Reporter’s notebook: Entrepreneurs say there’s ‘something special’ about St. Pete

The founders of The Penny Hoarder and InsideOut made it clear during the Rise of the Rest stop in St. Petersburg that the city is a big part of their company’s growth.

Top executives at both companies spent a lot of time talking about why they located their businesses in St. Pete when Steve Case, the venture investor behind Rise of the Rest, stopped in at their offices May 1.

Location is a big factor for Case, the co-founder of America Online and chairman of Revolution, a Washington, D.C.-based investment firm. The Rise of the Rest tour is designed to highlight promising startups in areas outside of the major technology hubs.

That’s why Case consistently asked, “Why here?” as he visited with entrepreneurs.

“We’re all in on St. Pete. We feel we are building something special here,” said Chad Nuss, chief revenue officer and co-founder of InsideOut, a sales innovation lab in First Central Tower that tests and measures ideas, then deploys and trains sales leaders. The company has grown to 150 employees, up from 25 in 2015, and expects to have 225 workers within two years.

Nuss and Christina Cherry, InsideOut’s co-founder and CEO, earlier ran companies in Silicon Valley and in San Francisco. There, a company the size of InsideOut would be just “noise,” Nuss said.

“We wanted to be here because it feels like the early stage of growth. It felt like the 1995 San Francisco when Netscape put out a little CD and we started building browsers,” Nuss said.

Steve Case (center) with the staff at InsideOut

The company’s St. Petersburg location gives it the ability to grow, Cherry said.

“You said something great earlier, Steve, when you said you can go fast on your own, but if you want to go far you need a team,” Cherry told Case. “St. Pete provides an opportunity for us to build a team of individuals across a very eclectic mix of experience, knowledge, desire and aptitudes, and then be able to retain them.”

As St. Petersburg’s startup community grows, there likely will be more competition for talent, she said.

“We have to be honest about that. As the environment grows, so does the competition. But for us being in St. Pete and getting in on the ground floor and being able to leverage all of that, it wouldn’t be possible without the people you meet today,” Cherry said. “People are the most important asset this business has right now for growth, and St. Pete provides that for us.”

InsideOut has been totally self-funded so far, and the cost of living and Florida’s lack of personal income tax are features in the area’s favor, Nuss said. So is the geography.

“Two blocks this way, I’ve got a nice bay. Four miles that way, I’ve got Gulf of Mexico. So normally you don’t see me in a jacket and shoes. I’m normally wearing flip flops and board shorts because that’s why I moved to Florida,” Nuss said.

Kyle Taylor (left), founder and CEO of The Penny Hoarder, with Steve Case

It’s amazing to have more than 300 days of sunshine, agreed Kyle Taylor, founder and CEO of  The Penny Hoarder, when the Rise of the Rest team dropped in at his office in the Tampa Bay Times building.

But it’s not the only thing, he said.

“We are sitting in a startup community that is supported by our city government, by our city leaders and most importantly supportive of each other. I hope that’s what you continue to hear on your tour today,” Taylor said. “I’ve never worked in a place where people are so interested in your success. Another startup founder down the street who’s working all-nighters too, but willing to pitch in and send you candidates or help you raise money, that is something that’s special to St. Pete.”

Taylor started his career in politics and racked up $50,000 in debt by the time he was 25. He said he never set out to be an entrepreneur but over the last eight years, he has grown what started as a blog into a personal finance website, into a publication that reaches 12 million people every month. The Penny Hoarder ranked No. 581 on the Inc. 5000 last year, with $36.9 million in 2017 revenue.

“A big reason this has happened is because we chose to be here in St. Petersburg,” Taylor told Case.

He didn’t address recent staff cuts, which the bootstrapped company said were done to position itself for the future. Taylor did cite other media industry factors, including proximity to The Poynter Institute, a leader in journalism education, as well as the Times. The Penny Hoarder and the Times are planning to jointly host an event to meet readers, Taylor said.

Two other St. Petersburg entrepreneurs, Preston Faykus, founder and CEO of voice analytics company RankMiner, and Reuben Pressman, founder and CEO of software firm Presence, also were high profile during Rise of the Rest, when they each took part in the Pitch competition, the final event of the stop here.

During Rise of the Rest’s kickoff, Mayor Rick Kriseman named Pressman as the city’s first Entrepreneur-in-Residence, as part of a two-year pilot program. He will serve as a champion, advocate and connector for both the entrepreneurial community and city government.

Mayor Rick Kriseman announced Reuben Pressman (seated, left), founder and CEO of Presence, would be the city’s first Entrepreneur-In-Residence.