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Through my time at the Bard Center for Entrepreneurship, Founder Institute and bumming around the Denver / Boulder Startup Community I have literally heard 1,000,000,000,000 (that’s a gizzilionbillion in case you were counting) pitches or maybe more. In a past life, I taught execs how to be better public speakers. I noticed a series of mistakes that many make while speaking. Couple that with the stress of a pitch competition and these simple mistakes become glaring… here are the 5 worst.
5) Alvin and The Chipmunks Syndrome-
Everyone gets nervous pitching their company. Even the most calloused entrepreneur can get a bit flustered when he stands up in front a room full of people about to judge him and his company. The problem is most people translate the hummingbird in the stomach into talking faster than a chipmunk on speed. Slow down! What you consider to be painfully slow is probably just right. Remember, you have enough adrenalin pumping through your body to kill a Water Buffalo. Silence is golden in pitches. It creates a sense of drama and anticipation. Use it!
4) The (Yawn) Professor Syndrome- I think everyone had that professor in college or grad school that was the world’s expert on ____________. You excitedly got to class early on the first day and sat in the second row (the first row is for brown-nosers) and prepared to be dazzled by his command of his subject. Reality set in when the bored professor wandered in 5 minutes late and droned on for 45 minutes talking in a language which may or may not have been English. You struggled through your semester and learned just enough to get a grade that your parents wouldn’t be too upset with and wandered on your way.
Your next class was taught by a young grad assistant who’s only expertise was racking up student loans. While not an expert, he was excited about the subject and excited about the ideas he was sharing. You probably learned a ton, aced his class and now can speak intelligently at dinner parties about _____________.
The universal truth here: people pay attention when the speaker is excited about their subject! I once was helping an executive with an important speech. He was one of the top 10 most boring people in the universe. Nice guy, just boring. After a week or so, we finally got him going by having him watch Billy Mays (the Sham Wow pitch man that died a few years back). Act like Billy was my simple advice. In his mind, he was acting embarrassingly crazy, to the rest of us the faintest glimmer of a personality was starting to appear.
The moral of the story… Act like Billy Mays. When you get to the point that you feel ridiculous, double your energy and you’re getting close.
3) The Data Dump-
You are the expert in your field. You have thought about, researched and just plainly know more about your market than just about anyone on the planet. During a pitch competition forget about all that knowledge (data) and tell a story and like all good stories focus on people. When you get into a private pitch with a VC or Angel they will want to digest every number you can serve them up, but not in a pitch competition.
The rule of thumb: do not focus on more than one or two data points in your presentation and make sure those are in support of a broader thesis. Pick the most compelling statistic and present it, be proud about it, refer to it but NEVER forget that you are telling a story. No one has ever told a good story about statistics. Except maybe Billy Mays.
2) Bad A/V-
A good friend was pitching at a very prestigious event when the pitch competition apocalypse happened. His presentation broke.
Now this is a smart guy. He tested his presentation countless times. He knew his talking points inside and out. He was well rehearsed but through no fault of his own, his presentation broke. My friend froze and in his panicked made a snarky comment about the young and cute volunteer running the projector. In a half a blink, the friendly room turned cold. He was suddenly pitching to 200+ East German judges. One person actually booed him… at a pitch competition.
The morals of the story: First, make sure your shit works. In my friends case, he got a bit too cutesy and added a video in to his presentation and that’s what broke. The show became more about his cutesy Powerpoint and less about him telling the story of his company. Second, when all hell breaks loose. Take a deep breath, let the silence linger (while the crowd holds it breath to see what is going to happen), make a joke and just keep going. Your powerpoint is just a visual aid to help emphasize your story. The judges an audience will appreciate your ability to adapt.
PS. Good friend did not die, neither did his company which is doing quite well.
1) Take Bad Advice-
This mistake is the most damaging. At the root of the problem is ego.
Conventional wisdom says seek the advice of expert presenters, listen intently to their feedback and try to incorporate their advice in to your pitch. The problem with this approach is that the people giving you feedback usually only know one way to pitch…their way. Their ego will not allow that their way (which may be awesome or awful) is simply one answer to a complex problem. Moreover, the person giving you advice probably has no idea what makes them a decent presenter (or even if they even are a decent presenter).
I once sat in a room and watched two very smart entrepreneur mentors, who were asked to give feedback on a pitch. They gave completely contradictory advice. To make matters worse, the two mentors, both with huge egos, ended up arguing with each other for 10 minutes about who’s advice was most sound, while the bewildered entrepreneur stood up in front of the room in utter awkwardness.
Pssst… here’s the secret… there is no one “right” way to pitch. After years of coaching awkward executives. I discovered the secret to improving their presentation skills. Don’t try to teach them the text book way to present, let them do it in their own style just make it bigger.
The truth is you probably already know what you need to do to give a great pitch but for whatever reason your middle school self chimes in and reminds you that it will be scary and that you need to get some good advice. You ask someone smart with a big ego and whamo, you’re stuck in the vortex of people giving you advice.
I still think getting feedback is a good idea but just like choosing fried chicken in a buffet line, keep the best pieces and toss back the rest.
That’s it that’s the list….Sorry for the long post.
Let me know your thoughts, did I miss any? Any good stories of pitch disasters?
Cheers,




