How to Tell “Strategic” Stories About Your Company: Part 1

Andrew Yang
The Core Message
Published in
5 min readApr 6, 2021
Photo by Jaime Spaniol on Unsplash

In the past few months, our team that works with entrepreneurs on their pitching began noticing two very different “types” of stories founders tell about their companies.

The first type goes something like this:

Founder: I’ve always been passionate about this problem. I personally suffered from it (with touching story), and I’ll stop at nothing to solve it. People told me it was impossible, and there were a series of obstacles in my way, but I fought through all of them and finally made a breakthrough.

Let me show you…

We’ve always loved and admired founders with this kind of story. Their passion literally leap across the room at you, and you can’t help but root for them.

And then there’s the other type of stories:

Founder: There are lots of problems in this industry. We studied all of them, and saw that for problem 1 the barriers are too great; problem 2 is easier, but the market needs education so it’s too costly; problem 3 has potential but competition is already too fierce. Problem 4, however, has the right mix of growth potential, lower barrier, and yet being overlooked by major players.

Let me show you…

Pretty different, aren’t they?

But why does this matter?

Your Stories Reveal Who You Are

There is a LOT of advice out there on how founders should pitch and tell stories. Most of them focus on the WHAT—which information to include, how to arrange them, the data, etc. — and the HOW— how to project confidence, hold your body, move your arms, lower your voice, etc.

And of course, there’s also entire industries around designing pretty decks.

But after coaching over a thousand founders, our team has come to believe that the WHO is just as crucial — namely, the type of stories an entrepreneur tells can reveal who they are.

What do we mean by this?

Just go back and look at the two types of stories above, and it should be obvious that they’re told by very, very different kinds of entrepreneurs.

Let’s just call the first group heroes and the second group generals.

Heroes smash barriers

Heroes have incredible devotion to a cause and equally incredible drive. The stories they tell are about a problem they care deeply about, and how they employ both creativity and persistence to overcome adversity.

We call them “heroes” because no matter how many walls stand in their way, they’ll smash through them and save their users (or the world):

The hero will keep fighting no matter how many barriers are in their way

Based on the scientifically rigorous method of “querying our imperfect personal memories”, our team has found that heroes are far more likely to be first time founders, experts who have devoted their careers to a specific technology or problem, or investigators coming out of a research/academic program.

Generals pick their battles

Whereas heroes can be single-minded about the challenge before them, generals begin their stories not by charging right into battle, but by standing back and surveying the entire battlefield.

They may be interested in specific problems as well, but this is coupled by cool-headed assessment of the odds: “We were interested in this problem, but found that the path to market is too hard.”

And they look broadly to identify other opportunities: “We discovered another niche with a similar problem, where our capabilities can make quick impact.”

Generals survey the entire field to find the best entry point

In our experience, generals are more often veteran founders who’ve had previous successes. They could also be former investors or senior executives from large global companies.

Because they’ve fought so many battles (read: made so many mistakes), generals have learned to be aware of the larger forces such as:

  • Competitive landscape (is everyone crowding around a certain space?)
  • Regulatory changes (favorable law changes on the horizon?)
  • Technology shifts (has someone built tools we can leverage?)
  • Etc.

We’ve even met “generals” who spent 2+ years studying a range of problems, looking into potential competitors and partners (read: potential acquirers), and finding feasible differentiation — all before committing to a venture.

In other words, while heroes tell passionate stories, generals tell strategic stories.

So why are we telling you all this?

Founders Need Qualities of Both

We believe that both heroes and generals are needed— heroes have the devotion and resilience of fight through obstacles, while generals offer the strategic thinking to find the best course.

We’ve noticed however that while investors — VCs and angels alike — say they love heroes, they’re secretly even more in love with generals.

This could be because generals are simply a rarer breed. After all, there are lots of passionate people who want to become successful entrepreneurs, but far fewer who actually do. And the same goes for successful investors and corporate executives.

It’s also pretty hard to fake being a general. Most people can come across as intense and resolute, but very few can pretend to have a strategic mind and high-level industry knowledge.

But here’s the good news — and it’s a working theory of ours:

We believe that even for first time founders, it is possible to train yourself to think — and speak —strategically like generals.

*Yes, the thinking part is even more important than the speaking.

We want you to keep being a hero — but also master the strategic craft of generals. Then you become a strategic hero (or a heroic general??).

So, in the next part of this series, we will look at a first-class example of strategic storytelling, and dissect its anatomy.

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Andrew Yang
The Core Message

Former presidential speechwriter. Now helping CEOs and founders tell better stories. Co-founder of Presentality