About CR Holland

Chad b. Holland

Designated Managing Broker, Managing Partner & Co-Founder

Chad B. Holland is the co-founder and managing member of CR Holland Real Estate, specializing in mixed-use, hospitality, and multifamily development. Licensed in both Illinois and Florida, Chad brings more than two decades of experience in commercial development, construction management, and real estate brokerage.

Chad played a key leadership role in advancing Illinois’ first STAR Bond district—a 500-acre, $300 million destination anchored by retail, hotels, and a regional sports complex—helping to establish a new model for large-scale public–private development in the state.

Earlier in his career, Chad oversaw the award-winning Tapestry Park project in Jacksonville, Florida—named Best Mixed-Use Project in Northeast Florida by NAIOP in 2009—as well as Aloma Walk, a Publix-anchored shopping center in Winter Park near Orlando. His expertise spans entitlement, construction, capital structuring, and strategic partnerships, allowing him to guide complex projects from concept to completion.

A U.S. Navy veteran, Chad served aboard the USS Preble (DDG 88) as part of the Visit, Board, Search, and Seizure Team, earning Hall of Fame honors in basic training, an Honorman Award, and a Letter of Commendation from his commanding officer.

Chad is an active member of several professional organizations, including IAAPA, ICSC, NAIOP, the SWIL Leadership Council, and both the National and Illinois Associations of Realtors. He also serves on multiple ICSC committees and holds a U.S. Soccer National D License.

ryan t. Holland

Owner & Co-Founder

Ryan Holland is the co-founder and managing member of CR Holland Real Estate, where he oversees operations, finance, strategic planning, and business development. A graduate of Southern Illinois University Edwardsville with a degree in Economics and Finance, Ryan approaches development with a data-driven mindset—integrating financial modeling, market analytics, and strategic growth planning to guide the firm’s success.

Ryan has played a key leadership role in advancing STAR Bond–financed projects across the Midwest, helping establish CR Holland as a recognized leader in large-scale public–private development. His expertise in financial structuring and government incentives—including STAR Bonds, Tax Increment Financing (TIF), and Business Districts—enables the firm to deliver complex, high-impact projects that drive economic growth and community investment.

Under his leadership, CR Holland expanded into residential construction in 2010 and launched its property management division in 2016, now managing more than 500 residential units across downstate Illinois. He has structured over $500 million in project financing through STAR Bonds, TIF, HUD programs, private equity, and institutional lenders, and has helped develop hundreds of millions in projects across Illinois, Florida, and Kansas.

Ryan also brings extensive experience in multifamily brokerage, having directed the sale of more than 1,000 apartment units. His expertise spans complex financial modeling, incentive utilization, and capital planning for transformative mixed-use, multifamily, and destination developments throughout the Midwest.

He is an active member of IAAPA, ICSC, RASI, the Illinois Association of Realtors, and the National Association of Realtors. Outside of work, Ryan enjoys spending time with his wife and twin boys.

Robert Stephan

Executive Vice President, Development 

Robert Stephan is an accomplished public affairs and economic development professional with extensive experience in government and politics. Most recently, he served nearly four years as Vice President of Downstate Relations for Intersect Illinois, the state’s public-private economic development organization, now known as the Illinois Economic Development Corporation (IEDC).

Over the course of his career, Stephan has held leadership roles with several of Illinois’ most respected elected officials, including as Deputy Downstate Director for U.S. Senator Barack Obama, Downstate Director for Illinois Comptroller Dan Hynes and Attorney General Lisa Madigan, and Special Projects Director for U.S. Congressman Jerry Costello. His deep understanding of state and federal government operations has made him a trusted advisor in both the public and private sectors.

Appointed by Governor JB Pritzker, Stephan previously served on the Board of Directors of the Southwestern Illinois Development Authority (SWIDA), contributing to infrastructure and economic growth initiatives in the Metro East region.

Prior to joining Intersect Illinois, he founded and led Robert Stephan & Company, a communications and government affairs firm serving clients across Illinois for more than a decade. Stephan worked on both of President Obama’s Presidential campaigns and during the Obama and Biden administrations, served as a White House Advance Associate, helping implement events and engagements for the President and Vice President across the United States.

In his time as a U.S. Senate staffer Stephan led then Senator Obama’s efforts for former nuclear weapons workers who had obtained radiation induced cancers while working on the Manhattan Project. Stephan became a recognized expert on the federal EEOICA legislation and often testified around the country before the Presidentially appointed Advisory Board on Toxic Substances and Worker Health, helping recoup more than $40,000,000 in benefits for Illinois residents.

While at Intersect Illinois, Stephan led the State’s efforts to secure the $60,000,000 expansion of a Texas based company to Southern Illinois, and worked on the team to secure the $500,000,000 expansion and reinvestment of a global manufacturing company in their Illinois facility.