The Most Underrated Pitch Skill is Concision

The fundamental reason a founder needs a tight pitch is because anything less shifts the burden of clarity onto the listener. This is the last thing the founder wants. If the VC is required to decode the message then there is the real risk they cannot which effectively ends any chance of success for the founder.

Tight pitches are difficult to construct because the concepts that make a startup a good investment are always nuanced. (Which is why good ideas and good investments are not plainly obvious to everyone.) To craft a tight pitch is to communicate nuanced ideas. And that is not easy.

Before a VC can even consider the merits of an investment opportunity, they first have to “get it”. Many pitches don’t even clear this first hurdle. I suspect there are startups that died for lack of funding not because the business was untenable but because they were simply unable to make the VC “get it”.

I have first hand experience with this: I once ran a startup that didn’t get funded by at least a dozen VCs and then, once we finally crafted a tight pitch, did. These days it happens to me as a VC: I listen carefully and ask questions and still don’t get it.

Of course my acuity level and not the founder's communication skills could be the reason for this. But it actually doesn't matter. Unless the founder has at least one term sheet from elsewhere, it is incumbent on them to overcome this. It’s taken little time as a VC for me to learn that many do not.

There are minimal resources that I can find that offer solutions for founders on this. The internet will yield lots of articles offering (often valuable) tactics for pitching well. But this challenge is more foundational; it’s rooted not in pitching but in fundamental communication skills. The best pitch tactics will not save a founder whose fundamental communication is flawed.

I asked Abraham Thomas, who knows a lot about these sort of things, about the lack of resources on this. His reply:

My impression is that almost nobody talks about this aspect of the pitch, perhaps on the theory that it can't be taught or optimized? Which is completely wrong, of course.

I think he’s correct, it can be taught. In fact, I am going to attempt that right now. Even better, while I will start with first principles I will actually present a recipe that I believe can make any pitch better.

Concision is the Hallmark of Mastery

A tight pitch communicates nuanced concepts precisely and efficiently. There’s a word for this: concision. And here’s the thing about concision: it is the hallmark of mastery.

One of the clearest signs that someone is a bona fide expert in a subject— whether in string theory or Pokémon — is their ability to discuss the topic with precision and clarity. I say “discuss” because anyone can recite a tight soundbite in spite of only superficial knowledge. But if you can engage in a dialogue where I interrogate you and you keep replying with concise answers the only explanation is that you have total command of the subject at hand.

Concision implies expertise. The converse is not true. Expertise is insufficient to communicate concisely. It’s the basis. You can know something inside out but be unable to explain it well. If you want to explain it well, let alone be concise, there is no substitute for spending time crafting the words that actually work.

Consider your favourite intellectual. I’ll use Chomsky for example. If you watch someone like Chomsky take a question, you almost always witness a masterclass in concision. Why is it that intellectuals like him can respond so concisely to whatever you ask them? It’s not just because they are experts. It’s because they’re not formulating answers to the questions they are being asked in real time. They are reaching into a bank of pre-constructed articulations, tweaking them accordingly and delivering.

They are equipped with this bank for one reason: they write. Writing enables oral communication because its by-product is clarity of thought. Composing even one tight paragraph on a nuanced or complex subject demands intellectual persistence. Maybe on the 10th iteration, you succeed. At this point not only do you have the prose you just wrote, you have a concise articulation for one concept embedded in your mind.

Imagine what happens to that bank when you author an entire paper or a book or a series of books. The bank becomes so rich that every question lobbed at you is a softball. You just mix and match a few of your sound bites and hit yet another home run. Show me an intellectual who is good on stage and I’ll show you a writer.

A founder can adapt these principles to great effect. Two things simplify the adaptation. The first is scope. A founder does not actually need to develop a comprehensive articulation on that much. They just need a series of excellent answers to a well-defined set of questions, a dozen or two at the most. This is because there is basically one prism through which every VC looks at the world.¹ For a founder it means they can know with high certainty what questions are coming their way in a pitch meeting, regardless of who is across the table. (What problem are you solving, why this team, why now, etc.)

The second difference is AI. Until recently, perfect prose was available only to someone who could actually write well and could invest the hours or days the process demands. Today perfect prose is available on demand.

Here then is the recipe I promised:

For each question you know you must speak to:

1. Write an answer as verbosely and imperfectly as you want, just make sure it is complete and contains the points you think are important.

2. Instruct your AI of choice to craft a variant of what you just wrote that leaves out nothing but uses the minimal number of words. Iterate between this step and the previous one until you have a perfectly complete and concise answer.

3. Memorize it so you can recite it almost word for word. You have to do this because you did not write this text yourself and hence the answer is not stamped in your mind the way it would have been had you suffered the pain of actually composing the text. (Seriously, don’t bother with anything I prescribe here if you intend to skip this step.)

4. Speak your answer to the mirror a bit. This is speaking skills 101 stuff. (Saying it in your mind one hundred times is no substitute for saying it out loud even a few times.)

That’s it. If you bake your pitch using this recipe – which still demands plenty of work by the way – your messaging will be tighter. The listener will not only “get it”, they will infer your expertise because of the conciseness of your communication.

Let me underscore this formula with my experience. A few hours before we got the term sheet that effectively launched us toward success, my co-founder and I remarked to each other how “easy” the meeting had been.

We were wrong. It wasn’t easy. It was just that we had reached a point where there was nothing anyone could ask us for which we did not have excellent, pre-articulated answers. Note that from our first failed pitch to our last successful one, nothing about our company or opportunity changed. The only thing that changed was the quality of our communication.

This article, as good or bad as it may be, is more concise and more clear because I told AI to make it so. Effective communication by precision of thought was a superpower from the Enlightenment until November 2022. It is now available on demand for any founder who wants it.