Introduction

The Big Idea

The promise of America as the land of opportunity, as established and modeled by our forefathers, has stalled out for many. Obtaining the American Dream through the Horacio Alger ideal of bootstrapping your way up the class ladder has given way to widespread cynicism, with a large portion of the population looking for answers.

Modern class stagnation and economic immobility have been compounded by example after example of bad behavior by institutions that were once revered by the American public. For their part, businesses aren’t exempt from this phenomenon, and, in fact, they have become a big part of the problem. Decades of greed, broken promises, and self-centeredness have significantly eroded consumer and employee confidence.

Growing tension because of inequality due to race, gender, sexual orientation, and social class is boiling over and putting at risk the future viability of an America that Ronald Reagan envisioned as a “shining city upon a hill whose beacon light guides freedom-loving people everywhere.”

Rather than waiting for politicians to set aside their agendas and special interests or for schools to actually educate our children and young adults, we have another, far superior option. I have long believed that capitalism, and moreover entrepreneurism, is the answer to many of the ills that plague our society. Turning toward entrepreneurism has the full potential to obliterate economic immobility. Entrepreneurism creates jobs. It raises the standard of living—and not just for these enterprising individuals themselves, but for all Americans. Ultimately, entrepreneurism delivers socialist ends through capitalist means, allowing people to be their best, to pursue their passions, and to contribute to the world as God intended.

The real power of entrepreneurism is that it doesn’t discriminate against anyone based on social class. It ignores whether you are black, white, Native American, Hispanic, Asian, Pacific Islander, or “other,” and it doesn’t care whether you are male, female, trans, non-binary, gay, straight, or something else entirely. It has no preference whether you are Christian, Jewish, Muslim, or atheist. And, it doesn’t give a damn about what college you went to or if you didn’t go to college at all. Entrepreneurism is not subjective. It takes grit and rewards talent, effort, and execution indiscriminately, leaving no room for income inequality or glass ceilings.

Sink or Shine is about taking a hard look at some deeply held modern beliefs. It’s about confronting the stubborn, self-defeating behavior that keeps organizations from thriving and constrains our personal effectiveness, leaders, and contributors. American capitalism has the power to transform communities, families, and individuals. Together, we can re-establish America as the grand lighthouse that will lead the way in ushering in a new era of prosperity and American exceptionalism.

An Instinct for Hustle

I’ve been selling things for as long as I can remember. Early on, I got addicted to the “thrill of the kill.” The money wasn’t bad either, but the thrill was unlike anything I’d ever experienced.

My infatuation with the adrenaline rush of someone handing me a stack of money led my nine-year-old self to set up shop outside of my mother’s workplace—American Press in Neptune, New Jersey. I sold off-cuts of paper as pads and split the profits with Bud, the owner. Even at that age, I was unrelenting in my drive for sales. Every passerby was a new opportunity to hone my pitch, and all but a few left with an armful of goods they didn’t know they wanted until they crossed my path.

While I didn’t quite have the same level of ingenuity as the Girl Scout who sold her cookies outside of a marijuana dispensary, I still charmed my way to a rather impressive $127 in just a few short hours. Other businesses followed. I started a snow-removal service, signing my neighbors up for annual snow-removal contracts—my earliest foray into insurance. I formed a golf-ball reclamation and restoration business where I would sneak onto the golf course after-hours and wade through the water traps to collect lost balls. After cleaning, polishing, and sorting them by brand, I sold them back to golfers at a price of four balls for a dollar.

Armed with a basic understanding of supply and demand, I built a candy empire from the back of the school bus, thanks in part to an uncle who worked at Topps Candy Company and gifted me a treasure trove of Bazooka bubblegum. I fortified my supply with later trips to Price Club—the predecessor of Costco and Sam’s Club. I bought sweets in bulk until I got busted for dealing Pixy Stix in the third grade.

I was always “that kid.” I was the kid with the hustle, the kid with the plan. If you’re reading this, it’s likely you were “that kid” too.

It wasn’t until I studied economics in high school that I became interested in the business of business. My teacher at the time was Marty Lefsky, a man with a wardrobe straight from the 1970s and hair sculpted into a helmet that would make Darth Vader jealous. Mr. Lefsky revealed that the “high” of the sale was only part of the story.

Through Keynes, Locke, and Friedman, I learned about the forces of capitalism and Adam Smith’s “Invisible Hand.” I delved deeper into the concepts of supply and demand, of scarcity and opportunity. I discovered that the definition of entrepreneurism was having the ability to recognize opportunities and organize production, and having a willingness to accept risk in pursuit and attainment of a reward. These teachings led to an epiphany.

Though I liked sports, I wasn’t a jock. I got good grades, but I wasn’t a nerd. I smoked pot and loved live music, but I wasn’t a burner. I loved early techno, but I wasn’t a raver. I was an entrepreneur.

This realization put my adolescent identity crisis behind me and allowed me to adjust my focus. By the time I arrived at The George Washington University on an academic scholarship, I was already plotting my next business venture.

Washington, DC was filled with opportunities for students from the local universities to test out the quality of their fake IDs and spend their parents’ money, so I zeroed in on nightclub promotion as my business of choice. My partner, Aaron Sanor, and I negotiated deals with local bars and nightclubs and delved into insurance a second time by accepting the risk associated with guaranteeing a certain level of bar receipts in exchange for the proceeds collected at the door. We hired and managed a team of sales reps who hit the streets with palm cards and flyers to promote our events. We also hired bouncers to provide security and collect cover charges at the front door.

Venues filled, profits soared, and I learned a host of valuable skills firsthand: planning, marketing, advertising, negotiation, risk management, and human resources. I was also en route to a 3.0—but unfortunately, it was my blood alcohol level and not my GPA.

It is probably as cliché for entrepreneurs to have a distaste for formal education as it is for strippers to have daddy issues. My frustration with academia stemmed from a combination of the monotony of classes I knew would have zero relevance to my future and an itching compulsion to take action, to go after whatever was next. It was clear to me that my real-world experience was going to be more valuable than classroom theory. Besides, I wasn’t intellectually stimulated by my biology or calculus classes. There were times I considered dropping out altogether. Instead, I pursued an internship at Smith Barney and then proceeded to convince the gentleman for whom I worked to sponsor me for my Series-7 license. By the time I was nineteen, I was a stockbroker and traded in my club gear for a suit and tie.

It didn’t take me long to begin appreciating success, all the while hearing questions from friends like, “Why are you wasting the best years of your life?” I was confident that this was the road I was meant to take. I was hustling during one of the biggest bull markets in history. I quickly realized that, though I was good at telling stories, the work was rather unfulfilling. I secured client monies and our managers turned little piles of money into bigger piles of money (most of the time). It seemed that no matter how well I did, they were unsatisfied, always wanting more.

Still, despite my age and inexperience, my hustle opened doors. David Morningstar, the same gentleman who gave me a chance as an intern, invited me to join him in starting The Executive Management Group. EMG was going to be a different kind of financial services firm. Rather than selling to mom and pop across the dinner table, we would sell across the boardroom table. We focused on issues that impacted businesses and the employees that worked for them. Rather than telling emotional stories that moved people off the schneid to buy stocks and bonds, we solved problems that plagued entrepreneurs and kept them from...