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The Startup: Pupil matches underrepresented high schoolers with university students and alumni mentors from partnered universities and organizations via an algorithm of commonalities.
The Founder: Dario Anaya (Gallatin ‘26)
Participated In: 2022 Summer Startup Bootcamp, VC Pitchfest
Dario Anaya grew up learning “grit, discipline, and consistency” as he worked long days for his father’s landscaping business each weekend and over summer breaks during his childhood years living in the Midwest.
And his penchant for entrepreneurship only continued to cultivate as he got older. In school, he made cash selling decorated glass candle holders to adults and rubber band bracelets, packs of gum, and bags of chips to classmates — teaching him early lessons about the power of supply and demand and the convenience that buyers are willing to pay for.
But despite his promising business savviness, Anaya says he was a troublemaker throughout elementary and middle school who was consistently underestimated by educators. In 8th grade, he applied to a top college preparatory high school, undeterred by his lack of the grades, finances, or behavior needed to attend the institution. His interview with the school’s Dean of Admissions led to an acceptance on academic probation and, later, a mentorship relationship that pushed Anaya to recognize his abilities and excel in his studies.
Inspired by his experience, Anaya started Pupil as a sophomore to help talented, underrepresented high school students discover their untapped potential by matching them with mentors at colleges based on their interests, backgrounds, and pursuits.
Today, Pupil is on the verge of launching its pilot in August with 150 low-income, high-performing students, and is actively recruiting 750 mentors. The startup is working with NYU Gallatin and NYU Stern to match high schoolers with college mentors. It is also in conversation with leaders at NYU Steinhardt and NYU Tandon, and has active traction from Cornell University, University of Chicago, and Claremont McKenna College.
Pupil has also landed the opportunity to co-host a four-part college panel series with the White House-founded Hispanic Heritage Foundation, and recently announced its Summer 2023 Growth campaign, where it will visit several NYC high schools to connect with students, share resources, and raffle off prizes.
Below, Anaya shares more about his founder journey and inspirations. (Responses have been edited for clarity.)
Q: What was your original concept for Pupil, and how has it shifted since the start?
Initially, I thought Pupil would be a one-stop-shop for high schoolers, offering internships, mentors, and student clubs — basically a LinkedIn, but for high schoolers. However, as we did more customer calls and research, we anchored on mentorship because it's what we understood best. In 2021, after we placed first in the StartEd Accelerator EdTech Week Competition and won our first $5,000 in non-dilutive funding, we spent 2021-2022 honing our product with customer and user insight and advisory while securing pilot contracts for our August 2023 launch.
Q: How did you initially find NYU's entrepreneurial community?
As a sophomore/junior [in high school], I cold-emailed Frank Rimalovski, the executive director of the NYU Innovation Venture Fund and Entrepreneurial Institute. I wanted his advice and guidance on my work with Pupil. Fortunately, he replied and gave me time. He treated me like an undergraduate student, answering my questions and guiding my thoughts. By senior year, Paul Horn, NYU's former Senior Vice Provost for Research, and Darren Yee, Venture Associate at NYU's Innovation Venture Fund, were also instrumental in my entrance to NYU's entrepreneurial community, as they would share their insight, time, and guidance with me on Pupil, too.
Q: How did your experience in the NYU Summer Startup Bootcamp transform the way you're approaching your venture?
The critical part: the user. The Startup Bootcamp really focuses on your customer and user. For Pupil, we're in a chicken and egg problem: to get the student, you need the university, and to get the university, you need the student. Through the Bootcamp, we learned to focus heavily on the customer, user, and our value proposition. We learned how to ask for and capture critical information from them to incorporate and reiterate so Pupil serves as a pain pill and not a vitamin to the issue. [We’re] helping universities get talented, underrepresented students, and helping the students discover their untapped potential and [get] into college.
Q: What is the biggest business challenge your startup has overcome so far?
It was how we will (1) incentivize mentors and (2) why colleges are ready to pay for Pupil.
No. 1 was difficult because most people like helping others, and not everyone only wants to help and not receive. Over more research, we learned how we can offer discounts, work-study, program credit, skillset building, awards/recognition, and volunteer service hours to our mentors on Pupil.
No. 2 was not difficult but tricky. Some colleges already get the best and brightest, so why Pupil? Well, we learned that while Brand Name Colleges do get the best and brightest, they lack exposure, community fit, and conversion rates regarding the best and brightest students from underrepresented backgrounds. This also applies to Non-Brand Name Colleges. Further, it's [based on] data and relationships, and relationships drive decisions. Pupil is that exactly — data and relationships-driven!
Q: What has been the most rewarding moment of your founder journey so far?
The most rewarding moment was this past December when Monica, Pupil's first mentee, texted me frantically. She had just been accepted into the University of Pennsylvania on a full-ride! It was really emotional for me. I had a big brother moment. Monica is a first-gen, low-income Latina student from the same district as me, Gary, Indiana. She worked hard, and through Pupil, we helped her discover and apply to Matriculate and QuestBridge, two of the most selective and prestigious pre-college programs in the nation. She was accepted, and she was most recently selected as a Hispanic Scholarship Fund Finalist among 125,000 applicants. That is why I started Pupil; that is why we work from dawn to dusk, and that is why you should always invest in the underdog — they make the best leaders, innovators, and scholars!
Q: Which successful entrepreneur would you like to get lunch with, and which NYC restaurant would you take them to?
Chamath Palihapitiya, founder & CEO of Social Capital and an early senior executive at Facebook. Since my sophomore year in high school, and still now, I’ve always relistened to his talk at the Stanford Graduate School of Business, "On Money as an Instrument of Change." His upbringing and work fuel me; his struggles and triumphs motivate kids like me from underprivileged backgrounds who still hustle to the top. I'd love to earn the chance to get lunch with Chamath at Piccola Cucina Uptown to learn from him and talk about Pupil and life.
Q: Favorite book?
The Go-Giver, by Bob Burg and John D. Mann. One of my closest mentors, Cal, gifted me the book during my junior year in high school, and it taught me the power of giving — not in a dramatic way, but how the genuine effect of giving releases impacts on your own life, work, and future.
Q: Favorite NYU spot to spend time?
Hands down, Rubin Hall, Pool Room in the early mornings and during the overall day. It's the best study, work, and chill spot with the sun shining through the enormous windows and (kinda) secluded-off space to work. That and laying in Washington Square Park, blasting music in my AirPods while I think of Pupil, school, and life.
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