On June 20, 2015, I cashed for $2,452, finishing 268 in the WSOP Seniors event. It was my ninth trip to the WSOP and my first cash in the Seniors in nine attempts. Prior to the advent of the mega-entry tournaments (there were over 22,000 entries over four starting days in the 2015 Colossus event), the Seniors event typically attracted one of the largest fields of the 60+ WSOP events, and it continues to usually have the largest field in all tournaments with a single starting day. (There were four “Day 1’s” in the Colossus, three in the Main Event in 2015.) 4,193 players 50 years old and over paid the $1,000 entry fee for the Seniors in 2015. So finishing roughly in the top 6% of players was nice, but not especially rewarding financially.
My visions of going deep in a WSOP event were pretty focused on the Seniors. It tends to be one of the “softer” tournaments in the WSOP series, dominated, even more than the Main Event, by recreational players. And while I was certainly a recreational player, I was a pretty good amateur. But in a tournament where the starting stack is only 5,000 chips (and it was 3,000 before 2015) you definitely need some breaks to progress through day 1 and onto day 2 and day 3. I played two other events in this WSOP—the $1,500 entry “Monster Stack” where I went deep into day 2 but failed to cash and the $1,500 Split Format where I was knocked out in the first level of play. So the last hope for a deep run in 2015 was going to have to be the $10,000 Main Event that would start for me on July 6, Day 1B. In the interim, it was back to my day job.
In 2008, I co-founded Elastic Intelligence, a software startup focused on data access (accessing data from SAAS applications, like salesforce.com and Zendesk for use in reporting and business intelligence). We struggled to grow the company over five years and were starting to get some traction, with about 2,000 customers in 2013 when we were purchased by Intuit. Software startups are a lot like tournament poker. It takes a lot of hard work and some breaks. The variance is huge and, in the end, about 10% cash. Of those who do cash, only a small percentage make any real money. In this case, we were more or less in the min-cash mode. The investors got most of their money back, but the only one who made any money on the deal was the Investment Banker. Kind of like finishing 268 in the Seniors.
While Intuit is based in Mountain View, CA, and I lived in San Francisco, the group that I worked for at Intuit, QuickBase, was based in Cambridge, MA. I ran two technical sales teams, one in Cambridge and the second in Fredericksburg, VA, which was obviously less than ideal for both Intuit and for me, although I did rack up a lot of miles on Virgin America. We talked about relocation, but after 40 years in the Bay Area, it was tough to leave, and the worst winter ever in Cambridge in 2014-2015 reminded me too much of shoveling snow in Chicago. Thus, we never came to terms. So, it was not a total surprise when, on June 25, I was laid off.
Technology is dominated by young people. Not often, even for “senior” roles, do software companies seek to hire people with 30 years of experience and acquired wisdom. And I had spent almost the full 30 years in software doing startups, which is definitely a game that is dominated by young players (OK, also analogous to tournament poker). I was at a loss about what to do with my life. Even with some reasonable savings, I didn’t have enough to retire, certainly not in San Francisco, where a 2-bedroom condo can run $2.5M. And even if a software startup was in the cards, I was not sure I had the heart to do it again. What else could I do? I drove Uber for a day. Made $22. Hmmm, not an ideal plan. Insurance on my cars was about $22/day. I could help my girlfriend, Pascale, build her Pascaline Paris fashion business. I was actually pretty good at selling shoes, and I was helping her with marketing and keeping the books. But the business was in its infancy and barely providing living money for Pascale and her teenage daughter, Eve. While working with Pascale would be something to do with my free time, that did not seem like a near term answer to my financial needs and preparation for retirement.
I was 10 days from returning to Las Vegas to shell out $10,000 (plus expenses) to play a poker tournament. I thought about not going and holding onto the $10K—seemingly the prudent thing to do. But people who love to play poker are not exactly famous for being prudent with their cash. After all, I had played the Main only three times previously and did have one deep run in 2012. I made it almost to the very end of day 4 and finished 285 for a cash of $38,453. Other than a few local wins of around $40K, this would have been my biggest poker cash. However, for one of the few times in my poker career, I had only a small percentage of my action.
In 2012, I played with a group in Palo Alto called VC Poker (now Silicon Valley Poker). Mike Scanlin, who had entrepreneurial and VC background thought that poker would be a good way to connect startups with potential financial backers. And, in fact, some deals were generated by the group. But the focus of the event, played weekly from September to May, was that 1/3 of the prize pool every Tuesday night was set aside to send someone to the WSOP Main Event. In that year, the second season I played with the group, I finished the season first in points and thus had the big stack when we assembled the VC Poker final table in June, which I won. (It was also in 2012 at VC Poker that I first met Amir Lehavot. More on Amir in later articles.) So the group paid my way to Las Vegas and the $10K entry fee, but they also owned a piece of the action. The structure was that the winner owned 20% of himself, and the remaining 80% was divided among the group based on points accumulated during the season. With my extra 5% from points, I owned 25% of my own action.
While it was nice to have about 40 people who had a vested interest and followed my progress through the four days of the Main Event, I couldn’t help thinking it would have been very painful to give up 75% of the winnings if it was more like $380,000 than $38,000. Therefore, in 2012, I swore that I would never again give up any of my action in the Main Event. Consequently, on July 5, I headed back to Las Vegas, unemployed, but putting up the $10,000 to own 100% of my own action.