Strategic Real Estate
Investment
DJay Holdings LLC acquires, renovates, and repositions residential properties across the country — creating value in every deal we touch.
Built on Integrity.
Driven by Results.
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.
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.
[email protected]
Jason Cowles
Jason brings a creative eye and entrepreneurial spirit forged through years in fashion and retail spaces. 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.
[email protected]Our Investment Strategies
Fix & Flip
We identify distressed properties below market value across the country, execute strategic renovations, and sell at a premium — all types of deals considered.
- Purchase below market value
- Quality rehab in 4–8 weeks
- FSBO + MLS dual strategy
Short-Term Rentals
We acquire and reposition properties in high-demand tourism and travel markets nationwide, partnering with Evolve to maximize occupancy and nightly rental income.
- High-demand travel markets
- Evolve management partnership
- Optimized nightly pricing
Long-Term Rentals
We acquire and hold residential properties as long-term rentals, building a stable income-generating portfolio while providing quality housing in the communities we serve.
- Stable monthly cash flow
- Buy-and-hold strategy
- Residential & multi-family
Wholesaling
We source deeply discounted off-market properties and connect them with the right buyers — moving deals quickly and efficiently without the need for renovation.
- Off-market deal sourcing
- Fast contract assignments
- No rehab required
Our Current Properties
Experience DJay Holdings firsthand — check availability and book direct through Evolve.
Bonnie View 21
3,000 sq ft mountain retreat in the Blue Ridge Mountains featuring stunning views, 2 decks, a hot tub, and a fire pit. Minutes from Cataloochee Ski Area, Great Smoky Mountains National Park, and Asheville.
What Our Guests Say
“This home is absolutely beautiful and very spacious! Waking up to the beautiful Mountain View every morning was incredible. It was perfect for our family.”
“This house was everything listed and more! Everything you could possibly need is furnished. The beds and pillows were wonderful! The view from the decks was amazing! Highly recommend for larger families. Very quiet neighborhood. Overall it was perfect for us!”
“The home was cozy and well kept. Everyone had a wonderful time on the adjustable beds. The cabin was well stocked with kitchen appliances, utensils, spices. Telephone and TV reception was great. This place was fantastic!!!! We loved it — looking forward to revisiting.”
Let's Work
Together
Whether you have a deal to share, a question about what we do, or just want to connect — we'd love to hear from you. Reach out and we'll be in touch shortly.