I heard about Planet Poker very shortly after it launched from Rod Peate, who was a shift manager at Hollywood Park at the time. Rod was a pretty savvy poker guy - his claim to fame was finishing second to Tom McEvoy in the 1983 World Series of Poker, and he won a bracelet in 1995. One day in mid-1998 he came into the top section at Hollywood Park sporting a $400 check that he'd just received from his winnings playing $3-6 limit hold 'em on Planet Poker.
The idea got my attention right away - while I loved playing poker, and was doing well at it, actually going out to play wasn't all that much fun. Hollywood Park was a reasonable 25 minute drive from my house; there were better games at the Commerce and the Bicycle Club, but they were close to an hour away. Hollywood Park was in a dodgy neighborhood at the south edge of Inglewood, less than four miles from the infamous Florence and Normandie intersection, the epicenter of the 1992 Los Angeles riots.
A few days after Rod reverently showed us his check, I deposited $100 on Planet Poker and played my very first hand. Ten minutes later, having lost my online bankroll, I started down the same mental path that millions would take during the next few years - trying to work out exactly how I had been cheated. I was a good poker player, was posting regular wins at Hollywood Park, and there was just no way I had lost $100 playing $3-6 that quickly. I decided that I had been playing against one guy, with eight computers, who had been sitting at the table waiting for the next fish to come along. That was almost the end of my online poker career - it was almost three more years before I played another hand of online poker.
In early 1999, I met Sharon, who is now my wife of eleven years, playing cribbage online (more on that here, if you're interested). We met in person a few months later, and started a two year long-distance relationship, commuting almost monthly between Redondo Beach (my home) and Philadelphia (hers). In early 2001, Sharon moved in with me in Redondo Beach. I had taught her how to play poker a year before, and we started playing for very small stakes in some of the LA card rooms. Not long after, we decided to give online poker another try.
At first, our experience was not all that different from my first debacle at Planet Poker. We played mostly on Paradise Poker in very low stakes Sit & Go tournaments ($5 and $10). We were both working regular jobs at the time, and were struggling. We finally ran our combined bankrolls down to $8, and decided that we'd had enough. We made a deal - we'd play Sit & Go tournaments together, on one account (mine - I had the $8), and if we lost the $8, we'd be done with online poker.
Fortunately not just for our bankroll but for my career, we had a huge turnaround starting that very day. We played in $1 tournaments, then $2, then back to $5, and then bigger. Over the next year, we would build that $8 into a poker bankroll that allowed us both to play considerably larger tournaments. Any time our combined bankrolls exceeded $600, we would withdraw $400 and play the rest. By the time we withdrew the last of our bankrolls at Paradise Poker, we had built a poker bankroll of close to $11,000.
A few years earlier, I had met a guy named Steve Badger while playing in some small tournaments at the Crystal Park poker room. (You may recall my mentioning Steve before - he introduced me to the infamous Armadillo Tim.) Steve was a smart guy and an up-and-coming poker player at the time - in fact, he won a WSOP bracelet in Omaha High Low in 1999. Back in the Crystal Park days, Steve and I would occasionally take pieces of one another in tournaments (exchanging percentages of anything we won), and spent a lot of time talking about computers and the Internet.
In August of 2001, Steve called me. I hadn't heard from him in several years. I knew he was still playing - I occasionally saw his name in Card Player and elsewhere - but we no longer traveled in the same circles. He was doing some consulting with a company that was launching an online poker site specializing in tournament poker, and wanted to know if I was interested in helping them test the software. It was free, and they were awarding $250 or so in prize money in each tournament they ran, one per day. I was interested, and Steve arranged for both Sharon and me to play. The company had what I considered a pretty terrible name, which should cement my reputation as a brilliant marketing mind. The company was called PokerStars.
In early September, PokerStars ran tournament #1, although if you were to look it up in the PokerStars database it would actually have a number around #42 - they had conducted a few internal tournaments before opening it up to beta testers. I'm proud to say that I won the very first tournament on PokerStars. I'm embarrassed to say that it wasn't actually me playing. I don't recall why at the moment, but I was unable to play. Sharon hadn't set up her account yet, so she played my account, I think I won $50 - if one of my former colleagues is reading this, please feel free to fill in the correct amount. I played under the name smalltalkdan.
In another embarrassing revelation, I'll now admit that Sharon won tournament #2, but on that particular night, Sharon in fact had a girls' night scheduled. She suggested that I return the favor and play her account. I did, and I won. I have never quite decided if this vindicated me for the prior night or just compounded the evil we had wrought.
Over the next few months, we played quite a few tournaments on PokerStars, and suggested many changes and improvements that persist in the product today. We had both been beta testers for a number of software products in the past, and knew our way around. At the end of December 2001, PokerStars ran a big "tester appreciation" tournament - I think it was $25,000 - which Sharon and I played from a hotel room in Las Vegas. We didn't cash, but we had each built bankrolls of $500 or so and were excited for PokerStars to go live for real money, which happened only days later.
Just after New Year's 2002, Steve Badger called me again. PokerStars had launched, and suddenly they needed a marketing guy. Back then, PokerStars had what became a legendary policy - if you wanted to work there, you had to be a poker player. It didn't matter what your actual job was - this was PokerStars' way of ensuring that poker was in the company's DNA. It was a brilliant, risky strategy that I'm convinced was a key factor in their early success.
At the time, I had a pretty interesting job as Director of Marketing for one of the original shopping comparison sites, PriceGrabber.com. I was comfortable, if not happy, there, and PriceGrabber offered the added benefit of allowing me to work with my daughter Bree for the first time. The idea of leaving a comfortable and very visible job at an up-and-coming company for an online poker startup was scary and exciting and fun. Truth was, I loved the idea, but I made an effort to look at it as though I were a reasonable adult.
Sharon and I sat down to discuss whether I should take the interview. I expected some pushback - seriously, I was going to leave a solid job for a completely unknown quantity, working remotely for people I'd never met? But as she has done so often over the years, Sharon surprised me with her reaction. "You are out of your f***ing mind if you don't at least talk to them," she said.
And that line launched my career at PokerStars.
NEXT: The longest interview ever