• 23 Business Lessons from Undercover Billionaire

    Episode List on the Discovery Channel


    What You Need to Know About “Undercover Billionaire" May 11, 2022 Heather Reinblatt

    The compelling Discovery Channel show “Undercover Billionaire” tests whether or not the American dream is still alive and well. The reality series follows billionaires as they’re sent to new cities — given a new identity, $100, a car, a tank of gas, and 90 days to start a million-dollar business.

    Season one:

    1. Million Dollar Bet
    2. Start Up or Die Trying
    3. Take the Bull by the Horns
    4. House of Cards
    5. No Pain, No Gain
    6. Exposed
    7. Trial by Fire
    8. Final Reckoning

    Season two:

    1. Three Million Dollar Bet
    2. Hustle Up
    3. Pressure Tests
    4. Fist or Finesse
    5. The Closers
    6. Be Afraid, But Do It Anyway
    7. Turning Points
    8. Cocktail of Chaos
    9. Dumpster Fire
    10. Wake Up Call
    11. The Manifesto
    12. T-Minus 7 Days
    13. Camel Meet Straw
    14. Judgment Day

    What Is “Undercover Billionaire” About?

    The show “Undercover Billionaire” strips successful entrepreneurs of all their resources – including their name and business contacts – and sends them to small cities with just $100 in their pocket and a car. They’re then given 90 days to turn those limited resources into a successful new business. Along the way, they share their wisdom of building and growing a business.

    In season one, Glenn Stearns, owner of the mortgage company Stearns Lending LLC, goes to Erie, Pennsylvania, where he tries to launch a startup company from scratch in three months. He uses the funds to create Underdog BBQ, a barbecue restaurant.

    A special follow-up on Stearns and Underdog BBQ, “Undercover Billionaire: Return to Erie,” aired in August 2020. Discovery continued to follow his work in a new series, “Undercover Billionaire: Comeback City,” which aired on Discovery Plus in 2021.

    Season two of “Undercover Billionaire” took a slightly different format. This season followed three entrepreneurs – Grant Cardone, Monique Idlett-Mosley, and Elaine Culotti – who each went to different cities with limited resources and a goal of building a business with a valuation of $1 million in 90 days.

    Is “Undercover Billionaire” Scripted?

    With such an intriguing concept – billionaires pretending to be poor while starting new businesses with little to no money – some viewers might wonder if “Undercover Billionaire” is fake. The show stretches things a bit but tries to stay true to the premise.

    While none of the stars are actually billionaires, they are quite rich. Glenn Stearns has a net worth of about $500 million. He also filed for bankruptcy just before the show premiered.

    Some social media users in the cities where the show was filmed speculate that some aspects of it are fake. One Reddit user said there are rumors that the building rented by Underdog BBQ in Erie is actually rented by a California company, for instance. However, there isn’t any concrete evidence.

    There’s also been some conversation about whether these already successful and wealthy business people are starting on a level playing field, even with their resources stripped of them. After all, they’re followed by a camera crew wherever they go – their story is that they’re filming a documentary about the American Dream – and people are more likely to work or interact with them if they think there’s a chance they could be on TV.

    About the Stars of “Undercover Billionaire”

    The two seasons of “Undercover Billionaire” have featured four wealthy businesspeople. Learn more about the series’ four stars below:

    About Glenn Stearns

    The founder of Stearns Lending LLC wasn’t only the star of the first season; he’s also the inspiration for “Undercover Billionaire.”

    Stearns has told media outlets, “The people that really knew me, my friends, they all said, ‘Man you’re the luckiest guy in the world,’ knowing I barely graduated high school and college. So, you know, they’re like, ‘You’re not the smartest guy Glenn,’ and I said, ‘I bet I could do it all over again.’”

    He added, “I said, ‘We live in a great country with so much opportunity, I bet you if you strip me of everything, I could do it.’ I said that for years and then Discovery took me up on it and said, ‘OK, if that’s what you think you can do, put your money where your mouth is.’”

    Stearns had a difficult youth. Not only did he struggle with dyslexia, failing the fourth grade and just squeaking by in high school, but he also became a father as a teen. Despite this, he went on to found a successful mortgage lending company.

    On the show, he went to Erie, Pennsylvania, where he used his meager resources to start a barbecue restaurant, Underdog BBQ.

    About Grant Cardone

    This CEO of Cardone Enterprises and Cardone Capital is also a business guru who shares his knowledge as an international motivational speaker, the bestselling author of “The 10X Rule,” and founder of 21 business programs. He also owns and operates seven private companies and a portfolio of properties worth about $3.6 billion.

    During “Undercover Billionaire,” he went to Pueblo, Colorado, where he found a business partner, Matt Smith, who didn’t have any idea who he was. They created a marketing agency, Wake Up Pueblo, that is now worth about $5.5 million.

    About Elaine Culotti

    This self-made millionaire is known as a real estate developer, interior design mogul, builder, and founder of the iconic venue House of Rock. Raised in Europe, she’s been a serial entrepreneur since she was 14 when she began selling antiques and collectibles.

    On the show, she went to Fresno, California, and stepped in to help revive and rebrand a local business, turning the Shepherd’s Inn into a coffee shop, deli, farmer’s market, speakeasy bar, and inn called Shep’s Club.

    About Monique Mosley

    As the founder and managing partner of Reign Venture Capital, Mosley focuses on supporting women and minority-led start-ups. Known as an entertainment powerhouse, she also served as CEO of Mosley Brands and Mosley Music Group.

    In “Undercover Billionaire,” she went to Tacoma, Washington, where she recognized a gap in the market for healthy foods and juices. During the series, she created Rooted Juice Shots.