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St. Pete’s first entrepreneur in residence brings passion, energy to the role

Margie Manning



Reuben Pressman is St. Petersburg's first Entrepreneur-In-Residence.

It’s no secret that Reuben Pressman loves St. Petersburg.

Now Pressman, founder and CEO of St. Pete-based software company Presence, is channeling his enthusiasm for the city and the opportunities it offers into an opportunity to help other entrepreneurs.

Jessica Eilerman, St. Pete’s small business liaison, introduced Mayor Rick Kriseman while Kyle Taylor, CEO of The Penny Hoarder, looked on at the kickoff for the Entrepreneur-In-Residence program.

Pressman is the city’s first Entrepreneur-in-Residence, an unpaid position as a liaison between city government and the entrepreneurial community, under a a two-year pilot program launched by Mayor Rick Kriseman and first announced during the Rise of the Rest stop at Station House on May 1.

Pressman told the St. Pete Catalyst he will focus on three areas. He will be an advocate and champion for entrepreneurs who already have established high-growth businesses here. He will work with organizations such as the St. Petersburg Area Economic Development Corp. to recruit more companies to the area, and he will help the city itself become more entrepreneurial, with more agile processes, tools and communication.

It’s part of a broader initiative to work with small businesses that Kriseman undertook after he was first elected.

“The heartbeat of St. Petersburg is its small business community and sometimes city government seemed out of step with small business,” Kriseman said a kickoff reception for the Entrepreneur-In-Residence program Thursday night. Shortly after he took office, he went on small business listening tours and created a new position, small business liaison, now held by Jessica Eilerman.

Pressman won’t be a city employee, but will fill a similar role.

“Reuben will be our eyes and ears, the guy you can turn to and say, ‘What is the city doing?’ Why is it not doing this, or maybe the city ought to think about doing this,” Kriseman said. “When not doing it every day, you don’t know what the challenges are. The impetus behind creating this program was to have that eyes and ears.”

Distinct needs

Entrepreneurs who start high-growth and scalable businesses have distinct needs, Pressman said.

They’re different than small brick-and-mortar businesses, such as retailers or restaurants, who play a vital role in the community but don’t intend to become million-dollar or billion-dollar businesses. They’re also unlike large and well-established corporations that have already gone through rapid growth and matured.

The entrepreneurial companies Pressman will focus on are “solely focused on how to grow and how to grow faster. Very often they are technology based, which enables high-growth and scalability. Very often they are focused on software as a service specifically, with potential to double or triple their revenue year over year or even quarterly. That rate of growth produces an entire other list of problems and needs and focuses for those entrepreneurs,” he said. “It’s also likely they are first-time entrepreneurs and they are learning as they go without a lot of precedent set for how to do what they are doing. Because a lot of it is technology-based, typically there’s not a long history or track record with how cities can support these types of companies. There’s only been a few that have done it well.”

He cited a handful of examples in St. Pete — his own firm, Presence, with campus engagement software; Intrinio, a financial technology firm; Gooee, with software for building owners, managers and tenants; PandaDoc, which offers document automation software; and The Penny Hoarder, a personal finance website.

“I think the misconception about entrepreneurs is that they are somehow born into knowing how to run a business and it’s just not the case. They are just regular people,” said Kyle Taylor, founder and CEO of The Penny Hoarder. “Having a community of entrepreneurs that you can share those day-to-day challenges with, whether it be finding space, hiring people, making sure you are complying with local laws and regulations —it’s helpful to have a group like this to reach out to.”

‘City of opportunity’

Pressman is a great fit for the role, Taylor said.

Entrepreneurs at the kickoff event.

Pressman was born in Tampa and grew up in north Pinellas County. He moved to St. Petersburg in 2008, before the current real estate and economic boom, and went to school at University of South Florida St. Petersburg, where as a student leader he got involved with the community.

“I look at St. Pete as a city of opportunity. I think the diversity of the people we have here, the passion for the city and the opportunity that is here is contagious. You don’t see it in every city, and it’s something I had as we were building and growing here and it’s something that I very much wish to continue to and encourage as others continue to grow here as well,” he said.

Being named Entrepreneur-In-Residence is an acknowledgement of the work Pressman already has done to build a strong network of local entrepreneurs and recruit companies here, most notably PandaDoc, a Silicon Valley company that opened its east coast headquarters in St. Petersburg in 2017.

He’s advised about 100 startups on building their products and branding and marketing. His firm, Presence, has doubled or tripled its revenue every year for five years.

“I’ve started businesses here, I’ve grown businesses here, I’ve sold businesses here, I’ve recruited businesses here and I’ve helped other companies grow here as well,” Pressman said, adding the Entrepeneur-In-Residence program “hit every angle there is when it comes to starting and growing and everything in between for these types of companies.”

One specific goal he’s been tasked with is creating a “Mayor’s Panel on Entrepreneurship,” representing all levels of entrepreneurial activity. That’s a great way to get people involved and have their voices heard, Kriseman said.

“This is a pilot,” Kriseman acknowledged at the Thursday kickoff event. “My goal is that this is really successful and the word pilot disappears, and this becomes part of our DNA on how the city grows its entrepreneur community and our startups.”

And while it’s been a major focus for Kriseman, who has about two and a half years left in office, Pressman is confident the program would continue under a new administration.

“To me, it’s an easy and obvious program to continue. It doesn’t use resources and from an economic development model, every study I’ve seen supports startups as being the main driver of growth,” Pressman said. “It’s a bipartisan issue.”

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