My Y Combinator interview experience (W18)

[Updated Nov 27, 2021] Four years later, I’m happy to report back - My company Listen Notes thrives without YC :)

Front desk of Y Combinator HQ

I want to be transparent on the process of building Listen Notes, as a product and as a company. If eventually I declare failure of this startup thing, these written documents may still benefit people who come from Google search :)

Spoiler alert: I got rejected in the end.

A bit contexts here, if you come from Google search and don’t know who am I and what is Listen Notes: I’ve been working on a podcast search engine called Listen Notes full-time since mid September 2017. It’s self-funded and it’s a one-person company as of this moment (Jan 2018). And I’m based in San Francisco.

Y Combinator should need no introduction. Most early-stage startups in Silicon Valley (and around the world) want to apply to it. It’s not about the money they give you — they’ll give you $120k for 7% of your company, which can barely hire a software engineer in San Francisco. It’s about the “Y Combinator” brand. It’s a new kind of label that automatically gives you tons of free PR & further fundings from top-tier VCs. A lot of founders put something like “YC W18” on their LinkedIn profile or their email signature, which is something worth showing off. But being accepted to Y Combinator doesn’t mean you’ll succeed as a business. It’s like not every Ivy League graduate has a happy & successful life.

I applied to Y Combinator 7 times before, when I still had a day job. Obviously, I got rejected every time. It’s actually understandable. Look, I’m an immigrant and I didn’t have green card back then, which means that I didn’t fully commit to this startup thing and I was not quite serious about it. I didn’t work full-time on my idea, I was a sole founder (it’s still true now; it’s well-known that most investors don’t like sole founders), and my previous ideas were really too obscure for non-Chinese speakers to understand. So, Y Combinator has one million good reasons not to invite me for interview.

This time is different. I started to work on Listen Notes full-time for a couple months. I’ve got green card, and podcast is something not too obscure to English-speaking techies in Silicon Valley. So I applied to Y Combinator again in late November 2017 — it well passed the application deadline; but it turns out that YC has this late application thing. Surprisingly, I got an invitation to interview with them in Mountain View several days later.

The interview day was December 5, 2017. I went to Mountain View during day time and I got a rejection email at night on the same day. Overall, the experience was quite pleasant and the process of preparing & doing the interview really helps you to think deeply on your business. I highly recommend all startup founders to apply to Y Combinator.

So here’s what happened.

On December 5, 2017, my wife drove me to Y Combinator HQ in Mountain View. My interview was at 3:15pm, but we arrived around 12:30pm. Just like every other founders, we took photos with the Y Combinator sign outside their building. Listen, there’s a business opportunity: on YC interview day, come to YC HQ and take photos for startup founders. You can easily charge them $5 each and they’ll happily pay. Haha.

YC HQ is an ordinary one-floor building. I typed in my Hacker News username at the front desk and got this:

From the printed sticker, it was Interview Day 8 for this YC batch (W18). If I remember correctly, there were 8000 ~ 9000 applicants and they invited ~500 to interview (across 8 days). They accepted ~150 in the end.

There were three tracks for interview. Each track was in a separate small room, with 3 or 4 YC people. Each team had 10 minutes to be bombarded with questions. Then you had to hang out there for another 1 hour or so, in case they wanted to re-interview you again.

What did founders do there, if they were not in the interview room? Well, before interview, many founders pulled out their phone / tablet, read the screen, and talked to themselves — yes, they were practicing those interview questions. I didn’t do this kind of practicing there. I thought it wouldn’t make any difference. I just chatted with founders who looked relax — you can easily tell that some founders were quite nervous. I learned that many teams had been working on their idea full-time for at least one or two years. Some had pretty good revenue. Some had a big team already. Some had awesome hardware prototypes, e.g., e-bike, e-helmet, huge VR devices or the like. I talked to myself, well, Y Combinator should accept those teams before accepting me. What qualifications did I have to be accepted here? I just got started for a couple months and the thing I’ve been working on seems to be less impressive than those e-bikes, e-helmet, VR devices…

Backyard of YC HQ

Finally, it was 3:15pm. I was summoned into a small room. It’s like walking into the Jedi Council, haha. There were four YC people in the room. I recognized 2 of them (YC partners), because I had watched their talks on YouTube. I didn’t know the other 2 (not YC partners). They were sitting in a row, on the same side of a long table. I was sitting on the other side of the table. I brought in my laptop and several printouts with graphs of website traffic, podcasts growth, and the like.

Once I got in the room, I shook hands with each of the four interviewers. There was a 10-minute countdown clock on the table. One of the interviewers didn’t say a word during the entire interview session. The other three interviewers bombarded me one question after another. I was fully aware that they would be very direct and sometimes feel rude, as described in an email that was sent from YC the day before the interview:

The partners may interrupt you, be abrupt, ask multiple questions at once, or ask questions you’ve already answered in your application. Please don’t think that they’re being purposefully rude. They’re trying to maximize the short amount of time they have with you to make a big, life-changing decision (for all of us).

These are some questions I got asked — there may be more questions, but I forgot:

What are you building?
Who will use your product?
Why do people want to use your product?
How big is podcast industry?
What’s the roadmap of Listen Notes?
How do you make money?
How much money will you make per year?
How many searches do you get per day?
…

I was actually doing a good job there. I was calm and controlled my pace well. I couldn’t change the cards in my hand (e.g., my experience, my age, being a sole-founder, my college degree, my accent, my project,…), and that was the best I could play the cards. I didn’t get a chance to give them a demo on Listen Notes — but I don’t think this would make any difference.

Before time was up (~30 seconds early), they ended the interview. So I knew that they already lost interest in me and they already made up their mind during the interview. Before exiting the room, I knew for sure it would be a rejection, 100%. I stayed outside the room for another 45 minutes or so, and I was informed by an assistant that they didn’t need to reinterview me. Then, I left the YC building and headed to Sizzling Gourmet in Cupertino to have dinner with my wife :)

While I was enjoying my dinner, I got this email from YC:

Subject: YC

Hi Wenbin,

Unfortunately, we’ve decided not to fund Listen Notes. You’re a smart, technical founder, and your traffic — 40k monthly uniques — is impressive, especially for how long you’ve been working on this. It sounds like you’re expecting podcasts to grow into what websites are today, but we’d like to hear how that happens. How can podcasts generate the same/more revenue? Also — this is an extremely crowded space. We left the interview not fully understanding how you win it. The insight to use meta tags for search doesn’t seem like a lasting competitive advantage that would allow you to build a huge standalone company. Best of luck as you build the business

</ rejection>

I didn’t feel upset or anything. It’s actually a pretty positive signal for me. Being invited to YC interview alone is already some kind of validation. If I sit on the other side of the table, would I accept this Listen Notes team? Probably not. Investors are here to make money. They are not here to do charity. They need to bet on the right team. Those YC interviewers were running binary classification in their heads, where output is Yes or No, and input is a set of features. Let’s look at some features of the Listen Notes founding team (aka, me):

Sole founder / Single-person company.
1st generation immigrant & non-native-english speaker.
Didn’t go to Stanford or Ivy league schools.
Old. Yea, I’m not 21 or 22. I’m 32.
1st time founder & no exit before
Full-time on this idea for just 2 months
It’s just a “I can build this in a weekend”-ish website

Given these features, the investor binary classification would immediately output a big NO. It would be a hard sell. As far as I know, Y Combinator never accepted a founding team with such combination of attributes: old, sole founder, single-person team, 1st generation immigrant, non-native-english speaker, non-Stanford/Ivy league graduate, 1st time founder… Unless Listen Notes were having 100 million page views per month or I were able to magically change some features above (maybe use time machine, magic or the like), I definitely had no any chance to be accepted. Listen Notes founding team just doesn’t fit in the stereotype of founding teams of YC companies.Think about the founding teams of Airbnb, Dropbox, Reddit, Coinbase, and so forth. I’m nowhere similar to them on picture or on paper. Well, this is life. There are a lot of things you can’t control. But there are far more things that you do have control. Keep going. Don’t give up too early :)

Actually reading between lines of the rejection email, it’s very obvious that they didn’t think that I’m good enough as a founder. It’s not about the idea. We all know that many many YC companies changed their ideas multiple times. Yea, I have a lot of work to do to prove myself. This takes time to practice.

I still think Y Combinator is a wonderful organization. I’m not unfamiliar with rejections (e.g., applying to graduate schools, submitting academic papers to conferences / journals, immigration things, …). But YC is the only one that gives me feedback, explaining why they rejected me. As I said before, the process of preparing Y Combinator application & interview is totally worth the time, because the process forces you to think deeper.

I’ve seen people who grew up in privileged families became super depressed and went to see therapists after getting tiny rejections (e.g., negative comments on their projects or people didn’t reply their emails)— those people hadn’t faced any difficulties growing up, so they didn’t get enough “rejection trainings” when they were young. It’s good to be rejected again and again when you are young. You can’t go to Olympics without any training, right? For most people, their Olympics moments are not in their teens or twenties or even thirties. It’s in forties or even fifties when there are aging parents to support, young kids to raise, mortgages to pay off, layoffs to deal with, midlife crisis to worry, and all kinds of serious issues.

Anyways, this is my YC interview experience. Maybe I’ll apply to YC again. But for now, I get to do the work :)

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My Y Combinator interview experience (W18)

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