When your side project gets an interview with Y Combinator

Kevin Hale from San Francisco, CA, United States, via Wikimedia Commons

“How will you get your users?” I asked my cofounder, Max. We stood in a parking lot in Palo Alto, under a basketball net emblazoned with an orange Y. I was imitating Paul Graham, the founder of Y Combinator. “Three strategies…” Max starts to answer.

We had already rehearsed the answer to this question 100 times. Our responses needed to be perfect, concise, and confident. We were about to interview at Y Combinator (YC), one of the top seed accelerator programs for early-stage startups. The ten-minute interview ahead of us was our only chance of getting in.

Every 6 months, YC invests $150k in exchange for 7% equity in 150 startups. The YC deal isn’t entirely about getting seed money, though. It comes with a lifetime of mentorship, introductions to investors, and connections to over 4,000 alum. Companies like Airbnb, Stripe, and Dropbox got their start in the program.

Once accepted, YC companies can immediately sell their products to other companies in the accelerator. It’s like joining a special club. And it felt that way, as we walked into the bright orange headquarters, into rooms lined with banquet tables and sketches from Paul Graham. There appeared to be a dress code—lots of puffy vests with button-down gingham shirts. Max and I joked that we should have stopped at Patagonia on the drive over from San Francisco.

Paul Graham’s “The Startup Curve”

The atmosphere inside the headquarters was tense, like we were all about to take a standardized test or have a medical procedure. There was CBD lemonade in the waiting area to help us calm down. The other founders were huddled together rehearsing their interview answers, and they seemed entirely unapproachable. Founders had flown in from India, France, Israel, and other places across the world for a ten-minute interview which could shape the course of their lives.

How did we get here?

In August, I co-founded Your Boss with my friend Max Hawkins. It’s a voice-chat app that connects self-employed people in phone calls where they pretend to be each other’s boss. It’s part accountability, part social network. We originally built it for ourselves, but decided to make it public. After we launched our app on Product Hunt and it attracted a few hundred people around the world, we realized Your Boss had the potential to be bigger than a side project.

My background is running many small bootstrapped businesses. I’ve never created a digital product with thousands of users, so I sought advice from investors and other startup founders. Everyone told us we should apply to YC—not just for the seed money, but for the mentorship and community since this would be our first tech startup.

Applying to YC is a journey

We didn’t apply to YC on a whim. We worked on our application on nights and weekends (as we worked other jobs) while carefully researching the program and talking to as many alums as we could. To find alums, we sent cold emails and Twitter DMs asking to meet or hop on a call. We also reached out to our own network for intros. People kept encouraging us to apply and offered advice. The YC community is strong.

The application itself is a series of deceptively simple questions like “What are you building?” “Who are your competitors?” and “How will you get revenue?” My cofounder and I had hypotheses, but taking the time to write our responses made us notice gaps in our logic or discover new directions for our company.

While writing our answers, we researched other productivity tools, tried existing voice-chat apps, read about the future of work, interviewed our users, learned new software, fixed bugs, redesigned our app, and queued up marketing strategies to increase our growth. Each question on the application is a useful thought exercise that helped us build a better product.

YC wants you to be a certain kind of company

Once we finished our application, we reached out to alums to give us feedback. The most common piece of feedback we received was, “You’re not thinking big enough. What is the billion-dollar version of your company?”

There are so many blind spots when you’re launching a new product. One big unknown is finding the revenue model that works. YC doesn’t want you to have any unknowns about your revenue model. They expect your revenue to be millions of dollars per month. With an experimental app that’s twelve weeks old, it was difficult to say that we’ll have 10% of the self-employed workforce (53.7 million) people each paying $10/month to be on our platform. It’s only a hypothesis.

You should be absolutely certain of your hypothesis on your application. YC partners are reading thousands of applications, so you have to shout out a clear and confident path to revenue. You have to imagine that you’ll obviously become the same size as Airbnb. Even if you want to experiment with three different revenue models to see what works, you should only choose one to discuss and be confident about it. On our application, we wrote how Your Boss will be the new, affordable WeWork for every self-employed person regardless of location. After a few weeks of refining our application questions, we got the interview.

The YC interview is a game

Immediately after our congratulatory email, we slowed down production on our app to prepare for the interview. Unlike other investor relationships, which are built over time, there’s only one shot to introduce yourself to the YC partners in person. During the ten-minute interview, the partners try to figure out the weakest points in your business plan and ask you questions about it. The trick is to answer their questions quickly and directly, while also guiding the conversation in the direction you want it to go. It’s a tough interview. Your fate with YC is based on a fleeting moment where you have to say all the right things and check their boxes. They decide if they want to accept you within five minutes after you leave the room.

For comic relief, I made a pack of trading cards of YC partners

To prepare for the interview, we found most of the questions online. We wrote out answers and used a Paul Graham simulation bot to try to rehearse them. Doing mock interviews with alum was the most helpful way to practice. Since YC has a strong community of founders helping founders, many are happy to do mock interviews and offer feedback.

When you’re reaching out to founders you don’t know, don’t start pitching your app. Be tactful. Make your communications short and to the point. Link to your product, say one sentence about it, write why you want to talk to them, and suggest a time window to talk for thirty minutes, including a ten-minute mock interview. To make it easier for anyone helping you, it’s good to be really specific with the particular points you want advice on.

How our interview went

After signing in at the headquarters, we found out which partners would be interviewing us and waited for our turn among the puffy vests. At 12:30, we were led down a hallway into a small room where three partners greeted us. The ten-minute clock started. Then two partners rapidly fired questions at us. “How are you different than Wakie?” “How much money will you make?” “What’s your North Star?” A third partner typed notes as we spoke. The interview ended abruptly with a loud knock on the door. We were cut off. Ten minutes goes by fast, and I felt like we didn’t get far into our product. We didn’t leave the interview feeling good.

Me and my cofounder debriefing our interview

Our biggest mistake

We pivoted at the last minute to seem more like a “YC company,” and this is how our interview derailed. In the days leading up to the interview, Max and I became worried that our idea wasn’t big enough. Instead of comparing Your Boss to WeWork or saying that we’re building an awesome accountability app for independent workers, we said that we were building “the next LinkedIn for self-employed people.” We changed our mission to make it sound more venture-backable.

A job platform isn’t what we want to build. Our core product is spoken one-on-ones and meaningful conversations for people who work alone, something I know a lot about as a self-employed person. People will find opportunities with the strangers they meet on our app, but we’re not building a job search app. Comparing our app to LinkedIn steered our interview in the wrong direction.

What I’d do if I did it again

  1. I wouldn’t have suddenly pivoted our product to seem more like a “billion-dollar-idea.” I think the interview would have been better if we had been ourselves and talked about our actual mission.
  2. I’d be more comfortable talking about revenue. I was able to crunch numbers on paper for the application, but it was difficult for me to talk about revenue out loud during the interview itself. It’s important to practice verbalizing your company’s revenue plans.
  3. I would have researched the people interviewing us while we were waiting. After signing in, we found out which partners would be interviewing us. During this time, we should have extensively researched them to figure out what we should say about our app that would pique their interests specifically.

Getting there matters more than getting in

Applying for YC made us think deeply about our product and gave us momentum to build it. Once we landed the interview we got off track. During the days leading up to the interview, we became misaligned with our mission because we felt like we needed to be a certain kind of company to get in. We were so close to being accepted and didn’t want to be turned away by seeming too small.

I won’t be applying to YC again because I’ve discovered so many other opportunities just by telling people about our app. We’ve had great meetings with other investors: investors who are aligned with our company’s mission and willing to take the time to understand us as founders. I wish I had been talking to other investors for the last few months instead of doing mock interviews or caring about YC’s game.

It’s easy to obsess over YC since there’s so much hype and cultural significance around the program. Sure, it’s a great community of founders, but there are other ways to meet founders without sharing the same branded hoodie from the same special club.

If you’re on the fence about applying to YC, my advice is to try it as an exercise and see what happens, but don’t think of it as the only path to growing your startup. Make sure you keep other options open, have ongoing dialogues with investors and CEOs, and don’t change anything about yourself or your company in order to beat the system and get in.


Danielle Baskin
Danielle Baskin is a entrepreneur, designer, and artist. Read about her exploits in Fast Company, Business Insider, BoingBoing, and The New York Times as well as, of course, here.

Hi there! This post exists to offer you (hopefully) useful information but it cannot take the place of personalized professional advice. Please consult a qualified expert if you have questions about your business. Also, Azlo doesn’t endorse any third-party sites that are linked here.


Icon arrow leftBack to Stories