Pitch-Perfect: How to Convince Someone Your Startup is Worth Investing In

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I had the pleasure of being a fly-on-the-wall during a series of investment pitches recently. The night before, and continuing into the morning of the Awards, young companies from all over the island had the ears of a very distinguished group of investor big-wigs. Mad Ventures was there, as well as Toronto’s Espresso Capital. All of them (around a dozen at any given time) seeking major talent to add to their portfolios.

All-in-all, I witnessed somewhere around 30 pitches at VIATEC in BC.

On Friday morning, with breakfast (as a meal, not a person) the pitches included the charismatic Marc Stoiber as a spectator. Stoiber runs a company that teaches companies how to pitch, or how to improve their pitch; Your Perfect Pitch (no, not the name of a sequel in the popular movie franchise).

I thought it would be useful to gather intelligence on what makes a good pitch, and what can sink it.
Through all the pitches I paid witness to, one thing came up at the end of every single one of them: the lead-in. Each talk, each company, has a few major points of interest, especially when considering what an investor might find particularly interesting. Most of the scripts written, and read in front of the crowd played out like a film, or a panel, where the biggest drops were near the end of the pitch.

It was suggested, in order to acquire the attention of the room—especially when you’re in a room filled with people of whom you desire their financial support—to do a better job of hooking with impressive slides right off the bat. You don’t have to blow through every slugger you’ve got in your arsenal from the get-go, but take your top few slides, and move them to the front of your presentation.

“Hook me, right away,” says the CEO of Espresso Capital, Alkarim Jivraj.

Truth is, there’s a lot to be said about coming through the gate hot. Short pitch sessions are growing rarer as I gather more experience sitting in on them, and playing the majority of your cards at the start will allow two things to happen.

First, those interested in what you’ve got to say will provide you with their undivided attention, making the rest of what you say just candy for your sundae. Second, those whom you would have lost near the end of your spiel will be able to regain the short amount of their time you would have wasted. And I don’t know if you’re aware, but important people can usually use some extra downtime to read emails, respond to texts, Facetime their families, or just Snapchat the buffet of bite-sized edibles.

The next big point of contention with the presentations from VIATEC’s lovely gathering was similar to the first; a lot of these companies—bootstrapping and fierce—shared a slide that bragged about their short-listed team names. Each time this happened (and I was surprised at the consistency of this) at least one of those listed was a heavy-hitting member of their sectors royalty.

But again, these interesting facts were blown over faster than the dump-bin filled with DVDs near the cash register at Best Buy.

“Wait, you’ve got to tell me how you got What’s-Their-Name on your advisory board?” is the question that always immediately followed the slideshows.

Much like the humble bragging used with pushing your fancy factors to the beginning of your talk, things like how you got Influential Member #1 on your roster isn’t something that you should just glaze over. No matter how many times it happened, and how many occurrences of the same question was asked, it was always followed with a great story that did far more good for the image of the startup pledging than damage.

Tell the stories. Make sure you explain how it is you garnered the interest of the big names you claim to have as part of your family. Don’t expect those listening to your pitch to put pieces that are unknown to them together without background context.

Lastly, I want to touch on competition.

In a world where your idea probably isn’t a new idea, and where your tech probably isn’t one-of-a-kind, don’t neglect to inform your constituents about possible competition.

“Who’s your main competitor?” Pitchers were asked nearly every time, or “What about competitor X?”

Strangely and more often than not, this question was responded to by brushing it off.

“I don’t feel like they’re our competitors,” or worse yet, “We don’t have any competitors.”

What. A. Mistake.

It is in your best interest to spend a large amount of time researching competition, potential competition, and anyone else that may show up at the same venues you do. The least attractive pitch is one that seems to feel like it’s the biggest of the next-best-things.

Spoiler alert: Everyone asking a group of people to invest in their idea thinks said idea is the best thing since sliced bread (obviously scones are the best thing since sliced bread, but that’s just my opinion). It’s important to anticipate that question, and answer it during your slides instead.

These are just some of the most obvious things I observed during many, many delicious hours of pitches. Simple concepts that will greatly improve the presentations of those hunting for investments.

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