Neither did his son. At Brandeis University, where Sillerman majored in political science, he launched Youth Market Consultants in 1966, offering fellow students discount magazine subscriptions while advising marketers on how to target the teen set. He sold the company in 1972 to Boston's Ingalls ad firm, though he won't say for how much. While making the deal, he met a bright and passionate copywriter named Laura Baudo. At first, she was put off by his swagger. "Bob had hordes of women surrounding him, and I thought, 'Oh, get over your cheap self,' " Laura says with a laugh. "I wanted nothing to do with that." She pauses and adds, "That was moth to flame, wasn't it?"
When Laura sought his help in developing a musical greeting card, she learned what a lot of people learn if they listen to Sillerman closely. "Bob is very much a self-determinist," she says. "That's one thing I liked about him. And he likes conversation. That's not a usual male trait, is it? Other people might think he was attractive because of what was attached to him. He was successful. He dressed well. But I think it was that he really liked to talk and listen. He loves ideas."
In 1978, Sillerman joined forces with oldies D.J. Bruce "Cousin Brucie" Morrow to buy two tiny stations in upstate New York for $1.875 million.
"Bob can take a dollar bill and in 25 minutes it's a hundred dollars," says Morrow. "You don't ask how; you just appreciate it. It's really this talent to assemble the right people. I want to call it charm, but it's actually quite frightening. He has this ability to absorb and master any skill. Thank God he never became Cousin Bob." On the first day they hit the air, Sillerman cried. Over time, the pair amassed a string of scrappy radio and TV outlets. But Sillerman's frat-boy humor (pretending to steal paper supplies during a crucial contract deal, awarding gold sales pins with the letters sls for "Sell Like Shit") and his tough deal-making earned him a reputation as cocky but dependable.
"Deep down, Bob enjoys his celebrity and financial power," Morrow tells me. "But he knows people gun for you. He's a sweet guy in his personal life. In business, watch your gloves." By 1993, Sillerman had fought his way into an even bigger arena. That year, he teamed with radio-industry honcho Steve Hicks to take several stations public under SFX Broadcasting. When the Telecommunications Act of 1996 opened the way for ownership of multiple stations in single markets, they devoured dozens of properties to become the nation's seventh-largest chain. That year, Hicks left to become president of Capstar Broadcasting. With backing from his brother Tom at Texas buyout firm Hicks, Muse, Tate & Furst, Steve Hicks bought SFX Broadcasting for $2.1 billion. The transaction netted Sillerman $250 million -- and set the stage for his latest takeover.
The sale further increased his reputation in Southampton, where he had arrived in the mid-seventies with Laura after following some friends out for a weekend. They quickly began spending every summer weekend, camping out on living-room floors, with Bob dominating the local volleyball nets. As his star rose, he bought nine acres of property and began building two houses. Sillerman imported hundreds of Alaskan clear cedar logs, which were planed in town and assembled onsite. He ruled over every inch of the design, from the living room's vaulted ceilings and the 40-foot indoor pool and basketball court -- where a glass wall reveals swimmers, like fish in an aquarium -- to the private disco, where the stairs light up as you step down to the dance floor.
In his guest house, tons of timber were joined, without a single nail, by a Japanese temple builder using pegboards as a guide instead of blueprints. "These things are not monuments to money," he insists, in a reflective monologue shot through with moments of mysticism. "But in them, you feel this spirituality of the hands that have been laid on the wood to do this. I know this sounds sort of Shirley MacLaine, but there's something about the peacefulness of the men who built it. Every piece of wood supports the other."
In 1992, when Southampton College lost its chancellor -- the blue blood Angier Biddle Duke, ambassador to Spain under Lyndon Johnson -- Sillerman took over the post at the behest of his old friend Tim Bishop, the school's provost. Sillerman laid out two conditions for taking on the job: that the college scrap several ill-defined liberal-arts programs and focus on its major strengths -- marine science and creative writing. As in his business dealings, he also infused the college with his quirky humor. In a blatant publicity stunt that troubled old-guard administrators, he named Kermit the Frog as the 1996 commencement speaker. Thirty-one newspapers picked up the story, a free marketing bonanza that raised the college's profile and drew hundreds of new admissions.
Tom Petty, road-weary and bored, in yellow shades, just nods. He hates tiered seating . And he'll gladly fight about it. But not at a benefit.
"I thought right away this is a good marriage," says Roger Rosenblatt, editor-at-large for Time Inc. and professor of writing in the newly formed MFA program that was one of Sillerman's pet projects. "When you have a chancellor who is generous with his own money and his own time, it means so much more here."
Sillerman and his wife, who dreamed up the "All for the Sea" benefits, personally oversee every concert. They set up chairs, decorate tents with hanging fish cutouts, pick the area's top caterers. In other words, they roll up their sleeves. "Let's face it," says one administrator, "Bob is a rich guy who jets all over the place. He could just give us this money."
That's undoubtedly true. Sillerman owns a resort on Anguilla. He vacations in Paris and Cuernavaca. He recently flew several friends to Ireland on his ten-seat Challenger jet, then rerouted the whole group to London for a Rolling Stones concert. In truth, Sillerman is unquestionably generous with his friends, paying the college tuition of several of their children.