Adam Neumann — WeWork ($1.7 Billion Exit)

Adam Neumann's $1.7 billion exit package is the largest single payout for failure in startup history. The package included a $185 million consulting fee and $500 million loan to Neumann personally, even as WeWork lost $1.25 billion in 2019 under his leadership. This payout was 50% higher than Bob Iger's entire Disney tenure earnings (#5) and came after Neumann's aggressive expansion drove the company to the brink of collapse. SoftBank's desperation to avoid a total write-down explains the generosity: they paid Neumann 15 times the value of his remaining shares to step away. The $1.7 billion figure represents 14% of WeWork's total valuation at the time, making it the most expensive founder exit relative to company size ever recorded.