The two entrepreneurs’ portfolio connects hospitality, neighborhood gathering places and consumer brands, with Pensacola at the heart of their story.
When entrepreneurs decide where to put their money, the choice often comes down to numbers on a spreadsheet. For Graham Guirl and Rafael Simpson, co-founders of the Pensacola-based investment firm Dean Street, the calculation is far more personal — they’re betting on the streets where they grew up. Their expanding portfolio weaves together boutique hospitality, community-focused gathering spots, and consumer product lines, all anchored in the Florida panhandle city they call home.
The partnership traces back more than 15 years, to tennis courts in Pensacola where the two bonded over a shared affection for their city and ambitions for its future. Simpson, who arrived from Barbados as a teenager, remembers skateboarding down Palafox Street and being drawn to the architecture of buildings that sat vacant at the time — sensing even then that this was a place where he could blend his passions for art, business, and his roots. Fast forward a few decades, and the pair have opened Hotel Margot, a 45-room boutique hotel located at 200 N. Palafox St. The property, once a busy horse stable in the early 1900s, now also houses Café Colette, a European-style cafe and bakery that is locally owned and operated. A ribbon-cutting and grand opening celebration is set 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.”
Guirl’s path to Pensacola started in St. Louis, moved through Chicago, and landed in the panhandle in 2017, when he was drawn by the city’s untapped potential. His career since has centered on multifamily and commercial real estate across Northwest Florida. Simpson, meanwhile, graduated from the University of West Florida after relocating from Barbados as a teen. Following a successful run as an artist in cities like New York, Los Angeles, and Miami, he came back to Pensacola with his wife, Lauren, to start a family.
Dean Street’s current holdings reflect that dual background: Hotel Margot, Colette Café, Harry’s Proper Burger, and Harry Roy, a private dining and social club — all launched locally in Pensacola. The firm puts its own capital to work and stays hands-on as operational managers, merging Guirl’s real estate acumen with Simpson’s entrepreneurial instincts into a model designed for longevity.
“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 duo continues to pour resources into the historic downtown district, working to preserve and enhance its appeal while taking calculated risks that add to the city’s distinct character. Beyond their own ventures, they have mentored other local business owners and contributed to community 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
Why it matters: This hometown investment strategy shows how local entrepreneurs can drive urban revitalization without waiting for outside developers. By pairing personal history with professional expertise, Guirl and Simpson are demonstrating that community loyalty and financial returns don’t have to be at odds — a model other mid-sized cities might look to as they seek authentic growth.
