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Cockiness is simply false confidence. It’s acting confident without anything to back it up. At first glance, cockiness and confidence can sometimes look very similar. But once you start asking for details, it becomes much easier to tell the difference.

When I’m in an investor meeting with an entrepreneur who says something that sounds cocky, I don’t immediately make a judgment — I just ask for backup on their statement. If the entrepreneur then goes on to say, “I’ve done this research, here’s some data, let me show you,” that’s confidence. A cocky person will respond with something along the lines of: “I just know it.”

I once met an investor who said he could tell if a startup was going to be successful within the first five minutes of meeting the founders. But of course, he had no data, no algorithm, no track record to back up his statement. Cocky people never say where their self-assuredness comes from, they’ll just assert something without supporting it. Once you start asking for details, you can sense that they’re hiding something. Confident people, on the other hand, are willing to answer any question and go deep on what they’re confident about. Since they’ve done the work, they don’t have anything to hide or cover up.

Another indicator of cockiness is that it usually sounds like bragging, whereas a confident person tends to come across as humble. When meeting with investors, your confidence and humility will shine through if you’ve done the work and have the data to back up your claims.

This post recently appeared on The Accelerators at the Wall Street Journal, where startup mentors discuss strategies and challenges of creating a new business.

David Cohen
(@davidcohen) Founder & Managing Partner of Techstars, previously founder of several technology companies. David is an active startup advocate, advisor, board member, and technology advisor who comments on these topics on his blog at DavidGCohen.com

  • 270951763040589

    It seems paradoxical that confidence and competence are inversely related, but that’s exactly what the Dunning-Kruger effect shows. Exactly as you noted, the competent person is often humble, while the “cocky”, over-confident, person is almost certainly full of hot air!