Monday, February 25, 2013

The hardest question on the YCombinator application

For the past two years, I've worked at becoming a better programmer, all with one goal: my own startup.  After lots of work, learning, and discussion, my friend and I have an idea and a half-done prototype.  It's finally time to do what I've been waiting for all this time: Go to YCombinator.

Well, we have to apply first.  Naively, I thought the application would be like anything else I've ever applied for.  I'd fill out my name, answer a few questions about myself and my idea.  I was incredibly mistaken.  Writing up answers took up four days of writing, editing, and thinking.  It forced us to finally look into how we'd split up equity, made us think through our entire pitch (four times), and had one really, really hard question.

No, it wasn't the money one (though I'm still not sure how to answer).  Nor was it "What is your company going to make?" (though that was the second hardest).  Surprisingly, the most difficult question for me was:
If we fund you, which of the founders will commit to working exclusively (no school, no other jobs) on this project for the next year?
Founding a startup is a big risk.   I could find myself penniless in two years with no property and fewer prospects.  I owe it to my parents to finish my degree, and to my fiancee to have a secure job after we get married.  The startup life can't promise either of those.

Every startup founder has an incredibly tempting out: the day job.  As Dilbert-esqe as they are, a day job is a siren call to the guy who has been subsiding on Ramen singing the promise of a salary and a solid night's sleep.  I know at any time, I could drop the whole pretentious startup thing, finish my degree, and get a nice comfy job somewhere where someone else will make all the decisions.

Answering yes means that I'm giving up on finishing my degree in a timely manner, if at all.  It means I'm accepting one of the most stressful jobs I could have.  I spent a lot of time staring at the screen, wondering if I could be daring enough to put down an emphatic YES.  I almost didn't do it.  I almost said "I'd like to work on a startup, but..."

You may not be an entrepreneur.  In fact, you don't even need a job to hit a decision like this.  Our culture (and parents) emphasize a conservative lifestyle, playing it safe at every turn.  Today, take a risk.  Do something different.  Don't let yourself worm out of it.  You'll be surprised at the results.

If you've read this far, you probably should join the discussion on Hacker News.


  1. LMAO ohhhh Randall, I was reading your post and started cracking up. I was applying as well, with a half done proto-type and a solo founder, though I know they don't usually do solo founders. But even so I was staring at the same question thinking about the same ish... lmao good post man. Good luck to you and your co-founder.

  2. My 2 cents - that shouldnt be a hard question at all (i dont mean that in an insulting way). It is to see if you are committed 100% (or 150% or 1000%).
    (1) Finish your degree. < shows you can finish what you start.
    (2) Explain to your financee your plans for the first few years after school. If it is in your heart to do a start up. < let her know exactly what she is getting into with you. (its not fair to you or her otherwise).
    (3) Find some bio-books/stories about guys who started tech companies while in U/College or right out of school - and how they literally had nothing to live on ($ wise) - but made it - that can be used as a motivation. [i'm sure they will say things like, i lived my job 16 hrs a day, and blocked everything else out of my life (which means, if married/engaged - explain - since sometimes marriages dont survive this]

    Good luck!! You have what it takes - young, smart, motivated ... keep us posted as you progress thru these steps and grow.

  3. I suggest you also apply to Bizdom Cleveland.
    Up to 25k, office space ((, access to many mentors.
    All you have to do is send your Y combinator app to: