Rent a Shack with Bert Jacobs
Credit: Douglas Mason / Getty Images

Bert Jacobs, founder and CEO of Life Is Good

"My gig in the summer is that I rent a little shack on the south side of Nantucket. The stereotype of Nantucket is that it's pretentious. One time in high school, I went there to play a basketball game. I saw the people – with their matching sweaters – and thought I'd never go back. But back in 1995, just when we were getting our business going, someone introduced us to Packy Norton, who owns the Chicken Box – the only dive bar on Nantucket that has live music. He liked our t-shirts and wanted us to make him a logo.

So we made this logo of a chicken doing a peace sign. He loved it, and invited us over for a weekend. I thought, 'Shit, now we have to go to Nantucket.' But he introduced us to so many down-to-earth people. We played wiffle-ball on the beach, listened to the Red Sox, then we'd head to Chicken Box, and all these girls in bikinis would be coming off the beach. At night, we'd hear live music. I've been going back ever since."