David A. Duffield is an American enterprise software pioneer. He co-founded PeopleSoft in 1987 and in 2005 co-founded Workday—both revolutionized HR and financial management systems. He later founded Ridgeline Apps, serving investment managers. At age 84, he’s also a philanthropist behind Maddie’s Fund and the Dave & Cheryl Duffield Foundation, with gifts exceeding $450 million.  

David Booth is the co-founder and Executive Chairman of Dimensional Fund Advisors, the global investment firm he launched in 1981 after studying under Eugene Fama at the University of Chicago. His firm pioneered factor-based investing and now manages over $800 billion in AUM. A major philanthropist, he gifted $300 million to name Chicago Booth School of Business. 

Darwin Deason is an American billionaire entrepreneur and founder of Affiliated Computer Services (ACS). Under his leadership, ACS became a global outsourcing powerhouse before being sold to Xerox for $6.4 billion in 2010. After the sale, Deason emerged as Xerox’s largest individual shareholder (~12%). He is also a high-profile Republican political donor and owner of the mega-yacht Apogee and an opulent La Jolla estate called “The Sand Castle.” 

Danny Wegman is the third‑generation leader and longtime chairman of Wegmans Food Markets, the privately held grocery chain founded in Rochester, New York, in 1916. He succeeded his father Robert as CEO in 2005, building the retail brand into a beloved regional empire of over 110 stores across 10 states.

Daniel J. Hirschfeld is an American billionaire and long-time chairman of The Buckle, Inc., the Nebraska-based retailer founded by his family. Owning roughly one-third of the company, he oversees a chain of over 440 apparel stores across 42 U.S. states and has transformed it into a durable casusal-fashion leader. His family legacy dates back to one of the original roots of denim retail.

Daniel D’Aniello is an American business leader and co‑founder of The Carlyle Group, one of the world’s largest private equity firms. A Syracuse and Harvard University alumnus, he served as vice president at Marriott before launching Carlyle in 1987. A decorated U.S. Navy officer, D’Aniello stepped down as chair in 2018 and now emphasizes philanthropy in veterans’ affairs and higher education. 

Craig McCaw is an American telecom visionary who transformed his family’s cable-TV company into McCaw Cellular, pioneering U.S. mobile networks in the 1980s. After selling the business to AT&T in 1994 for over $11 billion, he went on to build Nextel, Clearwire, and other wireless ventures—shaping modern cell-phone infrastructure. A Stanford graduate and dyslexia survivor, he continues investing through Eagle River Inc. and supports environmental, education, and tech philanthropy.

Craig Duchossois is an American billionaire investment executive and lifelong leader of the Duchossois Group, the diversified family firm originally built by his father, Richard L. Duchossois. Under his tenure, the firm became the largest individual shareholder of Churchill Downs, with over $700 million in equity. He has served in the U.S. Marine Corps, earned an MBA from SMU, and led the evolution of Duchossois Capital Management into a family office powerhouse.

Christopher “Kit” Goldsbury is the San Antonio–based billionaire who built his wealth through Pace Foods—taking over the company in 1977, buying it outright in the early ’90s, and selling it in 1994 to Campbell Soup for $1.1 billion. Today he leads Silver Ventures, the investment firm behind San Antonio’s revitalized Pearl Brewery district, and supports education and culinary causes through the Goldsbury Foundation. He keeps a famously low public profile.

Charles Zegar is an American technologist and billionaire investor who co-founded Bloomberg L.P. in 1982 alongside Michael Bloomberg, Tom Secunda, and Duncan MacMillan. As lead software architect, he built the original infrastructure for what became the Bloomberg Terminal—a core engine of global financial markets. Today he remains a discreet yet influential philanthropist through the Zegar Family Foundation. 

Charles Simonyi is a Hungarian‑American software pioneer, former Microsoft distinguished engineer, and space tourist. He architected the first versions of Microsoft Word and Excel, co-founded Intentional Software, and became the only private citizen to fund and complete two separate missions to the International Space Station—logging over 26 days in orbit. His tech and philanthropic impact includes endowed science professorships and arts funding at top institutions.

Charles Brandes is an American billionaire investor and value‑investing legend who founded Brandes Investment Partners in 1974. A protégé of Benjamin Graham, he built the firm into a global value-management powerhouse with upwards of $95 billion in assets at peak. Brandes authored Value Investing Today and remains deeply philanthropic, supporting causes such as the Salk Institute and diabetes research institutes.

Carl Thoma is a veteran private-equity pioneer and co-founder/managing partner of Thoma Bravo, one of the world’s largest software-focused buyout firms managing more than $130 billion in assets. A Stanford MBA and Oklahoma State alumnus, he began his career in 1980 with the predecessor firm GTCR and helped invent the “buy and build” consolidation strategy that underpins his longtime success in PE.

Cal Turner Jr. is the pioneering retail executive and philanthropist who transformed Dollar General into a national discount powerhouse. After joining the family business in 1965 and rising from warehouse sweeper to CEO, he expanded the chain from 150 stores to over 6,000, achieving more than $6 billion in annual revenue before retiring in 2003. His leadership was rooted in small‑town values, faith, and a mission to serve working-class communities.

Bruce Toll co‑founded Toll Brothers in 1967 with his brother Robert, turning it into a Fortune 500 homebuilder specializing in luxury housing across 24 states. As vice chairman—and principal of family office BET Investments—he now manages a real estate empire spanning six million sq ft of commercial space, 3,000 apartments, automotive dealerships, biotech ventures, and a portfolio reaching billionaire status.

Bruce Kovner is a self-made hedge fund billionaire and the founder of Caxton Associates in 1983, the global macro fund he led for nearly three decades. A Harvard graduate who once drove a NYC taxi and dabbled in harpsichord before launching a career in trading, Kovner turned $3,000 borrowed on a credit card into billions—later retiring to manage his firm CAM Capital and lead elite arts and education philanthropy.

Bill Alfond is an American investor and philanthropist who inherited a billion-dollar fortune when his father, Harold Alfond, exchanged Dexter Shoe Company for Berkshire Hathaway stock. A trustee and Maine community supporter, he co-founded the Bill & Joan Alfond Foundation and holds a minority stake in Fenway Sports Group alongside his siblings. 

Bennett Dorrance is the billionaire heir of Campbell Soup, serving as a longtime board member and key stakeholder with roughly a 15 % family stake. A University of Arizona graduate, he co-founded DMB Associates—a real estate development firm—and supports education through his Dorrance Scholarship Programs. He resides in Paradise Valley, AZ, and ranks among Arizona’s wealthiest individuals. 

Aubrey Chernick is a Canadian‑born entrepreneur and philanthropist who founded Candle Corporation (creator of the Omegamon mainframe-monitoring platform) and later developed cybersecurity firms NC4 and Celerium. After selling Candle to IBM in 2004, he has championed youth education, digital inclusion, and tech-driven social impact through the Candle Foundation and Chernick family initiatives.

Arturo “Arte” Moreno is the first Mexican‑American to own a major U.S. sports franchise after purchasing the Anaheim Angels in 2003. A self‑made billionaire, he built his fortune in billboard advertising—expanding Outdoor Systems into an $8 billion sale—then transformed the Angels into a $2.7 billion-plus franchise. His leadership spans sports, media and community investment.