Kesi Irvin's summer side hustle has taken her across the world. The New Jersey native is paid to sample gelato in Italy, jet ski in the Mediterranean and walk through open-air markets in Croatia.

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Jimmy John Liautaud, the billionaire proprietor of the sandwich chain Jimmy John’s and a serial yacht owner, is also a serial workaholic. “When I’m on my boat, I work on my boat. When I’m on my plane, ...