7 in 11: John Simon

To John Simon, downtown Sarasota has something few other downtown areas in the country have.

“Enough of a critical mass of retail, arts, proximity to the water. Sprinkle in some neat neighborhoods, and you’ve got a really unique recipe,” he says. “An undiscovered gem.”

That recipe is why Simon and his Isaac Group Holdings development company chose to build here.

The firm is behind the Pineapple Square development — a two-phase project responsible for retail stores on Lemon Avenue and Main Street, such as clothiers Brooks Brothers and Eileen Fischer, which will open next month, Pastry Art and Sur la Table, and on State Street more retail and a possible hotel, condo units and/or office space.

Simon lists only a few other downtowns that are as “livable” as Sarasota’s — big names, such as New York City, Chicago, Seattle and Portland, Ore.

“How lucky you are to have a hardware store downtown that is not chased out by Home Depot or Walmart,” he says. “There are no less than four barbershops. This is a community that uses its downtown.
It’s unlike other downtowns that have burned out areas.”

When he was courting retailers for a development in Norfolk, Va., Simon had to employ artful tactics to keep company executives from seeing the undesirable places.

“As we drove, if there was something I didn’t want them to see on the right, I would point to the left,” he laughs. “I would only bring them between 11 a.m. and 1 p.m., because that was when most people were on the street.”

Simon has none of those concerns in Sarasota.

“This is the only city that I don’t care what time of day (retailers visit),” he says. “I even encourage them to walk around by themselves.”

The new year is going to be an important one for Pineapple Square. The City Commission last month granted a development-agreement change Simon sought that allows greater flexibility for Isaac Group Holdings.

Whereas the original agreement strictly called for 157 condos and about 85,000 square feet of retail space, the revised agreement allows Pineapple Square to build condos if they’re in demand or more office space or a hotel if there’s interest.

Simon said he’s been discussing the Pineapple Avenue and Lemon Avenue location with a number of three-star hotel operators, although he declined to name any, as he always does, until a contract is signed.

Originally planned to be completed in 2009, Pineapple Square’s condos have been on hold during the downturn in the economy.

Simon said many times last year that he was ready to build as soon as the market turned around. Two specific events have to occur for Simon to receive a green light for construction: Banks begin lending again and demand builds for condos, offices or hotels.

“If banks start lending, we’ll begin to have plans developed by mid-year,” he said.

Simon didn’t just fly into town wanting to build, collect his check and leave. He lives here full-time and has signed on as a board member of several civic groups — the Downtown Improvement District, Downtown Sarasota Alliance and Greenspace Policy Committee.

After Pineapple Square is complete, Simon will continue to call Sarasota home — he will move into one of his condos.

“I will be able to look down from my balcony and watch the transformation of downtown,” he said.

BIO
Age: 65
Hometown: Washington, D.C.
Family: Divorced with two children
Education: Attended George Mason University and Warren Wilson College
Occupation: Developer and planner

Contact Robin Roy at [email protected]