How we hacked the Y Combinator application process

Disclaimer: Do not read this post in hopes of hacking your way into YC. It won’t work. Besides, getting in Y Combinator is easy: just be wicked smart, create a beautiful product, get millions of users, and build a revenue stream that grows 20% each month.

This is not that story; this is how we got into Y Combinator.

Drawing by Eric J Eckert

Building the Company: Pre-YC

It was late 2009 and I was working a FT gig for the State of Texas running the A&M system’s website. As with most real jobs, it was boring and I was encouraged not to work too hard or to improve anything… it was Operation Status Quo, the game where the numbers are real and your job is actually in jeopardy if you try to change anything. Basically, it’s the anti-me job, and after three months I started to look for the next thing.

A year prior I had worked in the newspaper industry, and had left when the financial situation started getting crazy.

It was right when my job started getting unbearable that one of my newspapers connections reached out to ask if I could build them an app to put print ads online. It seemed trivial, but it was something to do, so I partnered with a friend from high school, and on nights and weekends we built that thing.

“Working your day job while trying to get more customers? Use time zones to your advantage.”

//

And it started making money.

At first, it was kind of fun.  We were careful not to do anything during our day jobs (or to use our employer’s computers) but we needed to get more newspapers on board so we did whatever was necessary. I would take advantage of time zone differences by calling east-coast newspapers before 8am CT and west-coast newspapers after 5pm CT.

It was a bit simple, and didn’t work every time, but after three months we had several newspapers cranking and it was enough to let my now co-founder quit his job in the real world.

Now, as fun as this was, it started getting hard to keep my startup and my job separated… and not just hard but stressful. We were just a few deals away from me being able to quit my job, but we weren’t there yet, and my wife with our newly born second child very reasonably wanted me around more, so I started searching for a different solution.

How we Built our Company Asking Hacker News

For some respite, I started reading PGs essays and other startup-related posts on hacker news… we even asked for help from the community and what they thought we should do.

My co-founder had long been a HN user, and had applied to Y Combinator in the past… now that we had the makings of a real company, he convinced me that we should apply.

I wasn’t convinced that it would work. Our company was no dropbox, and we both seemed pretty old for the YC crowd, but we sat down, talked it out, and figured out that we had a chance if we could hack the process.

How You Should Approach the Application

The first thing we did right was the application.

If you’re writing your Y Comb application and it takes you less than a month of work, you’re not trying hard enough. Read that again. Your YC app should be the hardest document you’ve ever written.

And after you’ve written it, write it again.

Make a contest with yourself to see how much you can communicate in the smallest number of words possible—if you can’t answer each question in one tweet, then you’re including too much: simplify, simplify, simplify.

And after it’s short and perfect and beautiful, take it to Starbucks.

“Y Combinator is the most exclusive program that you can openly apply to… so do your homework!”

//

Offer people in line a cup of their favorite brew in exchange for explaining your application back to you—I actually did this several times and every time it improved our application.

Even though Y Combinator is more selective than it has ever been, it’s pretty mind blowing how little thought people put into their applications.

Think about it: Y Combinator is the most exclusive thing in the world that you can openly apply to. Damn! Have you really put enough work into your application?

I’m just saying, at least spell-check the thing once or twice :)

How we Built our Y Comb Application

When we applied, we didn’t know anything about startups or investors. We especially didn’t know the importance of traction, social proof, product, and team (things every investor, including Y Combinator, looks for). But we did have a natural understanding of systems and how to hack them… and that’s what we did.

“Want to get into YC? Understand traction, social proof, product & team… or learn how to fake it”

//

So, we got historical.

We figured that current YC companies had a pretty good insight in how to get into YC (note: this is actually less true than you might think, but keep reading my post anyway).

We found as many winning applications that the internets had to offer. While there weren’t than many out there, there was plenty to extract: Drew from Dropbox was a brilliant individual, Dave from Weebly had a shot at taking on a huge market, and other guys, like Thomas and James from NowBox actually implemented the H.264 encoder shipped with QuickTime… they had great experience and had proven that they knew how to apply it.

We were not any of those things, but that’s okay, because those things are surprisingly easy to mirror… once we knew what the YC team was looking for, we knew how to present our company.

Things we were already doing right:

  1. We had the advantage of applying under the first RFS (request for startup), which was to fix journalism. Our idea was to fix journalism by monetizing it, and our software was already doing just that.
  2. We were already making real newspapers real revenue—hard to argue with that. I’m convinced that if we wouldn’t have had this traction, none of our investors, primarily YC would have chosen us.
  3. We were committed to doing this full time  We had bootstrapped to the point where my co-founder was already working 100% with the company, and I was closely behind. We weren’t in school, we had no big careers to fall back on, and we were not particularly amazing on our own—our only chance at success was this company and that made us ruthlessly committed.
  4. I had secret industry knowledge. After working with newspapers for 9 years, I knew what made them tick, what they would do, and what they wouldn’t.

Things that were against us:

  1. Our market is notoriously bad at technology and the success of our product required them to adopt ours.
  2. Our product was ugly, and barely worked. We were pushing so many features so quickly that the code and design was a mess. We didn’t really know what we were building and what we had built was mostly terrible (this is of course no longer the case, since we discovered test coverage, our product has improved immensely).
  3. We had no educational or employment pedigree. Both my co-founder and I came from small colleges in the Midwest, we were both pretty old (27) and had not made any major waves at any company you’ve heard of. When the guys who implemented Apple’s video compression want to start a video company, that’s pretty impressive; when two schmucks from the Midwest want to save newspapers, it’s a little harder to believe.

Read Our Winning Application

Yc Application

How We Hacked Our Video to Help Get In

After we submitted our application, we spent about 8 hours planning and shooting our video, then another 4 hours editing it. At the time, they said the video had to be under one minute—which is nearly impossible, but we cut it down again and again until it was as short as it could be.

(BTW, no one’s video is under a minute. I’ve seen hundreds of YC application videos since then, and they are never that short… like a lot of things in life, Y Combinator’s time limit is arbitrary, but it does help to make it as short as possible. )

So we spent a lot of time making the video… which might be surprising because it looks terrible. Watch it, and you’ll see that it’s not very good. But that’s by design.

I worked my way through college by doing event and charitable-foundation videos, those all had to be high-quality productions, but I purposely made ours low quality to make it appear as if we were not trying too hard. Hint: we were trying too hard, and so should you.

Once we got the Interview, we knew we were in

Whether it was spending the time writing the application, meticulously planning the video, or just blind luck, we got an interview. And once you have the interview, you’re most of the way there.

Thinking about it now, once we got the email saying we had gotten an interview, I knew we were in.

I’m not trying to say you’re a major loser if you make it through the application process and fail in the interview… but you’re kind of a major loser if you make it through the application and fail in the interview :)

Of course I’m just kidding. But my point is, if your company and team is solid, than you will get in.

If you don’t get in, then the Y Combinator staff probably sensed something you didn’t… so what was it? It’s really important to figure this out because whatever it is will probably kill your company. But that’s okay too because you can always start again–one good idea might be to hook up with an existing YC portfolio company and learn what you were missing. Once you go through that process, you will be stronger and smarter the next time.

In many ways the application is a crap shoot and I’m sure it has missed winners… there are just too many variables: who reads your app? How long did they look at it? Were they about to run out the door? Thinking more about lunch? Did they get enough sleep the night before? What if they can’t understand your product in under a minute? (That one’s your fault BTW)

“The YC interview is not meant to identify who should get into Y Combinator, but should not”

//

What if they just don’t like your company name because it reminds them of a kid that beat them up in high school?

I know YC has mitigated a lot of this by utilizing founders to vet the applications and using real data analysis to identify good applications (it’s real, I’ve seen the high-level data), but stuff still has to slip through the cracks.

And if that’s true, then the hardest part is the application, after that you’re pretty much in (unless as I previously mentioned, you’re a joker :) ).

The interview itself is really not to identify who should get into Y Combinator, it’s to identify who should not. That is, a face-to-face meeting is the best way to identify potential founder or idealistic problems.

When they meet with you, they’re really trying to answer a series of questions about you:

  • Is he smart?
  • Is she going to give up?
  • Why are they doing this? Because it sounds like a good idea or because they actually want to build something people want?
  • Is the idea good? If not, are they dead set on the idea or can they look past their pride and iterate and change if necessary? (Hint: you will have to change your idea)
  • Do I like this person?
  • Can I relate to them?
  • Is this guy totally full of shit or can he actually deliver?

So don’t fret, if you make it to the interview, you should be fine.

How We Hacked Our Interview

We got to pick our interview time and choose a slot early on the second day—the logic was to choose an early slot so we’d get to present before their decision fatigue set in, but we wanted to go on the second day so that  they would have already sat through groups who were worse than us.

“YC founders are smart, so use your YC-subsidized trip to make your company better by meeting them”

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Coming from out of town, we arrived a few days early to take some meetings with area Y Combinator guys. They were all very gracious with taking time out of their successful startups to give us advice, and a lot those meetings helped us shape how to talk about ourselves during our interview.

For instance, Dave from Weebly suggested that we were really going after the SMB market, but hacking the sales process by using newspapers as our sales force  The important takeaway here is that YC founders are smart, if you’re not from the bay area, than use your YC-subsidized trip to make your company better. If you don’t get in, you’ll at least have learned a lot.

There were also a bunch of current YC founders in the waiting area who we talked to about what we were doing and took advice from. PG asks current founders to come in during the interview times to interact with potential folks… it works as a nice way for the interviewees to work through their nervousness before it’s too late.

The Actual Interview

The one thing everyone said to us was that the interview would be the most intense 10 minutes of our lives. For us, that wasn’t true: when we finished, I thought that it was so easy that it must have gone badly.

“Maybe they didn’t understand us? Or maybe we weren’t cool enough to get in? I told you not to wear that hat!”

It turns out that Occam was right on this one: it was easy because we nailed it; there were not hard questions because we knew our market; and we got in because we were better than most.

5 Things to do Right in Your Interview:

#1: You only have 10 minutes; go with it.

We walked in and without any introduction Paul Grahm said, “You’re building the Yellow Pages for Newspapers.” We weren’t actually doing that: that strategy had been tried in the newspaper industry for years and we knew that wouldn’t work… but what we said was, “Yup, you got it.”

“Minutia isnt important during your 10-mins with Paul Graham; get to a basic understanding & you’ll win”

//

#2: Y Combinator probably doesn’t understand your industry

This wasn’t apparent until later when we were talking to PG about an industry term… he said, “You know, this is amazing, you guys really understand everything about a market I know nothing about.”

This took me by surprise at first… previously I was under the impression that PG’s knowledge base came from super-human abilities, but it turns out that he’s just a really smart guy who understands people, investors, and building companies (in that order).That means if you know your market really well, there’s a better than good chance that he has bad advice—sticking with the first point, make sure YC can understand of your industry, but don’t get bogged down in details.

“Paul Graham is a mere mortal: brilliant when it comes to advice; probably wrong relating to your specific industry knowledge.”

//

#3: Focus the conversation and stay away from rabbit holes

All of the YC partners are brilliant, which means that they will think of very different, and sometimes very interesting, angles to what your building.

Sometimes this means that you should listen to them and maybe change your product, but often it means that you need to quickly acknowledge their point and move on—after all, you’ve spent months or years on this idea, they’ve spent minutes. Prove this to them by focusing the conversation.(If they get stuck on a particular point, don’t brush it off: instead, quickly create a compromise or you’ll lose them.)

“You’re the founder, during your YC interview you need to prove that you can lead the discussion”

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#4: People with language barriers or accents probably have a disadvantage

Both me and my co-founder are from the Midwest, which means we basically don’t have an accent. This allowed us to quickly and clearly communicate during a very rapid-paced interview. One thought I had later was that people, even really brilliant founders, with thick accents or who don’t have English perfected, would be at a serious disadvantage.

It’s basic math: if it takes you twice as long to communicate something, you only get to say half the things.

“Have the founder on your team who speaks the clearest (not the most convincing), do the talking”

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#5: Know the one thing you want to communicate and save it for last

Whoever interviews you will be considering hundreds of potential companies for the current round.

“You only have 10 minutes in a YC interview, know the one thing you’re going to communicate & save it for last”

//

This means that they will barely remember you, so choose beforehand what they will remember.

Are you brilliant? Did you know everything about your industry? Is your company printing cash? Are you a design mastermind? Choose one thing, and only one thing, and drive it home.

For us it was that we were completely committed to the business. Since we were going after a non-traditional market we felt it was key to let them know that we were doing this with or without YC, and if they wanted to miss out, we didn’t care. The last thing I said to PG as we were shaking hands was, “Thanks for this Paul, we’re from the Midwest where everything moves a bit slow–even if we don’t get in, this trip has convinced us that we’re moving out to the valley to do this full time.”

What to do When the Interview is All Over

Moments after our interview.

After the interview we allowed ourselves just 30 minutes to obsess about what went right and what went wrong, and then we took a long drive down the 101 to clear our mind.

With the month of preparation, the constant practice, and the actual interview, there was nothing more we could do to make them pick us, so we let it out of our minds for the next 11 hours.

Of everything we had planned, I’m glad we did this.

Once we got back to San Francisco, our day of clarity made that 6:35pm call so much sweeter: “Hey Lloyd, this is Paul Graham. We’d like to invest in your company.”

After a few high fives, an awesome dinner, and drinks at a cigar bar, we went back to work growing our company.

By the time January 2010 came around, we had launched a new product at several newspapers, and were on our way to building something people want.

14 thoughts on “How we hacked the Y Combinator application process

  1. Great post, very honest and informative, wish you all the luck and success
    But you are 27 and call yourself old? what does that make me? I’m 35 next week
    In any case, I’m very happy to see people with families applying and being accepted to YC, I think that it needs a lot of courage (time with family, health insurance, financial stability) but I think people with experience in an industry have much more chance disrupting it. Hope to see more like this, and happy YC is in the right direction.

    1. Thanks!

      I’m 31 now and while I’m not old, I can definitely feel the effects of age setting in (I can’t go days without sleep anyone, for one example). Also, my humor is a bit sarcastic and self-deprecating, but the fact that I’m joking isn’t always obvious :)

      Honestly, I think the idea that YC is mostly a young crowd has nothing to do with YC decision makers. I can very confidently say that they would take anyone if they thought that they would make a good founder. I personally thought that we would be too old–there certainly are not a lot of YC alums who can leave their family for three months–but I think that was in my mind.

      1. I turned 35 in June, so I also felt the pangs of “If 27 is old…”

        My mid 30s have been really excellent – I have learned a ton and really settled into who I am and what I want to do. The aging process stinks in a whole lot of ways, but it beats the heck out of the alternative. :)

        Thanks for writing this – I enjoyed reading the approach you took to Y Combinator! Best of luck in the future.

      2. PG said that they DON’T take mostly young founders – it’s just more buzz that “billionaires under 20″ produce in the press that makes such effect.
        Thanks for the post.
        I’m going to press “Submit” button right now but still have shaking hands… :)

  2. at least spell-check the thing once or twice…

    “All of the YC partners are brilliant, which means that they will think of very different, and sometimes very interesting, angels to what your building.”

    1. Touché! I had that fixed right away but with caching it didn’t show up until now. Keep the hard-hitting criticism coming :)

  3. I think you need a refresher in what the word “hack” means. It does not mean “to work hard and to perfect something”.

    1. Man, this has really pissed a lot of people off… here’s my logic:

      One definition of a “hacker” is someone who accesses a computer system by circumventing its security system.

      Because we had a lot going against us–we’re in a non-sexy industry, we’re not geniuses, and other reasons I listed–we had to take a different route to get into YC: which I’ve explained in this post. You *might* say that we gained access to YC by circumventing the normal formula of genius developer + educational pedigree + great idea + tons of traction. But maybe not. As PG said, they were impressed with our knowledge of local newspapers. Maybe that was enough and all of our preparation was for naught :)

      But I still think we performed a bit of a hack.

  4. Lloyd and Jason, I’ve been loosely following your company over the years and to say I am impressed after reading this is an understatement. It’s amazing what you two and your team has accomplished. Best of luck.

  5. We are working on our tech startup the AirBNB way (bootstrapping with a product called WordBiLLY.com) and this is very useful since we aspire to part of Y-combinator family as well. This was very informative. Just hoping the recent StartUp school videos get uploaded soon. Brian Chesky’s talk in 2011 was very useful, especially their marketing & PR hack.

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