Brad Oleshansky

Brad Oleshansky is a serial entrepreneur, developer, and operator best known today as the Founder & CEO of The Motor Enclave, a ~$150M experiential motorsports and automotive "playground" in Tampa, Florida featuring a 1.72-mile performance track, a two-acre vehicle dynamics pad, a 100-acre off-road course, and a 40,000-square-foot corporate event venue. The facility opened in January 2024 and has sold hundreds of private garages, positioning it as one of the largest venues of its kind in the world. He is a two-time recipient of the EY Entrepreneur of the Year Award (2012 for Big Communications, 2018 for M1 Concourse).

Oleshansky spent the first roughly 12 years of his career as an entertainment attorney in Los Angeles. A graduate of Ithaca College (film, class of 1992) and Southwestern University School of Law (1995), he worked across the music and media world — including roles associated with Virgin Records and The Walt Disney Company — before shifting into marketing services. In 2004 he joined the newly formed digital/pharmaceutical marketing firm Big Communications as Chief Operating Officer, helping grow it from a handful of employees and under $1M in revenue to roughly 125 employees and $30M+ in revenue. He helped facilitate its 2008 sale to Meredith Corporation and served as CEO until departing in 2012.

After leaving Meredith, Oleshansky — a Michigan native and lifelong car enthusiast — acquired an ~87-acre former General Motors factory site in Pontiac, Michigan and developed M1 Concourse, a $75M+ auto-enthusiast destination with a performance track and hundreds of private garages, despite having no prior real estate or development experience. The project is widely credited with helping revitalize the surrounding Pontiac economy. He exited M1 Concourse in early 2019 to conceive and build The Motor Enclave in Tampa.

• Invests as an angel / founder-operator rather than through an institutional fund; activity is concentrated at the seed stage.
• His operator background (marketing technology, media/entertainment, experiential venues) shapes where he can add value beyond capital.
• Documented participation in early-stage software: Ditto Labs, an image/photo-analytics ("visual listening") marketing-tech startup.
• Values passion-driven, category-creating ventures — his own guidance is to "focus on what you love, not the status quo," a theme consistent with backing founders building something novel rather than incremental.