Sam Stair

Board of Directors

Founder, S2 Real Estate and S2 Technologies

Sam Stair brings over two decades of experience in real estate investment and technology leadership to the Rental Property Association of Wisconsin. After earning his degree in Management in Computer Systems from the University of Wisconsin–Whitewater, Sam moved to the Milwaukee area in 1998 to begin his career in IT services.

In 2001, he transitioned into residential real estate investment, steadily building a diverse portfolio that now includes more than 700 units. His holdings are primarily residential apartments, complemented by commercial properties such as larger office spaces, daycares, an underground house, and student housing in Boca Raton, Florida.

Through S2 Real Estate, Sam oversees the self-management of this portfolio along with an additional 200 units for a select group of investors. His team of 30 in-house staff and contractors ensures efficient operations and high-quality service across all properties.

Sam’s entrepreneurial vision and commitment to both real estate and technology continue to shape his leadership within the industry and his contributions to RPA’s mission.