I’m a risk taker, a competitor, a man of highs and lows who thrives in the extremes. This attitude has served me well in entrepreneurial environments and on the basketball court, as well as when faced with stressful decisions. This attitude prompted me to decide to take this trip in the first place; it led me to Guatemala and Honduras, sent me jumping from The Platform, laid me down to watch the sunrise, and gave me the opportunity to impact the lives of some wonderful, beautiful children.

But this attitude is also why I’ve had a few troubling rounds with the casinos.

Spring break of my freshman year in college, my good friends Dave and Brian convinced me—without much effort—that we should hop across I-90 to spend the weekend at Turning Stone Casino in Verona, New York. Turning Stone is littered with restaurants, an arcade, a confectionery shop, a comedy club, a showroom, a beautiful golf course, and an incredible spa, but these attractions barely entered my mind. Only one thought, one fact, loomed there, casting a delightful shadow over me—Turning Stone is one of the rare casinos in America where you don’t have to be twenty-one to sit down to play blackjack.

The walk inside depressed me. Higher-end gamblers shuffled their chips at tables down in Connecticut at Mohegan Sun or Foxwoods (or smartly avoided casinos altogether), but in this blue-collar country in midstate New York, grizzled, tired machinists, farmers, and repairmen spent their days sweating and their evenings hunched over the roulette table, betting diaper and dinner money on a few flashing revolutions of the wheel. We were sweet-smelling kids with straight teeth, clean Oxfords on our backs, and lots of potential cultivating back at our $40,000-per-year college. I turned to Dave and muttered, in jest, “Ha. If I ever turn into one of these mothers . . . ”

I won a few hundred at the blackjack table the first day, but two hours into our second day, I blew all of my winnings plus the four hundred I had brought. I was playing with five hundred dollars recently milked from an ATM machine that Turning Stone offers “right over there in the corner, baby.” Over the course of the next hour, I let that five hundred slip through my fingers and found myself playing with another five hundred, all of this drawn from another credit card. When Dave and Brian told me that it was about time to wrap up and head home, my spirits called for another trip to the ATM. “Last one,” Dave said with a smirk, as if he had witnessed this type of behavior before. He and Brian nursed bubbly cups of Coke while watching over my shoulder, having retired their own fruitless attempts for the night.

So I played on and lost another five hundred and we stood up to leave. Dave walked in front of me and Brian behind, escorting me out of the casino as though they could foresee another bad decision.

Just as we turned the corner around a row of slot machines, I (no kidding) faked right, cut left, and sprinted back to the ATM, dodging someone’s lovable little old grandma on the way and using her as a screen. Drawing out money with a plastic card and betting with little plastic chips, I lost the sense that this was real money. That I was really gambling myself deeper and deeper into a hole. This wasn’t food money or clothes money or school-supply money or car-repair money; these were abstract funds. And once I was sitting at that table waiting anxiously for the dealer to flip over the next cards, the idea that I had nearly zero control of the game was lost on me. After every loss, I kept telling myself I could beat this game if I played just one more time, just one more hand, just one more ATM withdrawal. I just knew I could. By the time Dave and Brian caught up to me, I had already punched in my PIN and $1000 was flit-flit-flitting its way out of the machine and into my waiting hand. Another grand. This was big money for a kid on scholarship whose account balance had been limited to what few dollars remained from cutting grass last summer.

That first trip to Turning Stone ended just as you’d expect. I lost that last $1,000 and rode home in a car with Dave, Brian, and remorse. In the wake of the flashing lights, electrifying sounds of the cards flicking out across the green table, and the steady hum of chattering voices, everything felt so silent and . . . empty.

Despite all I lost, the lesson didn’t stick, didn’t burrow into me.

I began to conspire against the casinos, develop schemes to get my money back. And then some. Ocean’s Eleven minus ten. Adam versus the Native Americans to avenge his financial Little Bighorn. I knew I was smart. I knew I could out-think the casinos. I could beat the game.

But over the next three years, Brian and Dave and I taking on the world, I lost around $8,000, money I didn’t even have. (As an upperclassmen, I made $224 every two weeks as a resident advisor.) During those three years, I also walked into Citizens Bank to take out a five-figure cash advance on seven credit cards to buy a sure-thing penny stock that went under eight months after I bought it (and recommended it to my friends Brett and Korran). I reasoned that I had worked hard on the basketball court and in the weight room to earn my college tuition with my own sweat and strength, so why not play a little?

Carrying the weight of that kind of debt on my shoulders, I graduated. I kept my shoulders straight as I walked across the platform, but it was all a masquerade. I had fallen into a pit of debt, the kind of debt that offers neither a favorable interest rate nor the opportunity to defer payments until six months after graduation. The kind of debt that holds your diploma hostage. Walking across the stage, all my friends received lovely leather-bound booklets with their diplomas proudly displayed inside; I got a lovely leather-bound booklet with a letter typed in boldface ordering me across campus to pay the $412.38 balance on my account if I ever wanted to see my diploma alive again.

But the worst still lay ahead.

I vowed to stay away from the casinos and clean up the six-foot deep hole that had become my financial life. But it only takes one wad of cash, one gluttonous split-second decision, and one win for it all to slip through your hands. The casinos count on the hope brought out by an encouraging victory once in a while. Three years out of college, after my first book enjoyed a little success, I was debt-free and had $10,000 cash tucked away in my desk. At the time, I flew for free as a wheelchair attendant at Raleigh-Durham Airport. So, lying in bed one night I orchestrated my master plan. I would fly up to Philly the next morning, drive to Atlantic City, double my money or not, and return home.

And it worked. Within thirty minutes, I took Trump Plaza for $10,000 in pink chips, cashed them in, and flew home. It was a great trip. As I soared thousands of miles above the ground, I really felt how high up I was. My cheeks were probably brightly flushed. I’m certain my eyes glittered. I looked around at other passengers and thought it a shame that they couldn’t enjoy life as I was. It’s hard to describe the rush of a moment like that—the way your heart pounds almost painfully against your chest. A good kind of pain. I was on a high; life was good.

Three months later, Justin and Ryan invited me back up to Atlantic City.

This story is gloomily predictable. Justin and Ryan and I reached Atlantic City on a Saturday night, gambled for a while, knocked back some rum and Cokes for a while, and danced for a while, all within reach of a blackjack table. When Ryan and Justin retreated to the room, I lingered at the tables. Hours ticked by in that cavernous room. By six o’clock Sunday morning, my debit card was declining even the smallest withdrawals, and I was on the phone with some lady at Bank of America in Pakistan or India pleading with her that I was the real Adam Shepard and that she should release my funds. She explained repeatedly that she didn’t have the power to do that—no one did on Sunday—so I would have to wait until Monday. I was already down a few grand, plus the few grand they’d allowed me to tug out of the ATM, and I was asking for the rest. But she said I had to wait. So I waited. But not long.

By Monday at 10:30 A.M., my bank account was empty. I had blown the final $9,000 or so in my checking account, in my travel fund, and I was furious at myself—not for losing, but for being such a lazy, irresponsible, greedy piece of shit to sit down like that in the first place.

When I pulled out of the haze—that almost zombielike state of desire for the thrill of the game—when I realized what I’d done, I dropped my head in my hands. I sat on the edge of my chair as the hubbub roared on around me. Dozens, maybe hundreds, more men and women around me were caught up in the thrill of it. While I was just waking up. Waking up to realize what I’d done and what I’d lost.

I called my pops and met with him Tuesday for lunch. I confessed what I’d done. Spilled the truth about everything that had happened over the previous years. He conveyed his disappointment with a few soft words and a furrowed brow that shook me deeper than if he’d screamed obscenities. I’ve rarely responded to his wrath—and he’s rarely offered it—but those couple of times he has shared his disappointment have changed my life.

In one short weekend, I lost two years’ worth of savings, and a year’s worth of opportunities to see the world.

But instead of shriveling up, instead of giving up, I got back to work. I started saving. I never sat down at a table game again, and thanks to a teary-eyed promise to my father, I never will.

And that decision, that promise, put me in a position to be on the dance floor in Honduras with a beautiful girl from across the world.