Mark Cuban, entrepreneur, investor, and owner of the Dallas Mavericks, is one of the most recognizable figures in American business, known for turning bold bets into transformative ventures. After selling Broadcast.com to Yahoo! at the height of the dot-com boom, Cuban built a diversified portfolio spanning sports, media, technology, and healthcare. He later disrupted pharmaceutical pricing through the Mark Cuban Cost Plus Drug Company, applying direct-to-consumer economics to lower drug costs. Outspoken, data-driven, and intensely competitive, Cuban blends venture investing with consumer advocacy, making him a defining personality in modern entrepreneurship.

John H. Ruiz, founder and CEO of MSP Recovery, transformed a boutique health-care-law practice into a leading national firm specializing in recovery of Medicare, Medicaid and insurance reimbursements. Since launching MSP Recovery in 2014, Ruiz has built the company into a multibillion-dollar enterprise using proprietary data analytics and legal expertise to reclaim improperly paid claims on behalf of providers and payers. Under his leadership, MSPR has expanded into adjacent services and continues innovating in health-care compliance and recovery, establishing Ruiz as one of America’s foremost entrepreneurial leaders in health-care litigation and finance.

Hussain Sajwani, founder and chairman of DAMAC Properties, is one of the Middle East’s most prominent real estate developers, known for transforming Dubai’s skyline with luxury residences, branded towers, and large-scale master-planned communities. Starting as a catering entrepreneur serving energy companies across the Gulf, Sajwani shifted into property development in the early 2000s, building DAMAC into a multibillion-dollar enterprise recognized for partnerships with global brands such as Versace, Fendi, Cavalli, and Paramount Hotels. With projects spanning the UAE, Saudi Arabia, Qatar, Jordan, London, and beyond, Sajwani has become a defining figure in luxury real estate and one of the region’s most influential business leaders.

Jerry Jones, billionaire businessman and owner of the Dallas Cowboys, transformed the franchise into the most valuable team in global sports through bold management, aggressive marketing, and a relentless focus on brand expansion. Since purchasing the Cowboys in 1989, Jones has overseen multiple Super Bowl victories, built state-of-the-art facilities like AT&T Stadium and The Star in Frisco, and reshaped NFL business economics through media deals and sponsorship innovation. A polarizing yet visionary figure, he has turned the Cowboys into a cultural and commercial powerhouse while becoming one of the most influential owners in professional sports.

Barry Zekelman, executive chairman and CEO of Zekelman Industries, leads North America’s largest independent steel pipe and tube manufacturer, a company he and his family built into a dominant force in the industrial and construction supply chain. After taking over the business at a young age following his father’s passing, Zekelman expanded the company through bold acquisitions, vertical integration, and major investments in advanced U.S. manufacturing. Known for his outspoken advocacy of domestic industry and blue-collar jobs, he has positioned Zekelman Industries as a key supplier to infrastructure, energy, and commercial projects across the continent.

Omar Al Futtaim, vice chairman and CEO of the Al-Futtaim Group, oversees one of the Middle East’s largest and most diversified conglomerates, with operations spanning automotive, retail, real estate, finance, and logistics. Under his leadership, the Dubai-based family empire—known for partnerships with brands such as Toyota, Lexus, IKEA, and Marks & Spencer—has expanded across the Middle East, Asia, and Africa. Al Futtaim has guided the group’s transformation through digital modernization, large-scale real estate developments, and strategic global acquisitions, solidifying its position as a cornerstone of regional commerce and one of the UAE’s most influential private enterprises.

Dmitry Rybolovlev, billionaire investor and art collector, built his fortune through his majority stake in Uralkali, one of the world’s largest potash producers, before divesting and shifting into global investments. Known for high-profile real estate purchases across Monaco, Switzerland, the United States, and Greece, he has also been a major figure in the international art market, assembling a celebrated—and controversial—collection of masterpieces. As owner of AS Monaco FC since 2011, Rybolovlev has guided the club through periods of strong performance, including a Ligue 1 title. Despite legal disputes and intense media attention, he remains one of Europe’s most notable and influential private investors.

Gary Klesch, founder and chairman of the Klesch Group, is a veteran industrialist known for acquiring and restructuring distressed industrial and commodity businesses across Europe. Since launching his firm in 1990, he has built a portfolio spanning chemicals, metals, refining, and energy, often stepping into complex turnaround situations that larger corporations avoid. With a reputation for decisive management, deep operational expertise, and a contrarian investment approach, Klesch has transformed underperforming assets into competitive enterprises while establishing the Klesch Group as a major player in European heavy industry.

Patrick Dovigi, founder, president, and CEO of GFL Environmental, has built one of North America’s fastest-growing waste management and environmental services companies. Starting GFL in 2007 with a single truck operation, he executed an aggressive consolidation and acquisition strategy that transformed the business into a multibillion-dollar green-branded powerhouse operating across Canada and the United States. Known for his dealmaking acumen, entrepreneurial intensity, and distinctive “Green For Life” vision, Dovigi has reshaped the competitive landscape of waste collection, recycling, and infrastructure services while maintaining one of the industry’s most recognizable consumer-facing brands.

James Clark, pioneering computer scientist and serial entrepreneur, has founded some of Silicon Valley’s most transformative companies. As cofounder of Silicon Graphics, Netscape, and Healtheon, Clark played a pivotal role in shaping modern computing, the internet, and digital health. His early vision helped usher in the dot-com era, with Netscape’s 1995 IPO marking a defining moment in tech history. Beyond business, Clark has devoted much of his wealth to scientific research, education, and ocean conservation, establishing himself as both an innovator and philanthropist at the intersection of technology and progress.

Ira Rennert, billionaire industrialist, is the founder of Renco Group, a private holding company with investments in mining, metals, manufacturing, and defense. Starting in the 1970s with junk bonds, he expanded into heavy industry, building a diversified empire that has included steel, magnesium, and automotive companies. Known for his controversial business practices as well as his immense wealth, Rennert also drew attention for constructing one of the largest private homes in the United States, the 62,000-square-foot Fair Field estate in the Hamptons. Despite criticism, he remains a powerful and enduring figure in American industry and finance.

Howard Marks, cofounder and co-chairman of Oaktree Capital Management, is one of the most respected investors in distressed debt and value investing. Known for his widely read investment memos, Marks has built a reputation for clear thinking on risk, cycles, and market psychology. Since founding Oaktree in 1995, he has helped grow it into a global alternative asset manager with more than $150 billion under management. Revered by peers like Warren Buffett, Marks combines investment mastery with thought leadership, making him a guiding voice for both professionals and individual investors.

Herb Chambers, self-made billionaire and founder of The Herb Chambers Companies, built one of the largest and most successful auto dealership groups in the United States. Starting with a single Cadillac store in 1985, he expanded into a network of more than 30 dealerships across New England, representing top luxury and premium brands such as Mercedes-Benz, Porsche, and Rolls-Royce. Known for his relentless focus on customer service and sales innovation, Chambers turned a struggling dealership into a multibillion-dollar enterprise, cementing his reputation as one of America’s top automotive entrepreneurs.

Al Waleed bin Talal Al Saud, Saudi billionaire investor and philanthropist, is the founder and chairman of Kingdom Holding Company, a global investment powerhouse with stakes in banking, hospitality, real estate, and technology. Known for high-profile holdings in companies like Citigroup, Four Seasons Hotels, and Twitter, he has combined bold, long-term investments with a flair for global deal-making. A member of the Saudi royal family, Al Waleed has also pledged the majority of his wealth to philanthropy, reinforcing his image as both a shrewd businessman and a global humanitarian.

Frank Fertitta III, chairman and CEO of Station Casinos, transformed a family business into a Las Vegas gaming powerhouse catering to local residents. Alongside his brother Lorenzo, he acquired the Ultimate Fighting Championship in 2001 for $2 million, steering its growth into a global sports phenomenon before selling to Endeavor in 2016 for $4 billion. With substantial holdings in real estate, hospitality, and gaming, Fertitta’s career blends bold deal-making with a deep understanding of Nevada’s entertainment landscape, securing his place among America’s most influential casino magnates.

Felix Baker is a highly influential biotech-focused investor and co-founder of Baker Brothers Advisors, a leading hedge fund specializing in healthcare and biotechnology investing. Through his firm, established in 2000, Felix manages over $20 billion in assets and helped generate an estimated $8 billion gain from early investments in Seagen. A PhD immunologist and Stanford alumnus, he also serves on boards of key biotech companies and contributes to Stanford’s biosciences initiatives.

Edward Scott “Eddie” Lampert is an American billionaire investor and founder of ESL Investments, established in 1988 after stints at Goldman Sachs and backing from Richard Rainwater. He famously orchestrated the merger of Kmart and Sears in 2005 and led Sears Holdings until 2019, after acquiring it via bankruptcy auction through Transformco. His record has been polarizing—praised for contrarian success at AutoZone and AutoNation, yet widely criticized for Sears’ collapse.

Dennis R. Washington is a self‑made billionaire industrialist who founded The Washington Companies, a diversified conglomerate spanning heavy construction, mining, railroads, marine shipping, aviation, equipment, and environmental cleanup. From starting with a single bulldozer in Montana, he built a business empire that now includes Seaspan Marine and Montana Rail Link—and is rated one of Montana’s wealthiest residents. 

David Geffen is an American entertainment mogul, record‑label founder, and philanthropist. He launched Asylum Records (1970), Geffen Records (1980), DGC Records (1990), and co‑founded DreamWorks SKG in 1994. His music and film empire helped define modern pop culture and Hollywood.

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.”