Juan David Campolargo

Keith Schacht

When I first met Keith Schacht, I was surprised by how much we had in common:

  • We both went to the University of Illinois.
  • We both felt similarly frustrated with typical college classes, preferring instead to find interesting classes and talk to interesting people.
  • He didn't initially get into engineering, and neither did I. We both had to re-apply after our first year.
  • He was a Resident Advisor (RA) at PAR—the same dorm where I was an RA at the time.

So when Keith stumbled across my website and emailed me out of the blue during my sophomore year, it changed the trajectory of my college years in a very real way. Every conversation we had immediately shifted the way I approached things.

At the time, I was annoyed with school. It was the first semester of my sophomore year, I was a Resident Advisor at Pennsylvania Avenue Residence Halls (PAR), and taking PHYS 212 (Electricity and Magnetism, a notoriously tough class). I wasn't excited about school. I was also struggling to figure out what I even wanted to study or do next. So when Keith reached out, he reached out just at the right moment. It came when I was already questioning most of what I was doing.

After that initial conversation, everything changed. Over the next several months, I started a number of projects that ended up defining my college experience, including the UIUC Talkshow and UIUCFreeFood. Keith's perfectly timed email was a turning point.

Throughout college, Keith became one of the most influential people in my life. When I was on disciplinary probation and my standing at the university felt uncertain, Keith and I would talk for hours, his clarity always amazed me. He has this ability to get unemotional, see all the options, and pick the most exciting one. He has inspired me in countless ways: guiding me through the ups and downs of starting startups, thinking about technology, learning how to manage your own emotions, and so much more that I'll share below.

I was already jailbroken, but Keith showed me I wasn’t the only one. He showed me there were other jailbroken people out there who thought differently, questioned everything, and dared to take unconventional paths. Keith was one of those people. He fundamentally changed the way I experienced college, and I know after reading his thoughts below, he will do the same for you.

Short bio

I've started many companies and sold a few. My first was in college; I sold it my junior year and dropped out. My "first love" was Inventables. It opened many doors like speaking at TED, meeting amazing people, and it had a modest outcome. My biggest success was Mystery Science (YC S17). I co-founded this with Mystery Doug, and it became the most widely used science curriculum in American schools (and outside of school, kids have viewed videos hundreds of millions of times on YouTube). This business had a great sale to Discovery Education in 2021. As part of this deal, I spun off a side project to continue working on it as a new company: The Explanation Company. We were building a voice AI app for kids to get great explanations to all their questions. We had a great founding team, and raised $10M from great investors led by a16z, but I failed to turn this product into a success. Product-market fit is hard, even after achieving it multiple times before.

—Keith Schacht’s Blog

Favorite Book

Atlas Shrugged by Ayn Rand

See Classes as a Menu in a Restaurant

One thing that helped was that I roughly knew what I wanted to do with my career when I got there. I loved building things, all kinds of things. But in particular I like building companies, I like programming, and I like building products people use.

So I found all the classes that I thought would teach me interesting things that might be useful, and I found all the professors who were particularly good teachers and considered taking classes from them.

I actually figured out a way to not take required classes that I supposedly needed as pre-reqs for my major, if I thought they wouldn't be a good use of my time.

—Keith Schacht, from a personal email exchange

You come to college, you choose a major, and then you take all the classes your major tells you to take.

But wait....??? What about your own interests? The things you're actually curious about? The things you genuinely want to learn?

Typical college counselor answer: “Electives! You can take electives and align them with your interests.”

Cute.

Here’s what’s actually going to happen. You'll be stuck taking required courses you couldn't care less about, and by junior year (more like the last semester of your senior year), you finally can pick some electives. And guess what? You quickly realize the electives have nothing to do with your interests. Even worse, by that point, you’re usually so tired and disinterested in school, you just want to be done. You’ve lost track of your interests because you spent all that time ignoring them.

This scenario happens way too often.

But it doesn’t have to be that way.

You can look at classes differently. Think of the university as a big, amazing restaurant, and the classes as a menu. You can choose whatever dishes look interesting to you, whatever makes you hungry to learn. You are the one who chooses, not your degree requirements.

Your interests are sacred, and they’re sacred for a reason. Trust them. Trust yourself.

Keith had interests, and he chose classes and professors based on whether they would help him explore those interests in more depth. Sounds reasonable, right? Well, pretty much no one does this, but know this is an option!

In one of my calls with Keith, he told me a story I will never forget. We all know the famous story about how Steve Jobs dropped out of college. But what fewer people realize is that he didn’t drop out, he "dropped in."

Yes, Jobs dropped out of required courses, but he still attended college classes. Instead of doing the typical route, he audited whatever classes caught his interest. One of those classes was calligraphy. You might think, "Calligraphy? That seems pointless." Yet it was that very class that inspired Jobs to design Apple’s famously elegant typography.

What Steve Jobs did is an example of the true purpose of college: not simply to get a degree, but to figure out what genuinely excites you and to figure out what you want to do for the rest of your life.

How to Not Take Required Classes (or Other Classes You Don’t Want)

After reading the previous section, you’re probably thinking: Wait, what? Keith figured out how to skip classes he didn’t want to take? How!?

Here’s how Keith described his approach:

When I was in college and there were required classes that I didn’t want to take, I figured out that I could skip the classes by testing out of them.

I just asked the department how I could demonstrate mastery and typically they’d tell me if I could pass the final exam they’d give me class credit, but not a grade.

It was much easier to study for a couple days to pass a final than to sit through a whole semester of soul-killing lectures and wading my way through boring assignments.

Avoiding required classes was door #4 that most students assumed was not possible. I also applied this trick to enroll in classes that I wanted to take but were full. Even a full class always has open seats because someone doesn’t show each day. I’d happily attend every class and do every assignment that was interesting, skipping the ones that seemed pointless.

All I had to do was pass the final to make the university happy. It didn’t matter that I was not enrolled in the class.

—Keith Schacht, Behind door #4

I did this many times myself, and yes, of course, it works.

But here's a funny story you'll find interesting: one time, after using this exact strategy, a professor actually told me to drop out—not just of his class, but of college entirely! It wasn’t encouragement, he went completely bananas. (Long story!)

So keep looking for alternative doors. Don’t stop knocking until one opens.

Graduating Doesn’t Matter That Much

Keith has always been an entrepreneur, but at some point, he wanted to join what would soon become one of the biggest companies in the world—Facebook.

He had never written a resume before, so he sat down and quickly put one together. But remember, Keith dropped out of college and never completed his degree. On his resume, he listed his major and the university he attended, no mention of graduating.

What he realized was that most people automatically assumed he had graduated. If interviewers asked him directly, "So what year did you graduate?" He would explain he had dropped out, and their reaction surprised him because they actually congratulated him!

Everyone usually says graduating from college is important because it signals you can accomplish something difficult.

But that makes no sense.

Keith’s example is a perfect example: dropping out wasn’t a sign that he couldn’t do something hard. Instead, it signaled someone who could think independently—someone who recognized that college, at least for him, didn't make sense and wasn't worth doing just for the sake of appearances.

The real questions are: Do you have skills? Do you know how to learn? Can you actually do things? That matters more than any diploma.

In the end, Keith got the job.

Advice to Young People: Overcome Your Internal Resistance

Figuring out what you want to do is only half the battle. The other half, often much harder, is overcoming the internal resistance that stops you from actually doing it.

Sometimes you know exactly what interests you, but for some inexplicable reason, you still can’t make yourself take action. Maybe you dream about starting a project, writing something, or launching an idea, but instead you hesitate, procrastinate, or talk yourself out of it. It’s not always external obstacles that are stopping you. Sometimes, it's yourself.

Keith taught me a really interesting strategy about how to overcome the internal resistance to doing what you want. He explains it below:

The way you put it: “figuring out how to overcome internal resistance to doing what I want.”

That sounds about right.

Many changes I wanted to make took years before I fully overcame the internal resistance.

I found “thinking on paper” to be one helpful technique. I don’t know if you’ve ever done it before, but the basic idea is: sit down with a blank sheet of paper and a real pen/pencil (not a keyboard). Write out your whole inner monologue. It might start out like this:

“I thought I would be really excited to do _but now that I am actually making the decision, I am not feeling excited. Why is that? Is there something I’m afraid of? I can’t put my finger on anything in particular. What aspect of this am I hesitant about? If I could do it with someone else, maybe that would make me feel different. I could think about inviting ___. But no, as I imagine that, I think I would still feel the same. Is it that I don’t really want to do it? Maybe if I remind myself of why. First…”

I literally write down everything that is popping into my head. I write down the questions, then I answer the questions. It’s a bit like having a conversation with myself. However, by writing it with my hand on a real piece of paper it forces your thinking to slows down your thinking. If my thinking is stuck in a loop, it makes it much more evident to see. If I get stuck in my thinking, I can re-read back in the last 60 seconds and then new ideas and thoughts occur to me.

This technique is no cure-all, but often it helps me get underneath a feeling. Often it helps me identify a premise that I have and once I can question the underlying premise that’s the beginning of changing the feeling. But it’s a slow process.

But I’ll also say that there is a saying “fake it until you make it.” I actually hate the saying, except there is one aspect of which I think is accurate. When I have some feeling which is holding me back. Once I’m able to identify the source of the feeling, it doesn’t make the feeling go away. It can still take months. But I will allow myself to ignore the feeling, push through it, pretend like I’m not feeling that resistance even when I am. I don’t do this lightly, I only let myself do this when I feel like I understanding the feeling and consciously want to change it.

—Keith Schacht, from a personal email exchange

Ever since Keith shared this technique with me, I've used it countless times, having conversations with myself to clarify my thinking.

Figuring out what you love is step one, but learning how to overcome the barriers within yourself is the crucial next step to actually doing it.

Being an RA (Resident Advisor) is CEO Training in Disguise

Juan David: I just remembered you were also an RA at PAR. Just finished RA training, and school is starting the following week. What did you think of RA training back in the day?

Keith: I remember that RA training. I remember it felt mostly pointless. I get why they had to do it, but I remember that it was mostly just getting to know the other RAs.

My biggest takeaway from the whole RA thing was being annoyed regularly that, on the one hand, I was trying to build relationships with my residents and, on the other hand, I was this rule enforcer. It was an interesting dynamic to try and navigate. Now, running a company, it's notable that I've continued to navigate this dynamic ever since! So it was actually a good early taste of this challenge.

—Keith Schacht, from a personal email exchange

Instead of treating an RA role as just another job, I realized it was actually an opportunity to practice running a company.

After that, I stopped seeing my RA duties as chores. Every moment became a valuable chance to reflect and build skills I knew would help me in my future companies.

The Infinite Combinations Principle

I hold this premise very explicitly: that for any combination of interests you have, there is a career out there that could contain those combination of interests. So if you like cooking and you like sailing you could be a chef on a yacht.

—Keith Schacht, Inside ARU: Philosophy and Work

Don’t limit yourself based on what you think is possible. There are always more options than you realize. Start by identifying what you actually enjoy, then look for ways those interests can overlap, even if the path isn’t obvious.

The great tragedy for young people is prematurely discarding parts of themselves, simply because the world—or someone else—told them their interests don’t combine neatly into a career. Imagine someone who loves filmmaking, computer science, and art history, but focuses solely on computer science because they assume these things can’t fit together. Too many students give up on what excites them before even trying.

Always try first.

One of my favorite Keith stories illustrates this idea:

I had an apartment and I signed a one-year lease... I had like five months left and I wanted to move out early... I posted the apartment on Craigslist and I listed it at a higher rent than my current rent... I found someone and I walked down to the management office with the person and said 'Hey I know you wouldn't let me out of my lease but I found someone who's willing to rent it and they'll pay this much' - now he let me out of the lease.

—Keith Schacht, Discovering Your Passion, Creating a Career

In that story, the constraints everyone assumed were fixed turned out to be negotiable. When circumstances change, you can always challenge these assumptions and find new solutions.

The same principle applies to following your dreams, combining your interests, and tackling just about anything else in life—there's always another door.

How Do You Actually Find What You Love?

Keith understands how tricky this can be:

It seems odd to ever be in a situation where you don't know what you love because it seems like it should be so easy to know what you love but I'll tell you it's hard. The voices in your head of what other people expect of you and what your parents want of you and what society has crowned as prestigious... those voices are so loud and the voice in your head of what you're interested in and what you might find fun - that's a really soft voice.

—Keith Schacht, Discovering Your Passion, Creating a Career

Keith’s approach was to ask himself a simple question:

What do I love doing with my time when I'm taking a break from work and from school, you know, just on the weekend?

—Keith Schacht, Discovering Your Passion, Creating a Career

So what did Keith actually do?

He gave himself permission to follow his curiosity without trying to optimize for outcomes. At one point, he:

  • Spent all day at the library reading back issues of Popular Science:
    • “One of the first things that came to mind is, well I loved reading Popular Science magazine... I hadn't read it for a couple years. I'd been so busy with school and with this company and so I went to the library all day and I just read every back issue that I had missed out on over the last couple years and it was awesome.”
  • Absorbed himself in video games for days:
    • “I had a point where I'd loved playing video games and so I found a new video game and for a few days that's all I did, I just absorbed myself in it.”
  • Wandered bookstores noticing what caught his interest:
    • “Then I went to the bookstore and I just wandered a whole day around the bookstore and just noticed what sections caught my interest, what titles, and I just pulled a book off the shelf and read it for a couple hours and I just absorbed myself in this.”
  • Made a list of childhood interests and revisited each one:
    • “I started getting more systematic about it. I made a list of all of the things that I'd loved doing in my childhood—origami and Legos like they were on this list—and I just systematically revisited each of those and some of them were just for a day and some were for a week but I was very intentional trying to remind myself what was it that I loved about this, like what attracted me to it in the first place.”

Notice what Keith didn’t ask himself:

  • What would make me the most money?
  • What would be the most secure or stable?

Instead, he asked himself what his ideal life, career, or job would look like, and actively moved toward that vision.

Of course, if you never ask yourself these questions, you won’t know what your ideal life even is. And if you don’t know what you want, how will you ever move toward it—or realize it’s possible in the first place?

How to Get Free Interns For Your Startup?

So sophomore year of college, I was halfway through this company that I was building, and at some point, we decided that we wanted to hire some college students.

We had too much work to do for ourselves. We were making some money, but we didn't really have enough money to hire a whole team of people, so we were brainstorming: how could we hire a bunch of students to do programming for us and do sales calls?

Summer was coming up and we had a number of friends who were doing internships—some of these unpaid internships where they got college credit.

We thought, "Well that's awesome! What if we could give college credit for working for us? Then we could get all these people to work for us for free and wouldn't have to pay them any money."

We thought it was a great idea, and we sort of scouted around online. We went to various college websites and tried to figure out how we could register for our internship with the school. We found this semi-official process where you register an internship, create it, and get approved by someone. It turned out not to be as hard as we thought. So we had an official internship that you got some general engineering elective credit for, and then we advertised it on campus and had a whole bunch of students apply.

Iremember going to the career services center—I show up in my suit and the woman at the desk says, "Oh sorry, your interviewer isn't here yet," and I'm like, "Oh actually, I'm here to interview students myself." Then they let me into the room, and the students showed up soon after that. We did interviews back to back to back and ended up hiring five students that summer.

We took a friend's apartment that was bigger than ours—he was gone for the summer—so we turned it into an office. We sort of had a real company then. It wasn't just a few of us. It was awesome.

This was really an important lesson for me: Sometimes there's another option that other people haven't presented to you, and if you think about things differently, you can find this other option.

—Keith Schacht, Discovering Your Passion, Creating a Career

Most people think, "We can't hire interns because we don’t have the money," and then they stop there. Their company doesn’t grow. But if you can find the hidden door, like creating an official internship that provides college credit instead of cash, you can keep moving forward.

Inspired by Keith’s story, I tried this for some of my own projects. Several departments actually posted our job listings officially. Of course, some departments asked for bureaucratic nonsense, like requiring you to have an LLC to seem "legit." Seriously? Anyone can set up an LLC for just over $100. But bureaucrats love playing their little games of what's official and what isn't.

Always look for that hidden option because it’s always there.

What I Took Away

There are so many lessons, so let’s go one-by-one:

  • It really doesn’t matter what you major in or your GPA. Instead, optimize for finding and doing what you love.
  • The riskiest thing in the world is not knowing what you want to do. Your main job in college (and life) is figuring out what you love and going all-in on doing that thing.
  • Try to do as many interesting things as possible. Projects, clubs, classes, startups, etc.
  • Drop the word “should” from your vocabulary. Stop asking yourself, "What should I do?" and instead ask yourself, "What do I want?"
  • Think of classes as a menu. Don’t just follow the set meal your major hands you. Pick and choose whatever interests you.
  • You always have the option to drop out. You’re never trapped. Always see and evaluate all options. Stay in school only if it genuinely makes sense to you.
  • Internal resistance is real. Even when you find what you love, you might hesitate or doubt yourself. That’s okay. Be patient, notice it, and learn to move through it.

Keith was one of the first Future SelvesI met in college: someone who had already walked the path I was just starting. He was close to where I wanted to be, just about twenty years ahead, and he genuinely wanted me to succeed by learning from his mistakes and experiences.

Right after my very first conversation with Keith, this is what I wrote down in my notes:

The biggest takeaway is that I should start messing around with [redacted] and [redacted]. Forget about ‘shoulds’ and just do what you actually want. Enjoy this time in college, and have fun!!!!!

And that's exactly what I want to tell you, too.

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.