Joseph Liemandt, founder of Trilogy and ESW Capital, is one of the most discreet yet influential figures in enterprise software, building a vast portfolio of companies by acquiring and optimizing underperforming software assets. After becoming a young tech millionaire with Trilogy in the 1990s, he shifted to a buy-and-build strategy through ESW Capital, assembling hundreds of enterprise software businesses and implementing data-driven, remote-first operational models long before they became mainstream. Known for his anonymity, contrarian discipline, and rigorous process engineering, Liemandt has quietly shaped the economics of enterprise software while amassing one of the sector’s most substantial private fortunes.

John W. Henry, billionaire investor and principal owner of the Boston Red Sox and Liverpool FC, built his fortune as a pioneering commodities trader before reshaping the global sports industry through Fenway Sports Group. After founding the quantitative hedge fund J.W. Henry & Co., he acquired the Red Sox in 2002 and led the team to multiple World Series championships, breaking the “Curse of the Bambino.” Expanding his sports empire internationally, Henry later bought Liverpool FC, guiding the Premier League club to Champions League and English title victories. Known for his data-driven, value-focused leadership, he has become one of the most influential owners in modern professional sports.

John Collison, cofounder and president of Stripe, is one of the youngest self-made billionaires in tech, helping build the financial infrastructure that powers much of the modern internet economy. Alongside his brother Patrick, he launched Stripe in 2010 to simplify online payments for developers and businesses, growing it into a global platform used by millions of companies—from startups to industry giants like Amazon and Lyft. Known for his product discipline, engineering rigor, and long-term focus on expanding digital commerce, Collison has positioned Stripe as a cornerstone of global fintech, enabling seamless payments and financial services across over 100 countries.

John Catsimatidis, billionaire businessman and founder of the Red Apple Group, built a diversified empire spanning supermarkets, energy, real estate, and aviation. After immigrating to the United States from Greece as a child, he left college to take over a small grocery store and expanded it into the Gristedes supermarket chain, later branching into oil refining and fuel distribution through United Refining. Catsimatidis also became a major New York real estate developer, adding residential towers and mixed-use properties to his portfolio. A prominent political donor, radio host, and philanthropist, he remains one of New York’s most outspoken and influential entrepreneurial figures.

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.

Jed McCaleb, pioneering software developer and blockchain innovator, is best known as a cofounder of Ripple and Stellar, two of the most influential protocols in the digital asset ecosystem. A serial entrepreneur with a long history in early crypto infrastructure, McCaleb created the first major cryptocurrency exchange, Mt. Gox, before selling it in 2011, and later launched Stellar to promote low-cost, decentralized cross-border payments. Beyond blockchain, he founded aerospace company Vast to pursue long-term visions in space habitation. Known for his technical creativity and unconventional path, McCaleb has helped shape multiple generations of internet and financial technology.

Jim Jannard, founder of Oakley and RED Digital Cinema, is a self-made billionaire whose innovations reshaped both the eyewear and filmmaking industries. Starting Oakley in 1975 with just $300, he revolutionized sports performance gear with proprietary materials and bold design, growing the brand into a global icon before selling it to Luxottica for over $2 billion. Never one to slow down, Jannard went on to disrupt Hollywood with RED Digital Cinema, introducing high-resolution digital cameras that transformed modern filmmaking. Known for his rebellious streak, obsession with engineering excellence, and aversion to the spotlight, Jannard remains one of America’s most influential product visionaries.

Jack Dorsey, tech entrepreneur and cofounder of Twitter and Block (formerly Square), has been a defining figure in the evolution of social media and digital finance. As Twitter’s cofounder and longtime CEO, he helped shape modern online communication, while at Block he revolutionized mobile payments and financial inclusion through technology. Known for his minimalist leadership style and focus on decentralization, Dorsey has increasingly turned his attention to Bitcoin and blockchain innovation, positioning himself at the intersection of technology, finance, and social change.

Roy Carroll II, founder, president, and CEO of The Carroll Companies, has built a diversified real estate empire spanning multifamily housing, commercial developments, self-storage, and luxury communities. Based in Greensboro, North Carolina, the privately held company oversees billions in assets with projects across the Southeastern United States. Known for his entrepreneurial drive and long-term investment vision, Carroll has positioned his firm as a leader in regional real estate while also supporting civic and philanthropic initiatives that strengthen local communities.

Pedro Franceschi, Brazilian-born entrepreneur and technologist, is the cofounder and co-CEO of Brex, a fintech company transforming how startups and enterprises manage credit and financial services. A coding prodigy from a young age, he gained early recognition for developing tools to bring Siri to non-Apple devices before joining forces with Henrique Dubugras to launch Brex in Silicon Valley. Together, they scaled the company into a multibillion-dollar fintech platform, making Franceschi one of the youngest self-made billionaires and a leading voice in the future of global finance and technology.

Henrique Dubugras, Brazilian-born entrepreneur, is the cofounder and co-CEO of Brex, the fintech company revolutionizing corporate credit cards and financial services for startups and enterprises. A tech prodigy, he launched his first startup as a teenager before moving to Silicon Valley, where he and cofounder Pedro Franceschi built Brex into a multibillion-dollar company backed by leading investors. Known for his sharp vision and ability to scale fast-growing businesses, Dubugras has become a defining figure in the new wave of fintech, bridging Silicon Valley innovation with global entrepreneurship.

Harry Macklowe, New York real estate developer and art collector, is known for bold, high-stakes deals that reshaped the Manhattan skyline. Founder of Macklowe Properties, he developed iconic projects such as 432 Park Avenue, one of the tallest residential towers in the Western Hemisphere. His career has been marked by both spectacular successes and dramatic setbacks, including a leveraged $7 billion office portfolio purchase in 2007. Beyond real estate, Macklowe gained global attention for his blue-chip art collection, reinforcing his image as one of New York’s most colorful and audacious moguls.

Gary Friedman, chairman and CEO of RH (formerly Restoration Hardware), transformed the home furnishings retailer into a high-end lifestyle brand synonymous with luxury design. Since taking the helm in 2001, he has repositioned the company through bold merchandising, exclusive collections, and immersive gallery spaces that blend retail, hospitality, and experience. Under his leadership, RH’s market value has soared, redefining the intersection of home décor and aspirational living while establishing Friedman as one of retail’s most innovative and uncompromising leaders.

Gabe Newell, cofounder and president of Valve Corporation, turned a small game studio into one of the most influential forces in the video game industry. After leaving Microsoft in 1996, he launched Valve with Mike Harrington, debuting the groundbreaking title Half-Life and later creating the Steam platform, which revolutionized digital game distribution. Under Newell’s leadership, Valve has become a multi-billion-dollar powerhouse known for innovation, fan engagement, and industry-defining franchises, making him one of gaming’s most respected and enigmatic figures.

Evan Clark “Ev” Williams is an American pioneer of the social internet. He co-founded Pyra Labs, created Blogger, served as CEO of Twitter (2008–2010), and launched Medium, a leading long-form publishing platform. A graduate by drop‑out who popularized blogging and micro‑blogging, he now leads the impact investment firm Obvious Ventures.

Dean Solon is a self‑made billionaire and founder of Shoals Technologies Group, a leading provider of electrical balance-of-systems gear for solar farms. He took Shoals public in January 2021 and still owns about 40% of the company. Despite the IPO windfall, Solon remains hands‑on—recently launching Create Energy, a vertically integrated solar manufacturing venture aimed at reshaping the industry with U.S.-based production. 

David Zalik is the Canadian‑American entrepreneur who co‑founded GreenSky in 2006. After founding MicroTech at age 14 and launching several tech ventures, he built GreenSky into a fintech unicorn connecting banks, contractors, and homeowners in home‑improvement and healthcare financing. He remains a billionaire with over 50% ownership of the company. 

Daniel Ek is the Swedish-born co-founder, Chairman & CEO of Spotify, the global streaming platform launched in 2006. A tech prodigy who sold his first startup at age 23, Ek scaled Spotify to over 276 million premium subscribers and 696 million total users by mid‑2025. He also chairs Neko Health and leads European moonshot investments through Prima Materia. 

Chris Wanstrath is an American technology entrepreneur and co‑founder and former CEO of GitHub, the world’s leading software collaboration platform launched in 2008. Self‑taught and briefly enrolled at the University of Cincinnati, he grew GitHub from a side project to a global developer hub with millions of users, eventually selling it to Microsoft in 2018 for $7.5 billion. He later founded Null Games in 2023 and co-launched the non‑profit Ladybird Browser Initiative in 2024

Bradley “Brad” Jacobs is an American serial entrepreneur and dealmaker renowned for founding and steering multiple multibillion‑dollar companies—including United Waste, United Rentals, XPO Logistics, GXO, RXO, and now QXO. He’s completed more than 500 acquisitions across logistics, waste, and equipment rental, introducing an unusual leadership style focused on meditation, employee bonding, and operational rigor.