Guy Oseary has spent more than three decades working alongside Madonna. He said that the pop star’s work ethic influenced how he built his own career.
On Tuesday’s episode of “The Tim Ferriss Show,” Oseary — Madonna’s longtime manager — said some of the biggest lessons he learned from the singer only became clear in hindsight.
“Her work ethic is not to be believed. Her commitment to her craft is not to be believed,” Oseary told podcast host Tim Ferriss.
He also said that Madonna has a great eye for talent and called her “the greatest identifier” of creative people.
Beyond that, Oseary said the biggest lesson he took from working with Madonna was her belief that nothing was off limits.
“There are no walls around her thoughts. There’s no ‘Oh, I can’t do that,'” Oseary said.
Looking back on his early years at Maverick Records, the record label Madonna cofounded in 1992, Oseary said the pop icon’s influence helped shape a company culture where he didn’t feel pigeonholed.
“If you went to any record label, they probably would have put me in a compartment,” Oseary said, adding that labels typically organized employees into departments based on genres such as pop, rock, and hip-hop.
Instead, he was able to move between different roles throughout his career.
“I went from this to this, to that, to that, to that. And I think it’s really just being around her has allowed me to never think in a limited way,” Oseary said.
Additionally, Madonna’s ability to keep looking ahead has also been central to her staying power, he added.
“She doesn’t sit well on her past. She’s not high-fiving herself,” Oseary said. Instead, she “keeps it moving forward,” he added.
Watching Madonna continue to defy expectations throughout her career has inspired him to keep pushing forward in his own, he said.
“She just doesn’t celebrate her accomplishments. She just starts like it’s a brand new day,” Oseary said.
Over the course of his career, Oseary has worked with artists including U2 and the Red Hot Chili Peppers. He was also an executive producer on the “Twilight” film franchise and co-founded the venture capital firms A-Grade Investments and Sound Ventures with Ashton Kutcher.
Oseary isn’t the only person who’s reflected on the lessons they’ve learned from working with some of music’s biggest stars.
Hollywood producer Will Packer said in 2025 that having Beyoncé turn down a role in one of his films five times taught him how to handle rejection. Rather than taking the rejection personally, he revised the script based on her feedback.
“You only need one, so whatever your Beyoncé is, right, keep seeing if there is a way to adjust and learn something from the ‘No,'” he said.
In a recent podcast interview, Law Roach said one of the biggest lessons he learned from working with Celine Dion came while helping her get ready for an event.
As he rushed to fasten one of her shoes, Dion told him, “Take your time. It goes faster.”
