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Chaifetz Group
Dr. Richard A. Chaifetz established Chaifetz Group in 2012 after building ComPsych Corporation into the largest global provider of employee assistance and...
Chaifetz Group
Dr. Richard A. Chaifetz established Chaifetz Group in 2012 after building ComPsych Corporation into the largest global provider of employee assistance and mental health services. The firm deploys only family capital originated from that business. Ross D. Chaifetz serves as Managing Director. The office pursues a flexible mandate across venture capital, private equity, real estate and opportunistic strategies. It participates through direct co-investments and SPVs rather than fund commitments. Confirmed holdings include Anthropic, M1 Finance, Beta Technologies, Passport, 15Five, Factor75, Backlot Cars and Cameo. The portfolio spans North America with additional exposure through sports assets in the United States and Europe. Chaifetz Group maintains a lean internal team supported by advisers and portfolio executives. It holds no disclosed additional offices beyond its Chicago headquarters in the NBC Tower. The firm owns residential properties in Lake Forest, Illinois and Delray Beach, Florida, and operates real-estate holdings that include multiple multifamily assets. In the last 24 months it expanded its pickleball portfolio through the acquisition of the St. Louis Shock franchise and related operating companies. The office's structural distinction lies in its direct ownership of operating sports franchises alongside traditional venture and private-equity positions. This creates an internal operating-company relationship that informs sourcing and governance across the broader book.
General information
Firm type
Single Family Office
Year founded
2012
Location
Region
North America
Country
United States
City
Chicago
Corporate office
Chicago, IL, United States
Principals
Dr. Richard A. Chaifetz
Chairman
Ross D. Chaifetz
Managing Director
Bob K. Jacobson
Chief Financial Officer
Ryan Brown
Vice President
Sector focus
Frequently asked questions
Who runs investment decisions at Chaifetz Group?
Dr. Richard A. Chaifetz serves as Chairman and sets overall direction. Ross D. Chaifetz acts as Managing Director and oversees day-to-day investment activity.
How does Chaifetz Group source proprietary deal flow?
The firm leverages Dr. Chaifetz's operating network from ComPsych and board relationships at Saint Louis University and the Field Museum. It also draws on sports-franchise ownership ties for introductions.
Does Chaifetz Group participate in fund commitments or only direct deals?
The office invests through direct co-investments and SPVs. It does not commit to external funds as a primary strategy.
What investment stages does Chaifetz Group typically target?
The firm focuses on late-stage seed through Series D. Check sizes range from $200k to $5M+.
Where does the underlying wealth come from?
Wealth originated from Dr. Richard Chaifetz's founding and sale of ComPsych Corporation, the global employee-assistance provider.
Does Chaifetz Group maintain philanthropic structures, and how are they separated?
The Chaifetz Family Foundation operates separately from the investment office. Dr. Chaifetz also serves on boards at Saint Louis University and the Field Museum.
What is Chaifetz Group's known posture on co-investments alongside external GPs?
The firm routinely joins rounds led by other investors, including Vista Equity, Aldrich Capital Partners and SoftBank, while maintaining direct ownership of its positions.
Profile maintained by Altss using OSINT (open-source intelligence), regulatory filings, licensed data partners, and verified direct submissions. Read the methodology. Last updated: . Continuous refresh with full update cycles at least every 30 days.
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