EPISODE
18

#18 - The Big Business of Wacky Domains

Oct 16, 2019·57:00·Sam & Shaan·with Sheel Mohnot·Listen·AppleSpotify
0:0028:3057:00
16 moments · 335 paragraphs · synced to the second

I sold internet real estate to the tune of half a billion dollars worth. .app, .blog, .church. Some of these you've probably seen. My company was responsible for selling a lot of those. It's what's called an ascending clock second price auction. The way it works is, in this case, every 20 minutes increments up and it's ascending. We'd start the bidding at $200,000 times the number of bidders, $600,000 to start. Every 20 minutes it goes up by $600,000 with a minimum increment of 20%. You know, once we get to $3.6 million, it goes up higher.

SHAAN

Your top auctions went for how much? What is it, like $10 million, or is it more like—

it's over $100 million.

SHAAN

Sheil, you're here.

Yeah.

SHAAN

Did you bring your A-game?

Always bring my A-game.

SHAAN

All right. Do you stretch in the mornings? Do you eat your breakfast? What do you do to get going in the morning?

I actually eat no breakfast, drink no coffee ever.

SHAAN

So you're a faster now. Intermittent fasting. That's not what you've called it. You happen to not eat breakfast.

I just happen 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.

SHAAN

It's awesome. Great. And so you're here to tell your story. I met you maybe 4 or 5 years ago. I don't remember how long it was.

Yeah, probably.

SHAAN

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. I don't know what happened. Yeah, but I remember sitting at the bar in our office.

I do.

SHAAN

Yep. And you told me one of the craziest stories of how you— of how someone made it that I've met here in San Francisco. So million-dollar question. You've made a million bucks. How did you do it?

SHAAN

Gotcha. Okay. If I wanted to create Sean.com, which I do, and was taken, and so I was like, okay, shit, what do I want to be instead? I can do Sean123.com. That's less cool. Could I get Sean.co? Could I get Sean.xyz? Sean.xyz, Sean.badass, whatever, right? So these other domains, these other dot-whatevers exist now, and you were responsible for selling them 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 .com, not .co, but like what are some of the other big ones?

So .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 going to be a big one. I think .blog potentially, although blogs have gone decreased in value since this whole thing came out. .xyz is a friend of mine owns, and his thing is the alphabet ends in .xyz. Why shouldn't your domain name? Okay. You made a bet on that.

SHAAN

Yeah. 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 2012, 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 wanna do something like in the crypto space, like .ptc. Unfortunately in 2012, nobody did that. In 2012, you had to apply. You had to pay $185,000 to apply for your own .whatever. So what would you apply for?

SHAAN

So like, I would— I mean, the first one that comes to mind is like porn, basically. Right? Like, what's the most popular thing on the internet? Like .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. They can come to me, and I can sell them their other domains, essentially.

That's exactly right. Yeah. ICANN, which is the governing body of the internet, actually made an exception and like a while ago created .xxx.

SHAAN

How do they decide which of these are going to exist? Because some of these are actually country codes, right?

Like, so all of the two-letter ones, .co, .vc, .tv, they're all country codes. So .vc is Saint Vincent and the Grenadines.

SHAAN

Oh, really? What's TV?

Tuvalu.

SHAAN

I don't even know what that is.

Okay, great. .io is like the British Indian Ocean Territories.

SHAAN

Gotcha. So they— so under the premise of every country can have their own. Yeah. It actually immediately got co-opted by business to be like, great, .tv.

Yeah.

SHAAN

Sports.

And remember, remember, like 10 years ago there were all these like .ly domains. That's Libya. You're supporting Libya.

SHAAN

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 .co domain, that's Colombia.

SHAAN

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 country— you know, how much the countries make off— like, how much did Libya make off of all the .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 could easily do the math, but it's in the hundreds of millions that they've made.

SHAAN

Wow. Okay. So this is the country ones. And then they started doing just words like .app.

Yeah. So the way this thing worked was in 2012, you had to apply for your own .whatever. So let's say that me and you applied for .app. You had to pay $185,000 just to apply. And by the way, they got 2,000 applications, which means they made $360 million in application fees.

SHAAN

Wow.

And if you were the only one that applied for .app, you got it. It was yours. You paid $185K one time and then, you know, some ongoing fees, but it was yours. And then, by the way, you could sell everything .app, like Facebook.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 we use as a third party?

SHAAN

So me, you, and Donald Trump get into a bidding war.

Me, you, and Trump. So me, you, and Trump all—

SHAAN

we're just doing this so I could beat Trump. Yeah.

So me, you, and Trump allwant.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. Okay. But ICANN prefers that we sort it out amongst ourselves. So what happens next? So you go to Donald Trump and you say—

SHAAN

Well, we first ante up our fee. We each put $185K in just to say—

That was just the application fee. So that's basically a sunk cost. Right. 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 going to get this. Right. 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, you, and Trump, although kind of similar. They are 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 $180 million, like seed round. Effectively, just, just for this.

SHAAN

Okay. So me, you, and Trump, we go into the bidding war.

Yep.

SHAAN

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? He wrote The Art of 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 an ascending clock second price auction. What does that mean? 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 20 minutes it increments up and it's ascending.

SHAAN

Okay.

Simple. So in a 3-party auction, we'd start the bidding at $200,000 times the number of bidders. So it'd be $600,000 to start. Every 20 minutes it goes up by $600,000 with a minimum increment of 20%. You know, once we get to $3.6 million, it goes up higher. Okay. What's your willingness to pay? Okay.

SHAAN

So I'm willing to pay right out the gate. And now my strategy, should I be telling my top bid or my like lowball offer?

So you, for the sake of this, you're gonna tell us your top bid. Okay. But in the actual auction, you'd only say whether you're in on each round or not.

SHAAN

Okay, cool. So let's say I'm willing to pay up to $10 million to get .app.

$10 million. 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 $5 million. Okay. And then my willingness to pay, like, I think .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, like 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 going to say I'd be willing to pay like $12 million. Okay. So in this auction, what's going to happen is we're going to start the bidding at $600,000.

SHAAN

And we should 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. Let's say Donald Trump was actually only in for $500,000 in the first increment. He would say, I'm out, and I'm in for $500,000. Right. 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 $10 million.

SHAAN

Ah, okay. So you were, you were willing to be in at $10. You might have continued to be in up till $12.

I would've been, but nobody knows that.

SHAAN

Nobody else is there. Yeah. Nobody knows. Nobody knows what your real number's gonna be.

Exactly.

SHAAN

Okay.

And then, so I pay $10 million bucks, but the real beauty of this auction is where the $10 million goes. So who gets the money?

SHAAN

Well, nobody owns that app. So is it ICANN that gets it? I don't know who gets the money.

So a lot of people would think ICANN gets the 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 $10 million that I paid— go away. Yeah, we pay— we're paying you off effectively to go away. And really what this is, is like anytime 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, 50/50 JV, right? How would we decide, like, how much would I have to pay you to, like, give you 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.

SHAAN

So they actually get the money.

They get the money. So I'm paying you guys each $5 million minus my auctioneer fee, which would be in this case $400,000. So we took 4% of the auction fee.

SHAAN

Wow. So the first thing is Were there people who just went into the auctions trying to get paid out, trying to lose?

You couldn't because you had to apply basically a year before any of this, like, before you knew how the auctions would work.

SHAAN

Yeah. Oh, okay. Okay. That's cool. So that already prevented that from happening. The second thing was your top auctions went for, you know, how much? What is it like $10 million or is it more like $100 million?

SHAAN

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 $100 million auctions. Certainly there was something in between where you were like, okay, how does this work?

Totally.

SHAAN

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?

SHAAN

Okay.

And how do we build any credibility in this industry? Nobody knows us. So we did a couple of things that I think worked really well in our favor. A, like, you know, our co-founder is a PhD from Stanford in auction theory.

SHAAN

And this was just a buddy of yours or?

Buddy.

SHAAN

Yeah.

Actually, there's another totally random story, but I met my co-founder on a train in India in 2006.

SHAAN

Just sat next to him.

He kind of— wow. It turned out he was a friend of a friend, but he's like a German dude.

SHAAN

Right.

And I was traveling in India. We ended up on this like 40-hour train ride together, became really good friends, have like worked together a bunch of times since.

SHAAN

Wow. Okay. All right. That's amazing.

Then—

SHAAN

and that's also funny how common that is, how common the randomness is. Yeah. Your buddy knows a lot about auction theory.

Yeah.

SHAAN

And so how did you, how did you even know that the companies were gonna have trouble sort of sorting this out amongst themselves? 'Cause 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 talked 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 wanna work with you. And in fact, like, for a long time it looked like this business was gonna be a total goose egg.

SHAAN

You did what there? You emailed the lawyers, you were calling somebody? Yeah.

Emailed, called, like show up in person. Yep. Like, so they had these conferences 3 or 4 times a year. We'd go to all the conferences and the domain conferences. Domain conferences.

SHAAN

Okay. Nice. Must be a— 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.

SHAAN

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 got to just get in front of these people. And so I literally just like looked up everyone who had not responded to me. Yeah. 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.

SHAAN

Okay.

Because 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 so you need these auctions. Some of them were like 13 or 14 parties.

SHAAN

Right.

So if I got, if I got 13 of the 14, I don't have an auction. I have no money. Mm-hmm. But if I get 14, 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 him this whole time. I was like, just shooting the shit. And then ultimately, like, you know, became friendly with this guy and 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 amenable. He like started talking.

SHAAN

That's amazing. 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 heard. Okay, so 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. He 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?

SHAAN

They want to make money, get the 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 Justice was against what we were doing. I see. And so that made Google a lot more suspect. Of us.

SHAAN

Right.

And, you know, they don't want to do anything that could potentially be afoul 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, I 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.

SHAAN

And why did they ultimately come around? So 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, 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.

SHAAN

Seems like— seems like a terrible business, but I love that it worked out. So what was it 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 going to— you're not going to 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 them of 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.

SHAAN

And is this a piece of software or what? 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 deposit. And we have, because the bidders are so international, they're in accounts all over the world. Right. 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. Oh wow. So we're holding like hundreds of millions of dollars in escrow. In accounts, like in Hong Kong. It's kind of nuts.

SHAAN

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.

SHAAN

So I didn't know how any of this shit works, but 4 or 5 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 is going to 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 80 to 100 million people. Maybe there's some value in this. And hey, wouldn't it be cool if we could turn this around? It was more really that. It was like, would it be 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. Because 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 through 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 got to go to LA. And what we're going to try to do is we're going to try to buy it out of bankruptcy, essentially. And we just had 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? There's like, 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 could 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 going to work. I assume the judge is going to say something. The judge immediately just says, all right, you 3 companies are here to buy this. Go in that room over there. Sort it out amongst yourselves. This is kind of 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 prize. And we were 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.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 this table. I have no idea what's going to happen. I hoped it was a process like what you're talking about with some structure. Yeah. And like like, you know, whatever. And instead it's like, okay, so what's the starting bid? Uh, we'll start the bid at, uh, $150,000.

Okay.

SHAAN

And we're like, so somebody says $150,000, we're like, we'll do, and they just had some minimum, like you have to go up by whatever. I was like, all right, we'll do $180,000. We'll do $230,000, whatever. It just kept going up.

And did, wait, so at this point, did you have a number in your head?

SHAAN

Yeah. 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, like the domain name, the domain, the, servers, the lists, you know, stuff like that.

$500,000 or something.

SHAAN

This might be half a million bucks.

Half a million bucks.

SHAAN

Okay. Optimistically, half a million, maybe it's $350,000, whatever. We were talking about that. And then Michael, you know, in his wisdom was like, look, I don't think we're going to go in and we're going to be able to get this for like $300,000 or $400,000. 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 going to go for $1 million and I'm willing to pay $1 million.

Yeah. For him, there's emotion tied into it too. Like it was his baby. Exactly.

SHAAN

So he was like, I'm willing to pay $1 million. And we're like, okay, well, I guess that's our strategy now. So in my head, I'm like, $1 million. I have no idea what these other guys are thinking. And we sit down and so starts going up, starts creeping up at about 350,000. Tagged is like, you could tell this guy was like, I flew to LA. I thought like nobody would be here.

Yeah.

SHAAN

What the hell am I getting myself into? Yeah. 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, and everybody's going up in very even increments of like whatever the first person threw out was like 30,000 more or something like that. The next That's just how it went up every time. Every time. And a lot of— everyone tries to have like a poker face about themselves. And at about $700,000, they like stepped out of the room to be like, we need to make a phone call. Is that okay? We're like— the mediator was like, yes, no problem. You can take a break. So they go out, take a phone call, and I huddle up with the lawyer. I'm like, okay, this looks like this is probably what they were pre-approved for because they got to go call their boss. Yeah. To figure out what they can do. They're either going to come back and say, no, take it. Fantastic. Or they're going to come back with a new kind of like top price in their mind. And so that's probably going to be an even number. So just test like every time it gets to $800, $900, or $1 million, don't let them get that number. Like jump above it a little bit.

A little bit.

SHAAN

And I talked to the mediator. I was like, hey, look, they can't do this again. And she's like, yeah, okay, we're not going to do any more. We're not going to do any more breaks. That interrupts the process.

So then you knew that they had an upper limit. And if you go a little bit above that upper limit, it's yours.

SHAAN

Exactly. And I went— I went outside to try to make small talk with them too, to be like, man, what are you guys going to 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.

SHAAN

They just wanted the SEO and they wanted some other benefits. So I was like, okay, these guys aren't super 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 at 900-something and she just, our lawyer just jumped and went 1 million and 15,000 and just threw 15,000 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.

Yeah.

SHAAN

And he's like, we just didn't know how far you guys would go. And I told him, I was like, dude, our guy's like emotionally attached to this. Like he's gonna kill keep going, you should just drop out now before like, you know, this gets outta 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.

SHAAN

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. Put my max.

SHAAN

Yeah, that's brilliant. Okay, and you didn't invent that, you just took an—

that's like a known auction theory thing. And like eBay auctions, if you actually can bid as high as you want and you'll pay increment, one increment over the next highest bid, right? So that's like a standard auction theory thing. We didn't invent it.

SHAAN

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.

Yeah.

SHAAN

To like your first auction, how long was that? Because I like to give people a sense of like how long business takes to actually mature. Because when we say it sounds bang, bang, bang. Yeah, things do take time.

I think it took like 8 months and that was a very difficult 8 months. Yeah. Like we really didn't think it was going to 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 8 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 .vote, .photography, .now, .red. Like they're, these were the ones in the first auction that we did. And so like .photography, I'll use this as an example. How much do you think .photography went for?

SHAAN

Geez, I have no frame of reference. Like I don't even know what you can make off these. So I mean, I'll throw a number out there just to be wrong. I don't know. So I would say .photography, somebody's going to pay $15 million 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 .photography. Like who's going to use .photography? Yeah. Like it's such a long name. Like when you're used to like a 3-letter TLD or 2-letter even for the country codes, like .photography is really long. But actually it turns out that photographers want to be like, they like their name .photography, right? They don't want their name .photo cuz that seems unprofessional. So they like their name .photography or like wedding.photography or like sanfranciscowedding.photography, all these names. I'm not gonna tell you exactly how much it costs, but let, let's say it costs $3 million, right? So when people learned of this, they were like, somebody paid $3 million for .photography? That makes no sense. But in that first year, they were selling these names for like $50, a .photography name, and they sold like 100,000 in that first year. In the first year, they made $5 million out of it. And then if you think about it, recurring, 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?

SHAAN

And so that set the tone then for you guys.

Yeah. And then, and there were peaks and valleys of like after that first auction and then 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 because they were the first names, the first new names sold and there are 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 down.

SHAAN

Gotcha. Okay. And so you said those 8 months were tough. What was tough and how were you you feeling during that time? Like, tell me some stories about—

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 kind of blows if we don't get those guys in because like those guys are in the bulk of the auctions, right? So we got these like piddly ones, right? But not the big ones. And then we were— we decided to take 4%. We had no idea how much it was going to go for. So, like, and oh, by the way, we had a $500,000 legal bill.

SHAAN

So how are you paying for this? Because this is such a weird company.

It's such a weird company. So we didn't— we didn't raise any money. We self-financed, but we basically just— we self-financed by not paying our legal bill.

SHAAN

Right. You're like, this is easy. Don't pay your bill. Yeah. Funding. You don't need funding.

Yeah. Because other than that, our only expenses were like our time. Time, right? And flying around to these conferences, meeting people.

SHAAN

Give people a sense of, were you wealthy before this? Were you doing okay? Were you broke?

Because I know I was, I was fine. Like, I didn't need—

SHAAN

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 know, tell me some of them. Yeah.

SHAAN

So what was the first foray into business for you?

I would 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. 'Cause like 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.

SHAAN

Yep. Were you an eBay flipper? I've noticed this with my guests. A lot of them sold stuff online on eBay or—

I never, I didn't do much of that. I did a little bit, but not, I wouldn't call that my profession ever. Also like a timing thing. So I, but I did sell like, you know, I got a CD-ROM and made CDs and I sold to high school kids like these sorts of small things.

SHAAN

Sure.

And then, in 2002 or something like that, or 2003 maybe, the iPod Mini had just come out in 4 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.

SHAAN

That was all the ads were. It was a silhouette with white headphones.

Exactly. So they had those iconic headphones. I got this 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 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's 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 all the electronics are made. Uh, 22, 23. Uh, no, actually I wasn't even 22. I was 21, I think.

SHAAN

Yeah. And so you, you're just like, okay, I need to go figure out where these things are made.

Yeah.

SHAAN

I need to get somebody to make these, the ones I want.

Actually, I flew to Hong Kong. There was some like electronics show that I like read about I was like, I'll go to this electronics show, I'll meet somebody, and that'll get me in. And so I went to this electronics show in Hong Kong, and then I did actually, like, I met a bunch, like, these electronics shows are amazing, by the way. Like, it's just like an insane number of people selling the same shit. And like, they don't speak English at that time. So you're just like on a calculator negotiating like in dollars. Pointing. And you're just like pointing and then like, you know, they're like $8 and then you're like, no, 15 cents.

SHAAN

Right.

Yeah. Yeah.

SHAAN

The difference is like 100x.

Yeah. And so ultimately I got these headphones. I got these Apple headphones for $0.80 apiece, including packaging, everything. And I did like I at this Hong Kong fair, I went, I like negotiated and I went to visit the factory. That was awesome, by the way. And then I went to this other fair called the Canton Fair.

SHAAN

I've heard about this.

Yeah. Okay. So it's the world's largest trade fair. I think it's like this twice a year, April and October. I think 300,000 people go to this fair. It's in the world's largest trade convention center. It's like massive kilometer-long.

SHAAN

Yeah, my friend told me this is like hundreds of football fields or something.

Hundreds of football fields. That's exactly right.

SHAAN

Like, just the fair is so big. And so it's like, oh, I'm interested in headphones, or his thing was 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.

You can buy literally anything from like 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 in a piece container quantities.

SHAAN

Dude, I have to go to the Canton Fair.

You could buy like construction equipment, like you can buy everything there, um, in 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 like China and I learned a lot.

SHAAN

You're kind of fearless. I think one thing that is common in a couple of these stories, I mean, we've only touched on a couple 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, just 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 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, 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 3:00 AM, like all this shit. It was just like a tense time. Yeah. 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. Yeah. 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. Okay. I bought my first house. I was 22 years old. We live in San Francisco now, so it is unbelievable what I paid for it. Okay, so talk to me. So, okay, so let me tell you about the house and you guess what I paid for it. Okay. So pretty hip, like up and coming neighborhood. Now, you know, 15 years later, it's like one, like probably the coolest neighborhood. At that time it was like in transition and it was a 2-bedroom, 1-bath with a garage, small porch, yard. Yeah. Guess what I paid for it?

SHAAN

Okay. So I don't know what year this was. Sounds like it was a while back.

This was 2000, like, 2004, maybe.

SHAAN

2004. Okay. So educated guess, I think this is going to be very cheap. I think it's going to be like under $150,000, maybe under $100,000. So I'm going to say like $80,000 is my guess.

Okay. Close. Yeah. I paid $47,000 for it.

SHAAN

So your down payment is what, $8,000?

Yeah. Yeah.

SHAAN

Yeah.

It's hilarious, right? It's like, that's like one month of rent for somebody in San Francisco. And that's like the whole house. The whole house. Yeah. It's funny because, you know, a few years ago here, actually, like I was living with a buddy, some buddies of mine, we were paying $8,000 a month in rent. Yeah. One month. Month. And that's sort of 6 months of rent was the equivalent of the house that I bought in Pittsburgh. So I bought that house.

SHAAN

You bought it to live in 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 5 years up to like $1,100 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 4-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 liked the idea of buying multi-units. So I bought a 3-unit in Chicago and I, I, I had moved to Chicago, so I bought it, lived there. Yeah. Here in San Francisco, I bought a 4-unit.

SHAAN

Yeah. You were telling me you still have that one, right?

Still have that one.

SHAAN

Yeah. That thing's a cash cow, right?

Yeah. It's, it's awesome.

SHAAN

That's awesome.

Uh, and it's hard to find a cash cow in the Bay Area.

SHAAN

Yeah. 'Cause here it's an appreciation game, not cash flow. Slow game, but 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. You know? Right. You're like, what the hell? Like, what kind of stupid real estate agent doesn't put pictures of a place? Right. 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 seller many hundreds of thousands of dollars because, like, people didn't go see this place because they didn't have, you know, stuff like that. It's weird. Yeah. Those are the opportunities.

SHAAN

So when you bought this first house, you're only 22 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.

SHAAN

How do I make cash flow off of it? Which a lot of people who are listening to this right now, they're either A, are already doing that or want to do something like that. Yeah. 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 were like, oh, this is, this is how this strategy works. Did you have a mentor? Were your parents telling you what to do? Yeah.

Okay. You know, it's really weird. I was just like searching the internet like crazy for this. And there was this forum. Do you remember Fat Wallet? Yes. Okay, so Fat Wallet was a place where you could trade like coupons or 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 going to do it. And it's definitely nervous.

SHAAN

And you posted 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?

SHAAN

That's how I learned to play poker. There's 2+2 Forums is this long time forum on the internet. Yeah. And that's where I, you know, I would just read this thing all night and because I didn't know any friends who did this.

Yeah, same. I didn't really know people in the, in the space. Yeah, actually, you know, my dad had, 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— where I learned a lot. Right. And so that was it. That gave me the confidence to do it.

SHAAN

Unbelievable. Okay, so you did the— you did some real estate. What were some of the other— 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. So, yeah, rough numbers because I don't remember specifics. You know, we were buying these things for under a buck and we sold them online for— depending, we sold them for like $15 or $20. 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 1,000 headphones, so it only actually cost $1,000 to set up this business because you bought the headphones. 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.

SHAAN

Okay.

'Cause 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, this is, this is how like unsophisticated they were at that time. It's insane to imagine Facebook being so unsophisticated now.

SHAAN

Right.

But it, it was like everybody sees it basically. It was, everybody sees it on the campus and it was $5 or $10 per day to market to everyone on your campus.

SHAAN

And it didn't matter what campus you were at.

SHAAN

Yeah. I love that.

Yeah. And so it was like, just like, like you asked about how much money we made. I actually don't remember, but we ended up selling 11,000. I remember our first order was 1,000 headphones. Our second order was 10,000 headphones. So we bought them for nothing, like $11,000. And then, you know, we sold them for whatever, $150,000 plus. 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.

SHAAN

Yeah. In college, it's like, wow, I'm— if you make $1,000 a month in college, like, Yeah, it was an insane—

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 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.

SHAAN

Awesome. Yes, that's great. And so you've done a bunch of different things. And so you've made a little accessories company. I think you did stock options, you did trading at some point?

Yeah, options trading. Yeah. So this is 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 10 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, we were doing things for like priceline.com, TripAdvisor, Travel Zoo, like these sites. And we'd basically make guesses based on this, like, mainly this one data source, which was like Google Trends data.

SHAAN

This one blue squiggly line.

Yeah. And we'd sort of like see what the analysts had recommended. And then we basically, based on Google Trends data, we were like, okay, Hey, do we think this company is going to 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, right? But we did pretty well. And I would say, like, with the trends data, we were probably right 3 out of 5 times, which, if you're trading options, is pretty good, right?

SHAAN

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. Yeah. You've made a podcast and sold a podcast, which nobody freaking does. That's true. If you haven't heard the pitch, check out the pitch. It's now— you Sold it to Gimlet.

Gimlet, which got acquired by Spotify.

SHAAN

So you've done all this awesome stuff. I think it's great because it's kind of inspiring cuz I, I myself also don't want to be one track for my whole life.

Yeah.

SHAAN

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 kind of how I think about this podcast.

Yeah.

SHAAN

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, of different stuff— options trading, real estate. So which one was most fun and 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 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 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 30 years old, 30-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 skills together and like my weaknesses 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.

SHAAN

And I think it's just an adventure you wanted to go on.

It was more of an adventure.

SHAAN

Yeah. There was no like calculated purpose for going and doing that.

No, no, no. It was an adventure. So I'd say like recommendations-wise, like fucking choose adventure.

SHAAN

Like, so give me an example where you could have chose non-adventure. You could have chose maybe 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 25 years old, and I chose to move to India for zero money and it was amazing.

SHAAN

And like, how did you make that decision? Like, what was the— what was like your thought process? You're like, okay, today I'm doing this. Tomorrow I'm going to be in India living on a dollar a day.

Yeah, I was getting like annoyed at the management consulting life. And as you do, as you do, as everybody who, you know, has worked in banking, consulting, like lawyer, big law, everybody knows this feeling. And then I had seen this movie, it's called Rang De Basanti, an Indian movie, and it was like very inspiring to me. 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 got to do something for India. 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 $25 on your credit card, help a farmer in Ghana buy an irrigation pump and you get your money back almost always. It's like 99+ repayment rate, but you don't get any interest. So what you're giving up is your interest.

SHAAN

And so you could just reinvest, you could just roll it over to the next person, roll it over to the next person.

You put $25 in once.

SHAAN

And you might end up helping 10 people over the course of a few years or whatever.

That's exactly right. Yeah. 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 concerns 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 ragpicker. So ragpickers 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. Yeah. In, in India it's like really poor people who like do this stuff for recycling. And so I spent a day with this like kid who was probably like 11 or 12 years old, just following him around, picking up rags, like learning what's recyclable, what's not. It's funny, like I actually real— I learned at that time that still applies to me today. Like plastics are just not really that recyclable. Yeah. And especially like the shit we throw here, it's just actually not that recyclable. Like things you should use more, like aluminum, 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. Like the street is dirty. The street is—

SHAAN

imagine the dumpster.

That's exactly right. Like the street is so dirty. The dumpster It's 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 is the first time I realized, boy, like, life is tough. And it made me really appreciate that and also want to like I would like spend some part of my life in, you know, helping those people or something. So now what I do is I invest in fintech companies and, you know, everybody like the bullshit thing is like we're making the world a better place, whatever, whatever. I 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. Yeah. 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.

SHAAN

So do you think you'll ever jump back in the operating side? Start another business?

It's a great question.

SHAAN

Like, I'm surprised you've been investing for as long as you have been.

Yeah, it's true. I think part of the reason it's been good for me is 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, 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 not 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 going to be doing this for a while, you know, in retirement or something. I probably will start some other businesses.

SHAAN

Nice. You have this investing framework, 6Ts.

You found it online.

SHAAN

I'm coining this for you. You've said this, it's not like super, super revolutionary. They're sort of obvious things, but I I like the 6 Ts. I think that most people— it hasn't been put that way, I don't think. And it's pretty catchy, so I like it. I don't even know if you remember all the 6 Ts.

No, I'm like, man, what are they?

SHAAN

I can help you.

Here, I'll tell you what I remember.

SHAAN

But tell it through a story, because you invested in— you've invested in some good companies. Take an investment you're really proud of and then walk us through the 6 Ts, and then we'll wrap up after that.

Sure. So we'll talk about Flexport, because it's like a few billion dollar company.

SHAAN

Flexport's amazing.

Yeah. So Flexport

SHAAN

for those who don't know.

For those who don't know, it's like 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 30% of global trade. So it's a, it's a big thing.

SHAAN

So they're connecting who? They're connecting the cargo, the shippers basically with people, with the customers who are trying to send, receive, and then the brokers in between essentially, right?

Yeah, exactly right. Yeah. So I met Ryan, the CEO, like 5 years ago.

SHAAN

How'd you meet him? You just reached out to him cold or he reached out to you?

No, no, 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, there's an Uber referral? You get like $10 if somebody else uses your referral code.

SHAAN

Yep.

So you were just advertising. We were just advertising our referral code on Google. And so we were buying Uber for 20 cents on the dollar.

SHAAN

Great.

So we like, we totally bonded over these like hacky things that we love to do. Yeah. And, and then I was like, okay, like when you're— he was telling me he was at the time not—

SHAAN

you were doing that with him or you're 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 YC, like all this stuff. And I was like, dude, whenever you're ready, like I'm giving you money. Yeah. But you know, I said that early on and it was really strength of team. So like the first T is team. Okay. Like this guy, you know, I could tell he's somebody who's going to break through walls 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 in the US and makes it easily accessible. And so he was doing like several millions of dollars a year in that bootstrap business. $1 million in revenue. And it's obviously a related business to the business that he wanted to start. So like he knew what he was doing.

SHAAN

Team checkmark.

Team checkmark. Technology. So like the second T, is there a technology need here? Fuck yeah. Like this is all a paper and pen and fax 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.

SHAAN

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.

SHAAN

3 Ts on the way to 6.

3 Ts on the way to 6. Is it 6 or is it 5? Maybe 5 or 3. Maybe it's just 3.

SHAAN

No, no, no. Traction.

Traction. Yeah. So traction was one. In this case, when I invested, he didn't have any. Right.

SHAAN

And but 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 going to 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.

SHAAN

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—

SHAAN

that's a big win.

It's a big win.

SHAAN

Are you gonna make more off that than you did off any of your businesses? You might.

No, probably not. But it is a very—

SHAAN

people through a normal angel investment. So let's say, oh, I'm listening to this podcast, I'm inspired by all these tech companies. I want to write $25,000 checks.

Yeah. And that's what I was doing, by the way, $25,000. And, you know, sometimes 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 $10,000? I'd be like, what's your minimum? And they'd be like, $50,000. I'll do half that. Yeah, I'll do half that. Okay, I'll do $25,000 if you'll let me.

SHAAN

Okay.

And then you have to be like, I'm going to be so helpful to your business, whatever, whatever.

SHAAN

Because I'm doing some angel investing now, but I don't know if I'm doing it right. Okay, so here's how I'm thinking about it.

Tell me if I'm wrong.

SHAAN

Yeah. So I think that I'm going to be writing checks that are about $25,000 on average, and I'm setting aside $300,000 to $400,000 to do it. I'm like, okay, that's like 10 bets or 12, 15. If some of these are lower checks, then I get to 12, 15 bets. And I'm risking, you know, let's say that's going to be less than— it's going to be like 10% of net. Net worth, basically.

That's— I think that's right.

SHAAN

That's— 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.

SHAAN

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 $5 million valuations. And now now those companies raising a seed round might be like $12 million. And if you think about it, like, that's a big difference.

SHAAN

That's your return in half.

Yeah, in half. And people, like, people really don't think about entry point valuation as much as they really should, right?

SHAAN

And so, okay, so in a, in a win state, you write a $25,000 check at, let's say, whatever, $5 million valuation. Yeah, you— it becomes a multi— becomes a billion-dollar company, a $1 to $3 billion company, something like that. What do you make as an angel investor on a home run like that? What is the base?

Yeah, yeah, sure, sure. So here, let me just— I think the way—

SHAAN

So you have to factor in a little bit of dilution.

Yep. Okay. So, so let's say, let's say you invested $25K in Flexport seed round. So Flexport seed round, it was at a— there are many different— like it was many different seeds, but like where I invested the first seed, it was a $10 million cap, which was very expensive at the time. But I had faith. I had faith in Ryan and the 7th T, faith. Faith. Faith.

SHAAN

Faith.

The hard T. The hard T. Yeah. And so he's taken a lot of money in subsequently and now it's $3 billion company, but obviously it's not 300 times your money, right? Because there's been so much dilution along the way. So actually where this one sits today, I think is 87 times. So that $25,000 ended up becoming over $2 million.

SHAAN

$25 grand turns into over $2 million.

Yeah. And, and so some, a lot of people are selling now. I'm not, I'm still a believer in the company.

SHAAN

So like, so it could end up being more of, it could end up being a lot more if you believe and like the company keeps to—

continues to grow, like, could this be 10x? And then you're talking like, wow, that's a lot of money for an individual.

SHAAN

Yeah, 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 make sure 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 want to 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. And like, like, so 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 want to really cultivate. Right. And for me, I have a lot of fun talking about business. So I want to have other friends to talk about business with and help them. Even if I'm not helping them, I'm learning about what do. So the totally random piece is like, are these cool people? Like, can I have random discussions with them, right, and have a good time?

SHAAN

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. Following you on Facebook is like following the National Geographic. It's like, 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.

SHAAN

All right, so this is awesome. If somebody listens to this and they want to, you there, 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.

SHAAN

What's your Twitter handle?

@PitDesi, P-I-T-D-E-S-I. So for those of you who don't know, so I grew up in Pittsburgh, so Pit, and then Desi. Desi is like short for Indian. And this is like totally lame, but I've had it since 8th grade. So it was my AOL screen name.

SHAAN

You kept your AOL handle.

I kept my AOL handle.

SHAAN

Most of us knew to shed that in college. We were like, oh wait, that was stupid.

Stupid.

SHAAN

I'm no longer— mine was Mr. Goobapple. So I'm no longer Mr. Goobapple. I don't 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 shiel@btv.vc.

SHAAN

Okay. I'm going to invest in your fund.

Awesome.

SHAAN

Great. Let's do it.

That was fun, man. Dollar, dollar, that's what I need. Said I need dollar, dollar, dollar, that's what I need. And if I share with you my story, would you share your dollar with me?