Vinod Khosla, cofounder of Sun Microsystems and founder of Khosla Ventures, is one of Silicon Valley’s most influential venture capitalists, known for backing bold, high-impact technologies across software, climate, biotech, and deep tech. After helping launch Sun Microsystems in the early days of the workstation revolution, Khosla turned to investing and built a reputation for funding ambitious, science-driven startups with transformative potential. Through Khosla Ventures, he has supported companies spanning artificial intelligence, clean energy, and healthcare, becoming a leading voice on technological disruption and long-term innovation.

Vincent Viola, founder of Virtu Financial, built one of the most sophisticated electronic trading firms in global markets by leveraging high-speed technology and quantitative strategies. A former chairman of the New York Mercantile Exchange, Viola transformed Virtu into a major liquidity provider across equities, currencies, and derivatives worldwide. Known for combining trading expertise with advanced infrastructure, he helped institutionalize high-frequency market making at scale. Beyond finance, Viola is the owner of the NHL’s Florida Panthers, linking capital markets success with professional sports ownership.

Vince McMahon is a billionaire entertainment mogul and the founder of 14TH & I, a private investment firm he launched in 2025 to focus on sports, media, and entertainment. Following his high-profile exit from WWE and TKO Group, he transitioned into this "entertainment hub" alongside former executive Brad Blum. In early 2026, his legacy remains entangled in a federal investigation and a civil sex trafficking lawsuit filed by Janel Grant, with a pivotal arbitration hearing set for June 2026. He recently made headlines when bodycam footage was released showing the aftermath of his 115 mph Bentley crash from the previous summer. Despite these legal and personal challenges, he maintains a net worth of approximately $3.5 billion and a significant minority stake in TKO.

Tyler Perry is a billionaire filmmaker and media mogul whose 2026 focuses on content dominance and large-scale urban development. In February 2026, his latest Netflix comedy, Joe's College Road Trip, debuted at No. 1, marking a successful franchise pivot by centering on Madea’s cantankerous brother, Joe. Beyond the screen, Perry is moving forward with a massive 1.3 million-square-foot "Entertainment District" adjacent to his 330-acre Atlanta studio, a project slated for completion in 2028 that will feature theaters, retail, and a museum. Despite a temporary pause on his $800 million studio expansion due to concerns over AI's impact on production, he continues to churn out hits like the second part of Beauty in Black Season 2, set for release in March 2026.

Trevor Rees-Jones is the billionaire founder of Chief Oil & Gas and a defining figure of the American shale revolution. Known as the "winningest fracker," he built a multi-billion-dollar fortune through strategic plays in the Barnett Shale, culminating in the $2.7 billion sale of his firm to Chesapeake Energy in 2022. In 2026, he remains a titan of Texas philanthropy, with the Rees-Jones Foundation surpassing $900 million in total giving. His current major project is the 2026 development of the Rees-Jones Library of the American West at Southern Methodist University, which will house his $100 million collection of rare books and art. His wealth continues to grow through significant stakes in Expand Energy and diversified real estate.

Travis Kalanick is the billionaire co-founder of Uber and current CEO of City Storage Systems, the parent company of the ghost kitchen giant CloudKitchens. Since his departure from Uber, he has focused on "the future of cities" through his 10100 investment fund, which targets real estate and e-commerce innovation. In late 2025, Kalanick made international headlines after being granted Saudi Arabian citizenship, a move reflecting his deep business ties in the Middle East where his "KitchenPark" brand is expanding rapidly. His 2026 strategy centers on integrating robotics and autonomous delivery via his startups Lab37 and Otter, aiming to replace physical restaurant storefronts with high-efficiency "internet food courts." His estimated net worth stands at $3.6 billion.

Travis Boersma is the billionaire co-founder and Executive Chairman of Dutch Bros Coffee, the drive-thru empire he launched with his late brother in 1992. As of early 2026, he remains the cultural anchor of the brand, overseeing a strategic push toward a target of 2,029 locations by 2029. Under his leadership, the company recently expanded its East Coast footprint by acquiring Clutch Coffee Bar and appointed new executive leadership to refine shop operations. While his "Flying Lark" resort project in Grants Pass remains a point of regulatory contention, his philanthropic legacy thrives through the annual "Drink One for Dane" campaign, which has now raised over $11 million for ALS research. His 2026 net worth is estimated at $3.1 billion, reflecting the company’s continued dominance in the quick-service beverage industry.

Tope Awotona is the billionaire founder and CEO of Calendly, the scheduling automation platform valued at $3 billion. After immigrating from Lagos, Nigeria, and bootstrapping the company with his life savings, he has grown the service to over 20 million monthly users. In 2026, he is leading a strategic shift toward "Agentic AI" to transform scheduling into a fully autonomous experience. Recently inducted into the Technology Association of Georgia Hall of Fame, Awotona remains one of the few Black tech billionaires in the U.S. and a major advocate for diversifying the tech pipeline through his support of organizations like Black Girls Code.

Tony Xu is the billionaire co-founder and CEO of DoorDash. In early 2026, he is leading a massive "AI-native" overhaul to unify international brands like Wolt and Deliveroo into a single global tech stack. Beyond scaling autonomous delivery with the "DoorDash Dot" robot, Xu is a vocal proponent of human-led fulfillment in the face of rising AI agents. A Meta board member and signatory of the Giving Pledge, he focuses his philanthropy on underfunded "dreamers and doers." His current strategy prioritizes long-term engineering leverage as the company expands into retail and grocery.

J. Tomilson Hill is a billionaire financier and world-renowned art collector currently serving as the Chairman of Private Investments at Two Sigma and CEO of Two Sigma Real Estate. After a storied career as Vice Chairman of Blackstone, where he grew its hedge fund business to $75 billion, he transitioned to Two Sigma in 2021 to lead its data-driven private market strategies. In 2026, he remains a titan in the cultural sector as the Chairman of the Guggenheim Museum and founder of the Hill Art Foundation in Chelsea. His foundation’s early 2026 exhibition, The Lost Beauty of Humankind, highlights his signature approach of pairing Old Master works with contemporary photography to explore universal human dignity.

Tom Preston-Werner is the billionaire co-founder of GitHub and a defining figure in open-source software, having created SemVer, TOML, and Jekyll. Now a General Partner at Preston-Werner Ventures (PWV), he focuses on "founder-first" investing. In early 2026, he launched PWV Fund I, a $100M vehicle to lead pre-seed and seed rounds for AI and software startups. A signatory of the Giving Pledge, he and his wife Theresa manage the Preston Werner Foundation, which supports climate resilience and global justice. Based in San Francisco, he remains a key mentor in the developer community, leveraging his experience to help builders navigate the ethical and technical challenges of the AI era.

Tom Gores is the billionaire founder of Platinum Equity and owner of the Detroit Pistons. In February 2026, he launched "Same Page Entertainment," a multimedia venture with Jalen Rose to spotlight Detroit’s creative talent. His sports portfolio expanded recently to include a WNBA franchise set to debut in 2029 and a minority stake in the LA Chargers. On the court, his Pistons have surged to the top of the Eastern Conference behind MVP candidate Cade Cunningham. A prolific philanthropist, Gores recently donated $350,000 to SAY Detroit to revitalize the historic St. Cecilia’s Gym. With over $50 billion in assets under management at Platinum Equity, he remains a dominant force in global private equity and Michigan’s economic resurgence.

Tom Ford is a billionaire fashion icon and filmmaker who defined modern glamour at Gucci and his namesake house. After selling his brand to Estée Lauder for $2.8 billion, he returned to cinema in 2026 to direct Cry to Heaven, a self-financed adaptation of Anne Rice’s novel. Set in 18th-century Venice, the film features an all-star cast including Nicholas Hoult, Aaron Taylor-Johnson, and Adele in her acting debut. While Haider Ackermann now oversees the Ford fashion label’s "seductive dialogue," the man himself is focused on this lavish operatic vengeance tale. Currently filming in London and Rome, the project marks his third feature and his most ambitious creative pivot to date.

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.

Dean Spanos is the billionaire owner and chairman of the Los Angeles Chargers, a role he formally assumed after the death of his father, Alex Spanos, in 2018. While he ceded daily operations to his sons, A.G. and John, in 2015, he remains the strategic leader of the franchise, steering it through its high-profile relocation to Los Angeles and the opening of SoFi Stadium. In early 2026, he continues to oversee the team’s long-term growth in the L.A. market and the development of their permanent training facility in El Segundo. Outside of football, he serves as CEO of A.G. Spanos Companies, managing a nationwide construction empire. His 2026 philanthropic efforts center on the Chargers Impact Fund, supporting local education and youth sports across Southern California.

Alan Smolinisky is a billionaire entrepreneur, principal at Conquest Housing, and co-owner of the Los Angeles Dodgers. He first built his fortune with Conquest Student Housing, which became the largest provider at USC before selling for $205 million in 2008. In 2026, he serves as a director at Jack in the Box, chairing its Capital Allocation Committee following a late 2025 appointment. A dedicated value investor and philanthropist, he has committed 90% of his estate to charity and is a vocal advocate for immigration reform, famously hosting mass naturalization ceremonies at Dodger Stadium. He remains a key figure in sports business, previously partnering with Phil Knight on a $2 billion bid for the Portland Trail Blazers.

Todd Wagner is a billionaire entrepreneur and co-founder of Broadcast.com, which he famously sold to Yahoo! for $5.7 billion. As CEO of 2929 Entertainment, he pioneered vertically integrated media and day-and-date film releases. In 2026, his focus centers on "venture philanthropy" through the Todd Wagner Foundation and the Charity Network, a digital platform modernizing global fundraising. He recently launched FoodFight USA, a nonprofit using AI to reform the American food supply and promote regenerative agriculture. Formerly a partial owner of the Dallas Mavericks, he now invests in emerging technologies and sports like Major League Pickleball with the Dallas Flash.

Todd McKinnon is the billionaire co-founder and CEO of Okta, the leading identity provider he launched in 2009. A former Salesforce engineering lead, he has guided Okta through the rise of cloud and mobile, positioning identity as the primary security perimeter. In 2026, he is spearheading "Agentic AI" security initiatives and the "Secure Identity Commitment," a plan to harden global infrastructure against identity attacks. He recently pledged $50 million through Okta for Good to support nonprofit cybersecurity and workforce development. Known for his "truth is your friend" leadership, he argues that AI will actually increase the demand for software engineers by automating rote tasks.

Todd Boehly is the billionaire co-founder and CEO of Eldridge Industries, a holding company with massive stakes in sports, media, and finance. As chairman of Chelsea FC, he oversaw a 2026 coaching shift by appointing Liam Rosenior. His sports portfolio includes the Los Angeles Dodgers, Lakers, and Sparks. Beyond the stadium, he is Chairman of Penske Media—owner of Variety and Rolling Stone—and recently launched a $70 billion asset manager, Eldridge. A dedicated philanthropist, he supports healthcare and education via the Boehly Center at William & Mary. By early 2026, his net worth reached $9.3 billion, driven by aggressive expansion in the insurance and entertainment sectors.

Timothy Springer is the Latham Family Professor at Harvard Medical School and a billionaire biotech pioneer known for his foundational work in immunology. He discovered the first integrins and adhesion molecules (ICAMs), discoveries that led to blockbusters like Entyvio and Raptiva. A founding investor in Moderna, he famously turned a $5 million stake into billions, cementing his status as one of the world's wealthiest academics. In 2026, he continues to lead the Institute for Protein Innovation (IPI), a legacy nonprofit he endowed with $210 million to advance open-source protein research. Recently, he was elected a Fellow of the National Academy of Inventors and made headlines for his massive $61 million investment in Tectonic Therapeutic. Beyond science, he is an avid collector of gongshi (Chinese scholar's rocks).