One weekend, my co-founder, Collin, announced “I met this guy who went through Y Combinator… the deadline is in 2 days, we should apply.”
We both moved to San Francisco the previous year, accepting offers as engineers in tech with dreams of one day starting our own company. A few months after moving, we started to tinker with different startup ideas on nights and weekends after our full-time jobs. We hoped that one day an idea would take off and we’d be able to quit our jobs and raise money. The “happy ending” to our startup saga (but in retrospect really just the beginning).
At the time, we were working on a feedback tool for meetings through a Slack Bot. We had nothing built. No paying customers. But we did have 60+ teams sign up through a landing page we hacked together.
So hey, what’s the harm…let’s apply to Y Combinator.
We spent the entire next day writing and re-writing our application. “That sentence has too much fluff.” “What’s our unique insight here?” “How do we market size this... how big is a big market?”
Eventually, we wrapped up our application (check out our Y Combinator application example). It wasn’t perfect, but good enough given our time constraint. We hit submit and went to bed. Reportedly, less than 10% of applicants receive an invitation to interview, so we knew the Y Combinator acceptance rate was low. And realistically, given where we were with the company, it felt like getting an interview was probably not going to happen.
A few weeks later, we user-tested our feedback tool for meetings. We put a mock Slack bot in front of real users and found that it would be incredibly difficult to incentivize people to consistently give feedback post-meetings. The idea that we applied with no longer seemed feasible.
We were back to the drawing board.
We decided to go on a multi-hour walk around San Francisco to clear our minds and discuss what issues were becoming more painful due to the rise of remote work (this was pre-covid). Based on our experiences at our current companies and conversations with remote workers, we thought that operations would continue to become more and more difficult.
We saw first-hand how hiring in multiple states, shipping physical goods, and figuring out where a business was based became increasingly complicated for remote companies. Specifically, something interested us about operations at the intersection of the physical and digital world (the beginnings of Stable perhaps, but not quite, you can read about how Stable got started here).
We decided to pivot.
We knew building culture was important to remote companies –– and had to be done differently without the intangible interactions at the physical office. An important piece of this is physical touchpoints –– which can be achieved through thoughtful gifts that show team members their company cares.
We validated these ideas through a few user interviews to conceptualize our next big idea: companies use Mistro to automate the assembly and delivery of care packages to remote workers every month.
However, we completely forgot that this was around the same time we would hear back from Y Combinator about our interview.
Later that same week, I was already asleep when I heard a knock at the door (we were roommates at the time). I shrugged it off and tried to go back to sleep.
And then I heard, “Sarah, we got the YC interview.”
I flung myself out of bed and immediately felt myself shaking from excitement and nervousness. I was in shock. They’re willing to take a shot on us. Someone believes in what we’re building.
Our interview was scheduled in two weeks. And the pressure was on. If we got in, we would get to quit our jobs and be full-time founders. We just had to play our cards right.
We quickly realized we had to make a decision. Do we pitch our old feedback on meetings idea that we applied with, or do we do a 180 and pitch our new pivot?
Because we knew the feedback on our meetings idea wouldn’t work and we wanted to exhibit genuine excitement during the interview, we decided to pitch our new idea although it was definitely riskier.
The next two weeks were a blur. We woke up for user interview calls at 7:30am. Started our normal work day at 9am. Coded for our full-time jobs all day. And then got home and scheduled more user interviews, brainstormed, and consolidated insights. Went to bed past midnight. And started the day all over again.
We found that companies with great remote cultures were sending physical gifts + care packages, and often spending hours researching vendors or assembling these boxes by hand. This insight was based on dozens of user interviews and 2 signed letters of intent. We heard stories about how a founder spent a whole day figuring out how to send flowers to a team member in Spain or how a remote employee felt cared for by physical gifts to celebrate a baby or birthday. We felt as ready as we could be.
We hopped in an Uber down to the Y Combinator office in Mountain View –– quizzing each other incessantly about the different questions they could ask and how we would answer them. We were still memorizing our answer to the first question: “What are you building?” We were running through how to handle explaining the pivot.
When we pulled up to the office, we quickly grabbed our nametags and paced in the orange-walled atrium. Some founders were practicing their pitches and other founders were preparing their demos with large hardware contraptions.
Eventually, it was time for the YC interview. We walked into a room with four interviewers. We quickly shook hands and sat down. Why would I use these? How does this build culture? Why did you pick this idea? The YC interview questions were the fastest 10 minutes ever.
It was a rapid succession of questions that pinpointed every weakness we knew we had but hoped they would be able to overlook. By the end, we felt defeated.
That evening we got an email. Rejected.
Although we felt disappointed, we let the rejection push us to keep going. We continued to talk to customers and build, inspired by the prospect of achieving our dreams.
And certainly, in 6 months, we were already full-time on our startup and had raised a pre-seed round. The Y Combinator interview questions the second time around felt a lot easier as the stakes were much lower. We knew we’d build the company regardless of the verdict. And we got in (but more on that in another blog post).
From the two times we applied, we did learn quite a bit about getting into Y Combinator. Here are our top 3 pieces of advice:
The YC admissions team sees thousands of applications and the longer it takes them to understand what you’re building, the less likely you’ll get an interview. Your goal is to make it as clear as possible for them to quickly grasp your product, value propositions, and winning qualities. Use bullets and lists when possible. Cut out all fluff and extraneous words. Keep it concise.
YC likes contrarian opinions with strong conviction. It doesn’t have to be controversial, but it’s important to have a unique insight that drives your “why” and “vision”. What will the world look like in 5 years? How can you build for it now?
In our original application pitching the feedback tool for meetings, we double-clicked on how the future of work is changing due to remote work, and how it affected the way team members meet and collaborate. We made this assertion that connected the current status quo of today to where the world is going in the future.
It takes years to build a big company, and while your beachhead needs to solve the problems of now, your vision needs to solve the problems of tomorrow.
It’s important to prove your ability to execute quickly. The Y Combinator batch is less than 3 months long and the amount of progress you’re expected to make in a short period of time means you need to show that you can move fast or change course.
What worked for us, is that we indicated progress in the constraints of time and were very data-driven. In our application, we said that in the last few months we had conducted 25+ user interviews, tested 3 landing pages (with the respective conversion rates), and got 60+ sign ups on the winning idea. Show as much traction as possible, but also timebox that traction to show how quickly it was achieved.
For anyone applying to Y Combinator, I hope our experience was helpful. Stay tuned for “Part II” of when I'll talk more about getting into YC (Winter '20 batch). You can also always reach out to me personally at sarah@useStable.com if you have any questions about the Y Combinator interview experience or want feedback on your YC application. Please note that these events occurred pre-covid and the interviews and batch are now remote.
Additionally, I talk a lot in this post about how going through Y Combinator was a “dream”. I certainly felt that way at the time but there are many paths to building a great business. While I loved our Y Combinator experience, it truly is just the beginning, and the dreams keep getting bigger. :)