How'd you get into this? I said yes.

I’m a domain investor. Actually, I invest in a variety of asset classes but it all started with domain names.

Where does this story begin? Looking back, my entrepreneurial journey started in junior high, at A.E. Wright Middle School in Calabasas, California (before Kim and Kanye lived there). I sold See’s Candies and Jolly Ranchers on the bus to school every morning and on the ride home every afternoon. That’s when I first learned the power of arbitrage, “Buy low, sell high.”

While I didn’t go on to become the candy baron of the San Fernando Valley, I did continue to dabble in various side hustles throughout high school, college, and law school.

Then, in the summer of 1996, just as I was graduating from Loyola Law School, without a job or a clue as to what I wanted to do with my life, I reconnected with an old friend. Marty had started investing in domain names – virtual real estate on the internet – and was building a network of online destinations, including LA.com, Hawaii.com, Candy.com, and many more. He asked me to join him as general counsel and strategic advisor, fancy titles for an unpaid position. What I sacrificed in salary, though, I more than made up for with some equity and a whole lot of experience. More importantly, I discovered domain names.

Experience and equity may be priceless, but they don’t pay the bills, or the $180,000 of student loans and credit card debt I graduated with.

So, with that laser-targeted lack of focus or direction, I ventured out into the world.

Quite fittingly, my first “real job” in the “real world” was at a boutique, entrepreneurial law firm in West L.A. I still remember our firm email address, VentureLaw@aol.com. The managing partner and my boss at the firm, Chris, was my first true mentor. He taught me to take risks and reap rewards. Usually when we won, we won big, like the time my $5,000 stock-in-lieu-of-cash turned into six (or maybe even seven) figures. Sometimes when we lost, we lost big, like the time that same stock went from then-life-changing money all the way back down to $30,000, barely making a dent in my debt. My deal with Chris was that I accepted a below-market salary in exchange for the opportunity to participate in his deals – I got in on his action – and I could take on my own clients.

My first client – not the firm’s, but mine – was a domain investor before domain investing was a thing. Jack owned tens of thousands of domain names – vacant virtual lots waiting to be developed, and he was looking for an attorney to handle his negotiations, contracts, and escrows. Our mutual friend Marty connected us. I witnessed first-hand how his business worked. I saw how much revenue he was generating, I saw how and how much he was spending to acquire the domains, and I saw how he looked at value. My entrepreneurial juices revved up like the intoxicating roar of a Ferrari screaming off the line. I was immediately intrigued and soon-after hooked. Like Chris, Jack was generous with his time and even more so with his knowledge. We quickly developed a friendship and he started teaching me how to invest in the asset class that had made him so successful.

Around that same time I met Kevin, the “computer guy” at my law firm. Kevin was a shy, innocent, and introverted kid, a student at UCLA still trying to figure out his place in the world. He’d hang around the office after school to help us with computer issues, networking, and whatever else we needed from a technical perspective. He was also working on his own startup at the time, and we quickly became friends, developing a sort of “big brother, little brother” relationship. Kevin mistakenly believed I had some valuable insights and experience he could learn from, but I am proud to say that I was responsible for several of his “firsts,” including his first drink and his first lap dance. Kevin was never the same after that.

At one point, Jack asked me if I knew anybody who could code. He was looking to develop custom tools to manage his domain portfolio and to help identify new domains to target. I asked Kevin if he was interested in making some extra money coding for Jack. He was and he did. Jack was happy with me and Kevin. Kevin was happy with Jack and me. I was happy with Jack and Kevin. Win win win. Life as it should be.

The tools that Kevin developed for Jack had a lot of potential, far beyond what Jack was using them for. Once Kevin realized this, he approached me about working together to further develop the toolset into a comprehensive domain management platform and monetization service (try saying that five times fast). I was interested, but not yet ready to go all in. Besides my well-known commitment issues, I still had that debt hanging over my head, and I wasn’t sure that this “domain thing” would pay those bills. Thankfully, Kev was still in school and didn’t yet have the overhead that comes with life in the real world. He moved forward with the project and launched TrafficZ, the business that would one day change his (and my) life forever.

The year was now 2003. I was in-house counsel and doing corp dev for a small public company in Beverly Hills. I was making great money, relatively speaking, for a guy with no wife, no kids, and no real priorities other than to figure out which friends I was going to meet up with at which bar to talk to which girls. And that was just Tuesday night. Life was great, but I was going nowhere fast. In addition to my day job, and in between nights out, I was also working on an internet advertising startup with a couple of other great guys I’d met along the way. Ron and Mike were brilliant marketers, wicked smart, and driven like no one else I’d ever met. Our business was growing fast, and the opportunity was tremendous. The only issue (for me) was that I always felt like a bit of an outsider. My two partners had already been working together for more than a decade, and I was the “new guy” in the mix. I think (actually, I know) that always bothered me and prevented me from fully committing (again), but we’ll save that personal insecurity analysis for another day.

Then, one sunny afternoon in early November, everything changed. I was driving northbound on the 405 freeway, heading back from a meeting with Ron and Mike in Marina del Rey, when I got a call from Kev. We talked for a few minutes and I could tell that he wanted to ask me something, but he was just too shy and too uncomfortable to say what was on his mind. After another 10 minutes of superficial bullshit, he finally found the courage to pop the question. No, not that question. He asked me if I wanted to join him in building TrafficZ, the domain monetization platform he’d launched the year prior. “It’s blowing up, bro. I’m killin’ it.” The random side hustle that Kevin had launched in his junior year was growing rapidly and now he needed help to take it to the next level.

I said yes.