The Entrepreneurs of the Decade: 2000 to 2009

Yes, we know it's a predictable choice. But when you think about the iPod, the iPhone, iTunes, and the App Store, you realize that any one of these breakthrough ideas would be enough to propel an entrepreneur onto a list of the decade’s top achievers. The fact that Jobs led the company that developed all of them—and built the nation’s coolest retail outfit in his spare time—is truly remarkable.

He built the first great brand of the Internet era and set the standards by which other online retailers are measured. Then he guided his company to profitability, a feat some doubted was possible. And as if to say that pioneering e-commerce was not enough of a legacy for either himself or for Amazon, Jeff Bezos set his sights on changing the very way that we read, by developing the Kindle.

If the great story of the decade is the rise of Chinese capitalism--and the opportunities and perils that China's economic power presents for American businesses--then Jack Ma is a protagonist for our age. Alibaba.com, the company he started in China in 1999, helps to connect thousands of businesses at every point in the global supply chain with one another. In all of these small transactions, Ma seems something quite huge. “I want to create one million jobs, change China's social and economic environment, and make it the largest Internet market in the world,” he told Inc. in 2008.

She’s more emblematic of the 1990s than of the 2000s, but remember this: Martha Stewart bet that by not appealing her conviction (for lying to prosecutors, in case you forgot) and by simply getting her five-month prison stretch done with in March 2005, she would minimize the damage to her reputation and quickly get her company back on track. It was a hell of a decision, and it paid off.

Following a series of strategic acquisitions in the 1990s, Mackey led his supermarket chain back to a strategy of—wait for it—organic growth, opening 145 stores worldwide between 2000 and 2009. Critics may complain that the company has strayed far from its wholesome roots but, without Whole Foods, it's hard to imagine many of the decades trends in food, from sustainable fishing to artisanal cheese, taking off as they have. And even as the recession has tightened consumers' budgets, Mackey has led the company to steady revenue growth while avoiding layoffs. So what if he sometimes likes to post things on the Internet?

The award for taking a dead company and breathing new life into it goes to Leslie Blodgett, the CEO of Bare Escentuals. When she took over the mineral-based cosmetics company, it had recently been bought out of foreclosure by a venture capital firm for $160,000. She re-branded the makeup line and added lipsticks and eyeshadow. Then, with no prior TV experience, Blodgett went on QVC and booked $40,000 in sales in just six minutes. “When people ask me what are the best moments of my life, that has to be one of them," she told Inc. in 2008. Her company, which went public in 2006, is now on track to gross $500 million a year.

He smartly placed his company at the nexus of two of the most important technology trends of the decade: The widespread adoption of customer relationship management systems and the advent of cloud computing. The strategy turned the software world on its head, and propelled Salesforce.com to a strong, post-Sarbanes-Oxley IPO in 2004. With funding in place, the company took off, joining the S&P 500 a few years later and crossing the billion-dollar mark in terms of annual revenue in 2008. Bonus points: In the branding-challenged world of business-to-business software, Benioff’s selection of a memorable domain name stands out.

We don't have much more to say than this: When the decade started, he was 15. Today, he is CEO of Facebook, a company that has become an indispensable part of the lives of 350 million users worldwide. And just wait for that IPO.

In July, Hsieh sold Zappos, his online shoe retail company, for $1 billion--at a time when his annual operating income was just north of $20 million and business valuations were generally terrible. But the size of the multiple is almost beside the point. The culture of Zappos has become something of a religion for entrepreneurs. They eagerly study Hsieh's philosophy of customer service. They copy his techniques for interviewing and hiring employees. They brag about exchanging e-mails and tweets with him, and they trade stories about the time they were in Vegas and went on the Zappos tour. As the decade draws to a close, there is no single entrepreneur who is a faster-rising star than Tony Hseih.

He is best known now for the many businesses he’s invested in, including Facebook, Yelp, and LinkedIn. But we haven’t forgotten that, early in this decade, Theil along with Max Levchin and Elon Musk developed and sold PayPal. The simple, secure online payment system (which is taken for granted today) was not only a great business in its own right; it made e-commerce feasible for hundreds of thousands of start-ups and solo entrepreneurs.

Reed Hastings has weathered more than his fair share of highs (10 million subscribers; Born into Brothels; those smart red envelopes; the million-dollar Netflix prize) and lows (a class-action lawsuit over the phrase "unlimited rentals"; aggressive competition from Wal-Mart and Blockbuster Video; the fact that Netflix's most avid customers are also its least profitable.) Handling each new challenge with aplomb, Hastings has demonstrated an enviable capacity for resilience. “Being an entrepreneur is about patience and persistence, not the quick buck,” he told Inc. in 2006, “and everything great is hard and takes a long time.”

Though David Neeleman’s board of directors grounded him not long after his upstart airline, JetBlue, experienced a major customer service breakdown, he remains one of the decade’s most respected entrepreneurs. By building a fresh, new brand in a struggling industry—complete with individual seat-back TVs and tasty blue corn chips—he showed start-ups everywhere the value of taking on entrenched players with creativity and style. Moreover, by speaking openly and candidly about his ouster, he has helped to take (some of) the stigma out of entrepreneurial failure.

“I'd rather be wrong and thriving than right and dead,” the founder of Gawker Media wrote on his blog in July 2009. He was referring to a prediction he had made nine months earlier that, before the recession was over, media companies would experience a decline in advertising revenue of as much as 40 percent. So Denton promptly (and rather dispassionately) shut down several underperforming sites and trimmed his staff. The moves seem to have paid off, assuming Gawker's revenue closely tracks its surging Web traffic. But we're not adding Denton to this list because his business is doing well. We like him for those matter-of-fact, I-told-you-so blog posts and memos. Many, many entrepreneurs believe they can see farther down the road than the rest of us (and many of them can). It's fun to see one of them document what that feels like.

Beginning with the launch of a flagship Manhattan store in March of 2000, the chairman of H&M embarked on a decade of rapid international expansion en route to an $18 billion fortune. His company combined a flair for PR (Karl Lagerfeld, Stella McCartney, and Sonia Rykiel) with an innovative business model (low margins, high volumes, and fast inventory turns). Plus, we're suckers for a family business saga that turns out well: Persson, who inherited H&M from his father in 1989, turned over the reins to his son, Karl-Johan, earlier this year.

Like Cher or Prince (but with flashy punctuation), @Ev and @Biz have become household names by creating Twitter, the addictive microblogging platform that is already changing the way we communicate. Besides fostering a collective penchant for brevity, the site has become an amazing resource for everyone from marketers in Silicon Valley to democratic activists in Tehran. If you’re not keeping an eye on the day’s trending topics, you’re hopelessly misinformed.

Few books this decade were as significant as Thomas Friedman’s The World is Flat, the title of which was inspired by the Indian billionaire Nandan Nilekani. Nilekani, who was then serving as CEO of Infosys Technologies, one of the world’s top outsourcing companies, told Friedman in an interview that technology and globalization allowed companies in places like India and China to “level the playing field” of international commerce. The phrase stuck in Friedman’s head and, with a little tweaking, became a full-blown mantra. But don’t think of Nilekani as merely a literary footnote: Through his work as head of India’s National Association of Software and Service Companies, he is promulgating the virtues of entrepreneurship to a nation that is eager to get down to business.

In retrospect, Google’s success seems foreordained. But at the beginning of the decade is wasn’t at all clear that the search company—founded by two young Stanford grad students—was going to sail through the dot-com bust, put together a blockbuster IPO, rewrite the rules of advertising, and then follow all of that up by diving into businesses ranging from satellite mapping to viral video to e-mail. But as with all things related to Google, the sum seems to be so much larger than the total of its parts. As the journalist John Battelle wrote in his book The Search, entrepreneurs Brin and Page have, in just 10 years, "fundamentally changed the relationship between humanity and knowledge."