Richard Chaifetz

Richard A. Chaifetz (born August 1953) is an American billionaire businessman, licensed neuropsychologist, investor, and philanthropist. Raised on Long Island, New York, he earned a B.A. in Psychology from Saint Louis University in 1975 (magna cum laude) and a doctorate in clinical psychology from the Illinois School of Professional Psychology in 1981. After completing his training, he opened more than a dozen outpatient and inpatient mental-health treatment centers before pivoting his strategy as the healthcare market shifted toward managed care and HMO models.

In 1984 he founded Chicago-based ComPsych Corporation, which he built into the world's largest provider of employee assistance programs (EAPs) and behavioral-health/GuidanceResources services. The company serves tens of thousands of organizations and well over 100 million individuals across 160+ countries, and Chaifetz remains its Founder and Chairman. His personal net worth has been reported in the range of roughly $1.4–2.8 billion.

Around 2011–2012 he launched the Chaifetz Group, a private investment firm and family office that deploys permanent family capital across venture capital and growth equity, private equity, real estate, and opportunistic strategies. His son, Ross D. Chaifetz, serves as Managing Director overseeing day-to-day investment activity, while Richard sets overall direction as Chairman; the team also includes CFO Bob Jacobson and VP Ryan Brown.

Beyond investing, Chaifetz is a prominent sports owner and philanthropist. He is a co-owner/executive partner tied to the Portland Trail Blazers, a partner with the San Francisco Giants, owner of the St. Louis Shock Major League Pickleball franchise (2023), and a minority stakeholder in the Alpine Formula 1 team (2023). His philanthropy includes more than $27 million to Saint Louis University — which named its business school (Richard A. Chaifetz School of Business), the Chaifetz Center for Entrepreneurship, and Chaifetz Arena in his honor — plus gifts to Miami University, the Field Museum, and the Brain Research Foundation.

• Invests permanent family capital rather than a traditional fund — describing the approach as "Enduring Capital. Contrarian Thinking. Proven Track Record."
• Backs entrepreneurs, business owners, and management teams building industry-disrupting businesses, emphasizing "true partnership" and a hands-on, operationally involved role in strategy and growth.
• Flexible, stage-agnostic mandate spanning venture capital & growth, private equity & opportunistic, and real estate; participates through direct co-investments and SPVs rather than fund commitments.
• Sector breadth includes fintech (M1 Finance), consumer/food (Factor75, Repurpose), HR/SaaS (15Five), logistics (Passport), aviation/eVTOL (Beta Technologies), AI (Anthropic), and creator/consumer platforms (Cameo).
• Values a permanent capital base and long time horizon as a differentiator versus fund managers facing exit timelines — a "no forced-exit" posture that appeals to founders wanting patient, aligned capital.