Born a poor boy with big dreams, Dennis Conner has turned the virtues of hard work and tenacity into a winning formula for international renown. Not only has he captured every sailing title worth going after, he also has honed the fine craft of selling sponsors on investing millions of dollars in a venture that has no concrete ROI.

How does Conner do it? With charm, single mindedness, the promise of great days to come and the assurance of a winner who knows how to turn even setbacks into opportunities. In short, Conner has all the earmarks of a master salesman.

Conner’s world fame was propelled not by a win but by a loss — a gigantic loss. In 1983, after scores of wins in international sailing competition, Dennis Conner’s Stars & Stripes went up against the Australia II, which featured a radical winged-keel design. By a score of four wins to three losses, Australia II ended the 132-year traditional win by an American boat in the America’s Cup Race. To Conner, a determined competitor who was used to winning, the loss was devastating.

Three years later, Conner was back with a vengeance and regained the Holy Grail of sailing by shutting out his opponent in the best-of-seven series.

In 1988, after a controversial challenge by New Zealand, he won again. Conner, who — for better or worse — has revolutionized sailing competition, was reestablished as the world’s greatest sailor. Now, the 48-year-old Conner is back to defend the Cup in 1992 in his home port of San Diego.

— Skipper Conner —

As a child, Conner confesses, he suffered from an inferiority complex. Other San Diego boys had boats; he did not. At $800, even the Starlet, a small keelboat popular during his boyhood, was out of his reach. Despite not owning a boat, Conner became a junior member at the San Diego Yacht Club when he was 11. It wasn’t until 1970, when Conner was 27 years old, that he was able to buy a half-interest in his first boat, a 33-footer that cost $1,700.

Conner admits he had a desperate need to excel at something. He found his outlet in sailing. He hung out at the yacht club the way other boys hang out at pool halls. His heroes became San Diego’s best sailors. “I helped them with their lines, asked them a million questions and generally made a pest of myself,” he says, “until I was invited aboard to crew.”

— The America’s Cup —

The truly big time came for Conner in 1974 when Ted Turner named him tactician on the successful America’s Cup defender Courageous. Six years later, Conner was the skipper of Freedom. Again he won the Cup championship. Since 1971, Conner has represented the United States in every America’s Cup final race, with the exception of 1977. He was then competing in the Star Boat World Championship and the Olympics, where he won a bronze medal.

— A Desperate Hour —

After the loss on Sept. 26, 1983, Conner sat under blistering television camera lights with tears streaming down his burnished cheeks and faced the world alone. He offered no excuses.

The scene touched Americans. Thousands of people wrote to Conner, expressing their support. “The two things that saved my sanity in ’83,” Conner said after the race, “was that in my heart I knew I had done everything I could, and the second thing was the people. After I won the Cup in 1980, I received about 100 letters. Out of 200 million people, that isn’t very many. In 1983, I got thousands, maybe tens of thousands. In defeat, I found support I had never known in victory. They were proud of me. In essence, the Cup was freed.”

Conner’s tears didn’t last long. In a column Conner wrote for Sports Illustrated after the 1987 win, he laid out meticulous plans he had made for winning back the Cup. “Almost as soon as I lost the Cup in ’83, I began figuring ways to get it back,” Conner wrote. “Piece by piece the picture fell into place. I saw it all very sharply.”

— A Bigger Sale —

His entire plan of attack centered around building a faster boat. The radical Australian design had caught Conner off guard. Conner later said the best boat beat the best crew. Having a faster boat for the 1987 competition meant more money. Conner planned on a budget of $16 million.

Now he had to convince corporate America that he could win back the cup. Conner carefully considered where to practice and who would sail. He acquired other boats and outfitted them with a winged keel (like that of the Australian boat in the 1983 races) to compete against his latest Stars & Stripes.

He selected Hawaii as his test location. Its strong winds are similar to Australia’s. The logistics were more manageable. Crew members who had jobs and were only allowed to sail 10 days a month had less travel time than from other locations. Espionage by other teams could be kept to a minimum.

Conner looked over more than 200 men from the United States to crew for him before deciding on the final 75. The result of Conner’s preparation was a spectacular win. The Stars and Stripes led in every mark of every race, always finishing at least one minute and 10 seconds in front. Conner calls the 1987 win his proudest moment. After the race, the America’s Cup sat next to him in the U.S. bound plane in a first-class seat of its own.

— Attitude, Attitude, Attitude —

In The Art of Winning, a book he wrote in 1987 after he brought the Cup back to the United States, Conner reveals the method he uses to win in sailing and in business. That method has five key ingredients: attitude; performance; teamwork; competition; and goals.

Conner has been quoted as saying he looked for three characteristics in the selection of his successful 1987 crew: attitude, attitude and attitude. He told them they must have complete commitment to the competition. They had to focus entirely on winning the Cup. “Families, social lives, sex, religion or whatever had to be sacrificed for our goal,” Conner said.

The next step was performance and that involves intense preparation. Conner often refers to the massive preparation for a race as “no excuse to lose.” Do everything to eliminate the possibilities of defeat. When you lose, Conner recommends you find the up-side, consider a tactical change, do a reality check and examine why you lost and immediately plan a comeback.

For Conner, the measurement of success depends upon your goals. “In business, it’s the income statement. Did you make a profit or a good return on the owner’s equity? In sailing, it’s how you did in the race. How does the result compare with your goals? Some people who go to the Olympics are thrilled to death with the bronze medal. Others are disappointed if they win anything less than the gold. Certain people are thrilled to get there at all.”

— Selling Dennis Conner —

Within days of recapturing the America’s Cup in 1987, Conner appeared in a now well-known television commercial. A voice on the advertisement shouts from the crowd of portside revelers, “What are you going to do next, Dennis?” Answers a beaming Conner, “I’m heading for Walt Disney World.” Conner had arranged his appearance in the commercial with Walt Disney Co. before he won the Cup.

In the two months following the win, Conner’s name appeared in advertising for Pepsi, Wheaties, Budweiser and Polaroid. He modeled Sperry Topsider shoes, Izod shirts and Ray-ban sunglasses. IBM and Merrill Lynch hired him to run motivational seminars. Edsel Ford II, great-grandson of the founder of Ford Motor Co., presented him with a custom-made Lincoln Mark VII, trimmed in red, white and blue. He was even recruited by the Australian government to do tourism promotions.

It wasn’t the first time he had appeared in Australian television ads. After the loss of the 1983 Cup, Conner starred in a commercial for the Australian state lottery in which he said, “Remember me? I was the skipper who lost the America’s Cup.” During the elimination trials of the 1987 Cup series, Conner was on the phone daily soliciting corporate support. In less than a month, he had enough corporate sponsors to retire $3 million of the Sail America syndicate’s $4 million debt. At the same time, he was cutting deals for himself.

He sold his first-person account of the Cup contest to St. Martin’s Press, which offered him a six-figure advance, win or lose. Comeback: My Race for the America’s Cup was rushed into print shortly after the race.

— Determined Salesman —

Donald Trump recalls his first encounter with Conner in the introduction of Conner’s 1988 book, The Art of Winning. Conner was wooing potential sponsors for the 1987 America’s Cup competition. Without an invitation, Conner plunked himself down in the lobby of Trump’s office. The secretaries could not get rid of him.

Conner offered them two choices: either they could let him see Trump or they could call the police. Trump agreed to give him a few minutes but quickly became fascinated with Conner and his presentation. Conner laid out the promotion he had planned for the Trump organization. He detailed how he planned to win the Cup. Trump was sold. He helped fund Conner. Later he underwrote the ticker-tape parade up Fifth Avenue in New York City after Conner won the race.

— The Art Of The Deal —

Considered a necessary nuisance by other sailors, Conner loves the art of the deal as much as he loves the competition of racing. More than the sailing, he loves the winning. He admits he likes hobnobbing with the best in other fields. “I enjoy meeting successful people and constantly being challenged by other opportunities,” says Conner. “It’s not like work.”

Conner has been known to remind people he is a businessman first. Sailing is his hobby. Conner attended San Diego State, where he studied business. Following college, Conner joined the Raffee Co. (owned by a sailing buddy) and worked in carpet and home furnishing sales. In 1983, he founded his own drapery and carpet company, Dennis Conner Interiors, which supplied U.S. retail chains. He has since sold the company.

In 1987, Conner formed Dennis Conner Sports, Inc. to market sailing and other sports enterprises. Through this company, he has worked with major clients on product endorsements and sponsorships in multi-million-dollar campaigns.

While respected for his sailing ability, Conner isn’t particularly popular with his competitors. His manner has been compared with tennis brat John McEnroe. He has been known to lash out at an opponent or a reporter. Yet he is enigmatic. Those who work directly for him describe him as a totally different person. He never shouts, screams or gets upset at the helm of his yacht. He quizzes his crew members for their opinions.

Other sailors claim Conner has killed what was a pleasure sport. Sailing competitions have turned into multi-million-dollar campaigns, requiring corporate sponsors and corporate logos plastered on boats and sails.

Even Conner never dreamed the campaigns would become as large and complicated as they are today. Still, he considers fund-raising a way of life. “I’m a skipper when I go out sailing and when I’m not sailing, I’m responsible for fund-raising,” says Conner matter-of-factly. “The America’s Cup is a big campaign, and there are lots of different jobs. My particular job is to raise the money. Other people have responsibilities in design or sail-making or whatever. It’s a multi-faceted effort.”

Says Alex Morton, executive vice president of D’Arcy Masius Benton & Bowles, the advertising agency for Cadillac Motor Car Division: “Dennis considers fund-raising a part of the total experience. He doesn’t look at it as drudgery. As he gets closer to racing, it obviously begins to take away from his race time, which he doesn’t like. But he considers fund-raising a key component. This is the world’s premiere event in his sport and if you want to compete and win, it requires that you establish relationships, negotiate sponsorships, generate funds, acquire the technology, people and funds and generate interest.”

Cadillac was the first sponsor to sign on for the 1992 event. The General Motors’ car division was a sponsor of the 1987 America’s Cup, where Cadillac officials and Conner eventually met. Conner came knocking on Cadillac’s door as he tried raising money for the 1988 challenge to the Cup. But so much controversy and legal battles surrounded the 1988 event that Cadillac bowed out. As he kicked off fund-raising for his 1992 campaign, the persistent Conner returned and Cadillac signed on as his first sponsor.

Not only did Conner need money, which Cadillac was able to provide, he needed technical assistance since the 1992 Cup was destined to feature the most technologically advanced boats in the history of sailing. Cadillac, through its parent company, was able to provide that assistance. General Motors’ designers and engineers volunteered their free time to help with testing the design of the boat’s keel and rudder in its wind tunnel.

“Making the wind tunnel available to us is a dream that we never thought we’d have,” says Conner. “It is one of the best wind tunnels in the world and allowed us to do some testing that we never dreamed we’d have. Our deal with Cadillac has been more than just a one-way deal,” says Conner. “They didn’t just give us some financial support. They’ve been really enthusiastic and helpful in any way possible.”

Cadillac is equally happy with its association with Conner. “Dennis has certainly given us everything we discussed plus a lot more,” says Morton. Conner has appeared on Cadillac’s behalf to speak at yacht clubs nationwide and dealer events. He will continue to make such appearances throughout the next year.

Cadillac has sponsored programs on ESPN starring Conner that preview the upcoming Cup event. Those also will continue in the coming year. Conner has been featured in Cadillac advertisements and will appear in more leading up to the event and after, if he wins.

While Conner’s deal with Cadillac went together relatively easily, the fund-raising for the 1992 America’s Cup has been tough due to the Persian Gulf war and economic recession which has hit hard in the Northeast, where boating-related businesses and potential sponsors are located.

In addition to Cadillac, Pepsi and American Airlines have signed on as gold sponsors. Each has provided $3 million. Their company logos will appear on the masthead spinnaker of the Stars and Stripes. Pepsi has sponsored Conner in all of his efforts since the 1987 America’s Cup. The soft drink maker sponsored him in the 1987 America’s Cup and the 1988 challenge. Pepsi promised if Conner won the Cup back from the Australians in 1987, they’d be back to sponsor him. He won and Pepsi is back.

“He’s a proven winner,” says Pepsi spokesman Andrew Giangola. “One of the reasons we’re so delighted to sponsor Dennis Conner is that he is so visible,” adds Giangola. “He’s ready, willing and able to talk about sponsors and does so on his own. He’s genuinely grateful for the sponsorship, and he publicly acknowledges his sponsors when he’s doing interviews.”

Conner has a host of other small sponsors and suppliers including Hewlett-Packard, Ciba-Geigy, Newport News Shipbuilding Co., Citizen Watch Co. of America, Inc., Serengeti Eyewear, Sperry Topsider, Inc., Mt. Gay Rum, Brobeck, Phlager & Harrison, Stolichnaya Vodka, Collection Clothing Corp., Alexander Julian and Henry Lloyd. These represent a lot of selling time. Still, Conner has a long way to go to meeting his goal of $30 million, though he won’t say just how far. Some speculate he is significantly behind his competitors in money. Others say it is Conner’s style to be vague about how much money he has raised to let competitors think he is behind. “We’ve done pretty well considering,” is all Conner will say. “Corporate America is feeling better about itself. That’s in our favor.”

— The 1992 America’s Cup —

Holding on to the America’s Cup is not a sure thing for Conner. The competition is intense and well-financed. Clubs from New Zealand, Italy and Japan have budgets far exceeding Conner’s and they had their boats in the San Diego waters several months before Conner. But even before Conner can go head-to-head with the foreign competition, he must beat the other Americans to defend the Cup.

From January to March of 1992, the field of a dozen competitors from 10 countries will be narrowed through elimination trials. The final Cup, best-of-seven series, which will feature a U.S. defender and foreign challenger, begins May 9, 1992. Conner is as vague about how well his boat and crew, now practicing 20 days a month, are doing as he is about his fund-raising.

“We’re proceeding along our charted course,” he says. “We’re comfortable that we have a very fast boat and good crew, and we’re looking forward to the races.”

A fast boat is key to the upcoming competition, Conner says. The 1992 series features a new class of boat. The 75-foot yachts will be the most technologically advanced ever raced. Generally, they are expected to be 30 percent lighter than their 1987 12-meter predecessors, 10 feet longer and have 40 percent more sail area. But since it is a new class of boat, Conner speculates there will be a wide range in speed.

“No one knows for sure what the right parameters are in the new America’s Cup Class boats,” he says. “I suspect there will be some boats out here that will be a little bit faster than others. With the 12-meter boats, only 3-1/2 minutes separated the slowest and fastest boats. You’ll see a bigger difference here because no one knows the correct design for sure. Without a fast boat, no matter how good you are, you can’t win,” says Conner. “You can’t win the Indy 500 with a car that is 10 miles an hour off the pace even if Emerson Fittipaldi or Mario Andretti is driving it.”

The competition is stiff. The other guys have more money. There are dozens of unknowns and the deadline is approaching fast. Conner’s still out there maneuvering and it’s a good bet that win or lose, he’ll go right on selling.