For over 17 years, Matt Pistorio has been a leader in repositioning, leasing, and marketing commercial real estate assets in Chicago’s most challenging buildings. As co-founder of The Telos Group, he helped expand the firm’s portfolio from 5 million to over 25 million square feet, representing some of Chicago’s most iconic properties, including Willis Tower, Prudential Plaza, the Old Main Post Office, Citadel Center, and Aon Center.
In 2018, Matt transitioned to the ownership side of the business, joining R2 Companies as a principal, where he oversaw leasing and marketing for a 5.2 million-square-foot portfolio across Chicago, Minneapolis, and Milwaukee.
In 2019, he founded Madison Rose Leasing Company, named after his two daughters. In just five years, the firm has won and leased over 15 million square feet across every neighborhood and asset class in Chicago. Madison Rose has been nominated twice for Broker of the Year, a testament to its innovative approach and market leadership.
A two-time Greater Chicago Food Depository ‘Broker of the Year’ recipient, Matt is a graduate of the University of Illinois at Urbana-Champaign.
Commitment to Philanthropy
Beyond real estate, Matt is deeply committed to philanthropy and serves on the Board of Trustees for Casting for Recovery (CFR), a nonprofit that provides fly fishing retreats for women affected by breast cancer. His connection to the cause is personal—his wife, Gina, was diagnosed with triple-negative breast cancer in 2016, just two months after the birth of their second daughter. After 18 months of treatment, she achieved a complete response. Six years later, she overcame a brain tumor, a result of childhood radiation treatment.
An avid fly fisherman, Matt finds peace on the water and is passionate about CFR’s mission. His family—Gina, Madison, and Payton—along with the entire Madison Rose team, actively support the organization. They host Moonlight, an annual fundraising event that has raised nearly $800,000 in just four years, making them a national sponsor. In 2025, Madison Rose was named CFR’s Premier Sponsor after raising the most money for the organization nationwide.