Master the subtle art of pitching perfect

April 4, 2019 | Moonshot

Originally published on

To pitch is to convince, compel, to persuade and sway. It’s a subtle art and one that needs to be mastered if we hope to close an investment round, secure the needed support, or convince whichever audience of whatever worthiness. Moonshot has worked with hundreds of companies to craft convincing pitches, whether it’s for the big stage or the boardroom, and we put together

this list of “truths” for creating stand out pitches that win your audience. It starts with the game plan.

I. Define your play-by-play objectives

Clearly understand and articulate your end goal and then break it down into the play-by-play of getting there. Understand success at each step or each contingency, not simply the end game. You don’t get $10M out of one meeting. And if you do, congratulations, you definitely don’t need to read this article. Getting $10M starts with one meeting, the goal of which is to get to the next meeting to get to the due diligence to get that lead investor closed so you can get to doubling down on all your other prospects who are thrilled to come together and close your round. Framing up the succession of wins that get you to $10 million helps you determine what you present, to whom, and when exactly.

Too many founders are ready to shove the whole burrito down the throats of potential investors in the first email or meeting. One deck does not serve all. You need to send the right version at the right time to the right people. In the first outreach, send just what will create the intrigue you need to get a response. Don’t be overly mysterious but don’t let all your cards show either. The goal is to get in front of the investors or decision-makers first. You don’t do that with 60 slides and an appendix.

Pitching is a subtle art — know your goals and tailor content accordingly. The Cheshire Cat perhaps said it best in that, the way you ought to go depends a good deal on where you want to get to.

II. Do your homework on them

Figure out and communicate why XYZ investor/ supporter/ benefactor matters to you. Why do you want them specifically? Why should they, as smart, successful, busy individuals, give their attention to you? If you don’t have a direct connection or a warm intro, it is essential to do your research. In a cold email or call, demonstrate that you know who they are, what they value, how they invest, who they work with — something that shows you can see them for who they really are and you’ve done some homework. This

immediately sets you apart from the spam, canned email, and the lazier unimaginative people who cram the inboxes of investors with the next greatest idea ever.

With those prerequisites out of the way, you can then really start crafting your pitch — the one you’ll use once you’ve got their attention.


III. Be unique, not a template

Don Draper said, “you can’t stand out if you look like everyone else.” Don’t settle for the traditional template. You might be one in a thousand pitches that investor sees each year. There is a standard template approach and trust us, nobody sees it more times than they do. So if you want to cultivate glazed eyes and disinterest, follow suit with the status quo.

Successful companies have a product (something you sell), a market (someone who buys), and a team to orchestrate that opportunity. Investors are obviously looking at these criteria, but they’re also looking for a story. How

you present your story — something they can engage with, something that emotionally moves them in some way — is how you can hook investors into the mission, and the round.

IV. Start by distilling the essentials

Not all templates are bad though and a famously successful one is AirBnB’s first pitch deck. It’s an awesome specimen of brevity and business positioning. Nine content slides! Instead of trying to duplicate AirBnB’s deck though, break down the constituent parts to distill the essential questions you need to answer for your own company. AirBnb covered the baseline material so clearly, concisely, and successfully that the exercise is absolutely worth doing on your own to lay out key pieces that you can then weave into your own story.

Those essentials are:

1. Problem: clearly define it in one strong statement.
2. Solution: clearly articulate it in one strong statement and ensure that it’s

related to the problem in the most poignant angle possible.
3. Market validation: what is the most impressive (and accurate) way of

demonstrating the opportunity you have in your market.
4. Market size: what numbers best show the size of the pie.
5. Product: articulate the simplest, clearest ABC of your product.
6. Business model: in one sentence, how are you going to make money. 7. Market adoption: in a few bullet points, how you will find your

8. Competition: who are the top players you’re up against? Plot them on

an XY graph with variables that demonstrate the industry ecosystem
9. Competitive advantage: 4–8 bullet points on what really gives you your


V. Craft a compelling narrative

Once you’ve distilled the raw ingredients you can weave them into a potent narrative. A strong story takes the audience on a journey. There are highs and lows, places of tension, suspension, and ultimately closure that drives the

underlying moral or meaning home. Find areas in your story where you can create a little less linearity, more intrigue, and a bit of drama.

This can also be correlated to neuroscience and the attention of your audience. At the start of your pitch, before an investor hears anything, they’re likely dreams of ways of giving you all the money you’re about to ask for. No, they’re more likely in a state of healthy skepticism mixed with some impatience, complacence, distraction, and don’t ever underestimate hunger as a real-time factor. They’re likely comfortably situated in their “croc brains” — our animal brains that have developed over millennia in the domain of survival, instincts and emotions. Our frontal brain, developed much more recently, is in charge of reason, problem-solving, and complex analytical thought. Both are useful, but often work against each other.

As you pitch you have the opportunity to appeal and satitate the croc brain, opening a safe pathway for the prefrontal cortex to engage. Starting a pitch with the big picture and some emotional hooks, will enable you to garner the attention to move them into the prefontal cortex and actually pay attention to and absorb your graphs, diagrams, and financial projections. Don’t start out technical. Be aware of what part of the brain you’re speaking to.

As the founder, when it comes to telling your own story — the personal journey of how you got to this place — make it super brief, no matter how rockstar you are. Figure out a way to communicate what is best and most relevant about you in 90 seconds.

VI. Master eloquence

Eloquence is defined as having or exercising the power of fluent, forceful, and appropriate speech. If you can say it in fifty words, you can say it in fifteen. Be discerning and disciplined to avoid TMI. Information overload is one of the surest, fastest ways of losing your audience. If you can explain what you’re doing to a 10 year old in 10 minutes, you have achieved an amazing degree of self-understanding and succinctness.

VII. Clean & beautiful (but not extravagant) design

Bad design hurts your message and good design will beautifully support your message without getting in the way. You don’t need the most amazing design in the world and if your visual design is stronger than the message, you could come across as having spent unnecessary resources dressing up a half-baked idea. Get the content strong and then go for clean visual design that absolutely supports the message. This is especially true if you’re in seed stage and haven’t invested in or built an identity and brand yet.

VIII. Energy & power dynamics

The final piece in perfecting a pitch is in how you tell it. Somewhere between 70–93% of what gets communicated happens non-verbally. Awareness of the energy you bring, the energy in the room, and who holds the power in any given moment, goes a long way in determining the outcome of the pitch. For example, if you show up with a vibe of neediness, you give the power away. Walk into that room pretending you need nothing from them and notice how the playing field stays more equalized. A vibe of humble confidence goes further than egotistical idealism. The best thing is to show up authentically as if you have nothing to lose (even if you have to pretend) and pitch from your heart.

To really conquer all of the above, an outside objective party can be extremely helpful. Nobody knows your company/product/idea better than you do, but your deeply subjective understanding can get in the way of clearly defining the essence, telling the right story, and in keeping it brief and concise. Seek honest feedback and somebody who can help see things you may be subjectively blind to — find somebody you trust or hire Moonshot. And, remember that a “no” can be valuable feedback — ask why when you get turned down. Pitching perfect takes practice and refinement. Be creative and use your story as a captivating invitation into the future of your dreams and convictions.