David, Goliath, and the Investor Pitch

David, Goliath, and the Investor Pitch 150 150 Laura Sicola

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. It was an exciting event and helping people with great ideas, products, and services tell their stories in a compelling way is one of my favorite parts of the job.

All five CEOs were terrific, poised and articulate with a solid pitch and great visuals, and they all reported being approached afterward by interested parties; what more could we ask for? But in retrospect, one pitch stood out uniquely, and offers 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. Various people I spoke to after the fact confirmed that, before his presentation, there had been a general wondering about why a non-profit, specifically a Pre-K – 12 school, was pitching in Silicon Valley. At best, most admitted preliminary assumptions of it being something of a charity case, like when the older kids let the little one play with them, even though they know he’s not in the same league. There seemed to have been minimal expectations for his performance. Perhaps not so surprising was the fact that David himself later confessed to having similar concerns leading up to the event.

David may not be 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 when surrounded by other highly expert, highly experienced, and/or highly reputed people. It might also occur if you’re just generally not comfortable presenting to large groups, if the event is particularly high-stakes, or if it’s your first time in the spotlight in a new context such as a conference presentation, in the media, or in this case, an investor pitch. The enormity of the pressure to perform and succeed in the public eye is enough to make most people’s hands shake – even if only a little.

But to David’s credit, he rose to the occasion and proved that he was not going to let this Goliath of an event get the best of him. He knew what was at stake, and he knew how much he wanted it for his company, his school, his teachers and his students, and that was the motivation he used to prepare for it.

The biggest challenge was the need to shift from “teacher” mode to “business executive” mode. Knowing your audience and figuring out how to angle your point so that it speaks to their unique perspectives and interests is a critical factor in the art of persuasion, and one of the most common areas where people fall short.

When speaking to an audience of teachers and school district members – his comfort zone – stories of children’s experiences and anecdotes of their funny and heartwarming comments will successfully convey all sorts of implicit information about the success of a program. 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.

To me, the key to his success was the fact that he was able to adapt his content to meet the needs and expectations of his audience, while still remaining completely authentic, and true to himself, both in preparation and on stage. This is often one of the greatest challenges we face when we find ourselves in new contexts with unfamiliar audiences.

I know inside he didn’t like having to cut out some of his favorite stories, but we found a way to use a couple of them in ways that made statistics personal, and humanized the call to action. And David was already a confident and competent public speaker, so it was really a matter of applying those skills with a different focus, and convincing himself and others that he was a much of a leader in the business world as in the academic sphere.

Sure, there were investors there who weren’t interested in adding a brick-and-mortar enterprise to their portfolios. But it was clear by the end that he was the crowd favorite and had earned the personal and professional respect of everyone there. The little non-profit venture had set the bar for what everyone else believed an investor pitch should look and sound like. As I heard several people say with genuine admiration that day: “He killed it.”

The moral of the story is that even when you feel like you’re out of your element – or even out of your league – do not let yourself be intimidated by the Goliath. Seek whatever guidance you need to put the pieces together, and play to win.


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


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