Clarity of Thought

The Great Founder Sifter

May 31, 2025

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I'm a voracious notetaker. I have a tick that may be the limiting factor on my greatness. I feel compelled to record things. In addition to logs of the books I've read, the dialogues I've had, and the spiritual impressions I've received, I have also kept notes on every company meeting I've had since I started investing in 2014. In the last ~11 years I have had 2,851 meetings with founders. In that time, I have worked at five different venture firms and have been a part of deploying nearly $2B of capital. Across that entire corpus of experience, if there is one phrase that has come up over and over and over again in the pursuit of excellent founders, it is "clarity of thought."

There is an elusive element in explaining this idea that has a sort of "I know it when I see it" element. The best founders I have ever interacted with articulate themselves with precision, logical coherence and flow from one idea to another, a focus on the most relevant information without getting distracted by the logical course at hand, and an "earned insight" into the complex issue they're tackling that gets right to the center of the opportunity.

The biggest obstacle in achieving "clarity of thought" when you're in the earliest days of building a business is the fact that it can be difficult to see clearly something that is non-existant. But that is the exceptional capability of world-class founders. They can see clearly that which does not yet exist. And then they spend exorbitant, God-like amounts of effort and grit willing that thing into existence. When you talk to someone like that about their business, they can see, with immense clarity, what it could become.

Does that mean the founder can predict the future with certainty? Obviously not. Their idea can evolve over time in dramatic ways. Their insight can be wrong. They can miss the mark on the particulars of what they attempt to build. But the outcomes, in that moment, are not the measure. Clarity of thought is, at first, independent of the eventual outcome. It is, instead, demonstrated by not just the clarity of the thoughts expressed, but the quality of the underlying thinking being anchored in truth.

Clarity of Thought: a History

When I dug into the history of the phrase "clarity of thought," I found it had a pretty reach interconnected history across the hallmarks of critical thinking and effective reasoning. A couple of examples:

Socrates, Plato, and Aristotle: All emphasized clarity in reasoning. Socrates' method of questioning aimed to clarify assumptions and expose contradictions. Aristotle’s Organon (a collection of logical treatises) outlined the structure of clear and valid arguments. "A deduction is speech (logos) in which, certain things having been supposed, something different from those supposed results of necessity because of their being so."
Thomas Aquinas: Used the Latin word “claritas” (clarity or brightness) to describe not just physical clarity but intellectual lucidity. That included clear definition of terms, rigorous distinctions, and the transparency of argumentation.
Descartes and Spinoza: They emphasized clear and distinct ideas as the foundation of knowledge. Descartes famously wrote that truth must be built on ideas that are “clear and distinct.”
Bertrand Russell, Ludwig Wittgenstein, & A.J. Ayer: Each prioritized linguistic clarity and logical form. Wittgenstein's Tractatus begins: “What can be said at all can be said clearly…”.

A lot of these core ideas throughout the philosophies of a half dozen thinkers reflect critical concepts that I think demonstrate the characteristics of "clarity of thought." So when I think about how they apply to founders, I walk away with the components below.

Clarifying Assumptions & Exposing Contradictions

Any sound logical exercise begins with establishing what assumptions are being made and what is true, regardless of the outcome of the idea. Other people refer to this as "first principles" thinking. I've written before about this idea of unpacking the core threads of an idea:

"You can't answer the question ‘why should people care?’ You have to answer the question, ‘why should I care?’ And that brings us back to first principles. What is your value system? Why should YOU care?"

The best founders are uniquely good at immediately beginning from a place where, when you hear their starting point, you think it is gobsmackingly obvious, almost to the point of being laughable. Last week, I wrote about a Marc Andreessen quote where he explains why founders so often think they’re too late:

“You’ve got some idea in your head, and as far as you’re concerned, the world should already work this way, which is why you’re pursuing it. And so it’s a little inexplicable as to why it hasn’t happened to it… It must be just about to happen and I must be too late.”

As the presenter is outlining these concepts that, in the moment, feel obvious to you, its typically not because you whole-heartedly agree with every aspect of the concept. It’s because the presenter has offered a personal statement of logic in way that is very compelling for you as well.

Often where this comes from is demonstrable evidence; its not just your conjecture on the space but its speaking to your own lived experience or the demonstrated experience of early design partners or customers.

The most compelling discussion of a topic often comes from people who have very clearly spent time thinking deeply about the issue and its interconnected ideas. Clarity comes first from raw curiosity. And in my experience, that's a harder thing to teach. Either you have that or you don't; there's not an easy way to spur yourself towards innate curiosity. As Charlie Munger explained in a historical anecdote:

“In advanced human civilization, culture greatly increases the effectiveness of curiosity in advancing knowledge. For instance, Athens (including its colony, Alexandria) developed much math and science out of pure curiosity while the Romans made almost no contribution to either math or science. They instead concentrated their attention on the "practical" engineering of mines, roads, aqueducts, etc. Curiosity, enhanced by the best of modern education (which is by definition a minority part in many places), helps man to prevent or reduce bad consequences arising from other psychological tendencies. The curious are also provided with much fun and wisdom long after formal education has ended.”

Clarity of Terms & Definitions

Every sound idea has some key concepts that will come up over and over again. Some of them can mean different things in different markets, or have different implications to different people. Using the words "interchange," "marketplace," "agentic", "duel-use," "commercialization," "consumption," "engagement," and on and on. All these buzzwords that fill up our lives are shorthands for concepts.

The very best founders build a conceptual framework right in front of you so that you can easily hang different ideas, questions, and information from that framework. Charlie Munger describes a "Latticework of Mental Models" that he uses to keep track of details of a particular idea:

"The first rule is that you can’t really know anything if you just remember isolated facts and try and bang ’em back. If the facts don’t hang together on a latticework of theory, you don’t have them in a usable form. You’ve got to have models in your head. And you’ve got to array your experience, both vicarious and direct, on this latticework of models. You may have noticed students who just try to remember and pound back what is remembered. Well, they fail in school and in life. You’ve got to hang experience on a latticework of models in your head.”

The way exceptional founders operate is they not only build this latticework for themselves that contains a deep well of context, but they can articulate a simplified latticework for their audience. You construct a framework for how to think about an idea; what the problems are, what the dependencies are that keep the problem entrenched, what the insights are that make their solution possible.

In the book, How To Take Smart Notes, it explains the methods of people who consider themselves "memory artists." The way these people operate is explained this way:

"[They] attach meaning to information and connect it to already known networks of connections in a meaningful way. One piece of information can become the cue for another and strings or networks of cues can be built."

This can be a powerful mechanism that anyone can build for themselves. But when a founder (or anyone with an idea they're trying to communicate in pursuit of buy-in) is explaining a concept, they help you jump right into this by presenting you with a fully formed network of connections between different ideas.

The truly exceptional are able to gauge the level of context a particular listener has and adjust accordingly. If you're a complete noob to a space, the presenter is free to offer you a fully-formed network that is born out of their own assumptions, hypotheses, and explorations. But when you interact with someone who has anywhere from a passable to an expert level of understanding, the presenter is also able to take their framework and help anchor it to key concepts that the amateur or expert already has in their own head.

Presentation of Clear & Distinct Ideas

Once the framework has been laid for what assumptions and frameworks you're basing your perspective on, you're ready for the crux of any pitch. The core idea has to be the most memorable aspect of any presentation if you're hoping to demonstrate clarity of thought.

This is why people default to "Uber for X", "Anduril for Y", or "Stripe for Z" types of pitches. Someone else has done the hard work to define a clear and distinct idea that you can piggy back off of.

The worst versions of this are derivative or limiting. You're taking a clear and expansive idea like "Uber" or "Anduril" and you're trimming it down to a more opaque meaning or smaller market. "Ramp for LATAM" or "Anduril for ships" or "Scale AI for marketing" — these are smaller aspects of something that these generational companies could also build already.

The best versions of this, instead, may use an existing framework, maybe even an analogous name, but its not a subset of an existing company's existing market. Its relying on the shorthand to accomplish a goal.

Uber mostly just means marketplace.

Anduril means vertically integrated.

Scale AI means data-enabling.

With the help of that familiar anchor point, the best founders will then jump from that borrowed framework to present a really distinct idea. This is the thing that, if you do your job, investors will walk away from a conversation and when they go to tell their partners about you, they'll say "They're building XYZ." It's the clear, distinct takeaway.

One of the other things that is just as critical as clearly and distinctly articulating what your idea IS, it's just as important to avoid context around what your idea is NOT. This is a function of not being distracted. Rather than a laundry list of directions you maybe COULD go, you're focused on articulating a very deliberate path your beliefs lead you to think that you MUST go.

That Narrative Hook

Finally, the way you've demonstrated your clarity thus far is presenting your hard earned "insight" and assumptions, offering up a framework for them to understand it and follow along, and then clearly articulating the idea in a way they can understand, all without you or them getting distracted.

Then, you conclude by pointing to the "dream the dream." What does this look like in 3, 5, 10 years? This speaks to the scope of your ambition. If you think in 10 to 20 years maybe you could be $100M of revenue, growing low single-digit percentages, and profitable? Good luck with your lifestyle business. Instead, you want to anchor to WHY this is critical. It's almost an incredible realization; "there is $100B of spend that is wasted today and we can address it with XYZ!"

They'll remember that what you do is "XYZ" within your clear and distinct idea. But they'll also remember the reason they should care. It's not just "a network to access ophthalmology," or an "Uber for eye doctors." It's also an opportunity that could save millions of lives each year.

Building a Pitch

This is sort of a rough formula for demonstrating clarity of thought. And you might be thinking, "that's a tall order, but I think I can develop those points over a ~30 minute conversation." But the reality is that, if you've done your job right, that presentation of logic takes ~2-3 minutes at the beginning of the conversation. From there, you take the framework you've offered them and you fill in the details. "How will you sell? What aspects of the product do you need to build? What other features will you need to expand into?"

From those follow up questions, you have to seal the deal on your demonstration of "clarity of thought." Seamlessly tie each question / concept back to the "Latticework" around what you're building so that it reinforces every aspect of the framework above.

Often, when you walk away from these types of meetings, you walk away feeling like the founder has thought of everything. Even the questions that they don't (yet) have answers to, they know those are the critical questions to ask. And it isn't that you have ACTUALLY thought of everything. But its that the clarity of your perspective is so well formulated that any question can be very neatly addressed and hung on the "Latticework" of perspective as an undeniable fact, a provable assumption, or a falsifiable idea. So it SEEMS like every concept fits together so smoothly.

When you're 3-5 days into ideating on something, how can you possibly have this clarity of thought? Evidence can do some of the heavy lifting. Being able to point to early validation can reinforce the quality of your thinking. But I've also seen founders who had an idea IN a conversation with me and can then immediately turn around and riff on that new idea with the clarity expressed above.

Therefore, What?

Across all the characteristics a founder could have, why "clarity of thought?"

Thinking is the lifeblood of everything. Within your own head, you drill into things to better understand them. But clarity of thought is expressed, not internalized.

Like the famous quote:

"If you can't explain it simply, you don't understand it well enough"

Clarity of thought is something that you understand so well that you can articulate it, not just so that anyone can understand you. It's about articulating it in such a way that no one could misunderstand you.

Clarity of thought demonstrates two factors: (1) depth of understanding, and (2) commanding presence. Depth of understanding enables you to talk deeply about a topic without hitting the bottom of your own knowledge well. In terms of presence, when you can explore a concept idea so simply, then it becomes that much easier to attract investors, talent, partners, customers, anyone.

So, when you're failing to deliver a compelling pitch, you have two options: (1) reevaluate the quality of your story and whether its worth telling, and (2) score yourself on your abilities in terms of clarity of thought.

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