7 Bad Pitch Personalities - Which One Are You?

October 14th, 2020

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By Chris Heivly, Techstars Senior Vice President for Ecosystem Development

Forgive me. I have listened to so many pitches over my years that I may have become a bit jaded. Well, maybe jaded may be too strong, what I really want to do is poke a little fun with the intent of using humor to make a very important point. Every one of us sometimes slips into one of these pitch personalities.

Your pitch presentation is often the first impression that an investor, partner, future employee gets of you and the business. Don’t screw it up!

Each of these “personalities” highlight an approach that creates a negative impression. So which one are you?

The Dreamer — The idea is so big and so perfect that no data is needed to support the thesis. Slides have big numbers and phrases that support megatrends. Finding any semblance of traction is fruitless. It's all fluff and no meat. There is no reason for any investor to follow up.

The Rookie — This pitch personality decides to change the basic pitch format that has been used for years (Hook-Problem-Solution-Traction-Market-Team-Ask, not in that particular order per se). Listeners are left wanting some answers and some idea of where this company is going, but the rookie wants to be unique and change the game. Bad idea.

The Charmer — The Charmer thinks, “I am great in front of people, I have the gift of gab, I can convince anyone of anything. No practice for me, I wing it all the time and have for years.” Problem is they miss critical things that need to be said and the pitch often ends up disjointed, especially when their pitch peers are doing much better and the Charmer realizes that their charm is not enough.

The Puppy — This pitch is super enthusiastic and the energy they create is palpable. You can't take your eyes off of them — which is great. They will usually say something like, “I am super passionate about this idea/concept/business/company.” But like the dreamer, they are short of data and real information.

The Trickster — Part rookie and part charmer, the trickster finds a few pitch tricks to get your attention: “Are you tired of being unhappy? Raise your hand if this is you!” But then what? Give the trickster credit, they have done their homework and developed a few key ways to grab you — but that is all they have in their bucket.

The Mensa — Super smart (just ask them), this superior being is going to convince you of the merit of their idea with data — lots of data. This is the intellectual pitch personality which attempts to use logic to show you why they see something special. Look for words, phrases, and lots of references to intellectual-oriented brands (Harvard, Brookings Institute, etc.).

The Hollywood — Very cool, smooth, and obviously been here before, the Hollywood could barely be bothered to pitch to this audience/judges/peers. It's as if they are here to bring importance to this event. For some, this might be their second startup or they may have already raised some money. Humility is in their rearview mirror. Their whole demeanor is Hollywood from their dress to their words.

Recognizing which category you fall into is the first step to redemption.

Want to avoid these personalities and the inherent mistakes that represent that? Follow the script, prepare like it's your last opportunity, do your homework, and let everyone know that you are lucky to be asked to pitch. Oh, and practice like 50x.

#Entrepreneurial Ecosystem

About the Author

Chris Heivly

Chris is one of the nation’s leading experts on launching startups and has been dubbed the “Startup Whisperer.”  He cofounded MapQuest, is an angel investor, ran a corporate venture fund and 2 micro venture funds (directed over $75M), and is SVP Ecosystem Development with Techstars. Chris recently published his first book about starting anything called Build The Fort and is currently writing a book on Startup Community Building.