In the face of immense adversity, some individuals find an inner strength they never knew they possessed. These individuals not only survive but emerge transformed, with their lives taking on new meaning and purpose. For John Ruffolo, a veteran of Canada’s tech industry, these transformative moments came in the most unlikely of places — first in his cocooned Italian upbringing in Toronto’s Jane and Sheppard area and decades later in the depths of a coma, hovering between life and death.
BY GIOVANNA G. BONOMO
October, 2024
To understand the depth of Ruffolo’s resilience, one must trace his story back to his beginnings in a humble Italian immigrant community in Toronto. Born to parents Anna from Fossacesia in Abruzzo and Santo from Rende in Calabria, Ruffolo grew up in a modest 1100 square foot semi-detached house in Toronto’s Jane and Sheppard area, a hub for Italian immigrants in the 1960s and 70s.
“It took me until age 4 to realize
I was not in an Italian speaking country.”
Ruffolo recalls with a chuckle. “Everybody thought everyone was Italian, and the only people who weren’t Italian were the ones you saw on television.” The Ruffolo household revolved around Italian traditions, especially those related to food and family. “September was the tomato sauce making, October was the wine making, January was the sausage and prosciutto making,” he reminisces. “The ritual of food and wine and family was emblazoned in our lives.”
These experiences, born out of financial necessity, instilled in him a deep appre- ciation for making the most of limited resources — a skill that would serve him well in his future career. “It was done out of financial necessity because they couldn’t afford [store-bought food],” Ruffolo explains.
“I would do anything to eat a hotdog or a hamburger, and it’s only upon reflection that I realize every meal was pasta, and I wanted to shoot myself.” He adds, “My kids would look at me and say, ‘Are you kidding? I would die to have that every day!’ It’s only a matter of perspective. It turns out that the food that was the classic core of Italian cooking is now the fancy cui- sine that’s loved all around the world. You didn’t have that perspective growing up.”
THE COCOON
Resilience is part of our heritage, and something I have lived on a personal level,” Ruffolo reflects. Growing up in a modest 1,100 square foot semi-detached house, Ruffolo learned early on that material possessions were not what mattered most in life. “We had the very basic essentials and a very tight family unit,” he recalls. “I learned that all the luxuries, all the material items, are not a big deal.
”However, growing up in this tight-knit community also presented challenges as Ruffolo began to navigate the broader Canadian society. “When I went to high school, my name was Gianni, and the first thing I did was change it to John so the teachers could pronounce it right,” he admits. “It was really an insecurity about fitting in.
”The growing tension between his roots and his ambitions came to a head when he joined Arthur Andersen at 20. “That was the moment I experienced cultural dissonance for the first time—feeling caught between two cultures, not fully belonging to either,” he says. The experience of being called a “Dago” by a colleague, though not intended maliciously, was a wake-up call. “It shocked me. I lived for the first 20 years of my life in this cocoon, and suddenly the racism card was dropped on me,” Ruffolo explains. “That was my defining moment.”
BEYOND THE STEREOTYPE
This defining moment became a driving force, propelling Ruffolo to the top of his field as an international tax advisor for mergers and acquisitions. “I would be on the other side of these folks who went to the best schools, and I went to the worst schools,” he recalls. “In my mind, I knew I had to prove I was more than a stereotype.” But success came at a cost.
A failed first marriage and a relentless work ethic left Ruffolo feeling disconnected from his roots. It wasn’t until his late 20s that he began taking annual trips to Italy that he experienced a shift. “It became the beginning of my Renaissance—back to my Italian roots and embracing my name, Gianni—and embracing my culture,” Ruffolo reflects. “There’s this beauty in Canada of order and meritocracy that you can’t find in Italy. But the lifestyle of living in Italy with that pure simplicity was something that very much attracted me.” This duality—the drive for success in Canada’s meritocracy and the longing for Italy’s simpler pleasures—shaped Ruffolo’s approach to business and life. “I always felt that trade-off,” John admits, referring to the tension between living a simple lifestyle and pursuing his ambitious vision of success in the Canadian context.
LESS IS MORE
As the Founder and Managing Partner of Maverix Private Equity, and Vice-Chair of The Council of Canadian Innovators, Ruffolo has played a pivotal role in transforming Canada’s tech landscape. His approach to business is deeply influenced by his upbringing, particularly the lesson of learning to do more with less. When advising founders, Ruffolo often asks them to distinguish between their needs and wants. In his experience, Europeans tend to be better at differentiating between needs and wants compared to North Americans. “When a founder tells me they need something for their business, I challenge them to reflect on whether it’s truly a need or just a want,” he explains. Ruffolo poses a simple question: “When you say you need this, are you really saying you want this, or do you absolutely need it?”
He finds that 90% of the time, upon reflection, founders admit they don’t really need it; they just want it. Ruffolo’s father, Santo, embodies this philosophy. “It was that ethos that I grew up with to the point today, and I still get criticized by my parents. I’ll give you a case in point: I am a big wine guy, and I will bring a fancy bottle of several hundred dollars and have my dad taste it. I’ll say, ‘What do you think? Let’s just say it’s a $500 bottle of wine’—I don’t dare tell him what the cost is because he would have a meltdown. He will say, ‘Yeah, it’s not bad, but my wine that I make for pennies on the glass is better than any of the stuff that you bring.’”
For Ruffolo’s father, the value of the wine isn’t in its price tag, but in the fact that he made it with his own hands. “The truth of the matter is, it’s not better, but it’s because it came from his own hands that he did it. Psychologically, he says, ‘It’s good enough. I don’t need that really fancy bottle of wine. I enjoy the pleasure of this good, solid bottle that I made out of my own hands, and it tastes better.’” This anecdote perfectly captures the essence of Ruffolo’s approach to business and life.
“That thinking and ethos has reflected the way that I operate my own business and the way I try to coach other CEOs in their own businesses.” In the tech world, Ruffolo’s Italian heritage manifests in his emphasis on relationships and community. “In an Italian family, you learn the importance of connections early on,” he says. “Whether it’s gathering for a meal or negotiating a business deal, it’s all about fostering genuine relationships.”
BRUSH WITH DEATH
In September 2020, a devastating cycling accident left Ruffolo paralyzed and fighting for his life when a transport truck struck him. “My first reaction was, ‘Oh my God, my kids are only 14 and 11,’” he remembers. “I had a spectacular life. A blessed life. I was prepared to die fully. I wasn’t angry; it was peaceful. And then I was like, ‘Oh Jesus, I have two little kids. I can’t do this; they need me.’” With an extraordinary force of will, and to the horror of those around him, Ruffolo tried to get up, not realizing that everyone thought he was dead.
“When they saw me moving, they were horrified,” John said. What followed was a grueling four-month recovery in the hospital, with doctors initially unsure if he would survive. But Ruffolo’s indomitable spirit, and the love and support of his family, carried him through. As he lay unconscious in the hospital on death watch, his family and friends held vigil, hoping and praying for his recovery.
Unbeknownst to them, Ruffolo was embarking on a profound spiritual journey that would change his life forever. “I had a vivid recall that I thought I had passed away and was going to heaven,” Ruffolo recounts. “I heard people clapping and cheering for me as I was ascending what I thought were the stairs to heaven, and I heard Bocelli sing. I thought, ‘Wow, this is incredible.’”
The experience was so vivid, so real, that Ruffolo could remember every detail. Two weeks after waking up, Ruffolo finally shared his experience with his wife Carryn, who never left his side and whom Ruffolo credits deeply for his recovery.“I said, ‘I got to tell you, I think I was going to heaven, and for some reason, I got pulled back.’” Carryn’s response left him stunned. “Oh my God, during your coma, I put headphones on you and played Bocelli live,” she revealed. “It turns out you can hear.”
This revelation was a turning point for Ruffolo. He realized that even in the depths of unconsciousness, the power of music and love could reach him. It was a testament to the unbreakable bonds of family and the resilience of the human spirit. When he finally returned home, Ruffolo and Carryn sat their children down to tell them just how close he had come to death. Their response left him speechless.“They said, ‘No, he wasn’t [close to death].
He’s been in so many accidents; he’s gone through so much. We never thought that was going to happen,’” Ruffolo recounts, still marveling at their reaction. “They just believed in the resilience of me living, when in fact, I was close to death.” This unwavering faith in their father’s resilience, even in the face of overwhelming odds, reflects the legacy Ruffolo had inherited and passed on to his own children. It’s a legacy that has carried him to the heights of success in Canada’s tech industry, and one that continues to inspire him every day.
Years later, Ruffolo’s experience in the coma also led to a beautiful friendship with Andrea Bocelli and his wife, Veronica. “I told this story to Andrea Bocelli and Veronica, and they were freaking out,” Ruffolo shares. “That’s how Andrea and I became good friends, because of this story.”
PASSING ON THE LEGACY
Today, Ruffolo takes pride in sharing and passing on his Italian heritage to Carryn and their two children, Caymus and Rome, bridging the gap between his immigrant roots and his Canadian success. “The simple pleasures of food, wine, and family,” he says, are central to this legacy. “My daughter, Rome, if she wants some great pasta, uses techniques she learned in Italy. She’ll make pasta from scratch with flour, eggs, and water, topped with my mother’s tomato sauce. Nothing is store-bought,” he says proudly. “Their pleasure in cooking from basics, rather than going to restaurants, surprised me.
When I grew up, I was dying to go to restaurants because that’s all I had. They have the luxury of going to restaurants, and they enjoy it, but they often prefer to cook at home. They say, ‘Can we make it at home instead? I know what I’m eating, it’s fresher, it tastes better, and there’s a sense of family.’ This sense of family around the kitchen table is the same thing I learned growing up.
My best memories were around the kitchen table, and my kids share that exact same ethos.” Ruffolo’s resilience, rooted in his Italian heritage and forged through a lifetime of challenges and triumphs, has not only carried him to the heights of success but has also transformed him in profound ways. His brush with death and spiritual awakening have given him a new perspective on what truly matters—family, heritage, and the unbreakable bonds they share.
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