On a cold, uncertain day in Argentina, Paolo Boero’s father made a decision that would forever change the course of his family’s life. With hyperinflation spiraling out of control, a looming military draft, and a nation teetering on chaos, he and his pregnant wife packed their lives into a few suitcases and left behind everything they knew. The destination? A place where opportunity seemed just barely within reach: the United States.
Arriving in a foreign land, Paolo’s father, a brilliant accountant who had graduated at the top of his class, was met with indifference to his credentials. His education, though exceptional, meant little in a country that valued American qualifications above all else. But starting from scratch didn’t deter him. Working entry-level jobs by day and attending night classes at Berkeley, he slowly rebuilt his career while supporting a growing family.
This deeply personal history laid the groundwork for Paolo’s own journey of perseverance and reinvention. In the latest episode of Navigating Complexity, we delve into how these family sacrifices, coupled with entrepreneurial grit, shaped Paolo’s outlook on life and business. A balancing act—between caution and ambition, risk and opportunity— a reminder of what it means to navigate complexity.
This foundation of strength and frugality left an indelible mark on Paolo. “I saw the sacrifices my dad made,” he shares, recalling how his father would save plastic bags and wear his shoes for years.
Following his father’s advice, Paolo began his career as an employee, learning the ropes of finance at UBS Investment Bank during the tumultuous 2008 financial crisis. He witnessed firsthand the devastation caused by poor planning and market volatility but also learned valuable lessons about contrarian thinking and the importance of liquidity.
“When others were pulling back, firms like Guggenheim were deploying capital,” Paolo recalls. This approach of calculated risk-taking would later influence his entrepreneurial philosophy.
Despite a promising start on Wall Street, Paolo always knew he was destined to carve his own path. He took the leap into entrepreneurship, first exploring ventures like starting a vineyard in Argentina with his father. While this dream ultimately proved financially unattractive, it reinforced the importance of pairing passion with sound business strategy.
Paolo eventually found his footing in real estate, co-founding a vertically integrated multifamily operation in Austin, Texas. Starting a business on the same day he began business school. One pivotal moment in his journey was meeting Matt McDonnell, a fellow entrepreneur navigating his own transition from the tech startup world to real estate. Their shared experiences and complementary skills would later spark a lasting partnership.
With limited resources, Paolo and his partners tackled everything themselves—from collecting rent to managing construction. Reflecting on this time, Paolo admits it was grueling but also invaluable. “It was about bringing efficiency to things that weren’t efficient,” he explains, describing how they turned underperforming properties into valuable assets.
Now, as a venture capitalist, Paolo applies the lessons he’s learned to guide and evaluate founders. He emphasizes the importance of scrappiness, resilience, and execution over charisma.
“Vision is important, but execution is what brings it to life,” he notes. Paolo gravitates toward founders who balance big dreams with a practical approach, focusing on short-term goals while leaving room for long-term growth.
As Paolo says, “You have to be comfortable taking a stance, even when others think you’re crazy. That’s how you find value in the long run.”
Join us in our next episode as Paolo shares more insights from his journey as a venture capitalist and offers advice for aspiring entrepreneurs looking to navigate their own winding roads.
To hear more of Paolo’s inspiring story and lessons on entrepreneurship and investment, check out his episode of Navigating Complexity on your favorite podcast platform.