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Entrepreneur goes from debt to $37M business to now Hall of Fame

Kyle Taylor launched The Penny Hoarder in 2010.

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  • | 6:00 a.m. December 6, 2019
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The Collegiate Entrepreneurs’ Organization Hall of Fame has welcomed Penny Hoarder Founder and CEO Kyle Taylor into its ranks.

Taylor launched The Penny Hoarder website in 2010 as a blog that detailed his personal finance struggles and how he dug himself out of debt. His story struck a chord, and less than a decade later, Taylor Media, the company that publishes The Penny Hoarder, is a multimillion-dollar enterprise headquartered in the Tampa Bay Times building in downtown St. Petersburg.

“We are so thankful for Kyle’s efforts as an entrepreneur,” states James Zebrowski, executive director of CEO, in a news release. “Kyle is truly a brand disruptor, an innovator and somebody, we believe, our members would one day aspire to be like.”

With Taylor's success — he's also a former Business Observer 40 under 40 winner — has also come some stark business challenges, including staff reductions and copyright disputes. 

In 2017, the last year the company disclosed financial data, The Penny Hoarder generated $37 million in gross annual revenue and had 82 full-time employees. In March, however, the company made significant cuts to its workforce, partially due to social media changes to how its content is seen. “We’ve had to make difficult decisions to better position and reorganize ourselves for the future,” Taylor said at the time, “including the reduction of our team.”

Then, in May, Taylor filed a multimillion-dollar copyright infringement lawsuit against a larger competitor, New York City-based Fluent Inc., which operates websites called The Smart Wallet and The Bill Wizard.

Despite the recent challenges, The Penny Hoarder remains a leader in personal finance web content. Its reach is broader than ever, thanks to a partnership with the Tampa Bay Times, which publishes “Dear Penny,” a personal finance advice column in the Sunday business section. 

“I have a deep admiration and respect for the Collegiate Entrepreneurs Organization and its mission to support student entrepreneurship,” Taylor states in the release. “I’m humbled to be joining other CEOs and industry leaders in the Hall of Fame. The Collegiate Entrepreneurs Organization is doing great work in the Tampa Bay community and beyond. I hope it continues to encourage young entrepreneurs that anything is possible.”

The CEO Hall of Fame, the release states, includes founders of brands such as Kinko’s, Southwest Airlines, E-Trade, Staples, Jimmy John’s, Apple, iRobot, Crate and Barrel and


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