Read about this company’s hilarious hacks to get into Y Combinator

This is a story about the crazy shit you do when you want to fulfill your dreams as a startup 🙏🏼🌠

If you’ve watched the TV show Silicon Valley, you know that the startup scene is incredibly competitive. Sometimes, it feels like a constant race to “beat your competitors” and find “product market fit” and there’s a general feeling that the only way you can win is by getting accepted into a top-accelerator in the Bay Area.

Y Combinator (YC) is the behemoth of accelerators in the real Silicon Valley. Twice a year, they invest in a large number of early stage startups. Being home to the likes of Dropbox and Instacart, YC has been dubbed “the world’s most powerful start-up incubator.” It’s sort of like winning the jackpot…If you get in, you’re SET 🚀. Everybody wants in! Last winter alone, 7,200 startups wanted in… and 100 got in.

I want to tell you the 6 minute story of what happens when a startup thinks they’ve got a real once in a life time chance…

Chapter 1: A sliver of hope

Tuesday October 10, 2017.

Our CEO James sent a really impressive application to YC. He has done a fair share of research on the process and let our team know that the YC partners who review applications give each company’s application about 15 seconds of their precious time 😲.

But… a week after submitting our application, on Tuesday afternoon, James randomly got a message from “Michael” of YC:

On your application, in the question asking if your coding is done externally, and who does your coding, you wrote “No”. Please clarify.

Holy… F*^k. Someone from YC RESPONDED !!!🙀🙀🙀!!!

Unable to contain ourselves💃🏼🕺🏻

James hastily google’d the name Michael. He is the CEO of YC. Through bouts of laughter and high fives all afternoon, we revelled in the fact that they know we exist… and they are interested enough to ensure they thoroughly understand our application! Keep in mind, these shrewd AF people pay attention to only the clearest and strongest applications (Note: The fortuitous mistake in our application occurred because of #NoSleep).

In our world, we had a huge shot! James went an bought bottles of champagne, and our team celebrated🥂.

This was the energy all of Tuesday afternoon after the initial email. I felt compelled to capture the genuine passion, excitement, fatigue, leadership and hope that James embodied!

Chapter 2: Becoming attention grabbing A-holes.

Following Tuesday’s excitement, the rest of the week entailed plenty of low key brainstorming of creative ideas that may get the attention of relevant people at YC, and/or the media.

  • Should we plan a pickup soccer game in SF for all the companies at YC?
  • Should we get quotes from YC alumni for a blog post about how sports/physical activity motivated them to stay active and prevent burnout during their term there?
  • Maybe we can blockade the YC entrance with OpenSports users, Clif bars, and a ping pong table, and challenge everyone to a game against an OpenSports pro?
  • Or we can start a cross country van tour visiting OpenSports communities. Maybe cycle there?

…and dozens of more hilarious ideas!

Finally, on Thursday night, between chatter about OpenSports icons or something, there was an idea that stuck…

  • Let’s anonymously create a “startup roulette” website…

My response:

Followed by a quick midnight name brainstorm:

…and then… the magic 🎩:

The domain was purchased. This was happening.

Chapter 3: Getting the team up to speed

Friday at 2:30pm when we were all in, we called a team meeting and packed ourselves into a closed off whiteboard room. We had to plan this thing, design it, and build it in… an 18 hour sprint. Given the compressed time line, we had to work quick and flesh out only the best of ideas.

The overall vision was to create a webpage that would have a constant feed of the one minute application videos that founders sent to YC. The inspiration came because 99% of applicants don’t get in, and don’t receive any feedback about why, so we wanted to create a space where founders could receive feedback (and beer), and viewers could know whats going on in tech.

Ideas that made the cut:

  • “Send a beer to your favourite startup” button 🍺 (not real beer, silly! Although, that was the original idea)
  • Leave anonymous feedback in a comments text box (that get sent only to us, and we would subsequently send the feedback to the company)
  • A nav bar with a drop down list of video categories
  • An “About me” section (which would just be about the project, and not about OpenSports)

Chapter 4: The Design and Development Sprint

It took Orest less than an hour and a half to design the entire site — In our meeting, he already knew which “sexy” shade of red and what font he wanted to use. Kaylin, Ryan and I started watching hours of YC application videos (this was much more tedious and much less fun than one would think😪!) and categorizing them into categories like “E-commerce, Fintech, Sustainability, Basically Air b n b”, etc.

By 5:32pm on Friday, the site was up. Damn, we’re fast:

Chapter 5: The marketing strategy

The marketing strategy was simple and hilarious: Spam the press and all the big tech news sites about WatchMeYC, pretending to be Erlich Bachman from Silicon Valley.

We laughed our heads off as our designer and creative director Orest embodied Erlich. He needed to do his research via YouTube videos to make sure the banter was perfect👇

Watching videos of Erlich Bachman to fully get into character.

James found a list of hundreds of tech reporters and on Monday, we sent them all an e-mail from the account of Erlich (, about our new website. The e-mails we sent to journalists and tech news sites like TechCrunch were hilarious! They went something like this:

I know you look at me and see me as a guy who has it all figured out, and for the most part I do. When I sold Aviato, it gave me a home, cars, food; but there has always been a hole in my heart. I guess that hole is the “what if?” What If I don’t get into YC?
I guess we’ll never know because I always do.
But what about the 99% that don’t get in? Well that’s why I made
Why, you ask? Well, why not.
The Silicon Valley King.

Chapter 6: The fall from grace

Out of 220 emails sent on Monday October 23— Google blocking many of them — we got a response from one… ONE….REPORTER 🤢!

FML. Needing a break from it all!

Our posts on Reddit got taken down. Twitter did not allow us to have an Erlich Bachman account… nothing was going right 😩

But I still had hope! So much hope that I took a “pre-becoming-famous” video!

Chapter 7: Decision day — Did we get an interview?

Tuesday October 24th, One whole week after that initial message from “Michael”, was decision day with no indication of what time we would receive the much anticipated e-mail from YC. James predicted it would come between 9pm and 1am, given the 3 hour time difference between Toronto and San Francisco.

Our team was fairly certain we would get the interview. I could see it in James’ eyes and his behaviour that he felt so strongly about it.

The interview would mean we would fly to San Francisco the next week to meet the YC partners. Half of the teams who go for an interview actually get in to YC, so your chances are high when you’ve made it to the interview round. Then we would move to San Francisco from January to March, for three of the most intense months of our lives, a period when stress would eat us from the insides out, but we would learn and grow as a company a LOT.

I couldn’t hang around all night to wait for the decision, so I just waited to hear from our team, who were having some pre-celebration drinks. And then at 1:34am came the message from James:

…bla bla bla…

Chapter 8: Coming together to ease the pain like a real #fam:

On Wednesday morning, Orest and I went to a grocery store in our building to buy a cake, so that our team could celebrate “not getting into YC”!

We decorated our own cake:

Turning the lemons of tragic loss into some lovely profane lemonade 🍋

And shared a slice with everyone in our Toronto-based startup incubator 🍰.

Chapter 9: Live and Learn

After all of that, what happened? Nothing. But our team got to temporarily pull our minds away from the amazing project we work on 24/7, OpenSports, and completely let our creative minds go wild. The amount of laughs we shared through the constant exchange of fun ideas was invaluable!

More than that, we can apply learnings from this project to future tasks. Here’s an example: During this whole period, we were certain that some of our new OpenSports users from the States were YC people spying on us and testing us out. Based on how thoughtful I was whenever I reached out to the people I was suspicious about, I created the motto “treat every new sports organizer like they’re a YC CEO.” It helped me think of new systems to ensure high quality engagement and retention on the app🤓.

Chapter 10: The last shot

Oh, and here’s the product demo we made in 5 hours 🙏🏼, because we’ve got an amazing product. And an active, engaged community. And we build and iterate like crazy. And best of all, we ❤ and respect each other. I know our team is destined for greatness.

Will we apply again? F🐧🐦k ya. This hasn’t disarmed us, after all, as Mattan Griffel, a successful YC- accepted founder wrote in his blog about How to get into Y Combinator:

…Y Combinator shouldn’t be the end-all-be-all. It’s still only a step on the way to success or failure for your company. If not getting into Y Combinator means your startup is going to give up, or won’t succeed, that’s already a very bad sign. That being said, Y Combinator is a very cool and valuable experience that benefits just about every startup.

Chapter 11: Update: The Story Continues…

So…. we ambushed Kat and Yuri (Partners at YC) in January at Pearson Airport in Toronto and it led to something pretty epic! Read about that here :)

Thank you for reading :) We have many funny adventures and stories. If you want to hear more, e-mail me!

❤ Your sports fam, Alicia and the OpenSports team

P.S. Want to watch our one minute founders’ application video that was also posted on I think James applied some kind of algorithm so that our video plays once every 10 videos, so you should find it there easily 🙊. You’ve gotta be creative 😈😇.