Gustave Doré, Jacob Wrestling with the Angel (1855)

It was one of those standard introduce-yourselves moments around the buffet line, but then someone dropped a nostalgia bomb:

"WinZip?" I replied, "like the little piece of Windows software we all used in the 90's?"

'Yeah! We're still here ... you know every time you send a file with Gmail with an attachment and it turns into a zip? That's us.'

Stunned admiration of their pivots and adaptations aside (really, can someone dive into that?), the concept of compression has always delighted me. Somehow, you can take a thing, make it smaller, and then someone can make it bigger again? Just like that? What? Witchcraft!

And yet, this is also how nearly all communication behaves, or misbehaves. I say a few things — maybe in a tweet, and maybe it resonates, and you tell your friend about it. Less than 280 characters becomes a hundred words.

On the flip side, these 400-500 words I'm writing this morning might be something you bother to condense and share (or not!).

Checksum Fail

Let's pretend we're trying to share our early-stage, pre-fit startup with someone we meet at a conference. We'll call it Exportify.

Them, glancing at your nametag: 'So what's Exportify?'

Us: "It's a thing where, well you know how sometimes you need to create a report? Maybe you're a dev at a company, and people are asking you for reports from your database ... and so we make it easier for that person to create those reports for anyone that asks by giving the other person a way to do that without bothering the dev."

'Oh, so you're like a low-code platform for the non-dev to run queries?' (Attempt to compress.)

"Not exactly? I wouldn't call it low-code? It's more like it just doesn't require the same kind of access as the dev has." (Compression failed.)

'Oh. Okay.'


This conversation is over (and it ended somewhere before the ending). The inability of that new person to compress our word salad about Exportify into their own tidy tarball means they are extremely unlikely to share it with anyone else.

The burden of carrying whatever all that was ... is just too much.

Words with Friends

Fortunately, you don't have to wait until the buffet line. You can play this torturous game internally: just ask everyone "what is X?" and compile the answers.

If you're pre-fit, the odds of everyone giving the same answer without looking at what's written on the About Us page are abysmally low, because most people, especially founders, love to decompress ideas into longer formats. We're trained to do it from grade school: "Write at least a five page essay on ____."

More words is more nuance, more persuasion!

Then we leave the more difficult operation to chance: each listener runs their own proprietary algorithm to compress the 5,000 words you've pitched and shared with them about Exportify to generate a tidy summary.

And it's wrong every time, isn't it?

280 bytes or Bust

Instead of leaving it to chance, we need to lead by providing an easy-to-share, concise answer that our listeners can carry in their mental cache.

And it needs to be an answer that, when decompressed, has the best chance of matching how we also describe it in long-form.

Sorcery! How?!

By first wrestling with our own understanding: "Is Exportify low-code? What is low-code anyway? Is it a platform? What's a platform? Isn't everything a product, really? Maybe it's a tool? No, it's not a tool, it's an app?"

They say Dostoevsky could tell you about not just the main characters of Crime and Punishment, but also all of the relatives, friends, histories, and events that only happened off page, off plot, out of the reader's sight.

Do you understand the words of your own positioning statement?

Developing this depth is hard, time-consuming work. But it's also tremendous, because this single statement — clear, concise, but spring-loaded with meaning, when placed at the top of every investor update, about us, bio, and buffet line, becomes a highly-efficient vector for growth.

Are you wrestling with words?