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Growing up in a first-generation, low-income household, Anaya didn’t have the grades or the connections. Known more for mischief than academics, he turned a corner only after marching into his high school dean’s office and pitching himself for another chance. The dean agreed to be his mentor and helped him find a roadmap to college.

Years later, on the other side of that journey, Anaya met José Antonio Tijerino, CEO of the Hispanic Heritage Foundation, who gave him a piece of advice that brought his own experience full circle: “If you can’t pass the torch to someone else when you’re in a better spot, then you don’t deserve to hold it in the first place.”

He took it to heart, and it remains the philosophy behind his edtech startup, Pupil, founded to guide high school students — especially first-gen, low-income and underrepresented teens — through the ups and downs of college application season.

“I was considered a failure,” Anaya said. “I built Pupil so other underestimated students could discover their untapped potential earlier and greater than I did.”

Pupil’s web and mobile platform fills the gap left by limited personal networks and understaffed school counselors. It connects students with undergraduate mentors using four filters: school, major, career interest and personal identity. Pairs meet over video once or twice a month, guided by built-in tools such as icebreaker prompts, goal-setting templates, session trackers and progress dashboards.

Anaya still remembers Pupil’s first mentee, Monica, a first-gen, low-income student who had never heard of programs like Matriculate or QuestBridge. With the high school-to-college playbook laid out by the platform, Monica earned admission to her dream school, the University of Pennsylvania.

Today, Pupil remains free for students like her who are eligible for free or reduced-price lunch, SNAP or Common App fee waivers.

“I stick to my ethics,” Anaya said. “I will never charge a low-income, first-gen student — because they’re incredibly valuable.”

A pivotal force in Pupil’s evolution has been NYU’s Leslie eLab. In high school, Anaya cold-emailed entrepreneurship programs across the country. Only NYU responded, which ultimately led him to Gallatin School of Individualized Studies, where he now studies economics, technology and philosophy on a full scholarship.

Through the Summer Launchpad accelerator, Anaya refined Pupil’s business model and strengthened product defensibility. Since launch, Pupil has grown to more than 560 mentors from over 105 universities, representing institutions from Harvard to Howard. The company is exploring partnerships with the New York State Education Department to make the program available statewide, with support from NYU research.

Still, for every mentor who believed in him, there was a message in his inbox telling him to give up and just focus on school.

“We’ve had doors opened and plenty slammed in our face,” Anaya said, quoting one of his favorite Steve Jobs lines, “Some years you win, and some years you build character.”