64 AMERICANWAY
NOVEMBER 1 2008
with $50,000 packed into a pouch that
zippedclosed,beltedaroundmywaist,andfit
insidemypants. I liked towearbaggy shirts
to cover the bulge caused by a combination
of banded$100bills andblack, purple, and
yellow chips from several different casinos
(thesecolorsdenotedenominationsof$100,
$500, and$1,000, respectively).Secure that
mybankrollwasn’tgoinganywhere, I’ddrive
toa tophotel/casino, check intoafine room,
andget ready todomy job.
Back then, for a few years following my
graduation from college,my jobwas count-
ing cards. I played on a blackjack team,
similar to the onedepicted in themovie
21
,
and earned (or sometimes lost) money for
myself aswell as for agroupof investors.
These moneymen, it should be noted,
werefarfromshadygangsterswhobelonged
to some kind of underworld society. Actu-
ally, theywere straitlaced guyswhoworked
in technology, practiced law, ormaintained
small businesses. As should always be the
case with backing gamblers in legal enter-
prises, thiswas completely aboveboard and
in compliance with the law (we paid taxes
and received IRS 1099 forms). The inves-
tors viewedblackjack as a gooduse of their
money. And it
is
when you have a team of
well-trained card counters playing against
the house with a small edge (less than two
percent, but that clearly adds up in light of
how much money gets churned through
many sessions of high-stakesplay).
For a while, blackjack was a great in-
vestment. We had a bankroll in excess of
$500,000, and we split the profits (be-
tweenplayers, investors, andmanagement)
in a fair and equitablemanner. Yeah, itwas
a lot of fun to bet high and play at being a
richkidwhogets compedby casinos, but at
its core, this was all business, just away to
makemoney. Investors received40percent
of our profits. The remainderwent toman-
agers andplayers. During our best quarter,
Iwaspaidupwards of $100perhour.
These days, in a world where corporate
executives bleed cashout of publicly traded
companies, major investment firms sud-
denlygoout of business, andmortgages are
deeply underwater, entrusting your funds
to a person with the ability to win money
fromcasinosorotherplayersstarts tosound
likea fairly legitimatealternativeway to in-
vest. That’s the case among poker players,
and for high-stakes practitioners, splitting
the action serves as ahedge. “When there is
agoodgame that is toobig formybankroll,
I sell off apiece ofmyself,” apro explains to
me. “If I can realisticallywin$200,000but
havea riskof losing$50,000andmybank-
roll can’twithstand it, Ifindabacker.”
Themostoutréexampleofthiscamewhen
a billionaire banker from Texas wanted to
play poker against themost skilled profes-
sionals in theworld. Presentedwith an op-
TherewasaTime inmy life
whena
TripTo lasVegasusuallykickedoff
wiThmydriVingarenTalcarfrom
mccarran inTernaTionalairporTTo
agardenaparTmenT inThesuburbs.
ThaT’swhereamanwe’llcallTeddy
wouldawaiTme. rouTinely, onadesk
inhishomeoffice, ThereresTeda le-
galpad, acalculaTor, andasTrong-
boxfullofcash. Teddywasn’Tmuch
inTosmallTalkandworkedquickly.
wiThinminuTes, i’dbeouTThedoor,
