Undercover Billionaire Finds the American Dream in a City America Forgot

He’s a billionaire who starred in his own reality show 15 years ago. He thinks anyone can be successful if they bust their ass and have “the right knowledge.” He wants to make America great again.

He’s ... Glenn Stearns?

Believe it, people. Stearns, who took a break from building his financial services empire in 2004 to compete in, and win, The Real Gilligan’s Island — as the Thurston Howell III character, natch — returns to reality TV tonight because he wants all the 9-to-5-ers out there to know that the American dream is still within reach, if you’ll just watch and learn from him.

I know! Enough with these guys, right? Maybe it’s a little harsh but given the times we live in, you just want to hate Glenn Stearns and this show. 

But here’s the deal: You can’t. Undercover Billionaire (10 p.m. ET Tuesdays, Discovery) is a brilliant concept, and Glenn Stearns, who couldn’t be more unlike the reality tycoon-in-chief, is the perfect person to set in the middle of this show.

First, he’s got a hell of a backstory. “I was born to alcoholic parents, diagnosed dyslexic, and failed the fourth grade. I fathered a child at 14 and graduated at the bottom 10 percent of my class.” At some point, though, the inner lion in Stearns woke up. “I saw an opportunity in the loan business and struck out on my own with my own company at 25. I busted my ass to grow that company into one of the largest lenders in the country.”

We can argue how much skin color and gender played in helping Stearns overcome his inauspicious start to life. But this is a television show, not a graduate seminar. And at the heart of Undercover Billionaire is a simple but intriguing question: Can he do it again? 

To find out, the show’s producers have given him $100 and an old Chevy truck, dropped him into a city of their choosing, where he knows no one. His phone is wiped. He can’t call any old associates for help. He can’t tell anyone he meets who he really is. 

And with that, Stearns has 90 days to build a business with at least $1 million of annual revenue, recruiting a team from strangers he meets around town. If he’s not running a million-dollar company by 90 days, he has to inject $1 million of his own fortune.

So on paper, anyway, Undercover Billionaire feels like Undercover Boss meets Shark Tank or The Profit — successful entrepreneur builds his brand while the producers celebrate ordinary hard-workin’ Americans.

Here’s where it gets interesting. Stearns boards a private jet in Miami, where he lives, and when it touches down, he’s in Erie, Pennsylvania. Perfect! Erie is a town that once epitomized the American dream. But as manufacturing jobs left and well-off residents left for warmer climes, Erie turned into a media case study, a city that abandoned its political roots to vote for a reality-show star who promised he’d bring them back.

Like Buffalo or Duluth or any number of Rust Belt towns, though, it’s all how you look at Erie. And if you’re a native, age thirty or so, and enterprising, you’ve probably formed a tribe of hustlers like yourself, who take pride in squeezing a living out of a town others gave up for dead. All Stearns has to do is find one of these tribes, which he does in less than two weeks.

As a reality-TV pro, Stearns understands he’s there to play the game, and he’s all in. With less than $100 in his pocket, he decides to sleep in his truck to save money while scouring Craigslist for side hustles and the rail yards for scrap he can. 

Then he gets sick, because it’s February and he’s sleeping in his truck, so poof goes the wad of cash in the form of a $250 clinic co-pay. If the vomiting had started just a couple of days earlier, it would’ve been game over. As it is, Stearns recovers and graduates to car- and house-flipping as he builds capital for his business. 

Eventually he’s steered to the area’s small business development center. I can attest from personal experience that these places are a gold mine of help when starting a company. Stearns didn’t discover the center, though; the show’s producers arranged his visit. Also, the cameras don’t exactly stay in the background, which might lead viewers to wonder about a Heisenberg effect. From my perspective, there were a few places where the show could have been edited to cast the star in the best possible light — let’s call it apprenticizing — but Undercover Billionaire plays it pretty straight.

And why not? Glenn Stearns doesn’t need polishing. He’s likable and remarkably humble for a CEO, though admittedly that’s a low bar. He knows this is not a game for the young people who are deciding whether to trust this friendly stranger named “Glenn Butler” who claims to have spent 30 years working in industry and now just wants to work for himself.

At show’s end, Stearns is going to reveal his true identity to these people, and then it’s going to turn into a Randy Newman song. To be honest, I’m less interested in the ending than the journey. I was bummed Discovery only had two episodes available because after watching them I was ready to binge the whole thing. 

Above all, I appreciate the spirit of Undercover Billionaire, which ought to be titled Underappreciated America. We’ve driven through a lot of sad old towns and wondered when someone was going to recognize see these places for the hidden gems they are. The people in these towns don’t want government handouts or even media attention. They just want a chance to succeed like nicer, more affluent cities and suburbs. As an argument for what makes America great, you could do worse. A lot worse.

Aaron Barnhart has written about television since 1994, including 15 years as TV critic for the Kansas City Star.