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The Anti-Dropout

Or, Why I’m Going Back

The Anti-Dropout

Or, Why I’m Going Back


Since dropping out of college at age 20, I’ve been a vocal proponent of “Career Hacking” and other approaches that lead to departing from the standard education path. College was a frustrating and limiting experience, while my time since dropping out has been universally positive. I worked for David Tisch and the inaugural class of TechStars NY, joined Onswipe as Employee #2, and most recently was one of the first US employees at Taykey. At each of these roles, I’ve been privileged to be surrounded by smart people solving hard problems — exactly what I hoped to find when I left college.

That’s why it’s coming as a surprise to many of my friends that I am returning to my studies this fall. I’ll be studying Computer Engineering at Columbia University, attending as a full-time student.

Why am I doing this after successfully dropping out? Because two truths have become apparent after spending two years working in tech:

The most interesting technical problems of the next decade won’t be solved in areas of knowledge that can be self-taught, and most technical knowledge remains locked up in traditional academia.

Part of the fetishization of the dropout over the past few years has been the assertion that smart people can “teach themselves” the skills needed to succeed in technology and business. I take issue with the fact that this implies all smart people are autodidacts (not at all the case in my experience). It also implicitly argues that all “important” knowledge can now be found online in a readily digestible format.

It’s true (and exciting) that so much knowledge has moved online in the past decade. I can learn basic programming via Treehouse. I can learn web design in a course on Udemy. But what if I want to learn about the physics that drive hardware performance? The materials science behind the next generation of wearable computing? Or what about how to bring electronics manufacturing back to the United States? There are real, fundamental sets of knowledge that are still locked up in traditional academia.

We can debate the merits of this, as well as how quickly this knowledge will go “open source,” but as a 22-year-old in 2013, I’m not willing to bet my career on that time frame.


The next generation of innovation will come from larger organizations, where traditional credentials are more highly valued than in degree-agnostic web tech startups.

I believe that the next set of world changing innovations won’t necessarily come from the same team structure that has thrived over the last 5+ years. The default mode has been a small, nimble team, with limited resources (angel-financed seed round) building products. This is a great model when you are building on the back of commoditized tech or open sourced frameworks.

This won’t necessarily be true in the next generation of innovation. We forget that the technologies underpinning the current generation of startups began in huge organizations (Xerox, IBM, Apple) before being iterated upon in smaller teams and organizations. The past few years have seen a large reallocation of resources to the “iterative” end of the spectrum, which leads me to believe we are due for a swing back to investment in the “fundamental” side.

What does this mean in the context of education? It is in those types of organizations that credentials do matter. Want to work on the self driving car? That Ivy league engineering credential is your ticket onto that sort of team. I won’t bet my career on beating the HR apparatus at Google, even after I have proven my ability to hack my way onto early startup teams.


I’ve now twice expressed an unwillingness to “bet my career,” which probably seems oddly conservative for a college dropout. I’ve always admitted to being the most risk-averse dropout around. Just like the smartest gamblers do everything to stack the odds in their favor, I want to place smart bets in high-impact areas. My decision to drop out was a gamble that I could find success through my own educational framework. Going back is a way to double down on the experience I’ve gained over the past two years — I’ve seen the cards, and I’m ready to place the next bet.