Jay is an innovative leader and entrepreneur, with over 20 years in lifestyle marketing, real estate, technology and experiential concepts. He uses his creativity and imagination to uncover opportunities across multiple industries. Jay is the CEO and Founder of Guesst Software, a creative leasing platform that disrupts standard lease agreements for physical retail and restaurant operations; CEO and Co-Founder of Lifestyle Labs, a boutique management consulting company; Co-Founder of the Content Studio of Westport, the only full-service content production studio within a 35-mile radius of Fairfield County; and host of Visionary’s Podcast, a series of unique stories from inspiring entrepreneurs and leaders.

Jay is passionate about connecting, inspiring and helping others, be it through a podcast, community organization, event or new technology. In consulting, he empowers direct-to-consumer brands, and provides sustainable, relevant value propositions in the real estate industry. On the technology side, Jay works on new software development for businesses and consumers. Personally and professionally, Jay is driven to help inspire individuals to grow and thrive, and foster inclusivity.

Jay grew up in Detroit, Michigan, studied at Howard University in Washington, D.C. and later moved to New York City, then Westport, Connecticut. After graduating, Jay worked in the music industry for Clive Davis, Arista Records and Sony Music. He developed multi-city tours for top recording artists including Celine Dion, The Notorious B.I.G., Usher, Whitney Houston, TLC and Pink. In 1997, Jay founded Tastemakers Media, which published a cutting-edge magazine throughout the U.S., featuring the best retail, entertainment and lifestyle offerings, domestic and abroad.

Jay then brought his expertise in lifestyle marketing to commercial real estate. As Director for Marcus Millichap and later Eastern Consolidated Properties, his real estate brokerage career flourished. He built his lifestyle and real estate consulting business through strategic placemaking in retail, restaurant and office spaces throughout New York City.

Jay lives in Westport with his wife, Crystal, and their two children, Jacob and Sofia. Jay is highly involved around town, fostering community events and mentoring local entrepreneurs and young professionals. Jay is the Co-Founder Startup Westport, a community of innovators, and Co-Founder of Westport 10, an organization that strives to make Westport a more diverse and welcoming town for people of color. He is also a board member of the Westport-Weston Family YMCA and Westport Library.