How I F***ed Up In YCombinator

How I F***ed Up In YCombinator

We were walking around downtown Mountain View when Paul Graham (PG) gave us the news. “If this was a class in college, I’d be the professor warning you that you’re in danger of failing.”

We already had our suspicions, but he confirmed them. We were in YCombinator, and we were fucking up.

Let’s Rewind

Three months before that conversation, my cofounder Kevin and I were busily preparing for our YC interview. We applied with a programming education idea, with the tagline “Codecademy on steroids.” I had countless friends who were nearly finished with their CS degrees, and yet struggled to take their ideas from concept to finished product. I wanted to help them bridge that gap.

I had known Kevin since the start of college, but it wasn’t until our final year that we started working together. We were a solid team, a designer/developer combo. We had a plausible idea (or so we thought). So we applied to YC because, well, it seemed like the logical thing to do. After spending nearly two decades as a professional hoop-jumper, my choices were a) go to grad school, b) work at a big tech company, or c) attend a prestigious startup accelerator.

The Interview

Despite the fact that YC interviews are supposed to be grueling, we emerged from the interview room relatively unscathed. The partners (Garry, Kevin, Michael, and Geoff) questioned our business model and our ability to execute, but we had convincing answers. It wasn’t until our second interview that I understood why people called YC interviews grueling[1].

With a completely different set of partners (PG, Jessica, Trevor, and Robert), we had a completely different interview experience. We tanked. At one point, PG let out a long sigh and rubbed his forehead. “You’re halfway through your interview and I have no idea what your company does. This is not good.” I remember Jessica Livingston giving us a look that I could only interpret as total pity. We left dejected.

So you can imagine our shock when they told us we were in[2].

Impostor Syndrome

We were elated. Briefly. What should have been a very positive mindset quickly turned negative. For the first time in my life, I had impostor syndrome.

Impostor syndrome, if you’re unaware, is the belief that you do not deserve the success you have achieved or the position that you have reached. It’s the notion that, despite evidence to the contrary, you are just lucky, well-timed, or a convincing impostor. Amongst a cohort with more experience, confidence, and traction, I felt like a total fraud.

From the outside, it might have looked like I was crazy to feel this way. I graduated from Stanford, I had a CS degree, and I knew how to play the startup game[3]. But on the inside that couldn’t have been further from my reality. I was twenty-one, I had somehow gotten myself into YC, and I had absolutely no idea how to get a company off the ground.

On top of everything else, our mentors had just impressed upon us that our idea was stupid. So we pivoted.


Looking back, we should have found a way to address the partners’ concerns. We should have found a way to use the code we’d written and the domain expertise we’d gained. Instead, we threw out all of our data, all of our work, and started over.

And I mean really started over. We researched Bitcoins, smart devices, 3D printing, biometrics, and a host of other industries. After several days of brainstorming, FanHero was born. We came up with the idea after discovering how little money most YouTube personalities make. Our thesis was that if you produced content that millions of people consumed on a regular basis, you should be able to make a living from your content[4].

Like many arrogant twenty-something recent grads, we assumed we could write a bit of software and disrupt an entire industry. We had no experience creating or maintaining an online following. And we had no YouTuber friends who we could get initial feedback from. From the outset, it was an uphill climb.

We still had faith, however. Faith that we just needed a critical mass of users. Faith that we just had to iterate a few times on the product. Faith that we would get a TechCrunch writeup, and it would solve all of our problems.

And then we “launched.”

Every YC company can have TechCrunch write them a launch article, if they want. Few decline, since it’s free launch press. In our case, it’s unclear if we made the right choice.

In the words of the reporter:

So anyway, there’s this company called FanHero. It’s all about helping those YouTube guys make money in, like, non-advertising ways. Giving the community ways to support them through commerce — you know, selling stuff. It’s like the classic merch model, like how you go to your favorite band’s show and you buy a t-shirt or a CD.

The guys behind FanHero are these Stanford CS undergrads Kevin and Charlie, who like, grew up on YouTube idolizing YouTubers. These guys don’t remember a time when the world’s biggest stars weren’t on it. They’re in Y Combinator now because that’s where all the cool kids go to learn about the Internet and monetizing and stuff.

We had much bigger problems than the piece, to be sure, but launching with an article that roundly mocked us was one of the final nails in the coffin. That’s when we received an email, informing us that we were being summoned for office hours with PG.

The Meeting

He was brutal, but he was honest. Our company was in awful shape. So with less than five weeks to Demo Day, we pivoted. Again.

We went back to PG, and he told us to stop worrying Demo Day. With the right idea, we’d be working on the company for the next five-plus years. It was foolish to sacrifice the quality of the company to optimize for the next five weeks. Instead, we should look for technologies that were interesting to us, as well as larger trends that we observed in the industry. To his credit, this is very, very good advice. When you’re a 21 year old trying to start a startup first thing out of college, though, it’s hard to internalize that advice.

To be honest, the last few weeks of the program are a bit of a blur. My morale plummeted, and my stress skyrocketed. I dreaded going to the weekly dinners. I did little else but eat, code, and sleep. I felt like everyone else was ready to raise millions, while we were desperately trying to find a product. There was no way we could compete with our batch mates on Demo Day.

A Way Out

Then the partners told us that we had the option to defer Demo Day, if we wanted. It wasn’t common, but other companies had done it. When they told us, I felt an incredible sense of relief. Postponing Demo Day was a no-brainer. We didn’t have an idea we believed in, and although we could have cobbled one together and raised some seed funding, we didn’t want to do that. I didn’t want to do that. Partly because it was disingenuous. Primarily because taking half a million dollars of other people’s money would have moved my stress level from unhealthy to crippling[5].

But skipping Demo Day didn’t fix our lack of conviction. The rapid-fire pivoting continued. Around this time, I started coming to terms with the fact that I was seriously unhappy. For as long as I’ve been interested in startups, I have never wanted to start a company for the sake of starting a company. I’ve always been adamant about this. Yet doing things "for the sake of starting a company" was where I found myself, desperate and scrambling for a plausible idea.

I don't know if this is true for other people, but as a flailing founder I desperately wanted to believe in the startup myth. The myth that success was just over the next ridge, that if we waited a bit longer, or had a slightly better idea, we would suddenly be riding a rocketship.

I hated doubting myself, but I've never been good at blind faith.

So I decided to leave.

I Left My Heart In San Francisco

Since then, I've taken a break from startups. I still love Silicon Valley, and I know I'll eventually end up back there, but in the meantime I'm having a lot of fun doing remote software consulting and exploring the world[6].

I don't regret my experiences in the slightest. Sure, I might have done things differently if I did them again, but I've more or less landed on my feet. I've taken a significantly different path than I could have predicted (which isn't a bad thing), and as cliched as it sounds, I've learned a ton, both about myself and about how startups work. The latter has helped friends who are running their own startups, and the former has helped me figure out what comes next.

P.S. I'm putting together a book! It's a collection of interviews with startup founders on the topic of "Do Things That Don't Scale", a fantastic essay by PG.

P.P.S. I'm also working on tackling software projects that need to be done by more than one person. If you're interested in being part of a distributed team that works on a slew of different types of projects, hit me up.

Huge thanks to Alexey Komissarouk, Casey Rosengren, and Ruth Marks for reading drafts of this.

[1] This is, if you’re wondering, pretty unusual for the YC application process. Most teams only do one ten-minute interview and then go home. The partners make a decision by the end of the day.

[2] After our interview, we had absolutely no idea whether we’d get it. So we went out and bought a bottle of champagne, and a bottle of whiskey. The champagne was for if we got in. The whiskey was for if we didn’t.

To this day, I remain convinced that our saving grace was a little-known fact that we demonstrated in the interview: when you bite into an apple-shaped plastic bottle of Martinelli’s apple juice, it sounds like you’re biting into a real apple. No, seriously, check it out.

[3] YC was not my first startup, or my first accelerator. During college I had started an ed-tech company, ClassOwl, which went on to raise nearly a million in seed funding. We went through StartX, but ultimately decided to finish our degrees instead of pursuing the startup dream.

[4] And it would appear that the market is proving this thesis correct, for now. Patreon is growing at a rapid clip, having raised a $15 million Series A. Even Google is getting wise, having finally added “donate” buttons to YouTube channels to let people monetize their fans.

[5] Not to mention we would have been on the hook for another 2-3 years. Changing your mind about being an entrepreneur isn’t taken too well, even if you return most of the money.

[6] So far, I've visited Japan, China, Thailand, Greece, Costa Rica, Nicaragua, and now Argentina. Not to mention half a dozen states back home. Humblebrag, I know.

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