The Unconventional Innovator Scholarship

When I was a student at Mineola High School, I had an insatiable curiosity about technology that went far beyond what was taught in the classroom. I taught myself programming languages, explored system administration, and tested boundaries in ways that weren’t always appreciated. Today, I’m excited to announce that Trail of Bits is establishing the Unconventional Innovator Scholarship at Mineola High School. This $2,500 award celebrates students who embody that same spirit of technological exploration and creative problem-solving.

From Troublemaker to Trail of Bits

My path wasn’t always smooth. While attending Mineola High School, I discovered a passion for technology that the curriculum simply couldn’t satisfy. I’d already learned Scheme and C++ through the Johns Hopkins Center for Talented Youth (CTY), then taught myself PHP, Perl, and Java. But the school’s tech offerings were limited to basic applications and graphic design. A well-meaning phys-ed teacher attempted to run a computer science class, but I often ended up teaching my fellow students instead.

Curiosity drove me deeper. I wanted to understand systems at their core, not just use applications. I needed to comprehend how they worked underneath. I set up my own web hosting service for about 20 friends’ sites, ran an internet radio station on ShoutCast where I played shows for my friends, and created a blog before blogs even existed. I was constantly pushing the boundaries of what I could create and manage with the limited resources available to me.

But being a teenager, I also put these skills to use in ways that raised eyebrows. I wanted to play video games during free periods, so I embarked on a multi-step journey: first learning Windows 2000 internals, then discovering PWdump to extract hashed administrator passwords, and finally using John the Ripper to crack those hashes. I set up Linux with Slackware and used Kismet to access the school’s wireless network, which allowed me to intercept traffic to their PowerSchool grading system. I discovered I could capture teachers’ login credentials through the unencrypted HTTP traffic and potentially change grades—a vulnerability I reported to the superintendent through my dad. I even brought my laptop in to demonstrate the attack live, for which the superintendent thanked me. I wasn’t vandalizing systems or causing harm. Instead, I was exploring capabilities, testing limits, and teaching myself skills that would later become the foundation of my career.

Unfortunately, these activities were met with suspicion instead of support. The school didn’t see the technical sophistication behind what I was doing. By my junior year, I was banned from using school computers after refusing to sign newly created acceptable use policies designed to preemptively restrict activities like mine. This even prevented me from writing for the school newspaper since the club met in the computer lab. In response, I built my own website and launched an independent student newspaper. This small act of creative problem-solving foreshadowed my future.

Mineola’s Transformation

Fast forward to today, and Mineola High School has undergone a remarkable evolution. In 2013, I began returning to speak at career days, first to high school students and later to middle schoolers as well. Eventually, the school hired Kuri DiFede to teach computer science classes, where I’d occasionally guest lecture on topics like the Little Man Computer (LMC) architecture and even basic exploit development. The LMC was how I first learned computer architecture at CTY, and it provided me with a fundamental understanding of how computers work that many students miss when they dive straight into programming.

As the program grew, I had to continually improve my material to keep pace with the students’ advancing knowledge. In recent years, in what feels like a beautiful twist of fate, the school hired Victoria Berkowitz to teach cybersecurity courses. Victoria earned her master’s in cybersecurity from NYU Tandon, the very program where I had served as Hacker in Residence, helping to develop the curriculum for graduate-level penetration testing and application security courses.

The irony isn’t lost on me: the high school that once banned me from computers now has dedicated cybersecurity classes taught by someone trained in a program I helped shape. I couldn’t be more proud of Mineola’s growth or more impressed with the opportunities that Victoria and Kuri are creating for today’s students.

The Recognition Gap

Despite this progress, I’ve noticed that something crucial is still missing. At the end of each school year, Mineola holds its Senior Awards Breakfast, where scholarships and recognition go to student government leaders and athletes. But students who demonstrate exceptional technical innovation—who teach themselves cutting-edge skills, creatively solve problems, and explore technological boundaries—often go unrecognized.

These students are developing abilities that can’t be taught in a traditional classroom. They’re showing initiative, resourcefulness, and determination that deserve celebration. Yet there’s no established pathway to acknowledge their achievements or signal that their passion can lead to exceptional careers.

This gap in recognition isn’t unique to Mineola. In researching existing scholarships for high school students interested in cybersecurity and hacking, I found shockingly few options. While there are excellent programs like the CyberCorps Scholarship for Service (SFS) for college students, we’re missing crucial support at the high school level, exactly when many future security professionals are first discovering their passion and developing foundational skills.

I experienced firsthand how transformative the right support can be. The SFS program I received in college dramatically altered my career trajectory. It connected me with a community of like-minded students focused on cybersecurity, provided specialized courses, and opened doors to meaningful internships. I had found my people, and I was challenged in ways that helped me grow. The lasting impact of this program was recognized when I was inducted into the SFS Hall of Fame in 2021, but more importantly, it shaped my understanding of how early support can accelerate a security career.

But why wait until college? Many of the best hackers I know started in their teens. By recognizing and supporting these students earlier, we can accelerate their development and help them avoid some of the obstacles I faced.

Celebrating the Unconventional

The Unconventional Innovator Scholarship aims to change that. This $2,500 award celebrates students who:

• Demonstrate self-driven learning and technical curiosity beyond the curriculum
• Show creative problem-solving and resourcefulness when conventional paths are blocked
• Constructively explore systems to identify hidden capabilities or vulnerabilities
• Persist in technical pursuits despite challenges or misunderstanding
• Apply technical knowledge to create practical solutions

In addition to the financial award, recipients will receive a copy of “Surely You’re Joking, Mr. Feynman!” This book tells the story of an irreverent physicist who embodied the spirit of curious, unconventional exploration. Recipients will also receive a personalized award letter acknowledging their achievements and encouraging their continued growth.

The selection process brings together Victoria Berkowitz, Kuri DiFede, and me to identify students who truly embody these qualities. I’m thrilled to announce that our first recipient is Joe Malone, who has demonstrated exceptional initiative in building his own game engine from scratch in C99 and participating in CTF competitions. Rather than using existing frameworks, Joe chose to understand systems at their core. This is exactly the kind of self-directed, unconventional thinking this scholarship celebrates.

A Broader Vision

This scholarship is just the beginning. I see it as part of a larger mission to accelerate Mineola High School’s trajectory and transform it into a powerhouse for developing technical talent. I want Mineola students competing with those from specialized technical high schools like Stuyvesant, Thomas Jefferson High School, and Brooklyn Technical High School. I want to see Trail of Bits interns from Mineola working alongside our engineers. I want Mineola students launching their own capture-the-flag competitions and winning national challenges.

To support this vision, we’re launching hackerspirit.org, which will serve as a home for information about the scholarship, profiles of recipients, and resources for students interested in security and hacking. If you’re a security professional interested in establishing a similar scholarship at your alma mater, I encourage you to reach out. With enough momentum, we could create a network of such scholarships nationwide.

Why This Matters

The security industry desperately needs more creative, boundary-pushing thinkers. The challenges we face are growing more complex by the day. By investing in students who demonstrate the hacker ethos of curiosity, resourcefulness, persistence, and creativity, we’re not just helping individual careers. We’re strengthening the entire field.

At Trail of Bits, we’re committed to raising the bar for security across the industry. The Unconventional Innovator Scholarship is an extension of that mission, recognizing that today’s unconventional thinkers will become tomorrow’s security leaders who protect our digital world.

For those students exploring beyond the boundaries, testing the limits, and learning what no one is teaching them, we see you, value what you’re doing, and are here to help you reach even greater heights. Your unconventional thinking is a strength to be celebrated and cultivated, not a problem to be solved.

If you’re interested in learning more about the Unconventional Innovator Scholarship or establishing a similar program at your alma mater, visit hackerspirit.org.