My YC application advice (Oversubscribed Weekly #36)

August 29, 2019 by Max

Max here. It’s that time of year again: with the deadline for the next YC batch approaching, I’ve once again been barraged by friends, acquaintances, and even the occasional stranger asking for my advice on their application. So I thought I’d use this newsletter to share my YC application advice.

Since a good application clearly and concisely communicates the thinking behind your company, this advice should be useful to you even if you’re not applying to YC. In fact, filling out the YC application can be a helpful exercise even if you’re not planning to apply. Doing so often forces you to think through aspects of your company and pitch that you may not have realized were a bit fuzzy.

As a bonus, at the end of this post, I’ll share my former startup Castle’s successful application for YC W16. But before that: my top four pieces of YC application advice.

#1: Be concise

This is far and away the most common piece of feedback I have when founders ask me to review their applications. Most questions on the application do not require more than 1–3 sentences to answer. Adding more than that bores the reader, gives you more opportunities to put your foot in your mouth, and makes you come across as a poor communicator.

I can’t find a good link for it, but there’s some psychological research—I believe by Daniel Kahneman—that demonstrates that a single strong argument is often more compelling than that same strong argument plus an additional, weaker argument. If you have a compelling answer to a question, you’re actually hurting yourself by appending additional data that isn’t as persuasive.

#2: Explain your company in simple, clear language

This tweet encompasses this advice better than anything I could write:

There’s something about pitching their startup that makes some founders want to talk in the most bullshitty way possible. When YC asks, “What does your company make?,” don’t launch into some winding yarn about your mission. Just say what you make.

For example, Castle’s answer to this question was “Castle finds tenants, collects rent, and coordinates maintenance for residential rental properties. We automate this process with software and on-demand labor.”

#3: Seem like you’re having fun

If you Google “YC application advice,” you’ll find lots of blog posts telling you to be concise and to use simple language, but the admonition to have fun is, I believe, more unique to me. I think it’s just as important as the others, though.

Investors—and YC especially—want to see your genuine enthusiasm for your company and your cofounders. Founders who are having fun are more likely to be able to recruit successfully, resolve cofounder disputes, and stick with their company through the hard times.

I wouldn’t go so far as to add actual jokes to your application, but there still are plenty of opportunities to show that you’re having fun. One easy way is to use more casual language when appropriate. For example, when answering the question about our competitors, we used the phrase “We’re not scared of any of these guys.”

The section about how you met your cofounders is another ripe opportunity for fun. In our application, my cofounders and I described each other as “platonic soul mates.”

#4: Don’t be discouraged if you don’t get in

Most companies that apply to YC don’t get in: in 2015, the acceptance rate was 1.5%, and it’s presumably only gotten more competitive since then. If you’re reading this, your chances are probably better than 1.5%—I’m sure that stat includes a bunch of obviously terrible applications—but, as with all things startups, there’s a lot of luck, bias, and randomness involved.

Castle applied three times (showing new progress each round) before we got in. And we still failed, like even most YC startups do! Getting into YC—like closing any other investor, or signing a big customer, or any other milestone, really—isn’t a guarantee of success. So keep your chin up and your head down, and keep grinding on your company.

And now, as promised: Castle’s successful W16 application.

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