David Sacks is a South African-born Silicon Valley operator turned venture capitalist and political power broker. He was PayPal's first product leader and COO, founded and sold Yammer to Microsoft for $1.2 billion, rescued Zenefits as interim CEO, and co-founded Craft Ventures, which manages billions in assets. He is a co-host of the chart-topping All-In podcast and served as the first White House AI and Crypto Czar in the second Trump administration before stepping aside in March 2026.
Parker Conrad is the co-founder and CEO of Rippling, a $16.8B HR and IT platform revolutionizing enterprise software. After being forced to resign from Zenefits in 2016 amid compliance scandals, he staged one of Silicon Valley's most dramatic comebacks, building Rippling into a unicorn that surpassed his previous company's peak valuation. Worth $2.3B, Conrad pioneered the controversial 'compound startup' philosophy - building multiple products in parallel rather than focusing narrowly - and is known for his impatient drive, contrarian thinking, and obsession with detail. From studying sea snail brains as a teenager to running payroll for 5,000 employees, he embodies the resilient, ambitious founder archetype.