Terry Taylor, founder and president of Automotive Management Services, built one of the largest privately held auto retail empires in the United States by quietly assembling more than 120 dealerships across the country. Starting with a single new-car dealership in Daytona Beach in 1982, Taylor expanded through disciplined acquisitions, local operating autonomy, and an unusually low-profile style that made him one of the least visible major figures in U.S. automotive retail. His majority stake in Automotive Management Services turned him into a billionaire while preserving the company’s reputation for scale without spectacle.

Aubrey Graham, known as Drake, is a global hip-hop icon and mogul who recently launched the "Iceman" era in early 2026. While navigating a major class-action lawsuit regarding his partnership with Stake.us, he remains a dominant commercial force, recently debuting the "Nite Sprite" and "Afters" meal through a 2026 McDonald’s x OVO collaboration in Toronto. His massive 2026 world tour aims to reclaim his streaming throne following the release of his ninth studio album. Beyond music, the "Global Ambassador" for the Toronto Raptors continues to expand his OVO empire into the culinary and tech sectors, maintaining a net worth of approximately $400 million.

Thomas Barrack Jr. is the U.S. Ambassador to Türkiye and the Special Envoy for Syria in the second Trump administration, where he serves as a pivotal figure in Middle Eastern diplomacy. A veteran private equity investor and the founder of Colony Capital (now DigitalBridge), Barrack has leveraged his decades of experience in the region to broker historic regional agreements. In early 2026, he played a lead role in integrating the Syrian government into the Global Coalition to Defeat ISIS and oversaw major infrastructure MoUs, including a milestone gas exploration agreement between Syria and Chevron. His current diplomatic portfolio emphasizes regional security through "shared responsibility," successfully managing the complex transition of territory between the Syrian Democratic Forces and the central government in Damascus.

Ted Waitt is the billionaire co-founder of Gateway, Inc. who famously built a PC empire from an Iowa cow barn before pivoting to global philanthropy. Today, he leads the Waitt Foundation and Waitt Institute, driving the "Blue Prosperity" movement to protect 30% of the world’s oceans. His work focuses on partnering with island nations—including Fiji, Samoa, and the Azores—to implement sustainable marine spatial planning and resilient blue economies. Beyond the sea, Waitt is a major benefactor of the Salk Institute and National Geographic, blending his entrepreneurial roots with a mission to preserve the planet’s biodiversity and advance biomedical research through biophotonics.

Stewart Rahr is the billionaire founder of Kinray, which he grew into the largest privately held pharmaceutical distributor in the world before its $1.3 billion sale to Cardinal Health in 2010. Known as the self-styled "Number One King of All Fun," Rahr is a permanent fixture in New York’s high-society and philanthropic circles. His Stewart J. Rahr Foundation has donated over $25 million to the Make-A-Wish Foundation alone, alongside significant contributions to cancer and medical research. A flamboyant figure with a reputation for grand charity galas and celebrity connections, he remains a central force in American philanthropy and land stewardship in the Hamptons.

Stephen Deckoff is the founder and managing principal of Black Diamond Capital Management, an alternative investment firm specializing in credit, distressed debt, and private equity. With over $11 billion in assets under management, Deckoff has spent decades navigating complex corporate restructurings, drawing on his early experience at firms like Drexel Burnham Lambert and Bear Stearns. He is known for a disciplined, operationally focused investment approach, often taking controlling stakes in middle-market companies to drive long-term value. Beyond his institutional work, Deckoff has made significant headlines for his large-scale real estate investments in the U.S. Virgin Islands, including the acquisition of the St. James islands for luxury resort development.

Scott Shleifer, senior advisor at Tiger Global Management and former longtime partner, is one of the most influential technology investors of the past two decades, helping deploy billions into high-growth public and private companies worldwide. During his tenure as a senior leader at Tiger Global, he played a central role in major investments across software, internet platforms, and global technology champions, blending public market expertise with venture-scale private investing. Known for disciplined analysis and concentrated positions, Shleifer helped shape Tiger Global’s reputation as a dominant force in crossover technology investing and continues to advise the firm and broader tech ecosystem.

Ronald Baron, founder and CEO of Baron Capital, built one of the most respected long-term growth investing firms by combining rigorous fundamental research with patient, conviction-driven portfolio management. Starting the firm in 1982, Baron developed a reputation for investing early in high-quality companies and holding for decades, compounding returns through long-duration ownership. He is widely known for his early, high-profile investment in Tesla, as well as success across technology, healthcare, and consumer sectors. Baron’s career reflects disciplined optimism, founder alignment, and a rare commitment to long-term value creation.

Richard Saghian, founder and CEO of Fashion Nova, built one of the most disruptive fast-fashion brands in the world by mastering social media, influencer marketing, and ultra-fast product cycles. Starting from a family retail background, Saghian scaled Fashion Nova into a global e-commerce powerhouse known for trend velocity, celebrity partnerships, and direct-to-consumer execution. His model reshaped the fashion industry’s marketing playbook, proving that Instagram-era distribution and data-driven design could outperform legacy brands. Beyond fashion, he has become a major luxury real estate buyer, making headlines for high-profile property acquisitions.

Micky Arison, chairman of Carnival Corporation, built the world’s largest cruise company into a dominant force in global leisure travel while also shaping professional sports as owner of the Miami Heat. After taking the helm of his family’s cruise business, Arison expanded Carnival through scale, brand diversification, and operational efficiency, overseeing multiple marquee cruise lines and a vast global fleet. Beyond travel, he transformed the Heat into an NBA powerhouse with multiple championships, applying a disciplined, culture-driven ownership style. Known for a low public profile and long-term focus, Arison remains one of the most influential figures in hospitality and sports ownership.

Michael S. Smith, cofounder, chairman, and CEO of Freeport Financial Partners, has built one of the leading private credit platforms focused on non-sponsored middle-market lending. Since launching Freeport in 2008, Smith has emphasized disciplined underwriting, downside protection, and long-term relationships with founder-led businesses, helping the firm scale into a multibillion-dollar manager. A veteran of leveraged finance, he guided Freeport through market cycles by prioritizing capital preservation and consistent income, earning the firm a reputation for reliability among institutional investors. Smith’s steady leadership has positioned Freeport as a cornerstone player in private direct lending.

José Fanjul, vice chairman and president of Fanjul Corp, is one of the most powerful figures in the global sugar industry, helping lead the multibillion-dollar conglomerate that includes Florida Crystals, Domino Sugar, and extensive real estate and energy holdings. After the family’s exile from Cuba, Fanjul played a central role in rebuilding and expanding the business across the United States and the Caribbean, transforming it into a vertically integrated sugar and agribusiness giant. Known for his strategic political relationships, long-term operating vision, and deep philanthropic commitments—particularly in education and community development—Fanjul remains a defining force in American agribusiness and one of the most influential private industrialists in Florida.

Jon Oringer, founder and executive chairman of Shutterstock, is one of the earliest pioneers of the digital content marketplace economy. In 2003, he launched Shutterstock as a one-man operation—personally shooting the site’s first 30,000 stock photos—before scaling it into a global platform offering millions of images, videos, and creative assets to customers in more than 150 countries. Oringer took Shutterstock public in 2012, becoming New York’s first tech billionaire, and has since focused on building Pareto Holdings, an investment firm backing early-stage startups in Miami and beyond. Known for his product intuition and bootstrap discipline, he remains a central figure in the evolution of digital media licensing.

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.

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.

Henry Kravis, cofounder and co-executive chairman of Kohlberg Kravis Roberts & Co. (KKR), is a pioneer of the leveraged buyout industry and one of private equity’s most influential figures. Alongside Jerome Kohlberg and George Roberts, he helped establish KKR in 1976, building it into a global investment powerhouse managing hundreds of billions in assets. Kravis became a Wall Street icon through landmark deals such as the record-setting acquisition of RJR Nabisco, chronicled in Barbarians at the Gate. Known for his dealmaking acumen and philanthropic contributions, he has shaped both modern finance and charitable giving.

Samih Sawiris, Egyptian billionaire and tourism mogul, transformed his family’s business acumen into a global hospitality and real estate empire. As founder of Orascom Development, he spearheaded the creation of integrated resort towns across Egypt, Europe, and the Middle East, blending luxury hotels, marinas, golf courses, and residential communities. Known for projects like El Gouna on Egypt’s Red Sea coast, Sawiris has combined visionary master planning with sustainable development, positioning himself as a leading force in high-end tourism and destination creation.

Salman Alhokair, Saudi businessman and prominent member of the Alhokair family, has played a key role in expanding the Fawaz Alhokair Group into one of the Middle East’s dominant retail, hospitality, and entertainment conglomerates. Building on the family’s legacy, he has overseen partnerships with top international brands and the development of large-scale shopping malls and lifestyle destinations. Known for blending global retail trends with regional market expertise, Alhokair continues to influence the evolution of consumer experiences across Saudi Arabia and the wider region.

Fawaz Alhokair, Saudi billionaire businessman, co-founded the Fawaz Alhokair Group and expanded it from a single menswear shop in 1989 into a retail giant representing leading global fashion brands. Under his leadership, the group diversified into shopping malls, hotels, and entertainment ventures, establishing a presence across the Middle East and beyond. Known for his entrepreneurial drive and ambitious expansion, Alhokair has played a pivotal role in modernizing Saudi Arabia’s retail landscape and connecting regional consumers with international brands.

Abdul Majeed Alhokair, Saudi businessman and investor, is a leading figure in the Kingdom’s retail, hospitality, and entertainment sectors. As a key member of the Alhokair family, founders of the Fawaz Alhokair Group, he has helped expand the conglomerate’s portfolio of international fashion brands, shopping malls, and hotels across the Middle East and beyond. Known for his role in diversifying the family business and embracing modern retail trends, Alhokair continues to influence the region’s consumer landscape through strategic investments and global partnerships.