From Hollywood mogul to documentary subject to beloved benefactor, Shep Gordon is a legend in his own time—and content on his island in the sun.

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Shep Gordon, barefoot in fuschia print board shorts and a faded university of buffalo t-shirt, comes padding onto his lanai on Maui’s Keawakapu Beach, emitting the distinctive staccato laugh much imitated in Supermensch: The Legend of Shep Gordon, Mike Meyers’ adoring 2013 documentary of the talent manager. That film, along with his best-selling memoir They Call Me Supermensch, has had some unintended consequences for Gordon of late … such as uninvited visitors.

“I came out of the office and all these people were coming down the driveway, dressed in identical shirts and wearing leis,” he said to his assistant, Nancy Meola, handing her a CD. “They’re some kind of group, I guess. They gave me this.” He laughed again and grabbed a cup of coffee. “Too bad I don’t have a CD player.”

It’s true—there’s no canned music in this house that music built. On Maui, Shep Gordon’s music comes from his surroundings.

“I’ve never had a stereo here. Music is just boring to me,” comes the surprising admission of a man who’s spent a good part of his life managing musicians. “On Maui, I just want to listen to the ocean and the breezes.” Gesturing toward the waves breaking just a few dozen feet away, Gordon says that he didn’t know there was an actual name for that sensation until recently, when he received an email from a local kapuna. “He talked about ‘pana,’ the sound of the land you’re on, which is your heart connection. That really hit home, because the ocean and the breezes have a heart, soul and personality—big ones—and I fit into that harmonic.”

In addition to being a charming raconteur and brilliant businessman, Shep Gordon can be very deep that way, his melodious voice switching between riotous show biz stories to emotional and sensitive topics, such as his decision to adopt the four grandchildren of a former girlfriend after their mother died.

After years of working and hanging with the planet’s boldest-faced names (a quick sampling: Groucho Marx, Salvador Dali, Raquel Welch, Alice Cooper, Emeril Lagasse, Teddy Pendergrass, Michael Douglas, Sharon Stone—a former girlfriend—Willie Nelson, the Dalai Lama—get the picture?) at 70, Gordon is himself taking a turn in the spotlight with his memoir, which was published last fall.

In it, Gordon recounts a career charmed by a series of seemingly random connections, starting with his first night in Los Angeles in 1968 where, jobless and broke, he ended up in a Hollywood motel where the other residents included Janis Joplin and Jimi Hendrix and frequent visitor Jim Morrison. In addition to his talent management skills, he’s been a movie producer and classically trained as a chef (cooking is his first love). He is a brilliant brander, helping pal Sammy Hagar launch his spectacularly successful Cabo Wabo Tequila line and Willie Nelson’s Whiskey River Whiskey. Why do you watch celebrity chefs on the Food Network? Another Gordon master plan, hatched when he learned how little most chefs earned.

But his supremely comfortable beachfront home on Maui is where Gordon is content to spend most of his time these days. He says he fell in love with the island the first time he set foot on it in 1974. “I said, ‘I’m living here the rest of my life.’ I just felt different in my skin.”

He laughs at the Shep Gordon of that era. “I was the typical Hollywood guy who moved to Maui. I kept my rings on; I was that guy.”

That guy fell in love with Hana when he first arrived on island, so much so that he rented Charles Lindberg’s Kipahulu cottage in 1976. And in those pre-FedEx/cellphone/ email days, he rose to full Hollywood Guy height when he discovered that the house phone was a party line. “I was out the door in a minute to track down the phone company, which was in a house. When I arrived it was like a Norman Rockwell painting of a family having lunch. “I told the guy, ‘Hey, I run a big company in L.A.; I need three or four lines with a hold button.’ He looked at me like I was completely insane and said, very slowly, ‘Son, let me give you some advice. If you don’t have the time to talk to someone, call them back.”

“He was so right!!”

Gordon still regularly visits there, describing the Hana pana as “overwhelming. It’s a place that if you’re not comfortable with yourself, you get out of there real fast, because you have nothing else to deal with except yourself!”

But in South Maui, his home serves as a VIP clubhouse. If you are famous and on Maui, you’ll end up at Shep’s sooner or later, says his friend of 30 years, the accomplished chef and restaurateur Mark Ellman. “You wouldn’t believe who has been to his dinner parties! They all come to kiss the ring of the Pope of Maui, and Shep will meet them at the door wearing a pareo and a hole-y t-shirt!”

Gordon insists that the trick to a good dinner party is good food (of course), round tables (“creates a sense of equality”) and no business discussions. His parties are “all about living in the moment and being thankful for good food and good friends.”

For his off-island visitors, Gordon says downshifting them to island speed usually takes a day or two. “I usually feed them first, some matzo ball or chicken soup—something my grandmother used to give me that is comforting. Then I make them sit with me and absorb. And it usually takes a day or two, but it rubs off and each finds their own path.”

He describes himself these days as “pretty much retired,” which he translates to “I do everything the same, I just don’t get paid for it.”

He shrugs. “I’ve always been fortunate to have resources and I like to see them used to help somebody.” He describes his philanthropy as “giving to eyeballs. I’m not really good at giving to institutions. I like driving down to the Maui Food Bank and see them helping somebody.” Gordon hosts an annual star-studded New Year’s Eve bash for his two favorite Maui charities. Proceeds have benefited the Maui Arts & Cultural Center, and helped the Food Bank serve more than one million meals. His nickname there: “The Good Shepard.”

He recently worked with celebrity chef and Hawaiian regional food pioneer Roy Yamaguchi on the newly opened Humble Market Kitchin at Wailea Beach Marriott Resort & Spa. Plus, since his book hit the New York Times bestseller list, he’s finding himself in demand as a speaker, where his win-win “compassionate business” philosophy is resonating with audiences.

“It’s really unbelievably humbling, but also great ego massaging,” he reflects, admitting, “especially for someone with low self worth.” Gordon says he finds it “very confusing to be taken as a guru by so many people, but I’ve gotten much more comfortable with it.”

“It’s been good to know that there is something of value in this random life to pass on to my kids and others.”