A few summers ago, in Corfu on a hot August afternoon, in front of what once was Gianni Agnelli’s villa, I was observing two people in the sea. A man and a woman, having a lazy conversation, slowly floating in the water. He was telling her about a friend earning a living in a whole new way — driving an Uber. Back then, Uber was only known to the early adopter elite. The woman, clearly not a digital native, didn’t know what that was. So, the man said: “You know …. with your own car, over the internet”. She nodded in approval.

I was shocked by such a primitive way to talk about something so sophisticated, and so ingenious, and groundbreaking, and…revolutionary. I told the story to all my friends, at least I told them what I thought the story was: people on the other side of the digital divide, simply not understanding anything about the internet, and yet perfectly understanding each other.

But then I realized, I got it all wrong. In fact, the way Uber was explained was brilliant — the woman understood! A perfect pitch. And I bet she could also explain it to others. Every time I get into a situation to have to pitch a highly technical project to a non-technical investor, I remember this story and I really wish I could go back to that summer afternoon to apologize myself and thank the man.

I came to realize, through hundreds of pitches, that investors are a peculiar kind of animal. They worry about what the future will say, about being wrong (as most of the time, statistically, they are wrong), about appearing ridiculous in the face of failure, about potential future guilt, regret and remorse. Heavy stuff. Often, when an early-stage investor said “no” to me, it was because they found the project “too technical”. In other words, they didn’t understand it well enough.

So, I compel you to do the following thought experiment. Imagine that the investor you’re about to meet has a grandmother. After hearing your pitch, the following Sunday, the investor will go to have a family lunch at his grandmother’s. Now imagine the following, unavoidable, conversation.

Grandmother: So tell me everything, how is work? What is it actually that you do with those, …what-do-you-call-them …start-ups?

Your investor: Great! I am about to invest in one cool start-up that will become a giant company and earn us billions. They are making <your pitch here>.

Everybody wants to make their grandmother proud. And I have no doubt that, when the grandmothers of Uber investors take a ride, they are proud. That is where it really counts. On the emotional level.

I do have a sweet spot for metaphors, but this particular “grandmother” metaphor is one of my favourits. Just awesome for stress-testing your pitch, because it pushes the boundaries of clarity. Your investor must be able to remember your pitch well enough to repeat it and be convincing about the future of your company. Grandmothers are not as easy to sway with buzzwords. They lived through a lot and are less likely to be impressed with things they don’t understand. If your investor can pitch your startup to their grandmother, then be sure they can do the same with their colleagues, their investors etc.

If you can’t explain it simply, you don’t understand it well enough. ~Albert Einstein

It’s easy to self-asses whether your pitch is grandmother-proof. Ask yourself about the following real-life examples: “infrastructure-service for data minimization”, “yield optimization engine”, “screen-level encryption framework” …See?

To make my pitches grandmother-proof I often go back to the book Made to Stick that lays out a great framework to make your messages more sticky, simple and memorable. With practice, I hope one day I’ll be able to bring it down to “with your own car, over the internet”.

Questions for practice

  • Can I make my pitch shorter, more memorable and more relatable without losing the essence?
  • How can I test if my pitch is grandmother-proof?

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