For Jay Fajardo, CEO of Proudcloud and co-founder of Launchgarage, some of the most valuable lessons on leadership and decision-making haven’t come from business school—but from books that explore the unexpected truths of human behavior and the timeless principles of ancient philosophy.
Jay’s reading list spans everything from technology history to startup science, but a few titles and thinkers stand out for how deeply they’ve influenced his mindset as a founder, mentor, and investor in the Philippine startup ecosystem.
One of them is Freakonomics, the bestselling book that challenges conventional wisdom using data and economic theory. “I also like Freakonomics, which shines a light on how human behavior is never what we predict it will be,” Jay told Financial Adviser PH. This insight has helped him develop an adaptive leadership style—one that accounts for the unpredictable nature of people, whether customers, teammates, or partners.
Jay’s perspective on social behavior and the nuances of human decision-making is also shaped by one of today’s most well-known authors: Malcolm Gladwell. “Malcolm Gladwell [is great] for deconstructing social dynamics and the world around us,” he says. Through books like Outliers and The Tipping Point, Gladwell’s storytelling has helped Jay think more critically about how success emerges from hidden patterns, timing, and context.
But perhaps the most surprising influence on Jay’s leadership is Stoicism, a philosophy that dates back over 2,000 years yet feels incredibly relevant in today’s fast-paced, high-pressure startup world.
“I listen to The Daily Stoic with Ryan Holiday,” he shares. “Stoicism has recently become a huge influence for me in how I deal with work and life in general.” The Stoic approach—focused on self-control, resilience, and accepting what can’t be changed—has helped Jay stay grounded while leading companies and mentoring founders.
The principles of Stoicism resonate with the way he navigates both uncertainty and ambition. In an industry where chaos is constant, Jay finds stability through reflection and emotional discipline. This has become especially important as he juggles the roles of builder, investor, and guide for early-stage startups.
Beyond these key influences, Jay regularly turns to tech chroniclers like Steven Levy and social commentators like Scott Galloway. “Steven Levy is a great storyteller and chronicler of tech history,” he notes. “I listen to Scott Galloway’s podcast as well for social commentary within the tech industry.”
Currently, he’s reading The Code: Silicon Valley and the Remaking of America, which dives deep into what made the region a global innovation hub. “It explains what unique factors led to the birth of Silicon Valley and how it became the nexus of tech innovation and pioneering ventures,” Jay explains.
Taken together, these books and thinkers reflect Jay’s multidisciplinary approach to leadership. He draws from history, economics, sociology, and philosophy—not just tech—to guide his decisions and inspire the founders he mentors.
What makes Jay’s insights particularly relevant for startup leaders is that they’re not rooted in formulas—but in understanding people. Whether it’s predicting consumer behavior, guiding a struggling founder, or navigating personal challenges, his playbook is built on curiosity, critical thinking, and timeless wisdom.
For aspiring entrepreneurs, his message is clear: Read widely, think deeply, and never underestimate the power of a good book to reshape how you lead, decide, and grow.
