When Demetri Tsolakis was nine years old and just tall enough to reach the counter at one of his family’s Greek restaurants in Western Massachusetts, he started working there. He’d go to the restaurant every day after school, finishing his homework in booth number one before delivering sodas to the customers. It was there he learned to speak Greek, through chatting with the regulars, learning about their kids, their pets, and where they went to school. 

Tsolakis grew up with a single mother who was born in Greece, moved to the United States, and worked three jobs to raise him and his brothers. She worked hard to send them to private schools, an opportunity she never had. She urged them not to go into the restaurant industry when they got older. “[My family] always wanted us to have a better life than they did,” Tsolakis says.

But despite his mother’s wishes, Tsolakis kept returning to restaurants, working in service and dipping his toes into management, even while he worked in investment banking and pursued a college degree in International Business. He remembers feeling frustrated while working his 9-to-5 corporate job, thinking that he didn’t want the rest of his life to be locked into this pattern. One day, he was walking around Boston and noticed a distinct lack of Greek restaurants. 

It made Tsolakis think about what growing up Greek-American meant to him — he loved that he came from a different background and had a different story. He was proud of his culture, and walking through the city that day he saw both lack and opportunity. “I wanted to show [Boston] what my culture and what our food and hospitality is about,” he says.

Filling a need

In 2017, he began his first solo restaurant venture with Greco, a fast casual Greek street food restaurant in Boston’s Back Bay. At Greco, they serve delicious Loukoumades, or Greek donuts, famous Greek salads, and gyro wraps. “I think the best way to express our culture is to show the street food,” Tsolakis says. The concept worked — since then, Greco has opened three more locations, and Tsolakis kept coming up with new ideas for growth while highlighting his cultural heritage. He dove into Greek wines and regional cuisine with the Back Bay restaurant Krasi, and Greek mythology-inspired cocktails with Hecate in Back Bay. He has another exciting concept coming soon to Brookline called Bar Vlaha, focused on authentic, home-cooked Greek food and drinks.

When he worked in finance, Tsolakis learned the value of building relationships with customers, and he brought that lesson with him to every restaurant and team he’s built. His hospitality group is named “Xenia,” after the Greek concept of hospitality, of turning strangers into friends. “We want [our guests] to get a taste of Greece. Not just the food, but also the hospitality. We want them to leave as a friend,” Tsolakis says. 

Lessons learned

He looked for that same sense of hospitality when he looked for a banking partner, too. In the year before opening Greco, he remembers having many different bank apps on his phone. Santander Bank was just one of them. He’d walk past Santander next to the gym he went to every morning, and one day someone greeted him in Greek.

Slowly, he started noticing how Santander treated him as more than a customer — they treated him like a guest. It happened slowly, with time — the daily greetings, learning his name, the handshakes, the birthday wishes, Tsolakis recalls. “It wasn’t like a sales pitch. It wasn’t cheesy. It was authentic. It was real. It just felt like home and what I do in my restaurants, I felt it through them.” Tsolakis eventually deleted all of the other banking apps off his phone, and worked with Santander through the expansion of all six of his concept restaurants. “You can tell they’re looking out for you, and that they got your back. That’s a feeling I never felt at any other bank.” 

For Tsolakis, the biggest lesson he’s learned from his restaurant business is the importance of loyalty. “I never use ‘I’ or ‘mine’ or ‘you work for me.’ No, it’s always ‘we,’ ‘together,’ ‘us.’ And when you have that loyalty, it just builds trust. You’re committed, you’re dedicated, and it doesn’t only mean good loyalty, you know, you go through the ups and downs, but you do it together.” He believes that in his relationships with his vendors and his employees. 

Expansion on the horizon

When he grows his restaurants, he’s not only thinking of growing the business, but how to help his team grow, too. He began his restaurant business with a team of ten, and today employs 120 people. One of his best friends even moved from Greece to join the team, because “he believed in [Tsolakis], and the operation, and the growth,” Tsolakis says. Another employee who applied for a job as a hostess at one of his restaurants back in the day now works as the marketing director at Xenia. “We have long-lasting relationships because we care, and that’s our biggest thing. ….They support me in the company by doing their roles, and I support them by giving them that work-life balance. You know, work isn’t everything, but if you enjoy what you do, it’s not going to feel like work,” Tsolakis says.

Tsolakis wants to keep growing — open new restaurants, expand to more locations, and soon, start building community outreach programs to find ways for him to give back. He’s particularly passionate about mentoring others on their career paths. For anyone who’s considering starting a small business, Tsolakis says: Do it. And don’t fear failure because it’s a learning experience on the way to success. “If it’s a passion of yours, there’s no bad idea, there’s no wrong idea. The risk is worth it.” 

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