Kevin Plank, founder and executive chairman of Under Armour, transformed an idea born from sweat-soaked T-shirts into a global performance apparel brand that redefined athletic wear. Launching Under Armour in 1996 from his grandmother’s basement, he introduced moisture-wicking compression gear to football teams and quickly expanded the brand across professional sports, retail, and international markets. Plank led Under Armour through explosive growth, celebrity partnerships, and a high-profile IPO, while cultivating a bold, challenger culture. After stepping back from the CEO role, he remains the company’s strategic force and a major investor in real estate and hospitality through Sagamore Ventures.

J. Christopher “Chris” Reyes is the American billionaire co‑chair and elder founding brother of Reyes Holdings, a $40 billion family-run food and beverage distribution giant. He teamed with his brother Jude to grow a single Schlitz beer distributor in 1976 into the country’s largest McDonald’s and beverage logistics provider.

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.