Glenn Stearns: The truth about the Undercover Billionaire

Instead of dropping billionaire Glenn Stearns onto a deserted island like we've watched over and over again on Naked and Afraid, Discovery channel abandoned the Undercover Billionaire star in Erie, Pa. In many ways, the city might as well be a tropical jungle or frozen tundra if you're the kind of person who's used to hanging out on a yacht in the Virgin Islands. CBS News once referred to the location as a "sinking ship," and President Donald Trump described the city's backdrop as "rusted-out factories, scattered like tombstones" in his inauguration speech. Nonetheless, this is exactly what Stearns signed up for.

The billionaire, who built an empire in the mortgage-lending industry, hopes to recreate his rags to riches story in Undercover Billionaire — a reality series that premiered in August 2019. Stearns' life exemplifies the anything-is-possible American dream. He managed to rise up out of poverty, contend with becoming a dad as a teenager, and even beat cancer to become one of the world's select billionaires, but can he grow a million-dollar business with just $100, an old truck, and a cellphone to his name? Let's invest a little time discovering the truth about Glenn Sterns.

Glenn Stearns carried a gun at age 5

Glenn Stearns didn't come from money. The billionaire is truly self-made (ahem, Kylie Jenner). His father was a printer and his mother was a grocery store clerk and house cleaner. As a child, the mortgage mogul lived in a low-income apartment complex in the suburbs of Washington D.C. "We had bars on our windows, drugs were sold on street corners, and I wasn't allowed to play outside after dark," he told the Horatio Alger Association

When he was 5 years old, Stearns reportedly found a gun near his home and carried it around for days. Someone once lit the building's laundry room on fire while his 2-year-old sister was inside. "She might have died, but I happened to be there to pull her out, " he told the Horatio Alger Association. "My childhood seemed normal because that was all I knew."

At age 8, Stearns moved to Rockville, Md., where his father purchased a home for a meager $14,000. This felt like a massive achievement at the time, and one that's hard to fathom considering Stearns reportedly took his 193-foot yacht, the Minderella, to St. Barths for a "billionaire superyacht celebration" to ring in 2019.

Glenn Stearns became a father at 14

Glenn Stearns' troubled childhood eventually caught up with him. When he was 14 years old, his 17-year-old girlfriend became pregnant. When the baby arrived, Stearns' mother — who was already struggling to pay bills — quit her job to take care of the child during the day. Stearns' then-girlfriend worked a night shift and brought the little one to her parents' home every night. It was a busy back-and-forth period, and Stearns admitted he didn't feel like much of a father. 

"I felt depressed when this all happened, as if I'd let everyone down. How odd it felt to be more like an older brother than a father to my own daughter," he told the Horatio Alger Association. Stearns picked up a job at the local mall to contribute to the household bills, even though he had to hitchhike both ways because he wasn't old enough to drive. He worked part-time at a restaurant throughout high school and gave his mother most of what he earned. 

Today, the mortgage mogul has settled into fatherhood and his happily married with six children and two grandchildren.

Glenn Stearns' cancer diagnosis inspired Undercover Billionaire

Glenn Stearns is a survivor — not just of teen pregnancy and reality TV – but of a serious health crisis. The mortgage mogul was diagnosed with throat cancer in 2014, but managed to keep his spirits up throughout treatment. According to his friend, Virgin business mogul Richard Branson, Stearns used a Backgammon app on his iPad to gamble with his odds of recovery. "He has been doing this since we met … 'If I win this game, we're going to get married … if I win this game we'll get through this financial crisis, if I win this game I'm going to get through this cancer.' Good news: he wins every time," Branson wrote on his Virgin site.

Stearns is currently in remission but credits cancer with sparking the idea for Undercover Billionaire. According to Business Insider, the billionaire wanted to show his children that it's "never too late to take a chance." He started thinking about the possibility of recreating his success. If he started a brand new business from nothing, would he still be able to come out, at the very least, a millionaire? "I wanted to challenge myself and see if it's possible to really make it again, or was it luck," he told Business Insider. Stearns' reality show idea was picked up by Discovery, who shipped the billionaire off to Erie, Pa. with nothing but $100, an old pickup truck, a cell phone, and a camera crew.

Glenn Stearns owns a Caribbean island with Richard Branson

Considering Glenn Stearns' resume, it makes sense that the billionaire would brush elbows with other billionaires. They need to stick together, right? There aren't even enough of them in existence to fill up a Carnival Cruise, but who needs an all-you-can-eat buffet when you've got a fleet of personal yachts with private chefs? 

Stearns has fostered a close friendship with Virgin business mogul Sir Richard Branson (pictured), whose estimated $4.1 billion net worth makes Stearns' personal fortune look like pennies. These billionaire bros purchased an island and built a resort in the British Virgin Islands. According to The Orange County Register, Stearns invested $17 million into developing Necker Island, which is touted as "one of the world's most exclusive island retreats." The island is also fully committed to sustainability and supporting the local ecosystem and community, reportedly assisting the flamingo population, hiring local staff, and working to rid the island of diesel generators in order to become energy independent. Sounds nice, right?

If you're hoping to stay on Stearns' island, don't get your hopes up. At the time of this writing, it's booked for the entire foreseeable future.

Glenn Stearns already won at reality TV

The early '00s was a defining moment for reality TV, particularly reality TV centered around rich people doing uncomfortable stuff. Paris Hilton and Nicole Richie left the comforts of their trust funds to go work on a farm in The Simple Life. Britain's best exports swapped their mansions for a makeshift jungle hut in I'm a Celebrity … Get Me Out of Here! Remember when Ashton Kutcher made Justin Timberlake cry in an episode of Punk'd, and when the Osbournes, well, were just The Osbournes?

Stearns didn't escape from this era without ending up on a Survivor-style show himself. In 2004, the billionaire appeared on The Real Gilligan's Island alongside his wife, Mindy Burbano. For those who don't remember, this short-lived series saw contestants starring as characters from the sixties sitcom. Of course, Mr. and Mrs. Stearns assumed the role of the Millionaire and his wife, and according to Business Insider, he won the season.

The Undercover Billionaire was an entrepreneur from the start

Glenn Stearns has had an entrepreneurial spirit since he was just a kid. In fact, he entered the workforce after he failed the fourth grade. That's right, he was just 8 years old when he started delivering newspapers for a meager $6 a month. After about two years, the mortgage mogul upgraded to a bigger paper called the Montgomery County Journal. It was there that he fell in love with the hustle and honed in on his skills as a salesman. 

Each work day, he'd get picked up in a van with a bunch of other boys and dropped off at an apartment complex. The clock would start, and Stearns would try to sell a bundle of papers before time was up. "This was probably one learning experience I excelled at," he told the Horatio Alger Association. "I was keen at analyzing the buyer. By the end of the night, I would have 12 to 15 sales, and the [other] guys would have only 2 or 3."

Glenn Stearns is dyslexic

Glenn Stearns was the first person in his family to go to college. He graduated from Towson University with a degree in economics and has since built a billion-dollar empire and become a reality TV star. Despite his successes — and his private island resort — it didn't look like Stearns was going to jump into academia when he was in grade school. According to the Horatio Alger Association, he struggled in the classroom and failed the fourth grade — but it wasn't really his fault. The self-made billionaire had no idea he was suffering from a learning disability. 

Stearns had been diagnosed with dyslexia, which affects between 14.5 million and 43.5 million Americans, but his parents reportedly hit his diagnosis from him. According to LD Online, people with dyslexia struggle to read, write, and spell regardless of their intelligence, but before the disorder was understood, those who suffered from it were often labeled dumb and lazy. Stearns told the Horatio Alger Association that failing fourth grade "humiliated" him, and he graduated from high school in the bottom 10 percent of his class.

Glenn Stearns' family struggled with alcoholism

Glenn Stearns' family didn't just struggle financially. The mortgage mogul admitted that both his mother and father drank heavily when he was growing up. He comes from a long line of alcoholics, and according to the Horatio Alger Association, his grandparents, aunt, uncle, and mother all "died from alcohol-related issues." Stearns even recalled a moment from his childhood when his dad was arrested after a father-son fishing trip. "My dad was drinking heavily that day, and he passed out in the truck," he said. "I helped drive us home and nearly made it, but a block from my house we wrecked the truck. The police came and took my father away. Life is what you see — and that was life."

Stearns' parents divorced when he was 17, but he says that his father considers the split as the wake-up call that "saved his life." When Stearns' mom walked out on the marriage, his dad finally admitted he was an alcoholic, entered recovery, and reportedly hasn't touched a drink since.

Glenn Stearns used to live on a kitchen floor

Glenn Stearns didn't start out in a mansion or on a private island. The star once called a kitchen floor his bedroom. In a move that sounds oh-so-millennial (even though Stearns is a baby boomer), the billionaire moved to California after college and shacked up in a one-bedroom apartment with five other recent graduates. According to his website, he waited tables, slept on the kitchen floor, and eventually landed a job as a loan officer. He reportedly lasted ten months in the role before taking the leap and starting his own business, Stearns Lending, at age 25. (Clearly, this entrepreneur did not spend all his savings on avocado toast.)

According to Discovery, it took about two decades for the mortgage company to hit nearly $1 billion a month in funding — and this was in 2010, after the devastating financial crisis that more or less gutted Wall Street and the mortgage-lending market. By the time Blackstone bought a majority stake in the company, it was pulling $571.7 million in revenue, according to the Orange County Business Journal

Glenn Stearns felt most alive in the midst of struggle

Glenn Stearns is undoubtedly living a life of luxury — the kind where you can snag a $250,000 ticket on a Virgin Galactic flight like it's a cheap go-kart excursion at a local theme park. Despite all the obvious comforts that billions can buy, like a yacht called the Minderella (his wife's name is Mindy), Stearns told Business Insider that his most memorable moments occurred before the fame and fortune, when he was still struggling to build a prosperous future. "I'd never felt more alive than when I was going for it, swinging for the fences," he said.

This realization — in combination with his cancer recovery — prompted him to create Undercover Billionaire. The mortgage mogul wanted to feel the rush of building something from nothing all over again. Yes, this guy is so rich that he pretends to be poor in the way we pretend to have millions by ordering our brunch cocktails with Tito's instead of whatever's in the well.

Glenn Stearns' namesake company went bankrupt

Glenn Stearns rags-to-riches story isn't without its fair share of failures. The billionaire's namesake company, Stearns Lending, filed for Chapter 11 bankruptcy in July 2019 — less than a month before Undercover Billionaire premiered. According to Inman, the company owes money to as many as 299 vendors, including $189 million owed to Wilmington Trust. Stearns' business reportedly reached an agreement with Blackstone to restructure and get its finances back on track. As part of the bankruptcy deal, the private equity behemoth will give Stearns Lending $60 million in new capital and a $35 million bankruptcy loan. In exchange, Blackstone will take over the company's ownership. It previously held a 70 percent stake, according to Business Insider. The deal reportedly allows Stearns to preserve 2,700 jobs.

Despite the bankruptcy and a foray into reality TV, Stearns told Business Insider that he's ready to "take a run at the mortgage banking business again." Only time will tell which venture is easier: diving back into business with a billion dollars under your belt or finding success on Undercover Billionaire with 100 bucks in your pocket.

From breweries to BBQ: Can the Undercover Billionaire still make a buck?

At the start of Undercover Billionaire, Glenn Stearns doesn't even have a place to live. He spends a night in his car that ends with him vomiting out the door during an interview with producers. Needless to say, his business plan was totally up-in-the-air as well. In an interview with Go Erie, the billionaire admitted he originally wanted to jump into the world of craft beer, calling the brewing community a "close-knit group." 

However, after spending some time with local brewers, Stearns realized he had to ditch that idea. It turns out running a brewery is a really difficult labor of love, and there's apparently no get-rich-quick scheme. "These guys are artists. They really are. They know what they're doing and it's a lot more difficult than I imagined," he told Go Erie. "I … realized that was hard and to try to build that kind of business in 90 days, it wasn't gonna happen."

Instead, Stearns launched a restaurant called Underdog BBQ, which currently has an okay rating on Yelp, so you'll have to watch the reality show to find out if Stearns made a million in the series' 90-day time frame.