Better off a College Dropout? What a few CEOs and Billionaires know that the rest of us don’t

Garreth Dottin
Habits and Design
Published in
6 min readJun 27, 2016

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Marc Zuckerberg, Steve Ballmer, Fred Moore, Larry Ellison, Bill Gates

There’s a certain story that’s pervasive in California — something that’s part of the culture’s bedrock: a kid drops out of school, becomes an entrepreneur, and goes on to change their industry (and eventually, the world). It’s part of the allure of the tech industry, and this almost mythic story has spread to our wider culture.

This story is certainly what drew me to the West Coast. As a native of New York, I was blown away by stories about these unlikely entrepreneurs who crawled their way from being almost nothing to industry titans.

But how authentic is this “successful dropout” story, really? I needed to know: was it just something cooked up in Hollywood for nerds to readily digest, or was it a real phenomenon. To understand this story better, I started by analyzing Forbes’s list of the 400 most successful people in the world and the 100 most successful in the tech industry. I wanted to understand what type of education these people had.

How many of them were dropouts and how many of them had a bachelor’s or a master’s degree? And more importantly were there unifying gifts or characteristics of these dropouts?

The First Hippie

Much of the story of the dropout surprisingly starts long before the dot com era. We tend to think Silicon Valley started with the 90s boom. The thought back then was that anyone with an idea and a garage could get millions of dollars in funding. (We’re looking at you, Pets.com.)

Marches used to be unheard of on college campuses

In fact, one can trace the origins all the way to the counterculture of the 60s. The era’s rebellious attitude towards convention would infect the early startup culture that grew out of Menlo Park.

John Markoff’s What the Dormouse Said catalogs the dropout culture originating at UC Berkeley, on the steps of Sproul Hall. In 1959, long before the 60’s really counterculture really kicked off, a freshman student Fred Moore decided he would be the first conscious objector to the draft. He started his protest by staging a hunger strike. For days he sat on the foot steps of Sproul Hall as thousands of students voiced their support and even more signed a petition objecting the draft.

Activists like Michael Rossman and David Horowitz, who would go on to define the counterculture era, recounted how astonishing it was to witness Moore. Moore’s hunger strike ended prematurely, as the Attorney General got involved and he eventually dropped out of Berkeley. But his story didn’t end there, he would later pop up again and play an instrumental role in the early days of the computer industry.

“If you want to speak about courage, speak about Fred Moore. He stood alone.” — David Horowitz

The Top 400

If we fast forward to the present day, we can observe that most of the ultra-successful people in the world attended college. This can be expected, as attending college is the standard in America and across Europe. But a small group of the Top 400, around 15%, are dropouts. High profile names like Bill Gates, Michael Dell, Mark Zuckerberg, and David Geffen stand out. The smallest group belongs to the dropouts, coming in around 15%, and the largest group includes people who hold bachelor’s degrees, coming in around 58%. While those with a master’s degree come at the middle, at around 37%.

Each group is graded on a scale as their categories are hard to definitively determine. Many of the wealthiest people are of course of an older generation, and information on their education isn’t readily available. By using text classification and a support vector machine, we can see that most of the people fall in a confidence interval above 60%.

The Drowned Worshipper

Illustrations by Haruka Aoki

Of course by glamorizing these high profile cases, we’re in part ignoring the elephant in the room. Most dropouts are less successful than their counterparts; they have poorer health and face more financial hardships. But in the news and even in data science, we have the problem Francis Bacon described as “the drowned worshipper.”

Those who die and those who never achieve success do not appear in the New York Times or the Wall Street Journal. They often don’t even appear in data sets, as people who aren’t successful are less likely to be accounted for. They don’t sign up for surveys or volunteer information as forthcoming.

It’s the same reason why the unemployment rate is almost always an underrepresentation.So we collectively see the successful entrepreneur and assume that a frequent case of a dropout entrepreneur involves an IPO and success story.

Although the myth of the dropout can be misleading, it’s still undeniable that many of the most successful among us are dropouts. And by looking at their stories beyond the data, we can see some of their apparent similarities.

The Traits

With many of the dropouts, from Fred Moore to Steve Jobs to Mark Zuckerberg, we detect a rebellious streak. In a story that’s now of legend, when Jobs was just a teenager, he and fellow Apple co-founder Steve Wozniak spent afternoons hacking phones and making international calls. By messing with the frequency of the phone, they were able to get a direct line to the Pope.

Fortunately, for Jobs (and the computer industry), he hung up the phone before getting transferred directly to the Pope. With Fred Moore’s after dropping out of school he would go on to found a band of misfits with the Homebrew Computing Club. Woznaik would later credit that club with inspiring the Apple 1.

“After my first meeting, I started designing the computer that would later be known as the Apple I. It was that inspiring.” -Woz

From Jobs’s Pope incident to Zuckerberg’s infamous Facemash, these people who would later become successful tech giants seemed too rebellious to fit into the rigid school system when they were students.

Along with this defiant behavior, the dropouts have a tendency for stubbornness and an unwillingness to have a group shape their behavior. For Larry Ellison, co-founder of Oracle, his defiance started early. While most young Jewish boys have a bar mitzvah, Ellison refused, stating that he didn’t believe in the faith and couldn’t morally go along with it. Such small acts of stubbornness keep coming up in the behavior of successful dropouts.

But perhaps the most important and obvious trait was prior success. The dropouts didn’t suddenly decide that school wasn’t for them; they had early track records. For instance, before Facebook, Zuckerberg created a music app that Microsoft tried to buy.

Dropping out of an academic institution clearly isn’t for everyone. I know I never seriously considered it. I personally waited to travel to San Francisco until I received that expensive piece of paper with my name and major on it. But there’s something we can glean from these giants: a certain exuberance and playful-yet-rebellious behavior. We can’t treat the dropout as the ideal circumstance for education but that doesn’t mean we shouldn’t admire it from time to time.

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Garreth Dottin
Habits and Design

Software architect, eCommerce expert, and ArborVita founder, Garreth works with fashion and wellness brands to foster longterm customer engagement.