Allison Evanow was sleeping one summer night when it hit her. She woke up next morning, turned to her husband and said, “I have this crazy idea.” Already working in the spirits industry, Evanow had noticed a “sophisticated and energized cocktail movement” ...

One principle of commando business operations: Repeat your successes. Restaurant chains are good at replication.

The chief purveyor of hip-hop culture saw opportunity everywhere, even in the earliest days of rap. “You’d be happy to work with somebody,” he says, “but nobody wanted to work with you.” Since then, Simmons has made millions launching businesses nobody else believed in across media, fashion and banking, all catering to an underserved market.

Joe Coulombe still has his fingerprints all over Trader Joe’s. Founder of the food store that bears his name, Coulombe is responsible for the good selection of dried fruits and nuts, as well as the Hawaiian shirts employees wear. Other trademarks are less visible.