Please enjoy this transcript of my interview with Andrew Rosener (@andrewrosener), the founder and CEO of MediaOptions, which has been the #1 domain broker in the world for the last six consecutive years. Since 2008, Andrew has been involved in more than $600 million dollars 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.
DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:
Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.
WHAT YOU’RE WELCOME TO DO: You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the tim.blog/podcast URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.
WHAT IS NOT ALLOWED: No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on tim.blog or (obviously) license photos of Tim Ferriss from Getty Images, etc.
Tim Ferriss: I usually have a pretty good idea of where I’m going to start these conversations and I’m looking at this list and it’s a combination of Memento meets Forrest Gump meets globetrotting, and I’m going to let you choose. So should we start with — and this will be very back and forth, we’re going to 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?
Andrew Rosener: Whoa. All right, let’s start with Charlie Tuna because it inspires all else.
Tim Ferriss: Perfect. Who the hell or what the hell is Charlie Tuna?
Andrew Rosener: 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, 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 and 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 with 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 Moehrke. So I get a call from Peter Moehrke, and Peter says, “Do you want to come sell fish?”
Tim Ferriss: How did he get your name or number or both?
Andrew Rosener: So Peter contacted University of Rhode Island where I went to school. He 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.
Tim Ferriss: That’s what we call foreshadowing, folks.
Andrew Rosener: 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 him 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 at first sight, 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 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.”
Tim Ferriss: What was he wearing?
Andrew Rosener: He was wearing a Native American poncho type of thing. And he’s got long hair with a ponytail and this unique beard that, I don’t know, only Peter could 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. And 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.
Tim Ferriss: Isn’t always the weapon suited to the task?
Andrew Rosener: 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 —
Tim Ferriss: Beneficial to Peter.
Andrew Rosener: 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. The fish business is a cash business basically worldwide. And so it lends itself to certain elements and it was just an amazing life experience.
Tim Ferriss: So walk me through what it looks like, let’s just say your first week or month on the job. How is the compensation set up and what are you actually trying to do?
Andrew Rosener: 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 Atlas Shrugged?” I said, “No.” He said, “Have you ever heard of it?” I said, “No.” He says, “Do you know who Ayn 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, what are you saying?” He’s like, “Go read this book. Don’t come back in until you’re done.” So I literally, I went home and I literally took about five days to read the book. It’s a big book.
Tim Ferriss: It’s not a short book.
Andrew Rosener: No, it’s not. It’s a big book, and it’s not easy reading either. At least the first 200 pages, it’s a 200-page intro. And so I read the book, I came back in, it was kind of like a fifth grade, what do you call that? Like a book —
Tim Ferriss: Book report?
Andrew Rosener: Book review. And I don’t know, I guess I passed. That was it. And then it was like, “Okay, look, come with me.” And he took me down to New Bedford, Massachusetts and drove me around to these different scallop-processing facilities. And I met some absolutely crazy people. Amazing, amazing people. These are just truly — to this day, I was just actually back in Rhode Island 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 it brought me right back. Really just amazing people. You just don’t — I’m sure there’s other industries like that, but seafood is a really special, truly salt-of-the-earth business and it’s such a dichotomy from the business I’m in today.
Tim Ferriss: In that boiler room, what did exactitude mean? Why was it on the wall?
Andrew Rosener: I think it means different things to different people. To Peter —
Tim Ferriss: To Peter.
Andrew Rosener: 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 imprecision.
Tim Ferriss: So once you’ve read Atlas Shrugged, which I’ll admit I’ve not read, but —
Andrew Rosener: Oh, must.
Tim Ferriss: I know. So shame unto me. Once you’ve read that, you come back five days later, at that point, is it some form of arbitrage? What is the —
Andrew Rosener: Basically.
Tim Ferriss: Business model?
Andrew Rosener: Yeah, basically. So what’s remarkable is Peter’s business is still going today. I think it’s got to be 40 years now. I think it was 30 years — it’s got to be 40 years now. I think he started in 1985, so roughly 40 years, 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 its, let’s say, core business is scallops, and all of his competition, 100 percent of his competition, 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, et cetera. And despite these seeming disadvantages, Peter has been nimble and he’s kept his overhead low and through the good times and the bad, he’s just kept that business running. And in great times —
Tim Ferriss: And is he buying and then reselling?
Andrew Rosener: Buying, putting in his packaging, in some cases — I don’t know if we want to go into that today, but let’s call it value-add.
Tim Ferriss: We can skip certain details if —
Andrew Rosener: They would say they’re value-adding and repackaging and then reselling. And it’s pure arbitrage.
Tim Ferriss: 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?
Andrew Rosener: They were doing about seven or eight million a year when I started.
Tim Ferriss: And how did it grow?
Andrew Rosener: So 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 35,000,000, which is a lot of scallops.
Tim Ferriss: How do Hokkaido scallops fit into this picture?
Andrew Rosener: So —
Tim Ferriss: Northern island of Japan, for people who may not know.
Andrew Rosener: A couple of years in — so basically, this is a pure sales game. 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.
Tim Ferriss: And you’re selling to distributors, to restaurants, to —
Andrew Rosener: No, no restaurants. Primarily distributors, other wholesalers, restaurant supply companies, cruise lines.
Tim Ferriss: Got it.
Andrew Rosener: So I say no restaurants, but large restaurant chains, which is where we’re going with this story. But a couple years in, I come across Benihana and I call up the Fort Lauderdale headquarters at Benihana and, “You guys want to buy some scallops?” And it’s just pure luck that they happened to be in a transition period where they’d been getting all of their seafood from one company and they decided that they could get better pricing and there was other advantages by —
Tim Ferriss: Put out a bid.
Andrew Rosener: Put out a 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, I did my due diligence on the buyer, and he was Nicaraguan by descent, and he loved 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, it was literally, 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, and American scallops are great. Arguably, if you’re getting them pure form, which it’s very difficult, it’s the best in the world. However —
Tim Ferriss: Pure form, meaning unadulterated?
Andrew Rosener: Unadulterated, within a couple of days.
Tim Ferriss: Not imitation crab meat type of scallop?
Andrew Rosener: Yeah. Yeah. That’s the least of your worries. It’s the value-adding part that’s not so —
Tim Ferriss: You’re eating Guinea pigs.
Andrew Rosener: So the interesting part of this was basically, American scallops are graded zero to 10, 10 to 20, 20 to 30. And that’s basically zero 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 zero to two, two to four, four to six, six to eight, eight 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 plates to be consistent, you can’t be, “That one plate has four scallops, one plate’s got six, and oh, well, I’ve got this one giant scallop, and so now my plate cost is thrown off.”
So that inconsistency, and 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 there was 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 Benihana worldwide, all their scallops, and I subsequently became basically the world’s leading expert on Hokkaido scallops.
Tim Ferriss: So was it a known fact in the industry that Hokkaido scallops had these advantages?
Andrew Rosener: No. Nobody cared.
Tim Ferriss: So how did you —
Andrew Rosener: Nobody cared because they were taking the packaging that came from Japan, and they were just repacking it into American standards. 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.
Tim Ferriss: So what made you good? We’ve spent a good amount of time together, so I have some guesses, but rather than guess, what do you think made you good at this job?
Andrew Rosener: I’m not afraid to sell. I think I have to start there, is that I’ve just — I took it for granted that, I don’t know, “Oh, hand me a phone book. I’m going to start making cold calls.” I’m going to get on the phone with people, try and sell them something that they —
Tim Ferriss: Never knew they needed.
Andrew Rosener: Never knew they needed. I think that was a big factor. And then I’ve got the gift of 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 —
Tim Ferriss: Where they are.
Andrew Rosener: Where they are. You got to meet the person where they are and understand what they need, and then craft your message and craft 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. 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. I think that that’s —
Tim Ferriss: All right. So to tie up just a loose end here and bring this boomerang back to the initial question for a minute. So is Bruce Wayne to Batman as Peter is to Charlie Tuna?
Andrew Rosener: 100 percent.
Tim Ferriss: They’re one and the same?
Andrew Rosener: One and the same.
Tim Ferriss: All right. So what —
Andrew Rosener: And Charlie Tuna, he was a squash player. Peter influenced me in ways way beyond business. His lifestyle, I had never seen somebody with that lifestyle.
Tim Ferriss: What was his lifestyle?
Andrew Rosener: Well, again, he’s an old hippie who had been — he was playing the long game. He had this little business and he loved it, and it made a couple million bucks a year every year. And good times, he made more and bad times, maybe made a million bucks, but it was a great business. And he’d just been chugging along, chugging along.
He had no ambitions of scaling. I came in, I’m fresh out of college and business school, and I’m like, “Well, we can do this and we can automate this and we can do a lot.” And he’s like, “Look, shut up kid. Just keep chugging.” And he would take off. He’d go down to Belize for a month and he had 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 watch whales break in the surface. And he didn’t aspire for the things — I guess at that time, 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, 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 into squash.
Tim Ferriss: So what are the tenets of Charlie Tuna, or some of them?
Andrew Rosener: 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 identified as things that he would just say a lot. And they’re just these short little phrases that get a certain point across. And 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 tenets of Charlie Tuna because it just sounds better, but it’s like, “I’m not Mother Teresa; I’m here for a profit.” Because you get customers and they’re like, “Well, can you do this for me? I really, dah, dah.” And I think, “Look, I’m here for business. If I was here to make friends, 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.” And unabashedly. Or, “Don’t be backwards about going forwards.”
Tim Ferriss: What does that mean?
Andrew Rosener: Well, people do things in these roundabout ways. Just be direct. Just say what you want to say. Do what it is you want to do. Don’t —
Tim Ferriss: Beat around the bush.
Andrew Rosener: Dance around it. Don’t beat around the bush. There’s 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.
Tim Ferriss: The mourners?
Andrew Rosener: Yeah, “Don’t crowd the mourners.”
Tim Ferriss: Okay. There’s still some riddles unsolved.
Andrew Rosener: That one I never got a clear answer to.
Tim Ferriss: All right. I feel like we were having sushi at one point and you were like, “Something, something in the whorehouse.”
Andrew Rosener: Oh, yeah. One of the better ones, “You can’t run a whorehouse without any whores.”
Tim Ferriss: All right, on its face, this makes sense, but what did that mean in the business?
Andrew Rosener: But 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. We’re not trying to be Walmart. 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’d better have scallops. If you want to run a domain brokerage, you’d better have the best domains in stock, right? 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 whores, because generally they’re trying to avoid risk, right? They’re trying to de-risk.
Tim Ferriss: I imagine some people listening would say, “Well, hold on a second…” I keep wanting to call him Charlie. I guess that’s fine. But Peter ran a really —
Andrew Rosener: Tight shop.
Tim Ferriss: Tight shop. He seemed to carry much lower overhead and fixed cost because he wasn’t virtually 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?
Andrew Rosener: Too slow.
Tim Ferriss: You’ve missed the window?
Andrew Rosener: Missed the window.
Tim Ferriss: Got it.
Andrew Rosener: Miss the window. It’s a commodity, so you don’t have it, the next call is your competition. Very little differentiation. It’s a commoditized product.
Tim Ferriss: 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 scallops, last I checked, don’t last forever. So if you’re holding inventory, it’s not like you can sell the next Christmas.
Andrew Rosener: 100 percent. I don’t know how deep down this rabbit hole you want to go, but that was one of our superpowers was, and another way that Peter has really influenced me was, Peter had lived all over the world. He dodged the Vietnam draft and went to Namibia. 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. In Chile, in Peru, we had —
Tim Ferriss: Pablo the Catch.
Andrew Rosener: We had Mr. Lucky in China, and we had —
Tim Ferriss: Mikey the Iron Wrench.
Andrew Rosener: Crazy, really. And he just knew these people and he would call them up and he’d just say, “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 every single morning.
Tim Ferriss: And that’s in terms of catch, type of catch?
Andrew Rosener: Yeah.
Tim Ferriss: Or catch may not be the right term, but —
Andrew Rosener: Yeah. A lot of these guys, they came to appreciate Peter and his personality. He’s truly a character, and the method. But 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 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 extraordinarily long period of time. And so it got them to trust me, it 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 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 and to understand which part of the market. So when you say you’ve got to have the whores 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 redheaded whatever. So I need to know that the thing that’s going to be short in the market is going to be 30, 40 size scallops, 20, 30 size scallops, whatever. I need to know what’s going to be short.
Because the stuff that’s going to 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 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 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. 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.
Tim Ferriss: We’re going to move from tuna as in the namesake of Batman/Charlie Tuna. We’re going to move from scallops to jamón ibérico.
Andrew Rosener: It’s a good segue.
Tim Ferriss: We’re going to move from food to food.
Andrew Rosener: Okay. It’s a good segue.
Tim Ferriss: Where does this fit into your life story?
Andrew Rosener: So 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 jamón ibérico, pata negra. 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 —
Tim Ferriss: With people nodding in the room.
Andrew Rosener: 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 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, learned about the internet. I thought, “Wow, domain names, amazing.” I started registering them because I’m hyperactive, and every time I had 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 jamón ibérico 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 intention. I discovered that it was actually illegal. The FDA did not allow you to import this jamón ibérico because it’s cured for 18 months. 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 that was that. And I put it in the closet and forgot about it.
And then a couple years later, I’m driving to my office and I hear on NPR radio that George Bush is about to get the first jamón ibérico ever legally imported into the United States, and I couldn’t believe it. And I got to my office and I found out who the importer was, and I called him up and started talking shop. And I told him I wanted to buy a ham from him. And he was like, “Look, kid, I’m sold out for a year. I basically have a monopoly.” Or he had a monopoly. And these were like, I don’t know, seven, eight, $10,000 legs of ham at that time. And it’s literally, it’s a whole leg.
Tim Ferriss: Wow. Buying a thoroughbred.
Andrew Rosener: He was like, “You have no chance. Forget it, get in line.” We’re talking shop and it came up that I had these domains, and it was like his proverbial jaw dropped. He immediately was like, “How much do you want for those domains?” It was the first time — like I said, I bought a lot of domains at that point already, but never thinking, “These are valuable assets that I’m going to sell in the future.” It was always like, “This is another lame-brained idea that I’m going to try and build a business around that I never got around to.” I didn’t even know what to answer, so I said, “I want one of your hams,” and he goes, “No problem, done.” I was like, “Wait, that’s too easy,” so I was like, “$5,000,” and he’s like, “Done.” I was like, “The ham’s got to come from that first container, George Bush’s container,” and he’s like, “Done.” I was like, “Wow, okay.” I was like, “All right, it’s yours.”
Tim Ferriss: Yeah.
Andrew Rosener: 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. I just took the leap of faith, transferred him to domains, a couple of weeks later, I got a coffin in the mail and the rest is history. That moment then gave birth to my whole domain business. I realized that this 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.
Tim Ferriss: Now, where or when does Tess Diaz into the picture?
Andrew Rosener: Tess Diaz worked for GoDaddy, and GoDaddy, at this time, again, 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,” 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 a thousand 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. Anyways, Tess 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 Please Farm.
I had a lot of time, so she called me and she said, “What are you doing with all these domains?” I was like, “I have no idea. Every time I have an idea, I buy them.” She said, “There’s a domain industry and there’s people trading these things and you can monetize them.” I was like, “I had no idea, tell me more.” Literally, I spent three or four hours on the phone with her getting a download on — that there’s a domain industry and an aftermarket and there’s people on forums talking about these things and there’s different ways to park them and monetize them and, “Google will pay you for the clicks.” This was all new to me, but it was fascinating. 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.
Tim Ferriss: By that point?
Andrew Rosener: Yeah, by that point. 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.” The shot clock ran up and it ran up at the same time that I was doing this deep dive into this domain world. What I realized was there was nobody playing matchmaker between the people that had these domains, who were fascinating characters. Literally, you would be hard-pressed to find an industry that has such a motley crew of extremely successful and 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. There was people trading amongst themselves, 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. More importantly, playing educator between this nascent asset class and the broader business environment that I think recognized, “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 the various benefits of owning them. Therein was born Media Options. My wife and I founded it together, and I think it was maybe a year or two later that Tess — Tess became my account rep at GoDaddy, just going full circle here, and then ultimately, left GoDaddy to come to work for me. I went from a Lone Ranger to plus one.
Tim Ferriss: VP of sales.
Andrew Rosener: Yeah. Shortly thereafter, we moved to Panama. We left Rhode Island and moved to Panama.
Tim Ferriss: If we take a 30,000-foot view for a second for folks who are unfamiliar with the domain/domaining 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. There’s an aftermarket, there are auctions, expiries, dnjournal.com, dnforum.com, domainnamewire.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?
Andrew Rosener: Like any market, it has a structure, there’s a clear texture and structure to the market. Let’s say, at the lowest level, you’ve got guys that 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 register 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 those are primary registrations.
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, Yani, 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 the opposite. I’m, basically, 100 percent on instinct and then I back it up with data, but I primarily am operating from instinct. Either way, we utilize primarily the same tools as the SEO industry to gauge what the total addressable market of these domains is.
There’s a whole bunch of different tool providers in the domain industry to 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 the — X. Another segue we can go down, but X is really where the material domain world is meeting these days. There’s investors coming out at this from a lot of different angles, and then you’ve got some of the names that you mentioned, Domain Name Wire, DN 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. Remarkably important organization, by the way, that very few people know even exists, and more people should know that they exist. There’s all these different layers, 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 is just inherent traffic, people just inherently go to these domain names.
Tim Ferriss: Prime.com?
Andrew Rosener: Yeah, prime.com. People want to go to Prime at Amazon, they just type in prime.com. 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. 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. At scale, that can be considerable revenue, and that used to be the primary business model in the early 2000s.
Tim Ferriss: Let’s capture that traffic, hope it leads to click-throughs on your advertising, and then get paid by Google.
Andrew Rosener: 100 percent.
Tim Ferriss: 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 O, right? Google, three Os, and I land on that page. How much do you think the owners of some of these misspellings pull in?
Andrew Rosener: I’m going to pause for a second, because this is a really important point that I want to make. I would say, 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 Os 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 — 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. Like, “You’re just a dirty domain squatter.” It was a really bad — 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. Anyways.
Tim Ferriss: Really. There are VCs who own just —
Andrew Rosener: Yeah.
Tim Ferriss: — spreadsheets full of domains?
Andrew Rosener: More targeted, super high quality, maybe tens of domains, but really high quality.
Tim Ferriss: Are they holding them for portfolio companies or are they looking to —
Andrew Rosener: I don’t know, I don’t know.
Tim Ferriss: Can I play stand-in for the listeners for a second?
Andrew Rosener: Sure.
Tim Ferriss: All right.
Andrew Rosener: Please, do.
Tim Ferriss: This differentiation, I think, is important to underscore, squatter versus investor. Do investors still buy URLs that represent trademarks owned by other people? If so, how is that reconciled?
Andrew Rosener: 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 cybersquatting laws now, it’s quite punitive, $100,000. If you get sued in federal court, it’s $100,000 per name penalty, for infringing on somebody’s trademarks, cybersquatting. There are also much cheaper, faster, and easier mechanisms for recovering domain names that infringe on your trademark called the UDRP, Universal Domain Resolution —
Tim Ferriss: Protocol?
Andrew Rosener: Protocol.
Tim Ferriss: I’m just guessing.
Andrew Rosener: I think it’s “Protocol.” Basically, there’s three elements, and if you could prove those three elements, the domain’s going to immediately get transferred to you, okay? It’s 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. 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. Then that’s it, you’re going to get to the domain name assuming they —
Tim Ferriss: You don’t need to know the identity of the holder for that.
Andrew Rosener: Nope, you don’t.
Tim Ferriss: Got it.
Andrew Rosener: There’s very strong mechanisms both preventing and, let’s say, clearing the market. There’s very little upside to doing this anymore. Like I said, there’s still bad actors, but it’s a very small problem compared to what it used to be.
Tim Ferriss: When did you put up your shingle and start the company?
Andrew Rosener: 2008.
Tim Ferriss: I’m no historian, but 2008 doesn’t sound super early in the domain game.
Andrew Rosener: No.
Tim Ferriss: Which makes it more interesting to me, because it’s not day one of Google AdWords where you’re shooting fish in a barrel, right? There’s a point in time where it was like, “Yeah, we can just look at the dictionary and go buy a bunch of dictionaries.”
Andrew Rosener: Totally.
Tim Ferriss: At this point, it would seem like you are 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 X —
Andrew Rosener: Nor would almost anybody else like.
Tim Ferriss: Like x.com, right?
Andrew Rosener: Yeah.
Tim Ferriss: I don’t know who would use it for what. I know it’s a single letter, okay. Could 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 had been, a lot of them, removed, right? Right, so then how do you determine a fair price?
Andrew Rosener: I’m taking a wild guess here, but just for emphasis, literally, probably 95, 98 percent of our business is domain names that were registered prior to 2000. In 2008, when, as you 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 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 wanted to continue this hobby, I needed to generate cashflow to support it, okay? That was one of the premises of starting Media Options. 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 for ourselves.
Tim Ferriss: People would come to you and say, “I have fillintheblank.com and I would like to sell it, but I’m not sure how to do it.”
Andrew Rosener: A line out the door. One thing that is — 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 a domain and they expect it’s going to sell the next day. Anybody that can help them achieve that unrealistic objective, they are banging on the door. Yes, I have literally — it could be a segue into a million things, but let’s stay here. I get so many emails every day of people that want me to sell their domains, so endless supply of inventory to sell. I start banging on doors and, basically, playing fake it until I make it, because nobody had really done this before, so I was —
Tim Ferriss: How did people find you at that point?
Andrew Rosener: Most of the people that owned 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, so I’m meeting these people on the forums.
Tim Ferriss: I see.
Andrew Rosener: There’s DN Journal, which does this weekly sales report. At that time. Today, I’m 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.
Tim Ferriss: It would get published on the forums?
Andrew Rosener: Yeah. It’d get published in DN Journal, that was a source of pride. It was like, “Look, my sale got published in DN Journal this week.” People would see that you sold a domain for a good price and then double down on. That was how the people that owned the domains were finding me.
Tim Ferriss: Were finding you, got it.
Andrew Rosener: I’m finding the people that I was trying to sell them to, okay? Very rarely are they coming and finding me. Did happen, right? Lightning strikes —
Tim Ferriss: Do you still remember any of your initial sales where you’re like, “Holy shit, I think this could be a thing.” Do you remember?
Andrew Rosener: The sale where I thought, “Wow. Okay, I think I’m going to be able to make this into a business,” was pizza.net, which —
Tim Ferriss: This is a great example, because it seems like there are a lot of people you could potentially sell that to. Walk us through pizza.net then.
Andrew Rosener: Pizza.net was a unique case, pizza.net was a very famous domain, because it was highlighted quite prominently in the movie The Net with Sandra Bullock in 1994.
Tim Ferriss: Really?
Andrew Rosener: Yeah. This is a 1994 movie 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. Man, it’s another rabbit hole, but 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.” They have a patent on that. Pizza.net was doing that prior to Google filing that patent, so pizza.net technically had —
Tim Ferriss: The company that owned pizza.net was doing that type of proximity —
Andrew Rosener: 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.
Andrew Rosener: He was the guy that literally strung the internet cable up the entire East Coast of the United States. He literally put in the actual hardware that created the first internet network on the East Coast of the United States.
Tim Ferriss: Okay.
Andrew Rosener: Adam — I can’t remember his last name, but Adam something.
Tim Ferriss: We’ll put it in the show notes.
Andrew Rosener: Yeah.
Tim Ferriss: We’ll also put the rest of the tenets of Charlie Tuna in the show notes, for people who are wondering where those might be found.
Andrew Rosener: 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 until about ’94, ’95. Regular home adoption didn’t really happen until ’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, it was a read-only or write-only. It was mostly tech, not in the way that we think about it today, but 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. He had a lot of very, very good .net domain names at a time when he could have registered any of them in .com. There’s so many ways to segue this, but he actually is the guy that — he originally registered — 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 —
Tim Ferriss: Why are there only three?
Andrew Rosener: I’ll tell you the story. Adam actually registered all other 23, okay? Numbers aren’t allowed, single numbers are just not allowed for security conflicts. Prevented by ICANN from being registered. He went and registered all the other one-letter .com domain names, but because he wasn’t using them, ICANN then decided, “This is a bad idea, nobody should be able to have these one letters,” so they pulled back all but the three which they grandfathered in, because Nissan was using z.com for their 300Z car, which was quite popular at the time. I think Quest Communications was using Q, and Elon as it were, was using X at the time. It was actually originally owned by a lawyer and Elon bought it from him prior to merging with Peter Thiel for PayPal.
Those three got grandfathered in and the rest got pulled back. I have read quite a bit about it. I think the way ICANN was thinking about it was like maybe there was an element of security, they’re a socialist organization, 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 —
Tim Ferriss: Clawed them all back except for three.
Andrew Rosener: Yeah.
Tim Ferriss: Okay.
Andrew Rosener: Yeah.
Tim Ferriss: Got it. Pizza.net.
Andrew Rosener: Pizza.net, 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. I earned probably a $20,000 commission on that, probably the owner made $100,000 net, more or less, and that was a lot of money for me. I had this mantra. At that time, I had just left the job where I was making about three, 400 grand a year consistently, and I was 26 years old, or 25 years old, whatever it was. I was making a lot of money, way more than any of my peers. I literally jumped ship, moved to Panama, started this brokerage business, and I had a limited amount of savings. I had 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.
Tim Ferriss: How did you arrive at that number?
Andrew Rosener: I calculated what my annual expenses were going to be in totality and divided by the number of business days. And it was really that simple, and this is another thing, it came from Peter. It was like, look, keep your expenses low. All my competitors, they were doing sort of different things, but they were all trying to be very technical about it and build scalable businesses and lots of people and lots of technology and huge overhead. And at that time, I had basically no overhead. And so anyways, I was turning along and doing whatever it took.
I would give away a domain name just to make $250 that would say it 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. It was just punishment. It was like, okay. So anyways, I really stuck to that and I think that that was a very powerful discipline for me in that first year.
Tim Ferriss: But in brief, because I know a lot of folks listening are going to wonder, why Panama?
Andrew Rosener: So we originally planned to move back to Europe and 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 just thought, okay, well, it’s going to just be more of the same in Europe. Germany would’ve been the obvious next step. So we kind of said like, “Okay, we really want to escape that environment, particularly we’re going to launch a new business. I need some positivity. What I don’t need is constant negative vibes around me all the time.”
The other thing was that 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. She had a manual car. She was driving up a hill in Providence, and she got stuck in the snow.
Tim Ferriss: I can imagine the German curses.
Andrew Rosener: 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. We visited a lot of places in the Caribbean and we’d gone to Central America, and 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 the currency friction of volatility.
Tim Ferriss: Didn’t even think of that.
Andrew Rosener: 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 point a half percent GDP growth in 2008 or 2009, whereas China was number two with 11 percent. Right. So huge GDP growth.
Tim Ferriss: Why was there so much GDP growth?
Andrew Rosener: Well, Panama —
Tim Ferriss: So banking sector, or no?
Andrew Rosener: Well, yeah. So the banking sector was growing rapidly. The Panama Canal was expanding, and as global — we were basically really, let’s say for that first decade of the 2000s, that was kind of peak globalism. It was like, “Wow, everybody’s doing trade with everybody.” That got sort of short-stopped with the financial crisis, but things were booming.
So anyways, Panama ticked all the boxes. That was really why we landed on Panama.
Tim Ferriss: So you’re in Panama, pizza.net. Holy shit, this is going to cover a lot of $250 days.
Andrew Rosener: Totally.
Tim Ferriss: Right. This could be a business.
Andrew Rosener: It was super important that I was hyper-focused on earning $250 a day, which you’re going to 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 I lost the discipline of the $250 a day, but I started hunting bigger fish with the inherent confidence that came with achieving this discipline of hitting these small targets.
Tim Ferriss: So, hunting bigger fish.
Andrew Rosener: Yeah.
Tim Ferriss: This then brings us back to the question of valuations and acceptable cost. So how do you think about this? Or how should people think about it is too broad. But how do you think about it?
Tim Ferriss [PSA to listeners]: 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.
[Conversation resumes.]
Tim Ferriss: 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 too.
It says: “Startups, in particular, should not buy their domain name. They should lease the best possible .com domain name to their business with an optional path to buy later.” Can you elaborate on this?
Andrew Rosener: Yeah. Yeah. So this is a big decision/important decision/terrifying risk for a lot of startups —
Tim Ferriss: Why do you say what you just said?
Andrew Rosener: — or they wait and then they get, extorted is a strong word, but done in. They really get bent over the barrel because they purchase —
Andrew Rosener: Extorted is not actually the worst-case scenario. The 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. Now explain why.
So about 2015, okay, 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, and when I say investors, I mean really primarily VCs, as well as startup founders. 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 when the .com boom happened, but a lot of those like early .com successes were coming back for their second shot in that sort of time period.
Tim Ferriss: Yeah, that’s true. I mean I can for sure confirm that, because I was in Silicon Valley at the time and a lot of guys who had their first win in 2007, ’08, ’09, or maybe that’s when they started a company and they had just taken some secondary off the table, so maybe they had an IPR, but they were flush with cash and they were looking to build more things.
Andrew Rosener: Yeah.
Tim Ferriss: I saw this a lot, 100 percent.
Andrew Rosener: So I think, like anybody who is successful, they learned 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 market is crowded and now there’s a million people that want to compete with me and there’s a lot more resources to fund those people who want to compete with me, 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.
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 it’s actually a de-risking. A lot of —
Tim Ferriss: I want to make sure we talk about leasing.
Andrew Rosener: Yeah. This is why we’re going to circle back to this, okay?
Tim Ferriss: Yeah.
Andrew Rosener: Now this is actually directly leading into the leasing.
Tim Ferriss: Let me, just to straw man this a little bit, if somebody is in a weak cash position and then it could be risky to overpay in the early stages —
Andrew Rosener: Sure. But this is where it’s going to dovetail into the leasing. Because I think regardless of the cash position that you’re in — not regardless completely, but within a realm, it’s a better strategy — leasing rather than an up-front, just all-out purchase.
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 who could afford to buy them, and there was some companies offering financing, but at very high rates and not super attractive to most businesses.
So I was trying to come up with ways to increase the pool of potential buyers and increase my ability to close sales. So I thought well, you know, we’re all — I say we’re all, because I actually owned 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.
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, it’s been a downhill slope ever since. We used to get the lion’s share of 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, “I’ll give $10 million for that domain that you leased to this guy for a thousand dollars a month,” nothing I can do about it.
We use escrow.com, is one of our biggest partners, a third-party escrow service. I would encourage anybody doing a domain transaction, in my opinion the only — maybe if he is a lawyer, but other than that the only safe way to conduct a domain transaction. It used to be owned by Fidelity. 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, who are the 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 into the sunset, you might not even ever have to talk to me again if you don’t want to.
Tim Ferriss: Quick question. So with escrow.com, who mediates a dispute where you say —
Andrew Rosener: It goes to arbitration.
Tim Ferriss: Okay. It goes into arbitration?
Andrew Rosener: Yeah. Third-party arbitration.
Tim Ferriss: And they organize all of that, or is that something you guys organize?
Andrew Rosener: 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.
Tim Ferriss: Yeah. I’m not saying — if it were —
Andrew Rosener: If it were, it goes through a third-party forum, arbitration forum.
Tim Ferriss: Yeah. Okay. And they will basically organize that?
Andrew Rosener: Yeah. Because they’re the ones holding the domain. They’ve got an interest in sorting this out as quickly and amicably as possible. So they hold the domain. There’s usually a payment up front which basically buys you an option, which like 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 either they know they’ve got a business and their raising either more funds, or their profitable, or they achieve some level of scale, but they either have a business or they don’t. 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.
So generally, rough back-of-the-napkin math, the way these things usually fall is like somewhere around five percent, it could be 10 percent, the bigger the value usually the numbers come down, the lower the percentage.
Tim Ferriss: So it’s over that five-year period, you mean?
Andrew Rosener: Yeah. So the purchase option — and it’s important that the startup have some skin in the game —
Tim Ferriss: Oh, I see. That’s the initial option cost?
Andrew Rosener: Yeah. The initial option —
Tim Ferriss: Not the total cost during the five-year —
Andrew Rosener: Yeah. 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 usually be like a half a point.
Tim Ferriss: So does that option-up-front payment act as an advance in the case that you purchase?
Andrew Rosener: In most cases, yes. Generally speaking, we apply that option fee, so let’s say that you approach me, you want to buy a domain, that domain is $100 thousand, we agree to one of these lease deals. Maybe you’re going to put five or $10 thousand down up front, and then you’re going to have a 90 or $95 thousand fixed price option to buy.
Then you’re going to have a lease component, and the lease component is a true lease. Payments don’t go towards the purchase price, but it’s half a point. So like if it’s a $100 thousand domain, you might be paying $500, or maybe $1,000 a month. It’s a half a point or a point a month, which is going to get the owner of the domain a reasonable, conservative rate of return of five to 12 percent 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 the cost to keep your floor clean to operate on your exact brand match .com from day one.
So that’s the first element if 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 re-brand 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 thousand per employee to do a domain name re-brand, to move from one domain to another. Particularly it’s higher and higher and higher the later stage you are in the organization and the more complexity you have.
So you are leasing the domain, you’re operating right from the get-go, you look like you’re a serious business right from the get-go. You’re not try this or get that.
Tim Ferriss: So a question to you on the sell side, because now I’m super interested in this. Now I’m thinking 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, and they’re like, “I’m not in the domain-selling business, I’m actually in the domain-leasing business.”
Andrew Rosener: Yeah.
Tim Ferriss: 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.
Andrew Rosener: Do you care, though? Really?
Tim Ferriss: I’m curious what it is.
Andrew Rosener: 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 saying to myself I’ve got about 5,000 really good domain names. Let’s just take the top 500. These would all be domain names that like, at an absolute minimum, you’re talking about $100 thousand, and that would be cheap, so $100 thousand and up. Some of these are eight figures. Some of these are seven figures. Some of these are mid-six figures, like $100 thousand to many millions of dollars, okay, 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. That’s $250 thousand a month in totally passive income. And when I say passive income, like you would be hard-pressed to find more passive income, because it’s not like a real estate portfolio, where once in a while you’ve got a pissed-off tenant.
Tim Ferriss: There’s a dead rat in the HVAC — you’ve got to fucking deal with it.
Andrew Rosener: Yeah. You’ve got to deal with broken pipes and electricians. Then you’ve got local and state real estate taxes. Then you’ve got dah, dah, dah, dah, dah, dah. 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.
So 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. 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 domain names or acquire a domain?”
From there the concept evolved in my head to the point where it’s really a no-brainer. So even if you have the money, like, why lay out the cash if you can lease 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’s literally going to cost you in most cases less than you pay to keep your floor clean in your office to have this domain name.
Like 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, I am, I don’t know — IAmVida.com. I’m an investor in a company called Vida, which is a good segue into another element of this that you sort of referenced.
But, anyways, it’s a lot easier to raise capital going and saying, “We are Vida and we have vida.com,” rather than, “We’re Try Vida,” or “We’re vida.io,” or “We’re vida.xyz.” You’re not a serious company. It’s like you’re on training wheels.
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 $1 billion that isn’t on a .com. You’d be pretty hard-pressed. I think there’s only one Fortune 1000 company that is not on a .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 it was, the auditors, whoever it was, came in and said, “You guys need to own all your IP before we’re going to take you public.” So last minute they had to go out and buy fb.com from 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 ID.
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 this huge risk. We’re looking for 100X here. We want you to be a $10 billion company or $100 billion company, and you can’t do that without your .com. 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 just an inherent risk.
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 downsize 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.
Tim Ferriss: Vida — you mentioned you were an investor, and you said that relates to another element of this. What is that other element?
Andrew Rosener: Yeah. So I mentioned that just because — so Stephanie Tilenius, who was a very early employee at Yahoo and PayPal, I think in 2012, Woman of the Year in Technology, phenomenal founder, she approached me to buy vida.com. She didn’t want to pay —
Tim Ferriss: V-I-T-A?
Andrew Rosener: V-I-D-A.
Tim Ferriss: Okay. V-I-D-A?
Andrew Rosener: Yeah. The Spanish word for life.
Tim Ferriss: Yep. Got it.
Andrew Rosener: She was building this health tech business and she wanted to buy vida.com, and she understood — I mean she had worked for and had worked with a lot of Silicon Valley’s most famous founders, and she was committed to owning vida.com, and she didn’t want to pay the price. I won’t get into the numbers, but she didn’t want to pay my price. I loved that. That was one of my favorite domain names.
Tim Ferriss: You say that to all the girls, “This one is my favorite.”
Andrew Rosener: So we were working through ideas on how could this work, and if anything, I’m extremely open-minded. So I was just throwing spaghetti into the wall to see what would stick, and I was like, “Look, give me a piece of equity in lieu of cash.” She was saying, “Oh, that’s an idea.” So she went back to her board and came back and we did a deal.
There was some cash, I think there was milestone cash payments, and there was a small piece of equity valued at precisely the delta. There was no funny business. I didn’t increase the price. It was just we’re going to make up for that delta between what we’re going to pay in cash and what you wanted in cash with equity.
Tim Ferriss: When you say milestone-based cash payments, what type of milestones? Or hypothetically? Was it like “We raise this round and we give you a little more, then we raise this round and give you a little more?”
Andrew Rosener: Yeah. Or even just as simple as time.
Tim Ferriss: Got it. Your payment schedule?
Andrew Rosener: Yeah. And that deal, like the leasing idea, triggered in my mind that 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, and interestingly I get the best position on the cap table because in my contracts, if you fail, I just claw the domain back, because your equity goes to zero. So that was —
Tim Ferriss: That’s an important clause.
Andrew Rosener: Yeah. So it doesn’t always work, right? I mean it depends on who the company is, who its founders are. It’s a negotiation like anything else. But generally speaking we’ve got a clawback clause. Otherwise we need to mark up the domain to account for the risk. But we started doing that, and so now, I don’t know, we 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. In some of them I invested cash on top because I was excited about the opportunity, but —
Tim Ferriss: I thought about doing this with the podcast occasionally, just because in a sense 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 LPs to 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. 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 and you realize they’re very strategically minded, analytical, like this founder you mentioned, especially with that clawback, that’s interesting.
Andrew Rosener: That’s super interesting.
Tim Ferriss: That diversified business model.
Andrew Rosener: And quite literally it just interests me. 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 I actually fundamentally believe that we are still in the early stages of domain names and domain value, the early stages of digital commerce and the internet.
Most people in the world have been online for less than 25 years. That’s a pretty short period of time. As we see commercial real estate sort of dying and all the distress in commercial real estate, we’re seeing digital real estate boom, okay? And there’s a direct correlation there. I want to 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, you know, 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 — I remember when Absolut 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.” Like you are literally at least, I don’t know, 20 — I’m pulling a number out of my head, but it’s got to be 20 or 30 percent 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 could be shut off at will. Like there’s nothing you could do about it, right? And that was before cancel culture. Now it’s like a serious problem.
Tim Ferriss: I chatted with this guy ages ago. He was also a snake eater in the shadows, not in a bad way, but 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. They weren’t exactly roll-ups, 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. It was just millions and millions of 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, because I just cannot predict what is going to happen.”
Andrew Rosener: You know it’s going to erupt, you just don’t know when.
Tim Ferriss: All right, I want to segue here for a second. Speaking of branding, Fuckyourself.com, why did you buy this?
Andrew Rosener: This is remarkably timely. Well, so as I alluded to earlier in this conversation, I get literally thousands of emails a day. Okay. So I am — 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.
Tim Ferriss: Okay.
Andrew Rosener: I don’t use a spam filter. And because really in my business, it’s all about the —
Tim Ferriss: I can imagine a lot of the legitimate emails are kind of indistinguishable from what would get flagged.
Andrew Rosener: And 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 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 captive to. I’ve really optimized my life for freedom except email, email’s 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 autoresponder. And so all of these idiots emailing me, I’m going to literally just email them back from Go@fuckyourself.com. And I cannot tell you how much pleasure that has brought me. I don’t know what that says about me, but literally, it truly was one of the best purchases I’ve ever made in my life.
Tim Ferriss: Just so I’m clear, everyone who emails you gets an auto-response?
Andrew Rosener: No, no, no, no, no, no, no. It was selective. It was selective. There were certain emails that I then set up to be auto-responded to, like consistent emails that I would get. They would be put into the file, they’d be auto-responded directly from Go@fuckyourself.com, and then 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 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 Go@fuckyourself.com. And so Go@fuckyourself.com literally gets over 100,000 emails a day.
Tim Ferriss: What?
Andrew Rosener: Yes. So it is completely unusable as a vanity email address, but it is still fun as a responder.
Tim Ferriss: Oh, that’s funny. That’s funny. You know what 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 bar —
Andrew Rosener: No such thing as too many times —
Tim Ferriss: At Hôtel Biron, I think it was, in San Francisco at some point, and this was pretty early, this was a long time ago, with a lot of the digital signatures at a kiosk of some type when you check out, and I had had quite a bit to drink, and it came time to sign. And I asked the guy who was standing there, like, how many people just draw dicks when they sign? And he was like, “About 80 percent of the guys.”
Andrew Rosener: Come on.
Tim Ferriss: Yeah!
Andrew Rosener: I don’t know why that’s never occurred to me, but that’s literally going to be the way I sign from now on.
Tim Ferriss: All right.
Andrew Rosener: Yes, it’s exactly the same vein, pun intended.
Tim Ferriss: Oh, God.
Andrew Rosener: So brutal.
Tim Ferriss: All right. This brings up, if I may segue from Fuckyourself.com, this leads very cleanly to anger management. So talk to me about anger management.
Andrew Rosener: 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 —
Tim Ferriss: Aggressive? Aggressive?
Andrew Rosener: 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 anyways, a part of that is anger. I have a deep — I don’t know, 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 served me well. I would’ve even called it a superpower.
But as I’ve gotten older and as I’ve 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 deal with that. But it was listening to a podcast that you did many years ago talking about yourself dealing with anger issues and anger management. It sort of was the first time I even went, “Oh, maybe I’ve got an issue. Maybe this isn’t normal.” And so it was that recognition that 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. And then figuring out how to — it even became a part of my identity, both self-inflicted as well as others.
Tim Ferriss: For sure.
Andrew Rosener: It becomes a part of like —
Tim Ferriss: And when it is your default, you also find ways to justify it or paint it sometimes in the best light possible.
Andrew Rosener: Totally.
Tim Ferriss: It’s like buying that domain.
Andrew Rosener: Totally.
Tim Ferriss: And all of a sudden you’re like, “This is my superpower. Let me create a narrative around that.”
Andrew Rosener: Yeah.
Tim Ferriss: And it may be true in part, but then you create blind spots for yourself.
Andrew Rosener: Absolutely. But it’s precisely what you said. You create a narrative around it that suits you to justify it, which further ingrains it into who you are or who you believe you are. And at some point it stops serving you.
And it doesn’t have to be anger. It can be many things, many emotions, or maybe many 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’ve made a lot of progress, you need an outlet for it, so I started boxing. You need to reflect on it constantly to understand what are 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 trying to find ways to not engage with it.
And then always reminding yourself that this is not something, this isn’t who I am anymore or this isn’t something I need anymore. This isn’t a tool that I need anymore, is 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 am very good at picking up on these threads and then diving down the rabbit hole and exploring. So.
Tim Ferriss: 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: An 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.
Andrew Rosener: Yeah.
Tim Ferriss: De Ira. And I’ve tried to digest the original, well, not the original, I should say the translated original.
Andrew Rosener: This has both.
Tim Ferriss: 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. And 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 18.
Andrew Rosener: That is so unimaginable for me.
Tim Ferriss: Oh, I know, I know. But it was unimaginable for me as well.
Andrew Rosener: Yeah.
Tim Ferriss: 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.
Andrew Rosener: 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?” 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 somebody I’m on the phone with, somebody gets me off.
Tim Ferriss: Someone’s outraged because they got an auto response from Go@fuckyourself.com.
Andrew Rosener: Yeah! How dare you!
Tim Ferriss: How dare they!
Andrew Rosener: It reminds me, it’s there. It’s in my purview and it reminds me, like, keep it cool.
Tim Ferriss: So you have this on your desk as a reminder.
Andrew Rosener: Yep.
Tim Ferriss: I like that.
Andrew Rosener: Yep.
Tim Ferriss: Maybe that’s how I’ll use it. It’s hard to miss. It’s got like a giant stop sign —
Andrew Rosener: Totally. And it’s orange.
Tim Ferriss: Yeah.
Andrew Rosener: Yeah.
Tim Ferriss: It’s a giant stop sign.
Andrew Rosener: Totally.
Tim Ferriss: 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 for that.”
Andrew Rosener: Yeah, no, no. I am 100 percent the wrong person. So I have completely capitulated and I really — I just muscle through it every single day. I basically have 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 real day starts.
Tim Ferriss: Do you just go through G Suite or Gmail or do you use other tools at all, or you just —
Andrew Rosener: I use Apple Mail, but our domain is on Google.
Tim Ferriss: Got it.
Andrew Rosener: 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 assistant twice. I’ve had an assistant who would at least eliminate the low-hanging fruit. But 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.
Tim Ferriss: I mean, if you’re getting through 1,500 or 2,000 emails in two and a half hours, I think most people are going to be astonished at the speed.
Andrew Rosener: I’m really good.
Tim Ferriss: So you must archive, I mean, a very high percentage of this.
Andrew Rosener: Yep, yep, a lot. It’s literally, I think if there was a single place where I would be like, you and I differ more, I think this would be the one. It’s — 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 welcome the use of AI to, I think finally be able to replicate what it is I do. It is repetitive. So I think I can use AI to do that.
Tim Ferriss: All right. I have a related question.
Andrew Rosener: Yeah, go.
Tim Ferriss: So I have related 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 ChatGPT 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 kind of caught with its pants down a little bit with ChatGPT, even though I have a very high degree of confidence that they’ll make very, very fast progress.
Andrew Rosener: Yeah. Yeah.
Tim Ferriss: 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 moneymaker 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 —
Andrew Rosener: A trillion dollar question —
Tim Ferriss: — as a layperson, that these tools are going to affect the domain world in some capacity. How do you think about that?
Andrew Rosener: 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.” Okay, you’re going to regret that.
Then apps came on the scene and it was like, “Oh, your domain isn’t that important for me. People don’t even go to the web anymore. They just use apps.” And then everybody has 2,000 apps on their phone and it’s like, eh, I’m not sure that’s much better. And now there’s lots of security issues with apps, and 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 going to tell me — but for the most part, for the consumer, internet domain names are layer one.
Tim Ferriss: Instead of your auto response.
Andrew Rosener: 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 ChatGPT or Bard for that, right?” First off, I would love to see the data, but I bet you same as 80 percent of the people sign the digital signature thing with a dick, 99 percent of the people using ChatGPT are using it for some stupid thing like “What’s the best way to peel a banana?” Right?
But 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 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 Wikipedias or new information or new art.” We literally just stagnate because these things aren’t creating that next frontier. They’re literally only creating or remixing a stagnant lexicon of art.
Tim Ferriss: 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 of Google now, primarily because the point she made was, “I don’t want to 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, et cetera, for me in a whole bunch of different instances.” And so I thought to myself, well, that’s fascinating. I wonder how that will affect the SEO game and in part affect all these things.
Andrew Rosener: I think it’ll tremendously affect the SEO game. And I think it will tremendously, or may tremendously, affect the formula for how to value a domain, 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 because suddenly it becomes, like — semantically, your domain name needs to be semantically meaningful, it needs to be easy to spell. You can’t use these cute spellings where you’re missing a vowel or you’re on a .ly because people are going to say, “Take me to Amazon,” right, or, “Buy this thing.” If you’re using an agent, it’s like, “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. It’s an excellent question. There’s no way it doesn’t cut into that ad business. There’s no way. Ultimately you’re going to see some cannibalization of the search business. I think that’s unavoidable.
Tim Ferriss: 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, just say, “Hey, buy this thing at the best price that will get delivered to me in the next two days. Use my Amex on file.” Boom, done. The other winner, I think that might emerge —
Andrew Rosener: Again, that addresses the SEO and the competition game. But wherever it’s buying that thing from, they still need the domain name.
Tim Ferriss: Oh, sure.
Andrew Rosener: Right?
Tim Ferriss: Yeah, totally, totally agree. And I think another potential winner, just like you said, I mean the demise, the end is nigh for .coms, I’ve heard that since I moved to Silicon Valley in 2000.
Andrew Rosener: Yeah.
Tim Ferriss: Same thing for email, right?
Andrew Rosener: Totally.
Tim Ferriss: “Email is dead,” and I’m like, email is not dead.
Andrew Rosener: If anything, is more valuable than ever —
Tim Ferriss: It’s 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 —
Andrew Rosener: Domain names are, in my opinion — okay, now, there is a lot of unknowns with AI, and I’m not smart enough to think all of that through, all right. 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, and he’s building around this; domain names are central to everything that he’s doing. So your domain name is ultimately, shouldn’t it make sense that in order to get your Twitter handle, your X handle, you should have the corresponding domain name? If you’re, I don’t know, NBC, you should have —
Tim Ferriss: Got it. So this would be —
Andrew Rosener: X/NBC. x.com/nbc.
Tim Ferriss: This would be a sort of very elegant, like KYC kind of thing.
Andrew Rosener: 100 percent. 100 percent. So it’s literally, KYC is the right way to describe it.
Tim Ferriss: Sorry, guys. “Know your customer” stuff for people who, yeah.
Andrew Rosener: 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.
Tim Ferriss: So here’s the question. Do you think that’s going to be —
Andrew Rosener: It ties the physical to the digital world, it’s that bridge.
Tim Ferriss: What do you think the extension will be, or what form do you think that’ll take?
Andrew Rosener: What do you mean?
Tim Ferriss: Well, do you think it’ll be — I mean, a lot of people have .eth, a lot of people have, then you of course have .coms, but those could be pricey. If I were to — do you have any guess for what format that will take?
Andrew Rosener: I’m not going to tell you a timeline, but I think that 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. Basically, the more public facing you are, the more pressure there will be to have the .com, okay. But outside of that, any extension will do. And then there’s going to be your pseudonymous identity, in which case you really don’t care what the extension is. And then there’s going to be your 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 domain names. Already today, you can use a .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 — like, I’ve got Drew.com. I can use that as my Bitcoin wallet. And I think that — so first feature of why I believe there’s this huge growth curve coming for domain names.
First is identity KYC. Okay? Second is finance and wallets, specifically wallets, because again, it’s the same problem. It’s like, “Yes, you can use some of these Web3 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 a thousand .eth domains before anybody even knew 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. So I’m going to try not to poo poo too much, but I do spend a tremendous amount of time thinking about these things, and I am very deep in it, obviously.
And so I have failed to identify a durable use case for Web3 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 like 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.
Tim Ferriss: Also, very possible to fuck up.
Andrew Rosener: Exactly. That’s not the thing you want to mess up, right? 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 actually makes the point. That’s one of the big Achilles heels of Web3 domains is that there’s no standard. I mentioned before, the ICANN governs the, let’s say the legacy DNS, the root zone.
If you have, I don’t know, an unstoppable domain, you’ve got timferriss.x, okay, they have the .x, they’ve got .wallet, they’ve got whatever. So let’s say you’ve got tim.wallet. Okay, easy, tim.wallet. And you tell me, “Hey, send me one ETH.” I can send you one ETH to tim.wallet because today there’s only one .wallet, but there’s absolutely nothing stopping me from starting a new business tomorrow that also has .wallet or from the Ethereum name service from launching a .wallet. Or there is somebody on Handshake that already has .wallet, and there’s going to be, every single blockchain is within that. 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. And —
Tim Ferriss: So you’re saying there could be bad actors doing bad things with that amount of confusion?
Andrew Rosener: Totally. But even if they’re not bad actors, there’s just going to be a tremendous amount of confusion.
Tim Ferriss: Confusion, confusion. Yeah.
Andrew Rosener: Because you say, “Hey, send me an ETH to the tim.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, and I have, there’s 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.
Tim Ferriss: Yeah, that’s asking a lot of people.
Andrew Rosener: Way 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 people can shut you down and dah, dah, dah, 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.
Tim Ferriss: And I’ll just say, so the peanut gallery doesn’t go berserk. You are also, we don’t have time to get into this right now, but a huge Bitcoin advocate.
Andrew Rosener: Yes.
Tim Ferriss: Right. Just so people know, yes, you’re in the game.
Andrew Rosener: Yes.
Tim Ferriss: Okay.
Andrew Rosener: Yes.
Tim Ferriss: So please continue.
Andrew Rosener: 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 and 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 Justice, 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 —
Tim Ferriss: That’s wild. I had no idea.
Andrew Rosener: — 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 percent of all the internet traffic passes through four browsers, right? It’s like Firefox, Safari, Chrome, and what was the —
Tim Ferriss: Explorer?
Andrew Rosener: Explorer, which is probably a very small market share 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 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, it’s like that’s obvious where we’re going to go.
Tim Ferriss: All right, so we have five minutes left. All right, so I want to before, just in case I get excited and lose track, where can people find Media Options?
Andrew Rosener: Mediaoptions.com. We have, if you want to learn more about domain names, we have a —
Tim Ferriss: It’s not mo.co? No, I’m kidding.
Andrew Rosener: No, no. I actually, recently I just sold mo.co for exactly the same reason I explained. I bought it when .co kind of launched into the public sphere. It was always the extension for Columbia, but then it got sort of repurposed like —
Tim Ferriss: No, I was kidding. All right, so just, before we side alley.
Andrew Rosener: Mediaoptions.com.
Tim Ferriss: Mediaoptions.com.
Andrew Rosener: And we’ve got domainsherpa.com, which is our podcast that’s about domain names. So I don’t suggest it unless you want to learn about domain names and hear us —
Tim Ferriss: And are you active on Twitter?
Andrew Rosener: I’m very active on Twitter. Twitter’s the only social media I’m active on.
Tim Ferriss: Okay. Andrew Rosener @AndrewRosener. We’ll link to all these things in the show notes.
Last question. The pursuit of happiness. So how do you think about the pursuit of happiness? Because I will say having spent time with you, you strike me as overall, a pretty happy guy. Yo’veu got a little methy edge to you, A little twitchy, a little bouncy, but you smile a lot of the time.
Andrew Rosener: Yep.
Tim Ferriss: I don’t know if you’re crying on the inside, but you seem like generally a pretty happy-go-lucky guy.
Andrew Rosener: I’m a pretty content person.
Tim Ferriss: Content.
Andrew Rosener: Content. I have moments of happiness, but I’m pretty content, I think is the right —
Tim Ferriss: Okay. So tell me more about this and what you —
Andrew Rosener: 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.
Tim Ferriss: Is that wanting what you have or being grateful? What does that mean?
Andrew Rosener: 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. And so —
Tim Ferriss: Meaning there’s a variety of different characteristics, survival of the fittest, is that how the novelty —
Andrew Rosener: Sure. Not necessarily. I think survival of the fittest is a mechanic in the game, but it’s not necessarily —
Tim Ferriss: The end all be all.
Andrew Rosener: 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 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. It’s just not, I got one shot at this thing, I want to do something else. I want to stand out. I want to pursue greatness, 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 any other group of individuals. I don’t 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, is actually friction and pain and suffering. And we have developed our society to run away from that. We’re always, “You have a right to happiness, you 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 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 build, I don’t want to scale it. I don’t want to have 60 employees. I want to have four, five. I want to just keep doing what I’m doing, just hone my skill and hone my skill and just, I love what I do, but all of that takes suffering and pain. I think the best way to highlight it is art. Show me one meaningful piece of art, cultural art that came as a result of rainbows and butterflies and happiness, right. Great art comes from pain, suffering, heartache, mental illness, just terrible circumstances. 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.
You have to — off camera, we were talking about something else and you were saying, I had to 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.
Again, 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 the darkness —
Tim Ferriss: Which could take a lot of forms, right? Like, could take the form of being ridiculed.
Andrew Rosener: Absolutely.
Tim Ferriss: Right? As an example.
Andrew Rosener: Absolutely. Absolutely. And that’s just tip of the iceberg. That’s like the soft stuff. Yes.
Tim Ferriss: That’s the Nerf baseball bat.
Andrew Rosener: Exactly, exactly. Once you get through the Nerf bat, there’s another guy standing there with a real Louisville.
Tim Ferriss: So for yourself then, because you and I think are cut from similar cloths in a number of respects, one of which —
Andrew Rosener: Not just our bald head?
Tim Ferriss: Not just the bald head and striking good looks, not just our resemblances to Jason Statham, but also I think you wrestled.
Andrew Rosener: Yes.
Tim Ferriss: I know your wrestling coach and your experience wrestling had a huge formative impact on you.
Andrew Rosener: Huge.
Tim Ferriss: And I’m not sure if people with high pain tolerances gravitate to wrestling or if it cultivates it, or both.
Andrew Rosener: Chicken and the egg problem.
Tim Ferriss: Yeah, chicken and the egg problem. And there are other ways, of course, that people develop high pain tolerances. I think you could have childhood trauma and learn to dissociate. I mean, I actually a lot of people who have that experience in childhood end up being, for instance, very high-level military operators. A huge correlation. Don’t think that’s a coincidence. And my question is related to my own experience. I look at —
Andrew Rosener: 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.” “Um, okay. Meeting’s over.”
Tim Ferriss: That’ll be round two with Dr. Rosener. Unpacking daddy problems for entrepreneurial success.
So the experience that I’ve had, and I think I’ve contended with to a large extent, but because I have a 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 it 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?
Andrew Rosener: Absolutely not.
Tim Ferriss: So I’m wondering for yourself how you navigate that, because even now, I sometimes hear the siren song. 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, which I think those two often go hand in hand.
Andrew Rosener: Absolutely.
Tim Ferriss: Right? So how do you think about that?
Andrew Rosener: Simple. Very important to have a North Star, right? So what are you optimizing for? What do you want? Right? 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 when you grow up?” “I want to be like a, I don’t know, billionaire tech entrepreneur with thousands of employees and 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. Definitely, you want achieve financial freedom, but that’s just like step one. It’s like you want real freedom, you want free will.
And 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? Right? I was about to build a business. We were going to start a new company called Pegasus about, I don’t know, 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’ve been successful in this business. I know it would’ve been successful. But we got to the one-yard line, we were about to do it, and I asked myself, I was laying in bed and I’m thinking to myself, so, literally tomorrow I’m going to have this team meeting and we’re going to basically greenlight 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.”
There was a deep part of me that, I don’t know if imposter syndrome is the right word. I’ve achieved a pretty high degree of, let’s say, financial freedom. But my business, most of your audience would probably say my business is garbage. Like, ah. And the reason being is I can’t scale it. I can’t sell it.
Tim Ferriss: You might be surprised, but I understand what you’re saying.
Andrew Rosener: Maybe.
Tim Ferriss: But, there will be a subset.
Andrew Rosener: Totally. Traditional metrics of let’s say, what makes a good business. My business doesn’t meet that description, but my business is amazing for me, and I don’t want it to be for somebody else. I want it to be for me. And so I run it the way I want to run it. And it brings me back to a tenet of Charlie Tuna. If you pay for the microphone, you get to say what you want to say.
Tim Ferriss: That resonates for me.
Andrew Rosener: And that comes from, I think it was Ronald Reagan who said it in a presidential debate. He said, or no, I think it was George Bush, Sr. And he said, “Excuse me, but I paid for this microphone.” Somebody tried to cut him off.
Anyways, I optimize for freedom. I optimize for freedom of deciding what to do with my time outside of email. I optimize for being able to live where I want to live. I optimize for being able to move if I want to move. I optimize for spending time with my children, especially while they’re young. I optimize for, I eat dinner with my family every single night at 6:30. Every single night, 6:30 with almost zero exceptions, 6:30, I’m sitting at the dinner table, but 6:30, I’m sitting at the table having dinner with my kids and my wife.
I optimize to be able to, I’m going to leave in two weeks and I’m going to Thailand for two months, and then we’re going to bounce around, we’re going to go to Laos, we’re going to go to Vietnam, and I’m going to go explore Thailand for two months. And there was this thing inside of me that I hadn’t built a business that I could sell. And there was this box that I felt like I hadn’t yet, and that was the driving force for “I’m going to build Pegasus.”
Pegasus is going to be — basically, we had a clear path that we could in five to seven years, build this into a $5 billion company. And I think we could do it. But I got to that one-yard line, and I ran down the checklist of the things that I want in my life and 99 percent of the things that I was going to get from Pegasus was the opposite of what I wanted in my life. And so it was like, boom. I literally went the next day. I told everybody, I said, “I’m super sorry,” but literally, just cut the head off the Pegasus. Right? “It’s dead. This is not happening.”
Tim Ferriss: Yeah. Got it. Okay. So that answered my question, which was why didn’t it get spotted sooner? Right? So it was that.
Andrew Rosener: Yeah, I had this driving thing. I had this thing, this itch that I felt like I needed to scratch. But I think it’s important, and this is directly to your point, everybody’s got those itches that they want to scratch, but ask yourself why. Where did that idea come from? That idea came because that was what everybody else wanted to do. That was the common narrative. If you go on x.com right now, you are going to see there’s a bazillion people that are startup porn and hustle porn. And it’s like, “I haven’t slept in four days,” and they’re proud of it. And it’s like, no, I want seven and a half or eight hours of sleep every night. I’m optimizing for that.
And granted, in the early days of starting the business, there’s a lot of nights that I’m not getting that and there’s a lot of suffering and a lot of pain. But I was able to suffer through the pain and the hardship and the extraordinary hours and the blah, blah, blah, blah. Because I had this North Star, I knew that there was a light at the end of the tunnel. And that light wasn’t some ambiguous goal that somebody else gave me. It was actually what I wanted. It was actually what Charlie Tuna had taught me about how I wanted to live my life. I wanted to be free. I wanted to be able to not answer to anybody for anything, except my wife, and literally just live my life as I choose.
If you inspired me right now with some idea that achieve some of these things that I want in my life, close business tomorrow, or let the guys run it and guys, I’m out and I don’t know, go live in the Amazon. I want that optionality, even if I’m never going to take it. I want that optionality at all times. And I don’t ever want to feel like I have to make a decision because of somebody else’s —
Tim Ferriss: Agenda.
Andrew Rosener: Agenda.
Tim Ferriss: Priorities.
Andrew Rosener: Exactly. Exactly. So I hyper-optimize for that.
Tim Ferriss: Thank God for Charlie Tuna, huh?
Andrew Rosener: Thank God for Charlie Tuna, really. Actually, if I were to say the three most important influences in my life, it would be wrestling from an early age. I started at five, and this is hilarious, because literally our coach, salute Wayne Griffin, one of the top wrestling coaches in America. It’s not, say, in Ohio or Pennsylvania. He used to write in marker across our forehead or in a meet, he’d write it across our headgear, “Pain is temporary, pride is forever.” And I guess that stuck with me. It started at an early age.
And then I was very lucky. My parents really modeled for me, I want to say this because I think it’s also one of the elements that defines success for me is it’s also super pertinent to what we’re saying. My parents have been married 40 years, 50, 50 years, 50 years, 50 something, 52. And I think that a long-enduring, mostly loving marriage is one of the most underrated elements of success in the world. Maybe the most underrated. I am self-destructive. If it wasn’t for my wife, man, it’s a binary outcome. I’m either dead or I don’t know, eccentric billionaire doing things that don’t represent any of the things I’ve just described to you as what I actually want in my life.
Tim Ferriss: Howard Hughes putting his urine in milk bottles.
Andrew Rosener: A hundred percent. A hundred percent. I’m going to save you that story.
Tim Ferriss: Round two. Daddy issues and urine-drinking.
Andrew Rosener: It certainly wasn’t easy, but they modeled for me what were the minimum requirements to have an enduring relationship. And so that was really important. And then Charlie Tuna. Charlie Tuna really just took it away, and, yeah.
Tim Ferriss: What a fucking crazy story, man. Your life is amazing. It’s so wild.
Andrew Rosener: Every day, I really believe I have the best job in the world because every day I’m engaging with just super interesting people.
Tim Ferriss: You and I have different paths to the same thing.
Andrew Rosener: Yes, a hundred percent. A hundred percent. That’s why you resonated with me from the get-go, man — what an amazing path to just engage with these high performers and you get to hear a lot more of their stories. I don’t get to ask a lot of questions, but —
Tim Ferriss: Although you get to have off-the-record conversations about money, and I remember someone said to me, they were like, “If you really want to know somebody, you’ve got to talk to them about their finances and sex.” And they’re like, “You will know everything about that person.”
Andrew Rosener: Yeah, sounds like an idea for a new podcast.
Tim Ferriss: I’m having public conversations. So you get a very different side. You get the behind-the-scenes, which is also super interesting.
Andrew Rosener: Not all the time, but yes. I mean, again, I’m an extremely discreet person. Privacy is kind of like —
Tim Ferriss: It has to be. It has to be a religion for you guys.
So we’re going to wind to a close, get you to dinner with your family, get me to dinner with my team. Is there anything you’d like to say before we close up shop for the day?
Andrew Rosener: Thank you. It was really an honor to sit down with you. I really cherish it. I’ve taken a tremendous amount of wisdom from you and your guests over the years, and so it’s a bit surreal to be sitting on this side of the microphone. But, thank you.
Tim Ferriss: You’re welcome. My pleasure.
Andrew Rosener: Thank you for all that you do, really.
Tim Ferriss: Yeah, thanks man. And I remember since our first meeting, we were talking about these Hokkaido scallops. I was like, “All right, there may be a point in time when we have to have a conversation in front of some mics,” and it happened.
Andrew Rosener: Even when I was young, my sister and I learned Japanese when I was probably between 10 and 13. A couple days a week we went to this woman’s house and she would teach us origami and how to cook and speaking Japanese. But I’ve lost all of it. So I’d be embarrassed to try. I think I can count to eight is about the extent of my Japanese these days.
Tim Ferriss: Well, you have that optionality. So tomorrow you could close up shop and become a Buddhist monk in the mountains of Japan.
Andrew Rosener: That might be next year.
Tim Ferriss: If you wanted, if you wanted. All right. So just to recap where people can find you, mediaoptions.com.
Andrew Rosener: Correct.
Tim Ferriss: The industry’s leading educational podcast, DomainSherpa, which people can find at domainsherpa.com and on Twitter —
Andrew Rosener: Ds.tv will take you to the YouTube channel.
Tim Ferriss: Ds.tv goes to the YouTube channel and @AndrewRosener on Twitter. And we’ll include also additional tenets of Charlie Tuna and so on in the show notes.
Andrew Rosener: Yeah, they are priceless and they should be in time, immemorial.
Tim Ferriss: Yeah. So we will put those as always at tim.blog/podcast and people can find this and to everybody listening, thanks for tuning in.
As always, be a little kinder than necessary to others and to yourself. Until next time, thanks so much for listening to The Tim Ferriss Show.
***
Andrew Rosener: When I said “hunting bigger fish,” I mean it quite literally in the sense that I said before, people were knocking on my door to have me sell their domain names. And now as opposed to trying to go solicit and sell these $5,000 domains, $20,000 domains, $50,000 domains, I said, “I want to go contact the owners of some of these bigger domains and pitch them on having me go sell these domains to an end-user.” And in order to do that, I had to have some semblance of an idea of what I thought their domain is worth. Because whether you’re contacting a buyer or seller, the first question, “What’s the price? What are you going to sell it for? What are you trying to sell it for?” And so —
Tim Ferriss: Scallops, houses, doesn’t matter.
Andrew Rosener: Doesn’t matter. What’s the price? And so I had to do a lot of thinking about what am I going to tell them? And I’m not going to lie, there was a lot of fake it until you make it in the early days.
Tim Ferriss: $1 billion dollars.
Andrew Rosener: A hundred percent.
Tim Ferriss: I have some bad news, Bob. I didn’t get the billion. Here’s the good news.
Andrew Rosener: There’s a certain degree of also telling these people what they wanted to hear because I didn’t have a reputation at that point, or not much of one. I didn’t have a lot to write off.
Tim Ferriss: Bob, you may have heard of pizza.net. All right, sorry. Keep going.
Andrew Rosener: No, no. So the absurdity is not lost. So at that time, well, you’re sort of a soft master of this. In that early 2000s, mid-2000s, SEO was really the name of the game for online marketing. That was where people were really making the real money, and most people were guessing on it. But there was a few good people that really knew how to play the game. And I got very lucky, I’m not going to say his name because he’s one of my favorite people in the world. He’s one of the just truly an amazing, amazing, one of the most humble and just incredibly intelligent, and just by my definition, one of the most successful people I can think of. But he’s very private, so I won’t say his name, but I was lucky enough to get him as a client and he basically said, look — he hired me to actually go buy domains for him as opposed to what I had been doing, which was outbound selling.
And the domains he wanted to buy and the prices he was willing to pay for them were shocking to me and I couldn’t understand it. And I’m a very curious person. And so I was really like — I pride myself, I don’t ask too many questions of my clients. And I think that that’s one of the things that they appreciate. But when the opportunity arises, I try to get into their head and understand how they see these things, particularly as it pertains to domains and other things that are pertinent to me. So I got to understand the way he saw domain names, and I realized that even though he didn’t know it at the time, it was literally the key to creating an objective valuation for any domain name. And I had to tie it back to a way that people in business could understand to create a business case for — because people just flat out reject you because these domains are expensive. And if I’m soliciting them, they weren’t planning to spend this money to buy this domain.
So it’s just very easy to just say no. So I have to have a very compelling business case as to why they should spend this money to buy this domain. And this took quite some time, and I guess this is one of the reasons for my success was again, I’m not afraid to just throw things against the wall. And so I would start formulating these sort of algorithms or too strong of a word and make me sound more clever than I am. But these formulas of how I could think about and how I could demonstrate to somebody what this domain was worth in an objective way. It was based on data that couldn’t be negated. This wasn’t an emotional thing. This wasn’t a intangible thing. It was like, “Look, let’s think about what is the purpose of a domain name.” And the purpose of a domain name is to connect a business or an idea with its intended customer or reader. Many different use cases on the internet. Let’s stick with business for now. So connecting a business, its product and services with an intended customer.
And you can do that with an IP address, which is ultimately what a domain name is masking. Okay, it’s an IP address, but humans aren’t very good at remembering long strings of random numbers. And so that was really the point of creating a domain name. And so if we think about a domain name from that first principle of domains exist because it’s a human, readable format for getting somebody on the internet to a destination, then what are the characteristics of the domain name that might make it more valuable than another one? Okay. And I thought about it from a business perspective.
I said, “Okay, if I’m going to create a startup, I’m looking at it from a perspective of what’s my total addressable market? How big can this business be?” And I believe, it’s my thesis, which has seemingly proven true over hundreds of millions of sales and many years now, is that you can measure the total addressable market. The objective, not necessarily subjective, but the objective addressable market of a domain name can be measured through starting with search volume. So you can go to Google or any of these SEO tools and you can say, “Okay, how many people a month are searching for car insurance?” Just the words: car insurance. And then there’s an associated long tail with that car insurance in Phoenix, Arizona, new car insurance, used car insurance.
Tim Ferriss: Best car insurance.
Andrew Rosener: Best car insurance, right. Car insurance quotes. So there’s a whole long tail associated with that. And each of those long tails is discounted to some extent, but primarily we’re looking at the core exact match search volume for a particular keyword or acronym. And that’s going to give us the total addressable market in the United States, globally, whatever country. You can usually break these things down by country and see where is this market. And then you can see what is that market worth by looking at what are advertisers willing to pay for that keyword. There’s a certain amount of traffic going to Google searching for that. Now, for simplicity’s sake, I’m focusing on Google here because it’s the one that people are going to resonate with the most, but we extrapolated —
Not immediately, but over the years, we’ve extrapolated this out to basically measuring use in culture and use in commerce, which can be measured on social media, which can be measured on YouTube, which can be measured across a whole frame of different metrics. But for the purpose of simplicity, we were measuring how many people are searching Google for this keyword or acronym? What are advertisers willing to pay for that keyword or acronym? And that’s going to give you, just those two numbers alone is going to tell you what’s the total addressable market on a monthly basis for that keyword or acronym objectively. And then you can extrapolate that out by a reasonable business multiple and say, “Okay, well this total market is worth, I don’t know, conservatively, let’s say 36 months.” In some other industries, maybe it’s 60 months. In some other industries, it might be 120 months.
Tim Ferriss: Can you explain that for a second? I’m from Long Island. A little slow on the uptake sometimes. So explain how the time varies.
Andrew Rosener: Okay, so each business or industry —
Tim Ferriss: Or duration, so to speak.
Andrew Rosener: Each business or industry, if you’re looking at M&A, one business is going to buy another business, there’s generally a multiple that these people will pay. In each industry, it varies. And the type of business varies.
Tim Ferriss: I see what you’re saying. So the multiples is dependent on which industry the search term is associated with.
Andrew Rosener: Right. How durable is this business?
Tim Ferriss: I got it, I got it. So if it’s retail versus SaaS versus whatever.
Andrew Rosener: Yeah. If it’s some sort of the hot, new shiny object trend, you’re going to put a pretty low multiple on it. It might be two years, three years. If it’s, I don’t know, cabinets.com, okay. It might be a very long multiple because it’s a very durable industry. It’s not going to be a lot of disruption, and the multiple’s going to generally be a bit higher.
Tim Ferriss: I see. I wasn’t thinking about this correctly. So the durability is a real factor in this particular calculation. It’s not just looking at the industry and what type of acquisition prices —
Andrew Rosener: It’s both.
Tim Ferriss: Right. It’s a combination of those, totally.
Andrew Rosener: And again, this comes back to meeting people where they are. So I generally will not presume, and I’ll ask them, “If you were buying a business in your industry, what’s the multiple you’d be looking to pay?” And that’s the number that I’ll use. And most people are — they know that off the top of their head, like, “Generally, we pay 3X, 5X.” So when I’m doing back of the napkin, I generally use three because I like to just be conservative, and I find that to be the best approach with domain names. Because as you said, most people don’t understand how to value these things. So the more conservative you are, the more you’re going to resonate.
So you multiply that out, you got how many people search per month. Okay, let’s just call it use in commerce and culture. We can measure that. What are people willing to pay for that traffic? We can measure that, multiply those two, and then extrapolate out by the number of months that is appropriate for that industry or business. That’s going to tell you basically, roughly speaking, there’s other variables, but that’s going to tell you your total addressable market.
We’re going to look at click-through rate and conversion rate. And so that’s the next part of the formula is here’s the total addressable market, and here’s the amount of that market I feel like I can realistically capture. And this is where sort of the SEO comes in. So if you are ranking number one in Google for a particular keyword, and it varies based on keyword, and you’re the number one organic listing, meaning you’re not paying Google to be number one, you’re organically ranking, you can reasonably expect somewhere in the 25 percent call. It used to be 28, maybe it’s 23, maybe it’s 18, but it’s 20, 28 percent click-through rate just for being the organic first listing of that.
Okay, so let’s just say roughly speaking, there’s a hundred thousand people a month searching for this keyword. 28 percent of those paid, let’s say 25 free easy numbers because I’m doing public math, which is generally a rule I have against doing, but 25 percent of those people are going to click. So now you’ve got 25 thousand people that are going to come to your website, and how many of those people are you going to reasonably convert? And I like to use two percent. I think it’s generally a conservative e-commerce metric, two to four percent, but let’s say two percent. So you’re going to have about 500 people per month that are converting. And then you multiply that by whatever you would have been. It’s basically the opportunity cost. So what would you have been paying Google to get that? Okay. And that’s going to tell you the cost of customer acquisition to be that number one position in Google.
And then based on a bunch of studies from Microsoft, and we can reference those studies in your show notes if you want, but you can demonstrate what the delta is between having a domain name that clearly — it needs to be one of two things. It needs to be a brand that people trust and/or recognize. Or it needs to have clear intent baked in. So the domain name needs to match the intent of the user. And if you have those two things, you’re going to materially increase — I don’t remember the exact number offhand, but it’s a very material increase in the conversion rate and the click-through rate, both. So using that formula, we can demonstrate very clearly the delta between your cost of customer acquisition on joeysbagofdonuts.com versus donuts.com. You’re going to have the higher click-through rate, which is going to give you the bigger opportunity, and then you’re going to have a higher conversion rate, which is going to obviously grow your business. And so that delta extrapolated out by whatever that reasonable business multiple is the objective value of the domain name. Does that make sense?
Tim Ferriss: It does make sense. I think I’d probably need to see it on paper.
Andrew Rosener: So ultimately, we’re taking it back to that first principle, which is a domain name’ss value is its ability to arbitrage your cost of customer acquisition. If we can reduce your cost of customer acquisition with this domain name, there’s a value. And then you just have to multiply that value out by however long you feel is appropriate for your business to tell you what is this domain name worth to your business. And that is a non-trivial, non-objectionable business case that ultimately is what led to my success in this business was I was able to make a business case and convert people where others failed. Because it was a mathematical valuation methodology that nobody had ever seen before. And you could say, “Look, how can you say no? I’m showing you how I’m going to reduce your cost of customer acquisition, which is one of the most important metrics any business is going to measure. And so if I can do that, how many months multiple are you willing to pay me?”
Tim Ferriss: I guess, the months multiple is where it seems like you could have a disagreement.
Andrew Rosener: Sure, absolutely. And that’s where the disagreement lies. But it certainly doesn’t have a hundred percent hit rate. Most people still have an emotional block to, “I’m not going to pay some domain squatters X amount of money for this domain name.” It’s just an emotional wall. And sometimes I can break through that and sometimes I can’t. Over long periods of time, I’m generally pretty good at converting people. But once it clicks for people that there is a material reduction in the cost of a customer acquisition, I don’t need closed deal on that day. It’s like the movie Inception, the Leonardo DiCaprio movie. Once I’ve planted the seed in your mind, you’re going to go home and you’re going to go to bed, you’re going to have board meetings, you’re going to meet with your founders, you’re going to meet with teams in your company, and at some point it’s going to come up and you’re going to wake up one morning with this moment of inception where you think it’s your idea that you’re going to be able to scale your business in a way that you otherwise wouldn’t be able to.
You’re going to launch a new division, you’re going to start buying paid advertising. Some initiative is going to benefit tremendously by owning this domain name. Maybe a new competitor has launched. Maybe there’s somebody with your brand name in a different industry that you don’t want them to have the domain, but something is going to pop. There’s going to come a moment — which is why domain names are generally a very long sales cycle, but there’s going to be an inception point where you wake up one morning and you think, “Okay, now I need this domain name.” And then you’re going to call me back, or you’re going to send me an email and you’re going to say, “Hey, is that domain still available?” And sometimes it is, sometimes it’s not. Another sort of powerful phrase that we’ve coined is off the market forever. Once these things sell, they’re generally off the market forever.
The moment a company makes a decision to acquire this domain name that they were fighting tooth and nail not to buy previously, it’s basically priceless to them. Because what they then say, which is so interesting to me because they don’t realize it before buying it, is that they then say, “But this is my brand.” And you go, well, “I couldn’t agree more, but then why didn’t you want to buy it in the first place?” But the moment a company buys it, the first thing they’ll tell you is, “This is my brand. I can’t sell it.”
I won’t use this specific example, but we sold the domain. It was quite a good price, but I was fighting tooth and nail. Nobody wanted to buy this domain. It was a very good domain. The price was very good. It was $250,000 for a domain that I would tell you was worth at least double, triple that. And we finally sold it. And immediately, literally 24 hours later, I would say the David versus the Goliath, the David shows up and says, “You know what? I made a mistake. I want to buy it.” And said, “I just sold it.” And so this guy was really, really successful, but he was like a ninja versus a big Goliath. He was like the Charlie Tuna versus the big factory.
But he had a really successful business and he had some money. And he said, “Look, offer them…” I think it was — like the example, I think it was a hundred thousand dollars more. Owner said no. And this guy had just bought it. He hadn’t done a single thing with the domain name. It literally hit his account 24 hours ago. He hasn’t set up an email on it. He hasn’t even redirected the domain name. It’s got a parking page on it, nothing, zero. He just is now the owner. And we went from — he bought it for 250. This guy offered 350. He said no. Went to 500. He said no. Went to 750. He said no. Went to $1 million. He said no. That guy tapped out. And this guy was just like, “I don’t think there’s a price. It would basically be he’d have to buy my whole business for me to sell this domain because this is my brand.”
And it’s a very strange phenomena where people don’t — they don’t make that click before buying the domain. And the moment they own it, they realize how powerful this is for their brand. It’s the most important asset in many cases, not in all cases, but in many cases it’s much more valuable and much more powerful than their trademark itself. Because he who has the dot com, there’s only one. And so Apple wouldn’t be — if it was Applecomputer.com, they couldn’t run around calling themselves Apple because somebody else would own Apple. And they would be Apple because the dot com is ingrained into people’s brains with trillions and trillions and trillions of dollars in advertising since 1985 when the first domain name was registered.
It is just an endless — every sports game has domain names pasted around the arena. Every news channel, you’re getting inundated with dot coms, every big brand that you know, it is just ingrained. It’s assumed. And so if you are anything except your exact brand match dot com, you cannot or should not refer to yourself as your, let’s say, raw brand. If you’re dot net or dot io or dot AI even, I would argue, and you’re not calling yourself — let’s say you’re, I’ll use Dharmesh because he’s a good sport. Dharmesh from HubSpot. He has agent.ai. It’s a new little venture that he’s launched. And you can’t call yourself Agent unless you’ve got agent.com, because —
Tim Ferriss: Why not? Just to —
Andrew Rosener: Because people are going to assume you’re dot com. If you’re agent.ai, then your brand is agent.ai. And if you refer to yourself as anything else, at a minimum, you’re going to lose 10 percent of your traffic. This has been done. The best study is from Overstock. Overstock tried to do a rebrand to o.co. That’s a whole super phenomenal, interesting story that comes back to the one letter dot coms and whatnot. But anyways, they tried to do a rebrand to o.co, and they were obsessed with this, and they’d made an enormous campaign, and they did massive branding, massive advertising to promote this rebrand. And they immediately — I don’t remember, I think it was like six months, maybe less, they immediately pivoted back to overstock.com because what they saw was that they were losing, I think it was 40 percent, it’s like 30 to 40 percent of all their traffic was getting lost.
Tim Ferriss: And why didn’t they just redirect Overstock.com to o.co? Is that a dumb question?
Andrew Rosener: Well, no, the point was that they’re out there advertising themselves as Overstock is now O, but then people type in o.com.
Tim Ferriss: Oh, I see what you’re saying. I see what you mean.
Andrew Rosener: And so then it’s a dead website. So what does that say about your brand. Like, “Oh, I am on a 404 page, or I’m on a dead — this domain doesn’t resolve page.”
This domain doesn’t resolve, so it’s very detrimental to your brand. I think Amazon highlights this best. I don’t know what the increase in conversion rate was, but like just by taking away one step and making the one click purchase had a profound impact on conversion for Amazon.
Tim Ferriss: Say that one more time please.
Andrew Rosener: When Amazon introduced the one click purchasing —
Tim Ferriss: Oh, sure.
Andrew Rosener: — it had a profound impact. I remember at the time they were talking about it like these very small — if you can remove just even very small incremental elements of friction between your customer in their journey to close, every small bit of friction that you can remove you’re materially increasing your conversion rate, and obviously top line and bottom line.
Tim Ferriss: As demonstrated by the number of Amazon boxes that arrive based on my 3:00 AM orders that I think are 100 percent important and critical to my lifestyle. So ultimately that’s what a domain does. That’s why Amazon bought prime.com, because when I use prime.com, like every time I want to watch something on Prime I go to prime.com. I don’t go to Amazon and then click on Prime, and then go to Prime video. Like there’s five steps there. Instead I just hit prime.com.
Tim Ferriss: You know, this is my one opportunity to share I think the only domain trivia that I have with someone who knows domain a thousand times better than I do, and I’m sure you know this already, but do you know which .com forwards to amazon.com that —
Andrew Rosener: I know a lot of them. I sold most of them to them.
Tim Ferriss: Did you sell relentless.com?
Andrew Rosener: No. No Relentless was actually going to be the original name for Amazon. That was Jeff Bezos’ original domain name for the venture actually before pivoting to Amazon. Yeah. But Jeff loves domain names.
Tim Ferriss: I’m sure.
Andrew Rosener: When he was running the company, when he was still CEO, they bought a lot of domain names. We sold them a lot of domain names, and very strategic and very smart, he understood domain names in a very profound way that most other business executives don’t. And I can tell you that with quite a strong basis because I literally have done business with virtually all of them, all of the big companies, and very few understand how a domain name can solve that customer journey the way that Jeff did.
And he utilized a lot of those domains. He was way ahead of the curve. He bought podcast.com, which forwards now to Audible. He bought author.com, prime.com, tube.com.
Tim Ferriss: He’s a smart man.
Andrew Rosener: Yeah. Very. A very smart guy.
Tim Ferriss: Very ahead of the curve.
Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)