Caber Hill Advisors, the leading advisory firm for privately held, middle-market businesses, is thrilled to announce that Craig Castelli, CEO & Founder, has been named one of Crain’s Chicago Business’ 2025 Notable M&A Dealmakers.
The Notable M&A Dealmakers recognition honors outstanding deal professionals whose leadership, strategic vision, and execution have significantly impacted the M&A landscape. Honorees are selected through a combination of peer nominations and editorial review, highlighting individuals who excel in navigating complex transactions with precision and integrity.
“I’m honored to be included among such distinguished professionals shaping the M&A field in Chicago,” said Castelli, who is also the host of The Close M&A Podcast, a weekly interview series where he navigates the complexities of buying and selling businesses. “This recognition is a testament to the dedication of our team and the trust of our clients as we guide them through thoughtful, value-driven transactions.”
Since he founded the firm in 2014, Castelli has grown Caber Hill Advisors into nationally respected advisory firm dedicated to guiding middle-market business owners through successful transitions, mergers, and acquisitions. He leads a high-performing team of nine professionals — including veteran Managing Directors and skilled analysts — with over $1.5 billion in closed transaction value across more than 500 deals. Since closing his first healthcare transaction in 2005, Craig has built deep industry expertise and a thriving middle market M&A practice.
Below is a sampling of significant M&A deals Craig has led in the last three years:
Led Racine Dental Group in its acquisition by Dental Care Alliance (January 2023), a landmark transaction for one of Wisconsin’s most established dental groups, home to 20 dentists and 85 operatories inside a 65K SF flagship facility. The deal marked a significant expansion of DCA’s Midwest footprint.
Advised Dr. Jashank Sampat in the strategic sale of his multi-location practice in the Philadelphia-area to the high-growth DSO, GPS Dental (November 2023).
Advised Areo Dental Group, a seven-location practice, in its acquisition of Smiles by Farr (February 2024), expanding their geographic footprint across greater Chicagoland.
Outside of Caber Hill, Craig serves on numerous non-profit boards, including Erie Neighborhood House, a 130-year-old community services agency based in Chicago’s near West Side, and Friends of Mitchell, which raises money for his children’s local Chicago Public School. He is also a member of the University Club of Chicago and the Association for Corporate Growth. A graduate of Marquette University, he now lives in Chicago’s West Town neighborhood with his wife and two children.
