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Penny reign: CEO of super fast-growing startup shares leadership insights

Penny Hoarder founder and CEO Kyle Taylor discusses his views on leadership, the future of digital media, his acceptance of mindfulness and meditation, and how he still gets teased by his friends.

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He doesn’t dress in jeans, sneakers and a hoodie like Mark Zuckerberg, but Kyle Taylor, founder and CEO of St. Petersburg-based Taylor Media — and its popular website, — might be more of a man of the people.

Take one recent afternoon, when he was at work at a regular desk in the company’s fastidiously curated, open-plan space, forgoing his corner office with its sweeping views of downtown St. Pete. Why? The rapidly growing firm is in danger of running out of desk space, even after moving into its new 23,000-square-foot headquarters last fall. So Taylor often lets desk-less employees use his office.

Eschewing the trappings of his position also serves Taylor, 31, as a reminder of how far he has come since starting the Penny Hoarder in 2010, when he was drowning in more than $50,000 of student loan and credit card debt.

"I like to strategically take meetings in different parts of the building because I want to have the chance to see everybody, which has gotten harder now that we’re not all around one table anymore.”

“Learn how to breathe, or you’ll never finish each day,” says Taylor, 31, when asked about the pressures of leading a company that experienced revenue growth of 9,396% between 2013 and 2016. That rampant growth continues, with sales increasing by 80%, from $20.48 million in 2016 to $37 million last year. 

The source of those sales is branded content that reaches between 12 million and 17 million per readers per month, including 5 million fans of the Penny Hoarder Facebook page. Some of its big-name advertising clients include Uber, Lyft and Sam's Club. The company also brings in revenue by creating advertising campaigns that encourage readers to sign up for a client's email newsletter, download a client's app or register for a client's service. 


To back up Taylor's maxim about breathing, Taylor has instituted optional meditation and mindfulness breaks throughout the day at Taylor Media, which now occupies the entire eighth floor of the Tampa Bay Times building at 490 1st Ave. S., in St. Pete.

The company has a dedicated “quiet room,” where employees can go to meditate or work free of distraction and background noise.

“I wasn’t sure what to make of all of it, at first,” Taylor says, “but I trusted the person who was in charge of it, and it’s really changed things for me in a lot of ways. Dedicating 15 minutes a day to just breathing — it’s amazing what that can do.”

"A big part of our strategy over the next few years is to make deeper connections with our readers. And part of that means exploring new platforms where we can have different kinds of interactions."

As a startup, says Taylor, “There’s never an end to the to-do list, and there’s a lot of opportunities … it’s easy to get ‘shiny object syndrome.’ Things are always coming your way. So I’ve had to learn to be very careful about not over-extending myself and picking just one or two things to focus on each year.”

Apart from welcoming meditation and mindfulness into his life and company, Taylor says success hasn’t changed his leadership style much, if at all.

“The one thing that has stayed constant for me is that I try to remain very open and accessible,” he says. “I like to create an environment where people can not only talk to me in the hall but come talk to me about serious things. I like to strategically take meetings in different parts of the building because I want to have the chance to see everybody, which has gotten harder now that we’re not all around one table anymore.”

Mike Meidel, director of Pinellas County Economic Development, has known Taylor for just over a year. But even in that short time he’s picked up on some of Taylor’s unique leadership traits and skills.

“Empathy,” says Meidel, is a big part of Taylor’s success. “He’s trying to put himself in his readers’ position. He really gets it on personal finance — he’s been there. And he’s taken that experience and he’s used it in every area of his life.”

For example, explains Meidel, “He’s saying, ‘OK, I'm putting myself in the place of my employee and saying, well, what would I want in this space? What would I want in a work relationship, in a job, in a career? He’s just got a high level of empathy and you can feel it when you’re with him. He’s designed his entire company around that.”

Taylor, Meidel adds, is also highly creative with a diverse range of interests. That's reflected in the company’s whimsical, painstakingly decorated headquarters. “A lot of time, a CEO of a tech company is not going to take the kind of personal involvement as he did in that space,” Meidel says.

That involvement can be seen in the office’s many distinct features. It boasts an exercise area stocked with purple yoga mats emblazoned with the company’s Lincoln penny logo; a game room with shelves lined with puzzles and board games; a home-style kitchen and gathering space featuring a ping-pong table and arcade-style video games; and a library bursting with curios, including an oil painting of the actor Bill Murray clad in a high-ranking military officer’s uniform from antiquity.

"The color schemes, all the little tchotchkes and knick-knacks, the odd little quirky things … it puts you in a creative frame of mind," says Meidel.

Taylor is "juxtaposing things you wouldn’t expect to be there, but seeing that they have a relationship. And that’s what he’s doing with the company. He’s trying to bring in a variety of people who have different backgrounds and then say, ‘This is beautiful; this is cool; let’s build on this.’ I think that’s a big part of his success — taking all of these different ideas and blending them together and making everybody feel like they fit in, even though it’s kind of a wild mosaic there. "


Kyle Taylor at the headquarters of the Penny Hoarder and Taylor Media in downtown St. Petersburg. Photo by Mark Wemple.
Kyle Taylor at the headquarters of the Penny Hoarder and Taylor Media in downtown St. Petersburg. Photo by Mark Wemple.

The Penny Hoarder began life as a blog founded and written by Taylor that chronicled clever ways for cash-strapped people to both make and save money. When he started the business, Taylor was living in Maine and working in politics as part of the AFL-CIO's field and fundraising teams, but he yearned to return to the Tampa Bay area, where he had spent his formative years and made many good friends. He did so, and found office space in the 600 block of Central Avenue in downtown St. Petersburg.

Taylor's content struck a chord with readers and also got noticed by major media tastemakers like Oprah Winfrey, Good Housekeeping magazine, Woman's World magazine and NPR. It didn't take long for lucrative acquisition offers to come rolling in, as the company built both a large fan base and solid pool of advertising clients. 

Taylor decided to not only keep control of the Penny Hoarder, but also keep it in St. Pete, during the firm's growth surge because he wanted to be around other fast-growth companies. And on the flip side, Meidel says the presence of Taylor Media and the Penny Hoarder in St. Pete is a big boost to the area’s “cool factor.” 

“He's done so well with the media that he's been able to draw attention to the area,” Meidel says. “Then all these other companies are able to really capitalize on that with the interest of skilled employees coming to the area.”

Meidel’s organization, the city of St. Petersburg and the state of Florida made the St. Pete choice even easier, offering Taylor Media a tax credit package that will amount to $990,000 over four years if the company hits its job-growth targets.

So far, so good. Last November, when Taylor Media moved into its new headquarters, the company had 80 full-time employees. Today, that number exceeds 100 and the firm is well on its way to meeting the goal of 165 total employees.


Like many fast-growth businesses, Taylor has had to layers to manage the growth and maintain the high standards. He remains the sole owner of Taylor Media, and says the company still bootstrapped, now "has a more robust executive team."

Taylor also recognizes the Penny Hoarder and other independent digital media brands face enormous challenges from the likes of Google, Facebook and Apple — companies adept at controlling the flow of information and how people consume and share media.

In response, Taylor says Penny Hoarder fans can expect to see the brand move into TV and SMS, also known as text messaging, as it seeks new ways to connect with its audience. “We’ve been in pre-production for a few months on a 22-minute, cable-style show and we hope to go pitch it later this year,” he says. SMS, he adds, “isn't quite as sexy, but it's popular. It's got like a 97% read rate and it’s associated with the brand rather than the platform, which is important to us. Also, it’s outside of Facebook and Google control, which is another good thing.”

And it’s not just the challenge of brand recognition and loyalty in an era of near-limitless choices that keeps Taylor up at night; it’s the great unknown of where digital media is heading, and how to stay one step ahead of technological change.

“We all are taking guesses at how we think content will be consumed five to 10 years from now,” he explains. “But none of us really know for sure. And the media brands that are going to survive are the ones that have strong brand recognition and really loyal followers. Those are the brands that will be able to ride the waves of technology and different monetization trends. So that's what where we want to position ourselves.”

















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