Martha Stewart

She’s been a fashion model, a stockbroker and a convicted felon; she’s also a self-made billionaire whose empire extends from McMansions to meal kits. Martha Stewart, or M. Diddy, as she was known in jail, is both an iconic brand and a very funny, very frank woman who is fully aware of her own over-the-top reputation.

In the 1990s, she became known as the queen of decoupage and decorative gourds—a woman who was able to maintain a straight face while instructing her audience on the art of massaging dollops of yogurt into terra-cotta pots in order to cultivate the perfect mold-speckled effect. During her five-month stint behind bars for insider trading in 2004-5, she apparently taught her fellow inmates how to make crabapple jelly. But over the past couple of years, Stewart has begu...