Anna Olcese

Businessperson, Parent, And Community Volunteer




“Two years. That’s the maximum I’m willing to stay.”
Those were Anna’s words when, in 1998, her husband was recruited back to Gainesville to run the company he had interned for while they were in college at the University of Florida. Although living in Gainesville had been wonderful as a student, Anna couldn’t imagine living there as an adult. Today, she can’t imagine living anywhere else in Florida

Anna and her husband, Alex, grew up together in Miami and then moved to Atlanta weeks after graduating from UF. “I’m a big city person and wanted a big city life. The thought of living in Gainesville made me shudder,” she says. At first, being the trailing spouse was very difficult for her.

“I didn’t have friends here, I didn’t have a job, and I didn’t know my way around the non-student areas of town. I felt really lost.”To make matters worse, Anna had been working in marketing and business development in the tech industry in Atlanta and had no idea where she could get a tech-related job in Gainesville.

“It was 1998, and Gainesville was still on dial-up!” she says.Fortunately, a couple of months after relocating, Anna saw an ad for an opening in the marketing and public relations department at Shands Healthcare at the University of Florida. Little did she know then how taking that job would completely change her life.

It wasn’t the job itself that made the impact. It was the person who hired her, Angela Foote, as well as the people she met while she was there.Anna and Angela, whose husband was then a medical resident, immediately bonded and a friendship bloomed. Today, they again work together. Except instead of marketing the hospital system they market greater Gainesville and everything that it has to offer, all while helping to make the transition from relocation to resident as smooth as possible for those moving to the area.

“I’m very passionate about helping others find their place in Gainesville because I remember how challenging life was for me when I moved here,” says Anna. “Relocating to a new city is daunting, particularly if you’re the one being dragged along. It’s great for one partner because he or she has a job and is excited about a new beginning, but it’s terrible for the other because that person doesn’t know what his or her future holds.

”After working at Shands Healthcare for a little over a year, Anna finally found a tech company in Gainesville, and it’s there that she worked as project manager for interactive media until she had her daughter in 2001. “After becoming a mom, everything was a blur for a while,” says Anna. “Fortunately, that’s when I found my support network and made some of my very best friends.

That’s also when my daughter made some of her very best friends, and this year they will be graduating.”“It’s very emotional because it’s the end of a chapter and the beginning of an exciting new one,” she continues.That’s the beauty of Gainesville. Everyone here is in transition: new students, graduates, newcomers, and those who reluctantly leave.

Mostly everyone in Gainesville comes from somewhere else, so friendships are strong because friends become family.Throughout the 20 plus years of living in Gainesville, Anna has found a family not just of friends but also of business partners. As a serial entrepreneur who has started many businesses ranging from a corporate marketing, communications and event management company to a real estate group, Anna strives to use those invaluable connections and to help others do the same.

“There is a tremendous amount of talent coming into the area in the form of trailing partners, and they need for us to support them, whether its by helping them find their tribe or by helping them find a job,” Anna says.

So these days Anna is also in transition, not to a new city but into a new chapter, where one of her top priorities is to harvest the knowledge and relationships that she’s gained as a businessperson, parent, and community volunteer to help connect those who are relocating with those who already live and work in the area.

“I always say, ‘Put them in my car and they’ll be convinced to move here!’” She continues with a laugh, “Then we’ll become friends and they’ll never want to leave!”
If nothing else, two years here won’t be enough.

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