Ben Heldfond’s Road to Redemption

Photos by Michael McCoy

Ben Heldfond’s most prized possession is a book, one that resonates with the story of his life.

A first edition of The Big Book of Alcoholics Anonymous, written by AA’s founders, Bill Wilson and Bob Smith.

Heldfond, who is 24 years sober, is forthcoming about his story of recovery.

Heldfond is a self-described serial entrepreneur. Through his company, Heldfond Holdings, he invests in a wide variety of companies. Some of them he has an active role either through management or the board of directors. While the other companies, he is a silent private equity investor. Heldfond Holdings, started off as a real estate company that operates multi-family apartments in California and Florida. The company currently has approximately $35 million in assets. The passive investments made in Heldfond Holdings include seed investments in companies like FanDuel, ThirdLove and Rubrix to name a few. The company currently holds 20 companies.

He treats his business the way he treats his life—with freedom and hope.

Heldfond was born and raised in San Francisco. His grandfather, Benjamin Swig, was the founder of the Fairmont Hotel in San Francisco, which the family sold in the early 2000s. 

He was deeply affected by his parents’ divorce at a young age. The process was bitter and angry, as divorce often is.

Later in his life, he would rely on that experience to work through his own divorce and minimize the impact to his son.

“It was hard on my brothers and sisters. We were sort of caught in the middle of this battle, being used as blocking and tackling tools,” he says.

He’s clear that he doesn’t blame his parents for his path of self-destruction. “I never thought before I acted,” he says.

His battles with addiction peaked in college. “It was a couple years of partying really hard,” he says. “It was basically the Animal House,” of movie fame.

His partying ways came back to bite him though. “I actually ended up getting kicked out of the Animal House,” he says. “Who gets kicked out of Animal House for partying too hard?”

Through school, despite his partying ways, Heldfond managed to keep his grades up.

“I was juggling all these balls in the air, one of them being my addiction, my alcoholism. The other was school, my girlfriend and family. I was able to juggle all the balls for a while until I got involved in some harder substances, one by one they started dropping, and eventually all that was left was my addiction and alcoholism,” Heldfond says.

Heldfond reached a breaking point when he experienced an overdose  and decided to get sober. But much like other addicts, the journey was long and hard. His last drink was in 1994.

Heldfond met his first wife while working at a large nightclub in San Francisco. At first, he just wanted her to move her car.

“This woman pulls up in her fancy Lexus and I walk over to tell her there’s no parking here,” Heldfond says. “She pulls out her ID and obviously I recognize the last name — DeBartolo.”

She was the daughter of the former owner of the San Francisco 49ers, Edward DeBartolo Jr.—a fact Heldfond noted immediately, as a fan of the NFL team. “The 49ers were my life. I hadn’t missed a home game in probably 15 years,” he says.

Nicole DeBartolo didn’t just have the name, she also was beautiful—something else Heldfond noticed right away.

“All of a sudden, it goes from getting her to move, to how can I get them in the club,” he says as he laughs at the memory.

They began dating, and when the DeBartolo family decided to relocate to Florida, Heldfond followed his new lady love.

“Mr. D,” as Heldfond refers to his now former father-in-law, fell in love with Tampa after some playful ribbing from then-Mayor Dick Greco. “We were in Orlando, and [Greco] said, if Eddie didn’t drive the hour to come see Tampa, he’d never speak to him again. He might have been playfully joking, but there may have been some seriousness to it,” Heldfond says with a laugh. The Debartolos have called Tampa home since 2000.

Heldfond and Nikki bought a home in the upscale Avila neighborhood in Tampa. “I remember the first night, blasting my Beastie Boys in the car and watching neighbors eyeball me with judgement, going, ‘What have I done?’ ” he says.

Heldfond never thought he’d move away from the West Coast. And now Heldfond was across the country, away from everything and everyone he knew, and the culture shock was enough to put seeds of doubt into his head.

He was sober, engaged and felt alone in a new city.

Eventually the young couple moved to South Tampa which was, culturally, a little more Heldfond’s speed. But he struggled to find a new AA chapter and a sponsor—two pivotal parts of the never-ending sobriety-support process.

One of AA’s major tenets is that there is no cure for addiction, and that the meetings and network it provides are lifelong components in its support.

“I felt like I was a newcomer again and that’s a very lonely feeling,” he says. “Instead of feeling uncomfortable, I decided just not to go.”

Heldfond says he stayed true to his sobriety, but he wasn’t happy. “Although I never drank, I don’t know if I led the same [healthy] life,” he says.

The strain eventually took a toll on his marriage. Heldfond says many factors led to his divorce.

“We were put on this earth to be friends and to create a beautiful child,” he says. “We never fought that bad, it was more like living with a roommate for us.”

Heldfond had been working with Eddie DeBartolo during this time. One of their first business ventures was opening a restaurant called Tomatina, near the Veterans Expressway. It was a pasta and pizza restaurant. He says the main issue was, people had the mindset for a chain, which offers free bread and salad. For the quality of the food Tomatina tried to provide, it wasn’t cost-effective to operate with a chain-restaurant mentality.

“We were maybe about 10 years too early to open that type of concept out there,” he says.

The restaurant closed, and Heldfond began working at DeBartolo Holdings in Tampa.

There, Heldfond did well for himself. But something wasn’t clicking. “I was making all this money, and I thought that’s what I wanted in life,” he says. “I realized that I was making money, and had a good job, but I was miserable.”

Heldfond considered going back to school, and sought advice from DeBartolo.

“I went to my father-in-law’s office one day and told him I wanted to get an MBA and asked if he could help me get into Notre Dame,” Heldfond says. “He tells me, ‘You don’t need to go to school. From now on, I will copy you on all emails, and you can come to every meeting.’ He just gave me full access.”

He says the experience was basically the equivalent to attending business school for two years.

Eventually, Heldfond broke out into his own holding company and DeBartolo invested $1 million in his new venture.

“Although my father-in-law was the greatest man I’ve ever met, for me, it was [about] controlling my own destiny,” Heldfond says. “For me, it was [about] being my own boss, but also having the freedom to do whatever I wanted … which I already could, but there was guilt behind it.”

Heldfond and Nikki—Nicole’s nickname—split in 2006. Even though Heldfond had spun out his own holding company, DeBartolo offered him an office and access to his support staff.

As far as Heldfond Holdings goes, it’s just Ben and his assistant Lynda, who has been with him for 13 years. They both joke that it’s the longest relationship either one has had.

As their divorce proceeded, Heldfond and Nikki had some touch-and-go moments.  There were arguments, and from Heldfond’s perspective, some resentment. “I worked on myself and the 12 steps, and I eventually realized I wouldn’t have wanted to be married to myself either. I was just not a happy person,” he says.

They both eventually came to a peaceful space. “And from there, the world sort of opened up,” he says.

“Honestly, once we all let our guards down and put our egos aside it was fairly easy for us. We all know that what’s best for Asher (Nikki and Heldfond’s son), is our ‘Modern Family’,” says Nikki DeBartolo. “For me it was about finding myself and not blaming myself and realizing divorce doesn’t mean failure because what we have accomplished isn’t a failure.”

To be clear, Heldfond does not claim this was easy. Today, both are remarried. They have family dinners together, vacation together, and live only a few houses apart in South Tampa.

“It is definitely life changing going through a divorce but there is light at the end of the tunnel, especially with kids involved, you want to find that light a little faster. The hardest part of a divorce is usually the financial part for anyone no matter how much, or how little money, is involved,” DeBartolo says. “You can’t make finance break a bond. ” 

Asher loves to move from dock to dock and fish at his parents’ homes. His family calls him The Longfellow Creeper, Longfellow is the name of the street they live on. He often starts at his dad’s house and ends up at his mom’s, going back and forth several times a day.

Heldfond met Nadia Grannon while hanging out with his friend, Jeff Gigante, at one of Gigante’s restaurants off Howard Avenue in Tampa, Ciccio’s.

“Nadia walks in and she’s just gorgeous,” he recalls. “But behind her was this guy.”

Upon finding out the guy was just a friend, the usually shy Heldfond sparked up a conversation with him hoping for a chance to speak to Nadia.

Nadia was young, Heldfond had been through a divorce, it wasn’t a seamless relationship, but eventually Heldfond received some advice from an unlikely source. “It was actually Nikki who said to me, ‘You are an idiot, and you’re going to end up alone and miserable. You’re not going to find anyone better than Nadia,’ ” he says.

Nadia and Heldfond married in 2012. They have two children together—daughter Isabella and son Jackson. Nikki is married to Hillsborough County Sheriff Chad Chronister.

They have their own happy “Modern Family,” he says. “When I’m traveling, Nikki and Nadia hang out. Chad and I go to UFC fights,” Heldfond says.

That’s the idea behind Heldfond’s latest project, a book set to be released this year. “I hope the book will be an inspiration that there is another way through divorce,” he says. The book is co-written by Nikki.

Heldfond’s message is clear: Everyone has the power to change.

“I basically went from someone who just took and took, and lied, cheated and stole, to a somewhat-responsible person that gives to society now instead of taking,” he says. “And it was all because I put down drinking and drugging.”

Heldfond  now supports organizations that help addicts, such as Facing Addiction with National Council of Alcohol and Drug Dependence. The organization has 90 affiliates. Heldfond is on the board of the National FANCADD

He notes how different the process is now. In October 2018, Heldfond and Nadia made the trip to New York to attend the annual Facing Addiction with NCADD Gala.

“When I got sober, we were in smoke-filled basements in churches. Now, 24 years later, I’m at the top of New York City in the Rainbow Room, celebrating recovery,” he says.

Many professionals hide battles with addiction. If you or someone you know needs help, visit or call its 24-hour Hope Line at 800.622.2255.

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