Lessons from a failed YC pitch with Paul Graham

Last week, Kyle Wild and I sat down to talk about one of our favorite topics: failure.

Our friend Alan had given us the idea. He said it could be interesting to hear people with some degree of objective success talk about the times they had failed. He thought it could help new people coming into tech, or any field, cope with impostor syndrome and other fears.

I asked Kyle if any failure story came to mind, and he started laughing immediately: “Oh man, this is bad. This is real bad.”

“Excellent!” I said, and started up the recorder.

Paul Graham experiencing brain failure as Kyle Wild pitches Keen IO (then-named Schmetrics)

Kevin: Tell me about your biggest failure.

Kyle: Okay, when we were starting Keen IO, I went to this thing called Startup School, which is Y Combinator’s weekend of talks for aspiring entrepreneurs. They sent this thing that said, “Hey we’re going to have a couple people come on stage do live office hours with Paul Graham, the founder of our company. He’s going to demonstrate what YC office hours are like.”

YC office hours are like, there’s somebody on the pulpit who’s brilliant, and the lowly entrepreneur is going to sit down with them for an hour and talk. I was hoping to get an interview for Y Combinator anyway, so I said I’d love to do it.

Anyway, I’ve always had stage fright but for some reason I thought I’d be okay for this. When they announced my name I got text messages from friends. They were watching live, which made me nervous. So I go on, I don’t know what happened, it was a blur. It was bad.

Kevin: What was so bad about it?

Kyle: I was abstract, I was mean, I was futurist, I was a little too certain, I didn’t have any evidence, I was reasoning from first principles.

Kevin: How do you know it was a failure?

Kyle: Two things. Number one, we didn’t get into YC. That was painful. This is the biggest class ever. 80-something companies got into YC and we weren’t one of them, which feels shitty.

Then I jumped on Hacker News and there’s a post on “How Not to Talk to Investors” and it had two videos, and I was one of the examples of how not to do this, basically being publicly humiliated.

So obviously I didn’t go on stage for demo day when we were in Techstars the next year, and I didn’t speak at all again until two years later! Every time I’d think about public speaking I’d clam up and I’d think about how the internet is everywhere and if I fuck up people are going to refer back to it as a failure.

Kevin: What are your biggest regrets about it?

Kyle: Honestly one of my regrets is I stopped talking, I stopped going out and being me. I was afraid of being me. I’m a pariah in the industry. I’m on the do-not list of fundraising so how can I fundraise? On the do-not list of public speaking, how can I public speak?

I’ve become a fairly effective public speaker now and I’m getting better. It sucks to lose two years that I could have been working on that. Could’ve helped the company.

And I didn’t even feel like an impostor until somebody called me one and then I was just like, well, I guess I’m an impostor. It’s not because I think he’s right. I now know he wasn’t right. It’s because he said the stuff I was afraid of. That puts you on a bad path.

Kevin: What’s it like to have success after the worst thing you could imagine happened to you?

Kyle: Oh it’s fucking sweet. Like at KeenCon, I did the opening talk. I’m like, what’s the worst that could happen? Someone could record it and then write a post about how stupid I sound and it wouldn’t even be news! It’d be like, well it happened again.

Kevin: What does it make you think about failure in general?

Kyle: Failing at that investor talk in 2011, being shit on a little for that, once I came around, it made me feel pretty bulletproof. Well I failed, now what?

There’s a big difference between zero failures and N failures. When you have an N greater than zero, you’re fine. You know what it’s like. It’s not that bad.

This post was on Hacker News for a second and everything on Hacker News is gone in 15 seconds. I’m sure 1,800 people saw it and maybe 90 of them remembered it.

I did have somebody approach me who said they remembered it. Somebody was like, “I think I saw you on stage in an article about flubs or something.” I was like, “Oh was it an article like, look at these idiots?” He’s like, “Yeah.” This is somebody who approached me after a talk specifically because he liked my talk.

This is why I feel like fear of failure is one of those dangerous things. We should all push ourselves so hard we fail once in a while. I am a little disappointed in myself for not just getting right back on the horse. I had to process in my own way.

Kevin: You’ve talked to people who are going through various startup programs now. Have you given advice that relates to this experience?

Kyle: To some extent. This thing happened to me, maybe October 2011, and then October 2012 I went on a trip, Geeks on a Plane, and I met a coach who is an amazing person. Ed Nussbaum. He noticed I was clenching and freaking out because I was about to go on stage just to say, “Hi I’m Kyle, I’m one of the geeks. I work at this company Keen IO.” This wasn’t even a talk but I was freaking out.

He said something great. He said, “Kyle, you’re an improviser. You’re not a politician. You’re not a stump speech guy. You’re an improviser so what you need to do is give yourself permission to improvise.” Those are the exact words.

So what I started doing was before I go on stage I would just try to meditate. I’m not going to think about anything. I’m just going to stand here. Find a dot on the far wall and just look at it and be like, I wonder how big that dot is.

Just focus thoughts on shit that doesn’t matter and then they’d call my name and I’d be like, oh shit okay. “I’m Kyle, I work at Keen IO. We make an API that lets developers build analytics into their apps. Whatever kind of analytics they want. If you want to talk to me about it, find me after the show.” Really simple little sentence. I could never write that but I just made it up. Even just now, I just made it up. And that’s what I’m good at.

So basically, fuck the haters. It’s easy to find people who are going to call you an impostor. It’s harder to find people who are going to help you find your path.

You’ve just got to find people who build your confidence, listen to them, and find the people who shrink your confidence and just crush them out of your life. They suck.


Kyle improvising for the crowd at KeenCon

Post-script: At several times during our conversation, Kyle said I should try to find the article from Hacker News. But after half an hour of Googling, I gave up. It seems to have vanished.

I did find the video of the talk, though. Get ready to cringe a little…