On a Thursday afternoon in late spring, 32-year-old Glossier founder and CEO Emily Weiss rides the elevator to the penthouse level of her company's downtown Manhattan headquarters. She's a thoroughly millennial girlboss in jeans, sneakers and a royal blue sweatshirt with weiss embroidered in small white script. Her hair is pulled back in a ponytail, and for the founder of a beauty products company, she wears notably little makeup - just some mascara and possibly a swipe of Glossier Lip Gloss, a recent product release touted online as having a "fuzzy doe-foot applicator."

A former teen model, Weiss is beautiful but not intimidating, either by nature or by design (probably a little of both). After all, her company’s popularity is directly related to her ability to cultivate a feeling of friendship with and among her customers. Just enough relatability is key.

It’s 1 pm on a Thursday, and Bobby Flay is sitting in his favorite spot to conduct daily business: the corner banquette in the front window at Gato, the Lower Manhattan outpost of his fine-dining empire. He is dressed casually in a dark-blue henley and jeans, wrapping up a call as his team gets situated around him for the first agenda item of the day: testing 10 new cocktails.

Marlene is the new bar manager, and this is her first time pitching the boss her own concoctions. She’s a bit nervous, but she’s done her homework. And Flay is impressed, on the whole, with her creations. But he zeroes in on one drink in particular. “You know what the surprising flavor in here is,” he tells her with genuine admiration, “and not everyone’s going to pick up on this -- it’s the pink peppercorn.” But after a further moment’s reflection, the garnish in Marlene’s drink gives him pause.

After 30-plus years running a kitchen, opening dozens of successful upscale and fast-casual restaurants employing, at present, more than 1,000 people and managing a widening universe of side projects, TV shows and product lines, the 52-year-old Flay is cocksure and precise in his knowledge of what will and will not go over with the customer, and he shares that knowledge freely with his staffers.

Jeff Bezos started Amazon 23 years ago as an online bookstore. Today it has grown into the largest internet retailer in the world; it’s home to an Oscar- and Emmy-winning production studio; its subscription service, Amazon Prime, reached 80 million members this year (up from 58 million in 2016); and it’s made Bezos one of the richest men on the planet.

This success alone -- to see opportunities where others haven’t, and move into them faster than others can -- would make him a daring entrepreneur. But alongside that, Bezos has proven himself adept at taking on totally unexpected challenges.

Jeff Bezos started Amazon 23 years ago as an online bookstore. Today it has grown into the largest internet retailer in the world; it’s home to an Oscar- and Emmy-winning production studio; its subscription service, Amazon Prime, reached 80 million members this year (up from 58 million in 2016); and it’s made Bezos one of the richest men on the planet.

This success alone -- to see opportunities where others haven’t, and move into them faster than others can -- would make him a daring entrepreneur. But alongside that, Bezos has proven himself adept at taking on totally unexpected challenges.