For the first time in my life I have a chip on my shoulder

Last week I received a rejection email from YC for the winter batch. It’s not the first time I’ve been rejected, I had an interview a year ago and didn’t get in, but it’s the first time I’ve really felt the pain. What made it sting even more was the fact that the 6 other companies that applied from my co-working space all got interviews. Startups are all about beating the odds, we just beat the wrong ones. But there’s a silver lining:

For the first time in my life, I have a chip on my shoulder.

Over the last few years, I’ve read countless articles about entrepreneurs having chips on their shoulders. Investors look for it since it’s an indicator of persistance. When you’ve got something to prove, you’re more likely to blast your way to success. But how do you actually get this fire?

Some people have it as part of their personality. Others get it from being told they can’t do something and needing to prove their detractors wrong.

Me? I’ve never really had it. That’s not to say I haven’t been working really hard, just that there’s a gap between “hard-working” and “needing to prove something”. I’ve always been told that “you’ll do well in whatever you do”, and while I realize how lucky I am to have such a supportive group of family & friends, blind positivity doesn’t exactly light a fire under you.

But now I have it.

Instead of shrugging it off like any other rejection, this one was internalized. The picture above is the rejection email that I’ve taped on the wall next to my desk. I see it countless times throughout the day. And with a chip on my shoulder, I find myself more focused, thinking more clearly and getting stuff done. It’s been one of the most productive weeks of my life. And I love it. By no means is it the way I wanted it to happen, but at the end of the day, it’s been a huge net positive.

5-10 years from now, when the majority of people are using Tripzaar to plan their trips, I want this rejection to look ridiculous. For hindsight to be “how could anyone have thought this was a bad idea?”. That’s the goal I’m obsessed with now.

So thank you YC. Thank you for the rejection and lighting a fire under my ass. I have no hard feelings to you (or others that got the interview), and will likely apply again in the future. But I have every intention of using this rejection as my Leroy Smith.


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  • Eli Porter

    >5-10 years from now, when the majority of people are using Tripzaar to plan
    their trips, I want this rejection to look ridiculous.

    Do you honestly believe this?

    Maybe instead you should take it as a hint that your idea is terrible, and you should put forth your efforts into something that people would actually use.

    • Andrew Cross

      More fuel to the fire :)

    • Daniel Miessler

      Eli, that seems quite negative. And that doesn’t mean always be positive when negativity is needed, but how about instead saying that he should vette his idea again with multiple sources to determine whether it’s a bad idea or the implementation needs help.

      The notion that good ideas don’t get rejected is not only false at this point, it’s ridiculous.

    • Toby Sullivan

      Is this actually a serious comment? Am I missing some inside joke? Wow. Very destructive.

    • Guest

      He’s the best mayne

    • brian piercy

      Absolutely more fuel to the fire. Give ‘em hell Andrew.

    • Stephen Pedrosa Eilert

      Y Combinator is full of extremely smart people that all have seen many startups and thus are possibly more like to make smart judgments. However, even they make mistakes.

      How can you be sure his idea is terrible? The answer is, you can’t, so either give some constructive, objective criticism or shut up.

      He might quit now, he might succeed with this exact idea, or he might pivot.

      Andrew, startups never die mid-stroke. So keep typing. (quoted straight from PG).

    • cmc

      Oh My. Seriously, I found PG’s essays very inspiring and I wish Elon Musk would write some. But in the end, you want to be like the people you admire, not their acolyte. So, for what it’s worth… go for it, chip man!

  • Vlad

    A bit off topic, but what is the coworking space where you work?

  • jonathanjaeger

    Love your landing page. I personally don’t like the idea for the company as a business — it’s not a BIG idea that YC would like. It’s possible you could make a lifestyle business out of it, but one glaring problem is you have a big chicken-and-egg business on your hand. It’s going to be tough, but I like your resilience.

    • Andrew Cross

      Thanks. 100% agreed there’s a big chicken-and-egg problem and it will be huge challenge. We’ve got a few things we’re working on though to hack it.

  • aaminpour

    Good luck!

  • Aaron G

    Interesting idea! I just signed up and I look forward to receiving the invite. Good luck with it.

    • Andrew Cross


  • OliverCardoza

    way to be! ill be watching tripzaar :)

  • Jesse Rodgers

    About time ;)