Ritesh Agarwal — Indian Teen to OYO Billionaire at 26

Dropping out of college at 17, he joined the Thiel Fellowship and founded OYO Rooms, a budget hotel aggregator that expanded to 80+ countries with 157,000+ hotels, backed by a $1.5 billion SoftBank investment that pushed valuation to $10 billion. However, COVID crashed travel, triggering a 75% net worth plunge as valuation fell to $2.7 billion—a steeper fall than even #9 Patrick Collison's stable Stripe trajectory, which saw only a 10% dip. Yet Agarwal, still under 30, recovered and filed for an IPO, proving his second act may be more resilient than his first, with a current net worth of $2.3 billion.