Living In The Future: How Pattern Breakers Defy Convention To Design New Categories

What would have to be true for that future to exist?

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Dear Friend, Subscriber, and Category Pirate,

Welcome to a Contributing Pirate mini-book, where successful Category Designers share proven strategies for creating and dominating new market categories.

This month, we’re featuring the legendary Mike Maples Jr. — a venture capitalist and founding partner at Floodgate. (You might recognize Mike from mentions in mini-books like The Breakthrough Game and The 3 Marketing Metrics To Rule Them All. His thinking and work are legendary.)

Now, Mike isn't just another Sand Hill Road investor.

He's a pattern-breaking pirate who spotted Twitter (as Odeo), Twitch (as Justintv), and Okta (as Saasure) before they became Category Queens.

At Floodgate, Mike searches for founders who don't just want to stay stuck in the “Better Trap” — they want to be different. His Substack Pattern Breakers is a masterclass on the rare species of startup founders who design entirely new categories by breaking free from conventional thinking.

So, what makes Pattern Breakers legendary?

Pattern Breakers propose ideas that seem impossible at first.

They don't just improve what's already there — they set entirely new standards.

Take Lyft, a company that didn’t just make transportation easier but introduced a new way for people to get from point A to point B.

Consider this:

• Lyft didn't say, "Let's build a better taxi company"

• They asked, “How can we redesign urban travel without taxis?”

• They imagined, "What if getting into a stranger's car became normal?"

That's not innovation — that's CATEGORY DESIGN.

Or take Tesla’s Cybertruck.

They didn’t design a truck that could be directly compared to the Ford F-150 — they created a truck that couldn’t be ignored. (A polygonal beast that looked like it escaped from Blade Runner!) And the internet lost its mind. It caused debates and broke the mold of “normal” trucks altogether.

Like Category Designers, Pattern Breakers don't compete.

They create entirely new games.

Pattern Breakers create products so different, people forget about the other choices.

The journey of a Pattern Breaker doesn’t stop at having an original, bold idea.

They create different WORLDS through the power of Languaging. For example, OpenAI didn't get stuck in the "artificial intelligence" trap. They introduced:

• "Generative AI"

• "Large Language Models"

• "Prompt Engineering"

Each new term isn’t just vocabulary.

It’s Languaging in action, which creates new mental real estate in our brains.

Pattern Breakers have a "Visitor from the Future" mindset.

What separates legendary Pattern Breakers from everyone else? They don't live in the present. They're visitors from the future.

Airbnb wasn't trying to build hotels 2.0. Brian Chesky and team saw a future where:

• "Home" could mean anywhere

• “Strangers” could be trusted

• “Travel” could feel local

Airbnb designed backward from that future, creating a new category of hospitality.

Being a Pattern Breaker means living in the future and aligning your vision not with what is currently popular or profitable but with a different future reality. One that you can see and feel before anyone else. This “visitor from the future” mindset allows you to embrace ideas that seem too radical, too risky, or too controversial.

(Sound familiar?)

Mike teaches us that with a combination of “inflections” and “insights” — small hints and big ideas about what the future could look like — you can create a new category.

Now, let’s dive into how to become a pattern-breaking pirate:

Every word that follows comes straight from Mike Maples Jr. We're sharing his wisdom exactly as he wrote it. Because when a fellow category designer speaks truth, you don't mess with it.

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What are Pattern Breakers?

David Foster Wallace’s commencement speech at Kenyon College in 2005 is one of my all-time favorites. He opens it with a fish story: