About
DJay Holdings

Built on integrity. Driven by results. Nationwide residential investment with a strong Central Florida presence and active projects beyond.

Who We Are

DJay Holdings LLC is a real estate investment company focused on acquiring undervalued properties, executing high-quality renovations, and creating value in the communities we work in — nationwide, with a strong presence in the Florida / Orlando area and active projects beyond.

We believe good deals are ones where everyone eats: sellers get a fair, professional close; buyers and tenants get quality housing; partners and contractors get respected; and we earn a return by doing the work well.

Dana Cowles, Co-Founder and Principal of DJay Holdings LLC
Co-Founder & Principal

Dana Cowles

Dana is an Emergency Medicine Physician, public speaker, and business coach whose drive extends well beyond the clinic. A self-described recreationally terrible poker player, he brings sharp analytical thinking and a passion for smart investing to every deal DJay Holdings pursues.

dana@djayholdings.com
Jason Cowles, Co-Founder and Principal of DJay Holdings LLC
Co-Founder & Principal

Jason Cowles

Jason brings a creative eye and entrepreneurial spirit forged through years in fashion and retail. As the owner of Don't Slip Just Drip — his own clothing line — he knows what it takes to build a brand from the ground up. Off the clock, you'll find him in the kitchen, where his passion for cooking matches his appetite for a great deal.

jason@djayholdings.com
Network

Trusted Partners

Local expertise that helps us move faster on acquisitions and renovations.

REALTOR® Partner

Dave Gambol

simpler.realestate · Louisville, KY & Southern Indiana

Louisville-area realtor partnering with DJay Holdings on acquisitions — clear, investor-friendly guidance through every stage of the deal.

KY License 270336
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Rehab / Construction Partner

J. Clark Baird

Louisville Investment Property LLC

Louisville rehab and construction partner supporting DJay Holdings renovations — maximizing value with clean, modern finishes while controlling materials, labor, and hold costs.

Louisville, KY
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