Juan David Campolargo

PayPal Mafia

You've probably used PayPal to send money online.

But what you might not know is that several of PayPal's earliest team members went on to create or invest in some of the most iconic tech companies of the last 20 years, YouTube, Yelp, LinkedIn, Tesla, SpaceX, and Palantir, just to name a few.

This group, known today as the PayPal Mafia, shaped Silicon Valley in ways almost impossible to measure.

What’s especially interesting is that many members of this legendary group started their journeys at UIUC. People like Max Levchin (co-founder of PayPal and Affirm), Jawed Karim and Steve Chen (co-founders of YouTube), Jeremy Stoppelman and Russel Simmons (co-founders of Yelp), and Luke Nosek (PayPal co-founder, later Founders Fund and Gigafund) all spent formative years at UIUC before making history.

  • Max Levchin: Co-founded PayPal, Slide, and Affirm.
  • Luke Nosek: PayPal co-founder; later helped launch Founders Fund and Gigafund.
  • Yu Pan: PayPal founding engineer and first employee at YouTube.
  • Jawed Karim: Co-founder of YouTube, Airbnb seed investor, and creator of YouTube’s first-ever video, Me at the Zoo.
  • Steve Chen: YouTube co-founder and CTO.
  • Jeremy Stoppelman: Co-founded Yelp and remains its CEO.
  • Russel Simmons: Yelp co-founder and first CTO

Advice to Young People

1. Do Hard Things — Max Levchin

Remember that not everything hard is valuable, and not everything valuable is hard.

Create ambitious projects or companies that genuinely scare you.

2. Take Risks While You Can — Jawed Karim

Jawed paused his junior year at UIUC to join PayPal. Later, he encouraged others to take opportunities early, before responsibilities accumulate.

Your youth is your advantage. Use it.

3. Play the Long Game — Jeremy Stoppelman

Pick a mission you’d be excited to pursue for decades, not just the easy route or a quick cash-out.

4. Break Free From "Shoulds" — Luke Nosek

“My education was about the things that I do—not the things that they’re making me do.”

—Luke Nosek, quoted in Jimmy Soni, The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

Nosek reviewed the university handbook, identified the minimum graduation requirements, used exam scores to offset absences, and structured his time around the work he found most valuable. He graduated on his own terms. Treat rules as constraints to understand, not assumptions to accept. Always search for the hidden door.

Jailbroken Hacks

Start with small experiments. Before building companies that would reshape Silicon Valley, Luke Nosek, Max Levchin, and Scott Banister’s first venture was creating a T-shirt for the 1995 Engineering Open House (EOH).

Their first joint venture was a T-shirt for the 1995 Engineering Open House, a student-organized annual conference whose keynote speaker that year was Apple cofounder Steve Wozniak.

The trio bonded over producing something small, and it gave them confidence that they might one day make something big.

—Jimmy Soni, The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

Favorite Books

As they got to know one another, Nosek and Banister gave Levchin a crash course on libertarianism. The two had cofounded a libertarian student group, and Banister coded the group’s website.

Together they tried to indoctrinate Levchin, encouraging him to attend various libertarian events and read books like Ayn Rand’s The Fountainhead and Friedrich Hayek’s The Road to Serfdom. “[Nosek and Banister] were the subversives of our group,” Levchin said.

They were burning libertarian love. And I was just like, ‘Guys I just want to write some code.’ I always felt a little bit like the dumb Beatle.

—Jimmy Soni, The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

+1 on The Fountainhead!

Take Classes Outside of Your Major

Max Levchin's favorite class outside computer science was a film course.

He became obsessed with Akira Kurosawa’s Seven Samurai, watching it over 100 times.

Levchin’s class schedule was thick with technical coursework, but one of his nontechnical courses left a lasting imprint. In a film class, Levchin studied some of the twentieth century’s critically acclaimed motion pictures, and he became obsessed with Akira Kurosawa’s Seven Samurai. “I thought that it was the best movie ever,” he remarked. “I’d never seen anything like it.”

During a college summer, Levchin binged the three-hour-twenty-seven-minute black-and-white film with abandon. “All you’ve got is you, the TV, and air-conditioning… I watched Seven Samurai at least twenty-five times during the course of that summer. I got addicted.” As of this writing, Levchin claims to have watched Kurosawa’s classic over one hundred times—and calls it his sole source of “management training.

—Jimmy Soni, The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

Hide In Your Girlfriend’s Bathroom

Levchin did eventually manage to “acquire a girlfriend,” but his devotion to coding complicated the romantic commitment.

“I remember once coming over to her house and, right when I got there, going into the bathroom to write code.” Knocking on the door, his girlfriend asked, “What are you even doing here?”

“What? We’re dating,” he replied, confused at the question.

“No, this is not dating. You are coding in my bathroom.”

For Levchin, writing code—wherever he did it—was a singular source of wonder and insight. For the world, writing code was becoming a path to wealth and influence.

—Jimmy Soni, The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

That wasn’t the only time something like this would happen to Max.

My girlfriend at the time got so fed up with this, she broke up with me by ripping up my business registration certificate right in front of my face, to make a point.

Thing is, I didn’t mind too much, because that company failed already and I needed to register a new one anyway. I did, and it hurt exactly the same when that one failed too.

—Max Levchin, UIUC's 2018 Commencement Address

Alcohol & Bars

Levchin on his time at UIUC:

I have never been inside of a bar in my Champaign, ever.

I don't believe I had a single alcoholic beverage.

Need I go on more?

—Max Levchin, Fireside Chat with Max Levchin

Find something you really care about, so you don’t need to distract yourself.

Don’t Take Entrepreneurship Classes!

When asked how many entrepreneurship classes he took at UIUC, Levchin replied flatly:

“Zero.”

—Max Levchin, Fireside Chat with Max Levchin

What more do you need to know?

Entrepreneurship can’t be taught. You just have to do it.

So, how can you learn it? Later in the same interview, Max explains:

Entrepreneurship is one of these things you, there's only two ways of doing this. Two ways of learning it.

You can either just dive off into the deep end and do it and see what happens, and it is not a zero chance.

In fact, there's a pretty high chance that you're going to have a very hard time learning how to swim. Or, you've got about semi, you know, training wheels version of it, is you can join an early stage startup. And it's a little bit safer. But it could still fail.

You could still be jobless, but it's slightly less burdensome on you because you feel like you're sharing in a group of people's feeling of angst as opposed to just your own.

—Max Levchin, Fireside Chat with Max Levchin

Don’t waste your time taking entrepreneurship classes. Take hard classes. Take classes outside your major.

And if you want to start a company, just start it. You don’t need some useless entrepreneurship course to give you permission.

What I Took Away

I don’t include these people to say, “Look, UIUC is amazing because these successful people went there.” I couldn’t give two fucks, and you shouldn’t either.

The point is deeper (and more interesting).

These UIUC dropouts and alumni thought about college and life differently. I mention them not to glorify their success, but to highlight an alternative path, one you might not see in the day-to-day of campus life.

You don’t have to do what everyone else is doing. You don’t have to follow. You can think for yourself.

I bring them up so you can have more ideas about what’s possible when you challenge assumptions, find something you actually care about, and pursue it without waiting for permission.

Choose your own path, and if you can’t, create one.

Learn more

Front cover for The Jailbroken Guide to the University
Use the appendixThe back of the book is part of the book.

The appendix keeps the examples, guides, profiles, and source trails close. The book gives them sequence, context, and a way to turn curiosity into action.