I started taking casino blackjack seriously about ten years ago, and the venue for three-quarters of my gambling junkets has been Foxwoods. Over those years, they’ve been very good to me.

A frequent birthday ritual has been to take the day off and drive down to Connecticut, play some blackjack, and then stop off at Purgatory Chasm on the way home.

The timing of this year’s trip was a little interesting for three reasons. First, it occurred during my last week working at Buildium. Secondly, the remnants of Hurricane Patricia—one of the most powerful storms on record—passed through New England the night before. When I left that morning, the overnight rain clouds were just beginning to break up, promising a beautifully warm and breezy day. And finally, this would be my last trip to Foxwoods before moving away.

Foxwoods chips

Upon arriving, I first went to their Fox Tower casino. I wanted to check it out, because I hadn’t been there since a 2011 loss, back when it was the MGM and brand new. Sadly, all they had were $1 tables, which was an obvious waste of time. So I hoofed it back to my usual haunt at the Grand Pequot.

Once I sat down and started playing, all the chips just got sucked into my gravity well. It took a mere 23 minutes to achieve my predetermined “win” threshold, so I got up, took a deep breath, and cashed out.

It might seem silly to drive four hours and only spend a few minutes at the table, but I don’t go to a casino to play games; I go to win. Winning makes me happy, and you can’t win if you don’t walk away when you’ve won. And if it only takes 20 minutes to achieve my goal, then the sooner I get out of the casino the better! Except, well, I did stop to have a big ice cream before I left…

So that was my last expedition to my favorite casino. They had the most favorable rules I’ve come across, and I’ve only lost on one of my past eight trips, which exceeds all reasonable expectations.

However, that may not be my last opportunity to find a good game of blackjack. There’s a casino right in Pittsburgh, and their state law mandates rules that are even slightly better than Foxwoods’, who annoyingly started hitting soft 17 a couple years back. So we’ll just have to test whether the Pennsylvania government are going to be as generous to me as the Mashantucket Pequots of Connecticut!

Of course, since I was in the area, a stop at Purgatory Chasm was also required. It’s always an amazing, fun, breathtaking, spiritual place, which inevitably provides a dramatic juxtaposition with the overstimulation and consumerism of the casino. The warm weather was a special blessing on what will probably be my last visit there, as well.

And because I was in a self-indulgent birthday mood—and because it was National Cat Day—on the way home I stopped by Boston’s Angell pet adoption center and socialized a few cats, just for fun. It’s been just over a year since I lost Grady, and there’s been a lamentable lack of feline presence in the house.

So overall it was a good day, even though it was the last time for this particular set of rituals.

So whenever the topic of stock options comes up, I have this dilemma. When people learn that I sold my stock near the peak of Sapient's stock value, the usual response is "Boy, that sure was smart. I wish I'd been that smart."

Now, I'm torn about how to respond. Yeah, it was smart. Not that wisdom is the only factor that applied, and not that I can just say to my peers that their financial ruin is a very regrettable result of their lack of foresight. So instead, I usually say that a lot of it was luck, in that I was looking for a house at the time, and sold my stock in order to put as much down as possible.

But not wanting to brag about my wisdom is really just a social phenomenon, which I can put aside in this relatively private journal. Sure, there was a lot of good fortune involved in getting hired at Sapient before its IPO, but I made a number of decisions involved in managing and protecting that good fortune that demonstrated wisdom, foresight, and yes, intelligence. In order to support this conclusion that I'm so averse to admitting even to myself, I'd like to take a look at those decisions.

First, I had a strategy to my accumulation of Sapient stock. I exercised my stock gradually, doing my best to specifically minimize my AMT burden. I also held my stock as long as I could, so that I would avoid increased taxes on short-term gains. And I consulted an accounting firm in order to get the best advice I could on managing my growing assets and minimizing taxes.

Second, I made the decision to sell. Looking at my net worth as the millenium approached, I realized that 98 percent of my fortune was tied up in Sapient stock. No matter how well your company might be doing, that's just stupid. Although my stock had appreciated to an astonishing degree, it was still an unrealized gain that was entirely at risk, and a very high risk at that. I made the decision to sell and put my assets into a condo about a year before I actually sold my stock. At that time, I predicted that the speculative Internet bubble would undergo a whiplash negative counterreaction, as just about anything which becomes such a major trend inevitably does. I sold my stock in the autumn of 2000, a couple months before Sapient's competitors all began dropping like flies. I'm surprised that I looked at places for a whole year before I sold my stock; why my peers completely ignored the all-too-obvious warning signs just amazes me.

And finally, I didn't waver from the thinking behind my decision. A number of people pointed out home financing alternatives that might have been attractive in other circumstances. For example, I surprised many people by offering a down payment of more than two-thirds of the purchase price of my unit, when I could have put nothing down and kept my stock (and also paid a lot more in mortgage interest). Similarly, I was offered a stock-backed mortgage, where my stock would have served as collateral for my loan, and I would have been able to retain ownership of my stock. Either of those options would have had tragic consequences, and I didn't avail myself of them becuase they violated my primary reason for buying a house: cashing out of my risky Sapient holdings.

So although there definitely was some luck involved in my joining Sapient and in the tactical timing of my sale, I think I should be able to gracefully acknowledge that I demonstrated wisdom, foresight, and intelligence in how I managed my financial assets. The fact that I'm so well off now isn't just the result of dumb luck, when the majority of my peers have watched their fortunes be destroyed, and in some cases owe fortunes that they don't have to the IRS.

I don't want to overgeneralize, but I think too many of my peers are whiny, priviledged kids who have never had to learn financial discipline, responsibility, and independence. If you want to avoid a hand-to-mouth existence, have a retirement, and live well, you need to respect your money and where it comes from, and learn how to protect it. That's the wisdom that I have which produced, for me, such a better outcome than my peers.

Of course, that doesn't mean I'm going to lord it over them when the topic comes up; I'll still be careful to avoid any implication that my friends' financial woes are the result of their own shortsightedness. But I needed to write this journal to clarify to myself exactly what degree of conscious control I had over the outcome, and by implication, whether I really was being smarter than most of my friends or not.

Frequent topics