Welcome back to Guyset and my first ever interview! 

Michael Cecchi-Azzolina is the author of Your Table is Ready: Tales of a New York City Maître D' and opens his new restaurant Cecchi's in the West Village today! We talk about everything from his encounters with Mick Jagger, Anna Delvey, Common, and Meghan Markle to New York City in the 80s and drugs in Tompkins Square Park at 4 AM. This was well beyond what I expected for my first interview. Michael was ready to talk about anything, you're in for a ride.

"40 Years in NYC Restaurants: What I Learned Serving Everyone from Mick Jagger to Anna Delvey"

Michael's journey from a lost kid in Brooklyn to one of New York's most respected restaurant industry professionals is a masterclass in perseverance, adaptability, and finding success in unexpected places. Having worked in some of Manhattan's most iconic restaurants and navigating the wild transformation of New York City from the dangerous 1970s to today's gentrified landscape, Michael's story offers invaluable lessons for young people trying to make it in the big city.

Growing Up Lost: From Brooklyn to University of Florida

Michael's story begins in a Brooklyn that few young people today would recognize—a place he describes as "really bad when I was growing up." As the first person in his Italian immigrant family to attend university, he had no roadmap for his future.

"I didn't know what I wanted to do," Michael admits. "My mother and father were born here, but there was never any talk of college. I didn't know what they were, really."

The turning point came during what he calls a moment of clarity during an acid trip: "I realized this is really fucked up. I gotta get out." This led him to finish high school in Florida, where a chance encounter with a Playboy magazine showing the University of Florida as the "#1 party school in the country" determined his next move.

Key insight: Sometimes the path forward isn't about having a clear plan—it's about recognizing when you need to make a change and having the courage to act on it.

The Theater That Changed Everything

At the University of Florida, Michael discovered theater almost by accident. His girlfriend's suggestion to audition for a play—which happened to be incorporating the then-popular trend of "streaking"—launched a career trajectory he never could have planned.

"I got cast in my first play, probably because I agreed to take off my clothes on stage," he laughs. "I don't think it had anything to do with talent."

But that theater, which would become the state theater of Florida, introduced him to Bob Moss from Playwrights Horizons in New York—a connection that would define his career.

New York in the 1970s: A Different World

Michael's description of 1970s New York paints a picture of a city transformed. Manhattan had "ghettos," the East Village was dangerous, and cab drivers wouldn't go east of Second Avenue. His first apartment between Avenue A and B cost $200/month—now those same apartments go for thousands.

"You'd have to use the pay phone from the corner to call the cops to go down the block so I can get into my building because there were junkies and muggers waiting," he recalls.

Despite the danger, the city pulsed with creative energy. "The bands—Blondie, the Ramones—were playing at CBGB. You had Basquiat doing his paintings in Tompkins Square Park. Keith Haring was doing his drawings in the subway. There was such heightened energy artistically and creatively that doesn't exist anymore."

Restaurant Career by Necessity

Michael's restaurant career began purely out of financial need. Working at Playwrights Horizons paid nothing, so Bob Moss connected him with a theater restaurant next door. What started as a necessity became a passion.

"I really liked it. And everything I've done, I always wanted to be the best at it. If I'm gonna spend eight, 10, 12 hours in this room with people, I'd also be damn good at it."

His first restaurant job put him in the middle of New York's cultural scene, serving everyone from Richard Gere to Mick Jagger. "A kid from Brooklyn was suddenly in the middle of New York with celebrities constantly, and it was fun. It was a blast."

The Dark Side: Confronting Addiction

The restaurant industry of the 1980s was notoriously hedonistic. "You could be out all night scoring drugs at Tompkins Square Park at four or five in the morning, getting to bed at 12 or one and getting up at three, putting a tuxedo on, going into work."

Michael candidly discusses how this lifestyle caught up with him, leading to serious addiction issues that required intervention. "I was really going down a really hard road and my girlfriend at the time left me... It got me to stop."

His path to recovery involved "massive amounts of therapy of all kinds"—including body work, EMDR therapy, and even working with American Indians in South Dakota. For Michael, addressing his history of sexual abuse was crucial to breaking the cycle of self-destruction.

His advice for anyone struggling: "The first step is definitely 12-step programs, but you gotta get the therapy. You have to understand what the crux of the problem is."

Professional Lessons: What Makes a Great Restaurateur

Understanding People

"A matrioti is sort of a dying breed," Michael notes. The art of hospitality goes far beyond taking reservations—it's about reading people and creating experiences.

Dealing with Difficult Customers

Michael shares a story about a notoriously difficult customer who kept returning despite terrible experiences. Instead of banning him, Michael persisted: "Something in me made me say I'm going to take it and I did... He turned out to be a very good customer."

His philosophy: "You're in hospitality. You want people to be happy. You don't want anyone leaving angry. But there are breaking points."

Celebrity Interactions

From Anna Delvey (the infamous fake heiress) to Johnny Carson, Michael has served them all. His approach remains consistent: treat everyone well, but maintain professional boundaries.

"I love people and I've had great guests from the couple down the block who no one knows—they're just lovely and they're my friends for now 25 or 30 years."

Coping Strategies for High-Stress Environments

When asked how he deals with restaurant stress now, Michael's answer is simple but profound: "Breathe, and then realize much of the stress that's happening in the business is not about you. It's about someone else."

His perspective on difficult customers: "I'm sorry you're having a horrible day, but I didn't do it to you. I'm sorry mommy and daddy didn't help you out back then, but don't take it out on us."

Coming Full Circle: Opening Cecchi’s

After three years away from the industry due to COVID, Michael is returning with his own restaurant—Cecchi’s—in the West Village. "I missed it. I love the restaurant business. I love the people. I love creating the experience."

His concept? A modern American bar and grill inspired by the Brooklyn establishments of his youth: "When I grew up in Brooklyn, we had a slew of restaurants called bars and grills. On the sign it said steaks, chops and seafood. My mouth still waters when I see those signs."

What to Look for in a Restaurant

Michael's advice for young diners goes beyond trendy spots and Instagram-worthy drinks:

1. The greeting: "The first thing is the greeting you're getting. Is someone standing there saying 'hi, welcome'?"

2. Attention to detail: "Is the sidewalk outside dirty? Is there paper on the floor when you walk in?"

3. Staff engagement: If the host is on their phone or the bartender ignores you, "probably not a place you want to be in."

4. Authentic experience: "Take a moment and really understand what you're going to and what you're eating... Get out of your phones and open your eyes."

Life Lessons from a Restaurant Veteran

1. Embrace Unexpected Opportunities

Michael's entire career stemmed from being willing to try things he'd never planned—from theater to restaurants to moving across the country.

2. Excellence in Any Role

"If I'm gonna do this, and I'm getting paid for this, I'm gonna be damn good at it." His commitment to excellence, regardless of the job, opened doors throughout his career.

3. Address Your Demons

Michael's willingness to confront his addiction and trauma head-on, through therapy and personal work, was crucial to his long-term success and happiness.

4. People Skills Matter More Than You Think

In every industry, but especially hospitality, understanding and connecting with people is invaluable. "I like people, I like to talk to people."

5. Know When to Move On

From leaving Brooklyn to leaving toxic situations, Michael recognized when environments weren't serving him and had the courage to change.

The Restaurant Industry Today

Michael observes that while the restaurant industry has cleaned up somewhat since the 1980s, it remains intensely stressful. His advice for young people entering the field:

• Find restaurants that align with your values

• Don't tolerate toxic management

• Remember that customer anger usually isn't about you

• Build genuine relationships with regulars

• Always maintain professional boundaries

Looking Forward

At an age when many consider retirement, Michael is launching his dream restaurant. "I'm too young for retirement," he says. "I love the restaurant business. I love creating experiences for other people—it's theater too."

His story proves that it's never too late to pursue what you love, that setbacks don't define you, and that success often comes from unexpected directions.

For young people trying to make it in New York—or anywhere—Michael's journey offers hope: you don't need to have it all figured out from the start. Sometimes the best path is the one you stumble onto while looking for something else entirely.

Want more stories about people who turned unexpected challenges into success? Subscribe to Guyset for conversations with individuals who've navigated unique paths to build meaningful careers and lives.

Timestamps (Minutes):

(4:20) Our interview starts

(5:05) We talk about his childhood 

(10:16) We talk about what New York was like in the 80s

(13:26) We talk about the East Village

(16:02) We talk about his first restaurant experience

(19:30) His experiences with drug and alcohol abuse (this is the part to skip if you do not want to hear about these topics)

(25:35) We talk about dealing with stress (this is one of my favorite parts and the best pieces of advice for anyone in a job)

(27) We talk about his worst customer experience

(30:51) We talk about his time with Anna Delvey

(34:49) We talk about his favorite celebrity encounters

(38:36) We talk about his experience with Meghan Markle

(40:17) We talk about why he stepped away from the restaurant world and what’s bringing him back for his new restaurant

(44:13) We talk about the restaurant scene and competition in NYC

(49:32) Michael tells us what we should look for in a restaurant to set them a part

(52) I say thank you and we say goodbye

My criteria for an interviewee is someone that will be helpful or interesting for guys in their 20s to hear from- let me know who you want me to have on next! Email me: josh@guyset.com

Send in any questions, things you want me to talk about, or things that should be talked about for guys in their 20s to josh@guyset.com  

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See you next Friday.

If you want to read more about Michael- click for his Grub Street article HERE