Starting a business is like any other beginning: The first task is survival. But even in those early days, what founder doesn’t dream of doing something really huge--like building a business that rapidly remakes a fusty sector, as Warby Parker’s Neil Blumenthal has, or seizing an early opportunity to dominate an industry, the way Whole Foods’ John Mackey has? The entrepreneurs who fulfill such dreams are the ones we call icons, and we know them when we see them: Barbara Corcoran slyly grilling a supplicant on the hit show Shark Tank, for instance, or Shake Shack founder Danny Meyer, as he succeeds on his mission to boldly transform American dining. How does one proceed from frantic founder to ultra-successful entrepreneur? We’ve taken a close look at four icons to find out.

“You gotta catch the wave,” says John Mackey of Whole Foods. “If there’s no wave, you can’t surf.”

An Early Education

Before there was Whole Foods, there was Safer Way, John Mackey’s first attempt, in 1978, to catch the wave. Safer Way, a natural-foods store in Austin, didn’t sell products containing sugar, caffeine, alcohol, or white flour--and in one year, Mackey lost half the $45,000 he had raised from family and friends. He learned a critical lesson. “If your philosophy is too Puritan,” he says, “you can’t do enough business to be successful.”

Safer Way merged with Clarksville Natural Grocery, moved to a larger location, and changed its name to Whole Foods. “We decided we were not going to be Holy Foods Market,” Mackey says, “that we were gonna sell foods our generation wanted to buy”--still organic, still no artificial flavorings, colorings, or preservatives, and still focused on health--just not in a “full of judgment” way. 

Family Dynamics

Mackey had a famously fraught relationship with his mother. She asked him, from her deathbed in 1987, to promise he’d go back to college and get his degree. Sorry, not happening. “My mom was not really proud of what I was doing,” Mackey says, “so I wasn’t close to her.”

Things were different with his dad. Bill Mackey was an original investor in Whole Foods, a longtime board member, and a mentor to his son. But after Whole Foods went public, in 1992, and kicked off an era of rapid expansion, the two found themselves embroiled in a classic go-slow-or-grow debate.

“I wanted to build the company,” Mackey says. “We were constantly arguing about whether we should do this store, whether we should make this acquisition. I just found him way too conservative.”

In 1994, as he was turning 40, Mackey asked his father to resign. “The hardest thing I’ve ever done,” Mackey says. “I had to overcome a lot of fear, because I was dependent on my dad, emotionally and intellectually. I knew it hurt him a lot--he felt rejected--so I felt guilty. It was a painful decision, and that pain lasted a while.”

Mackey’s father assented. One year later, he forgave his son.

A Rough Ride on Wall Street

Whole Foods stock has rebounded since last fall, but that follows a dramatic one-year decline amid analysts’ fears: too much competition, from established grocers as well as upstarts; overeager expansion; too many downward revisions of earnings forecasts.

Mackey says he’s unfazed. “The market is manic-depressive. Bipolar,” he says. “It tends to get overly enthusiastic about you at times. Other times, it thinks your whole concept’s doomed, and it bids the stock down. We’ve been public a long time. I’ve seen this before.”

His “Ashram” 

Mackey doesn’t go to church. He doesn’t believe in God, at least “not the way God is usually defined.” But “there’s a deeper spiritual reality that is behind the material reality that most of us can see, touch, and taste,” he says. “The essence of what we are at the deepest level is not our bodies, it’s not our egos. It’s something beyond that, which doesn’t fit well into definitions.” 

He has searched for the meaning of life, and he believes he’s found it. Not in a teacher, a guru, a path, or a book, but in business. “Whole Foods is my ashram,” he says. “Whole Foods is where I’ve learned my great life lessons. It’s full of love, full of creativity, full of compassion and caring. It has a bit of me in it, as well as a bit of everybody else who’s contributed their care and love and creativity.”