pitch, check out the pitch. It's now you sold it to Gimli. Gimli which got acquired by Spotify.

So you've done all this awesome stuff. I think it's great because it's kind of inspiring because I I myself also don't want to be one track for my whole life. Yeah. There's some things I know I'll do forever. I'll always be interested in businesses. I'll always be interested in teaching, which is kinda how I think about this podcast. Yeah. But I, you know, who knows? I might dabble in 10 different things. What's been your favorite? So most fun ones to work on. I'm curious about that. And then the second is in terms of money making, which one do you think was actually the best way to make money? Was it more investing, starting your own company, the uh online online sales of uh of different stuff, options trading, real estate. So which one was most fun? Which one was the best for money? Yeah, I'd say the most fun, like I had some pretty high highs with the auction business. And it was mainly because for the first time in my life, I felt like boy, this is something that I am really good at. And like it was really like this business development making these deals happen. So yeah, I'd say like you had to have like Some strategic thinking, like understanding of economics to build this auction model and like be a people person to connect with these people. And I felt like this was a perfect this was really good for me.

Yeah. And I had such high highs when it started to work. Like I I told you I had such low lows also like with my co founder and like but when it was working I was like, boy, for the first time in my life, you know, I was like thirty years old, thirty something, and I was like, for the first time in my life. This is what I'm meant to be doing. Something that like brings all my s like skills together and like my weaknesses are I can let go of a little bit and let other people handle it. Right. So that was a super high high. Another high high actually was not This is sort of counter to this podcast, but I spent a year volunteering in India and I was doing microfinance and I lived on a dollar a day. And actually You know, like in India it's not as hard as obviously it is here, but like

I learned a lot by that process too. And that was also just an adventure you wanted to go. It was an adventure, yeah. There was no like Calculated purpose for going down doing that. No, no, no. It was an adventure. So I'd say like recommendations wise, like Fucking choose adventure. Like So give me an example where you could have chos non adventure. You could have chose Maybe a a practical choice or a Yeah, well I mean like when I did that, I was a management consultant making a six figure salary at twenty five years old.

And I chose to move to India for zero money and It was amazing. And like How to make that decision? Like what was the what was like your thoughts? You're like, Okay, today I'm doing this, tomorrow be in India w living on a dollar a day. I was getting like annoyed at the management consulting life and As you do. As you do, as everybody who you know who's worked in banking. Consulting, like lawyer, big law. Everybody knows this feeling. And then I had seen this movie. It's called Rung Deva Santi, an Indian movie.

And it was like very inspiring to me. Yeah. So I saw this movie and I was like, I want to do something for India. And so just for background, like I grew up in America, but My parents are of Indian heritage. And I always felt a strong tie to India, even though I'd never really lived there. So I was like, I gotta do something for India. I heard about this fellowship, applied for the fellowship, and I ended up working with Kiva. Kiva.org, for those of you guys don't know. It's a really cool site. It lets you make a loan to an individual in the developing world. So for example, you can go on the site and with twenty five dollars on your credit card help a farmer in Ghana buy an irrigation pump. And you get your money back almost always. It's like ninety nine plus percent repayment rate.

But you don't get any interest. So that what you're getting up is your interest. And so you could just reinvent you could just roll it over to the next person. Right over to the next person. You put twenty five bucks in once and you might end up helping ten people over the course of a few years or whatever. That's exactly right. Yeah. As as you get paid back. So I was doing that in India and I was helping set up India for them and there were regulatory constraints anyway. But like the coolest thing was I got to experience so many different things. Like through the course of this year, I ended up we like followed people around who were like in our demographic. So I spent a day as a rag picker. So rag pickers are like the recyclers of India. They go around it's like In San Francisco you see like

these like Asian men and women like picking up the cans. In in India, it's like really poor people who like do the stuff for recycling. And so I spent a day with this like kid who was probably like eleven or twelve years old just following him around picking up rags, like learning what's recyclable, what's not. It's funny like I actually reel I learned at that time that still applies to me today, like Plastics are just not really that recyclable. And especially like

the shit we throw here, it's just actually not that recyclable. Like things you should use more like aluminum steel like stuff that that you can recycle. It was such a hard job. And I was like, Oh, for the first time in my life, this is something I really cannot do ever again. Like there was a time where we like we jumped into A dumpster. And like a dumpster in India is really fucking gross. That's exactly right. Like the street is so dirty. The dumpster is just shit. But we were you know, we went in there and I realized, man, people have really hard lives. And I think before that I didn't truly have an appreciation for how difficult other people have it. Because I you know, I grew up not in a rich family or anything, but like middle class. My parents, you know, my dad's an engineer. Never had to worry about anything in life. And this was the first time I realized, boy, like life is tough. And it made me really appreciate that and also want to like spend some part of my life

in you know helping those people or or something. So now what I do is I invest in fin tech companies. And you know, everybody like the bullshit thing is like we're making the world a better place, whatever, whatever. I c definitely can't argue that all of our investments do that, but I think we strive to try to make the world a little bit better. And it's like you know, helping underserved Could be one angle to it. It could be helping people like us, just like, oh shit, dealing with my bank sucks. Like I want a better alternative. So And do you think you'll ever jump back in the operating side? Yeah, just start another business. It's a great question. Like I'm surprised you're you've been investing for as long as you have been. Yeah, it's it's true. I I think part of The reason it's been good for me is I'm I invest really early and then have companies working out of my office. So the companies working out of my office, like every day I'm talking to them. So I get the feeling that I'm working on them and I share in s you know, some of their highs. It's not the same because like the highs are not

nearly as high. But also the lows are nearly as low. So it's kind of nice. Yeah. So so for me, I like getting my hands dirty. With the company. So I do do that and that's where I get I get some fulfillment. But I think maybe ultimately I'm really enjoying investing. I'm probably gonna be doing this for a while. You know, in retirement or something. I probably will start some other businesses. Nice. You have this investing framework, six Ts. Coining this for you. You said this it's not like super, super revolutionary. They're sort of obvious things, but I like

The sixties I think that most people It hasn't been put that way, I don't think. Yeah. And it's pretty catchy, so I like it. I don't even know if you remember all the all the sixties. I can help you I I here, I'll I'll tell you what I remember. But tell it through a story,'cause you invested in You've invested some good companies. Take, you know, investment you're really proud of. Yeah. And then walk us through the sixties and then we'll we'll wrap up after that. Sure. So we'll talk about Flexport because it's like a few billion dollar company. Flexport's amazing. Yeah. So so Flexport. For those who don't know, it's like a It started out as a customs broker and now it's like a really all things shipping company

Mostly focused on trans Pacific trade, so like US to China. And that US to China, I think, is like thirty percent of the global trade. So it's a it's a big thing. So they're connecting who? They're connect the cargo, the shippers, basically, with the people with a Customers were trying to send receive and then the brokers in between, essentially, right? Yeah, exactly right. Yeah. So I met Ryan the CEO like five years ago. How'd you meet him? You just reached out to him cold or he reached out to him. No, he friend of a friend And we met at a party and I was like, This guy's awesome. Like we shared this like love for like hacking stuff. So to give you another example, at that time we were buying AdWords with our Uber

promo codes and what does that mean? So you know how like you there's an Uber referral, you get like Ten bucks if somebody else uses your referral code. Yep. So you were just advertising. We were just advertising our referral code on Google and so we were buying Uber For twenty cents on the dollar. Great. So we like we totally bonded over these like hacky things that we love to do. And and then I was like, Okay, like when you're he was telling he he was at that time not You were doing that with him or you were doing that with your other friend? With him. Oh with him, okay. And then he was telling me like you know he wanted to start this business, Flexport before he went to Y C like all this stuff. And I was like, dude, whenever you're ready, like I'm giving you money. Yeah but no, I I said that early on and it was really strength of team. So like the first T

is team. Like this guy You know I could tell he's somebody who's gonna break through walls to to to make success happen. And not only that, like he'd already been successful. He had this other company called Import Genius. So he knew Import Genius basically a list of all of like the stuff that's being imported into the US and makes it easily accessible. And so he pr he was doing like several millions of dollars a year in that bootstrap business in revenue. And it's a r obviously a related business to his the business that he wanted to start. So like he knew what he was doing.

Team check mark. Technology. So like The second T Is there a technology need here? Fuck yeah. Like this is all a paper and pen and facts process. Old school. Old school. Customs brokers are like phone banks, like you're on the phone calling people. And so like is there a need for technology? Absolutely. Okay. Another T.

This is kind of a cheat. Total addressable market. Okay. Sure. How big is the market? How big is the market? Shipping, are you kidding me? It's a trillion dollar market. Okay. So easy. Easy check. Or three Ts on the way to six. Three Ts on the way to six. Is it six or is it five? Maybe five. Four or three? No. Traction. Traction. Yeah. So traction was one In this case, when I invest he didn't have any. And with his previous business, which was in a related space. Yeah, exactly. So you kind of like at some point you make a leap of faith and say

this guy's gonna bust through walls and get the traction. And also like early traction, if you're able to start selling into other startups. You can get that. Like I didn't have a doubt that he would be able to get that. So he did. I have the two other T's for you. Excellent, tell me. Terms. Terms. Okay, so what are the terms of the deal? Yeah, so the terms were fair. Yeah. And and you know So that investment for you now is that's a big win. It's a big win. Are you gonna make more off that than you did off any of your businesses? You might. No, probably not. But it but it it it is a very walk people through a normal angel investment. So let's say, Oh yeah, I'm listening to this podcast, I'm inspired by all these tech companies, I wanna write twenty five thousand dollar checks. Yeah. And that's what I was doing, by the way. Twenty five thousand. And you know, sometimes at at the earliest stages, like You know, I didn't have that much money. Yeah. I was like, you know, would you let me in for like they would be like Yeah, can I do 10. I'd be like, What's your minimum? And they'd be like fifty. Yeah, I'll do half that. Okay, I'll do twenty five. If you'll let me. And then you have to be like I'm gonna be so helpful to your business, whatever, whatever. I don't know if I'm doing it right. Okay, so here's how I'm thinking about tell me if I'm wrong. Yeah.

So I think that I'm gonna be writing checks that are about twenty five thousand on average. And I'm setting aside three to four hundred thousand Yeah, like okay. Ten bets or twelve, fifteen if I if some of these are lower checks, then I get to twelve, fifteen bets. And and I'm risking, you know that's gonna be less than it's gonna be like ten percent of net worth, basically. That's I think that's the right that's so I'm like, okay, if I lose it, I lose it. But that's how many bets I have. So is that you know, where were you kind of how was your calculus when you're like all right I'm gonna start writing these risky checks? I would say my calculus was similar. Similar, yeah. And then I ended up doing a lot more of them, but I had some early signs that things were going really well. Now part of it is at that time was a great time to invest as compared to today, unfortunately. Like The valuations were just so much lower. Some of these companies you know I invested in that are now billion dollar companies. I invested in at five million dollar valuations and now

those companies raising a seed round might be like twelve. And if you think about it, like that's a big thing cut your return half. And people like people really don't think about entry point valuation as much as they really should. Right. And so okay, so in in a w in a win state, you write a twenty five thousand dollar check at let's say whatever, five million valuation. Yeah. It becomes a multi becomes a billion dollar company, a one to three billion dollar company, something like that. What do you make as an angel investor on a home run like that? What is the basic thing? Yeah, yeah, yeah, sure, sure, sure. So here, let me just I I think the way I So you have to factor in a little bit of dilution. Yep. Okay, so let's say um let's say you invest at twenty five K And Uh Flexport C dron. So Flexport C dron, it was at a uh there there are many different like it was many different seeds, but like where I invest the first seed. It was a ten million dollar cap, which was very expensive at the time, but I had

Faith. And the seventh T, Faith. Faith. Faith. Faith. The heart T. Yeah. And so he's taken a lot of money in subsequently. And now it's three billion dollar company. But obviously it's not three hundred times your money. Right. Because there's been so much relation along the way. So actually Where this one sits today, I think is eighty seven times. So that twenty five thousand dollars ended up becoming over two million. Yeah. And and so some a lot of people are selling now. I'm not. I I'm still a believer in the company. So like So it could end up being more often. It could end up being a lot more. If you believe and like the company keeps to gr continues to grow, like could this be ten X? And then you're talking about Wow, that's a lot of money. Amazing. Yeah. Okay, great. And I think the last T, if I remember, that you had said was Totally Random. Totally random, so I want to we touch on it. So totally random, yeah. So it's like

When I make an investment. in a company. I'm investing in a person. Typically or people. And I wanna spend time with these people and if I can't spend time with these people, I'm not interested in investing. And it's been like, you know, the folks that I've invested in, I've like spoken at their weddings, like it's been awesome. Yeah. And like like so j Ryan, for example, like you know, his bachelor party was a month ago. We had a really good time. He's investing in my new fund. Like these are relationships that I like I wanna really cultivate. Right. And for me

I have a lot of fun talking about business, so I wanna have other friends to talk about business with. And help them or yeah, even if if I'm not helping them, I'm learning about what they do. So the totally random piece is like are these Cool people. Like can I have random discussions with them and have a good time. Awesome. Dude, you have a hell of a story. I'm really glad we did this. Caught you when you were back in town because you travel all around the world. I following you on Facebook is like following the National Geographic. It's like oh he's in a tunnel in Egypt and he's posting a photo. Then he's like, you know, at the top of this tower in Moscow or wherever you are a traveler. Um all right, so this was awesome.

If somebody listens to this and they wanna either help you, get in touch with you, something like that, how should people follow you, find you? Twitter is good or you can email me. What's your Twitter handle? At P Thisy P I T D E S I So for those of you don't know, so I grew up in Pittsburgh, so Pitt and then this he This he's like short for Indian. Yeah. And this is like totally lame, but I I've had it since eighth grade. So it was my AOL screen. Most of us knew to shed that in like college. We were like, Oh wait, that was stupid. I'm no longer mine was Mr. Goobople. So I'm no longer Mr. Gooble. I don't even know what that was. But I got rid of it. Twitter's easy email. I'm starting a new fund and just starting to fundraise for it. It's called Better Tomorrow. Yeah. And I'm Sheel at btv.vc.

Okay. I'm gonna invest in your fund. Awesome. Great. Let's do it. That's fine, man. Dale, dale, dale

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