340. Alan Trefler
$2.4 billion Self-made Score: * Source: software age: 61 residence: brookline, mass. B.S., dartmouth ’77
the chess whiz earned a master rating while at dartmouth and became cochampion of the 1975 world open chess championship. trefler started customer-engagement software firm pegasystems in 1983 using $500,000—a mix of an inheritance and loans. he debuted on the forbes 400 in 1997 with a net worth of $650 million and returns after a 2-decade absence, thanks to pegasystems’ soaring stock as revenues from cloud services increased.