Philadelphia native Stanley C. Middleman, Founder and CEO of Freedom Mortgage, shares lessons from building one of the nation’s largest privately held mortgage lenders, leading through changing economic cycles, and navigating today’s housing market.
Stanley C. Middleman:
Stanley C. Middleman, founder and CEO of Freedom Mortgage, has led the organization for nearly four decades, transforming it into one of the nation’s largest mortgage lenders and a leading force in loan originations and servicing, with more than 2.5 million customers. The company is also a top Ginnie Mae servicer, with a strong focus on FHA and VA lending for military and underserved communities.
Middleman serves as Vice Chairman of the Philadelphia Phillies, underscoring his deep-rooted commitment to the region he proudly calls home. He also serves as the Alternate Governor and Chairman of the Executive Committee of the Portland Trail Blazers. A respected industry voice, he frequently speaks on leadership, entrepreneurship, and expanding access to homeownership as a pathway to stronger communities.
He serves on the Board of Directors of the Mortgage Bankers Association (MBA), is a member of the Housing Policy Executive Council and The Conference Board’s Committee for Economic Development, and is a trustee at his alma mater, Temple University. He has also served on the advisory boards of Intercontinental Exchange, Inc. (ICE), the MBA’s Residential Board of Governors, Freddie Mac, Fannie Mae, and Ellie Mae, and as Chairman of Cherry Hill Mortgage Investment Corporation, a publicly traded real estate investment trust.
Deeply committed to philanthropy, Middleman supports initiatives across healthcare, education, and community investment. In September 2026, he established the Middleman Center at Penn Medicine and launched the Middleman Fund to accelerate the institution’s most promising scientific discoveries. Earlier, in 2022, he helped expand access to world-class pediatric care by creating the Middleman Family Pavilion at Children’s Hospital of Philadelphia (CHOP) in King of Prussia.
Rachael Pritzker - Moderator:
Rachael J. Pritzker, Esq. is the CEO of Pritzker Law Group, which she founded in 2017 with her twin brother, Adam. Before launching the firm, she practiced at the Center City firm Zarwin Baum and then worked in City Hall as Legislative Counsel to Councilmember At-Large Allan Domb. She has drafted and passed real estate and business-focused legislation and has been recognized for her work by City Council.
In less than a decade, Rachael and Adam have built Pritzker Law Group into Philadelphia’s only certified women-owned real estate law firm, named the Inquirer’s Best Overall Law Firm three years in a row. Rachael leads the firm’s zoning, land use, and government relations practice, guiding everyone from homeowners and small property owners to major developers, institutions, and nonprofits through the city’s approval process, with an approval rate of over 95% before the Zoning Board of Adjustment and other City administrative boards.
In 2026, Rachael’s projects earned three Philadelphia Business Journal awards, among them Amy 5 at James Martin, a new $62 million, state-of-the-art School District of Philadelphia building. She is recognized by Super Lawyers and The Best Lawyers in America, is a PBJ 40 Under 40 honoree, and serves on the boards of the Building Industry Association and the Michael Ann & Saquon Barkley Hope Foundation.