Quitting College For a Startup

How do you know when the time is right to drop everything and go all-in on a startup?

Last week, I had an email exchange that came through my website from a college student who sort of lucked into a startup founded by one of his friends. He had jumped in at the beginning, which was 18 months ago, and it had enough traction to keep him motivated and busy. Let’s call him Donte.

Donte is now at a crossroads. The time has come in his college career to consider a summer or semester-long internship. So he has a couple of options:

  1. Leave the startup to take an internship.
  2. Forego an internship and hope the startup looks just as attractive to future employers.
  3. Drop out completely and see the startup through to its ultimate success or failure.

Let’s talk about the first two options first, but please don’t drop out of school before I get to the third option, because that’s the real issue.

An Internship Is About Skills

Whether or not to take an internship over working at a startup is a personal and professional choice, but it really comes down to what kind of experience you’re going to get and how that experience can be documented.

At my last startup, Automated Insights, we made internships a priority and also a funnel for new talent. We took on three to five interns every fall and every spring, and then another six to eight every summer. This was when our total head count was at about 50 and eventually up to 75, so about 10% of our headcount was paid interns.

This is a pretty common strategy for startups these days. My current startup does the same but with less people because we have a smaller headcount.

Now, we believed an internship at our startup was pretty awesome, but we also knew that nobody was going to confuse Automated Insights with Google or Goldman, so we made sure that our interns did actual client work. The tech interns wrote production code, the data science and machine learning interns worked with client data, the marketing interns developed client case studies. No one got groceries or drove people to the airport.

Well, we were a startup, everyone got groceries and drove people to the airport. But we didn’t single out the interns for these tasks.

The point is that when our interns left, they not only had real, quantifiable work to put on a resume, they had customer names to attach to that work: Yahoo, Allstate, Associated Press, and so on. What’s more is they had new skills, which are infinitely more valuable than bullet points on a resume.

That leads to my second point.

Bring New Skills Back to the Startup

This is what Donte might end up doing if he can swing it. The plan is to go back to his friend and say something like, “Hey look, I know I can’t be great at two jobs, but if I take this internship, let’s make a schedule and do a call once a week so I can stay on top of the business. And when I come back, I’ll have new skills and maybe even new connections for us.”

If he can negotiate a deal like that, he might be able to do both the startup and the internship, just like he’s currently doing both the startup and school, which he should, for as long as he can.

Now, let’s look at that same scenario from another angle — How does a startup look as an internship on a resume? Well, I can’t speak for every company, but if you want to eventually go to work for a startup or even a company with a startup-like mindset, those companies are primarily concerned not with who you are or where you’ve been, but what you can do.

Earlier I said that at Automated Insights, our intern stream was a funnel for new talent, and we hired quite a few of them full-time. However, we didn’t let them take a second internship with us and we didn’t let them drop out. Well, we weren’t their parents, we just wouldn’t hire them if they hadn’t graduated. That said, once they did graduate, if they still wanted a job with us, nine times out of ten we hired them.

Now, the flip side of this is that there are still quite a few industries and companies out there that do care where you’ve been, and maybe who you are. Finance is one of them. If you want to work at Goldman (or somewhere Goldman-like), you need to intern at Goldman (or somewhere Goldman-like). You probably already know whether this is true for you.

But Whatever You Do, Don’t Quit

When we first started building Automated Insights, the founder and I both had little kids, all of them under six years old, and this was back in 2010. At the time, the country was at peak college-crisis, where tuition was skyrocketing while job prospects were next to zero.

We talked all the time about whether we, who were lucky enough to have options, would pay for most or all of their college or just front them a lump sum to help them start their first company.

This is a first-world problem, for sure, but not an elitist one. I knew what I had to save for three kids to go to a good college and I knew I wasn’t going to make it. The college dream seemed like it was slipping away for those who weren’t super-privileged or willing to take on massive amounts of debt. And even if I could afford it, it felt like being asked to throw hundreds of thousands of dollars into a paper shredder.

For someone who paid his own way and graduated with a grand total of about $10,000 in student loans, the math was all backwards for me.

Nearly a decade later, not much has changed, and the news is not great. Tuition has not leveled off, I haven’t saved near as much as I’d liked, but the importance of college hasn’t waned much outside of software development.

And the social structure of it is still extremely important. Even though I never made connections in college that would benefit me years later, I got enough social skill to deal with and manage all kinds of people, which will never not be a critical skill.

Donte is in the same boat as my kids will be. Thanks to smart, hardworking parents who had a lot of foresight, he will graduate without a ton of debt. And, as I also mentioned at the beginning of the post, startup isn’t Donte’s calling. He fell into the opportunity and he enjoys it, but it ends there.

So his equation is:

A = You can afford college or at least get through it without sinking into unrecoverable debt.

B = You’re not literally 100% born to be an entrepreneur where doing anything else would be a crushing life blow.

A + B = Go to college, graduate, and don’t waste the opportunity.

You can do both the startup and the education. It will suck. It will mean less of that important social life and even less sleep. But honestly, while college and the few years after are the best time to be an entrepreneur because you don’t have a lot to lose, there is an opportunity cost when you give up the education. Yes, you can always go back, but the stats show that few do.

Furthermore, unless you’re already running a successful startup, you don’t have to be an entrepreneur tomorrow. The company you start five, even 10 years from now, you’re going to be that much more well-equipped and experienced, and that much more likely to succeed.

So do both, but if you have to choose, choose college. Then when you graduate, you can do whatever you want.