I’ve loved football (playing and watching) since I’m six years old. Independent of that love, I have loved gambling (on a variety of things) since I’m 16 years old.
In my early 20′s, I briefly combined the two, and made my first series of football bets. It was a disaster, as I won early, raised my bets beyond my means, and crashed and burned.
I learned my lesson at that time (at least temporarily) and gave up football betting for roughly 10 years.
During that 10 year hiatus, I continued to gamble (small amounts) on both horse racing and casinos (mainly craps). I still watched football and still enjoyed it thoroughly. At the time, I was working on Wall Street, and my job consumed me. I was on call 24/7/365, and it wasn”t just a theoretical on call, as I was often woken in the middle of the night, and I worked most weekends (by choice, as much as by necessity).
So, in 1990, when my income was rising reasonably, and I felt that I needed a real hard break from work (at least on occasion), I wandered back into betting on football. I bet on both college and pros, so I was in action every Saturday and Sunday (and many Thursdays and every Monday night, etc.) during the 20+ week season.
There were years when I lost stupid amounts of money. Yes, I could afford it, but it was stupid nonetheless. In 18 years of betting on football, I only made a profit in two of those years. Probably another 10 years, I beat the vig, which is emotionally satisfying, but still an economic problem, sometimes a very large one!
In 2003, Lois and I voluntarily decided to stop charging management fees to the LP’s in our fund. That meant that we had zero income going forward. We have been living off of savings and interest and dividend income since. We continue to work full time, mostly due to our commitment to our investors, but also because we too are large investors in our fund, and if we can continue to sell companies successfully, we’ll at least get a return on our original investment.
What does all of this mean? In 2003, I dramatically cut back on the size of my bets. I found that I enjoyed the thrill or winning and losing just as much. In fact, possibly more, because the losses didn’t really sting, and wins were gratifying on an emotional level. That made me want to cut my bets even further, but I had been betting with the same bookie for all of those years, and they don’t really want teeny tiny action.
So, both for reasons of wanting to cut my bets further, and, to want the ultra-convenience of being able to bet whenever I wanted, in 2005, I switched my betting to the Internet. I loved it! I cut my bets dramatically, and increased my enjoyment and flexibility at the same time. I even turned a profit that year, which added to the enjoyment. I didn’t delude myself that I should now raise the size of my bets, just because I won.
The next year (2006), I lost, but a small amount. However, that was also the year that Congress passed the knucklehead banking laws which made it difficult to move money into these types of sites (including Poker sites, which are not illegal under Federal law!). Right before the 2007 Superbowl, the site I was using (which I really liked, a ton), decided to stop accepting bets from US citizens.
I scrambled to move the remaining balance into another online site. I did, and was able to bet the Superbowl. I lost, but had lots of chances to pull it out until the last drive, so it was exciting.
At the beginning of this season, I decided not to add any money into my account (it was pretty low to begin with). I bet for the first seven weeks. At one point, I doubled the value of my account. Then I hit a bad streak, and lost it all. I never put in any more money, so I haven’t made a single bet on football since October 2007.
Remarkably, I’ve been pretty happy about it. Looking back, I really needed the release from my Wall Street job. If I had money (in particular big money) on a game on the weekend, unless there was a work emergency, I really didn’t care what else was happening in the world, I was glued to the TV (DirecTV that is, where I got every single game, every single weekend!).
While I take my VC responsibilities very seriously, the truth is that at this point in our lives, Lois works much harder than I do (it’s not even close), and I don’t need any artificial distractions to pull me away from work.
I haven’t been to a casino in years. I would enjoy it, but I don’t feel the pull at all. I still play Poker (quite a bit), but I’m actively participating, and I also consistently make money at it, so it doesn’t feel like gambling at all. It’s more like getting paid to play a game you really enjoy.
So, bringing us back full circle to the title of this post, this is the first time in 18 years that I will be watching and enjoying the Superbowl purely as a fan! I won’t be worrying about the point spread, or who won this particular quarter. I won’t worry about the over under (which often made me root against the team that I was betting on, because I didn’t want the score to keep going up).
Who will I be rooting for? 51% of me wants the Patriots to win, for historic reasons as well as that I like their style (in many ways they are one of the few true teams in the NFL, as opposed to a collection of individual stars). 49% of me wants the Giants to win, since they’re a home team, a true underdog with a beleaguered coach, etc.
In other words, I promise to enjoy the game no matter who wins, and even to be happy about it, no matter who wins, though secretly, I’m marginally pulling for the Pats. 
