Guresh "Desh" Deshpande's House

Deshpande he started Cascade Communications with $1,000 and sold it for $3.7 billion, then founded Sycamore Networks, which boasted the fourth-largest IPO of all time. Those successes pushed his net worth to a peak of $13 billion, making him the wealthiest Indian on earth. Sycamore's share price has since plummeted from a high of about $200 to less than $5, and Deshpande and his CEO, Dan Smith (No. 38), are stuck with 32 percent of the stock.

In 2006 he was ranked the 34th richest Bostonian worth $412 million.