Pensacola’s Sons’ Graham Guirl and Rafael Simpson Invest to Revitalize Hometown

The two entrepreneurs’ portfolio connects hospitality, neighborhood gathering places and consumer brands, with Pensacola at the heart of their story.

PENSACOLA, FL, UNITED STATES, October 9, 2026 /EINPresswire.com/ — For entrepreneurs Graham Guirl and Rafael Simpson, building businesses with national reach goes hand in hand with investing close to home. Through Dean Street, the Pensacola-based investment firm they co-founded, the two business leaders are growing a portfolio that connects boutique hospitality, neighborhood gathering places and consumer brands—with Pensacola at the heart of their story.

A friendship of more than 15 years started on the Pensacola tennis courts where Graham and Rafael bonded over their love of the town and dreams of what it could become. As a teenager, Rafael skateboarded down Palafox Street and always loved the architecture of the then abandoned buildings; knowing even then this would be somewhere he could converge his love of art, entrepreneurship, and his hometown. A few decades later, Hotel Margot, a 45-room boutique hotel at 200 N. Palafox St. was opened. Once a bustling horse stable in the 1900s, the boutique hotel features Café Colette, a European-inspired locally owned and operated cafe and bakery. Its ribbon cutting and grand opening celebration is scheduled for Oct. 28, 2026.

“When you live in the community where you invest, the work is personal, and we knew we were the guys to help build Pensacola’s next chapter” said Guirl, co-founder of Dean Street. “These are streets we walk, businesses we visit, and places where we spend time with our families. We want to build things that our neighbors are proud of and that give people another reason to discover Pensacola.”

Originally from St. Louis, Guirl began his career in Chicago before moving to Pensacola in 2017, drawn by its potential. His work has since focused on multifamily and commercial real estate in Northwest Florida. Simpson moved from Barbados to Pensacola as a teenager and graduated from the University of West Florida. After a successful career as an artist and living in markets including New York, Los Angeles and Miami, he returned to Pensacola with his wife, Lauren, to raise their family.

Today, Dean Street’s portfolio includes Hotel Margot, Colette Café, Harry’s Proper Burger and Harry Roy, a private dining and social club, all founded locally in Pensacola. The firm combines its own investment capital with active involvement in the businesses and properties as operational managers, bringing Guirl’s real estate experience and Simpson’s entrepreneurial background into a sustainable business model.

“Pensacola has its own character and is a community worth investing in,” said Simpson, co-founder of Dean Street. “Hotel Margot is just one of many ways we’ve dedicated ourselves to bettering our community. From local protein coffee now on Target and Sprouts shelves nationwide, employing hundreds of local residents across the hospitality, marketing, and art industries, our goal is to give back to the city that served foundationally to the business leaders we’ve become.”

The pair continue to invest in historic downtown to preserve and amplify its beauty; where they’ve been willing to take certain calculated risks adding to the unique fabric of Pensacola. In addition to their business ventures, they’ve mentored and infused support in other local business owners and serve on local development committees.

About Dean Street
Co-founded by Rafael Simpson and Graham Guirl, Dean Street is a private investment and operating firm with interests in real estate, hospitality and consumer businesses. The firm invests its own capital and actively operates businesses and properties across its portfolio. Learn more at deanstreet.co.

Maya Brown
Catalyst Communications Group
maya@catalystcg.com

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