Elevated Podcast Episode 3 with Rocco Cortese – From Grit to Growth
From Grit to Growth: Rocco Cortese’s Journey Through Real Estate, Resilience, and Reinvention
In episode three of the Limitless Growth Podcast, we sit down with EO San Diego past president Rocco Cortese, the founder of Intersection, a multi-division real estate firm. What unfolds is not just a career-spanning conversation—it’s a deeply honest account of reinvention, resilience, and what it means to keep pushing even when life doesn’t go to plan.
From Immigrant Roots to Real Estate Roots
Born in Canada to Italian immigrants, Rocco moved to the U.S. in 1977 and eventually landed in Southern California, attending San Diego State University. While he dreamed of a career in advertising and marketing, he initially stumbled into commercial real estate through a friend’s connection. “I was sleeping on my brother’s couch and selling shoes,” he recalls. One job interview led to another—and soon he was working at Coldwell Banker (now CBRE).
But the corporate path left him unfulfilled. So he did what few have the courage to do: he quit and spent nearly two years traveling the world—pre-cell phones and GPS. This time away gave him perspective, shaped his worldview, and grounded his love for urban environments and towering skyscrapers.
“I always loved being in big cities. Something about buildings and infrastructure—it stuck with me.”
Starting Over and Building Intersection
Rocco’s second act began in earnest after his travels. Settling in San Francisco, he reentered real estate with fresh energy and clarity. It wasn’t long before he hit his ceiling at a corporate job and decided to build something of his own.
In 2003, Rocco co-founded a commercial brokerage firm. But the 2008 financial crisis hit hard. “Those were brutal years,” he says. “We had just moved to San Diego, bought a house at the top of the market, and suddenly the entire real estate world collapsed.”
Despite the pressure—raising three kids, trying to stay afloat financially—Rocco refused to quit. He kept grinding through 2009–2013, slowly regaining his footing. In 2014, he and his longtime partner merged their operations and formed Intersection—a full-service, vertically integrated real estate platform that includes brokerage, property management, investment management, and facility services.
PTSD From the Crash—and the Long Shadow It Cast
Even with business success, Rocco admits that the trauma of the 2008 collapse lingers. “I still have PTSD,” he shares. “Even when things are going well, I have a hard time believing financial stability is real.”
The pressure affected more than just the bottom line. “I was there with my kids—but I wasn’t present,” he says. “I coached soccer, but I barely remember it. I was in survival mode.”
His personal finances tightened, and dinners at McDonald’s became a norm during the toughest months. Yet, through it all, he never stopped showing up for his family or business.
EO: The Turning Point
Joining EO in 2015 changed everything.
“I realized I had a right to a life. I didn’t need to carry the weight of the world every day.”
Through EO, Rocco found a community of entrepreneurs who truly understood the grind and the loneliness. Forum became his safe space. It gave him permission to pursue joy, not just success.
He later became chapter president, an experience he describes as life-changing. “I wasn’t the kid who owned the sandbox—I was the kid getting his ass kicked in it. EO gave me confidence.”
Learning to Focus—and Learning from Failure
Throughout the years, Rocco has made plenty of business decisions, not all of them perfect. One major misstep? A non-refundable $500K deposit on a hotel deal that never closed.
“We had no business buying a hotel. I’ll never go non-refundable again without inspections. Lesson learned.”
But he’s also refined his approach. Today, Intersection only acquires industrial properties—choosing focus over fragmentation. That singularity of purpose has strengthened the team, operations, and long-term vision.
Intersection now comprises four thriving business units: brokerage, property management, investment, and facility services—providing stable, diversified income. But more importantly, it’s built for scale and succession.
What Drives Him Now
Once fueled by fear of failure, Rocco’s motivation has shifted. Today, he’s driven by purpose, freedom, and mentoring the next generation of leaders within his business.
“I’m 60 now, and I’m becoming more interested in what life looks like when I’m not constantly pushing. I want to build the future leaders at Intersection—and create room for myself to explore what’s next.”
With one child already through college and another special needs child at home, Rocco’s purpose remains deeply rooted in family. And while he’s currently navigating a divorce, he’s facing the transition with grace and optimism.
Looking Ahead
In three years, Rocco envisions stepping back from the day-to-day grind, focusing on visionary work, and potentially preparing Intersection—or its parts—for acquisition. He also hopes to spend more time mentoring younger entrepreneurs and giving back to the community that’s given him so much.
“I want to look back on a body of work and say, ‘I fought through it. I built something. And I helped others do the same.’”
Rocco’s story is one of grit, humility, and evolution. From typing resumes on a typewriter to running a diversified real estate enterprise, he’s proof that every chapter of the journey matters—even the hard ones. As he reminds us, the best growth often comes through the toughest lessons.
Stay tuned for more stories of resilience and transformation from the EO San Diego community on the Elevated Podcast.
