Saturday, September 2nd: Poker-boomers, trust fund babies, and bears -- oh my!

Warning: the following is friggin' long. Make coffee.

I recently finished a book that had long been on my poker reading list: The Professor, the Banker, and the Suicide King. It's the story of Andy Beal, a very wealthy Texas entrepreneur who decided that he wanted to challenge poker professionals to the highest-stakes game ever played. He studied the game with unnerving diligence, and became, even by the professionals' standards, one of the best heads-up limit hold'em players on the planet. He reasoned that although the professionals still had a slight skill edge, he might be able to negate the advantage by raising the game stakes to a magnitude that made even rich poker pros nervous, thereby taking them out of their comfort zone and making them 'play scared.' The pros countered his strategy by pooling their money, thereby spreading the risk more broadly among their team. They played as high as $100,000 / $200,000. I'll give the book an 8/10: a compelling read, and I have plenty more to say about it, but have elected to leave that discussion for another day -- it is nonetheless a reasonable segue into what I initially wanted to write about this time around: a discussion of whether the new breed of young rich internet poker players can fairly be compared to or learn anything from another group of young adults with money: those born into it. This is one of those topics that has been on my mind for the better part of 6 months, but I always seem to have difficulty fully wrapping my mind around it and expressing it with any degree of clarity...but I think I'm ready to address it here, although I suspect that you'll have to put up with some degree of opacity and literary inelegance. Bear with me, though, because I think there's something really interesting herein.

I have alluded here and there in my posts to feeling as though I'm experiencing a completely unique situation in that I have a modest degree of financial independence at a relatively young age while expending what most would consider to be minimal effort (at least compared to the 75-hour work weeks that my college friends who are rising through the investment-banking ranks find themselves putting in for similar remuneration.) Perhaps in catering to my own self-importance, I have cast the life questions I'm working through as these epic "never-before-faced" inquiries into the concurrent benefits and challenges associated with having some degree of financial freedom at a relatively young age. These are indeed uncharted waters for this new generation of rising "poker-boomers" -- a really stupid term I coined to refer to those who have exploited the poker scene for financial gain over the last 5 or so years: they're young, have a ton of money, and (with some exceptions) subscribe to the dubious assumption that 'the good times are here to stay'. But this conception vastly overstates the actual originality of the situation: even though I pitch these as issues that have never been contemplated by previous generations , I think that description seriously exaggerates the originality of the situation faced by msyelf, and other younger guys who have been fortunate enough to share in the spoils of the online poker gravy train. There IS, in fact, another group of people who have faced these issues before us, and who continue to do so, although they may never have sat around a poker table, and I discuss them below. (Sidebar: one of the habits you pick up in law school is finding cases that, while perhaps having a slightly different fact pattern, can nevertheless be cited as 'on point' for a particular issue, and that's the general relation that the example I'm about to cite bears to my own situation...it's not an exact mirror, but it shares certain elements, and is ripe for discussion.)

I have a few (non poker-playing) friends who are, to be blunt, set for life. Their parents are exceedingly wealthy and, while they would never come right out and say this, if they didn't want to work for the rest of their lives, they probably wouldn't have to. Just how much money their families are worth I'm not quite sure, but I don't think a $30 to $40 Million figure would be altogether misplaced. They don't flaunt it, and you probably wouldn't be able to pick out who the rich kids were if they were put in a lineup of 10 people and you got to hang out with them all for a night, but it's certainly no secret among their friends that they come from a lot of money and enjoy all the resulting benefits. I remember that when I showed up at my preppy undergrad university, I was immediately introduced to a whole new stratus of wealth. Although I myself came from an upper-middle class household -- I went to a private boys' high school, and my parents could afford to foot a $100,000 college pricetag -- the kind of wealth I was introduced to exceeded any 'privilege' that I had previously contemplated. Their families had summer/winter houses and lakehouses in Aspen, Palm Beach, Europe, and the Carribean. They skipped around town in Lexuses and BMW's, which were usually the 2nd or 3rd cars that their parents had bought for them in their young lives. I always wanted to ask them how it was that these giant new entertainment systems and wardrobes seemed to magically appear in their dorm rooms every couple months, but why bother: I already knew the answer. Even those whose parents didn't spoil them to such an obscene extent were secure in the knowledge that, one day at least, they'd be in line to inherit tens of millions of dollars.

So these fortunate souls, whether they fully appreciate it or not, come from enough money to provide for not only their futures, but most likley their kids' and grandkids' futures as well. So back to the idea that I introduced earlier: this hypothesis that poker-boomers are facing these completely novel situations in being introduced to living with money at a relatively young age -- but these aren't really new questions at all, now are they? Is there a significant difference between a college student who grew up middle-class and now grosses 6-figures from poker, and the rich kid of the same age who has similar financial independence as a result of his parents' wealth? Can the former learn any lessons about happiness and life enjoyment from the latter? Just like the fresh-faced rookie that picks a locker next to the soon-to-retire legend in the hopes of gleaning some of the knowledge and experience from his prolific career, I wonder whether the new poker-boomer generation can soak up worthwhile lessons from these trust fund beneficiaries who have had years and years of 'practice' dealing with situations that the rest of us are contemplating for the very first time.

So the first question I ask of you: has my poker journey to this point been nothing other than playing "catch-up" to these even more fortunate guys who have known wealth their entire lives. Let me pause for a moment to make sure that I'm not misinterpreted here: I'm not suggesting that your bank account balance is the definitive measure by which to evaluate your life's worth (in fact, if you've read this blog from the beginning, you'll recognize that that idea is completely antithetical to my prevailing philosophy.) Rather, I entertain the preceding question to get to the more important inquiry which asks just what, other than money, I've gotten from my poker experiences thus far. Because there IS something else, there must be...if there weren't, then wouldn't you have to concede that I'd be in exactly the same position as I am now had I simply won a modest-sized lottery, or derived a similar financial windfall from an inheritance or the like? If you conceptualize the benefits of poker as only financial, then I think you'd have a hard time denying the "catching up" hypothesis I offerred above, which I reject as insufficient. No, there is something else that I've picked up along the way; something that won't show up on an accounting ledger, but what? Just what are these ethereal benefits that I have drawn from the past few years of poker? Yes, there's the money, all good and well, and the satisfaction that I get from not feeling beholden to any particular employer, be it a giant law factory or something else, but those are the easy answers, and still don't differentiate poker-boomers from other young people with money, like the trust fund babies I pick on above. Well here are a few of the things I've come up with:

1) I have probably spilt more virtual ink writing about this first one than any other because, well, it's the most salient and interesting to talk about: money management skills. And yes, it is a "skill". I'm reminded here of the oft-heard accounts of Powerball lottery winners who are suddenly $35 Million richer, but find themselves dead-broke 5 years later. "How can that be?" you might ask yourself, as I did the first time I started hearing these stories. "How could a coal miner who had lived a comfortable, albeit humble existence on $30,000/yr possibly blow through nearly 1,200 times his previous salary in just 5 years. It practically defies comprehension. The traditional explanation for these tragedies is given in Robert Kiyosaki's Rich Dad, Poor Dad book series (it was either in those books or The Richest Man in Babylon...I forget which, but read them both, because they're great), and it's that a lot of these people simply never learned how to have money. If you take a guy with poor money management skills, it doesn't matter if you give him $1,000 or $1,000,000 -- it'll all be gone without a lasting trace in short order (says the extreme version of this view.) All that Poker Opportunity Cost stuff I write about isn't just theoretical mumbo-jumbo. It's life management. In many ways, it is life, or at the very least a parable for the value of our short time here on this planet. Individuals born into wealth may know what it's like to be able to buy any trinket they desire, but so very few people will ever be able to say that they know what it's like on both sides of the fence. Was I happy to work 12 hours / week in the campus burger joint for spending money in college or peddling a new energy service door-to-door in high school to annoyed residents, 98% of whom practically slammed the door in my face? Hell no, but they're experiences that I look back on as invaluable in developing my appreciation for what I have now. Listen, I'm not saying I grew up in Cabrini-Green, but I no longer look at my late teens through mid-twenties and contemplate how much better things could have been had I been as financially secure as some of my peers; rather those were fundamentally formative years and I don't think I could possibly have achieved the poker successes I have without an appreciation of what it's like on both sides of the fence.

2) Gratitude: one of the most unexplored, and underappreciated emotions, in my opinion. I have always heard a lot of successful people talk about it: from Oprah to Tony Robbins (a friend of mine took me to one of his seminars a few years ago; pretty cool) to Superbowl MVPs -- and yet I never really "got" what it was they were trying to convey. It's expressed in different terms: sometimes as a feeling of being 'blessed', other times merely 'grateful', 'fortunate', 'lucky', or 'thankful'. It's a sense of humility. A recognition that you're among the most 0.001% fortunate people on the planet. You might think to yourself "yeah, well it's easy to be 'grateful' when you've got fame or fortune", but that's just the rub: this isn't somehow restricted to society's A-list. It's expressed in equal measure by construction men, teachers, heroin addicts, paraplegics, and incarcerated convicts. Isn't it funny how such a motley crew can be united in their appreciation for this emotion, when their lives are as different as you can possibly imagine? Granted, it's probably triggered by different stimuli for each group, but clearly it doesn't depend on any measure of wealth or stature. What is 'gratitude' doing in this list? Well, for the first time in my life, I think I actually "get it." And it's not just a money thing. I find myself walking around actually appreciating my good health, my cohesive and loving family, my supportive friends, the fact that I can play golf on the cliffs overlooking the Pacific while others get dispatched to fight in Iraq with a 1 in 75 chance of returning in a body bag, To give a somewhat silly example, I was walking through a mall the other day, and I thought to myself that I could not think of a single other person in the entire building who I'd rather change places with; I wasn't anywhere close to the wealthiest, smartest, best looking, or most adored individual in there that day, but I was just overcome by a feeling that I was, perhaps for the first time ever, very happy with my lot in life at that particular time. And maybe this has something to do with poker...and maybe it doesn't. But I still felt it belonged in this list, because it's something I'm feeling more and more these days.

3) High-stakes poker, paradoxical though it may seem, has actually lowered my emotional variance in other life domains. The few people who know how high I play usually ask me at some point how I can possibly play my best when there's so much money on the line -- exactly what I used to think, when I'd peer in longingly on the 15/30 game, while I was a 2/4 nit. But just the opposite is true: it's almost pacifying to me, and actually softens my edge. I used to be far more high-strung, walking around with a permanent chip on my shoulder. But when you've dealt with losing 5-figures within an hour or two (an all too regular occurence for me, of late, unfortunately), it's so much easier to keep life's minor annoyances in perspective. When they get your order wrong at a restaurant, fights with your girlfriend, dealing with stupid and/or slow people (what used to drive me up the wall)...none of it really phases me anymore. It's as though I'm on a 24/7 Xanax...but in a good/comfortable way.

4) This one was also pretty big for me, and it ties in to both my poker play, and the work I put into a few affiliate websites. First a very quick story. I had a friend in college who did a 2-year stint at an investment bank after graduation, hated it, and then got a job as an A&R rep for a major music label. His job was to go to 7 to 10 live music shows at seedy New York bars, trying to find and sign undiscovered talent. So his job was to party and schmooze bands (and also do the business thing in a suit when it was called for in the office.) He got paid next to nothing, but I'd never seen him happier in his life. He'd tell me something that I'd heard from a few others from time to time, but never really believed: that he absolutely loved what he did day-in-day-out, and couldn't wait to get to work in the morning. Seemed to me that's what work should feel like, but I'd heard so few people ever gush about their jobs like that, that I wanted to write it off as pure fantasy. Well you know what: I know what he was talking about now. When I took my semester off from law school and worked on my affiliate website(s), I honest-to-God could not WAIT to get up in the morning and start working. And I've felt the same way about playing poker, as I'm sure many of you have. Yes, you could even say I'm passionate about these things, and I've stopped trying to hide it as though it were some sort of deviant lifestyle, even while most of society wants to write it off as just that. I feel as though my eyes have been opened to what work is supposed to feel like. It's kind of like how I went through the first 22 years of my life happily enjoying ice cream, and then I went to Italy and had the authentic gelato there, and had my mind blown. (If you've ever tried it, I know you know what I'm talking about; if you haven't, don't try to imagine it, because you can't.) But here's the most valuable part of the whole thing for me: the take-home benefit wasn't the happiness that I felt playing poker or growing my internet business; rather the real gold nugget was getting to see what was possible. It was knowing that even if you took poker away from me completely, now that I know what it feels like to wake up in the morning excited to get at it -- now that I know that the stories I'd heard about people whose work didn't just get in the way of their enjoying the rest of their lives, but actually was part of that enjoyment weren't just urban legends -- it's just such an empowering feeling. Like I'm in control now. Knowing you don' t have to settle for less. And that's not something you can just get by somebody handing you a plate of money; you've got to learn it for yourself.

You know what I find to be a depressing thought. Consider the following life: Bob goes to college, works for a couple years at an unsatisfying job, goes to law school, goes to work for a law firm for 4 years to pay off his school debts. He's now 32, so he gets married and has a few kids, and finds that to support his family it probably makes most sense to stick around at his law firm where he's now making $250,000 or so per year, which he needs if he's going to foot 3 college tuition bills. Now he's 55, and while he's happy to have a nice house in a nice suburb and well on his way to having enough money to retire, he doesn't understand why he sees a wrinkled shell of his former self looking back at him in the mirror, wondering what happened to all of his idealism and creativity. I'm not crapping on anyone's career choice -- there are actually plenty of people out there for whom what I described above sounds like an absolutley dreamy existence, and practicing law fulfills every one of their intellectual and emotional needs. But this I promise you: the size of that group is dwarfed -- yes, absolutely dwarfed -- by the number of people who don't choose that path, but rather find themselves wandering aimlessly toward it because it's the path of least resistance. The beauty of this journey for me hasn't really been about poker at all...it's been learning to take control of my life. That may sound unbearably self-helpy, but immersed in a discipline like law that turns out so many unhappy practitioners has really driven home just how prevalent career and life dissatisfaction is in our world. I grew to relish the fact that some of my law school peers looked at me like I had 3 heads when I left school -- "What the hell is that kid doing?? Didn't he get the memo that said that we're supposed to do our 6 semesters of law school, and then go out and be important lawyers?? What does he mean you don't have to??"

I had better stop this post here, since it's already way too long and the fact of the matter is that I could probably write an essay-length exposition on each of the numbered points above, but in the interest of time and decency, I will call off the dogs for now. Whew -- well, I take back the caveat that I gave at the outset warning of a disjointed and erratic post...I don't think it came out as garbled as I had feared. In fact, I'm pretty pleased with this entry; it took me the better part of a week to get it all down. Hope it proved worth your time.

Hmmm...this blog has been missing a little flash lately. Too much text, not enough pics. Here's a shot of me climbing the Sydney harbor bridge.