3 Mistakes That’ll Kill Your Pitch

Actually, 4 mistakes, I included a bonus one ;)

Oussama Ammar
Jan 13 · 6 min read
I spent a whole event talking about this stuff, if you’ve got the time ;)

In American schools, there’s a fascinating thing that kids do: Show & Tell.

For all of you Europeans who don’t know it, it’s simple. Kids bring in an object, just a normal object from their home, and tell the class why it’s important and special to them. So you see these kids, 5 years old, telling stories that turn everyday objects into something interesting, something people enjoy hearing about.

Obviously not everyone’s great at it. But the ones that are, they’ve started pitching early, and they’ll keep building their skills up over the years. The ones who are really good at it might even grow up to be entrepreneurs, benefiting from starting to pitch really early, even with something as simple as Show & Tell.

For those of us who didn’t go to school in the US though, we’ve gotta start learning when we’re a bit older. There are a ton of different ways to pitch the same company (and you need to learn quite a few of them). But because there are so many ways to do it, it’s useful to go through a few things that you should absolutely avoid while developing and delivering your startup pitch.

1) Don’t force the same pitch on different audiences

It’s the big rule in pitching: Know your audience. One of the worst pieces of advice you can get is that a pitch should be understood by everyone who hears it. Sure, at Show & Tell kids are telling simple stories, because they’re kids. As we grow up, things change. Why would you need a pitch that’s so simple a 5-year-old can understand it? 5-year-olds don’t have any money, they can’t buy your product! Plus, they’re 5, they’re pretty limited in what they can understand. If you’re selling a cloud security solution for the enterprise market, it’s pretty useless to have a pitch that a 5-year-old can understand.

After all, your target audience isn’t “Everyone.” If you say, “Oh, but my solution is great for everybody, how can I decide who to focus on?”, my response is gonna be, “No, it’s not; making that decision correctly is what you have to do to deserve your equity.” Don’t be afraid — if you choose the wrong audience, that’s ok, you can change it and try again.

Then always understand who you’re talking to. Ask questions and pay attention to the answers. Every good pitch starts with a deep understanding of your audience, because that’s what lets you talk to them in a way that touches them. It’s all about empathy, and having empathy is critical for an entrepreneur.

The people listening to you are real — pay attention to them.

Getting comfortable with pitching is about feeling good with people one-on-one, and then moving up to a small group, then moving up again, until you’re comfortable with lots of people and lots of situations. Keep adapting, let yourself adjust to the people in front of you.

It’s not easy, I see that all the time with entrepreneurs at The Family. We get a lot of entrepreneurs who are naturally pretty good at pitching, they know what they’re doing, they talk about their startup well. But then at a Family dinner I’ll say to them, “Hey, there’s that investor I told you about, go pitch them.” All of a sudden, the entrepreneur who was so clear and sure of what their company is all about is talking like they’re writing for McKinsey: “Did you know that in 2020 over 7 billion people will blahblahblah…” And I’m watching them, thinking, “What happened?”

Adapt your pitch for your audience, but treat people as your equals — remember that everyone that you pitch is just another person.

2) Don’t forget your fairy tales

Think about the fairy tale. They always follow the same narrative structure: A long time ago, in a galaxy far away, someone did something. Then we meet our hero, who now faces a problem. The hero struggles, there are lots of obstacles. Then the hero overcomes those obstacles, solves the problem, and we have a conclusion.

For thousands of years, across all kinds of cultures, we’ve had that narrative structure. Why? Because it works. 99% of us have been exposed to that structure from our earliest childhood. And it’s a structure that essentially follows how our brain processes information. We digest that kind of story very quickly, which makes us like it. And so fairy tale pitches in startups are also super powerful.

Thinking about fairy tales is important because, practically speaking, what’s a good pitch? It’s a good story that people can remember, a story that includes enough information to keep people interested. You don’t want to give too little detail, you don’t want to give too much detail — you need to Goldilocks it and find that perfect amount. It’s not about telling everything all at once; it’s about crafting a good story that makes people want to know more.

That’s also why you can never give any one fact or detail the opportunity to kill a good story. Obviously life is more complicated than a good story, but pitching isn’t about explaining everything. It’s about finding the right story to market your startup.

3) Remember that the world’s a stage

Once you understand that structure and you see how it can apply to your startup, you can make it become natural. Why are so many people bad actors? Because they get up on stage and try to put too much drama into their presentation. The great actors are the ones who are completely natural, the ones who aren’t just repeating lines and expressing emotion. Great entrepreneurs are the same way, they embody the story.

The goal isn’t the perfect pitch, it’s the one that you really live. You want to practice and refine your pitch every day, not just memorize it. Live your pitch, try different bits, see what works and then push further. It’s like a comedian, they don’t write an entire Netflix special and go up on stage. They work in small clubs, they test jokes, they change them, they adjust. Entrepreneurs should do the same thing. Try a new sentence or story on an employee, see if it works. If yes, try it at a dinner with someone you don’t know. If that works, try it on a bigger audience, etc. Work your way up, and you’ll have a natural pitch that you’ve practiced without ever having it be artificial.

This isn’t just important for your pitch. If you try to memorize your pitch, the perfect way of talking about your company, it’s the best way to get so completely bored that you just want to quit your startup. You’ll be so tired of saying the same sentence in the same way that you won’t be able to take it anymore. Repetition, experiencing the same thing over and over, it’s one of the best ways to feel disgust.

So keep finding new angles, find new stories, take risks. You’ll have some that are total catastrophes, that’s ok. If you screw up one pitch, it’s not a big deal. Just try to always be as specific and clear as possible, it’ll be fine.

Bonus! Never use a pitch deck while pitching

Decks are meant to be sent as an email, not used in person. Don’t put anything between you and your audience — and that’s exactly what happens if you use a deck to pitch. Decks are there to convince people either before or after a pitch, not during. Go ahead, name a great presentation you’ve seen with someone going through a pitch deck. It just doesn’t exist.*

*Steve Jobs didn’t use a pitch deck. He used images that changed as he spoke. That’s a show, it’s next-level. It’s definitely not using a pitch deck.

Pitch Don’t Kill My Vibe

The best open mic for entrepreneurs in Europe! Discover new startups & learn how to pitch better than anyone! Website: www.pitch.thefamily.co

Oussama Ammar

Written by

Co-Founder & Partner @_TheFamily - Brain (& Meat) Lover

Pitch Don’t Kill My Vibe

The best open mic for entrepreneurs in Europe! Discover new startups & learn how to pitch better than anyone! Website: www.pitch.thefamily.co

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade