(FORTUNE Magazine) – Last summer Joe Galli played the tug of war between the old economy and the new--and won big. In June, Galli, who had fled Black & Decker after having clashed with CEO Nolan Archibald and lost the No. 2 position, lined up two plum jobs. One was to be CEO of Frito-Lay North America, PepsiCo's most important business. The other was to be Jeff Bezos' president and chief operating officer at Amazon.com. Flirting with Amazon was fun: Galli hung out with Bezos in Seattle and New York City, had breakfast with venture capitalist John Doerr in Silicon Valley, and visited Wall Street's reigning Internet analyst, Morgan Stanley's Mary Meeker. Not surprisingly, all told him the same thing: Go west. Change the world. Meanwhile, PepsiCo CEO Roger Enrico and headhunter Gerry Roche of Heidrick & Struggles were sure he'd come to his senses any day.

Galli did--for a few hours. On June 24, after accepting PepsiCo's offer and signing a blue-chip contract, he did the obligatory meet and greet at Pepsi headquarters. That afternoon he told the press his decision was final. Behind the scenes, though, Galli was a wreck, frantically calling friends and advisers, who told him he should go with his heart. Hours later he did--jilting Enrico and Roche for Bezos. "You have to do what you have to do," says Galli from his new perch at Amazon. "It was a showdown, and there was going to be a winner and a loser. I hope Roger and Gerry forgive me."

Though most manage the move with less opera than Galli, brand-name FORTUNE 500 executives have found the green hills of Seattle and the parking-lot sprawl of Silicon Valley irresistible. Some are hotshots who hit career walls, like Galli. Some have Internet-billionaire envy. Some simply tire of the corporate same-old, same-old. So they opt for the moon-shot into cyberspace.

How does the old gang fare in the new world? In the pages that follow, you'll find a range of execs who have made the leap. A couple have definitely succeeded; two are struggling; most have not been on the job long enough to prove their mettle. One thing's for sure: Internet companies can't get enough of the corporate retreads. A reason is that talent in general is so scarce--"the tightest executive job market ever," says Tom Neff, U.S. chairman of Spencer Stuart, the search firm that delivered Galli to Amazon. The most wanted talent: marketing pros, experts at logistics and distribution, and "magnets" who, by dint of personality and Rolodex, attract more talent and investors.

"A CEO's job is to show people the dream," says Benchmark Capital's David Beirne, who is something of a chameleon himself. As a headhunter, he recruited Jim Barksdale, a veteran of AT&T and FedEx, for Netscape, and P&G's Bob Herbold for Microsoft. Today, as a venture capitalist, Beirne still recruits like mad; he convinced three of the ten people on the following pages--MVP.com's John Costello, Webvan's George Shaheen, and eBay's Brian Swette--to take the Internet leap. To ensure that candidates aren't moving just for the money, Beirne says he refuses to discuss pay until they're on the verge of committing. But he'll gladly show you the dream: "If these guys hit a grand slam, they can make $100 million."

JOHN COSTELLO

Old job: president, AutoNation

New job: CEO and president, MVP.com

Old pay: estimated $1.1 million salary and bonus, plus accumulated options

New pay: est. $200,000, plus more than 5% of MVP.com in stock (est. value: $50 million)

When John Costello was hopping around the FORTUNE 500--from P&G to Pepsi to Nielsen Marketing Research to Sears to AutoNation--who knew he was crafting a resume for the Internet Age? "I had no idea. It was serendipitous," he says. Dot-com startups covet his mix of experience: consumer marketing, information services, and retailing. So when Costello, who led the marketing effort that helped revive Sears a few years ago, hit a speed bump in his next job, at Wayne Huizenga's AutoNation, he headed to Silicon Valley. "The claim that there are hundreds of Internet CEO jobs available is not an exaggeration," he raves. "It's pure capitalism at its best."

The offer he liked most (and what 52-year-old guy wouldn't?) was to be CEO of MVP.com, a sports e-tailing company founded by former Denver Bronco John Elway. Two other restless retirees, Michael Jordan and Wayne Gretzky, are big investors and directors. Their idea is to do for sports retailing what eToys did for toys: Take a lousy business with low margins and dissatisfied shoppers and create an efficient, customer-coddling way of selling. "We want to be the category killer in sporting goods and outdoor equipment," says Elway, MVP's chairman. He met Costello at AutoNation--and sold the company his chain of John Elway auto dealerships for $82.5 million. Elway has put a substantial chunk of his money into his new dot-com.

Fogdog and other sports e-tailers have a head start on MVP.com. But Costello is using old-world connections to propel the company on Internet time. Two months into the job, he realized that MVP.com needed to team up with a traditional media player. So he called an old friend, CBS chief Mel Karmazin. Two days later Costello and Elway were in Karmazin's New York City office negotiating a four-year, $85 million marketing partnership. The Website opens for business the week before the Super Bowl. If Net stocks remain hot, look for an IPO this summer.

BOB BOWMAN

Old job: president, ITT

New job: CEO and president, Outpost.com

Old pay: $1.2 million salary and bonus, plus accumulated options (cashed out at an estimated $35 million)

New pay:* $280,000 salary and bonus, plus 5.1% of Outpost in options (valued at $750,000)

Over lunch in Midtown Manhattan, Bob Bowman tells a story about missing the revolution: It was 1994, and he was CFO of ITT. Captivated by an online company called AOL, he made several trips to northern Virginia to visit Steve Case. They discussed a deal in which ITT would buy 15% of AOL for $100 million. ITT CEO Rand Araskog favored the investment. But when Bowman presented the deal to a roomful of the company's top executives, two shot it down. "They called the Internet 'here today, gone tomorrow,' " he says. The deal died. "It was all my fault," Bowman adds, "I didn't do a persuasive job." That stake would now be worth more than $20 billion.

Four years later, in 1998, when Starwood Hotels acquired ITT, Bowman left with more than $35 million--and an itch to do something really new. He spent 18 months investing in a dozen Internet startups and even created one from scratch: howtoguru.com, a sports-instruction site born of his desire to teach his 5-year-old daughter, Emily, how to swing a racket and a bat.

Last October he took the big leap, signing on as CEO of Outpost.com (formerly Cyberian Outpost). To call the job a challenge would be a serious understatement. Outpost competes in the most cutthroat of e-tail categories, computers and consumer electronics, and the 44-year-old Bowman has never been a retailer. Trying to stand out, Outpost has gone so far as to offer free overnight shipping, even on hefty products like computers. While revenues are up year to year, so are losses, and Outpost's stock has sunk from $39 in late 1998 to $9. That makes Bowman's options almost worthless. No problem, he says: "I've been over my head in every job I've had, and nothing is different today."

Though Bowman has been at Outpost only four months, he has a big plan. He'll keep selling to consumers, he says, but "we're not going to be a one-trick pony." He also wants to sell to businesses and to run online stores for traditional retailers. Business-to-business e-commerce suits his old-economy sensibility: "Whether you're selling hotel rooms or computer equipment, pricing and loyalty are better if you serve business customers."

RICHARD NANULA

Old job: president and COO, Starwood Hotels

New job: chairman and CEO, Broadband Sports

Old pay: $2.35 million in salary and bonus, plus accumulated options (cashed out at $5 million)

New pay: $180,000 plus 9% of Broadband Sports in stock (estimated value: $36 million)

Richard Nanula always seemed like a big-company guy. He gained his first bit of fame as Michael Eisner's prodigy at Disney and became, at 31, the youngest CFO of a FORTUNE 500 company ever. After Disney, he was president of Starwood Hotels, where he was considered the disciplined balance to CEO Barry Sternlicht's mercurial leadership. A top headhunter surmised, "Richard will run a FORTUNE 500 company someday."

But stuff happens. Within a year at Starwood, Nanula's friendship with Sternlicht, his best pal from the Harvard Business School, blew to bits. Nanula exited last April and has not spoken to Sternlicht since. Then, says the 39-year-old Nanula, "I took the summer off. I was exhausted and burned out. I had to put distance between the last experience and my next job."

He rented a house in Malibu, spent time with his 2-year-old twins, and played hard-core hoops at Michael Jordan's basketball camp in Las Vegas (three days for 15 grand). Eventually he got around to rethinking his career. He flirted with Eisner, among other old-world CEOs, "but I had no interest in going back," he says. Then the right match bounced into his court. Broadband Sports, a startup whose investors include Michael Dell and former Viacom CEO Frank Biondi, asked the die-hard sports fanatic whether he'd like to come on as CEO. Unlike John Costello's MVP.com, Broadband is mainly a content company modeled on a Hollywood studio. It operates Websites for star athletes such as Troy Aikman, Kobe Bryant, and Ken Griffey Jr. and delivers analysis--plus streaming-video programming--to serious fans.

The IPO is likely in February. Nanula has a long way to run, but if Broadband scores big, he could end up as what he was always meant to be: a media mogul, albeit for the Internet age.

GEORGE SHAHEEN

Old job: CEO and managing partner, Andersen Consulting

New job: CEO and president, Webvan

Old pay: estimated $4 million salary and bonus

New pay: $750,000 salary and bonus, plus 5% of Webvan in stock and options (valued at $92.3 million)

If you ask George Shaheen why a lifer from the consulting business is the right man to operate an Internet grocer, stand back. "Jesus!" he begins. "I ran a very large, complex business at Andersen Consulting. Sixty-five thousand people! More than a hundred locations around the world! If that's not an operating job, I don't know what is."

Okay, George. Still, a lot of people were stunned last fall when Shaheen, 55, left his prestigious job as CEO of the giant consulting firm to head Webvan, one of the most ambitious dot-com startups. The move makes sense only if you know the many sides of George: Shaheen the entrepreneur, who in a decade pushed Andersen from $1.5 billion in annual revenues to $10 billion; Shaheen the tech aficionado, who lived in Silicon Valley and focused Andersen on building clients' information systems; and Shaheen the iconoclast, who led a civil war against the firm's corporate older sibling, Arthur Andersen. He was managing that dysfunction late last summer when Benchmark venture capitalist David Beirne called about Webvan. "David, you're nuts," Shaheen said, telling Beirne he'd consider a career switch in a year or so. "I told him, 'This opportunity won't exist then,' " says Beirne.

The son of a grocer, Shaheen bagged one of the biggest dot-com pay packages. "I didn't say, 'I want a job where I can make $100 million,' " he says. "But the money made it hard to turn down." Now it's time to deliver. Though Wall Street has turned skeptical--Webvan's stock has fallen from a high of $25 to $13, $2 below its IPO price--Shaheen's ambition is nothing short of out-e-tailing Amazon. Webvan is spending $1 billion to build state-of-the-art distribution centers and delivery systems--a plan even grander than Amazon's. "If you're gonna play," says Shaheen, "you have to step up and play by the rules that we're setting up." By the way, Mr. Bezos, Webvan, too, may sell just about anything on the Web. "We want to be the premier e-tailer," Shaheen says.

JOE GALLI

Old job: executive vice president, Black & Decker

New job: president and COO, Amazon.com

Old pay: $1.6 million salary and bonus, plus options (which turned out to be worthless)

New pay: $3.2 million salary and bonus, plus 1.15% of Amazon in options (valued at $41.3 million)

Why did Joe Galli pass up a big job at PepsiCo, where he would have been a contender to succeed CEO Roger Enrico, for Amazon.com? "If you don't immerse yourself in the middle of the Internet, you're going to be obsolete," Galli says. "I liked the idea of changing the world."

Galli is exactly the type of No. 2 Jeff Bezos wanted: a take-charge, make-it-happen kind of guy. At Black & Decker, the only place the 41-year-old Galli ever worked before Amazon, he steered a professional-tools business from $35 million in annual sales to $1.3 billion in seven years. Much like Bezos, he was absolutely obsessed with knowing and pleasing his customers. Says a Home Depot executive: "Joe knew more about his retail customers than some of them knew about themselves." Wily and kinetic (at the University of North Carolina he was the ACC wrestling champ in the 142-pound class), he's sometimes criticized for being "too driven"--which is the root of his falling-out with his old boss, Nolan Archibald. Now he has linked up with a fellow hard-driving spotlight seeker, Jeff Bezos--this partnership will be a thing to watch.

So far, the match is working. Galli survived both Christmas (working graveyard shifts with other Amazon execs in the warehouses) and e-tailing's post-holiday hangover (Amazon's stock is down 40% since early December). Now he is focusing on the company's expansion into new territory, Europe, and into new markets, including tools. Galli persuaded Bezos to buy a small mail-order tool outfit as a way of launching an assault on the home-improvement category, which is five times the size of the book market. How does expertise in selling books to literate consumers translate into selling tools to rivetheads? Both markets require great back-end logistics to satisfy customers, says Galli, adding with pride, "You can stand on an oil rig off the coast of Louisiana and use your cell phone or Palm VII to order an angle grinder from Amazon.com. And we'll get it to you."

BRIAN SWETTE

Old job: EVP and chief marketing officer, Pepsi-Cola

Old pay: est. $400,000 salary and bonus, plus accumulated options

New job: COO, eBay

New pay: $175,000, plus 1.4% of eBay in stock and options (valued at $242.1 million)

Guess what 162-year-old corporate Goliath turns out to be a prime incubator of tech talent. Would you believe Procter & Gamble? When Brian Swette was a brand manager on Era laundry detergent, his young colleagues in P&G's marketing department included Steve Case, Steve Ballmer, Intuit's Scott Cook, and a woman who, 20 years later, would give him a new outlook on life: Meg Whitman, now CEO of eBay.

"P&G was too confining," says Swette--a perspective that his colleagues apparently shared. Swette (pronounced "sweetie") didn't go on to change the world via software or e-mail as they did. He left P&G to sell pop, at Pepsi. For most of 17 years he thrived, rising from country manager to worldwide marketing chief. Swette became known as an edgy, irreverent marketer, whose role, he says, was "to create change, mix it up."

But when Pepsi's image and market share stumbled, Swette did too. Two years ago, at Pepsi's worldwide bottler meeting in Hawaii, his "Generation Next" TV campaign--including a commercial about body piercing and one that featured a gnat singing the Rolling Stones' "Brown Sugar"--went over with a thud. He left Pepsi four months later.

"I said to myself, 'I need to stay young, stay smart, and reinvent myself a bit,' " says Swette, 45, who hoped to become COO at an established media or tech company. Then he got a phone call about a company he'd never heard of and decided to go meet eBay founder Pierre Omidyar and his new CEO, Meg Whitman. His first encounter with eBay was a happy one, Swette recalls: "My rational mind said, 'This really makes sense.' My emotional gut check said, 'My kids will think this is really cool.' "

Joining shortly before eBay's IPO, Swette got a mass of stock options. They're now worth $242 million. His push-it-to-the-limit style suits the new boss fine. Says Whitman: "Brian tends to lie down on the railroad tracks when he believes in something. I love that. His footprints are all over this place." In November, Whitman gave him his reward: She made him COO.

ELLEN MARRAM

Old job: CEO and president, Tropicana

Old pay: estimated $1 million salary and bonus, plus accumulated options

New job: CEO and president, efdex

New pay: estimated $300,000 salary, plus an equity stake (efdex is privately held and would not disclose details)

Nobody ever had the slightest inkling that Ellen Marram would be CEO of an Internet company. Least of all Ellen Marram.

Her career was strictly old world. As cookie boss at Nabisco, she introduced the low-fat Snackwell's line in 1992. She went on to head Tropicana for its owner, Seagram. But all along, what she really wanted was to run a major independent company. Two years ago, when Seagram planned to spin off the juice business in an IPO, she fully expected she would.

Then PepsiCo--the stealth force in many dot-com job jumps --got in her way. Interested in buying Tropicana from Seagram, PepsiCo set up a meeting with Marram and her team. The day they got together, she put the lid on her beverage career with a single gesture: She drank a diet Coke. "What was my attitude? I was thirsty," she says, when asked to explain her behavior that day. "But I can't say that I was completely oblivious to what I was doing."

Says a friend of Marram's: "She was sending Pepsi a message: 'If you buy Tropicana, you don't get Ellen Marram.' "

Pepsi bought Tropicana. And lost Marram. She says she "cast a wide net" for a new job. The search turned out to be longer than she or anyone had expected. One reason is her management style: Marram, 52, is more authoritative than collaborative and, according to many, too tough. "She belongs in a traditional company," says a leading recruiter, who asked to remain anonymous. "She's a very good marketer, but classic and buttoned-up. And she's demanding, sometimes unfairly so."

Last August, Marram signed on at a completely untraditional place: efdex, an e-exchange that links buyers and sellers in the food and beverage industries. It'll probably go public this year, and given investors' current passion for business-to-business stocks, Marram may well hit pay dirt. But efdex is a company with just over 200 employees. And instead of marketing hot new consumer products, Marram is engaged in the challenge of trying to convince companies that efdex is the efficient marketplace they've always wanted. It's a long way from where she dreamed she'd be.

RICK BRADDOCK

Old job: nonexecutive chairman, True North Communications

New job: chairman, CEO, priceline.com

Old pay: $600,000 salary and bonus, plus accumulated options

New pay: $300,000, plus 9.8% of priceline in stock, options (valued at $845.8 million)

He looks the part of the Connecticut Yankee, and he can't give up his suits, but gray-haired Rick Braddock is no fuddy-duddy: This guy goes where no executive has gone before.

As a brand manager at General Foods 35 years ago, Braddock sent Tang into orbit with the Gemini astronauts. At Citicorp for 19 years, he was a pioneering marketer, helping to build a credit card empire. After rising to Citicorp president under John Reed, Braddock "didn't get along with the chairman," he says, "and off I went." Since he left banking in 1992, he has dashed around the big leagues like a relief pitcher--CEO of drug distributor Medco, nonexecutive chairman of ad giant True North, and a seed investor in several Internet successes, including E*Trade. "I've had a lot more fun than if I'd taken the straight and narrow path," says Braddock, 58. "I've taken chances, and I've figured out how to double up on the good ones."

His latest "chance" is high profile: priceline.com. Braddock got interested in the name-your-own-price vendor in late 1997, putting about $1 million into the then-private venture. In 1998 he told founder Jay Walker that he was intrigued enough to invest more. Walker asked him to invest himself instead, as priceline's CEO. Braddock's job is a mix of duties, ranging from filtering the gush of ideas from the quirky Walker to improving priceline's once-dismal customer service to expanding into new areas such as--no surprise--financial services. With the stock down 64% from its high, Braddock has labored to convince Wall Street that priceline is a real company with real profits in its future. "The criticism that the company is a black box gets a little tired," he says impatiently. "We're building a great business here."

However long this career stop lasts, Braddock is finished with old-line corporate America. "Big companies, because of their size, are fundamentally defensive," he explains. "They protect what they have rather than do new things. I want to work in the fast-growth part of business for the rest of my career." Wearing a tie every step of the way, of course.

REPORTER ASSOCIATES Irene Gashurov and Noshua Watson

*"New pay" includes any vested and unvested options at their current value based on the latest stock price, or on venture capital valuations.