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Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers, to tease out the habits, routines, lessons learned, et cetera, that you can apply to your own lives. And of course, I interview experts across a very wide range of areas. They could be in the military. They could be chess grandmasters. They could be athletes. They could be actors. They could be CEOs.
And in this case, we have a polymath who one could argue was the king of Hokkaido scallops. What the hell does that mean? Well, we get into it in the conversation. He has an eclectic bio, Andrew Rosner, Andrew is the founder and CEO of Media Options, which has been the number one domain broker in the world for the last six consecutive years. We talk about a lot more than domains and his life trajectory, his adventures are
Amazing. His mentors are characters to put it mildly, but let's focus on the bio. Since 2008, Andrew has been involved in more than $600 million in domain sales and has played a pivotal role in numerous high-profile domain name transactions, including x.com to Elon Musk,
Zoom.com to zoom and prime.com and podcast.com to Amazon as well as thousands of others. So we get into how this business works, what the ecosystem looks like, what best practices look like, what differentiation looks like. And we also talk about all of those things and how he cut his teeth in the seafood arbitrage business and in other areas.
Andrew is an inductee of the domain name Hall of Fame. He was named Domain Investor of the Year by Traffic, and he is the creator of the Rosner equation, which he did not name himself. It was named after him a formula for objectively valuing domain names, widely adopted by the industry.
Andrew is also the owner of domain sherpa.com, the industry's leading educational podcast on all things domains. You can find him on Twitter at Andrew Rosner, R-O-S-E-N-E-R. And one note before we dive in, Andrew and I got into the weeds on domain valuation. We really got into the technicalities, which is super interesting.
But that discussion, because it was deep in the weeds, was moved to the end of this interview for Flow. So be sure to stick around to hear Andrew's answer related to how do you actually determine an objectively defensible valuation for domain names? Fascinating topic, but it got quite detailed, so we moved it to the end of the conversation, so stick around. And with that said, please enjoy a very wide range of conversation with Andrew Rosner.
So I usually have pretty good idea of where I'm going to start these conversations. And I'm looking at this list and it's like a combination of memento meets forced gump meets globetrotting. And I'm going to let you choose. So should we start with
This will be very back and forth. We're gonna fast forward rewind so we can start at any point, really. Charlie Tuna or why you paid $25,000 to buy fuckyourself.com just to get an email address or pilgrims. Where should we start? Well, all right. Let's start with Charlie Tuna because it inspires all else. Perfect. Who the hell or what the hell is Charlie Tuna?
In college, I studied management information systems, which was basically a hybrid of business and computer science. I chose that because quite pragmatically, as I am, it was at that time in 1990.
mid 90s, the highest paying job out of college. And so I said, well, that's what I'm going to do. So I did that. And I started a software business in East Hampton, as a matter of fact. And I quickly realized that it was not what I want to do with my life. And so I then subsequently graduated a few months later.
after coming to that realization with a degree in something I didn't want to do, and I had no idea what I was going to do in my life. And I got a call from so-called Charlie Tuna, a very, very close friend, somebody I would call a mentor and an extraordinarily unique individual on this planet.
Peter murky, so I get a call from Peter murky, and Peter says, do you want to come selfish? How did he get your name or number? So Peter contacted University of Rhode Island, where I went to school, contacted the business school, and he said, I'm looking for an entrepreneurial go-getter to become my mini-me.
And Peter wanted to retire and he wanted to train somebody that had not come from the seafood industry. That's what we call foreshadowing, folks. He wanted to train somebody to basically take over the business in his own image. And I was the chosen one. So anyways, I basically told to go pound sand. And then at that point, he offered me $1,000 to come hang out with him for the day.
in Newport, Rhode Island, and I did, and it was kind of like, love it for a sight. I just, we hit it off. I walked into the office in a business suit with a tie-on and a briefcase, my resume in the briefcase, and, you know, the secretary let me into his office, and he had his feet up on the desk, and he was blowing out a bong hit, and he looked at me, and he said, if you ever come in my office in a suit again, it'll be the last time you ever come in my office. What was he wearing? He was wearing a, like, a Native American
ponto type of thing and he's got you know long hair of the ponytail and this. Unique beard that only Peter can carry, but he's a brilliant man he's a Stanford grad he's an old hippie and he just has a unique perspective on the world. I've never encountered anybody else that sees the world the way that he does.
And I think it was probably the most important event of my life, because I'm ambitious and I'm aggressive and I'm full of energy and ready to go tear the ass out of the world. But without any real direction, isn't always the weapon suited to the task. Absolutely not, absolutely not. But at that age, it's better than nothing. And Peter was very good at harnessing that and pointing it in certain directions, directions that were beneficial.
Yeah. So I went under Peter's wing and I spent eight years in the seafood business, the frozen seafood business. I traveled the world. I negotiated with, I couldn't even imagine the number of different countries and the types of people. I literally did business with some of the worst people on earth.
You know, the fish business is a cash business, basically worldwide. And so it lends itself to certain elements. It was just an amazing life experience. So walk me through what it looks like. Let's just say your first week or month on the job, like how is the compensation set up and what are you actually trying to do? So my first day on the job, I come into the office, obviously no longer wearing a business suit. And I sit down at my designated desk. Now there's only about, I don't know, at that time, four or five people. And so I sit down at my desk,
And I don't know, an hour or two later, Peter comes out of his office and he comes over to me. And I'm basically sitting there doing nothing. I've got some reading material that somebody's given me to look over. And he walks over to my desk and he points at a poster on the wall that says, exactitude. And he says, do you know what that means? And I said, no. And he said, have you ever read the book? At least shrugged. I said, no. Have you ever heard of it? I said, no. He says, do you know who I in Rand is? I said, no.
went into his office without saying a word, went into his office, got a copy of Atlas Shrugged, brought it back to me, and he said, go home now. And I was like, wait, he's like, go read this book, don't come back in until you're done. And so I literally, I went home and I literally took about five days to read the book. It's not a short book. No, it's not, it's a big book. And it's not easy reading either. At least the first like 200 pages, it's like a 200 page intro. And so I read the book, I came back in,
It was kind of like a fifth grade book review. And I don't know, I guess I passed that was it. And then, and then it was like, okay, look, come with me. And he took me down to the New Bedford, Massachusetts and drove me around to these different scholar processing facilities. And I met some absolutely crazy people, amazing, amazing people. These are just truly to this day. Like I was just actually back in Rhode Island in September, the end of September.
for a little memorial thing. And I met up with some of these guys that I hadn't seen in a long time and brought me right by the really just amazing people. You just don't, you know, I'm sure there's other industries like that, but seafood is a really special, truly salt to the earth business and such a dichotomy from.
the business I'm in today. In that boiler room, what did exactitude mean? Why was it on the wall? I think it means different things to different people. To Peter, what it meant was having the right information in order to arrive at the right answer. He did not like
knee jerk reactions. He didn't like knee jerk answers or in precision. So once you've read Alice shrug, which I'll admit, I've not read, but I know. Shame unto me. Once you've read that, you come back five days later. At that point,
Is it some form of arbitrage? Like what is the basically business model? Yeah, basically. So what's remarkable is Peter's business is still going today. I think now it's 40. Yeah, I think he started in 1985. So roughly 40 or 38 years. He doesn't own a factory. He doesn't process. He doesn't own boats. He's primarily scallops. There's other businesses, but it's let's say core businesses scallops and 100% of his competition owns at a minimum. They own the processing plant. Most of them own boats.
Most of them have joint ventures or partnerships with foreign processors, aquaculture, etc. Despite these seeming disadvantages, Peter has been nimble and
You know, he's kept his overhead low and through the good times in the bad, he's just kept that business running in a great time buying and then reselling, buying, putting in his packaging. In some cases, I don't know if we want to go into that today, but you know, what was called value add. We can skip, we can skip certain details. They would say they're value adding and repackaging and then reselling.
It's a pure arbitrage. So what was the annual turnover? And I'm going to hop to a specific example. So what was the annual revenues roughly when you started there?
They were doing about seven or eight million a year when I started and how did it grow quite quickly. We realized I was good at this game and I became the vice president of sales. And I think when we left, we were about 35 million. Okay. How do, which is a lot of scallops. Yeah. How do Hokkaido scallops fit into this picture?
Northern Ireland, Japan, for people who may not know. So basically, this is a pure sales game, right? So I literally have the equivalent of a phone book, but it's the who's who of the seafood industry. And I'm literally making about, I don't know, 150 calls every day. And it's just cold calling, cold calling, you're selling to distributors, to restaurants.
No, no restaurants, primarily distributors, other wholesalers, restaurant supply companies, cruise lines. So I say no restaurants, but a large restaurant chains, which is where we're going with the story. But a couple of years in, I come across Benihana and I call up the Fort Lauderdale headquarters of Benihana and you guys want to buy some scallops. And it's just pure luck that they happen to be in a transition period where they've been getting all of their seafood from one company.
And they decided that they could get better pricing and there was other advantages by put out of bid, put out of bid for each individual product. And so it was just great timing. And so I had the opportunity to put in a bid and by any stretch of the imagination, I shouldn't have had any chance of winning the contract. But as fate would have it, you know, I did my due diligence on the buyer and he was Nicaraguan by descent.
And he loves cigars and Peter happened to be a cigar connoisseur. And so he sent me to his guy who could basically source any cigar. I said, look, I'm looking for an amazing, amazing cigar that if it happened to be from Nicaragua, might even give me an extra edge, but something that's going to be really wow. And he said, I've got a cigar for you now. I couldn't even tell you what that cigar is. But it was a very expensive, very good cigar. I got a box of them.
And so I flew down to Fort Lauderdale and I took this guy out to dinner and I gave him this box of cigars. And the fact that I knew he was from Nicaragua, the fact that I happened to know this, I didn't actually know, but he thought I did this brand of cigars. I nailed it. And so we had an amazing dinner and we drank way too much. And ultimately I made this sales pitch about Hokkaido scallops. I said, look,
you guys are using american scallops okay and america scallops are great arguably if you're getting them pure form which. It's very difficult it's the best in the world however pure form meaning like an adult rated on adulterated you know i mean crab meat yeah type of scallop.
Yeah. Yeah. That's the least you're worries. It's the value-adding part, but it's not so. You're getting guinea pigs. Yeah. Okay. So the interesting part of this was basically American scallops are graded 0 to 10, 10 to 20, 20 to 30. And that's basically 0 to 10 per pound, 10 to 20 per pound, 20 to 30 per pound. But the Japanese, as they do, grade them much more consistently. And so it's 0 to 2, 2 to 4, 4 to 6, 6 to 8, 8 to 10.
And that tightness of grading makes an enormous difference if you are a restaurant and you're trying to calculate your plate cost. So you want your place to be consistent. You can't be that one plate has four scallops, one plate's got six.
And, you know, oh, well, I've got this one giant scallop. And so now my plate causes thrown off. So that inconsistency in scallops are one of, if not the most expensive per pound protein from the sea. And so it makes a big difference. And so I basically made this whole pitch about, look, you guys can have consistent plating, consistent
plate cost and you know there's a lot more to it but that message resonated and it closed the deal and i got the contract and it literally became our largest client and i supplied all of any hana worldwide all their scallops and i subsequently became basically the world leading expert on who kind of scallops.
Was it a known fact in the industry that Hokkaido scallops had these advantages? Nobody cared because they were taking the packaging that came from Japan and they were just repacking it into American standards, right? And so it was just another source, just like we got scallops from China, we got scallops from Chile, from Peru. It was just another origin, high quality, but the grading wasn't a selling point. That wasn't a known selling point. So what made you good?
I mean i have some we've spent a good amount of time together so i've some guesses but rather than guess what do you think made you good at this job. I'm not afraid to sell i think i have to start there is that i took it for granted that. Oh and me phone book i'm gonna start making cold calls i'm gonna get on the phone with people trying to sell something that they.
Never knew they knew. Never knew they knew. I think that was a big factor. And then, you know, I've got the gift to Gab. I'm rarely at a loss for words. I'm very good at adapting to people and meeting people where they are. Whereas I think a lot of people in sales are trying to bring somebody over to where they are. You got to meet the person where they are and understand what they need.
And then craft your message and craft today whatever it is you're selling, if possible, to meet them where they are for the need that they may not even know they have, but you've identified. So I think that adaptability, you know, Peter had two nicknames for me, the chameleon.
was one and crystal meth was the other. I have an extraordinary amount of energy and adaptability. So I guess I think a willingness to sell without fear and then that high energy to tie up just to lose end here and bring this boomerang back.
to the initial question for a minute. So is Bruce Wayne the Batman as Peter is to Charlie Tuna? 100%. They're one and the same. One and the same. All right. And Charlie Tuna, he was a squash player. Peter influenced me in ways way beyond business. Like his lifestyle, I had never seen somebody with that lifestyle. What was his lifestyle? Well, it was like,
Again, you know, he's an old hippie who had been, you know, he was playing the long game. He had this little business and he loved it and it made, you know, a couple million bucks a year over a year and, you know, good times. He made more and bad times, you know, maybe made a million. But it was, it was a great business and he'd just been chugging along, chugging along. He had no ambitions of scaling.
You know, I came in, I'm fresh out of college, and business school, and I'm like, well, we can do this, and we can, you know, automate this, and we can do it. And he's like, look, shop kid, just keep chugging, okay? And he would take off, he'd go down to Belize for a month, and he'd go, you know, eat a chalet on the edge of a cliff in the middle of nowhere in Gaspé, in way up Northern Canada. And he'd just go up and hang out at this chalet, and, you know, watch Wales break, you know, the surface. And he just, he didn't,
Aspire for the things. I guess at that time, you know, I, you know, you look up to these people that you think are successful and you think, wow. And you try to model the way that they live their life or the things that they buy or mark as trophies of their success. And Peter didn't have any of that. He optimized for what I would say is freedom. That's how I've sort of digested it into my own life and what I've modeled. He optimized for freedom.
Anyways, coming back to your original question, I'd go off on tangents because he's truly. Chris Smith. Yeah, so he got the Charlie Tuna moniker from his squash. He was a competitive squash player. And that was his nickname was Charlie Tuna. And he got me to squash. So what are the tenets of Charlie Tuna? I actually meant to bring it because these tenets are like mantras.
to me. But it's a few sayings that either he identified or people that he worked with or customers that he worked with for a long time, sort of identified as things that he would just say a lot. And they're just these short little phrases that get a certain point across. He had 10 of them. They were on the wall in the office. I've expanded it to about 15.
I still say the 10, 10, it's a trolley tuna because it just sounds better. But you know, it's like, I'm not Mother Teresa, I'm here for a profit because you get customers and they're like, well, you know, can you do this for me? I really did it. And I think, well, look, I'm here for business. If I was here to make friends, right, you know, we wouldn't be on the phone, we'd be meeting somewhere for a beer, but I'm not Mother Teresa. And I'm here to make a profit unabashedly or don't be backwards about going forwards or what does that mean?
Well, people do things in these roundabout ways, like just be direct. Just say what you want to say. Do what you it is where you want to do. Don't, you know, dance around. Don't beat around the bush. Just one, which I literally, I've still to this day, never understood, which was don't crowd the mourners. I don't know what that one meant. Yeah, don't crowd the mourners.
There's still some riddles on the song. Yeah, yeah, that one I never got a clear answer to. All right. I feel like we were having sushi at one point and you're like something something like in the whorehouse. Oh, yeah, one of the better ones. You can't run a whorehouse without any horse. I mean, all right, on its face, this makes sense. But what did that mean? In its original context, it's like if we don't have enough inventory,
We can't do business because it's an arbitrage deal. So if I don't have what the customers, we only have a limited pool of customers. Like we're not trying to be Walmart, right? So if I don't have what these people want, then I'm just losing business. And so if you want to run a scallop shop, you better have scallops.
If you want to run a domain broker, you better have the best domains in stock. You know, it makes sense, but you'd be shocked if you look around and you examine failures. How often that's the case that people are trying to run a whorehouse without any horrors because generally they're trying to avoid risk, right? They're trying to be risk. I imagine some people listening would say, well, hold on a second, like, I keep on a gum, Charlie. I guess that's fine. But Peter ran a really
Tight shop. Tight shop. He seemed to carry much lower overhead and fixed costs because he wasn't verbally integrated like these competitors, which all makes sense. So they might then extend that to say, well, if you're running an arbitrage business, could you not identify the need and then source the inventory? Or are you just too slow? Like you missed the window. Miss the window.
miss the window. You don't have it. It's a commodity, right? So you don't have it. The next call is your competition. Very little differentiation. It's a commoditized product. So you must have to get pretty, I would imagine, to make that work. And maybe I'm imagining incorrectly, but pretty sophisticated with forecasting and
prediction and so on because like scallops last I checked, don't last forever. So if you're holding inventory, it's not like you can sell the next percent. So I don't know how deep down this rabbit hole you want to go. But that was one of our superpowers was another way that Peter has really influenced me was Peter lived all over the world. Okay. He dodged the Vietnam draft and went to Namibia and then
He lived, he's lived all over the world, and he's traveled all over the world, literally all over everywhere. And he had these relationships that were just the most absurd relationships. Everybody had crazy nicknames. And in Chile, in Peru, in, you know, we had- Hello, the catch. We had Mr. Lucky in China, and we had- Mikey the Iron Ranch. Crazy, really, like, and he just knew these people.
he would call them up and he'd just say, you know, what's it looking like in Peru? What's it looking like in China this year? What's it looking like in Japan? What's it looking like? And every morning, that was literally the first thing I did in every series, like catch type of catch or catch may not be the right term. But yeah, I mean, a lot of these guys, they came to appreciate Peter and his personality. He's truly a character and the method.
But you know, I would make these calls. I had a list of 20 people that I would call every single day. And I literally wrote out a report of what that person said every single day. And I presented it to Peter every day. And this isn't a fast moving business. And so generally speaking, whatever they told me yesterday is the same thing they're telling me today. And so it was, it was redundant. But what it did is it honed a whole bunch of different skills.
And it caused me to build a relationship with these people in a way that Peter had built over an extraordinary long period of time. And so it got them to trust me, got them to know who I was, and it got them to share information with me that they weren't sharing with other people. And most other companies had a more local centric focus on supply.
So they knew what the catch was like in the North Atlantic. But they didn't know what the imported supply was going to be from China or from Peru or from Chile, where there's these massive aquaculture operations that were just happened to be at that time really scaling up to match or now far surpass the domestic supply. And that allowed us to understand where price was going to go. When you say you got to have the horse to run the whorehouse,
You don't have to have all of them. You just need to know that the guy coming in the door wants a red-headed, whatever, right? And so I need to know that the thing that's gonna be short in the market is gonna be 30, 40 size scallops, 20, 30 size scallops. I need to know what's gonna be short because the stuff that's gonna be abundant, I can get that readily. I will know the price readily. I won't get caught with my pants down on the price. And so I can do what you were saying before, which is like what we call the back-to-back.
But by having the stuff that's in short supply, I'm going to get the business because I'm going to have the thing they need, even if maybe I'm going to be a nickel or a dime higher on the stuff that, you know, the other stuff that's abundant. I'm going to be the guy that's got the right price on the stuff they need that they can't get from everywhere.
And so that was really our superpower was knowing where to fill the holes, which gaps were going to give us that advantage that would allow us to compete on the stuff we otherwise wouldn't have been able to compete with.
We're going to move from Tuna as in the namesake of Batman slash Charlie Tuna. We're going to move from scallops to Hamoni Barrico. It's a good segue. We're going to move from food to food. Okay. Where does this fit into your life story? I did a semester abroad in Australia where I met my now wife who's German.
And while we were dating, playing international love affair, she took me to Mallorca, where I had Hamon Iberico. Patanega, there's many different names for it. The Portuguese would tell you that the pigs are raised in Portugal and then cured in Spain. But traditionally speaking, it's people nodding in the room.
Traditionally speaking, it's a Spanish ham from the black-footed pig. And at that time, in the very early 2000s, it was illegal to import it into the United States. And when I tasted this with my wife, my now-wife, I was blown away. It was the best meat I'd ever had in my life. I couldn't believe it. And I was like, why don't we have this in the United States?
And I was in the seafood import business. So I thought, I'm going to import this to the United States. Backtrack to my college days, that was literally the mid 90s. It's the emergence of the consumer internet. I took a class learning about the internet. I thought, wow, domain names, amazing. I started registering them because I'm hyperactive. And every time I had an idea, I'd get a domain for it, not thinking that these would be valuable. But anyways, coming back,
I thought I'm going to get some domains for this Hamona Barrico thing and I'm going to set up a website and I'm going to start importing this stuff. So I got back to the US and that was my attention. I discovered that it was actually illegal. The FDA did not allow you to import this Hamona Barrico because it's cured for 18 months. You know, it's a raw meat that's cured for 18 months in salt and like French cheese, the FDA didn't designate it as fit for human consumption. So, you know, that was sort of that. And I put it in the closet and forgot about it.
And then a couple of years later, I'm driving to my office, and I hear on NPR radio that George Bush is about to get, you know, the first Tomoni Barrico ever legally important to the United States and couldn't believe it. And I got to my office and I found out who the importer was and I called him up and, you know, started talking shop and I told him, you know, I wanted to buy a ham from him. And he was like, look, I'm sold out for a year. I basically have a monopoly or he had a monopoly.
You know, and these were like, I don't know, seven, eight, $10,000 legs of ham at that time. And it's literally, you know, it's a whole leg buying a thoroughbred. Yeah. And, you know, so he was like, you have no chance. Forget it. Get in line.
And, you know, we're talking shop and it came up that I had these domains and it was like his proverbial jaw dropped and he immediately was like, how much do you want for those domains? And it was the first time, like I said, I bought a lot of domains at that point already, but never thinking, oh, these are valuable assets and I'm going to sell in the future. It was always like, oh, this is another lame-brained idea that I'm going to try and build a business around that I never got around to.
And I didn't even know what to answer. And so I said, well, I want one of your hands. And he goes, no problem, done. And I was like, oh, wait, that's too easy. And so I was like, and $5,000. And he's like done. And I was like, well, you know, the hands got to come from that first container, you know, George Bush's container. And he's like, done. And I was like, oh, wow.
Okay. And, you know, it kind of was like, all right, it's yours. And so, you know, I had a few of these domains and I transferred the domains to him on the spot. And at that time, I had no idea how to do a domain transaction. And so I just took the leap of faith, transferred them the domains. A couple of weeks later, I got a coffin in the mail. And, you know, the rest is history. That moment then gave birth to my whole domain business. I realized it just, you know, a little esoteric
corner of the world, if this guy wanted his domains that bad, every business in the world is going to want or need their respective domain names. At this point, I'm still in the seafood business and I
was making quite a lot of money for somebody in their mid 20s. And I just started backing up the truck and buying as many domains as I possibly could. Now, where or when this test Diaz into the picture test Diaz worked for GoDaddy.
And GoDaddy at this time, then early 2000s, they launched what they called the executive department or something at that time. They looked at their accounts and they were like, wow, some of these people have thousands of domain names. Let's reach out to them and figure out what they're doing with these domains. And so they set up this little department with a few people, and their job was to reach out to these people that had more than 1,000 domains and figure out what they were doing with them.
Most of these people knew what they were doing with them. They had a purpose. I did not. So any test called me and I was actually in my car, I was driving up to my good friend JB's house in upstate New York, quiet police farm, and I had a lot of time. And so she called me and she said, you know, what are you doing with all these domains? And I was like, I have no idea. I never time of an idea. I buy them.
And she said, well, you know, there's like a domain industry and there's people trading these things and you can monetize them. And I had no idea, you know, tell me more. And so literally I spent like three or four hours on the phone with her getting a download on that there's a domain industry and, you know, an aftermarket and there's people on forums talking about these things. And
There's different ways to, you know, park them and monetize them and Google will pay you for the clicks. And it was, this was all new to me, but it was fascinating. And so I then spent weeks as I do deep diving into this new world of domain names and I got super fascinated. At this point, I'm married and my wife thinks I'm crazy. In fact, everybody thinks I'm crazy because I've now spent a considerable amount of money buying domain names by that point.
And basically, when I got married, my wife said, look, I'll live in the United States for four years, and then the shot clock is up, and then we're moving somewhere else. And the shot clock ran up, and it sort of ran up. At the same time that I was doing this deep dive into this domain world,
And what I realized was there was nobody playing matchmaker between the people that had these domains, fascinating characters, like literally you would be hard pressed to find an industry that has such a motley crew of extremely successful and by a variety of standards, people, but from just wildly different backgrounds, wildly different interests that have stumbled into this industry in completely different ways.
I decided to basically build a domain brokerage business to play matchmaker and there was people trading amongst themselves, kind of playing hot potato in the domain industry. But there was nobody taking these domain names and selling them to the end users that ultimately could benefit most from them and more importantly playing educator between this nascent asset class and.
the broader business environment that I think recognized, like, oh, this is an extension of our brand, but didn't understand why these things might cost so much and why they're so valuable and, you know, the various benefits of owning them. And therein was born media options. And my wife and I founded it together. And I think it was maybe a year or two later that Tess became my account rep at GoDaddy, just, you know, going full circle here. And then ultimately left GoDaddy to come work for me.
And I went from a lone ranger to plus one. And shortly thereafter, you know, we moved to Panama. We left Rhode Island and moved to Panama.
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If we take a 30,000 foot view for a second, for folks who are unfamiliar with the domain slash domain world, and I would put myself in that category. Maybe I know the edges of the puzzle, but I really don't know what the entire thing looks like at all. So there's an aftermarket, there are auctions, experies,
dnjournal.com, dnforum.com, domain name wire.com, expired auctions. Can you just give us an overview of what that world looks like? What are the main pieces, the main positions, so to speak?
Like any market, it has a structure. There's a clear texture and structure to the market. You have, let's say at the lowest level, you've got guys that are just really appreciate domain names and they're investing in domain names. Maybe they're hoping to strike it rich, like a lottery ticket. Maybe they're like me and they just have eccentric ideas and registered domains around them. Maybe they drank too much and thought they had a clever idea that they regret in the morning.
But there's just people that are collecting domain names. And then you've got people that are really taking it seriously, investing into domain names, and they've got varying methodologies. I've got one of my very good friends. Yawnee is super methodical. He's a robot. He's got algorithms. There's very little emotion or anything that goes into his formula, whereas I'm kind of the opposite. I'm basically 100% on instinct. And then I back it up with data.
but I primarily am operating from instinct. But either way, we utilize primarily the same tools as like the SEO industry to sort of gauge what the total addressable market of these domains is. And so there's a whole bunch of different tool providers in the domain industry to sort of uncover who owns a domain, trying to evaluate a domain based on a bunch of data points.
There's a bunch of different tool providers. Then you've got forums where these people meet. Less today, it's less relevant today. I would say Twitter is kind of the X.
Another segue we can go down, but X is really where the material domain world is meeting these days. And, you know, there's just a lot of these investors coming at this from a lot of different angles. And then you've got, you know, some of the names that you mentioned, domain name, wire, D and journal. I would say those are the two most prominent. They are covering the news. These are our true journalists for the domain name industry.
And they're talking about policy changes, domain names are governed by ICANN, which is the multi-stakeholder, non-governmental organization that basically governs domain names, and remarkably important organization, by the way, that
very few people know even exist, and more people should know that they exist. But there's all these different layers, right? And then you've got, as the industry evolved through the late 90s and then the early 2000s, these good domain names get what we call type in traffic. It's just inherent traffic. People just inherently go to these domain names, prime.com.
Yeah, prime.com. People want to go to prime at Amazon. They just typed in prime.com. And we helped Amazon to get prime.com for that very reason, because tens of thousands of people were going to prime.com every day and not finding Amazon. And so if you own these domains, though, you can park them with Google or Yahoo on their parking feeds. And they display keyword advertising. And then when people click them, you earn a couple cents, sometimes more.
And at scale that can be you know considerable revenue and that used to be the primary business model in the early two thousands was capture that traffic.
Hope it leads to click-throughs on your advertiser and then get paid by Google at 100%. Just out of curiosity, because I know I'm not the only person who knows what it is now. I'm not giving a real example, but I'm typing something like Google really quickly and I type an extra Google 3Os and I land on that page. How should you think the owners of some of these misspelling pull-in?
I'm going to pause for a second because it's a really important point that I want to make. I would say like, if your audience got one point from me today, I really want it to be this. There is a very clear distinction between a domain investor and a domain squatter. The guy that owns Google with three O's is a squatter. He is the person. He, she, whatever is the person that gives
the domain industry, a bad rap in the late 90s in the early 2000s. That is worn off, you know, it still resonates, but it's mostly worn off at this point. But in the early days of my business, that was the biggest hurdle was like, you're just that dirty domain squatter, right? It was like,
The fact that somebody was an investor in domain names was a negative connotation. And funny enough, some of the biggest domain investors are famous VCs that are funding the companies that are accusing domain investors of being squatters. But anyways, really, there are VCs who own just, oh yeah, spreadsheets full of domains.
More targeted, super high quality, you know, maybe tens of domains, but really high quality. Are they holding them for portfolio companies or are they looking to, you know, I don't know. I don't know. Can I play stand in for the listeners for a second? Sure. All right. So this is differentiation, I think, is important.
underscores. So, squatter versus investors. Yeah. Do investors still buy URLs that represent trademarks owned by other people? And if so, how is that reconciled? There's always going to be bad actors, but it is a very, very, very small fraction of what it used to be. We've got cyber squatting laws now. It's quite punitive, $100,000. If you get student federal court, it's $100,000 per name penalty for infringing on somebody's trademark cyber squatting.
There are also much cheaper, faster, and easier mechanisms for recovering domain names than in Fringe on your trademark called the UDRP universal domain resolution protocol. Basically, there's three elements. And if you could prove those three elements, the domain is going to immediately get transferred to you. Okay. And it's going to only going to cost you about.
let's say $2,500, maybe three grand if you go for a three person panel for this arbitration. And they're going to make a decision. The owner gets to respond if they choose to. And in most of these cases where it's a clear trademark infringement, they don't even respond. And then that's it. You're going to get to the main name. And you don't need to know the identity of the... Nope, holder. Nope, for that. Nope, you don't.
And so there's very strong mechanisms both preventing and let's say clearing the market. There's very little upside to doing this anymore. And so like I said, there's still bad actors, but it's a very small problem compared to what it used to be.
When did you put up your shingle and start the company? 2008. Okay. I'm no historian, but 2008 doesn't sound super early in the domain of the game, which makes it more interesting to me, because it's not like day one of Google AdWords where you're shooting fish in a barrel, right? There was a point in time where I was like, oh yeah, we can just look at the dictionary and go buy a bunch of dictionaries. Totally. But at this point,
It would seem like you're buying or matching or both. Maybe you could explain the business model then what it looked like, which is incredibly interesting because it raises the question of how to value or how to determine a reasonable price, acceptable purchase price.
I wouldn't know how to begin doing that for something like, nor would almost anybody else like x.com, right? I don't know who would use it for what? I know it's single letter. Okay. But can you walk us through what the business model was at the time? You're coming in clearly not too late, but certain
Low hanging fruit most of the low hanging fruit have been a lot of them removed all right and so then how do you determine a fair price. I'm kind of taking a wild guess here but it's you know just for emphasis it's literally probably ninety five ninety eight percent of our business is domain names that were registered prior to two thousand. Okay so in two thousand eight when i.
As I said, hung up my shingle and started the business, I am super late to the party. Now, I have started accumulating some domains, but most of them weren't really great at that point. But what I understood that it was going to be a very capital intensive business.
And I had already spent a lot of capital. And if I want to continue this hobby, I needed to generate cash flow to support it. So that was one of the premises of starting media options. So then that premise worked. We started successfully selling other people's domain names using our commissions to then fund the acquisition of better domain names. So people would come to you and say, I have
Fill in the blank oh yeah i mean you're talking dot com and i would like to sell it but i'm not sure how to do a line out the door right so there's a handful of domain investors that understand what they've got and they have no real.
eagerness or intention to sell, except when somebody makes them, but everybody else is literally they buy the main and they expect it's going to sell the next day, right? And so anybody that can help them achieve that unrealistic objective, they are banging on the door. So I get so many emails every day of people that want me to sell their domains. So endless supply of inventory to sell.
So I start banging on doors and basically playing fake it till I make it because nobody had really done this before. How did people find you at that point? Most of the people that own the domains I'm selling at that point, that's no longer the case, but at that point, most of the domains that I'm selling are owned by domain investors, right? And so I'm meeting these people on the forums. There's the end journal, which does this weekly sales report. And so today I'm like,
the most discreet person you're ever going to meet. But at that time, trying to build a business, every time I make a sale, I would announce that sale. That would get published on the forums. Yeah. It'd get published in D&D Journal. That was sort of a source of pride. It was like, oh, look, my sale got published in D&D Journal this week. And people would see that you sold a domain for a good price and then
double down on, you know. So that was how the people that owned the domains were finding me. And I'm finding the people that I was trying to sell them to, okay? Very rarely are they coming and finding me. It just did happen, right? Lightning strikes. Do you still remember any of your initial sales where you're like, holy shit, I think this could be a thing? The sale where I thought, wow, okay, I'm really, I think I'm gonna be able to make this into a business was pizza.net.
Okay, okay. Which is a great example because it seems like there are a lot of people you could potentially sell it to. So walk us through pizza.net then. Pizza.net was a unique case. Pizza.net was a very famous domain because it was highlighted quite prominently in the movie The Next was Sandra Bullock in 1994. Really? Yeah.
So, in this is a 1994 movie, okay, and Sandra Bullock, first time anybody has ever seen anybody order a pizza online on the internet. Sandra Bullock goes to pizza.net.
and orders a pizza online. Pizza.net, it's another rabbit hole. Pizza.net actually has prior art on a whole bunch of patents. Google has the patent on, here's your IP, we're going to provide you
You search for pizza, we're going to provide you the pizza restaurants that are within a certain distance around your IP address, okay? They have a patent on that. Pizza.net was doing that prior to Google, filing that patent. And so pizza.net technically, so the company that owned pizza.net was doing that type of, sort of proximity. Yes.
Yes, the company was gone, but the owner of the domain, which he's also a fascinating, that's another fascinating story, but I don't recall how he found me. He was the guy that literally strung the internet cable up the entire East Coast of the United States. So he literally put in the actual hardware
that created the first internet network on the east coast of the United States. Adam, I can't remember his last name. Adam something put in the show notes. And we'll also put the rest of the tenets of Charlie Toon in the show notes for people who are wondering where those might be found. At the time in the early 90s, when he bought this domain, I want to say it was registered in 92. Mind you, most people didn't even know the internet existed till about 94, 95.
regular home adoption didn't really happen till 96, 97, but at that time in 92, 94.net was actually the preferred. Most people thought.net because most of the people using the internet were network providers. These were ISPs. They were, you know, it was a read only.
or write only. It was mostly tech not in the way that we think about it today, but like really hardware tech companies that were utilizing the Internet at that time other than just putting up a splash page like a business card and they were using.net. And so, you know, he had a lot of very, very good.net domain names at a time when he could have registered any of them in.com. He actually is the guy that
He originally registered, you know, you brought up x.com. There's three one-letter.com domains in existence. Okay, that's it. Three. It's Z, Q, and X. But Adam, I heard there were only three. So I'll tell you the story. So Adam actually registered all other 23. So numbers aren't allowed. Single numbers aren't just not allowed for security conflicts prevented by ICANN from being registered. So he went and registered all the other one-letter.com domain names.
But because he wasn't using them, I can then decided, oh, this is a bad idea. Nobody should be able to have these one letters. And so they pulled back all but the three, which they grandfathered in because Nissan was using Z.com for their 300 Z car, which is quite popular at the time. I think it was Quest Communications was using Q and Elon, as it were, was using X at the time. It was actually originally owned by a lawyer.
Elon bought it from him prior to merging with Peter Thiel for PayPal. So those three got grandfathered in and the rest got pulled back. Basically, I guess I have read quite a bit about it. I think the way I came was thinking about it was like, you know, maybe there was an element of security. You know, they're kind of a socialist organization. And so they probably thought it was unfair for any one company to dominate a letter of the alphabet. But for a variety of reasons, they clawed them all down for three. Yeah.
Pizza.net. So long story short, I sold pizza.net. I think it was for like $120,000 at the time, which used to be a lot of money. And I earned probably a $20,000 commission on that, probably the owner made $100,000 net more or less.
And it was a lot of money for me. I had this mantra at that time, I had just left a job where I was making about 400, three, 400 grand a year consistently. And I was 26 years old or 25 years old, whatever it was. And I would make a lot of money, like way more than any of my peers. And I literally jumpship.
moved to Panama, started this brokerage business, and I had a limited amount of savings that I'd spent most of it on domain names. And I had a limited amount of savings, and it was basically just enough for us to last one year. I had this mantra of every single day, five days a week, every day, I need to make $250 profit. If I don't make $250, then I am already falling behind the eight ball. But if I can make $250 every day minimum, then my business will survive.
How did you arrive at that number? I calculated what my annual expenses were going to be in totality and divided by the number of business days. This is another thing. It came from Peter. It was like, look, keep your expenses low. All my competitors, they were doing different things, but they were all trying to be very technical about it and build scalable businesses.
lots of people and lots of technology and huge overhead. And I had, at that time, I basically know over it. And so I was chugging along and doing whatever it took. I would give away a domain name just to make $250. That didn't matter. Even if I knew I was doing something that was going to be harmful to me,
Literally, I was not going to end my day until I made $250. And if I didn't make it, which was very rare, the next day, I had to make not double but triple. So it was like just punishment. It was like, okay. So I really stuck to that. And I think that that was a very powerful discipline for me early in that first year in brief, because I know a lot of folks listening and wonder why Panama.
We originally planned to move back to Europe and, you know, the sky was falling. And so we thought we really hated being in the US where it was really just being inundated with bad news all the time. And we kind of just thought, okay, well, it's going to just kind of be more of the same in Europe. Germany would have been the obvious next step.
We kind of said like, OK, we really want to escape that environment, particularly because we're going to launch a new business. I need some positivity. Like what I don't need is like constant negative vibes around me all the time. The other thing was this was we left in November. And so it was like a bitter New England cold winter, horrible cold. And I remember my wife got stuck to the manual car. She was driving up a hill in Providence and she got stuck.
in the snow and can imagine the German curses. Yeah. And so anyways, it was like, look, we're doing this business that we can do from anywhere. And so let's go somewhere warm. And I was like, yeah, let's go somewhere warm. And so we kind of explored all these different places. You know, we had visited a lot of places in the Caribbean and we'd gone to Central America and we'd, you know, I had been to Panama actually a couple of years earlier because of a friend of mine from college was Panamanian.
And invited me down. And so Panama just checked a lot of boxes. It was on the US dollar. Most of my business was going to be in US dollars. So that eliminated sort of the currency friction of volatility. Didn't even think of that. Yep. That was big. That was a big reason. It was very safe. At that time, Panama was the fastest growing economy in the world from a GDP perspective. I think it was 13 and a half percent GDP growth in 2008 or 2009.
Whereas China was number two with like 11%, right? So huge GDP growth. Why was there so much GDP growth? Is that like banking sector or no? Well, yeah. So the banking sector was growing rapidly. The Panama Canal was expanding. And, you know, we were basically really, let's say for that first decade of the 2000s, that was kind of peak globalism, right? It was like, wow, everybody's doing trade with everybody.
You know, that got sort of short stopped with, you know, the financial crisis, but things were booming. So anyway, Panama ticked all the boxes. That was really why we landed on Panama. So you're in Panama, pizza.net. Holy shit, this is going to cover a lot of $250 days. Totally. Right. This could be a business.
It was super important that I was hyper-focused on earning $250 a day. You're gonna have a hard time really building a big business if your focus is on making $250 a day. But it was critical for that first year to have that small goal and be achieving it regularly. But then when I got my first bigger win, it gave me the ability to take a deep breath and then say, okay, I think this business is going to work.
And I can start thinking bigger and, you know, I lost the discipline of like the $250 a day, but I started hunting bigger fish with the inherent confidence that came with achieving this discipline of, you know, hitting these small targets. So hunting bigger fish, this then brings us back to the question of valuations and acceptable cost. How do you think about this?
Andrew and I got into the weeds on domain valuation. We really got into the technicalities, which is super interesting. So be sure to stick around to hear Andrew's answer related to how do you actually determine an objectively defensible valuation for domain names? Fascinating topic, but it got quite detailed, so we moved it to the end of the conversation, so stick around.
what I wanted to ask about is something that people might find surprising. And this is a note that I have in front of me. I was surprised to see this. Startups in particular should not buy their domain name. They should lease the best possible.com domain name for their business with the option or path to buy later. Can you elaborate on this? Yeah. Yeah. Because this is a big decision slash important decision slash terrifying
Risk for a lot of startups. So I'm glad you said what you just said or they wait and then they get that extorted is a strong word, but I mean they really get bent over the barrel because the story is not actually the worst case scenario. Okay. Worst case scenario is that they no longer have a path to ownership.
for their exact brand match.com. That's actually the worst case scenario. That's a much worse scenario than we have to pay some exorbitant fee to get our domain name. And I'll explain why. So about 2015, 2014, 2015, we started seeing really like a parabolic rise in the value of domain names. I don't even know really what to attribute it to, but there was a sudden sort of inflection point where
more and more investors investors I mean really primarily VC's as well as startup founders and I think the startup founders part I understand that area around 2012 2015.
was sort of a lot of the guys that had a win or, let's say, might have had a win but then didn't sell fast enough and the .com boom happened. But a lot of those early .com successes were coming back for their second shot in that sort of time period. Yeah, it's true. I can for sure confirm that because I was in Silicon Valley at the time and a lot of guys who
had their first wins like 2007, eight, nine, or maybe that's when they started a company and they had just taken some secondary off the table. So maybe they hadn't had an IPO, but they were flush with cash and they were looking to build more things. I saw this a lot.
Like anybody who's successful they learn from previous experience and a lot of them understood that okay i launched on this silly name and i might have gotten lucky and been successful because the market wasn't crowded but now the markets crowded and now there's a million people want to compete with me. And there's a lot more resources to fund those people want to compete with me and so i need a strategic advantage that.
My competitors can't. That gives me a moat. And a domain name is one of those advantages. And so a lot of repeat founders, this is a trend that I see. First time founder pushes back a lot on buying their exact brand match.com. They see it as a risk, as you said. Most people perceive it as a risk. What I would tell you is that it's actually a de-risking.
Well, I want to make sure we talk about leasing. This is why we're going to circle back to. Yeah. Yeah. Now, this is actually directly leading into the. Let me just to strongman this a little bit. If somebody is in a weak cash position, I mean, it could be risky to.
overpay in the early stages. Sure. But this is where it's going to dovetail into the leasing thing. Because I think regardless of the cash position that you're in, not regardless completely, but within a realm, it's a better strategy, the leasing, rather than an upfront, just all out purchase. And so around that time, 2014, 2015, domain names really started to rise. And I was sort of telling you what I attribute that to. But as the values started going up,
It became harder and harder to sell these things. There was less people that could afford to buy them. And there was some companies offering financing, but very high rates and not super attractive to most businesses. And so I was trying to come up with ways to increase the pool of potential buyers.
and increase my ability to close sales. And so I thought, well, we're all, I say we're all, because I also own a lot of domain names. We're sitting on these domain names that we all know are really amazing assets. They keep going up in value, but they're so underutilized sitting in our portfolios. And really the whole parking thing, which used to be big business, like we used to make real money from Google with parking, but around 2008, 2009, that started, you know, it's been a downhill slope ever since.
We used to get the lion's share of the revenue and now we get peanuts. So as the values went up, sales got harder. And I came up with this idea of like, well, why don't I just lease you the domain? I'll give you a fixed price option. So you have an exclusive option to buy this domain. Nobody else can buy it. Even if somebody shows up and says, you know, I'll give you $10 million to that domain that you, you know, lease to this guy for $1,000 a month.
Nothing I can do about it. We use escrow.com is one of our biggest partners. It's a third-party escrow service, which I would encourage anybody doing a domain transaction. That's, in my opinion, the only, maybe you can use a lawyer, but other than that, it's the only safe way to conduct a domain transaction. It used to be owned by Fidelity, and then it was sold to a private guy, and then that guy sold it to Freelancer, which is a public company from Australia, Freelancer.com.
sole owner of the company now. Anyways, we're going to put the domain in escrow.com. That way, no matter what somebody else offers me, no matter if I change my mind, there's nothing I can do unless you as the person leasing the domain breaches the contract that we enter into. There's nothing I can do. You keep making your monthly payments.
Right off from the sunset, you might not even ever have to talk to me again if you don't want to.
I mean, I am their number one client. I've done hundreds and hundreds of millions of dollars in sales and knock on wood. I've never one time ever had a transaction go to arbitration. Right. I'm not saying, but yeah, if it were, if it were, it goes to a third party forum, arbitration forum, and they will basically organize that because they're the ones holding the domain. So they've got an interest in sorting this out as quickly and amicably as possible.
And so they hold the domain, there's usually a payment upfront, which basically buys you an option, which in the world of finance, like any other option, you have an option to purchase this domain at a fixed price for a fixed period of time. I generally default to five years. I think that's a great runway. Most businesses at a period of five years,
are either going to make it or break it. It's going to be binary. At the five-year point, they know they've got a business and they're raising either more funds or they're profitable or they've achieved some level of scale, but they either have a business or they don't. And so at that five-year point, they have, and they can execute at any time during the lease. They can execute after the first monthly payment if they want to. But within that five-year period, they have a fixed price option to buy the domain.
Exclusive to them and then they have a monthly lease and so generally rough back the napkin math the way these things usually fall is like Somewhere around five percent could be ten percent the bigger the value Usually the numbers come down the lower their percentage. Yeah, so it's over that five-year period
You mean? Yep. So the purchase option, and it's important that that start up have some skin in the game. Oh, I see. That's the initial. Yeah. Option cost. Yep. Not the total cost over the five year. No, no, it's going to be the initial option. Get some skin in the game, buy yourself an option, and then you've got a lease component. And the lease component is going to be usually be like a half a point, right? So if it does that option upfront payment act as a
in advance in the case that you purchase. In most cases, yes. So generally speaking, we apply that option fee. Let's say that you approach me, you want to buy a domain. That domain is $100,000. We agreed at one of these lease deals. Maybe you're going to put $5,000 or $10,000 down upfront.
And then you're going to have a 90 or $95,000 fixed price option to buy. And then you're going to have a lease component. And the lease components are true lease. The payments don't go towards the purchase price, but it's a half a point. So if it's a $100,000 domain, you might be paying $500 or maybe $1,000 a month. So it's a half a point or a point a month, which is going to get the owner of the domain, a very reasonable conservative rate of return of
Call it five to 12% rate of return, which is going to account for inflation and account for the risk. And you're going to have the opportunity for less than a cost to keep your floor clean to operate on your exact brand match.com from day one. And so that's the first element of de-risking is that number one, you're never going to have to rebrand, which is a very because of SEO, because of technical challenges, because of
word of mouth and a whole bunch of different things, a rebrand while you're at stride is very difficult to pull off. And it leads to all sorts of messiness. Generally speaking, it's going to cost you somewhere between depending on the complexity of your organization, between 10 and $40,000 per employee to do a domain name rebrand to move from one domain to another one, particularly gets higher and higher and higher the later stage you are in your organization and the more complexity you have.
you are leasing the domain, you look like you're a serious business right from the get-go, you're not. Try this or get that. So question for you on the sell side, because now I'm super interested in this, because now I'm thinking, huh, are there people who just have a stable of domains and they treat it almost like, and this isn't a perfect analogy, but like a fixed income portfolio where they're like, I'm not in the domain selling business, I'm actually in the domain leasing business.
But to run the math on that model, if you were in that position, you would want to know what percentage, just so you can forecast properly, you'd want to know roughly what percentage you would expect to convert to buyers at the five-year point. Do you care though, really? I'm curious what it is. Okay, so this is literally one of my favorite topics.
This was part of the whole revelation of creating this was I was sitting back and I was thinking to myself like, all right, now I've got about 5,000 really good domain names. Let's just take the top 500. These would all be domain names that at an absolute minimum, you're talking about $100,000 and that would be cheap. So $100,000 and up, some of these are eight figures. Some of these are seven figures. Some of these are mid six figures, but a lot, right? But $100,000 to many millions of dollars in value.
the price I would expect to sell them for. If I just took the top 500 domain names and I, let's just say I'm giving them away. I'm going to give away all of them for 500 bucks a month.
It's $250,000 a month in totally passive income. And when I say passive income, like, you'd be hard pressed to find more passive income, right? Because it's not like a real estate portfolio where like, you got a once in a while, you got a risk. You got to fucking deal with it. Yeah, you got to do a broken pipes and electricians. And you got to, you know, you got local and state.
real estate taxes and you got that, that, that, that, that, right? What you get gross is very different than what you get net and not to mention the time investment. So I laugh when I hear people in the real estate business talking about passive income, but it truly is passive income. It's literally set it and forget it. I literally hand the domain off to escrow.com. The servers get pointed to the person leasing it and I get a notification once a month that the payment was received. End of story. That's it.
That's a pretty good gig. When I did that math and I was like, wow, I like those numbers. It got me pretty excited and I started to pursue this. And I talked to GoDaddy and I talked to some other players in the industry saying, why don't we promote this as the way that companies should sell domains or acquire a domain? And from there, the concept evolved in my head to the point where it's a no-brainer. Even if you have the money, why lay out the cash if you can
Lisa, try before you buy it. Even if you know you want to buy it and you have the money to buy it, you probably have a better use case for the cash flow. It literally is going to cost you, in most cases, less than you pay to keep your floor clean in your office to have this domain name. The lowest paid person in your company costs more than your company's branded domain name per month. So it's a no-brainer, in my opinion, for almost everybody.
when you go to raise funds and you go to your VC being, I am, you know, Vida.com. I'm an investor in a company called Vida sold in the Vida.com domain name, which is a good segue into another element of this that you sort of reference. But it's a lot easier to raise capital going and saying we are Vida and we have Vida.com.
rather than we're Trivita or we're vita.io or we're vita.xyz. You're not a serious company. It's like you're on training wheels. And so at some point, and most of the smart VCs know this,
At some point, you're going to have to upgrade because there's a ceiling. You'd be hard pressed. There are a few exceptions, but I think you'd be hard pressed to tell me a company valued over a billion dollars that isn't on a dot com. You'd be pretty hard pressed. And I think there's only one fortune 1000 company that is not on a dot com. So at some point for a variety of reasons,
you're going to hit a ceiling if you do not have your exact brand match.com. Maybe it's because you want to go public and your investment bank, which was the case with Facebook when they wanted to go public, the investment bank, whoever was, the auditors, whoever was, came in and said, look, you guys need to own all your IP before we're going to take you public. And so last minute, they had to go out and buy FB.com from the American Farm Bureau and they paid $8.5 million for it.
because literally a banker told them they can't go public until they wrap up this IP. Or maybe you're going to raise your next round of funding and your VC says, look, if you don't have your .com at this stage,
It's a huge risk. We're looking for 100x here, right? We want you to be a $10 billion company or $100 billion company. And you can't do that without your.com. And so if you don't get it at this stage, then we don't know what it's going to cost later or you might not be able to get it later. And they realize that that's an inherent risk, right? So there's a bunch of advantages.
Let's say lubricating the fundraising process, de-risking that process in the mind of the investors, as well as the downside risk of not doing so and looking like you're not serious or you have a short-term vision or you're not committed to your brand. Vida.
You mentioned you're an investor and he said that relates to another element of this. What is that other element? I mentioned that just because Stephanie Telenius, who was early, played at Yahoo at PayPal, and I think 2012, Woman of the Year in Technology, phenomenal founder, she approached me to buy vita.com. She didn't want to pay... V-I-D-A. V-I-D-A. Okay, V-I-D-A. Yeah, the Spanish word for life. Yep, got it.
Okay, she was building this health tech business and she wanted to buy VD.com and she understood. I mean, she had worked for and worked with a lot of Silicon Valley's most famous founders and VCs. She was committed to owning VD.com and she didn't want to pay the price. You know, I won't get it to the numbers, but she didn't want to pay my price. I love that. It was one of my favorite to my names. You say that to all the girls. Yeah.
This one's my favorite. So we're working through ideas on how could this work? And I'm, if anything, I'm extremely open-minded. And so I was just thrown spaghetti against the wall to see what would stick. And I was like, look, give me a piece of equity in lieu of cash.
And she was like, oh, that's an idea. I'm so she went back to her board and they came back and we did a deal. There was some cash. I think there was some milestone cash payments and there was a small piece of equity valued at precisely that delta. There was no funny business. I increased the price. I mean, it was just we're going to make up for that delta between what we're going to pay you in cash and what you want it in cash.
with equity. Can you say milestone based cash payments? What type of milestones or hypothetically? Was it like we raised this round and we gave you a little more than we raised this round, we give you a little more or even just as simple as time. I see your one, your two. Yeah. Yeah. And.
like the leasing idea triggered in my mind that, wow, I can actually act like a venture capitalist, but instead of putting capital money into these companies, I can treat these domain names as capital.
Interestingly, I get the best position on the cap table because in my contracts, if you fail, I just claw the domain back because the equity goes to zero. That's an important clause. Yeah. So it doesn't always work. I mean, it depends on who the company is, who the founders are, what are the chances of negotiation, like anything else. But generally speaking, we've got a clawback clause.
Otherwise, we need to mark up the domain to account for risk. But we started doing that. And so now I don't know. We've got quite a number of startups that we have a piece of equity in that we've literally invested in, but we didn't invest cash. We invested a domain name. And some of them I invested cash on top because I was excited about the opportunity. I've thought about doing this with the podcast occasionally just in a sense because
I do enjoy the startup game at times. I don't want to do it full time. I don't want at this point to have a fund or anything like that. I just don't want to help using the deal with any of that babysitting, frankly. But if I have, as you do, for instance,
A competitive advantage in spotting things that could become very interesting, right? So when someone comes in and you learn about a company that perhaps hasn't launched or hasn't made that quantum leap, but they're on the cusp of having bankroll to potentially buy something where you have a conversation, you realize they're very strategically minded, analytical, like this founder you mentioned. You're like, huh?
Especially with that clawback, that's interesting, as super-diversified business model. It's a lot more interesting than a domain sale. It's like, oh, I get to come along for the ride. So this comes back to another thing, which is that I actually fundamentally believe that we are still in the early stages of domain names and domain name value, early stages of digital commerce and the internet.
Most people in the world have been online for less than 25 years. It's a pretty short period of time. As we see commercial real estate sort of dying and all the distress in the commercial real estate, we're seeing the digital real estate boom. And there's a direct correlation there. I would say a causation. So again, what is a domain name? It's the place where you meet your customer. It's the only place that you own.
that you meet your customer, where it used to be the retail store or the office or the whatever, something brick and mortar. Now it's digital and that digital place where you meet your customer is a domain name. Now, some people have argued and they've for many years, I've heard everything. Originally, it was like, oh, I don't
I remember when absolute vodka launched the first billboard campaign where they didn't advertise their own domain name, they advertised their Facebook page. And I remember seeing that billboard and thinking to myself, how stupid. You are literally, at least, I don't know, 20 cents, I'm pulling a number out of my head, but it's got to be 20, 30% of the equity that you're buying with that billboard is going to Facebook.
And then when the customer goes to Facebook, you don't even own that relationship. You don't own the data. You don't own the relationship. You can be shut off at will. Nothing you could do about it, right? And that was before cancel culture. Now it's like a serious problem. I chatted with this guy ages ago. He was also sort of a snake eater in the shadows, not in a bad way, but like he was very discreet. He was very ethical, but he had these Facebook pages. He would buy Facebook pages.
they were doing well, and then 10x, 20x these pages. And they weren't exactly rollups, but he would accumulate these things. And he had these portfolios. And one of them was just minting money. I can't remember what it was, but it was just like millions and millions dollars a month. And I asked him what it was like having and running that page. And he said,
It's like having the most profitable McDonald's in the world on top of an active volcano. It's like 100% because I just cannot predict what is going to happen. You know it's going to erupt. You just don't know when.
All right, I want to segue here for a second. Speaking of branding, fuckyourself.com. Why did you buy this? This is remarkably timely. I, as I alluded to earlier in this conversation, I get literally thousands of emails a day. Okay, so I am like, I don't know, maybe there's somebody out there that gets more, but I'm kind of like one of the world's power users of email. I get roughly 2,500 to 3,000 emails a day. I don't use a spam filter.
because really in my business, I can imagine a lot of the legitimate emails are kind of indistinguishable from what we get flagged. Oh, yeah. Absolutely. Just the key words that are going to get flagged 100%. So I gave up on spam filters years ago and I just bite the bullet and I've tried a million different things. And always, there's just a some degree of loss I'm not willing to accept. And so I just
literally muscle through it every single day. And it's really the only thing in my life that I'm still I'm captive to. I've really optimized my life for freedom.
except email. Email is still my ball and chain. So at some point, very early, it gets tiring. You get a lot of crazy people and a lot of just garbage. And so somebody presented me with fuckyourself.com and I thought, wow, I want to buy that domain just to have the email address go at fuckyourself.com.
And then I'm going to create an auto responder. And so all of these idiots emailing me, I'm going to literally just email them back from go to fuckyourself.com.
And I cannot tell you how much pleasure that has brought me. I don't know what that says about me, but it truly was one of the best purchases I've ever made in my life. Just so unclear. Everyone who emails you gets an autorespond. No, no, no, no, no, no. It was selective. There were certain emails that I then set up to be autoresponded to, like consistent emails that I would get. They would be put into the file that would be autoresponded directly from goldfuckerself.com. And in other people, I would just use more surgically when appropriate and sometimes inappropriate.
But the problem, I was having fun with it and I still, you know, I get a lot of pleasure from it. But the problem was that it turns out that everybody on earth, in nearly every country from what I can tell, when they fill out a form and they don't want to give their email address, the email address they give is gowithfuckaself.com.
And so go fuck yourself.com literally gets over a hundred thousand emails a day. What? Yes. So it is completely unusable as like, you know, a vanity email address, but it is still fun as a responder. That's funny. You know, that makes me think of, I don't know why this just popped into my head. I think it's kind of funny. Maybe I've seen the big Lebowski too many times, but I went to this wine bar.
Hotel Barone, I think it was in San Francisco at some point. And this was pretty early. This is a long time ago with a lot of the digital signatures at a kiosk of some type when you check out. And I'd had quite a bit to drink and it came time to sign and I asked the guy who was standing there. It's like, how many people just draw dicks? A nice sign. And he was like about 80% of the guys. Come on.
I don't know why that's never occurred to me, but that's literally gonna be the way I signed from now on. But yes, it's in exactly the same vein, pun intended. So brutal. So this brings up, if I miss Segway from fuckyourself.com. This leads very cleanly to anger management. So talk to me about anger management.
Well, I attribute my, let's say, evolution of my anger management to you. I guess it's part of the reason I bought fuckyourself.com. It's part of the reason that I have the reputation I do, which is quite...
I don't want to say belligerent, but I don't suffer fools gladly, and I'm not afraid to speak my mind at all times. I am the self-designated counterweight to political correctness. And so I just like to keep it real. But a part of that is anger. I have a deep emotional anger. It's a fire that burns in me.
and it's not always there but when i get triggered which is fairly often it shows its ugly head and so i would say that in my earlier life it actually serve me well i would have even called it a superpower but as i've gotten older and as i've you know evolved in business and as i've evolved in my marriage and as i've evolved in relationships it's not necessarily my friend and so i've had to find ways to deal with that but it was listening to a podcast that you did
You know, many years ago, talking about yourself dealing with anger issues and anger management, you know, it sort of was the first time I even went, oh, maybe I've got an issue. Maybe this isn't normal. And so, you know, it was that recognition that sort of led me to seek out ways to start dealing with it. And it's an ongoing process. But I think it's a good highlight of things that previously served me.
that no longer do. It even became a part of my identity, both self-inflicted as well as others. And when it's your default, you also find ways to justify it or paint it sometimes in the best light possible. Totally. It's like buying that domain. Totally. And all of a sudden you're like, this is my superpower. Let me create a narrative around that. It may be true in part.
then you create blind spots for yourself. Absolutely, but it's precisely what you said. You create a narrative around it that suits you, you've to justify it, which further engrains it into who you are or who you believe you are. At some point, it stops serving you, and it doesn't have to be anger. It can be many things, many emotions, or maybe just self-identifying characteristics.
And it's very difficult to then change your software and say like, oh, I don't need that anymore. And I'm still working on how to do it, but I made a lot of progress. You didn't outlet for it. So I started boxing. You know, you need to reflect on it constantly to understand where the triggers and understand. Okay, when I get one of these triggers, I need to just.
walk away, stay silent, whatever it might be, but try and find ways to not engage with it. And then always reminding yourself that this isn't who I am anymore or this isn't something I need anymore. This isn't a tool that I need anymore. It's really the way that I look at it.
I wanted to attribute that to you because you've done God's work in a lot of your podcasts and talking about this issue and how you've dealt with it. And that has sent me down a lot of rabbit holes. I'm very good at picking up on these threads and then diving down the rabbit hole and exploring. Well, I appreciate you saying that, man. And I want to also show the cover and title of a book that you brought. So I want to also thank you for
This beauty. So this is how to keep your cool and ancient guide to anger management. And this is by one of my favorites, of course, Seneca the Younger, a very controversial figure for a lot of good reasons. And this is, I want to say on anger, Deita. And I've tried to digest the original.
while not the original. I should say the translated original. This has both. This has both and it's very well done. And when you gave this to me, I said, you know what? I could really use this because I want to revisit it and I listened to it on audiobook last summer, actually, and found it incredibly helpful. It's in some ways similar to an audiobook I listened to, which was
I think it's the easy way to quit caffeine, which is based on a method used for helping people to quit smoking. I think it's called the easy way for quitting smoking. And it's a little hokey, dale, Carnegie-ish, but the fact of the matter is I stopped with a few other elements and did 30 days with zero caffeine for the first time since I was probably so unimaginable for me. Oh, I know, I know, but it was unimaginable for me as well. But it effectively takes you through
all of the reasons and justifications that you use for consuming caffeine and just dismantles them one by one. And I feel like this, how to keep your cool, does something very similar. It makes me feel foolish. It makes me, when I lose my temper, it makes me say, you idiot. What are you doing? You can't even control your temper. What are you doing? So I just keep it on my desk. Really, I reference it, but more than anything, I keep it on my desk and it's a reminder
that when some troll on the internet pisses me off or some, buddy, I'm on the phone with, you know, somebody gets me outraged. Yeah. Because they got an autorespots from go at fuckyourself.com. Oh, dare you. Oh, dare you. It reminds me, it's there. It's in my purview and it reminds me like,
Keep it cool. You have this on your desk as a reminder. Yep. I like that. Yep. Maybe that's all I'll use it. It's hard to miss. It's got like, it's a totally giant. It's orange. Yeah. It's totally. All right. So you mentioned, I want to know if you have any suggestions. You mentioned you might be the world's number one email power user. A lot of people feel beholden to email. Any recommendations for folks?
Or are you just like, hey, man, I need to go to the email methadone clinic too. I don't have any recommendations. Yeah, no, no, no. I'm 100% the wrong person. So I have completely capitulated.
And really, I just muscle through it every single day. I basically accepted that I have about a two and a half hour window every single day where it's just clean the inbox. So first two and a half hours of my day, almost every day are highly caffeinated, muscling through my inbox. And then my, you know, real day starts. Do you just go through G Suite or Gmail or do you use other tools?
I use Apple Mail, but our domain is on Google. But I don't use any filters. I occasionally, let's say every couple months, I'll go in and I'll do the unsubscribe thing. But I honestly find that the more you unsubscribe, the more you get subscribed to other things, I think that that's the hook.
But for the first time in my life, I'm optimistic. I think that it seems like low-hanging fruit, and if there's an AI company super specialized in email filtering, please reach out to me. I would very much welcome your assistance. But I think that AI is going to be a really powerful tool. I think that what I do is replicable by AI. I tried it with an assistance. Twice, I've had an assistant who would at least eliminate the low-hanging fruit.
Teaching them the way I think about it, helping them understand, like, don't delete that. That is actually a really good domain name for XYZ reason. And it's only this crazy library of esoteric knowledge that I've accumulated that allows me to see that diamond in the rough. I mean, if you're getting through 1500 or 2000 email in two and a half hours, I think most people are going to be astonished at the speed. I am really good. So you must archive. I mean, a very high percentage. Yep. Yep. A lot.
If there was like a single place where I would be like, you and I differ more, I think this would be the one. It's like pure chaos. It's pure chaos.
Anybody that works for me is like, what do you mean you just operate from your inbox? Your inbox is just a tool. No, no, no. This is my dashboard. This is like everything is in my inbox, everything. So yeah, so I don't have any tips or tricks. I really just, I welcome the use of AI to, I think, finally be able to replicate what it is I do because it is repetitive.
So I think I can use AI to do that. So I've related to question, which I've been sitting on. I took a note so I wouldn't forget that is related to AI. So more and more people are using chat EPT or bard for various purposes, putting together itineraries. And they're using them in place of, say, Google. The results are very different. And one of the
Narratives out there, which I think it probably has some degree of substance to it, is that it appears that Google got caught with its pants down a little bit with chat GPT, even though I have very high degree of confidence and they like very, very fast progress. But nonetheless, it was because there was a question of how to use this technology
It's also a much larger company and just has sort of machinations and processes that a tiny startup does not. However, what I was going to say is Google has the greatest money maker in the history of the internet. So how do you capitalize on AI without killing the golden goose is an important question. I would imagine trillion dollars as a lay person that
these tools are going to affect the domain world in some capacity. How do you think about that? When social media came on the scene, everybody pushed back and said, well, my domain is less important now. I connect with people on social media. OK, you're going to regret that. And apps came on the scene. And I was like, your domain isn't that important for me. People don't even go to the web anymore. They just use apps. And everybody has 2,000 apps on their phone. And it's like, I'm not sure that's much better, right? And now there's lots of security issues with apps.
Now, Google is basically trying to kill apps, and so every iteration of this, of the way humans interact with the internet, offers up the fresh new death of domain names, okay? But basically domain names are the foundational layer, they're the bedrock layer of the digital world. Everything else is built on top of that. So domain names are some super geeky technologist, hard tech guy is gonna tell me I'm, you know, for the most part, for the consumer internet,
Domain names are layer one that sent him your other response. Yeah. I know there's all these protocols that are underneath that are really the layer one of the internet. I understand that. But for the consumer internet, the part that matters to e-commerce and the consumer domain names are layer one. They're the bedrock foundation of doing commerce on the internet. If we were to stop launching new companies today or
putting out new ideas on the internet because, oh, you can just use chapter JPT or Bard for that. First off, I would love to see the data, but I bet you, like, same as 80% of the people sign the digital signature thing with a dick.
99% of the people using chat GPT are using it for some stupid thing like, what's the best way to peel a banana? It's like these things aren't creating new ideas. They are really good at finding solutions from existing ideas and putting those things together in creative ways and lots of different useful stuff. But if we were to just like get lazy as human species and say, oh,
AI's here. We're done. We don't need to create new companies. We don't need to put out new Wikipedia's or new information or new art.
we literally just stagnate because these things aren't creating that next frontier. They're literally only remixing a stagnant lexicon of art. I guess I'm just wondering how those tools, for instance, and the reason this is top of mind for me is I ran into someone in their 20s who basically uses Bard in place at Google now. Primarily because the point she made was I don't wanna click through all these different links and then click back and have to compare these various things. It'll basically summarize.
put things into tables, etc. for me in a whole bunch of different instances. I thought to myself, well, that's fascinating. I wonder how that will affect the SEO game and impart effect. I think it will tremendously affect the SEO game, and I think it will tremendously affect formula for how to value the main, but I don't think that it's going to tremendously impact.
the fact that we continue to need them. In fact, I think there's an argument to be made that they become even more important. Your domain name needs to be semantically meaningful. It needs to be easy to spell. If you can't use these cute spellings where you're missing a vowel or you're on a .ly or, you know, because people are going to say, take me to Amazon or buy this thing. If you're using an agent, it's like, you know, order me whatever it is, but you need to tell it where to order that thing. And so it becomes even more important to have a really
semantically meaningful domain name. That's my belief. As for Google, there's no way it doesn't cut into that ad business, right? It's just, there's no way. Ultimately, you're going to see some cannibalization of the search business.
I think that's unavoidable. Yeah, it seems to me that unique products will be in a good position. If you are a marketplace selling commoditized products, it's going to be very challenging because I could use an agent and just say, hey, buy this thing at the best price that will get delivered to me in the next two days. Use my MX on file. Well done.
But again, that addresses the SEO in the competition game. But wherever it's buying that thing from, they still need a domain name. Oh, sure. Yeah, totally. Totally agreed. And I think another potential winner, just like you said, I mean, the demise.
You know, the end is nigh for dot coms. I've heard that since I moved to Silicon Valley in 2000. Same thing for email, right? Email is dead. And I'm like, email is not dead. If anything, it's more valuable than ever is more valuable than ever. And I think that is going to continue to be the case as the web becomes a mess of
AI enhanced misinformation, disinformation and just content spamming. I think that domain names are in my opinion. There is a lot of unknowns with AI. I'm not smart enough to think all of that through. There may be a threat on the horizon that I don't see for sure. And I accept that. But.
In my opinion, there is more reason to believe that domain names are about to pop off in a major way because of a couple of things. One is identity and how important it's going to be to be able to verify real identity. And I think that domain names, and I think that like Jack Dorsey is on this, Jack Dorsey understands this,
When he's building around this, domain names are central to everything that he's doing. So your domain name is ultimately like, shouldn't it make sense that in order to get your Twitter handle, your X handle?
you should have them corresponding to my name. If you're, I don't know, NBC, you should have x.com slash NBC. This would be sort of like a very elegant like KYC kind of thing. 100%. So it's literally KYC is the right way to describe it. Know your customer stuff for people who, yeah. Exactly. So across the board from every aspect that you can think of, from financial to social media to e-commerce, people interacting with the internet should be identified by a domain name because it is a
really powerful way to identify somebody. It ties the physical to the digital world. It's that bridge. What do you think the extension will be, or what form do you think that'll take? I mean, a lot of people have dot eth, a lot of people have, then you of course have dot coms, but those could be pricey, right? Do you have any guess for what format that will take?
not going to tell you a timeline, but I think that it's in some future. Most people in the first world that are engaging with the internet on a regular basis are going to have at least two and in some cases three domains. Okay, they're going to have their real identity domain name and that's going to be less important. The more public facing you are, the more pressure there will be to have the dot com, but outside of that,
any extension will do. And then there's going to be your suit, anonymous identity, in which case you really don't care what the extension is. And then there's going to be your sort of commercial identity, whether that's the business you own, the blog you run, but you're going to have at least two. And if you have, let's say you've planted a flag on the internet in one form or another through a blog, a business, whatever it might be,
That's your third domain name. I think most people are going to have two or three domains already today. You can use the dot com domain name and you can use it as a crypto wallet. You can use the DNS records without going too deep into the weeds. You can use the DNS records to.
basically insert your crypto address, your Bitcoin address, or your Ethereum address into the DNS records of your domain name. And then people can send, you know, I've got Drew.com. I can use that as my Bitcoin wallet. And I think that
First feature of why I believe there's this huge growth curve coming for domain names. First is identity, KYC. Second is finance and wallets, specifically wallets, because again, it's the same problem. Yes, you can use some of these web three domains, these.eth, and I was one of the first investors into unstoppable domains. I was literally probably in the first 50 people ever in 2015 to register 1000.eth domains before anybody even knew that what these things were.
I was a huge early adopter of handshake. And there's going to be a lot of people that get upset with me, you know, so I'm going to try not to poo poo poo too much, but I do spend a tremendous amount of time thinking about these things. And I'm very deep in it, obviously. And so I have failed to identify a durable use case for web three domain names. I think they're cute. I think they have some utility. Certainly in its simplest form, they make good wallets.
I don't see a durable utility beyond that. It's definitely better to have Tim.eth or Tim.whatever, web3 domain name, and have that instead of your Ethereum address, which would be some very long hexadecimal string, impossible for most humans to remember.
Also very possible to fuck up. Exactly. That's not the thing you want to mess up, right? Like it's one thing to go to the wrong website. It's an entirely other thing to be sending money to the wrong wallet, but that's actually mixed the point. That's one of the big Achilles heels of web three domains is that there's no standard. I mentioned before I can governs the legacy DNS, the root zone.
If you have an unstoppable domain, you've got Tim Ferriss dot X, they have the dot X, they've got dot wallet, they've got dot whatever. So let's say you've got Tim Ferriss dot or Tim dot wallet and you tell me, hey, send me one if.
can send you one if to Tim dot wallet because today there's only one dot wallet. There's absolutely nothing stopping me from starting a new business tomorrow that also has dot wallet or from the Ethereum name service from launching a dot wallet or there is somebody on handshake that already has dot wallet and there's going to be
Every single blockchain, you're going to see that already in this cycle. But over the next five years, every blockchain that exists is going to have their own domain name service, because it's a very easy money grab. So you're saying there could be bad actors doing bad things with that amount of confusion. Totally. But even if they're not bad actors, there's just going to be a tremendous amount of confusion. Like because you say, hey, send me your need to a Tim dot wallet.
But depending on which wallet I'm using, which wallet software I'm using, I don't know if that's going to the Ethereum blockchain. Is that going to the handshake blockchain? Is that going to the unstoppable? Which blockchain is that on? And so I could send it to tim.wallet and it could go to a different tim.wallet, okay? And I have just nothing I can do about that unless I've got some degree of tech savvy and I can pull down a menu and select which network I want to send this over and that's asking a lot of people.
Wait, wait too much. That's never going to happen. And so for that reason, it's never going to resolve. The second thing is that with decentralization, I think decentralized money is great. I think decentralized information is dangerous. And it comes down to one very simple thing that I find most people can understand.
If you go to the average person and you say, look, there's this one internet over here and it's centralized to a certain degree. And you know, people can shut you down and da da da da da. But it's kind of good enough. It's the internet you know and love. But we got this fancy new internet over here where it's totally decentralized. And believe me, I'm a libertarian. I'm kind of a decentralization maximalist, but I've drawn a line in the sand here for the following reason. And I'll just say, so the peanut gallery doesn't good berserk.
You're also, we don't have time to get into this right now, but huge Bitcoin advocate. Yes. Right. So let's just, just so people know, you're in the game. Yes. Okay. Yes. So please continue in the game for a long time and have a pretty deep understanding. So if presented with two choices of this, here's the internet, you know, in love, here's this
totally decentralized new internet that has all these fancy bells and whistles that you should love, except that there's this one flaw. And that flaw is somebody can put child porn and there's nobody that can ever take it down. And on that singular point,
is when I made up my mind that that will never happen. The Department of Defense, which owns the Department of Commerce, which controls the Internet, a lot of people don't know that, is never, ever, ever, ever going to allow any browser.
to resolve these things. So you've got some fringe browsers that do resolve them, but I think it's something like 98% of all the internet traffic passes through four browsers. It's like Firefox, Safari, Chrome, and Explorer, which is probably a very small market share of these days. But that's basically all the traffic. And I can promise you, I would put virtually everything I have on the fact that those browsers are never going to resolve a Web3 domain name ever, primarily for
Those reasons and other surrounding reasons like that, the inability to ever censor content, as well as the fact that they then lose control to sniff every packet of data that passes through the internet. And so that's never going to happen. It's not going to happen. There may be some parallel, like we've got the dark web now,
But this is never going to be a mainstream thing ever. But I do think they make great wallet addresses to some extent. Today, I think that it could get messy. So you have to be careful. But it's funny, the Ethereum name service guys actually are the ones that figured out how to do this. So they kind of shot themselves in the foot. But you can now take a .com domain name or a .xyz domain name or a .net domain name. And you can use the DNS, the legacy DNS settings. And you can literally make your domain name a wallet.
And so that to me is, that's obvious where we're going to go. All right. So with five minutes left, so I want to before, just in case I get excited and lose track, where can people find media options? MediaOptions.com. If you want to learn more about domain names, we have a mo.co.
No, no, no, I actually recently I just sold emo.co for exactly the same reason I explained I bought it when dot co kind of launched into the public sphere, you know, it was always the extension for Columbia, but then it got sort of repurposed like I did. No, I was kidding. All right. So just yeah, but before we side alley, I don't know options dot com. We've got domain Sherpa dot com, which is our podcast that's about
Domain names. I don't suggest it unless you want to learn about domain names and hear us. And are you active on Twitter? I'm very active on Twitter. Twitter is the only social media I'm at. OK, Andrew Rosen or at Andrew Rosen. We'll link all these things in the show notes. Last question is pursuit of happiness. Small one.
So how do you think about pursuit of happiness? Because I will say, I haven't spent time with you, you strike me as overall pretty happy guy. You got a little methy edge to you, a little twitchy, a little bouncy, but you smile a lot of the time. Yeah, I don't know if you're crying on the inside, but you seem like generally a pretty happy go lucky guy. I'm a pretty content person, content.
Okay, I have moments of happiness, but I'm pretty content. Okay, so tell me more about this and what you. So I guess the way that I think about it is that I generally want to be content. I don't necessarily pursue happiness. I pursue contentment. And is that wanting what you have or being grateful? What does that mean?
Yes, I think that's another way of saying it, but for me personally, it's a bit more that Terence McKenna had this theory of novelty that ultimately that's what evolution is all about. It's just about the pursuit of novelty.
And that resonated with me. And I basically surmised that I think the purpose for each of our individual lives is truly if you zoom out and you look at it from a species focus as opposed to an individual focus. The purpose for each individual life is actually just novelty. It's about unique characteristics that make you you and how you engage with the world around you and what that leads to. And this novelty is actually the objective or should be the objective.
Again, in my opinion, meaning there's like a variety of.
different characteristics, survival of the fittest, is that have an arity? Sure, not necessarily. I think survival of the fittest is a mechanic in the game, but it's not necessarily the end all be all of the game. I think it's really just about the pursuit of novelty, that you need to do things that nobody's done before. You need to react to things in a way that is not typical. If you do things like everybody else has done things, or like everybody else does things, then you can't expect a different outcome than what everybody else has had.
And I certainly am not looking for the outcome that everybody else has. You've got one shot at this thing. I want to do something else. I want to stand out. I want to pursue greatness or whatever that means. But I certainly, above all else, I don't want to be like other people. I don't want to be like anybody else, like any other individual or like any other group of individuals and like labels. I just want to pursue novelty. And what I found that to mean once you go another layer is that really what
Most of life is actually friction and pain and suffering. And we have developed our society to run away from that. You have a right to happiness. You are, should be in the pursuit of happiness. And I think that makes us soft. I think that makes us avoid risk. I think that makes us avoid pain. It makes us avoid hard work and
Everything that I've seen, everything that I enjoy comes at the expense of pain, suffering, hard work, whether that's my marriage, it's a lot of work, it's a lot of pain and compromise, but through that you achieve love and you achieve this amazing relationship that's irreplaceable. Through those days of suffering and doing whatever it takes to make $250 a day,
I was able to build a business that makes, you know, a lot of money and fits my lifestyle. I've optimized it for exactly the way I want to live. I don't want to scale it. I want to have 60 employees. I have four, five. And I want to just keep doing what I'm doing, just hold my scale and hold my scale and just love what I do. But all of that takes suffering and pain. You know, I think the best way to highlight it is like art. Show me one meaningful piece of art, cultural art.
that came as a result of like rainbows and butterflies and happiness. Great art comes from pain, suffering, heartache, mental illness, just terrible circumstances. It's really, great art comes from the darkness, not from the light, but you need both. And if you ignore the darkness, you will never get the light, or you'll always be chasing the light. The light will always be in the distance, but you have to lean into the pain.
Off camera, we were talking about something else and you were sitting, you know, I just sit with it. And that's precisely it. You have to sit with the pain. Don't block it out. Don't ignore it. Don't push it away. Run into it. Run into the pain, run into the hard stuff, run into the stuff that nobody else wants to do. Because that's how you achieve novelty and through novelty, you achieve everything. Anybody, it doesn't matter what your definition of success is. I can assure you that that person is successful by whatever definition you're holding them up to be.
through novelty. They did something that other people were afraid to do, that other people didn't think of. Whatever it is, it was achieved through novelty. And as far as I can tell, all greatness is achieved through novelty. It's doing things that other people don't want to do, doing things that other people are afraid to do, doing things that other people wouldn't even think about doing.
And normally, the delta between those things is pain, suffering, heartache, it's, you know, the darkness. Which could take a lot of forms, right? Like could take the form of being ridiculed. Absolutely. Right. As an example. Absolutely.
Absolutely. And that's just tip of the iceberg. It's like, you know, the soft stuff. That's the nerf baseball. Exactly. Exactly. Once you get through the nerf bat, there's another guy standing there with a real Louisville. Yeah. So for yourself then, because you and I think are cut from similar cloths in a number of respects, one of which not just our bald head, not just the bald head and and striking good looks, not just our resemblances to Jason Statham, but
Also, I think you wrestled. I know if you're wrestling coach and your experience wrestling had a huge formative impact on you. Huge.
I'm not sure if people with high pain tolerances gravitate to wrestling or if it cultivates it or both. Check in the egg problem. Yeah, check in the egg problem. And there are other ways, of course, that people develop high pain tolerances. I think you need to have childhood trauma and learn to dissociate. I mean, actually a lot of people who have that experience in childhood end up being, for instance, very high level military operators, huge correlation. Don't think that's a coincidence. And my question is,
related to my own experience. I look at... Great entrepreneurs, by the way, usually have daddy problems. It's another thing to look at when you're making investments. It's like, how's your relationship with your dad? Oh, it's great. Terrible. Okay, knees over. So, I'll be around too with Dr. Rosner unpacking daddy problems for entrepreneurial success. So, the experience that I've had, and I think I've contended with it to a large extent, but because I have high pain tolerance,
and it has been a competitive advantage. I've sometimes ended up running towards painful things that are not worth doing, which seems like it can be a necessary cost if you are pursuing worthwhile novelty, but just the fact that something is painful does not justify its pursuit, right? Absolutely not. So I'm wondering for yourself how you navigate that, because even now I sometimes hear the siren song, like it's tempting because I've been rewarded for that in the past.
But as I get older, I'm like, all right, time is fleeting. I need to be more surgical about how I approach these things, especially if I'm trying to moderate my tendency towards anger, right, which I think those two often go hand in hand. Absolutely. Right. So how do you think about that? Simple. Very important to have North Star, right? So what are you optimizing for? What do you want for me?
thanks to Charlie Tuna. I was lucky that I learned very early on in my career. I had, let's say, a role model, not for everything, but for certain things about how I wanted to live my life. I thought, wow, if you were to ask me when I was a junior in college, like, oh, what do you want to be me to grow up? I want to be like a billionaire tech entrepreneur with thousands of employees in this huge company that everybody knows. And then it was like, Charlie Tuna taught me like, whoa, that's the opposite of what you want.
No, no, no, no. You want to like definitely you want to achieve financial freedom, but that's just like step one. You know, you want real freedom. You want free will. So I optimize for that. And so I decide, is this worth pursuing? Is this going to help me achieve more or less freedom in my life? I was about to build a business. We were going to start a new company called Pegasus.
a year ago now, six months a year ago, I don't know. And we spent six months planning this thing out, got a CTO. We were ready to rock. And it was in the domain business. It wasn't like I was venturing into something totally new. It's a business that I've never been so sure I would have been successful in this business. I know it would have been successful.
But we got to the one yard line. We're about to do it. And I asked myself, like, I was laying in bed and I'm thinking myself, like, literally tomorrow, I'm going to have this team meeting and we're going to basically green light this and we're going to start putting this in action. And that means I'm going to hire a bunch of people. And that means I'm going to be flying all over to have meetings. And I was like, I don't want any of that. I was like, I don't even know, like,
