The Three Rules of Pitching that Raised $2,300,000 for my Startup

The startup “pitch” has become a trope — like marriage proposals, diaper changes, and employee firings, almost all of us think we know how to do one… until we actually need to.

That’s when we realize that no matter how many times we thought we’ve seen them before, we have no idea how to make them great when it’s our turn. If we’re lucky, we come to that realization before we get down on one knee and present the ring. If we’re not, “will you make me the happiest X on Y” will do in a pinch, as will “we are on a mission to disrupt Z by leveraging blockchain, you can see our whitepaper after the ICO”.

But while a sunset marriage proposal or a Shark Tank pitch may be the appropriate choice in certain cases, more often than not, we need something uniquely suited for what we’re doing. And that’s where, as someone who’s pitched on TV, in boardrooms, and in real elevators — I can offer some perspective.

Rule 1: Pitches are when you try to convince someone of something

“Well that’s not a very insightful rule,” you may be thinking. And you’re right — it’s not. The insight is that this is one of the three most important things about pitching.

So why is the simplest possible definition of pitching a full third of the advice I have for you? Because it’s the single most common aspect of pitching I see founders forget!

Founders aren’t to blame here — “pitch competitions” are. I’ve seen a lot of these, primarily when I was still in college: An event for startup founders to “pitch” their company, where they are evaluated not on some concrete metrics relating to their business, but on “how good their pitch is”.

First, to beat my dead horse of a metaphor, this is like evaluating marriage proposals on “how good their marriage proposal is”. What does that even mean? Isn’t the point of a proposal the fact that it’s a very special conversation? A singular moment of love and connection between two people? If we held marriage proposal competitions, would we care more for the passionate couple alone on a hike, or the professional marriage proposers skydiving into each other on a speedboat?

In my experience with pitch competitions, it’s usually been the latter: Founders that are great at presenting and terrible at building a company. So pah to pitch competitions, at least the ones that don’t have clear evaluation metrics for their competitors. But pitch competitions that do have those metrics, well… that’s closer to reality.

So what is the reality of a pitch? It’s trying to convince someone of something. Period. There’s good news here and bad news — the good is that we’ve all been pitching for years, since the earliest memories of our childhoods. We’d pitch sleepover plans to our parents, trying to convince them that we deserved a night away. We’d pitch our forcefully activity-packed lives on college applications, trying to convince U.S. News & World’s darlings that we were smart and accomplished enough for them. And then we’d pitch our friends, trying to convince them that going out with us would be fun, so that we could pitch girls (or boys), trying to convince them that coming home with us would be fun.

So pitching is something that we’re all good at. Otherwise we wouldn’t have made it anywhere in life. And if you can read this article, congratulations, you’ve made it somewhere in life.

Time for the bad news: Most of your life’s pitches have had an obvious someone and something, which is why you’re actually quite good at forming pitches and winning people over… once you have these two elements pinned down. Because the better your grasp on them, the better your pitches will go. If someone is a friend you know extremely well, and something is to hit the bars with you tonight, that’s an easy pitch: You know your friend’s circumstances, desires, and fears. You can be conscious of their recent breakup and excite them about the possibility of meeting someone new tonight, and assure them that you’ll make certain they’re in bed early enough for work in the morning. But if someone is a stranger to you, you’re shooting in the dark — it’s a much tougher sell, because you lack the information to make it.

When you’re an entrepreneur, your someone and something change with every pitch. Worse yet, they’re often unclear and genuinely difficult to discover. This is my gripe with pitch competitions — if the evaluation metrics aren’t realistic and specific, competitors don’t have an idea of what the real something in their pitch is, and end up copying the popular trope of ‘pitching’, i.e. laying out the template defaults of their vision for a company: That’s how we’ve arrived in a world where every startup “has the right team to change the world” and “will become a billion-dollar company by capturing just 1 percent of the market”.

But even in a real-world pitch, the someone and something can be difficult to pin down. I’ve given very different pitches of my company to potential employees than to new investors. Even within the investor pitches there’s been huge variety — between the day I pitched Matthew McConaughey’s brother on national TV, and the day I pitched the Duke Angel Network in their conference room.

It’s absolutely critical that you are conscious of this as you formulate your pitch — don’t just make a “good pitch” that presents your startup in a favorable light. Remember that when you pitch, you are trying to convince someone of something. And the clearer your understanding of who that someone and what that something are, the better your shot at convincing them.

So if you’re actually working on a pitch right now, quickly answer these two questions: Who are you trying to convince? What are you trying to convince them of? Once you have an answer, you can start crafting your pitch.

Rule 2: 20% of your pitch carries 80% of its importance

I know it’s a self-help cliché to bring up the Pareto distribution, or 80/20 rule — but I think keeping that split in mind is critical to crafting a successful pitch.

Let me put it this way: When I was pitching my startup, Carpe, to venture capitalists, my cofounder and I would use a roughly hourlong presentation. In shorter meetings with angel groups, we might use a ten-minute deck. In even shorter networking events, a two minute stand up pitch would be all we had time for. And at the extreme short end, when pitching Carpe to our customers, we’d show them our 30 second TV commercial.

That TV commercial would’ve shown VCs most of what they needed to know.

The point isn’t that you should make your pitch short (though, in many cases, you should), but that you need to have a very solid and succinct grasp of the few core elements of your pitch, and spend most of your preparation honing those; then, you should have a solid and succinct grasp of the second-tier elements of your pitch, and spend most of the remainder of your preparation honing those; and so on.

Investors will expect you to be able to present the nuances of your company and its position for well over an hour, but they won’t nitpick your payroll projections nearly as much as they will your core problem-solution paradigm. And they won’t nitpick your choice of office computers nearly as much as they’ll nitpick your payroll projections.

So how do you figure out what those core important topics are? Well, the better your understanding of your something and particularly your someone, the better your ability to choose those topics. But in a pinch, try this: No matter what your pitch is, cut it down to 30 seconds. If you had just 30 seconds to pitch your entire $100 million Series C to Sequoia Capital, what would you say in those 30 seconds?

Answering that question, and making sure those 30 seconds are absolutely killer, should be your top priority after figuring out your someone and something. It should be where you receive the most feedback, and do the most editing. And then, perhaps, time permitting, you should try the same with a 2 minute pitch. And finally, your full pitch.

Rule 3: The best pitchers are the best listeners

“Did he use the word pitcher right?” you may be thinking, “I’ve never heard that word outside of potlucks and baseball.”

Allow me, then, to define ‘pitcher’ — founder, entrepreneur, ‘person giving the pitch’: These people succeed at their highest level not by talking well, but by listening well.

I’ve seen this in myself, and I’ve seen this in dozens of entrepreneurs whom I’ve helped with their pitches. The first draft sucks — not even that, the first final draft sucks. You can have a pitch that blows your mind, that you’re certain crowds will hear as the artful words of the next Zuck. But it probably sucks: Because you are very rarely the someone whom you’re trying to convince (read this sentence again — it’s key).

The best pitches I’ve heard are the pitches that I’m the last to hear — the pitches that have been bounced off dozens of friends and mentors, and then dozens of investors of decreasing reluctance, and then off some truly excited investors, and finally bounced right into my ear. These are pitches where the pitcher has noticed when her audience yawns and when they sit up, what she receives questions about that the pitch doesn’t cover fully, what she could do without and what she’d better put in if she doesn’t want the next investor on her road show to take a call halfway through their meeting.

No single person can tell you how to make your pitch great. But if you listen to the explicit and implicit feedback of a lot of similar someone’s (this includes verbal feedback as well as true disinterest and outright rejections), you will learn what they respond to, and what they prefer to do without. That’s when you can start building the pitch that your someone wants to hear, that’s when you can start assembling the words that really do have a shot at convincing them of something.

And… that’s it. It’s a short third rule, but it’s extremely important. Great pitches don’t come from formulas and templates. They come from listening, and iteration. If you’re a successful entrepreneur, I’m confident that your customers have taught you more about how to make a great product than you could’ve ever discovered yourself. The same should be true for your pitches.


It’s hard to break out of all that our culture has come to associate with a “pitch”, and look at it as plainly as this: Why you’re pitching, what’s the essence of the pitch, and how people respond to you. But if you presuppose anything beyond these rules, your pitch will be limited to some degree — it will be derivative, a slight copy of what’s come before. And again, that may be appropriate for the right someone and something.

But unless you know that — unless you know your fiancé-to-be likes sunsets, and your investor-to-be loves discounted cash flows — then start from the ground up: And that’s how you’ll craft a truly spectacular pitch.