Cognitive Cheatcodes for Cofounders

INTRO

Hey, I’m Tim! ☕

Exciting news — welcome to the first sponsored edition of Cherrytree!

We’re still small enough that I can meaningfully share personal updates like this, and I hope the appreciation feels just as personal on your end. Thank you for being here.

Click the link below for ways to get more stuff done with AI. And to celebrate this milestone, I’ll let you in on 2 cofoundership secrets.

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DEEP DIVE

“If everyone is thinking alike, then somebody isn’t thinking.” — General George S. Patton, known for his aggressive command style and role in the Allied victory.

Mind Mechanics

These aren’t secrets born from gatekeeping; rather, they exist because you resist or overlook them. While they’ve been used in disciplines like education and behavioral psychology, they haven’t really found their place in the world of cofounding.

Work with your neurology, not against it

Your cognitive style basically describes the way you think and you can break it down in several ways:

• Field Dependence-Independence: Do you rely more on external visual cues (field-dependent) or more on internal cues (field-independent)?

• Reflectivity-Impulsivity: Do you think through things methodically or are you quick on the draw?

• Convergent-Divergent: Do you look for a single, correct solution or do you generate multiple, subjective solutions?

• Visualizer-Verbalizer: Do you prefer visual representations or verbal explanations of information?

• Holistic-Analytic: Do you see the big picture and recurring patterns or do you focus on details and components?

• Sequential-Global: Do you understand info in linear steps or do you make large jumps by first understanding the concept?

You know how you check out each kart’s stats in Mario Kart? Understanding your cognitive style is doing that for your own brain — it’s a cheat code for how you operate best.

More specifically, your cognitive style describes how you process information, which is really just how you learn and make decisions.

If you gathered the top predictors for doing great work in anything, not only cofoundership, the intersection would be some combination of effective learning and sound decision-making.

It’s equally important to know where your cofounder falls on those spectrums.

Only then can you have a fertile breeding ground for mutual understanding. A lot of cofounder conflicts I’ve seen arise from a lack of empathy because people assume their cofounder shares the same cognitive style.

“Why don’t you get it?” “What don’t you understand?!”

I don’t think it’s necessary to map out those spectrums and literally plot yourselves, but you can if you want to. I do, however, think it’s necessary to be aware of your differences.

And that brings me to the second secret.

Understanding the Conformity Matrix

Let’s talk quadrants — a concept I’m borrowing from Paul Graham.

Imagine a chart whose x-axis runs from conventional-minded on the left to independent-minded on the right, and whose y-axis runs from passive at the bottom to aggressive (proactive) at the top.

• Upper Left - The Snitches: Rule enforcers who not only insist on obedience, but believe it’s their duty to report those who stray.

• Lower Left - The Sheep: Follows the rules dutifully, but when others break them, they’ll turn a blind eye to avoid any sort of confrontation.

• Lower Right - The Dreamers: Probably don’t really know what the rules even are, let alone care. They couldn’t care less if others break the rules.

• Upper Right - The Rebels: First instinct is to question the rules. Being told what to do makes them inclined to do the opposite.

As a cofounder, you probably fit somewhere in the outlined blob. In fact, your success depends on it.

You have to think for yourself and act on it. But not all independent-minded and aggressive (proactive) people are created equal. We’ve all met the contrarian jerk who’s argumentative for attention’s sake.

So how do you use this information productively?

Your quadrant says a lot about how you handle authority. Knowing where you fall can predict how you’ll respond when the pressure’s on from “authority,” whether it’s your board, investors, or even government oversight.

(Pro tip: it’s also a smart lens for evaluating your first hires).

I’m sharing these two “secrets” because, more often than not, the challenges in your cofoundership aren’t about being cofounders — or even who you are as individuals. They’re rooted in not fully understanding why you are who you are.

Explore your differences in more detail that you initially thought necessary. It’s in the blending and intersecting of these differences that your cofoundership grows.

The best cofounders aren’t clones, they’re complements.

LAST LOOK

If you want more personalized advice, book some time with me here.

Missed a Cherrytree edition? Grab a coffee and hit the archive to get all caught up.

Here’s to many more sponsors to come!

(Don’t worry, I’m not a sellout. I’m only working with companies that actually have something useful to offer you).

Thanks!

Tim He
Founder & CEO