Meet the Yale student and hacker moonlighting as a cybersecurity watchdog

Business Insider

20-05-2025

Alex Schapiro, a rising senior at Yale, likes to play Settlers of Catan with his friends, work on class projects, and lead a popular student website. But from his dorm room, Schapiro moonlights as an ethical hacker, uncovering security flaws in startups and tech companies before the bad guys do.
Schapiro's bug-hunting work gained traction last week after Hacker News readers had thoughts about one of his recent findings: a bug in Cerca, a buzzy dating app founded by college students that matches mutual contacts with each other. The flaw could have potentially exposed users' phone numbers and identification information, Schapiro said in a blog post.
Through an "internal investigation," Cerca concluded that the "bug had not been exploited" and resolved the issue "within hours" of speaking with Schapiro, a company spokesperson said. Cerca also reduced the amount of data it collects from users and hired an outside expert to review its code, who found no further issues, the spokesperson added. (The Yale Daily News first reported on Schapiro's findings in April.)
A frenzy of venture investment, in part fueled by advancements in AI, has hit college campuses, leading students to launch products and close fundraises quickly. And with "vibe coding," or using AI to program swiftly, becoming the norm among even the most technical builders, Schapiro is hopeful that ethical bug hunters can help startups build and scale while keeping security a top priority.
"These are real people, and this is real, sensitive data," Schapiro told BI. "It's not just going to be part of your pitch deck saying, 'hey, we have 10,000 users.'"
Building Safer Startups
Schapiro says he got his proclivity for programming from his mother, a former Bell Labs computer scientist. As many startup founders and AI researchers once did, Schapiro started building side projects in high school, using Spotify's API to curate playlists for friends and making X bots to track SEC filings.
Teaching himself how to "reverse-engineer" websites led to breaking and making them stronger — a side hustle he now uses to poke holes in real companies before bad actors can.
Ethically hacking is a popular side hustle in some tech circles. (A Reddit group dedicated to the practice called r/bugbounty has over 50,000 members.) It's a hobby that startups and tech giants stand to benefit from, as it helps them prevent data from getting in the wrong hands. Heavyweights like Microsoft, Google, Apple, and more run bug bounty programs that encourage outsiders to find and report security flaws in exchange for a financial reward.
In his first year at Yale, Schapiro found a "pretty serious vulnerability" in a company he says generates billions of dollars in annual revenue. (Schapiro declined to disclose the company, citing an NDA he signed.)
His discoveries have even led a company with "hundreds of millions of dollars in annual revenue" to start working on a bug bounty program of their own, Schapiro said. He has also been contracted by two other tech companies, including part-time work platform SideShift, to pentest their software. And last summer, he pentested Verizon's AI systems during an internship.
"As someone who uses a bunch of websites, I want my data to be taken care of," he said. "That's my mindset when I'm building something. I want to treat all the data that I'm dealing with as if it was my own data."
Joe Buglewicz for BI
Slowing His Roll
On paper, Schapiro seems like the archetype of a college-dropout-turned-founder: He has built and tested apps since childhood, and he runs CourseTable, a Yale class review database that receives over 8 million requests a month. Sometimes, Schapiro says, founders looking for a technical counterpart reach out to him, and VCs hoping to back the next wunderkind ask him when he's going to found a company.
For now, Schapiro isn't interested.
"The No. 1 thing stopping me from raising money right now is not funding," he said. "I would need to really invest a bunch of time in it, and I love the four-year liberal arts college experience."
Recently, Schapiro has found himself learning how to become a smarter computer scientist — not in a machine learning class, but in a translations course he took for his second major, Near Eastern languages and civilizations. It helped him think about how he turns English into Python efficiently and effectively.
"You meet so many interesting, cool people here, and this is a time in your life where you can really just learn things," he said. "You're not going to get that experience later in life."
While he's not ruling out the possibility of founding a company in the future, Schapiro is fine slowing his roll until graduation next May. This summer, he's interning at Amazon Web Services, where he'll work on AI and machine learning platforms.