Cory Levy was a college student at the University of Illnois when he tweeted at Keith Rabois, one of Silicon Valley's most prominent investors. Rabois replied, and that reply led to internships at Founders Fund, Union Square Ventures, and TechStars before Levy had graduated from college (though he dropped out anyway). By 19, he was able to raise $1 million in venture capital and co-built After School, a teen social app with over 20 million users. He successfully exited in 2021, when it was sold to Ancestry.com. Today, Levy runs Z Fellows, an accelerator that $10,000 to founders of any age to spend one week building an idea. He has bet almost one-fifth of the fund on teenagers.
When Matthew asked what he’d do if he were a high schooler again, Levy stated that he would first discover what he liked. Once he fully understood the field, it was then about finding the best person in the world at the field and how to get close and learn from them. He recommended a book as the framework: Mastery, by Robert Green. Having spent years studying prominent historical figures known as all-time greats in their respective fields, Greene concluded that figures like Darwin and Mozart were similar in that they found their passions early and attached themselves to people who were already masters of the field. Then, they built on what they absorbed.
Levy also briefly explained how he used the advice during his high school years. He worked for a startup during his underclassman years and began working at a VC fund his junior year, all through cold emails. Instead of waiting for his career to begin, he found his passion for entrepreneurship and got experience early on.
He told Matthew something else, too. As a high schooler, he deemed the ‘masters’ of his domain to be Facebook and Twitter, and was persistent on working for them even when it didn’t happen. Eventually, by working and shadowing for investors of Twitter and Facebook, Levy was able to learn from the masters by proximity.
A key insight he mentioned: if he were starting from scratch in his twenties, it’d be much more difficult. People are more likely to say yes to high schoolers hoping to learn and understand them over adults with an agenda. The advantage is real, and it doesn’t hold forever.
