On April 28, 2025, San Antonio Academy welcomed back alumnus Stephen Trippy, class of 2010, for an Alumni Monday visit filled with gratitude to the school, his family, and mentors who helped shape his path.

Reflecting on his time since arriving at The Academy in sixth grade, he recalled the three guiding principles he learned: "Be honest. Be kind. Be the best you can be."® These lessons proved invaluable both during and after his school years.

He shared a memorable story from seventh grade when a misguided attempt to kick a basketball into a bin ended with a shattered third-story window. Despite the temptation to hide the accident, he confessed immediately, an act that taught him the lifelong value of honesty, even at personal cost.

Stephen then detailed his post-Academy journey, including challenges he faced in college in Houston, struggles with direction, and ultimately dropping out—a daunting but necessary decision at the time. After surviving Hurricane Harvey, thanks to the kindness of strangers, he rebuilt his life by working as a restaurant server, finding unexpected joy in serving others and dreaming of a culinary future. However, when the COVID-19 pandemic halted the restaurant industry, he seized the opportunity to return to college with a renewed sense of purpose.

Now working in ship inspection—a job that combines his love of math, writing, and helping others—he emphasized that embracing change and uncertainty is essential. He encouraged the boys to stay true to The Academy’s foundational values: honesty, kindness, and perseverance. “Not knowing what's coming next isn't just okay—it's guaranteed,” he reminded them. “And that's what makes life exciting.”

About Alumni Mondays: Each Monday, we welcome an Academy alumnus to speak to SAA boys during chapel. During this presentation, our alumni speakers share meaningful stories and lessons from their days at SAA. View Alumni Monday Showcase