Inside the mind of 'self-taught' millionaire Shawn Meaike: 'I wasn't trying to live broke'

Serial entrepreneur Shawn Meaike is worth "in excess of nine figures," and credits his success partly to distancing himself from his family’s liberal beliefs after noticing that successful people had a different world view. 

The 51-year-old grew up broke, living in subsidized housing in Connecticut with a dedicated single mother. He respected his mom, but wanted to create a better life than the one she was living. 

"I told my mom one day, I'm like, ‘Mom, I love you with all my heart, but all you've preached to me about is how I have to believe in being a Democrat,’ like, that's how I was raised… and I said, ‘But if all of us in this complex and it’s subsidized housing are all Democrats, we've all been voting that way our entire lives. Why do we all still live here? What is the deal here?’" Meaike told Fox News Digital. 

"I gotta go find other people," he continued. "I wasn't trying to live broke. I wasn't going to go out that way." 

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Now, Meaike hosts the "Close & Conquer" podcast, where he recently hosted an in-depth conversation about the ability to carve out a successful business plan with "Shark Tank" star Barbara Corcoran. He has built fruitful businesses in real estate, waste management and life insurance, exiting them with sales exceeding $100 million. 

But things weren’t always so rosy, and at a young age, Meaike noticed that the successful people in his life, many of them were his youth baseball coaches, were conservatives whose politics didn’t align with his mother’s liberal views. 

"I love my mother and I love what she was doing. I love who she is, but I didn't want to follow that path from a financial standpoint growing up, I didn't want to. And all the men and women I saw that were successful, they didn't have those beliefs," Meaike said. 

"I remember reading about Magic Johnson a long time ago when he was with the Lakers. He would call the people on the court and ask what they did for a living. I was like, ‘I ain't Magic Johnson, but that sounds like that makes a lot of sense,’" he continued. "I found people and I buried myself in learning." 

Meaike went off to college to pursue a degree in business at Eastern Connecticut State University but was irked when he realized his professors didn’t have any personal success in the world of business. After about three months, Meaike says he approached the professor who ran the business department. 

"I said, ‘All these business professors are not businessmen and women. Why should I listen to them?’ She said, ‘You shouldn't,’ which I thought was great advice from her. And she said, ‘If that's important to you, Shawn. Then you need to find a major where the people teaching you are actually in it,’" he said. 

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Meaike, who unloaded trucks for UPS and worked at McDonald's to put himself through college, switched majors and went on to become a social worker, where he spent 14 years working with abused and neglected children at the State Department of Children and Families in Connecticut. With capitalism instilled in him from conservatives, he sought for advice along the way, he started looking for side hustles while staying on as a social worker. 

"I enjoyed advocating for families, and, about six or seven years into my journey there, I was having a hard time maintaining my bills. We had a couple of kids, and I loved my job – didn't love my income. So, I got a real estate license and started buying and selling real estate," he said. 

He eventually went from "buying a couple of properties" to owning "hundreds and hundreds and hundreds of units." His real estate holdings gave him the power to walk away from his gig as a social worker when he felt the time was right to make the life-altering jump. 

"I'd amassed a pretty good real estate portfolio, you know, started making some good money. And the leadership changed at my job at the state of Connecticut, and I didn't like where they were going. I was never going to work in a place where I couldn't protect children. It was policy over common sense, so I quit," he said. "I actually got an insurance license as well." 

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He cashed out on real estate and did "very well," and then started a life insurance company, Family First Life, and a waste management company. He eventually sold both for "more money I thought I'd get in 12 lifetimes," but non-disclosure agreements prevent him from being too specific.  

"Life is really good," he said, noting that he was "self-taught" but with a twist. 

"When I say self-taught, it was, but it was self-taught by good mentorship. Like, I found good people," Meaike said. 

Nowadays, Meaike lives in a water-front home in the posh Florida suburb Boca Raton, a far cry from subsidized housing in Connecticut. He regularly gives keynote speeches to help others achieve similar success, and has built Punch Media LLC, where much of the content is centered on turning other people into millionaires. 

As for his current politics, it’s safe to assume who he’ll vote for in the upcoming presidential election. 

"I don't like to watch Biden talk. I'm uncomfortable. I'm embarrassed as an American, but I'm uncomfortable," Meaike said. 

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