The Secret of Their Sucess

Nov. 12, 2007 — -- With his thick-rimmed glasses and goofy demeanor, Drew Carey doesn't fit the stereotypical image of a winner. But with two hit TV shows under his belt and a new gig hosting "The Price Is Right," Carey reminds us that even average Joes can hit it big in Hollywood by just being themselves.

Success didn't come easy to Carey. A self-described "loser" in his teen years, Carey battled depression from an early age. "Back then, I was so full of a lot of self-hate," he says. "Man, I just didn't like myself."

Bulking up in the Marine Corps Reserve helped Carey gain some of the confidence he needed, but things really started to look up when he got a job writing jokes for a friend who worked in radio.

It wasn't long before he became a regular on the Cleveland comedy circuit, and soon after that, came his career's turning point: a shot on the "Tonight Show Starring Johnny Carson." After Carey's performance there, Carson called him "funny as hell," and the rest, as they say, is history.

Though he's now an iconic comedian and an established TV star, Carey doesn't like to think of himself as a "winner." Calling yourself a winner when things are going well, Carey says, implies that you're a loser when things aren't going so well.

As Carey learned while overcoming his depression, comparing yourself to others and striving to be a "winner" won't make you happy. "It's all about love and kindness," Carey tells "20/20." "Not about comparing yourself to anyone else."

Also on the show, meet some amazing young people who have gone beyond expectations, and reached huge goals at an early age.

Find out what inspired young entrepreneurs like Ephren Taylor, who started his first company when he was only 12 years old, and, at 25, is now the youngest black CEO of a public company.

We'll also hear from Catherine Cook, a Georgetown University freshman, who started MyYearbook.com at age 17, and Ben Casnocha, the author of "My Start Up Life," who at the age of 14 founded a company that now earns almost $1 million a year. Casnocha travels the country speaking with executives and young people — and he hasn't even started college yet.

What's the secret of these young entrepreneurs' success? And is there a negative side to success at such a young age?

Some successful adults say it was their early failures, not successes, that shaped their lives. "Failure is nothing more than life's way of nudging you and letting you know that you're a little bit off course," said entrepreneur Sara Blakely, the creator of Spanx, a line of women's undergarments that smooths over panty lines and slims down unsightly bulges.

Seven years ago, Blakely turned her $5,000 in savings into a formidable apparel company with $150 million in retail sales, and countless celebrity clients, but the company actually grew out of failure.

Blakely wanted to be a lawyer, but she flunked her law school entrance exam. Instead of letting that failure deflate her hopes and dreams, however, she decided to see it as an opportunity to switch gears. "Spanx would not exist if I had not failed the LSAT," Blakely said.

Blakely credits her father with teaching her to not be afraid of failure. When she was young, she says, her dad pushed her and her siblings to purposely try things they would not be good at, making her less fearful of leaving her comfort zone.

And that's a good lesson to learn, according to Elaine Eisenman, dean of executive education at Babson College. "Entrepreneurship is a continuum over a lifetime of different opportunities. So, when you look at it as a series of milestones over the course of time, failure doesn't take on such an important piece. It's just something that happens," she said.

For Jake Burton, failure was something that happened early and often. He walked away from a lucrative job in mergers and acquisitions, and moved to Vermont to make and sell snowboards. That was in 1977, when snowboarding was still known as "snurfing" (for snow surfing), and was banned from most ski resorts.

Despite the odds, and without any manufacturing experience, Burton poured his inheritance into his new company, Burton Snowboards. Predictably, his startup floundered.

"I can remember once going out with 25 boards and hitting a bunch of shops," Burton said. "One shop was a shop I'd already sold boards to, and they didn't want them. They wanted me to take them back. So, I came home with 27."

Burton burned through his seed money quickly, and was forced to be a bartender and teach tennis to make ends meet. But then it hit him: There was no snowboarding market. If his company was to survive, the sport had to take off first. So, he lobbied resorts to open their slopes to snowboarding, and encouraged people to take up the sport.

"Once I focused on that, and really looked out for the sport, everything just took care of itself," Burton said. "The business started to take off. We started making money. Everything started to happen."

Now, Burton Snowboards is the undisputed king of the snowboarding mountain, with an estimated 35 percent market share. Shaun "Flying Tomato" White and other elite snowboarders are fiercely devoted to the brand. And Burton continues to look back on those lean early years with pride; he would not be the businessman he is today had he not made — and learned from — his early mistakes.

Plus, for centuries, the United States has been the land of opportunity for immigrants, and many entrepreneurs from around the world still live out their American dreams.

Some immigrant entrepreneurs say their stories of success could only have happened in America. Tom Szaky was born in Hungary and raised in Canada. The 25-year-old came to the states for college, and founded Terracycle, a company that creates garden products entirely from waste.

"I think America, by far, is one of the best countries for people to come here as an immigrant, especially as an entrepreneur," he said. "America's built on the idea of entrepreneurship."

Some success stories may happen only in America, but some of the wealthiest Americans seem to live in an entirely different world.

Imagine a place full of private jets, giant yachts and larger-than-life mansions. At the snap of your fingers, everyone from butlers to world-class chefs can be at your service. This is the world of truly wealthy Americans whose lifestyle is so different from the rest of ours, that it is as if they live in their own country — a place author Robert Frank calls Richistan.

"This is really a world unlike the world that you and I live in," said Frank. And the population is exploding. At the moment, it's 9 million strong.

"Never before in American history," said Frank, "have so many Americans become so wealthy, so quickly." In the last 10 years, the number of U.S. households making $10 million, $20 million or $50 million have all doubled. They are a different kind of wildly well-to-do, because these winners didn't inherit their wealth — they earned it by working hard to make it on their own.

Billionaire Tim Blixseth of Oregon made his money in timber and real estate. He owns multiple jets, yachts and vacation properties, but is rarely relaxing in one place for long. He is what Frank would call a "workaholic wealthy," for whom success is never enough, and who is always on the lookout for a new venture.

And then there are other Richistanis that keep up their public persona by attending never-ending A-list parties, like George Cloutier. A dedicated socialite in Palm Beach, Fla., Cloutier knows how to throw and attend upper-crust elite balls and galas.

These people are the nouveau riche: winners living the American dream, and enjoying their self-made wealth in their own unique ways.

Watch "Winning," Friday on "20/20" at 10 p.m. EDT, for these stories and much more on the secrets to success.