David, Goliath and the Investor Pitch

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At some point or other, we all find ourselves outside of our comfort zone, and even feeling like we are out of our league. Nowhere is this more prevalent than when pitching a business, product or idea, and the little voice inside our head says, “Am I good enough? Do I belong here? Will I meet their expectations? Can I persuade them?” Today I want to share with you how one person rose to the task and showed everyone that he deserved a seat at the table, and was playing to win.

A favorite part of my job is helping people tell their stories in a compelling way, and the business pitch is a high-stakes platform where you only have one chance to do it. I had the distinct honor and pleasure of coaching five Hero Club entrepreneurs in preparation for their pitch at the C-Suite Network Investors Summit in San Jose on September 11-12th. All five CEOs were terrific, but in retrospect, one pitch stood out from the rest, and offered a lesson about overcoming the odds and expectations, and why you should never underestimate anyone – including yourself.

David Williams is the CEO and superintendent of Village Tech Charter Schools in Cedar Hill, Texas, just outside of Dallas. More than one person I spoke to afterwards confirmed that they had wondered why a non-profit, specifically a Pre-K – 12 school, was pitching in Silicon Valley. Privately, they had wondered if it was something of a charity case, like when the older siblings decide to let the little one play with them, even though they have minimal expectations. David himself later confessed to having similar concerns leading up to the event.

David is not alone. How many times have you anticipated an event or opportunity with trepidation, based on feelings or concerns of inadequacy, of not belonging? Sometimes there’s a bit of the “Imposter Syndrome” that creeps in. David had to prove to himself and everyone else that he was a much of a leader in the business world as in the academic realm.

To David’s credit, he rose to meet this Goliath. He knew what was at stake, and his motivation was focusing on how important it was for his company, his school, his people and his community.

One of the most common areas where people tend to fall short is in being able to adjust your message so that the right points get across to the right audience: a critical factor in the art of persuasion. In this case, David’s challenge was making the shift from “teacher” mode to “business executive” mode.

His favorite stories of children’s heartwarming experiences and funny comments will successfully imply all sorts of information about the success of a program when speaking to a room full of teachers. But to a room of business executives and investors, those stories are just the sprinkles on the sundae: added for a little color and sweetness, but of minimal substance. We had to shift the focus to problems and solutions, to data and dollars – a philosophical shift that makes most teachers’ stomachs churn with disdain. And the whole thing had to be done in eight minutes.

We found ways to use a couple of anecdotes to personalize his statistics, and humanized the call to action, which helped him make this critical shift while remaining completely authentic, and true to himself.

Although many investors there weren’t interested in adding a brick-and-mortar enterprise to their portfolios, it was clear by the end that David’s pitch was the crowd favorite. The little non-profit venture had set the bar for what everyone else believed an investor pitch should look and sound like. He had succeeded in earning the personal and professional respect of everyone there, as evidenced by a comment I heard come from several people’s lips with genuine admiration that day: “He killed it.”

The moral of the story is not to let yourself be intimidated by your “Goliath.” Even when you feel like you’re out of your element – or even your league – seek whatever guidance you need, and play to win.


Are you preparing a pitch, or do you have questions about another critical presentation? If so, contact me at laura@laurasicola.com or click here to schedule a 20-minute focus call to discuss it with me personally!

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