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8 minutes

Y Combinator: The Story of Our 3.5 Interviews

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Picture this: Y Combinator requests to interview you for the W24 batch. Then, after the first interview, you get a request to chat with a partner for 30 minutes to evaluate new ideas. Eighteen days later, you show up to the Zoom meeting with an entirely new product, launched MVP, and 80+ waitlist signups. Instead of a decision, you get another interview scheduled in 24 days. Then, after the final interview, you get an email denial 22 hours later. How would you feel? Stressed? Relieved? Devastated? This is what happened to us during our first Y Combinator interview cycle.

I’ll break down the interview questions and why we didn’t get in.

NOTE: We interviewed again for S24, but knew that we’d be denied before interviewing because Rivit isn’t positioned well to become a multi-billion dollar company.

YC Interviews: Questions and Style

Interview #1: October 31, 2023

My memory is hazy from our first interview. The pressure was immense. We had built a tool that automated emails to help job seekers get interviews. Our growth metrics were strong — $0-3K revenue in the first three months. Our team was exactly what they were looking for — two founders, one salesperson, and one engineer — both with strong track records.

We prepped for a few days beforehand, studying our metrics, competitors, business, and YC interview questions. The best interview practice tool we found was James Cunningham’s YC interview question generator. Shoutout James Cunningham!

We completed all our prep work the night before and did a quick one-hour warm-up session before the interview. Then came the moment of truth; we joined the Zoom room and met Pete Koomen and Aaron Epstein in the first 15 seconds. They then, in true YC format, rapidly asked us questions for the next 12 minutes.

Interview Questions:

  1. What are you building?
  2. Who does what?
  3. How do you know you’ll continue to work together?
  4. How are you going to scale?
  5. How are you acquiring customers?
  6. Have you (the founding team) met in person?
  7. What if LinkedIn copies you and crushes you?
  8. What’s your competitive advantage?
  9. Who are some of your competitors?

That was it. The interview flew by. We felt like we did as well as we could have, but had no clue how they felt.

Interview #1.5: November 18, 2023

Within 24 hours, Pete emailed us, saying that he and Aaron liked our product velocity and growth, but not our business model. He proposed that, if we were open to other ideas, we should chat about them during office hours in a few weeks.

This motivated us to build and sell a new product as quickly as possible so we could impress Pete and hopefully be accepted after the office hours.

Office Hours

About five minutes into the conversation, Pete proposed we do another interview in a few weeks. This surprised Eric and me because we thought we had a chance of receiving a decision after that call. After that realization, we chatted with Pete for another 30 minutes about the future of OpenAI, the trajectory of our new company, Rivit, and how we would fit into the AI ecosystem.

Pete wasn’t sold on our direction because of our similarities to the newly launched GPTs, so we set to differentiate ourselves over the next few weeks before our final interview.

Interview #2.5: December 12, 2023

We’d done the same prep work as interview #1 and went in ready to fire. This time, it was Pete and Tyler Bosmeny. Major shoutout to Tyler for making us feel super comfortable during the interview. He smiled nearly the entire time and helped calm our nerves.

Interview Questions:

  1. What have you built since your last interview?
  2. Can you explain the scope of your product? What is the vision?
  3. What is the overall problem your product solves?
  4. Why did you guys decide to work on this idea?
  5. Do you have anybody using this?
  6. You've had 80 people sign up for the waitlist, but has anybody signed a contract? Is anybody actually using the product?
  7. What was the need that got [company name] to you?
  8. How did you find [company name] and what was the pitch?
  9. Have you guys met in person yet?
  10. Do you plan to meet in person and build the company remote or co-located?
  11. Are you both full-time on this yet?
  12. If I could give you 1000 leads, how would you describe the exact kinds of leads you wanted for this?

The interview lasted 14 minutes. A bit longer than our first interview, so we at least thought that was a good sign. Eric thought we did okay, I thought we did well. Eric was right. At 11:09 PM PT we received a denial email. We were more relieved than anything because we could go back to building Rivit without stressing about the interview process.

Interiew #3.5: May 6, 2024

Eric and I reapplied on a whim to S24. A few days after applying we received an email telling us we had an interview in two days. We were slightly surprised because of Rivit's trajectory, but excited nonetheless. We tried our best to build a business plan that would make sense to Y Combinator, but at the end of the day, Rivit isn't set up to be a billion dollar company. We've made a conscious decision to bootstrap and build a profitable business rather than aspiring to build a unicorn. Read more about this in our article on "Why we're bootstrapping Rivit (and why you should boostrap too)."

Interview Questions:

  1. What are you working on?
  2. Why this?
  3. What is your approach, why do small businesses need this, and what have you learned from them?
  4. Are you helping small businesses build a knowledge base that they didn't have before?
  5. Do you have customers already, and can you tell us about one of them?
  6. How do you feel your approach will break through in a competitive space with many companies trying to become AI customer support chatbots?
  7. What are your thoughts on the statement that consumers hate chatbots, and how do you see chatbots evolving in customer service?
  8. How are things going between you and your co-founder since meeting through co-founder match, and how do you ensure this is a long-lasting partnership?
  9. Why haven't you met in person yet?
  10. Do you plan to build the company remote or co-located?
  11. Who is your ideal type of customer, and who are you explicitly not trying to serve?
  12. Do you want to keep serving small companies as they grow, or will they eventually switch to larger platforms?
  13. Are you aiming to disrupt existing incumbents in the larger enterprise space, or is there a huge market in small businesses that incumbents are not serving well?
  14. Selling to small businesses is notoriously painful; what is your strategy to reach a lot of them quickly?

This interview went swimmingly. Tyler joined us again along with David Lieb. We nailed all the questions, but deep down, we knew that Rivit likely wasn't a fit for Y Combinator. We found out at 10:18 PM PT that we didn't get in for the exact reason we suspected—a highly competitive market.  

YC Feedback: Why we didn’t get in

W24: Newness isn't an excuse for bad fundamentals

The main reason we didn’t get into the W24 batch is because we didn’t know who we were serving. We knew the problem we were solving, but we hadn't identified who had the problem or if anyone would be willing to pay us to solve it. We ended up pivoting after a few months of struggling with this problem.

S24: Fierce competition is great (in some cases)

Customer support software is a hotly contested space. There are hundreds of startups and incumbents battling for market share. We are in the arena competing for market share. This is great for a bootstrapped company because it is clear you're making something people want. You can carve out a niche and build a profitable company. However, it's extremely tough to build a billion-dollar company in this environment. Y Combinator rightly identified that we would struggle to build a unicorn in that environment.

Thanks YC!

Massive shoutout to Pete, Tyler, Aaron, and David for interviewing us and giving us feedback. The interview process helped us identify gaps in our company and accelerated our progress tremendously.

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