Dean Street founders invest in Pensacola with Hotel Margot and local brands

Pensacola entrepreneurs Graham Guirl and Rafael Simpson are expanding their Dean Street portfolio with hospitality, neighborhood gathering spots and consumer brands rooted in downtown Pensacola. Hotel Margot’s Oct. 28 ribbon cutting underscores how the pair are tying local investment to preservation, jobs and the city’s revival.

Why it matters: - Graham Guirl and Rafael Simpson are using Dean Street to channel capital into Pensacola businesses and properties they also operate. - The portfolio links downtown preservation, hospitality and consumer brands to local jobs and neighborhood activity. - The strategy puts Pensacola at the center of a growth model meant to keep more value in the city.

What happened: - Dean Street, the Pensacola-based investment firm co-founded by Guirl and Simpson, expanded its local portfolio with Hotel Margot, Colette Café, Harry’s Proper Burger and Harry Roy. - Hotel Margot is a 45-room boutique hotel at 200 N. Palafox St. - The hotel sits in a building that was once a horse stable in the 1900s. - A ribbon cutting and grand opening celebration for Hotel Margot is scheduled for Oct. 28, 2026.

The details: - Hotel Margot includes Café Colette, a European-inspired cafe and bakery that is locally owned and operated. - Dean Street combines its own investment capital with hands-on operational management across its businesses and properties. - Guirl’s background is in multifamily and commercial real estate in Northwest Florida. - Simpson moved from Barbados to Pensacola as a teenager, graduated from the University of West Florida and later built a career as an artist in New York, Los Angeles and Miami before returning to Pensacola with his wife, Lauren, to raise their family. - The two founders said their friendship began more than 15 years ago on Pensacola tennis courts. - Simpson said local protein coffee from their business is now on Target and Sprouts shelves nationwide. - Simpson also said the businesses employ hundreds of local residents across hospitality, marketing and art. - Dean Street’s website is deanstreet.co.

Between the lines: - The investment thesis blends nostalgia with redevelopment, especially around historic downtown Pensacola. - Guirl and Simpson are framing their work as both business growth and civic stewardship. - Their model is not passive investing; it relies on direct operating control, which can speed decisions and deepen local accountability. - The emphasis on mentorship and development committees suggests the pair are trying to shape the broader business ecosystem, not just their own holdings.

What's next: - Hotel Margot’s public debut on Oct. 28 will be the next visible milestone for Dean Street’s downtown push. - The founders said they will continue investing in historic downtown Pensacola and supporting other local business owners. - Dean Street is likely to keep pairing real estate with consumer and hospitality concepts as it grows.

The bottom line: - Guirl and Simpson are betting that hometown investment can be both profitable and place-making, with Pensacola as both the market and the mission.