Instagramable Balloons: How to get YC Partners to come to You

The story of a friendly airport ambush that led to us meeting two Partners from Y Combinator after many rejections

Yuri, James, and Kat happily meeting for the first time at Pearson Airport. We were total strangers, and they were joyful and surprised!

It was around 9:45am which is when I (Alex) typically arrive at work. It was quiet at iBoost and James and Jake were working hard. All of a sudden, James had this idea, “Should I go to Pearson and meet Yuri and Kat [partners at Y Combinator] when they arrive!?!?”

Let’s rewind one second. Where did this idea originate from?

Our company, OpenSports, is at the cusp of a breakthrough in the recreational sports market. We have been growing pretty steadily since we introduced our payment collection feature for game organizers/sports groups, and based on feedback from our loyal users and growth in different pockets in North America, finally feel ready to scale pretty quickly. The only thing holding us back, as for many companies in our position, is funding. Being in the position we are in, we are ready for the resources and network from an accelerator like Y Combinator. In fact, read here about the Erlich Bachman inspired “Watch me YC” hack we pulled to try to get YC’s attention for the Jan-March batch that we applied for! So, when we heard that Kat and Yuri, who travel around the world recruiting top companies to YC, were coming to Toronto on the weekend, we knew this was an opportunity to make a splash. We applied to see them at their office hours in Toronto to no avail. Another YC related rejection😩! So here’s where this story gets interesting…

Team Buy-In

Jake and I looked at each other unsure of what to say to James’ idea, but after a brief pause we both gave a resounding “Yes!” — why not meet Kat Mañalac and Yuri Sagalov from Y Combinator, the biggest startup accelerator, and give them a great big welcome to Toronto. The idea kind of went under-the-table for about half an hour until Alicia came in. James was super excited about his idea and wanted to get her opinion. At first all Alicia did was laugh (I feel like she does this when her answer is going to be no), but after a little persuading she warmed up to the proposal. We began throwing around ideas, and this scheme that everyone initially laughed off, started to become real. We decided that if we were going to do this, we were going to go all in.

James’ initial directions:

  • Everyone familiarize yourselves with the background of Kat and Yuri;
  • Let’s create and print out a few quintessential “Welcome to Toronto” signs to bring to the airport;
  • Let’s find a store that has “Instagrammy” helium balloon letters;
  • Pack up some Clif bars, and
  • Head out at 1pm.
Alicia still at iBoost, showing off one of our fresh-off-the-press welcome signs!

Of course, in typical OpenSports team style, we ended up being half an hour behind schedule, before we finally embarked on the adventure. After a long, directionally challenged escapade through Toronto’s underground PATH (to protect our precious “Y” “C” helium balloons from the cold), and a hop onto the UP train from Union Station to Pearson, we reached the airport just in time for our 2:30pm target.

James and I picking up the YC balloons and quite obviously very hyper!

Airport Set Up

In Terminal 1, right in front of the massive glass Arrivals double doors, we began setting up, with our inventory of posters, balloons, and Clif bars, and of course our collective energy and enthusiasm! Sure enough, the massive digital board displayed that the Toronto bound flight from San Francisco landed on time so we knew that the passengers (Yuri and Kat hopefully included) were on their way!! People seemed to be mildly entertained by our presence, asking us what the “YC” helium balloons were for. Waves of people kept coming through the arrival doors, from places like Bahamas and Brazil and of course, San Fran. Ten minutes turned into twenty and then thirty, and there was still no sign of them. Excitement turned to nerves and antsy-ness. Where are they?

Sitting, waiting, wishing!

Disappointed but Determined

We were disappointed not to get a chance to welcome our YC friends to Toronto, but still determined. We headed upstairs to regroup at the airport Booster Juice and think of a new plan. Since we had captured quite a bit of media by this point, I create a GIF of our mini adventure and tweeted it to Yuri and Kat so that they knew we were there waiting for them!

Our temporary “office space” at Booster Juice, home of creative flow🤓🍸

Jake, Alicia, and I had to leave the airport at 5pm, but James heroically stayed until the next inbound flight at 8:30pm.

Exhaustion and Euphoria

As the day went on and more flights came in, the amount of people that James saw started to enter the high hundreds. “Is that them?”, “That looks like it could be them🤔…”. James was getting exhausted, and eventually, he put his head down to get some real work done, until he suddenly looked up and saw two figures heading towards him…

(I wasn’t there but I imagine this moment like some romantic movie scene where they see the person they’ve been waiting for and their eyes get huge and their stomach drops)

…Yup, Yuri and Kat saw the balloons and signs and made a beeline straight to James! They saw our tweet as soon as their plane landed (thank you technology 🙏) which got their attention. Their first question was “Where’s the rest of your team!?” followed by expressing sentiments of being genuinely appreciative and happy that we did all of this for them. Yuri and Kat proposed that they could stop by the Ryerson based startup incubator where we work, the next day😮. This was not something we expected, even in our wildest dreams, but it was something we had been wishing for. All of our frantic, hard work had paid off!!

The Big Meeting

The meeting was set for 1:30pm on the following day, Friday. Jake and I went downstairs with one of our signs in order to welcome Yuri and Kat at the elevators. We took them upstairs to our office, introduced them to the rest of our OpenSports family, and the meeting began. Twenty minutes later, James and the crew emerged from the meeting room with big smiles, said their goodbyes to Yuri and Kat, and our team had a good debrief. To sum up, as James said, “This was one little step in the process, but definitely a cool day.” :)

Founders’ celebration in style! There was a lot to be thankful for this week.

This all just goes to show you that if you are genuine, persistent, and want to do something to stand out, a little extra effort never hurts anyone. Also, if James has an idea, don’t ask questions, just run with it — and don’t stop running until you get to the airport!!

If you want to know how the meeting went, just ask! E-mail and ask us about some of the brilliant advice Kat and Yuri gave our team, that we are now working hard towards executing. We feel so much more prepared to devour this recreational sports market and have huge, far reaching, long lasting impact!!!

P.S. Did You know That Dairy Cows’ Fitness Matters?

Kat at another presentation in Toronto. Take home point here: if you’re going to position your company as “The X for Y”, make sure people know what the Y is! She really liked this analogy.

Thank you so much for reading about our second YC adventure! We’ll be writing again soon. Alex, Jake, Alicia, and your family at OpenSports ❤