Chaifetz Group

Chaifetz Group is a private investment firm that deploys permanent family capital to support entrepreneurs, business owners, and management teams in building and expanding industry-disrupting businesses. The firm employs a flexible and enduring investment approach, spanning venture capital, private equity, real estate, and opportunistic strategies. They are known for their ultra-disciplined investment philosophy, which emphasizes long-term partnerships and a deep alignment of interests with their portfolio companies.

Founded in 2012 by world-class entrepreneur Dr. Richard A. Chaifetz, the firm is rooted in his principles and anchored by his capital. Dr. Chaifetz, also the founder, Chairman, and CEO of ComPsych Corporation, brings extensive operational and business-building expertise to the group. Chaifetz Group differentiates itself by providing hands-on operational guidance, flexible capital, and leveraging an unparalleled professional network and unique capital base to foster growth and challenge the status quo.

Chaifetz Group has a diverse portfolio of notable investments across various sectors. These include companies like Vulcan Pickleball, PICKLETILE, and DUPR in the recreational goods and sports industry, reflecting their interest in sports and media. They have also invested in technology-driven companies such as xAI (artificial intelligence), M1 Finance (consumer finance), Backlot Cars (online automotive marketplace), Beta Technologies (eVTOL aircraft), FLASH Parking, TimeDoc Health, and 15Five (performance management software). Their portfolio also features investments in major sports franchises like the San Francisco Giants (MLB) and Alpine Racing (Formula One), as well as the Major League Pickleball franchise, St. Louis Shock.

The leadership team includes Dr. Richard A. Chaifetz as Chairman and Managing Partner, Ross D. Chaifetz as Managing Director, Bob K. Jacobson as Chief Financial Officer, and Ryan Brown as Vice President. The firm is supported by a team of investment professionals, advisors, and portfolio company executives who collectively leverage their entrepreneurial and operational experience to optimize strategy, execution, and business models for their portfolio companies. The firm often focuses its investments in the Midwest, including Chicago, St. Louis, Kansas City, Indianapolis, and Nashville, recognizing overlooked opportunities in these regions.