By his own admission, Michael Gill was a child of privilege.
"I was born with just about every advantage you could imagine, or even wish for," he told Mason.
He went to an Ivy League college, was a top executive at a world renowned ad agency, and had a six-figure salary. But now at age 67, he's trudging through the dark just before 5 o'clock in the morning, to make the early shift for his new job.
He's a barista at Starbucks.
"This was not on my goal list when I went to Yale."
This is the story of an affluent man's fall from grace, and how he found redemption in an unexpected place, a story Michael Gates Gill tells in his book, "How Starbucks Saved My Life: A Son of Privilege Learns to Live Like Everyone Else."
He describes it with almost a religious connotation.
"Oh, I think there's definitely a sense of, I would have to say, divine grace about my life. Because I definitely didn't deserve this kindness."
He was born the first son in a prominent family. His father, Brendan Gill, was a writer for the New Yorker for more than 60 years, author of a bestselling history of the magazine, and friend to many of the city's most famous faces.
"My father was a very well-recognized figure," Gill said.
When Mike was still a boy, the Gills moved to a prosperous New York suburb called Bronxville. Their house had 25 rooms, a gymnasium, and a two-story library.
Following in his father's footsteps, Michael went to Yale, and was hired out of college to work at J. Walter Thompson, then the world's biggest ad agency.
"I was what was called a creative director, and that means my job was to encourage other people to have ideas, like an orchestra leader," Gill laughed.
He presided over ad campaigns for the Marines, Christian Dior and Ford. For 26 years he climbed the corporate ladder. But he didn't see the end coming.
"No, I was really shocked by it, which I shouldn't have been."
He was 53 when a fellow executive invited him out to breakfast:
"And she said, you know, those classic words: 'Michael, we have to - we have to let you go.'"
"How did you feel at that moment?" Mason asked.
"I felt stunned. To be 53 and fired in advertising is really a death notice."
Gill tried to start his own consulting business, but couldn't make it. Then money began to get tight.
"I was dressing up everyday with a tie. It's sad now to think about it, but I was dressing up like I was an executive when I didn't have any work."
"Were you surprised at how fragile it all turned out to be?"
"I was surprised at my inability to cope."
Things quickly went from bad to worse. First Gill lost his job, then an affair ended his twenty-year marriage, when his girlfriend gave birth to a son. The final blow came four years ago, when he was diagnosed with a brain tumor.
He was at rock-bottom.
In a desperate attempt to find comfort, Gill found himself going back to his first home in New York City.
"You know, I didn't do it consciously, but I found myself back in the neighborhood I'd been at least appreciated and loved in, [where] I was a fortunate son in a fortunate world, and I was trying to, I think, recapture that sense of, 'I have a place in the universe,' because I felt like I'd fallen out.
"But then I looked over there. And there was a brightly lighted Starbucks store."
He walked over. What he didn't know was Starbucks was hiring that day. And when Gill sat down to brood over his latte, a woman approached him.
"She said, 'Would you like a job?'"
Gill's answer would literally change his life.
"And when she asked me that, I just didn't have the energy to lie or even be polite. I just said, 'Yes, I need a job.'"
"Why did you say, 'yes'?" Mason asked.
"I don't know. It was desperation or courage, but I think I just realized this is the moment I can't afford to miss."
He said the idea of putting on a barista's uniform was humiliating, and scary.
"I mean, it's one thing to get fired from J. Walter Thompson. It's another thing to be fired from Starbucks because you can't even do the basic job."
Those fears proved unfounded. In fact, he had found his calling.