We've all had them—bosses with outrageous demands and obnoxious habits. To commemorate this Hallmark holiday (and as an exercise in schadenfreude), we spoke to five execs who have paid their dues by babysitting unruly kids and tracking down yodelers. Here, the hijinks they lived through on their way to the top.
Long before she launched Nestio, which aims to make apartment hunting headache-free, Maio's first job was as a towel folder at a New Jersey beach club, which quickly became a nightmare when she was told to babysit the three rowdy children of a prominent patron. "The youngest went to the bathroom on several of the towels," she says. "And my boss insisted that I salvage them!"
Most people in a microbiology lab teeming with volatile chemicals like tritium and chloroform cover their feet in shoes and their shoes in booties. Not Flora's first boss—he wore only socks, much to the chagrin of his lab mates. "His feet smelled like halitosis mixed with a sickly sweet chemical smell," says Flora, who now heads the wall-graphic company Blik. "I thought I might pass out from the aroma."
CEO, Rosetta Stone
As a commodities merchant in Switzerland, Adams had a boss who went above and beyond to impress big clients from the former Soviet Union. Adams was charged with securing entertainment—that is, finding and hiring professional yodelers. "I can't tell you how many times I've had to listen to yodelers sing 'Edelweiss' from The Sound of Music."
Founder, Dogfish Head Craft Brewery
While studying abroad in Sydney, Calagione, then 21, worked at a bar where his boss gave employees a beer after each shift. The catch? There were just two serving-size options: a measly pint or a 2-liter glass in the shape of a German military boot, which Calagione chose on more than one occasion. "I'd wake up the next morning with major regrets."
Cofounder, Gilt Groupe
While working at eBay, Maybank's boss sent her to rep the company at a motorcycle rally in South Dakota's Badlands. The term "culture shock" only begins to describe her experience. "Everywhere were guys on Harleys with huge fur hats, covered in tattoos," says Maybank, who found the crowd to be surprisingly friendly. "Some said, 'Hey, can I give you a hug? I love that site!'"
A version of this article appeared in the October 2011 issue of Fast Company magazine.