The Secret Playbook Behind Million-Dollar Domain Deals (Sex.com, AI.com & the Future of Domains)

**Junaid Ahmed** (0:00)
Thank you for tuning in to Hacks and Hobbies with your host, Junaid. We're visited by our amazing guests coming from all walks of life, who want to learn their story, their struggles and their journey on how they got to where they are today. So stick around.
Now Jeffrey, you've closed some of the most iconic domain sales in history. What's the real process behind a multi-million dollar domain negotiation that most people never see?

**Jeffrey** (0:31)
I think a lot of people need to understand that a lot of the times, like if I hire a new domain broker who works for me, they talk about, oh, I've only sold $50,000 domain or $100,000 domain. And the thing is, is that when you sell a domain, or even if you're a small business owner looking to spend $5,000, maybe that $5,000 is like $5 million to a company, it's important to them. And a lot of the recipe is the same. It's about talking about the value. It's about talking about what it can do for their business and then going over the terms. Usually, the stress and the stakes get a lot higher, obviously, the bigger the numbers get. And there's a lot more players and lawyers and folks involved in it. And most of the time, just like normal real estate, right? If you're going to go and buy a house for $150,000 or $300,000, it's probably going to be a pretty vanilla basic transaction. But again, you're going to have a purchase and sale agreement. You need to get financing and you go through those steps. If you're going to go buy the Crown Plaza in New York City, it has those steps. But now you also have a lot more lawyers involved and a lot more terms. And so a lot of the times when a bigger name is coming and there's a negotiation, it's not just the price.
There are trademarks potentially that comes with it. A lot of the times those prices aren't paid in cash, it's paid over a period of time, like one, three, five years. Could have stock involved, could have even some other assets involved as well. But getting back to like the basic numbers of it all, again, it goes back to property. sex.com, when I sold it for 13 million, that was during a time when the adult business was still very high paying and wasn't kind of ruined by those tube sites that was giving it away for free. And there was a change in that industry. I don't think you could get 13 million or more for sex.com anymore because the industry is so low. Right? But when I was selling ai.com, that was right before AI really exploded. And it took almost three years to get someone to really understand the value and see what they could do with it before they purchased it.
And I think that's what it really comes down to. Some people say it's what the market's willing to pay, but that's not really true because maybe a domain isn't as liquid as a piece of property.
But in the right market, with the right kind of name, there is a list of very obvious suitors for specific names that will pay large amounts of money. And in those specific markets, it totally makes sense for them to pay millions for it because in very short periods of time, they will get the benefits and then it never stops. Where an advertising campaign fizzles out after you spend all the money, a domain is forever.

**Junaid Ahmed** (3:23)
You're absolutely right. The domains last forever. It becomes your identity. It becomes something that people can remember you by. apple.com, easiest thing that anybody can remember. They even own all of the iphone.com, itunes.com, because they want to bring everybody back to the main thing.
But that's because they built that brand. They built that memory or thing that people remember. But no, sex.com, this is the first time, literally, I've heard of the domain name. Of course, people in that industry would already know. What has been the wildest part of that domain deal that people don't know?

**Jeffrey** (4:04)
Well, when I was given the opportunity to sell the domain, the company that owned it was actually in bankruptcy. And I was given a finite amount of time to sell it. So I got the opportunity to sell it in July, and it needed to be sold by the end of October.

**Junaid Ahmed** (4:21)
Okay.

**Jeffrey** (4:21)
And at that time, domains just didn't sell for that much money. And I really set a goal for myself and just focused all of my time and energy on that. And at the end, there were different suitors that presented themselves. There was multiple conversations, adult-related companies, others trying to enter the adult business. I actually had a colleague that I grew up with, a good friend of mine. He was actually one of the heads of strategy at Pfizer. And at the time, Viagra was going to be coming off patent.