When Crain’s 40 Under 40 list debuted in 1989, Oprah Winfrey was riveting talk-show audiences with tabloid topics such as satanic dismemberment.

Marc Schulman, another 1989 honoree, had succeeded his late father at Eli’s Chicago’s Finest Cheesecake Inc., which would make a 2,000-pound cake for President Bill Clinton’s 1993 inauguration.

And Richard M. Daley was beginning his 22-year reign at Chicago’s City Hall with a campaign assist from a young political consultant, David Axelrod, also class of ’89, who would go on to chart Barack Obama’s historic 2008 bid for the White House.

As for Mr. Obama, the Harvard Law School student was then a summer associate at the Chicago office of law firm Sidley Austin LLP, where he met his future wife, Michelle Robinson. He would be named to the 40 list in 1993.

Since Crain’s launched 40 Under 40, its annual feature spotlighting local luminaries under the age of 40, no fewer than 1,000 up-and-comers from every walk of life have won the honor. The oldest among them began their careers when stores meant bricks without clicks, the Soviet Union hadn’t disintegrated and MTV still played music videos. Many, as we knew they would, became leading players in the business, political and cultural dramas that define our times.

 

To be sure, Chicago is home to fewer large corporations now than a quarter century ago, but a glance at the young leaders Crain’s spotlights annually confirms that the local economy remains dynamic and diverse, with a swath of midmarket companies and a startup scene that’s simmering — a Silicon Prairie 2.0.

“The difference between then and now is night and day,” says venture capitalist J.B. Pritzker, 47, class of 2000, who in 1996 raised one of Chicago’s first funds targeting Internet opportunities at Evanston’s New World Ventures. More recently, he organized a tech startup hub in the Merchandise Mart, 1871.

“Years ago, one had to roam around and scrounge to find the tools to build a new technology business in Chicago,” he adds. “Today there are many organizations that provide support and encouragement as well as capital. We now have serial entrepreneurs in Chicago, not two or three but we have dozens and dozens and dozens.”

Among them is Matt Moog, class of ’05, ex-CEO of coupon site CoolSavings Inc., now founder and CEO of consumer review site Viewpoints and founder and chairman of Built in Chicago, an online community for digital entrepreneurs.

 

Cashing in on his success, Michael Ferro Jr., class of ’98, sold software maker Click Commerce Inc. for $292 million in 2006. His current ventures include Wrapports LLC, which acquired with a group of local business leaders Sun-Times Media LLC, publisher of the Chicago Sun-Times.

At age 42, Alex Zoghlin, class of 2000, is chief executive of his seventh startup, Rosemont-based VHT Inc., which provides marketing services for the real estate industry. He was chief technology officer of travel site Orbitz Inc., which its airline founders sold for $1.25 billion in 2004.

Chicago’s highest-profile startup, Groupon Inc., was co-founded by CEO Andrew Mason, 31, class of ’09. Valued at nearly $13 billion when it went public in 2011, the daily-deal site has 12,000 employees in 48 countries. But Groupon’s shares plummeted since the IPO, rattling faith in Mr. Mason’s leadership.

While the tech startup scene emerged in the 1990s, Chicago was losing its biggest financial institutions to bank consolidation. Yet even as money center bankers faded from the local scene, an exploding financial sector and booming stock market opened opportunities in the securities field.

 

Joe Mansueto, 56, class of ’92, harnessed computer databases to analyze mutual fund performance for investors at his 1984 startup, Morningstar Inc. But he would have to wait for a commercial Web browser before his subscribers could read reports online. “We just rode the technology waves from PC to CD-ROM to Internet to mobile,” he says. “Every one of those has been a wave, and trying to figure out how to harness technology for the benefit of investors has been” the company’s challenge.

Today, Morningstar is a $650 million public company with a market cap of nearly $3 billion and 3,600 employees. Mr. Mansueto, chairman and CEO, owns nearly half its shares.

He and other self-made billionaires, such as Citadel LLC founder Ken Griffin, 44, class of ’04, are part of Chicago’s new civic elite. Mr. Griffin launched Citadel in 1990 and grew the hedge-fund and securities business into one of the nation’s largest hedge-fund managers, with about $13 billion in assets under management.

Still other “40s” rode the waves of global consolidation by rising to prominence in corporate settings. Ilene Gordon ran a business line at Packaging Corp. of America when she was named in 1991. “It’s always been my goal to run a major business. But I’m always redefining my definition of ‘major,’” she said then.

Today, Ms. Gordon is chairman, president and CEO of Westchester-based Ingredion Inc., the former Corn Products International Inc., which she catapulted into the ranks of the nation’s biggest companies, with $6.2 billion in sales last year, through growth and a $1.3 billion acquisition. She is one of only 19 women running Fortune 500 companies. About half are mothers.

 

In the political arena, Chicago’s tradition of an iron-willed mayor with national political influence continues under Rahm Emanuel, class of ’90 and Mr. Obama’s former White House chief of staff. Mr. Emanuel is tackling daunting challenges from budget shortfalls to an upsurge in violent crime.

Daniel Hamburger, class of ’99, is one of the business leaders tapped by Mr. Emanuel to reinvigorate boards such as World Business Chicago. The 48-year-old is president and CEO of DeVry Inc., the third-largest private-sector education company with $2 billion in sales, operating in 35 countries. “The outlook for people in business, government and education is increasingly global,” he says.

Few figures have raised Chicago’s profile as much as Mr. Obama, whose posse of Chicago backers includes billionaire businesswoman Penny Pritzker, class of ’91. She raised $745 million as his 2008 national campaign chair.

Ariel Investments LLC founder John Rogers Jr., 54, who co-chaired Mr. Obama’s first inauguration committee, jokes that he became chairman of University of Chicago Laboratory School’s board because Mr. Obama recruited so many board members to Washington. “He ended up taking a lot of talent with him,” Mr. Rogers says.

 

Indeed, the list extends far beyond Messrs. Axelrod and Emanuel. Valerie Jarrett, a city planning commissioner when she was a “40″ in 1994, exerts broad influence as Mr. Obama’s senior adviser. Austan Goolsbee, a star professor at University of Chicago’s Graduate School of Business when picked in 2006, helped craft the administration’s $800 billion stimulus spending plan as chairman of the White House Council of Economic Advisers. He returned to teaching last year.

Arne Duncan, class of ’01, is U.S. secretary of education, and Desiree Rogers, class of ’95, was White House social secretary for two years. She’s now CEO of Johnson Publishing Co., whose majority owner and chairman is Linda Johnson Rice, 53, class of ’89.

“The last five or six years have just been really tough in this country,” says Ms. Rogers, 53. “There’s so much uncertainty about what’s next,” whether globally, in national politics or in the city’s neighborhoods.

MarySue Barrett, 48, Mr. Daley’s policy chief when she was named a “40″ in ’94 and Metropolitan Planning Council’s longtime president, sees a “silver lining” to the economic downturn.

“When things really are tight, there’s a great deal of openness to try new things. But you have to marshal the leadership,” she says.

Given the track record of Crain’s 40 Under 40 honorees, leadership is one element that isn’t in short supply in Chicago.
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