It’s very fitting that I am sitting across from Ari Gejdenson in Ari’s Diner, one of three new establishments the young restaurateur has recently opened in Ivy City. Why? Because about 15 years ago, at the age of 20, he was opening his first restaurant in Florence, Italy, where he was playing professional soccer. It was an American-style diner named Ari’s Diner.

It is safe to say that the intervening years have kept Gejdenson busy. If you didn’t already know him, if you met Gejdenson on the street, you’d never believe he now owns eight restaurants across three neighborhoods in DC and employs over 300 people.

Exceptionally friendly and kind-spirited, and casual in a t-shirt and ballcap, he seems more like a best friend from college you’d grab beers with. But don’t be fooled by his modest, unassuming demeanor: Gejdenson has always been an incredibly driven, ambitious person. He cares deeply about his employees and is greatly involved in every establishment that comprises his Mindful Restaurant Group.

A native of Capitol Hill, Gejdenson has had an unconventional career trajectory. His mother taught at Montessori schools and his dad was a congressman. Displaying an early talent at soccer, Gejdenson was spotted by a scout. He dropped out of high school and followed his passion for the sport that would take him to Bolivia, Chile, Connecticut, and finally Florence, playing for San Gimignano.

Already showing signs of decision-making skills, he decided that professional soccer wasn’t a viable career choice. “Much like every other professional sport, in soccer you are considered obsolete at a comparatively young age. I wanted to make sure I wasn’t broke at 35,” Gejdenson says.

But what business opportunities could a 20-year-old American soccer player pursue in Italy? Gejdenson noted two things: that there were no late-night food options to end a boozy night out at before going home, and that many hotels were offering popular yet mostly terrible American-style brunches.

With the number of ex-pats and study-abroad students in Florence, Gejdenson decided to open Ari’s Diner. He flew a friend out to help him (a former server at The Diner in Adams Morgan), and went forward, maybe a tad naively, with his plan.

“I remember thinking, I’ll open a restaurant in Italy where I have no experience. I figured it’d take off real slow so I’d have time to work with it, and it didn’t. I started to get my ass kicked on levels that – it was so hard the first two years. But I learned through necessity.”

As Ari’s Diner took off, Gejdenson became friendly with Stefano Innocenti, the owner of a neighboring restaurant, Acqua Al 2. Innocenti took an instant liking to Gejdenson. Upon first meeting, he exclaimed, “Who are you? You remind me of me!”

It’s hard to imagine what a young American soccer player had in common with the middle-aged Italian proprietor of a popular Florentine restaurant, unless you know that Innocenti opened Acqua Al 2 at age 18. Not only a friendship but a partnership was born. Innocenti invested in the diner, and Gejdenson helped out at Acqua Al 2. They ran both together for about five years, before Gejdenson began feeling pressure to move back home, mostly from his mother.

“She kept saying, ‘Barracks Row is coming alive, you need to be opening places in DC, not Italy!’” he recalls.

However, Gejdenson met an obstacle in finding the perfect spot to open his inaugural DC restaurant, until Kitty Kaupp of Stanton Development Corporation (currently part of the team behind the massive Hine Project) called him and pitched 212 Seventh St. SE. And thus the DC iteration of Acqua Al 2 finally found a home.

Gejdenson dove headfirst into the design of the restaurant. He had so many ideas swimming around in his head, and found it challenging to incorporate everything. He had to be more focused. “As I was building Acqua, there was a lot of stuff I didn’t get to do. I kind of wanted to open another place, but running Acqua was so much that I didn’t really think of doing it.”

He did end up opening a speakeasy, Harold Black, nestled right above Acqua Al 2. But it didn’t take the same amount of work that opening a whole new restaurant does, and Gejdenson was busy with other establishments.

That changed at a fortuitous meeting at Peregrine Coffee, where Gejdenson was introduced to Jody Greene, of Greene & Associates, who offered him a lease at the building that housed the former HR-57 jazz club on historic 14th Street. Here was another outlet for Gejdenson’s creative spirit and drive. He opened Italian gastro-pub Ghibellina, named after the street he lived on in Florence, just before the explosion of restaurant openings along the 14th Street corridor. Le Diplomate, B Too, and Tico all opened within months of Ghibellina.

Despite his investors being nervous about the location, it struck a personal chord with Gejdenson. “I usually don’t like being in the mix of things, but as a kid, 14th Street just always felt like it needed to come back alive, so to be able to be a part of that was not something that I was going to turn down,” he says.

If there is one running theme in Gejdenson’s restaurant empire, it’s that he has a personal connection to each spot. Harold Black is named after his grandfather. “My grandfather always talked how, you think speakeasies are below a laundromat or something but it was much more common that they were just bars in people’s houses.” Gejdenson designed the space in keeping with that residential, homey speakeasy feel.

If Harold Black is a cozy nook, then the Denson, Gejdenson’s other liquor bar (obviously a play on his surname), is on the other range: sleek and sophisticated, all leather and brass.

When Gejdenson opened a jazz den in the basement space next door to Ghibellina, he called it Sotto, which means “below” in Italian. It has a sycamore slab bar, cozy booths, and bistro tables that look onto the stage. Gejdenson wanted to pay homage to the renowned musical history of the street.

The most recent additions to the Mindful Restaurant Group family are situated on a corner on Okie Street NE in up-and-coming Ivy City, where the Hecht’s Warehouse serves as a geographic centerpiece and is dotted with craft distilleries.

Gejdenson learned of Okie Street back when Dream nightclub (later Love nightclub) was the only thing on the street. He likened Ivy City to Williamsburg, Brooklyn, in the late 1990s, where there were no restaurants and little to motivate people to visit. Gejdenson knew Ivy City would be the place to go next. “It just feels good here, I got here and it felt great – like when I was a kid – and I try to do what feels good and not think about it too much.” Gejdenson even lives in the area now, with his wife (who operates Mindful Restaurant Group together with him) and their daughter.

In Ivy City, there’s Dock FC, a converted loading dock turned sports bar, mostly soccer, of course. La Puerta Verde (The Green Door) was inspired by a bar that Gejdenson saw on a beach in Mexico, and he wanted a Mexican-meets-warehouse feel. The result? Incorporating cutout shipping containers to form booths.

And then there is Ari’s Diner, his restaurant group coming full circle to that first establishment in Florence. Ari’s Diner is indicative of Gejdenson’s commitment to the people he employs. The diner serves as an informal training school where entry-level short-order cooks can learn the ropes and eventually move on to Gejdenson’s other restaurants.

“It’s a great place to train people, so when we need our next line cook at Acqua or Ghibellina or Sotto, we’ve already moved people from here to La Puerta Verde. I really believe that working with your staff and helping them be better at their jobs is so important; we’re all responsible for building them up. It doesn’t matter how good a restaurant you are or location, you can’t operate a restaurant without people.”

His establishments also organize and participate in fundraisers for the Capitol Hill Arts Workshop, Capital Area Food bank, and local youth soccer leagues, further emphasizing the commitment to the DC communities they call home.

It’s an exciting time for Mindful Restaurant Group and Gejdenson, who may be one of the youngest (and most hardworking) restaurateurs in the DC area. As a DC native, he’s especially tuned into the spaces he creates, the neighborhoods he operates in, and, most significantly, the people that help make Mindful Restaurant Group successful.