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5 ways a Discovery Plus series made boomer billionaire relevant to millennials

Updated: Feb 3, 2021

As a millennial, we have been told that we can do anything we put our mind to, but our parents came from the finish your education to get a secure job generation. We’ve never been told how to catch our dreams, we’ve only been told to chase them.

Undercover billionaire isn’t just another piece of entertainment lost in the noise of all other shows for me, personally. It is like taking a crash course on how successful business owners think and how to execute ideas, showing step-by-step how to achieve a dream and what it actually takes to not only achieve that dream but maintain it and scale it.

Why does this matter right now? Clearly, the world had to completely pivot in all of 2020. People have lost their jobs, their motivation, and their hope. If your business was not essential, it most likely went under. Discovery plus deserves a one-handed clap for creating a platform that is doing things differently than any other platforms.

As USA Today notes, Discovery Plus will offer "real-life" content versus original, scripted programs, such as Netflix's "The Queen's Gambit." Think wildlife documentaries, cooking shows, and home renovation programs.

I call this creating “Valuetainment” as my online mentor Patrick Bet-David would say. Valuetainment is the future of consuming content. Millennials like me don’t want to leave a program feeling uninspired. 2020 has shown me that I am wasting way too much of my valuable time on consuming garbage for my mind. If there is anything good that came from a horrific year of isolation, the feeling of hopelessness, and mental health, it is the reality of how precious our time is and we cannot waste one more second on things that do not matter to us.

What is the Discovery Plus show Undercover Billionaire about?

The first season is about a billionaire (Glenn Stearns), leaving his cush lifestyle, yacht, private jet, helicopter, and his family, to get dropped in the small town of Erie, PA. With only 90-days and nothing but 100 bucks in his pocket, a phone with no contacts, and a pickup truck, his mission is to go undercover and build a thriving million-dollar business for a small town in the US. If Glenn did not accomplish building a business with a million dollar valuation, he then would have to invest a million dollars of his own money. I’m not going to spoil it, so you have to watch the show to see his journey.

So here are my 5 reasons that made this boomer billionaire relevant to us millennials.

I truly believe every millennial should at least give the Discovery Plus show Undercover Billionaire with Glenn Stearns a go!

#1 They took away his superpower

The same reason DC fans love Batman more than Superman is that Batman has flaws.

"MILLENNIALS." Unfortunately, being associated with this word comes with a few negative connotations—whether deserved or not. Often, those connotations extend to the way Millennials work. I have to admit, not all millennials are obnoxious and incompetent. That being said, the majority of them are. That is what has stained the name “Millennial” for us. When the older generation thinks of a millennial, it comes with baggage. Rightfully so. The words, lazy, annoying, unproductive, fickle, millennials tend to not conform to the traditional notion that long hours behind a desk makes for a more productive employee. Managers view them as people who expect more than they deserve; society views them as the “me” generation.

So why is taking away a billionaires superpower relevant and connects with us millennials?

You should read that again. If you are a millennial, you’ll understand right away. But I digress. This is important to us because most of us don’t come from money. So unfortunately, we tend to have a bad taste towards millionaires & billionaires due to an identity complex. Most millennials grew up in a broken home, poor, living in some sketchy neighborhoods. Market watch says that adults under 40 have been accumulating less and less wealth over the past 30 years, plummeting from owning 13% of the wealth in 1989 to less than 7% today. So the majority of millennials not only grew up without wealth, we adopted the lack mindset and is evident in the workforce today.

Undercover billionaire took the boss we once had at our terrible office job, the boss that had the power to hire or fire us, the boss that we couldn’t understand how they could run a business, yeah, that boss, well this show took away that superpower which was money and authority. Look, we don’t have a problem with bosses or authority. Millennials tend to have a problem with not being valued and seen as leaders because to be completely honest, we like taking the easy route. Fast. Instant gratification. And desire to become influential overnight. Those were the things we were told we can have growing up. We were born in the “I” & “Me” generation. iPods and Myspace dominated and ignited that culture. The internet boomed and we had to adopt it and find a way to leverage it.

Undercover billionaire made our bosses human again. As a millennial I got to see under the hood and learn how our bosses think. Glenn Stearns instilled hope for me and humanized the executives I once worked under.

#2 Forced him to make people the hero

I’m not going to completely give the show away, but this is important to me as a millennial. Only having $100 in his pocket and no place to sleep, Glenn quickly demonstrated that he had to make friends in a town he’s never been to and not one person knows who he really is. It was fascinating to watch him wrestle with thinking of ways to flip $100 to a million in 90 days. The key was that he absolutely could not do it on his own. He kept repeating that what made him the money that he has today was actually surrounding himself with people who are smarter than him. So he took that mentality and got to work.

Can this nobody with no money actually pull this off? By the second episode I was hooked and fully invested. In fact, my wife and I binged watched the whole season in two nights. Yeah I know, that is so millennial of us. It was a drug. I needed more of it. I was inspired and emotional watching every minute and paused occasionally for bathroom breaks.

As Glenn shared his every strategy and every move, it gave me a clear insight to how billionaires and executives actually think. As a millennial, we are deeply rooted in our belief that passion must drive the ship. If we aren’t doing what we love, might as well not do them at all. We ran into a few passionate business owners that are in the millennial generation age range and they truly exemplified that passion and struggles in their own company and lives. Then this undercover billionaire had the gusto to come into an unfamiliar town and rally these very talented and passionate people around an idea that he wasn’t even passionate about or had any experience in. BBQ & beer.

The lesson I learned from this is that a true leader and entrepreneur can take a vision and communicate that vision to people who are great at what they do and create synergy and care around that to succeed. He could not promise success to these hard working folks, but he did promise that they could build something special. That is all it took. The people then become the heroes who championed the cause. Glenn set goals throughout the journey that the team could realistically achieve and pulled them through it.

#3 Created deep sentiment

I have no idea how impactful watching Glenn lead this dynamic team was for me. The bet was that he could turn $100 to a million in 90 days, but less than halfway through the show it became more than that. As the viewer you wanted to root for the “Underdog”. Every failure, every rejection, every bump along the way created more sentiment as a millennial. I couldn’t help but to start thinking about my failures, my sunken businesses, my lowly lows. I was invested. If Glenn couldn’t make this happen, my inner entrepreneur spirit most likely wouldn’t make it either.

I could pinpoint the exact moment this show turned into a huge investment for me. It was Dawn Van Scoter that changed this show in the best way possible. I connected with her so much due to her passion for creativity and giving everything she had and keeping her word. There are not a lot of people in the world like Dawn. She is a single mother running two businesses. I feel like being a co-parent and running one business is crazy in itself, Dawn really reflected what being a hard working badass mother and business owner truly is. Her commitment to Glenn without a single promise of payment for her time completely resonated with me and created huge sentiment value.

Although Glenn and Dawn’s relationship was rocky throughout the show, it demonstrated Glenn’s ability to lead people to the finish line. Watching Glenn navigate through this was inspiring and very encouraging to me as I look to lead my team and staff here at Executive Brand Growth and my business endeavors. So many lessons learned on this show creating deep sentimental value for viewers like myself.

#4 The Redemption Story

I’ve got to say, through every challenge Glenn Stearns faced throughout this show, each accomplishment was micro redemption stories leading to a big redemption payoff when he reveals who he truly is to the team at the end of the 90 days. Now I don’t want to go full on spoiler, but I do want to say that turning $100 to a million dollars is extremely challenging considering the time he had to hyper prototype his idea and rallying people behind it. Even for a billionaire, the show humanized those struggles and made you want to champion his cause and see the idea succeed. From flipping tires and lighting fires there are multiple redemption stories sprinkled throughout the episodes.

Redemption is the act of being saved according to google. There were many times it would come hell or high water, if one thing falls through in Glenn’s plan the whole house of cards comes crashing down. In every step, there were huge risks and the stakes were high! From relationships to high risk deals, everything was at stake. Throughout the show, you felt that this poor guy Glenn just can’t get a break. You keep wondering, how the heck is he going to pull this off. Then BAM! Redemption. Someone or something would come alongside him and he would be faced with a challenge.

One challenge stuck out to me and was a big take away. This is the only spoiler I will give, so you have been warned! He had flipped a car to put a down payment on a busted house. He had Dawn work her tail off to get this house to a place where his investment would double. When it came down to selling the house he didn’t come close to the number he wanted. What he then said about the situation left a massive impression on me as a business owner. Glenn said, “I need to lose this battle so that I could face winning the war”. That war was the Rib Fest that Glenn and his team had to completely dominate to put their business on the map to create a million dollar valuation.

His leadership decision to sell the house under priced was something that not a lot of people would’ve done. Because of the time sensitivity of accomplishing his goal of getting the money to enter the competition at the Rib Fest and then making enough money at the Rib Fest to finish the business was a testament to his laser focus and his optimism of this team.

#5 Follow up

As a millennial, we hate being fooled. This whole show, although inspiring, could easily be tossed into the “I could care less” pile by simply leaving out this important factor. I call it, “The follow up”. This is an important element to storytelling that sticks. Let me give you a little background to why this is so important to me personally. I grew up in church. You probably already know exactly where I’m going with this. I’ve seen and heard exceptional preachers and pastors telling you how to live your life from the stage. They were inspiring, motivating, even got me to take action. Listen, I love Jesus, I just sometimes can’t take his followers too seriously. Let me tell you why. I would say that more than 80% of pastors and preachers I encountered growing up and even today don’t represent what they say on the platform in their own daily lives.

I know I’m going to get a lot of hate mail for saying that, but you can send those directly to I’m just being honest. Don’t get me wrong, I personally have leaders and pastors in my life I look towards for guidance and mentorship. People who truly exemplify what it means to love God and love people and make a positive difference in the world around me. Okay, now let’s go back to why follow up is important to me as a human being.

The show talked the talk, but does it walk the walk? It got me invested. But what good is that if it didn’t put its money where its figurative mouth is. The beauty of social media is that it’s happening now. I can jump online and see what these people from the show are doing today and what Glenn Stearns is doing currently. So, just like many people who watch their favorite show, I went online and started researching. Okay, I was validating this show. There. I needed to validate and have closure to what I felt watching it. So the first thing I did was follow Glenn’s instagram. Then I followed the instagram of the business he built and scrolled to see how well it is doing. I really wanted to see if this show was the real deal or was it just one of those realities tv shows. You know what I’m talking about. The business is doing very well to my surprise. It is nice to see these familiar faces and bring them to my real life where they are a click away. Then I started following key people that were part of the show and see how their life has changed since. Rj, one of the directors of Glenn’s new business, has been active online and creating a whole social media experience. It is awesome to see him leveraging the show and watch him go after it.

I believe this is why humanizing these billionaires and executives is so crucial in today’s world. I would have never known the true motive behind Glenn and how he built his fortune, nor would I have cared. The importance of storytelling for executives is more important now than it has ever been. The fact that he is providing jobs in this small town and instilling hope by building a foundation for entrepreneurs to receive help just made me a super fan and I want to celebrate and congratulate his success and those who stuck it out with him.

If there is any chance that anyone from the show or even Glenn Stearns reads this, I just want to say a HUGE THANK YOU for personally inspiring me, a minority millennial business owner who has dreams and aspirations to make an impact and live generously. It also wouldn’t be right if I weren’t to thank Discovery Plus for choosing to create shows just like this, about real people, real impact and real opportunities. I am a lifetime subscriber and excited to watch season 2 of Undercover Billionaire.

I hope this read was good to you and that you enjoyed it! Please leave a comment, share, and let me know if you felt the same about Undercover Billionaire!




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