Getting into YC: Tips, Tricks, & Tools for Success
So, you have an idea or early version of your product, and decide to apply to Y-Combinator (a seed accelerator that invests in a large number of startups twice a year, and has launched the likes of Dropbox, Airbnb, Stripe & more). There’s probably a lot on your mind right now, so we decided to share the experiences of YC alumni, Kristen Tyrrell and Gillian O’Brien, about building an early-stage startup and what it takes to get into & succeed at Y Combinator.
Kristen is the Founder & COO at Catch (YC 19), a FinTech startup that is working to build a modern safety net for the modern workforce, and Gillian, Co-Founder & CEO at Cherry (YC 19) is working to build a flexible benefits solution, which lets employees choose their own workplace perks. They walk us through their startups’ early days, the YC application process, and their biggest takeaways.
Many people have grand ambitions and great ideas that could change the world: Could you give us the background behind your startup and talk a little bit about how to choose what projects to work on?
Kristen: We chose to work on Catch because growing inequality and the changing workforce are making more Americans vulnerable. We’re rebuilding the safety net to automate tax withholding, retirement, health insurance and more for workers who don’t have access to employer benefits. It’s a problem 80 million people in this country live with every day. I’ve been in FinTech for about 5 years. My cofounder was a freelancer living without benefits. We saw so clearly how things could be better and decided to build it ourselves.
Gillian: The company I worked for prior to starting Cherry was very perk heavy, specifically in the food department. Sadly, I have severe food allergies so I never really got to “engage” in these perks. I wished I could instead get the money back from the company to use towards something else that would make my life easier. I was a typical millennial in the workforce; trying hard to balance my health, relationships, family and career—I wanted my company to help me save money on my commute, or my gym membership.
My co-founder is my sister. We knew we wanted to work together for a long time - so when I shared my challenges with her, we got super excited about building a solution. Inclusion is a priority, yet a very real problem for most companies when it comes to culture, perks, and benefits. We’re building Cherry because we want to change this. The workforce is more diverse than ever, and people have very individualized needs. Cherry is the clear solution for the modern company so that each employee can choose their own benefits, rather than be restricted to one offering.
Once you figure out what to work on: How do you advise people to find who they're working on things with?
Kristen: Be everywhere you can be. There isn’t necessarily a magic formula for finding people to work with, so be prepared to let things happen organically. If you don’t already have a cofounder in mind (a sibling, former colleague, school friend, etc.), you may find that person somewhere you least expect. It could be a meetup, a hackathon, or a coffee shop.
Gillian: I’m a strong believer in potential. Your team doesn’t need to be perfect - they need to be scrappy, passionate, committed, and persistent. Starting where you are and looking at the people you’re closest to is a good start. Take a risk and explore the potential in the network you’ve already built. People might surprise you.
So you've selected what to work on, who to work on it with, now how do you actually get things done? What are the best ways to actually accomplish big things?
Kristen: Start by doing. Vision is important, but not nearly as important as execution. You have to meet your customers, take the hard feedback, and iterate. Your product will *never* be finished, so you may as well start getting people to use it as quickly as possible.
Gillian: Don’t overthink it, just start. Theorizing the best way to accomplish something will put you in analysis paralysis mode. What’s important is that you actually execute, learn, and iterate. It’s okay to learn as you go.
Why did you choose to apply to Y Combinator?
Kristen: My cofounder and I were somewhat “unbranded.” We didn’t go to an ivy league school, work at Google/Facebook, or have a previously successful exit. We’re also based in Boston. For us, going to YC was a chance to have some really smart people validate our product and to build our network in San Francisco. It dramatically accelerated our fundraise and gave us some brand clout, which is powerful as you build partnerships.
Gillian: We really believed in the value of the program and felt there was so much we could learn. We respected the partners and wanted to work closely with them. We wanted to surround ourselves with other dedicated founders. We knew that the network and access to investors would be significant.
Did you apply with promising early results, tests, or product usage. If so, what did that did that entail?
Kristen: We had an early, EARLY, MVP that had almost 5,000 users on it. The core mechanisms of our product worked (linking bank accounts, identifying paychecks, moving money, holding money), but we were still a long way from the product we knew we needed to have to prove product/market fit. Our contracts with banks were in place, we had people actually moving money, but unfortunately, in FinTech, those are somewhat table stakes. Old-school SaaS companies used to just be able to build a waitlist to demonstrate demand. More complex product offerings sometimes require legwork to prove out a proof of concept (for us, that was a year + of work and meaningful acquisition).
Gillian: We were on the early side of YC applicants. We had an idea and a demo of what we thought our product functionality might eventually be like. We had no users at the time, but we had our personal experiences and hundreds of user interviews that emboldened us to believe that a solution like ours had to be a part of the future, that this was a real pain point.
How did you approach the written part of YC application?
Kristen: We were factual. We didn’t use too many adjectives to try to oversell our product or company. We were transparent about where we were and honest about the challenges (and upside!) that we saw. We sold our big vision, but we were clear on the execution we had already accomplished. It was important for us to make clear the real problem we were solving; people don’t know what financial and insurance products they need, they don’t get employer benefits, they have increasing income volatility. It’s easy to understand those problems, and we had evidence from user testimonials that proved we were solving them.
Gillian: We were straightforward and concise. We didn’t use any marketing jargon or try to sell. Instead, we tried to say as much we could in as few words as possible. There is a real human on the other side of the application, who has probably read thousands of them. For that reason, we didn’t want to obfuscate. We made our answers as clear and easy to understand as possible.
Can you tell us about your interview experience?
Kristen: The questions are pretty standard to what you find in online resources (if you get an interview, YC sends you links to many of these resources). They’re also very similar to questions VCs ask you if you’ve tried fundraising before. Because we had already met with at least 100 VCs, the questions weren’t surprising, and I think this helped us keep calm. We didn’t do any additional preparation. The biggest difference is the brevity. Knowing your stuff, not trying to over-explain, and being very clear on the answer to the question can go a long way. We were asked about our customers, our vision, our product, and the need we were solving. We were brought back in to discuss our burn (we already had a team of 12). They were concerned we were going to run out of money, but we made it clear our priority was making the company successful, and we would take necessary steps to ensure that happened. I think it was valuable for them to see how we thought not just about our product/solution, but about our business. After you launch an MVP, you spend more and more time being a business owner and your team takes more and more control of product. That transition can be tough, but I think our approach to the company gave confidence that we were ready for it.
Gillian: Our interview experience was intense and exciting! Once the interview date was confirmed, we scoured the internet to find every blog, comment, or quora post of an applicant's YC interview experience so that we could review the commonly asked questions and prepare ourselves. You only get ~10 minutes in the room with the partners, so it’s important to make the most of that time. My approach was to put each question on a flashcard, study it, and then have friends (and willing YC alum!) give me timed mock interviews. This helped me refine my answers, keeping them short and powerful. Remember that the interview process is an opportunity for the partners to get to know you - not just your business. It’s also how they’ll get a feel for the relationship between you and your co-founder.
Do you have any other YC application tips?
Kristen: Be honest and clear. Simple insights go far.
Gillian: Do your homework. Read up from YC directly about what they’re looking for. Listen to the YC podcasts and the lectures on YouTube. Read some original YC applications, which are available online (Dropbox, The Muse). There are so many resources available to help you get in. Use them!
What was your biggest takeaways from Y Combinator?
Kristen: There was a session that described being a founder as a series of mini-games. For me, that was a really interesting way to think about it. Your role changes constantly, and some things you succeed at right away and others are HARD for a long time. Putting that frame on your responsibilities can make it more comfortable to change what you do every day and not hold on to any job/task too tightly.
Gillian: YC emphasizes that your focus should always be on your business; your customers, your users, and building things people want. As a founder, there are a lot of other things that can pop up and be distracting: press, competitors, valuation, big fundraising rounds, investors, advice from peers… it’s important not to get caught up in this. Listen to your users and believe in what you’re building.
If you could leave one piece of advice for female founders/entrepreneurs, what would it be?
Kristen: Don’t be afraid to try and fail. If you aren’t good enough today, you can be better tomorrow (growth mindset changes everything).
Gillian: I’ve encountered so many female entrepreneurs that have imposter syndrome. When they compare themselves to other people in the industry, I always want to ask: “if they can do it, why not you?” Look at all of the successful founders in the world - men and women alike. What makes them so different from you? It seems oversimplified, but just remember; if they can do it, you can, too.
Kristen Tyrrell is the Founder & COO at Catch (YC W19), a technology startup combining savings, investment, and insurance for those without access to employer benefits. To date, Catch has raised $8.1M from the likes of Khosla Ventures, NYCA, and more. Before building Catch, Kristen worked various roles in consumer FinTech and banking integration and has a Masters in International Business from Hult and Bachelors in Mathematics and Economics from Pepperdine University.
Gillian O’Brien is the Co-Founder & CEO at Cherry (YC W19), a flexible benefits solution for the modern startup that lets employees choose their own perks. Besides funding from YC W19, Cherry is backed by angel investors, Orange Seed and Productive VC. Prior to building Cherry, Gillian graduated from New York University with a Bachelor’s Degree and worked at various tech startups in New York City.