A Must-Read Meta Guide To Pitching Investors

Despite the plethora of good writing about how to construct and deliver a successful investor pitch (Wolfe, Lee, Sequoia, among others), many entrepreneurs still struggle with this seemingly minor but critical function. What is the missing wisdom that might universalize the great pitch?

Before I become the thousandth EagerJohnny to attempt to unravel this mystery, let me be clear that I’ve seen many hot, clear, concise, compelling pitches. So, for those of you who know the drill, please ignore this completely. Pitch. Raise. Build.

This is for those who are having more trouble. And to you I want to start by saying: it’s f&%#ing hard so throw your shame in the proverbial garbage, hunker down, dig in, and get ready to bust your ass. If you do the work, your pitch absolutely can be precisely as good as your business, which presumably you think is amazing.

I intend for this article to serve as a meta companion to the many more direct and topical treatments of pitch development out there. (For a broader meta-guide of sorts to the fundraising process as a whole, see Paul Graham’s epic overview.)

Other authors will expertly tell you about what needs to go in your pitch, how to get meetings, how to think about your raise financially, and so on. All critical. Study up. I’m going to try to tell you how to think about pitching so that you might imbue the task with the attitude, focus, and enthusiasm it merits.

Here we go…

Tell a Story

Pitching is not a formulaic exercise in information dissemination; it’s story-telling.

If you’re thinking, ‘I need 15 slides outlining the market, competition, product, team, projections, etc.’ you will inevitably end up with a disjointed, blocky, generic, annoying pitch.

Instead you need to be a capitalist bard of sorts.

You’ll end up covering the same canonical ground as Mr. Information, but you’ll do so in a way that guides your audience to actually believe in what you’re doing.

Through the medium of the pitch you are telling a story of human need, epiphany, invention, strength, stamina, and ultimate victory. Formulas are boring; stories are compelling.

Tell the Truth

Just because your pitch is a tale doesn’t mean it’s a tall tale. Quite the opposite. Your story is a distilling and enhancing mirror of the truth.

This is part of the reason pitch development is such a mission critical act for the entrepreneur. The problems in your pitch are almost always not only problems in the story you’re telling but also problems with your actual business strategy.

For instance, if the part of your story in which you explain how your business becomes huge feels a bit jagged or unclear, it’s almost always because your actual growth strategy isn’t clear. The error people typically make in such cases is to patch up the story. But inevitably, if you take the patch approach, your pitch will end up feeling a bit…fishy. On the other hand, if you recognize pitch development as a lever-moving reflective process, you’ll actually assess and potentially adjust your growth strategy.

A second, even more common example: bifurcation. So often entrepreneurs have a huge vision. They want to own X. Power to them; this kind of drive and grandiosity is the stuff of greatness. But go one strategic layer down and you find that this kind of universal ambition can belie a problematic, simultaneous pursuit of multiple channels/areas/etc. You can feel it in the pitch, this sense that you are listening to multiple related short stories as opposed to one singular tale. It’s not categorically problematic to have multiple characters and an arc that leads through multiple settings. Complexity isn’t bad. But it should be one story. If it’s not I’ll bet you that your company has a focus problem.

Your ability to tell a concise, compelling story about your business is a sure shot barometer of your own strategic clarity. So, use the pitch development process to actually improve the truth you’re telling.

Make it Ring

Your deck’s design … your tone, pace, diction, prosody … perhaps even what you wear — every detail of your pitch should serve the story. It’s a production, even if the final result appears exceedingly casual; so make it ring.

Your pitch should almost smell like your company. Otherwise, your audience will be left with a subtle inadvertent confusion about just what you stand for. You are enacting your brand.

Here’s a classic example of screwing up the details: the misplaced use of analytic language, salesy branded language, and what one might call ‘hipster opacity’ (e.g. vague statements about the future of mankind’s relationships with machines.) All three have their place, but each can be a true turnoff when misused, creating a sense of dissonance for the audience, a lack of trust in the integrity of your story. Analytic language can be deadening and paint your team as lacking inspiration. Salesy, branded language can feel like a lie that’s covering for lack of hard proof and conviction. And hipster opacity is basically always bad unless you’re building something truly radical; even then, as in most great stories, things are usually best left to speak for themselves.

Point being, your story is told through the details, so craft it with care.

Be ON

A great pitch utilizes intuition as much or more than it relies on logical acumen.

For instance, on the fly and without any analysis, you should be able to answer these kinds of questions:

• who is the most important person in the room right now and how do I speak to their fundamental perspective without alienating anyone else?
• who doesn’t feel heard right now and how can I address that without calling attention to it?
• how casual should I be right now in order to project strength but not seem lackadaisical?
• what criticisms are people feeling that I can address without seeming defensive?
• does this meeting feel exciting, creative and positive right now? If not, how can I un-depress things?

This is the kind of subtlety you’re processing when you’re on.

Take Care of your Audience

Being ON not only means cultivating the intuitive awareness of your audience I just described, but also acting on it.

An example: In any given pitch there are at least 10 micro directions that aren’t essential to your story but might feel essential to some people. For instance, one guy might really care about the details of your growth story and think the pitch is just a bit hollow without it. And person might need a true grasp of the total addressable market to really get the story. Your job is to be ready to seamlessly serve each of these audience members.

For this: tools. Appendices, for instance, can help you tell the micro stories your audience needs. If someone asks about growth, you hop to that appendix slide. Likewise for TAM. Be an appendix ninja: seamless, fast, calm. ‘Well, Jim, thanks for asking about growth. Let’s take a look…’

Take good care of your audience.

Always be Buying

Don’t get confused into thinking that taking care of your audience means pandering. Quite the opposite. You are the buyer.

This is the single hardest thing for most people to really grasp about pitching: you are the buyer.

I don’t care if you’re pitching Jim Robinson, III on an Amex competitor. You’re the buyer. The buyer thinks: Is Jim the guy for me? What does he have to offer? Why does he move the lever for me?

This doesn’t mean you’re not selling. This IS selling. Your skill in this is an essential tool in the CEO’s belt and thus part of what’s being assessed in the pitch meeting. Everyone in the room knows it. You can be damn sure Jim knows it.

Indeed, everyone in the room usually understands all the dynamics; we play them out anyhow not because we are participating in some strange postmodern puppetry but because watching how everyone plays this gameIS the game.

“Always be buying” has nothing to do with arrogance. Not at all. Opposite! It means being generous, gracious, open, connected and calm. Precisely because you have taken on the inner stance of not needing the investor you are able to demonstrate these qualities of strength.

Arrogance is a tell; the narcissist is holding a hand full of fear and need. The humble, clear man is sitting easy with quad kings.

Practice, Practice, Practice

Unless you’re Dr. Phil, this all takes practice. Practice like you’re starring in the middle school play. Use a video camera. Use friends. Use a mirror. Whatever it takes. If you think something is off in your pitch, trust that instinct, dig deep and fix it. This is how real confidence is built. And confidence sounds good.

Entrepreneurs often don’t anticipate just how hard pitching is, particularly when they’re new at it. Over twenty significant drafts and many hours of practice are par for the course. If you don’t treat pitching as the challenge it is, if you approach it as a distraction rather than a top priority, it will inevitably taste like unbaked bread. But if you give pitching the time and energy it merits, it’ll sing.

I would hesitate to suggest this kind of intense practice — and the general inner contortionism required to arrive at and deliver the great pitch — if it was purely for the sake of the pitch itself. Time is the most precious commodity for the entrepreneur.

But the work you do on your pitch will make you so much better at building and leading your company.

Your sales pitches will improve. You’ll become a better recruiter. You will garner press more effectively. You will manage your Board with more ease. You will become a more powerful product leader. You will refine and sharpen your overall strategic vision. After all, you are a protagonist in this story so you better learn to tell it well and make it epic.

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