I had the best possible email on the Internet, and I sold it along with the domain for millions. I was tom@tom.com from 1995 until late 1999. Short, with rhythm and rhyme, and easy to spell. It was like I was a hidden prince who had but to speak his secret name to be trusted in all matters technical.

I’d registered it, back before you could buy domain names but could get them for free if you knew the secret paperwork to fill out. This was the early days of the web. Yahoo was still a page that listed all the web pages of the day, and one of its main competitors was Justin’s Links from the Underground. When Justin tried to register f*ck.com and wasn’t allowed, he documented the secret form. You had to send it to one of the early gurus of the internet, Jon Postel, who from his office in the basement of USC, would approve or deny your new domain as part of his public service to the Internet.

I had originally wanted the email tom@meyer.com, but then I thought to check if tom.com was available, and got shivers when I found out it was. I filled out the form, but was embarrassed to seem like I was wasting Jon Postel’s time for a vanity project, so made it an acronym for a fake company, T Ontological Media. Then followed a couple weeks of me fretting every time I checked my university email that it was going to be denied, and one day got that email approving it. March 13, 1995.

A year or so later, I realized I should have a web site for it, but decided to use it for an art project, a fake company with fake employees where I was just the web master. I paid my friend Kylin to design it. I was part of early 3D on the internet, VRML, and decided the fake business model should be getting people’s avatars to wear branded outfits for advertising placement in cyberspace. It worked well enough that I got random interest from some investors.

Then I worked on making a documentary that aired on PBS about the Y2k bug with my first wife Joss. While making it, I became good friends with Dick Morley, a member of the Automation Hall of Fame for creating the PLC and an angel investor. When I asked him to invest in an idea, he said he’d do something much better than investing in me, he’d give me his time and work with me.

We had ended up with a lot of debt from the production expenses, so thought I’d try to sell the domain. I updated the site to say it was for sale, and tried to reach out to all the famous Toms that I knew. Tom Brokaw, Tom Hanks, Tom Clancy, Tom’s of Maine, but didn’t get any responses. I would have sold it for $5k if anyone had offered that much, but all I got were jokes from kids wanting to buy it for $20.

A year or so later, Internet IPOs were becoming a big thing, and people were realizing domain names like pets.com could lead to a lot of money and hype. People started telling me that my domain was really valuable, but I’d given up on trying to sell it. And I came up with an idea for an mp3 technology that Dick said we should patent, and he said that idea needed the best of the best, so he brought in his old friend Bob Rines – a member of the Inventor’s Hall of Fame, who’d played violin at summer camp with Albert Einstein, was an Emmy-award winning composer, and had taken the most famous picture of the Loch Ness Monster.

In the fall of 1999, I got a random email from an ESL company based in Taiwan saying that they were a non-profit and had developed a character to teach English named Tom, so wanted to buy the domain. I wrote back saying it was a great domain, and in the right hands could be worth millions if not billions of dollars in an IPO. They wrote back within two hours offering to buy it for $400k, which was enough to pay off the video production debts and have enough for a down payment on a house. It was tempting, but I’d seen non-profits in action and realized that there was no way one had decided in two hours to spend that much money. There was something fishy going on. We discussed it with Dick and Bob, and they brought their wives into the phone call, Shirley and Joanne. We all knew something was fishy there, and the wives were among the most intense arguing that we should say no and refuse the deal. We could tell something bigger was in the works.

On Monday I was back at work where I was consulting at a video streaming company. I got a panicked call from Joss that she had been fielding calls all day from different Chinese people trying to get us to sell the domain. Finally she’d received a call from Solina Chau, who informed her that she represented the Hong Kong billionaire Li Ka-Shing, who had decided that he wanted to build an Internet portal and do an IPO. They had started filing all the paperwork with their chosen name, tom.com, and had realized that they needed to buy the domain first. She offered to fly out from Hong Kong and meet with us the next day.

When we gave Bob the update, he said, “What are you doing with the likes of Li Ka-Shing?” It turned out that in addition to his other experiences, Bob had also done his PhD in Taiwan, had helped set up their patent system, and had been nominated as ambassador to Taiwan during the first Bush administration, so he knew China and Chinese culture quite well.

We all decided it was in our best interest to play it cool, and in fact had a meeting with executives in the CTO’s office at Sony in NYC later that week, about the mp3 technology we’d just patented. Bob and Dick were both based in New England, so we extended the trip and offered to meet Solina in Boston.

Bob took the lead on everything, knowing that they would respect his age and his accomplishments. We rented a conference room in a fancy hotel in Boston, he set up Chinese and American flags around the table, and we spent most of the meeting giving demos of our mp3 tech and establishing that we had a very valuable brand and business momentum in tom.com that we would be sacrificing a lot by selling to them.

At the end of the meeting, while we were going to dinner, Bob and Solina spent the whole walk together. When we arrived, he told us that they had agreed on a price of $2.5 million, along with stock options for $2.5 million when they IPOed. Bob had learned to lawyer before word processors and copy-paste, so he drew up the term sheet with a felt-tip pen on a paper napkin over dinner, and we signed it on the spot.

A few months later, it was the hottest IPO ever in Hong Kong, going to 8x on the first day of trading. Li Ka-Shing had been called “Superman” due to his magic touch, and everyone was sure tom.com was going to be the next big Internet company. He hadn’t taken a Western name, and with all the hype, people even started calling him Tom Li. We didn’t manage to sell at the peak, but we did well.

However, Li Ka-Shing didn’t have his magic touch that time, and tom.com never turned into the next big portal. It’s still up, but it’s a ghost of what it wanted to be.

There was a lot about the deal that was pure luck and timing, but I learned three big lessons from this:

1. There is such a thing as luck, but it favors the people who can recognize when it happens.

2. I’ve spent crazy amounts of money and time on projects that ended up going nowhere, but my best deal was infinite profit on something I got for free in grad school. Don’t expect there to be a correlation between your personal investment and what something’s worth.

3. Make sure you have great mentors, because there is no way I could have negotiated that without them. Dick and Bob, and Shirley and Joanne, between them all, turned a good deal into an amazing one.

I have tried to keep the chain alive and pass on the lessons I learned from Bob, Dick, and other great mentors over the years. Reach out if you’d like to discuss your technology or business.

(I had considered throwing tom.to into the deal, but decided to keep it after all. It’s not such a bad domain and tom@tom.to is a pretty good email address.)