10 Ways a Good Pitch Feels Awkward...At First
Sometimes Doing What Feels Wrong is Dead Right. Here are 10 of Those Times.
When you’re snowmobiling in deep powder, and want to turn right, you have to turn the skids left while you brap the throttle and lean the whole 500-pound machine on its right side. For a beginner like me, It’s almost impossible to convince your body to turn the handlebars toward the big scary slope in order to steer away from it.
When you learn to box, you have to keep your elbows down by your sides, you tuck your chin, and your left shoulder hunches up to your ear. It feels nearly as awkward as getting punched in the face.
If you’re piloting a jet boat up a river at 30 miles per hour, the jet doesn’t act like a rudder (like on a prop boat), so your ability to steer is proportional to the amount of thrust. You have to steer with the throttle. Plus, if you go slow, you’ll sit lower in the water and hit rocks deep beneath the surface. So if you do what any sane person would do and throttle down to avoid an obstacle, you’re more likely to hit it and hit it hard.
Most of life is like that.
Maybe wildebeests can just do what feels right, but for humans, we have to constantly contort our minds and bodies into awkward, unnatural positions in order to learn to bike, swim, play the violin, type on keyboards, code websites, and impress our friends at the skate park.
The upshot is that we don’t have to drink nose-down at the water hole, and far fewer of us get eaten by crocodiles.
Which brings me to pitching.
Every entrepreneur already knows how to pitch. Just like they know marketing. You just trust your intuition and let’er rip. Just turn the handlebars in the direction you want to go. Just belly up to the water's edge and take a sip.
What could go wrong?
But go take a look at those pictures of your first birthday. Not even cake eating is a skill you were born with, and if you really want to excel on the pitch, then you have to train your mind and your mouth to think and say things that don’t come naturally.
Here’s ten pitching skills that monkey with our intuition. Just settle in because things are about to get awkward:
10. Prepare to Sound Natural
The best way to sound natural is to make your pitch impromptu. Off the cuff. Unrehearsed. Back of the napkin.
Nope. Save the napkins.
If you don’t rehearse your pitch at all, you’ll probably sound like you were scripted. But scripted by a clueless consultant giving you instructions over a bad cell connection. If you script your pitch word for word, you’ll also sound scripted, but this time by the generic, monotonous ChatGPT version of yourself.
If you really want to sound natural, then you have to put in reps of your pitch (to the bathroom mirror, to the dog, to your kids, to strangers on the subway) until you’re not fumbling through memory to find the details - until you can riff and improv with ease, until it’s harder to mess up than nail it. Guy Kawasaki recommends 25 reps in The Art of the Start. The best actors act their best when they aren’t struggling to remember their lines.
9. New To You
Pitching can be boring…for you. Because you’ve pitched the same thing in the same way 60 times this week. You start to feel like you need to spice things up.
Resist!
You’ll probably just wander off into some pointless backwater and leave the key things unsaid.
My pitch is old to me but it’s new to you. The trick is remembering the magic moment three years ago when the great idea you’re pitching now exploded onto your prefrontal cortex, for a moment displacing the orbit of all other thoughts in your galaxy. Hold on to that feeling! You can make others feel the same way, but not if you branch off-topic just because the fuzzy feeling has been worn smooth for you.
8. Saying What the Slides Are Not
Your audience can read. They can read silently faster than you can read out loud. So for the love of lava lamps and dogs in the office, don’t read your slides. Just because the text is on the slide doesn’t mean you have to say it out loud.
That’s why the text is there! So you don’t have to say it!
Just don’t.
Instead, say something that provides context for the text or the images or provides a corollary to the narrative.
7. Not Saying Everything
Hmmm. What do I want an investor to understand?
Oh, everything. That’s right! So I better highlight everything.
But if you highlight everything, then nothing is highlighted. Ten bands playing at once is not music; it’s noise.
So if everything in your pitch is bright red and ALL CAPS and bold and you try to hammer home 10 key points on each slide, then your pitch devolves into static - just a faintly-irritating, crackling whine in the back of your audience’s brain.
You’re not going to be able to communicate everything. Get over it. Even if you could communicate everything, it’s not going to happen all at once. Leastways, it’s not going to happen on this slide.
Instead, break your idea apart and focus on one bite-sized morsel at a time. Connect the breadcrumbs together in a tantalizing sequence, and eventually, your audience may consume the whole loaf.
6. Start at Interesting
Like Putin in the Tucker interview, many entrepreneurs feel the need to start with what came first. Back when half of what is now Russia was ruled by Ghengis Khan.
It’ll work just as well for you as it did Putin.
Go watch the movie Memento, a riveting whodunit that unfolds in reverse chronological order. Why do you put up with such a convoluted story sequence? Because it’s interesting. Because every scene is interesting. Especially the starting scene.
So that’s where you should start too. Start with the most riveting detail about your story, your product, and your market and bridge from there into the rest of the pitch. When you first start pitching, the most important factor is the audience’s motivation to keep listening and interesting beats first every time.
5. Undersell…A Little
It’s hard to get people’s attention so our tendency is to dress up our experience, our sales, and our tech at the outset so there’s no possible way that our audience won’t be disappointed by the end of the pitch.
You do have to get people’s attention, but starting at 11 means that even if you’re a 9, investors will feel let down, maybe even deceived.
Instead, start a wee little bit below the expectation you know you can exceed as you disclose more information and gradually step up the scale. The investor’s emotional journey from good to better will feel more satisfying than a journey from great to good.
4. A Hot Data
For some reason, people act like data is naturally sexy. It’s not. Or that their audience is Data - a pale robotic calculator of a human. He’s not.
The data says 3,000 people are killed by distracted driving in the US every year, and I bet the investor you’re pitching was still texting at stop lights on his way to work this morning.
Data is only convincing if it’s in a context where you can emotionally connect with it - If it’s part of a story you’re a part of. Likewise, even the most Data-like investor isn’t going to pull out his wallet just because all the numbers add up. He’s waiting until he feels that special something deep in his squishy human heart that provides the motivation to do math in his cold hard android head.
Maybe it’s the account of why one of your thousand customers chose you, or maybe it’s getting into a fender bender on Sand Hill Road. Either way, data doesn’t have a pulse unless it’s placed inside a story.
3. Highlight your Failures
You’re not fooling anyone. You’ve got competitors, your experience is spotty, your product’s not ready for prime time, and all the marketing you’ve done is that one run of Facebook ads.
So own the suck. Admit your failings. At least some of them.
If you can own up to your shortcomings, then your audience will give you credit for other qualities. You may be young, but you’re smart, your early adopters love you enough to put up with imperfections, If you’ve made $20k on a few ads, then what if you could hire someone who knew what she was doing?
2. Asking for Money
If you feel natural asking for money, then your trust-fund-baby childhood must have caused psychological damage. Most of us feel as comfortable asking for money as guys discussing menstrual health. Sometimes even experienced entrepreneurs blush and break down when it comes time to make the big ask.
But money’s probably why you’re pitching, so it’s part of the deal. It sort of is the deal if there’s a deal to be made.
The trick to making “The Money Talk” less cringy is to equate money with acceleration. Acceleration not movement. If you don’t get the money, that shouldn’t mean you stop or (worse) that you don’t start. Money should make the rocket ship go faster, but the launch should be inevitable. If the idea of more money is connected to all the ways it’s going to help you grow faster, then the money talk is fun not awkward.
1. Shutting Up
To pitch you have to pitch. But the most important and least intuitive part of pitching is learning when to stop pitching. When to shut up.
People usually don’t shut up soon enough because they want to be extra-especially sure that the message got through. So they circle the wagons, beat the dead horse, and whistle into the wind in hopes one of those metaphors isn’t accurate.
But the regurgitation of what you just said isn’t usually as interesting or appetizing as when it was fresh. Plus, you start to sound like you really really really need your audience to believe what you’re telling them please!!! . . . which of course makes your audience feel like you’re desperate or lying or both.
So say what you need to say and no more. And then stop. Really. No really, you should stop now.
Ok, stopping.
Oh, but I…
Nope. Just shut up.