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Alumni Connections

Catching Up

Stories from Hillbrook Alumni

Every student's journey after Hillbrook looks a little different - but throughout their college experiences, chosen careers, travels, discoveries, and new memories, one thing is certain: our alumni's post-Hillbrook adventures are filled with risk-taking, difference-making, and joy. And they never forget their Hillbrook days - or the way school changed their lives. We catch up with our alumni throughout the year, and share their stories in our Hillbrook Quarterly newsletter. Their stories are collected below. 

PS: Are you a Hillbrook alum and you'd like to see your story featured here? We'd love to hear from you - just send us an email!

Richerd Cancilla - Hillbrook's First Student

1930 - 2024
Generations of Hillbrook students have spoken about how Hillbrook feels like home - and this was never more true than for Class of ‘46 alum Richerd Cancilla, who passed away recently at the age of 93. Brought to our founders as a ward of the state when he was only three, Richerd became Hillbrook’s very first student, growing up among the oak trees and rolling hills of our Los Gatos campus. His life was expansive and rich with adventure - and throughout it all, his kind, compassionate nature never wavered.

Lucas (Class of '13)

After graduating from NYU in the spring of 2021, Lucas found work as a technician at UrbanGlass, one of the largest art studios in New York City; their sense of art as a joyful community experience has continued to expand in Lucas’s creative life. Read more

Gina (Class of '97)

You might not have noticed Gina Tirado Strayer Ma on her first day of school at Hillbrook. Today, Gina is known for her work at the ride-share company Lyft, where she was employee number one. Called a “female visionary” by Marie Claire magazine, she built out Lyft’s original driver community, and personally trained their first 500+ drivers. Read more


Alejandro (Class of '17) and Chris (Class of '15)

How does the Hillbrook classroom experience provide the tools a student needs for the future? For two of Hillbrook’s alumni, the answer is simple: the combination of math’s ability to discover a right answer with the soul-defining ability to take a risk – one of the four Core Values of our school, and perhaps the one with the longest reach. Read more

Faith (Class of '14)

Faith Chang has curiosity and drive. She’s willing to dive into the unknown to forge a path for herself. That path has taken her from Hillbrook middle schooler to Biomedical Engineer and Researcher and is launching her into medical school next year. Along the way, Faith has learned that when plans don’t work out — when she “fails” — what comes next can be surprising and wonderful. Read more

Julia (Class of '05)

Unflagging curiosity and desire to discover the world have been recurring themes in Julia’s life—a love of adventure and a faith in gut feelings that buoyed her through moments of triumph and challenge and into her current role at Bain. Read more

Gabriela (Class of '11)

Hillbrook alumna Gabriela Triant, class of 2011, is no stranger to asking questions about the world, being driven by her curiosity and her pursuit of excellence. Her MD plans include a master’s in public health and certification in bilingual medical Spanish so she can treat Spanish-speaking patients, which is important to her because of her family’s Salvadoran heritage. Read more

Ben (Class of '97)

When Ben Shanker was an eighth-grader at Hillbrook, hanging out with his friends on the upper field, he hadn’t yet imagined that he might be an anesthesiologist working in local area hospitals and clinics. What he did know is that Hillbrook always encouraged him to try new things, engage with learning, and do his best. Read more


Olivia (Class of '16)

When 2016 Hillbrook Award winner Olivia French returned to speak to the class of 2020 at their graduation, she encouraged them to take risks and explore who they are in high school. Now a sophomore at Georgetown University, studying Biology on the pre-med track, Olivia continues to follow her love of learning and desire to explore different disciplines, characteristics that were developed and encouraged in her time at Hillbrook. Read more


Bennett (Class of '11)

Head of School Mark Silver has been known to say to parents, “We’re preparing students for jobs that don’t yet exist.” Bennett Shaw has one of those jobs, working with cutting-edge genomic methods like CRISPR and next-generation sequencing to detect, diagnose, track and study infectious diseases such as COVID-19. Read more

Alex (Class of 2016)

Hillbrook graduate Alex Nickel (HB class of 2016) is going bananas, and he’d love it if you would watch. In truth, “Alex Goes Bananas” is the name of Alex’s new video series on Nebula, a streaming platform for educational videos. Read more

Will (Class of '10)

For Hillbrook graduate Will Belshé (Class of 2010), the grind never stops, but you won’t hear him complaining. He’s in his first year of medical school at UCLA and between lectures, labs, research, and exams, his studies are fairly all-encompassing. Read more

Stephen (Class of '99)

A pebbled leather ball and two metal hoops. These are the ingredients of some of the finest moments of Stephen Chang’s life. The Hillbrook alumnus’ love of basketball and his belief that the sport can teach important life lessons are behind his new children’s book, “The Basketball.” Read more

Nick (Class of '08)

In a first for Hillbrook School, one of our alums has gone platinum. Nick DiMaria, who plays guitar for country artist Devin Dawson, hit the platinum mark with the single, “All on Me”, meaning that the song has now sold more than a million copies. Read more

Aly (Class of '94)

Aly Wagner, who graduated from Hillbrook in 1994, became the first female analyst of the men’s World Cup of soccer on U.S. television. The achievement is one of many in her illustrious career. Read more

Sean (Class of '08)

Melting polar ice caps, rising seas, mounting garbage piles, droughts, floods, and wildfires – it’s enough to make a person cynical about the future. But not Rhodes Scholar Sean Reilly. Read more


Hayden (Class of '11)

Hayden wants to make you squirm. The 2011 Hillbrook graduate is studying film at the Tisch School of the Arts and the business of entertainment at the Stern School of Business at New York University with the goal of making horror films. Read more


Hillbrook Alumni - Stay in Touch!


Would you like to send our Alumni team an update? Share a Hillbrook story or memory? Or simply subscribe to alumni updates? Do it all here! Wherever you have taken your life beyond Hillbrook, we hope that you'll stay in touch - our doors are always open to welcome you home.

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