For serial founder, investor, and startup ecosystem builder Jay Fajardo, leadership didn’t always come naturally. Like many early-stage entrepreneurs, he began his journey with a hands-on, outcome-obsessed mindset—one that leaned heavily into micromanagement.
“I used to be obsessed with outcomes, which made my first instinct to be micromanaging teams,” Jay shared in an interview with Financial Adviser PH. That tendency, while rooted in a drive for excellence, limited his team’s potential and placed unnecessary pressure on both himself and the people around him.
It took years of building companies, mentoring founders, and working with diverse startup teams for Jay to evolve into the leader he is today—one who empowers instead of controls.
As CEO of Proudcloud and co-founder of Launchgarage, Jay now works closely with entrepreneurs and tech teams to bring bold ideas to life. And his philosophy on leadership has dramatically shifted. “I’ve since developed the philosophy of hiring people better than you in certain aspects of business, particularly where my blind spots are,” he said. “This has led me to trust in my teammates more.”
That trust-first approach has become a key factor in how he builds and mentors teams. Rather than trying to be the smartest person in the room, Jay focuses on surrounding himself with people who are exceptional in areas where he isn’t. It’s a humility-driven approach that not only drives innovation but also cultivates a healthy, collaborative culture.
Jay also stresses the importance of team culture and fit over just raw skill. “I always believed in attitudes over aptitude. Competencies can be developed much easier than you can alter human behavior,” he said. This mindset has helped him build resilient teams with a shared purpose and emotional alignment—something that’s especially critical in the volatile world of startups.
But even as he leads with empathy and openness, Jay knows hard decisions must still be made. “When it’s clear that a team member isn’t a good fit, I’ve also learned to let them go,” he said. “Culture is important to team success.” That clarity and decisiveness in protecting company culture is something many leaders struggle with—but for Jay, it has become a non-negotiable.
His leadership style also benefits from a deep sense of awareness. “I’m obsessed about gathering information, news, trends, and input from around me, almost to a fault,” he admitted. “These ambient inputs and signals contribute to my ability to make rapid decisions, strategize, and make quick judgment calls.”
Whether navigating market shifts, mentoring first-time founders, or evaluating startup investments, Jay’s evolution from micromanager to trust-based leader has amplified his impact in the tech and startup ecosystem.
For those looking to grow as leaders, his advice is simple: know your limits, hire for your gaps, and don’t be afraid to trust your team.
It’s a lesson hard-earned through experience, but one that has shaped Jay Fajardo’s journey from coder and founder to one of the most respected mentors in Philippine tech today.
