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Pitching My Startup

What our writer learned about winning over investors.

Like most good stories, this one starts with a crazy idea. It was an idea for a business, and it struck me so thunderously one day that I couldn’t believe this product didn’t exist. I was going to be rich—as soon as I could get some startup capital.

So when I received a story assignment that would allow me to present my concept at Venture X Pitch Night in front of 100 business people, including investors, I was in. After all, how hard could it be? I’d once had a job that required me to give three sales presentations a day; a five-minute pitch would be child’s play. This moment was it, my big break. I researched, prepared a PowerPoint and practiced and practiced and practiced some more. Dozens of hours and about 18 trial outfits later, I was ready to shine.

But when the evening began, my optimism began to falter. The room went dark and I watched those before me stutter under the gaze of more than 200 eyes, the cruel comments from the Twitterverse (the event was live-tweeted) and the flashing bulbs of the local media’s cameras. Sweat began to bead on my forehead as I realized that soon I would be subjected to the same pressure.

Was it too late to bail on this whole idea?

A voice loudly announced: “Please welcome AC Shilton.”

Yup. Too late.

So, I took the mic and began my presentation, as I thought to myself: How will this all turn out?


Pitch Night was devised by David Diamond and his son, Brett Diamond, who describe themselves as “startup junkies.” The two own Venture X, which is a co-working space that they opened last fall at Mercato. David Diamond, who also is the founder and president of DeAngelis Diamond Construction Inc. in Naples, has been an angel investor for many tech startups, and Brett seems to be following in his footsteps. 

The two hope to foster a new generation of innovators in Southwest Florida, and they’re using events like last fall’s Startup Battle and this February’s Pitch Night to do it.

Diamond also says he believes in a “pay-it-forward” business philosophy. It’s something he has seen work in Silicon Valley, where highly successful innovators take time to mentor those just starting out.

When I initially saw Venture X’s call for submissions, I suggested to my editor that this would make a great story. He agreed, so I sent my idea in and crossed my fingers.

When Brett Diamond emailed me to let me know my pitch had been accepted (I was one of eight chosen from more than 40 applicants), his next sentence read: “When can you come in to meet with my dad?”

At that meeting, I quickly realized that I was starting way behind the curve. And here’s the first misconception I had: It’s not about vetting an idea; it’s about showcasing a business.

“Everyone in the room has an idea; that’s not what we’re looking for,” says Diamond, adding, “Investors are looking for businesses that already have key pieces in place.”

Diamond spent the better part of an hour pelting me with several dos and don’ts for pitching. “Do have a PowerPoint prepared, but don’t you dare rely on bullet points. Do stop and take questions from potential investors, even if it eats into your time. Don’t ever interrupt anyone who might hand you a fat stack of cash.” The list wound on and on.

On the drive back to my office I contemplated calling my editor and killing this story—the whole thing just seemed so overwhelming. But the next day I reluctantly plunked myself in front of my computer and opened up PowerPoint.


My business idea, in a nutshell, was this: I wanted to create a journalist-owned and -operated media company that would help retirees capture their life stories through audio recordings.

For my presentation, Diamond had told me to include something memorable and to start off by creating a need. Invoking my grandfather—a man of many amazing stories, none of which any of us thought to write down before he passed away—seemed as good a place to start as any. Besides, who could hate a girl who led off her presentation with a photo of her kindly old “Papa”?

Diamond says he’s seen many people who are naturally good public speakers flail during a pitch because they didn’t rehearse enough. With only five minutes to present, every word matters.

And so I stood in my living room and explained my business over and over again to my dog. She seemed unimpressed. In the end, however, I figured if the looks I got on Pitch Night were half as blank as the ones my mutt was giving me, I’d be in good shape


It’s 5:30 p.m. and the crowd gathering in Venture X’s ultra-hip lobby is concerning. With another hour to go before the night starts, Brett Diamond says he’s expecting close to 100 guests.

David Diamond pulls the presenters into a conference room for a last-minute briefing. Instinctually, we all size each other up. We’re not technically competing, but, well, we are. Our businesses are different, but the resources available from the audience only run so deep.

Between presentations, there’s chatter about the best time slot in the lineup. One swears being first is best, another suggests last is the sweet spot. I’m slated to go in the middle. The seasoned pitchers (and there’s a whole circuit of pitching opportunities around the state and the country) advise me that I’ll have to do something to make myself memorable.

Something like pass out? That’s beginning to feel like a real possibility.

The room goes dark and the first presenter begins.

On cue, I feel sweat beads forming under my arms. (Why, oh why did I wear a light-colored cotton shirt?)

And then it’s my turn. I open the first slide, stutter for a second and then see the photo of my grandfather. Somehow it makes me feel better, and I dive into my presentation.

Slide by slide I make sure I cover my bases. I highlight a need, fill the need, explain how revenue would be produced, show scalability and honestly lay out all of my potential competitors, which is a good idea, according to Diamond.

“The worst thing is when someone says they have no competition and someone else in the audience says, ‘Well, actually you do.’ It really shows that they haven’t done their research,” he says.

If research is the number one thing to do before you pitch, number two is preparation, as one presenter learned. “I’m the kind of guy who likes to do things without practice, and I’ve realized that that is kind of a character flaw,” say Kevin Barnhill, who pitched his smart doorbell company, called Chime.


I can tell you surprisingly little about my actual presentation, other than I did not receive any questions (they came after the program). The time slid by so quickly.

At the end, as I see Diamond approaching to take the mic away, I ask, “Am I done?” with the same inflection as a toddler asking if she’s completed all five minutes of her timeout.

But here’s what I can tell you: Before you pitch, have as many of your ducks lined up in a row as possible.

Tim Cartwright, president of the Gulf Coast Venture Forum and chairman of the Tamiami Angel Fund, whom I spoke with ahead of the event, says that groups like his don’t want to hear your pitch unless you’re elbow deep in your project.

“The one thing I don’t think people that come and pitch in front of our group walk away with is a check,” says Cartwright, who also is a partner with Fifth Avenue Advisors in Naples. “The best thing they can walk away with are the names and telephone numbers of anyone who was interested in their pitch.”

Diamond and Cartwright both emphasize that regardless of the post-pitch chats with guests, what happens in follow-up conversations is probably far more valuable in the long term.

Which is illustrated perfectly by my dumbest mistake of the night: In the hour following my presentation, I realize I’ve forgotten to bring business cards. Close to a dozen people want more information and here I am, scribbling down my contact information by hand. But I also realize something else: My product resonated with women. Of the 12 or so people who approached me, 11 were women. Now I know whom to target.

My final takeaway is that once you pitch, you need to be ready to move on developing your product.

As potential contact after potential contact handed me their card and told me, “We should do lunch,” I realized, ready or not, my baby business was growing up.

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