Ryan Cohen, entrepreneur and activist investor, is best known for founding Chewy and for leading the shareholder-driven transformation of GameStop. After selling Chewy to PetSmart, Cohen took a major stake in GameStop and became chairman, pushing the company to reinvent itself from a declining brick-and-mortar retailer into a more technology-oriented business. Known for intense customer focus, contrarian thinking, and a preference for operating with minimal public commentary, he has become a central figure in modern retail disruption and meme-stock era corporate activism.

Pierre Omidyar, founder of eBay, created one of the internet’s earliest and most enduring marketplaces by enabling peer-to-peer commerce at global scale. Launching eBay in 1995, Omidyar built trust mechanisms and open access that allowed millions of individuals and small businesses to transact online, helping define modern e-commerce. After stepping back from day-to-day operations, he focused on impact investing and philanthropy through the Omidyar Network, backing initiatives in financial inclusion, governance, journalism, and technology for social good.

Peter Szulczewski, founder and former CEO of Wish, built one of the world’s largest mobile-first e-commerce platforms by reimagining online shopping around price discovery and global supply chains. A former Google engineer, Szulczewski launched Wish to connect value-seeking consumers directly with manufacturers, prioritizing personalization, scale, and mobile engagement over traditional retail norms. Under his leadership, Wish grew rapidly worldwide and went public, becoming a defining—if unconventional—player in cross-border e-commerce. His career reflects a willingness to challenge entrenched retail models through engineering-led experimentation.

Niraj Shah, cofounder and CEO of Wayfair, helped build one of the world’s largest online home-goods retailers by reimagining how furniture and décor are discovered, sold, and delivered at scale. Starting the business in 2002 as a collection of niche e-commerce sites, Shah guided Wayfair’s evolution into a vertically integrated platform spanning logistics, private labels, and global sourcing. Known for data-driven execution and long-term conviction, he has steered the company through rapid growth, a public listing, and the complexities of last-mile fulfillment in bulky goods, reshaping e-commerce for the home category.

Ernest C. “Ernie” Garcia, III is the American tech‑entrepreneurial executive behind Carvana, the disruptive used‑car retail marketplace he co‑founded in 2012. A Stanford alumnus in Management Science & Engineering, he previously worked at DriveTime and RBS Greenwich Capital. Under his leadership, Carvana went public in 2017 and became a Fortune 500 company. Despite market volatility, Garcia continues to steer its turnaround as CEO and Chairman.

Ernest García II is a self-made billionaire automotive entrepreneur and investor. After a criminal conviction in 1990 tied to the Lincoln Savings & Loan collapse, he rebuilt his fortune by acquiring and scaling DriveTime Automotive Group—a used‑car sales and financing company targeting subprime customers. He also remains the largest individual shareholder of Carvana, the online used‑car platform founded by his son, Ernest Garcia III. As of early 2025, García’s net worth is estimated at around $16–21 billion.

Anthony Casalena is the founder, CEO, and driving force behind Squarespace—a web‑building pioneer he launched from his University of Maryland dorm room in 2003. Over two decades, he transformed the platform into a billion‑dollar SaaS powerhouse used by millions, navigating a public listing in 2021 and steering the company again through a $6.6 billion take‑private deal in 2024.

Eric Smidt is the CEO and co-founder of Harbor Freight Tools, a privately held tool and equipment retailer with over 1,200 locations across the United States. Known for his keen business acumen, Smidt transformed Harbor Freight from a small mail-order business into a retail giant. He is also a notable philanthropist, with significant contributions to education and healthcare.