Prologue

“Dearly beloved, we are gathered here today to get through this thing we called life.”

— Prince

I made a bad decision. I guess that’s true of most people who find themselves being escorted by three stone-faced TSA agents past curious tourists and business travelers to an inner-airport interrogation room. Unlike most other detainees in that situation, though, I wasn’t full of fear. Sure, I was a bit anxious. You bet I was. Being held for questioning in airport jail isn’t great for the blood pressure, even when you know your release is just a matter of time. I did have one regret, how-ever. One that was bothering me at that moment, anyway. It was my attempt to pass two backpacks stuffed with more than $150,000 in soaking-wet cash through a security point X-ray machine at the Fort Lauderdale International Airport on its busiest day of the year. I had no regrets about how I collected that cash, though. Quite the opposite.

Naturally, the South Florida TSA guys figured I was part of some cocaine-trafficking ring or maybe worse. Why else would I be attempting to board a plane with one of the most wanted terrorists in the world? I wasn’t, of course, but my co-worker (who had been helping me lug the cash-packed backpacks through the airport) shared the same name as one.

“Why are you carrying so much cash?” the agents demand-ed. And “why is it wet?” They assumed it must have been tossed in the ocean by drug smugglers or some other nefarious non-sense. The truth was much cooler. Why was it wet? Rain. Purple Rain. Let me explain.

I’m the founder of Rocket Man Inc., a company which for the previous 10 years had specialized in managing walking vendors (a.k.a. “beer hawkers”) at major sports and entertainment venues and events. The night before, on February 6, 2007, Rocket Man had reached the Super Bowl of the foodservice concessions industry, which just so happened to be the actual Super Bowl. It was Super Bowl XLI to be exact, a showdown at Dolphins’ Stadium in Miami between the Chicago Bears and the Indianapolis Colts. Prince, the legendary pop star and musical virtuoso, headlined what many consider to be the greatest halftime show in the history of America’s premiere sporting event. It sure as hell felt like it at the time.

The Colts were my favorite NFL team—the RCA Dome in Indianapolis had been Rocket Man’s first NFL contract back in 1997, and I hadn’t missed a Colts home game in the 10 years since we secured the momentous deal. For the Colts and Rocket Man to make the Super Bowl in the same year felt serendipitous.

From the start of the event, I was filled with a deep sense of accomplishment and gratitude. I could feel my heart swell with a mix of joy and pride as Billy Joel belted out the National Anthem. By the time Prince took the stage with the Colts up 16 to 14, I was elated. The pop icon opened with a crowd-rousing rendition of Queen’s “We Will Rock You.” It was thrilling. The opening line of his second song (“Let’s Go Crazy”) gave me goosebumps.

When Prince announced: “Dearly beloved, we are gathered here today to get through this thing we call life” I choked up. Rocket Man had been such a big part of my life, both professionally and personally. I had risked and sacrificed so much for the company. I had faced many difficulties, doubts, and challenges. Yet I’d persevered. I’d been able to “get through this thing we call life,” and was still going. Minutes later, as Prince sang “Purple Rain,” the sky opened, and torrential rain poured over the crowded stadium on cue as if the heavens themselves were part of the act. It was magical.

The magic of the moment, however, was lost to the TSA agents. Eventually, after reviewing our laminated Super Bowl credentials with photo ID and paperwork from the event, they realized I was telling the truth. Our team of walking vendors from across the United States had sold tens of thousands of beers at outrageous prices during the wettest Super Bowl in history, all of which was paid for in cash. That’s why I had so much money, and why it was all soaking wet. They no longer suspected I was a money launderer, drug smuggler, or terrorist. They just thought I was an idiot.

From the outside, the actions of an entrepreneur can seem ill advised. Sometimes, however, a better choice just isn’t viable. This case is a perfect example. Normally after an event, my team would run the money we collected through an automatic cash counter. However, the wet bills kept sticking together, so we had to count each one by hand, a process that took until 2:30 a.m. to complete. Once we had calculated sales and settled with our client, I had two choices: take our cut (percentage of sales) in the form of a check, which could take weeks, or bring the cash home with me. I chose the latter.

To wait for a check to come in the mail would’ve been the practical (or some would say “smart”) thing to do, but I just didn’t want to wait. Besides, carrying the cash didn’t seem that risky. I’m a big guy and I didn’t look like I would have anything on me worth stealing. From appearances, my associate and I looked like a couple of average Joes. Nearly every other passenger on the shuttle bus from the stadium to nearby Calder Racetrack—where we as workers had parked our rental car—was also wearing a backpack or carrying a duffle bag. There was no reason to think our bags were any more valuable than anyone else’s. If it wasn’t for those suspicious security screeners at the airport, our trip home to Kentucky would have been uneventful.

If the TSA officers were incredulous, you should’ve seen the cashiers at The Bank Oldham County. Once safely back home, we spread the wet cash across the floors of our office in hopes of drying it out, but to the chagrin of the bank tellers, the bills were still pretty damp when we deposited them. Altogether, the moist currency weighed about 35 pounds. The bank’s president, who I ran into at a luncheon the following week, openly questioned my sanity. He wasn’t the first or the last to do so, but that’s okay. It goes with the territory. You have to be a little crazy to be an entrepreneur. I certainly was. Totally sane and rational people aren’t willing to do such outrageous things in order to survive or take the necessary chances to launch a business. As the founder of several startups, I had done things much riskier than schlep backpacks stuffed with cash through a crowded airport. I’ve also done more humiliating things than being paraded through the airport by armed security guards. Honestly, even being detained and harassed by the TSA didn’t rattle me that much. I’d been through much worse in terms of risk, stress, and uncertainty. I’m a serial entrepreneur. Stress and uncertainty are like sore muscles for an athlete. They’re simply the price you pay to play the game.