I WON A MERCEDES S550 in a card game on the turn of a single card. My namesake grandfather was a gambler, and I think he would have been proud. You don’t win that kind of car by dealing card hands—at least I don’t. First reason is that I don’t gamble. At all. I don’t play cards, dice, or any Vegas games. No bets by me on horses, dogs, professional sports, or the books, legal or illegal. I rarely even buy a lottery ticket. How does this work, then? How did I win a $85,000+ luxury sedan in a card game? All big gambling wins have a story. It starts simple enough. A client didn’t want to set a bonus in our contract for hitting a performance level. The contract rate was significantly lower than our normal rate. I don’t discount. I don’t do “Prove first and I will pay you later” deals; however, I broke my rules with this client. I liked this client. He was crazy in a good way. Fun, smart, a hustler, good to his word, a risk-taker. I said to him, “I’m going to make the performance number we set in the next ninety days, and you’re going to want more, and then I’m going to hurt you in the next agreement.” He said he understood and away we went. I held all the aces, but he didn’t know that. I had trained the team. We had appointments with seven of the ten biggest prospects in their customer industry at the highest decision-maker level. We had converted the traditional competitor message from cost reduction into revenue generation. The final ace was that I was going on every pitch and closing
sales calls. My grandfather Tom never bet on anything where he was not in some way betting on himself, and I have learned to do the same. After ninety days, I called my client and said, “We have over $100M in contracts when you calculate the value over the next five years.” He said, “Yeah, it’s fantastic!” My response was, “Now I’m gonna hurt ya.” He laughed and said, “Alright, I deserve it, let’s have lunch.” We set the place and time. This is where the card game for the Mercedes begins. I called my brother and told him that I was going to lunch and I did not really know what I was going to ask for or how. He said, “You gotta gamble him. Dice, flip a coin, buy some cards, anything. You’ll figure out the bet. Negotiate, then risk.” Great advice. I bought a deck of cards at Target on the way to lunch and sat down with my client. It was a Friday. A good day for some wine at lunch. We talked about business, politics, sports, weapons, cars… a myriad of things. We had another glass of wine. I told him a story about a company that my brother and I had worked at where I had lost $160M and he called me a dumb shit for not suing the guy. I told him a follow-up story about how my brother had flipped a coin with the CFO for his severance package and won. We had another glass of wine. My client had not yet brought up the reason we were there and neither had I. I have a strategy of not blinking first. Let the weight of the matter hang in the air and cause the other person to finally bring it up. My client said (we are at 2+ hours of lunch and nearing the top of a bottle of wine each, bought one glass at a time), “Well, I guess it’s time you hurt me.” I simply asked the question, “You came here with an idea of what I was going to ask for. You had 10% more than that you were willing to give up and that was your pain threshold. What was that second number?” He gave me the number. “OK, I’ll take that, plus $1 more, and I want that dollar now.” He laughed and pushed the dollar across the table. “You know, you could have asked for more,” he said next. My response was, “Rookies haggle, we’re not talking about woven hats on a beach in Mexico.” He laughed again. His next thought was, “I’ve been thinking about a car competition for the sales people. We’d get a big Charger and put it in the parking lot up
Hig h - s tak e s G am b l i n g
on one of those spinning car show platforms. Get ‘em all fired up.” I said, “Do I get in on that competition?” His retort was, “Your car is a piece of junk. Why does a rock star like you drive that? You should drive a premium car like a BMW 750 or Mercedes S series.” I said, “Let’s put that in the competition, then.” “Alright, that’s yours if you and the team win,” was his response. This dialogue needs to be gotten right: T: Do you believe in balance in the universe? R: What are you talking about? T: Do you believe that when things, energy, circumstances get out of balance, that affects things to the degree that you have to balance them out? R: Yeah, I guess I do. If this is a conversion discussion, we can stop right now. T: No, you and I are working on that, but after four glasses of wine each, that’s just cheating. I think that you want to give me that premium car right now. The universe is out of balance because everything we talked about is for the future; you have not made the past right yet. R: [Laugh] OK, maybe you are right. But I don’t know if I want to give you that car; I think you should earn it. T: Are you a gambler, or a riverboat gambler? R: What’s the difference? T: A gambler is just a math major, no guts or instincts. A riverboat gambler has a knife in his boot, an ace up his sleeve, and will bet everything on the turn of just one card. R: You know I’m a riverboat gambler. T: Then let’s cut a deck of cards and each of us chooses one card. High card wins on just one turn. R: [Laugh] OK, next time we’re together, we’ll get a deck of cards and we’ll do it. T: No worries, I have a fresh deck right here. [I pull out the new deck] We’ll throw away the junk, you shuffle, I’ll cut, we’ll grab but not show, and then we’ll learn whether I own a new car or I have to chase the spinning wheel and I didn’t hurt you on all of the $100M you got so far. H i gh - sta kes Ga mbli ng
R: Is that a new deck? Let me see it. [He tears off the cellophane and checks the seal] Alright. Let’s do it. [He opens the deck, throws away the junk cards, and shuffles for a long, long, long time, then sets the deck down] T: [I cut the deck] You should grab first and not show, then I will. We both grabbed and then showed. He had a seven of clubs and I had a Jack of diamonds. That’s how I won the Mercedes. TIP #1 Gambling is for suckers, unless you’re the house. We all know that
gambling cities like Las Vegas or Macau are not built by gamblers winning. The only way to consistently win in the gambling game is to be the house. That means that the odds are set in your favor before the game is played. The problem with a fair fight is that you have an equal chance of losing. There are no advantages given to gamblers unless you are the house. TIP #2 Don’t play blind. “Information is the key to winning. He or she
who has the most information usually wins.” That includes having enough information not to play. You have to know the game, the players and the risk. In the story above, you can see that I knew all three. That gave me the advantage of not playing blind.
Hig h - s tak e s G am b l i n g