Converting a (meh) pitch into an (engaging) story

If there is one common thread I see on first-time (even second-time) entrepreneurs, they get too excited about their idea, know too much about it, and tell an incomplete or confusing story about what they are doing and why.

They might give you too much detail of their product’s intricacies or assume you know the jargon of the industry they are in. It’s fine if you are just telling a friend, but it’s not OK when you are pitching investors, partners, or candidates.

The one book I recommend to all entrepreneurs is Made to Stick. It’s an easy read, and it talks about why some stories (ideas) stick and others don’t base on a whole lot of behavior science.

At a practical level, I compiled this list of tactical things you can do to make your pitch (slide, press release, sales call, investor call, etc.) more compelling.

#1 — Humanize your story

Numbers, stats, and general data are boring. Very boring. Try to get rid of all the “there are 73M people who make less than $75K a year and spend $377 on average on …”. It’s better to say something like, “… one of our customers is a mother of two who is living on a single salary and her…”

Even if you are not building a consumer product, you still can humanize the story by telling the story of the person inside of your customer who will be using your product and why her life will be better, how she’ll be able to make faster and more accurate decisions, and make or save more money for the company.

#2 — Don’t mention unrelated companies or people

There is the analogy way of mentioning a company (“We are the YouTube for…”), which I think is fine. It’s pattern matching, and our brain has been designed for it. The mentioning I find useless is when you try to show how Amazon was successful doing X, and you’ll do X, or how Steve Jobs was quoted saying Y, and it’s something you believe in. Honestly, that’s 100% noise. No investor will look at this and think you are into something.

The easiest way to test if you are doing this is if some other startup can reuse your slide or the same paragraph in their pitch and makes sense. If that’s the case, you are not telling your story. You are telling someone else’s story.

#3 — Prime the listener

Priming in psychology means that you create a specific stimulus to affect the response to a follow-on stimulus. In practical terms, listeners might receive your story differently depending on how they are thinking about you. Duh!

Let me give you a more clear example. You start telling your pitch, assuming the person knows what industry you are trying to disrupt. Half-way through the story, they turn to you and ask, “Oh, so you are a smart calendaring service for home contractors?” And you say “yes.” The listener might have lost everything in your story up to that point because she was spending her cognitive processing power trying to figure out what the heck is this thing. If you started your story with “We are building a smart calendaring service for home contractors, let me tell you more about it,” you primed her to the story to follow. She will have a different lens, and she’ll be better positioning to receive your message.

Prime can be many things. It can be you. If you have a Ph.D. in Economics from the University of Chicago, and your product will benefit from your expertise, you might start your pitch with that fact.

#4 — Checklist your pitch

If you are giving a 5-minute pitch on demo day or to a single investor, you must make sure you cover your bases. It’s too easy to know too much, forget to mention something, and expect people to connect the dots. Looking from the listener point-of-view, these are the questions they should be able to answer after they listened to you speak:

  • What problem is being solved, and for whom?
  • How are you going to find customers and convert them?
  • How are you going to make money?
  • How big is this opportunity?
  • How much risk have you eliminated so far? In other words, how much progress have you made?
  • Who are you, and who’s on your team?
  • Why should I care and invest, partner, or join your startup?
  • Bonus: Why has no one done this before? What makes this hard or the time right?

#5 — The Curse of Knowledge

I mentioned this a couple of times above, but the Curse of Knowledge is the Achilles heel of pitching and presenting. We get so embedded in our view of the world that we forget people might not be on the same page. It would be best if you practice your story with people that never heard it before.

I have a litmus test to see if the story is flowing correctly, i.e., if I’m using too much insider information or jargon. The test goes like this: If you say something, and the following question feels like “what?” you have to change your story. If the follow-on question feels like “how?” you are on the right track.

If you tell me a tagline, and I ask you, “what do you mean?”, you missed an opportunity, but if I ask you “how do you do it?”, it means I understood what you are creating, and I’m curious to know more. You don’t want at any point to hear “what.” At each point, you want the feeling of “how?” coming. How are you going to build the product? How are you going to hire a team? How are you going to acquire customers? Are all good questions. What business are you in? What customer are you trying to serve? What’s your revenue strategy? Are all indication that you missed something on your pitch.

#6 — Clean and crisp slides

There is so much written about how to create great presentations. Sadly, most entrepreneurs don’t read those books. A few things for you to keep in mind:

  • Copy edit your slides: Once finished with your first pass, go back and cut 50% of the words and numbers. Then go back again, and cut another 50%. Now you are closer to where you should be.
  • Big fonts, big images. You don’t know how far people might be from the projector or screen, and using small fonts, images where the information you want to convey is in a detail, or screen captures that make it hard to read will not do you any good.
  • There is a story arc that starts on the first slide and ends at the last. You want to close that arc, but then you have a micro-arc at the beginning of each slide that you want to close at the end of that slide. In other words, on slide one, you want to move listeners from point A to B. On slide two, you want to move them from B to point C, and so on.

This post is far from a complete guide on creating astonishing pitches and presentations, and if everyone followed the same pattern, it would also make it harder for you to distinguish yourself. Be creative, show that you are resourceful, and have a very crisp explanation of your product and business.

Follow me on Twitter @calbucci.

Marcelo Calbucci

Marcelo Calbucci

I'm a technologist, founder, geek, author, and a runner.