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Photo By Brian Tietz

Tom Matthews is a small business guy. “I love small businesses,” he says. “I like the struggles of small business, and I like small business people. They’re willing to go in and take a risk and put everything they’ve got on the line.”

Matthews has been coaching small businesses for decades. He’s learned in the trenches, owning a host of his own small businesses over the years—he started his most recent endeavor, Gem Payroll, in 2019 with his wife. The company offers payroll processing services “with all the bells and whistles of the big guys,” Matthews says, plus all the flexibility of a smaller company. “If the boss forgot to put hours in for somebody, we’ll put together one paycheck and run it to the office so they can get paid on Friday.”

Though Matthews’ father worked a corporate job, Matthews knew his own path was headed for entrepreneurship. He graduated college with a degree in accounting and worked for a big travel company in Chicago. But he made a promise to himself that by the time he turned 30, he’d make the leap into self-employment. His last corporate paycheck arrived on Dec. 31, 1986—his 30th birthday.

“It was time to take off the golden handcuffs and jump ship,” Matthews says. He never looked back. “Entrepreneurs are built different. We’re risk takers. We learn to close our eyes and jump. Hopefully there are no rocks down below, though sometimes there are.”

He’s developed a few strategies over the years for avoiding those rocks, both in his own small businesses and when he’s advising his clients. His first piece of advice is to network. “You need to make friends,” he says. “Small business people often get so caught up in their business that they forget to go to the chamber of commerce meeting.” Networking is key because it provides a group of friends and mentors to turn to in difficult times. “Never be afraid to ask for help,” Matthews says, “Never. That’s how relationships are built.”

His second piece of advice is one that new entrepreneurs often forget. “Cash is king,” he says. “All businesses have cash flow issues. Make sure you’re not spending all your cash on living expenses, because then you won’t be able to run your business.”

His final suggestion: Know the numbers. “So many small businesses don’t know their numbers,” Matthews says. “They know sales, but they don’t have a clue about anything else.” He suggests entrepreneurs make a forecast every month—or at least every quarter—and then compare their numbers to that forecast, taking into account their profit margins, operating expenses and net income percentages. Being able to compare the current set of numbers to previous months, quarters and years is key. “That way, you can start to control your bottom line.”

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