Jerry McTear has been entrepreneurial virtually his entire life. “Even when I had a regular job, I always had something on the side,” he says. He started with caddying as a teenager—“I was my own independent contractor”—then went on to clean office buildings in high school and college. “That was my first time owning an actual company,” he says. But even then he made sure to have a corporate job, too. “I was flipping burgers at Roy Rogers at the same time,” he says.
McTear would adhere to this policy for most of his life: working a corporate job for the steady paycheck and benefits while running his own side hustle. Having his own entrepreneurial gig was about more than making extra income, he said, though the money certainly helped. “The money’s great,” he says. “It has to be, or no one would do it. But for me it was always about the reward of being successful independent of others. When you’re working your regular nine-to-five job, you’re really following somebody else’s lead. And your success—while partially related to what you’re doing—is more related to the leadership in that company. When you’re an entrepreneur, it’s all sink or swim. That’s what attracts me, more than the money.”
Still, he believes keeping a steady gig is important, and he recommended that other entrepreneurs do the same. “I know they tell you to pay yourself first,” he says, “but I don’t subscribe to that. In my businesses, I’m the last to get paid.”
That’s why McTear worked a steady job for most of his career. “We were raising three kids, and I needed the steady paycheck and the health insurance,” he says. “As my kids got older and graduated college, that need for a steady paycheck lessened. That’s when I made the transition from side hustle to main hustle.”
McTear retired as chief operating officer and executive vice president of a bank in Pennsylvania before he moved to Southwest Florida. Then he made the switch to full-time entrepreneurship.
He started with a property management company, which he built and then sold. After selling the company to a competitor, McTear decided it was time to retire again—this time for real. “That lasted about a week,” he says, laughing. He started looking for another opportunity, and a broker introduced him to SWFL-based Coastal Carts. “I was looking for something where people would be happy to be spending money,” he says. “Down here, this is paradise. I wanted to be doing something I could enjoy and working with people who would be happy. I saw golf carts and I thought, ‘Yeah.’”
Now his entrepreneurial work has become his full-time gig, and McTear is fully in his element. “It’s in my blood,” he says, “and always has been.”
