Kyle Taylor made the leap from being a 2004 Lakewood Ranch High School grad to founder and CEO of The Penny Hoarder, a company with $35 million in annual revenue.
Along the way, he dropped out of college, worked as a Publix cashier, knocked on doors of political campaigns around the country, and racked up $50,000 of college tuition and credit card debt.
This week, the 31-year-old returned to Lakewood Ranch to talk about how the personal blog he started turned into a company that landed on Inc. magazine’s rankings as one of the fastest-growing private companies in America.
The Penny Hoarder is a personal-finance website based in St. Petersburg that publishes content about ways people can make and save money.
Taylor’s comments to a packed house at a Headliners Luncheon hosted by the Manatee Chamber of Commerce at the McClure Center contained insights valuable to entrepreneurs of all ages, but seemed to resonate especially strongly with millennials.
Taylor’s entrepreneurial spirit first surfaced during his student days at Braden River Middle School. He would search for grocery coupons for candy, and then bicycle from his home to a Winn-Dixie and buy as much candy as he could stuff into his backpack. He resold the candy to classmates at school and doubled his money.
“It was a thriving little enterprise,” Taylor said.
Even a salesman as talented as Taylor experienced fear when setting out to establish The Penny Hoarder, and that’s what he wanted to talk to the chamber of commerce audience about.
“There are a lot of expectations on us,” Taylor said of business owners.
Those expectations can lead to stress and self doubt. But if someone is doing something purposeful, it makes all the stress worthwhile, he said.
Taylor used his own experience in moving from Maine to Florida to establish what would become The Penny Hoarder as an example.
“After I moved to Florida, I procrastinated about hiring the right people and how to pay them,” he said. “I was too afraid of failing. You have to push past that fear.”
Before he found an office, he would meet with candidates at Starbucks and later around his kitchen table.
The problems really started after opening The Penny Hoarder.
“I felt overwhelmed. One of our servers went down. ‘Pam didn’t like Sam.’ I went home many days in tears thinking I’m not cut out to be a CEO,” Taylor said. “You wear a lot of hats when you start a business. I felt the demands of being a CEO and doing all those other things during the day.
“I can’t make payroll, my best employee just left and the office has termites,” Taylor continued.
What helped Taylor dig himself out was the realization that, “We all need a tribe.”
Looking at his audience, Taylor continued: “You are each other’s tribe. As entrepreneurs we have to support one another. When someone says, ‘I’m having a tough week at work,’ the first thing out of our mouths should be, ‘How can I help?’ ” Taylor said.
Asked about his path to success, Taylor said he liked being a college student, but always found himself pulled in other directions, such as working on political campaigns.
“I had a knack for being on losing campaigns. We lost a lot,” he said.
Not all paths to success lead through college.
“Too often, it (college) is the expectation of what happens after high school. There are a lot of different paths to success,” Taylor said.
Audience members peppered Taylor with questions during his presentation and afterward.
“I loved it. For someone my age — I am about to be 30 — it is inspiring to see someone like that. If he can do it, I can do it,” Chelsea Gruber said.
Likewise, Deidra Larkin, 29, came away impressed.
“I thought it was awesome. It gave us a lot of perspective on where to start as a millennial and going for what you believe in and not wasting time,” Larkin said.