Meet the Five Winds Senior Living Founders
Your investment needs people who can evaluate the property and run the business.
When Reid Hamilton began looking for senior living options for his parents in Reno, he toured approximately 40 communities. The search made him think seriously about the choices families face and the kind of community he would want for his own parents.
He sought out Greg Cini, whose work focused on the relationship between care, leadership, and the people delivering it. Bryan Schachter brought the investment and capital experience needed to help translate that approach into a senior living platform.
Five Winds grew from that shared ambition: acquire communities thoughtfully, support the people who operate them, and create an investment structure capable of serving the business over time.
Founding Partner, Acquisitions & Development
REID HAMILTON
$64M+
largest net-metered solar company in Nevada
$300M+
self-storage developed and acquired
• Directs the strategic development, acquisitions, and platform growth for Five Winds Senior Living.
• Leverages an extensive background in institutional real estate with over $300M in successfully closed transactions.
• Demonstrates refined expertise in identifying high-potential assets and managing the scaling of complex operations.
• Serves as a proven entrepreneur who founded Nevada’s largest net-metered solar company, securing $64M+ in funding.
• Focuses on disciplined expansion and sustainable value creation within the senior living sector.
• Integrates high-level institutional rigor with a granular focus on market demand to drive investor performance.
• Ensures that every phase of platform growth aligns with the highest standards of financial and operational excellence.
GREG CINI
Founding Partner, Operations · Culture Curator
450+
employees across four AL / MC communities
25+ yrs
consulting to leading senior-living organizations
• Directs operational strategy and cultural integrity for Five Winds, leveraging 25+ years as a consultant to elite senior living organizations.
• Owns and manages a portfolio of four assisted living, memory care, and independent living communities in Ohio.
• Achieves superior occupancy rates and staffing stability through a culture-first approach that resolves labor and operational friction.
• Serves as the platform’s Culture Curator, driven by personal experience to build compassionate, high-performance environments.
• Translates human-centric care into scalable, institutional-grade excellence that stabilizes assets and secures investor value.
• Proven expert in converting market challenges into solvable cultural opportunities for long-term growth and operational success.
BRYAN SCHACHTER
Founding Partner, Chief Investment Officer
$6.2B
total senior housing deal capitalization
24,000+
units across portfolio
• Oversees all facets of capital strategy, deal underwriting, and investor relations for the Five Winds platform.
• Provides nearly two decades of high-level institutional leadership, specializing in senior housing investment cycles.
• Served formerly as Chief Investment Officer at Watermark Retirement Communities, managing assets across the risk spectrum.
• Spearheaded the execution of 70 transactions totaling $6.2B in capitalization and managing over 24,000 units.
• Bridges large-scale acquisition and disposition experience with an entrepreneurial focus as the founder of Celly Senior Living.
• Implements rigorous institutional standards into specialized housing assets to secure long-term financial stability.
• Prioritizes the delivery of superior risk-adjusted returns for partners through disciplined, data-driven investment structures.
An acquisition has to make sense from more than one perspective.
Reid evaluates the opportunity and the terms of acquiring it. Greg examines the care operation, leadership, staffing, and work required to run the community well. Bryan reviews the underwriting, financing, and capital structure.
That collaboration helps connect the business plan with what must happen inside the community. It also gives investors a team whose responsibilities extend from the purchase decision to ongoing operations.