Threadless co-founders Jake Nickell and Jeffrey Kalmikoff are radically reinventing what it means to run a consumer-products company. Their Chicago-based T-shirt business is built on the desires and designs of the site’s social community. Users upload designs and vote on their favorites, and then Threadless puts them into production. The business grosses $30 million a year and enjoys profit margins of 30 percent. So who advises Nickell and Kalmikoff on strategy? Besides their venture capital backers, Kalmikoff’s father is another key influence. “He’s more of a traditional businessman,” Kalmikoff explains. “Talking to him makes clear how unconventional our ideas can be and how to scale them back without compromising too much.”
Nolan Bushnell founded Atari and Chuck E. Cheese’s and, once upon a time, gave Steve Jobs a job. Today, he’s looking to get back into the entrepreneurial big leagues with a restaurant company. His wife, Nancy, and daughter, Alissa, are two of his key advisors. “Nancy can ferret out frauds and phonies better than anybody else I’ve ever seen,” Bushnell says.
Jack Taylor founded Enterprise Rent-a-Car in 1957, and built it into a multi-billion-dollar company. He passed the CEO’s job to his son Andy in 1991, and the chairmanship of the board in 2001. Today, father and son still speak every day about the challenges the business faces, including how to limit the company’s carbon footprint. Andy, who wanted to foster a new spirit of corporate social responsibility at the company, came at the problem as a CEO; Jack, who has donated millions to the Missouri Botanical Garden, approached as a man interested in creating a legacy. Together, they put Enterprise on the path to building the world’s largest fleet of hybrid vehicles. “He’s been asking the same questions about our business for 50 years,” says Andy of his dad. “Are our customers satisfied? Are our employees having fun? Are we doing things the right way?”
Selena Cuffe met her husband, Khary, at Harvard Business School. Today, she runs Heritage Link Brands, an American distributor of wines grown in Africa by African winemakers. Khary is the company’s chief financial officer, and Selena confers with him constantly. “He is the voice of reason,” she explains. “I’m the up, up, positive, happy person. He’s the one who gives you the worst-case scenario, so we are always pushing the envelope in terms of the finished product.
Elon Musk is the CEO of two businesses: Tesla Motors, an upstart electric-car company, and Space X, a private rocket company. When Musk was 13, he and his younger brother Kimbal hatched a scheme to open an arcade near their school, which was foiled only when a city official informed them they would need an adult’s permission. Kimbal still serves as Musk’s sounding board. “Sometimes I want things to be true, even though they're not, and Kimbal is good at pointing those out,” Musk says.