Kyle Healy

Real Estate Operator | Multi-Family & Furnished Rentals | Self-Storage Syndicator I’m Kyle Healy, Founder and Co-Host at Rolling Rook Capital, where I focus on real estate operations, co-hosting, and scaling multi-family and self-storage investments. I began investing in real estate in 2020 to build sustainable cash flow (for myself and my kids) and now specialize in operational execution—managing small multi-family portfolios of 4 to 10-unit properties (both furnished short-term, and mid-term & traditional long-term rentals) and partnering with passive investors to take down larger self-storage properties via syndications. My strength lies in taking deals from acquisition through operations—utilizing automation to optimizing performance and building long-term value for partners. Whether you’re interested in co-hosting support, joint ventures, or exploring syndication opportunities, I’d love to connect and help you build profitable real estate systems. Feel free to reach out, as I'm always open to growing my network and seeing where I can help others out.