Know that queasy, stomach-churning feeling you get about 15 minutes after leaving a meeting that you absolutely bombed? You say to yourself, "that was the most embarrassing thing ever"?

Of course, we've all been there. It's not unlike those awkward high-school moments where you blurt out the wrong thing to someone you've had a major crush on. This feeling is the worst. And while many of us--hopefully--leave these pubescent gaffes firmly in the past, when they rear their ugly head into adulthood, the feelings naturally come welling back.

And if not a love interest, the corollary in the world of entrepreneurship may well involve a pivotal meeting with a potential investor, which you absolutely want to avoid screwing up. Here are five uber-embarrassing things to never say:

  1. "F**k". Cussing just does not work when you are in your first set of meetings. Try it and then watch the look on their faces. Remember that investors are looking for reasons to say "no". They are imagining you sitting in front of a customer or a partner that they brought to the table. I cuss like a sailor--when I am in the drivers seat. You have not earned that privilege yet.
  1. "Would you sign my NDA?" This is a rookie mistake and screams amateur. Investors are in the investment business not the steal your idea business. Ideas are a dime a dozen. Professional investors get pitched hundreds of times a week/month/year. Imagine if they signed your NDA and then decided to pass on your idea because you are not ready. They would essentially lock themselves out of any broadly defined competing opportunity. In addition, they would have to manage all of the NDA's and their individual terms (1 year, 3 years, written obligations, etc.). What a nightmare.
  1. "Today, I am going to share my project with you." This is my personal pet peeve. I invest in companies not projects. Projects feel temporary--as if there is an anticipated end date. "Well once I turn my project in . . . ". Projects feel like they came out of an academic institution. These are flags that signal the investor that you don't know how this game is played. Pitch your business not your project.
  1. "My idea is Facebook but with . . . " Facebook is Facebook with fill-in-the-blank". You are not going to compete with Facebook or Google or Twitter. Your personable foibles with these platforms will not translate to a meaningful business. "My idea is to build Facebook but with a better user experience." "I am building an ad platform like Google but with better ad options." Really? Do you realize that these possibly incremental value changes are irrelevant to getting your company off the ground?
  1. Pitch a competing idea of a current investment. You have one chance to make a good first impression. My most embarrassing moment was pitching Brad Feld a mapping idea (post my MapQuest run) and 3 minutes in he asked me, "You know I invested in Vicinity" (a MQ competitor). I was speechless. I had found a top tier investor to hear my pitch and within minutes the conversation was derailed. The conversation ended about 5 minutes later. I had not done my homework.

Investors are like any other segment of the population. They have their own language, rules, idiosyncrasies and processes. Your job is to learn them before going in so you don't feel like you are in high school all over again.

Published on: Mar 19, 2015