No one in media has been as honest about their game as Howard Stern, who defected from K-Rock and terrestrial radio to Sirius Satellite Radio in 2004 and is now in the middle of contract negotiations with an employer that owes all of its success—Sirius reaches over 27 million subscribers nationwide—to the King of All Media. Like all things Stern, the negotiation has been very public, with Stern talking big numbers (he already makes over $80 million a year) and teasing his vast audience with talk of retirement.
But Stern will never retire. He has always been a workhorse, and he's never been busier. In addition to his radio show, Stern is a judge on NBC's "America's Got Talent," playing competitive chess, raising three daughters, pursuing professional photography, painting, practicing Transcendental Meditation and working with his wife, Beth, to raise money for the North Shore Animal League. Despite professing that he hates leaving his house, Stern is his own industry. He is unassailable.
What remains most impressive about his particular brand of industriousness is that he doesn't merely work hard. He learns from mistakes and constantly tweaks his act. The crass Stern of the nineties evolved into the understanding Stern of the aughts and then the profane academic of today. He has become far and away the best celebrity interviewer in showbiz. He asks hard questions and gets famous cyphers to open up about, well, everything. And there's no trickery involved; Stern merely plays to his own advantage. The secret to his success—and what most people overlook—is that he is, above all, an honest guy. He isn't bringing artifice into his studio. The only way a subject can avoid sounding disingenuous while talking to someone Stern is by not being disingenuous. That's some chess strategy right there.
So what does Stern really want? If it was money, he could have retired long ago. What he really wants is respect. Respect can take the form of a lot of zeros on a check, but there are other numbers that matter more: The size of the man's audience has always been his major point of pride and with the internet offering so many alternative distribution options, Stern has the chance to put his own money where his mouth is. Will he strike out on his own? Maybe, maybe not. The thing about Stern is that he's always been on his own—and he's fine with that. He can look out for himself.