According to Warsaw-based consultant Rudy Massimo, watching a kid interact at the skatepark is one of the best ways to identify if they have the potential to grow into a leader or entrepreneur.
That’s one of the many life lessons, leadership insights, and stories of adventures that Massimo shares in his recently published memoir Where the Trails Lead.
Subtitled “One man’s journey of adventure, adversity and leadership,” the memoir explores Massimo’s life from the streets of New York City to the peaks of South America and the outback of the Canadian north. Chronicling his life, it covers stories of adventure, shifting relationships, professional highs and lows, and the people who were there for him every step of the way.
“It’s become so much more than a memoir,” Massimo says. “Everyone takes something different away from the book.”
As president of Rudy Massimo & Associates, Massimo offer a range of philanthropic, leadership, and educational consulting services. He draws from his own background in leadership positions, including as executive director of Camp Kawartha for a decade, founder of Peak Adventures Inc., CEO of Outward Bound Canada, and a campaign leader for Lakefield College School.
These insights combined with his lifelong pursuit of outdoor adventures many can only dream of — dog sledding in the Yukon, participating in the Boston Marathon, and a year-long adventure climbing mountains to name a few — prompted his three adult children to encourage him to begin writing a book. It was only when his editor suggested his memoir might have a broader audience did he decide to print more than just three copies of it to give to his children.
Given that throughout his life Massimo was also hearing stories about his father’s experience as a post-World War II immigrant from Italy, he always wanted these stories to be documented as well. When Massimo’s father was just a child, he was separated from his family who had been displaced and, years later, sought to begin a new life in North America.
Massimo was inspired to include stories about his father as the opening chapter of Where the Trails Lead, while the final scenes of the book explore his own trip to Italy in 2022 where Massimo visited the collapsing, boarded-up, and war-torn home his father had lived in.
“I wanted to record some of that history from my father, but I also really wanted to trace back to where it all began,” Massimo says. “In each one of these homes, there’s a story. Someone lived in these homes, and I’m telling you my story and I suspect it’s the beginning of other stories to come. It goes full circle from my dad living in this home to having the sense of walking in his steps down these cobbled roads. That’s why it’s called Where the Trails Lead.”
The memoir explores Massimo’s childhood and teenage years in New York City, the discovery of his passion for sports and outdoor adventures, and the many lessons about death and falling he learned from exploring mountain peaks.
But woven throughout the story of adventure are stories of leadership, and some of the key pieces of advice he passes on to clients now, like the importance of early succession planning.
“I think people wait too long to talk about succession and leadership transitions and often those transitions are not smooth, especially if leaders stay far too long,” he says. “What happens then is their identity is so tied up with their title of CEO that they don’t like the thought that if they leave, they’re nobody — just regular Joe Blow from Idaho walking the streets. Being the head or the principal or executive director gives them purpose.”
“There’s nothing wrong with having a bit of ego,” Massimo notes. “But it’s dangerous when you can’t let go of it and, in fact, it could be detrimental to the organization that you love so deeply.”
In Where the Trails Lead, Massimo goes into more detail about a topic that he often talks and writes about, which is the belief that “there is no better activity in the world to identify (a child’s) potential to be future leaders than skateboarding.”
This, he says, is because there are no referees or whistle-blowers.
“Every single skateboard park is self-directed, so when you see the little guy going in he’s doing one thing and one thing only: he’s observing the culture, he’s observing the court rules for that skatepark,” Massimo says. “And once he’s figured it out, he jumps in and goes. No one cuts in. You have to figure it out as you’re going and that doesn’t happen in any sport.”
Massimo adds the skateboarding child fails nearly “99 per cent of the time” before finally landing the trick weeks later. He says this resiliency, dedication, and risk-taking is something they carry with them throughout their life.
“That tenacious behaviour is unprecedented,” he points out. “Sometimes they’re mentored by older kids, and when the kid lands the trick, the whole park explodes. It’s like the community celebrates that kid’s achievement because he was resilient, he had grit, he worked through the problem.”
Between these insights, Massimo tells stories of personal relationships, like the Magic Sugar Jaw he used to teach his children about manners and chores, and — the most difficult part of the memoir to write — the collapse of his marriage and reconciliation with his wife six years later.
But through poignant reflection, one thing Massimo does not shy away from in his memoir is admitting to the things he did not get quite right.
“I’ve done some pretty funky things in my lifetime but I’m not perfect and I made a lot of mistakes, and I share those mistakes openly,” he says. “We’re imperfect human beings.”
“I often read on LinkedIn about how great everybody is — ‘I’m great’, ‘I have top sales this month’ — but I don’t buy it anymore. I think we lose our sense of authenticity when we try to portray ourselves as being too perfect, and I think we’ve missed the boat in terms of what we’re looking for in true leaders.”
While readers are taking away different messages from Massimo’s memoir, from it being a love story to a guidebook on leadership, for Massimo it’s about the relationships that have shaped his life.
“I’ve summited mountains and I waved the flag at the top, but that’s not what it’s about,” he says. “It’s about the people that I’ve met, the journeys that I’ve been on with those people, and being able to still contribute to organizations I’m passionate about. I’m hoping I’ll continue to make a difference for the rest of my life in some small way if I can.”
Where the Trails Lead can be purchased at Happenstance Books & Yarns in Lakefield, online through Amazon, or by emailing Massimo at rudymassimo@gmail.com.
