#1 Category Story's origin story

#1 The Origin Story

I bought categorystory.com two weeks after my first failed client engagement...

They had an opportunity to differentiate in a stale category. Their competitors came up in the late 90s and early 2000s and it showed — as in on-premise software with licenses, showed.

The strategy was clear.

Take a page out of Salesforce’s playbook, lump these dinosaurs into an undesirable bucket of sameness, and present my client’s product as what’s next.

I created a “Why Us” page that told their category story and how it inevitably led to my client’s product — the first enterprise-ready solution in their space built from the ground up as a SaaS.

This was only the beginning. This Category Story would then infiltrate other pages, emails, sales calls, investor decks, and content.

I submitted the page, BUZZING with anticipation…

And waited…

They hated it.

“Too direct”

“Too confrontational”

“Too startup-y”

They wanted the product to do the talking and let customers decide.

After some back and forth, they said we wouldn’t see eye-to-eye and they didn’t know how to explain what they wanted. Our engagement ended.

So why the two week gap between pride-stomping failure and categorystory.com?

I had to recover.

This was the first time I was told to pack up my things after six years of helping some of the most recognizable SaaS brands.

Then, I had to decide who was right.

I reflected on projects that went exceptionally well over the years and looked at my notes on SaaS companies making a splash in crowded categories.

I believed I was right and here’s why…

The barrier to entry is low in most SaaS categories and it’s only getting lower.

Feature moats flood, washing away any innovation advantage.

And companies are doing a much better job of telling “why us” product stories.

What do you get when you put this all together?

Categories filled to the brim with companies who all look, sound, and are the same as far as customers can tell.

And what happens when everyone looks the same in a crowded category?

Customers choose complacency or category champions — not you.

But some companies are managing to stand out, and they have something in common…

Companies that stand out lump their competitors into a bucket of undesirable sameness, creating space between themselves and their competitors in the minds of customers.


  • ConvertKit vs. MailChimp and ActiveCampaign
  • Ramp vs. traditional corporate credit cards
  • Riverside.fm vs. conferencing software like Zoom
  • Tom’s Planner vs. spreadsheets and MS Project
  • Fathom Analytics vs. Google Analytics and the rest
  • Statamic vs. Wordpress
  • Hey vs. Gmail, Superhuman, and friends
  • SavvyCal vs. Calendly and the rest
  • Even Magic Spoon vs. all children’s cereal

(I’ll dissect examples in this newsletter and on Twitter + LinkedIn)

These standout SaaS brands don’t stop at a “why us” story. They tell a “why us and not them” story.

Their positioning, messaging, and product all acknowledge that they they are part of a crowded category and they are not the incumbent.

Most companies aren’t doing this. Most companies don’t know how to do this. And this is our opportunity.

It’s easier to choose different.

This is why I believed I was right...

Then, I heard Guillaume Cabane (aka G), Andy Raskin, and Peep Laja say this in the most recent episode of How To Win and knew I was right…

“Lack of differentiation. Just talking about your product. Many companies, when I look at their copy and ads, it’s just me me me me. If there’s 20 companies like yours, I will not feel the subtle difference. I’m not going to care.”

Translation: Even if you do a good job of telling a product story that connects your customer's problems, their desired outcome, and your product — you will still sound like the others in your category who are also doing a good job of this. You won't stand out.

“Here’s how we solve your problem and how we’re better than the others. It seems like a reasonable approach, and maybe it worked back when markets had few enough players that buyers could ignore the bluster and sort through all of the claims. But that’s not what markets look like today. Each of you probably competes against not a handful of competitors, but dozens all screaming ‘why us’ to customers.”
Andy Raskin

The key word here is “better.” In a busy category, it’s hard to make the case that you are unequivocally better, especially since you’re probaby marginally better at best. But you can convince them you are different. This is the opportunity most companies miss.

“Most brands operate in saturated categories — there are hundres of alternatives. Most of which look the same and say the same things. If you speak about yourself as if you’re the only one doing what you’re doing, you’re making it needlessly hard for yourself. So many SaaS tools lead with product-based messaging and state the plain obvious, as if that’s unique or impressive. Marketing has always been about the customer and not the competition. Too much focus on the customer and you end up with sameness. Most customer insights are category level insights, so everyone ends up solving for the same problems in the same way. This results in companies playing a game they can’t win.
The barrier to entry of starting a new business has never been lower. So if you want your me-too tool to be picked by someone, odds are heavily stacked against you.
Differentiation is about standing out and providing a reason to choose you over others. You’d think companies would be all about that. Curiously, not so much. The opposite is true. Sameness is the default. Sameness is the combined effect of companies being too similar in their product, poorly differentiated in their branding, and indistinct in their communication.”
Peep Laja

And this Twitter thread by April Dunford was the cherry on top.

The combination of seeing behind the curtains of dozens of SaaS clients, reviewing many more, and these experts echoing my own thoughts convinced me I'm on to something.

This is how Category Story began.

What to expect from future issues:

  • Analysis of Category Stories out in the wild (video + written)
  • The "how-tos" of crafting a Category Story of your own
  • How to infuse your positioning, messaging, content, and sales calls with the Category Story
  • Links to articles, podcasts, videos, and other resources
  • Changes in format and design from month to month as I feel this out
  • Your questions answered (reply to this email with any questions or recommended topics)



Hi, I’m a creator

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