At ECRM’s On & Off Premise Adult Beverage Session, I had the honor of hosting a fireside chat with Michael Franzese, a former mob boss who is a great example of the power of positive transformation and how one can turn second chances into success.

As a capo in the Colombo crime family, Franzese was one of the most lucrative earners in the American mafia. He later walked away from organized crime to build a new life as an entrepreneur, public speaker, author, and founder of Franzese Wine, which won Best Wine in the 2024 Grand Tasting Awards sponsored by Food & Beverage magazine.

During our conversation, Franzese shared his journey from mob boss to his current role as a motivational speaker and legitimate businessman, the lessons learned from both worlds, and how he now leverages those experiences to grow successful brands.

Below is an condensed and edited transcript of the fireside chat discussion. To watch the full interview, check out the YouTube video below!

The mob life

ECRM: Can you share your history with the mob, how you got into it, and your rise within the Colombo family?

Franzese: My dad was underboss of the Colombo family, one of New York’s five mafia families. He was like John Gotti before John Gotti, a major target of law enforcement. I grew up hating the police and government.

In 1966, my father was convicted of masterminding a nationwide string of bank robberies and sentenced to 50 years—the longest ever for that kind of case. I was a pre-med student then, planning to be a doctor, but family members pressured me to help him. I loved my father, he was my hero. Eventually, I made the decision to leave school.

My father proposed me for membership. You can’t just ask to join—you must be vouched for. After two and a half years proving myself, on Halloween night in 1975, I took an oath and became a made member. I rose from soldier to captain, running a large crew for many years until I decided to walk away.

ECRM: You’ve described yourself as a racketeer rather than a gangster. What’s the difference?

Franzese: In our family we had about 115 made men, but only maybe 20 were real earners. Those were the racketeers—guys who knew how to use the life to build businesses. Gangsters didn’t. They just wanted no-show jobs and did the heavy work. A true racketeer had to be both: you earned money, but you also had to be ready to do the other things when called on.

ECRM: We have a few convenience store-petroleum operators in the audience. Can you share a little about the gasoline tax scheme you did?

Franzese: Beyond gambling and loans, I had many businesses—car dealerships, restaurants, a film production company. But the biggest was the gasoline tax scam. I figured out how to defraud the government out of tax on every gallon of gas.

At its height, I had 350 gas stations and 18 companies licensed to collect tax. We were moving half a billion gallons a month, clearing 30–40 cents a gallon. It was one of the most lucrative rackets since Prohibition.

Leaving the mob & positive transformation

ECRM: Transformation is now a major theme of your life. What led to yours?

Franzese: In 1984, I was producing a film in Florida when I met a young dancer who became my wife. I realized I couldn’t put her through what every mob family suffers. By then, I was a major target of law enforcement—arrested 18 times, indicted seven, acquitted five. It was only a matter of time.

So I decided to leave. I eventually took a plea deal, served eight years in prison—three in solitary—paid $15 million restitution, forfeited planes, boats, and property. It wasn’t easy; there was a contract on me, and my father was upset. But I survived, and I believe God had a different plan for me.

Business lessons from the mob

ECRM: You've learned a lot about business during your time in the life, especially about negotiations and the value of preparation, which really resonated with me because I'm always touting the value of prep for brands going into buyer meetings. What are some of the things you have learned about negotiations and preparation?

Franzese: In that life, you were always negotiating—sometimes for business, sometimes for lives. Preparation was critical. You had to know what you wanted, what you’d accept, and what you’d walk away from.

For example, with contractor Jerry Gutterman, I did my homework, leveraged unions, and negotiated a deal that worked for everyone. On the flip side, I hired a guy at $1,500 a week to collect money from gas stations. After a couple months he asked for a raise—because he was counting my money, not his. I fired him immediately.

My father always said, “Be a good listener.” Sometimes silence gave me all the information I needed. Negotiation is part of everyday life—with your spouse, kids, neighbors. Learning it is vital.

Getting on social media 

ECRM: You now have a huge social media following—over 1.7 million subscribers on YouTube alone. How do you leverage social media for spreading your message of transformation?

Franzese: During the pandemic, my speaking events were canceled. My team pushed me to YouTube—I resisted, but eventually started five years ago. It blew up, and I saw the power of social media.

ECRM: How has that helped your wine business?

Franzese: Distributors don’t move your product—you have to. So we use social media to educate consumers, drive them into stores, and build demand. Last year we were in 400 stores; now we’re in 3,400 and expect 5,000 by year’s end.

Origin of the Franzese Wine brand

ECRM: How did you start Franzese Wine?

Franzese: A young man approached me. His family owned a vineyard in Armenia. Their story of transformation—grapes into wine—resonated with my own transformation. I liked the wine, the price, and the family, so we partnered. Three years later, we’re very happy with the results.

We’ve launched non-alcoholic wines, which Walmart has picked up, as well as fruit wines like blackberry and pomegranate. They’ve been so successful that retailers asked us for new varieties like cherry and strawberry. We’re always innovating.

ECRM: What’s next for you and your brands?

Franzese: We have a new frozen pizza brand, called Slide Pizza. We’re working on getting Slice Pizza into Starbucks—that would be a game-changer. Wine is also a daily focus, and I continue speaking, writing, and charity work.

I know I’m blessed. Of the six men sworn in with me in 1975, I’m the only one alive. Of the 50 mobsters listed in Fortune magazine in 1986, I’m the only one alive and free today. God gave me a second chance, and I try to make the most of it.

From the audience Q&A: Negotiating with the government& working with celebrities

Audience Question: What was it like negotiating with the government?

Franzese: That was my toughest negotiation. They wanted 25 years and a $100 million fine. We got it down to 10 years and about $20–25 million restitution. I had leverage—I had just beaten Giuliani in a seven-month trial, and they badly wanted a conviction. Without that leverage, I might not be here today.

Audience Question: For those thinking of bringing in celebrities to support brands, how do you make them effective partners?

Franzese: Don’t waste money on someone who won’t work. A celebrity has to get behind the product—promotions, tastings, social media. We put in the work, constantly. That’s why Franzese Wine has grown. Just a name isn’t enough.

Watch the full interview here!