November 20, 2025

Earnestness as Signal: The People Worth Paying Attention To

Matt Zeigler·article

We finance/business/strategy professionals spend a disproportionate amount of time and energy documenting how narratives get distorted, weaponized, and manipulated. Look at Panoptica and, wahhhhhh. It can almost make you think the world is as ugly and calculating as the ugly calculations are. But meanwhile, the inverse - the people who actually mean what they say - hasn't become any less rare, even if it's nowhere near as newsworthy.

The problem is structural. Headlines live on conflict, contradiction, and collapse. They're built for the grotesque, and often presented in listicles. What a gross word - listicles. But, that's life. Tick-tock to TikTok. And meanwhile, the people who think clearly, act with integrity, and actually mean their commitments? They're too boring for the algorithm. Too quiet for the discourse. They're notes in the margins of "cool person I met at a conference" that we almost never remember to go find a podcast about.

Almost. Not me, at least. And if you're reading this, probably not you, too.

Over the past year, we've been capturing this inverse intentionally. On The Intentional Investor - a show on Epsilon Theory where I sit down with one great strategic thinker at a time - we're not just pulling their origin stories. We're documenting how people in high-stakes worlds managed to stay earnest despite every incentive to become calculation machines.

Rusty Guinn, one of the architects of Epsilon Theory itself, said it as clearly as anyone has:

I think a lot of us in the industry go through cycles of earnestness and cynicism. We open ourselves up. We realize that the world is a rough place for people who are too earnest. And then we fall into cynicism, we crash, we burn, we hopefully figure out a way to return to earnestness.

That's the thread. Not people who never get cynical. People who do, crash hard, and then consciously choose earnestness again. We like those people. We like their clear eyes, their full hearts, their - you get it.


In an attention economy built on narrative capture and performance, earnestness has become a fresh type of competitive advantage. Not because it's trendy, but because stakes and decency never go out of style.

Think about what earnestness does. When Justin Castelli talks about the difference between a goal and a vision, he's not splitting hairs: "A goal is something I'm striving for, hoping happens. A vision is going to happen. I don't choose that unless it's something I know I'm going towards and then it's gonna happen." That's not aspirational language. That's precision. It's someone who only commits to things they're willing to stake their credibility on.

When Jason Buck describes entrepreneurs as risk mitigators rather than risk-takers, he's reframing the entire mythology around business. You don't take the leap because you're reckless. You take the leap because you've already done the unglamorous work of understanding the downside so thoroughly that you can actually survive it - financially and psychologically. That's a different kind of thinking entirely.

When Jared Dillian talks about saying yes to things - about choosing openness even when it costs him critical credibility - he's describing a conscious trade-off: "You can either be critically successful or commercially successful, but you usually can't be both." He chose the latter. Not out of naiveté, but out of a deliberate calculation about what he wanted to leave behind.

And when Grant Williams sits in a stadium with his 85-year-old father - 75 years of going to the same games, the same wooden seats to cheer on Fulham - and he pauses to tell me, "the result doesn't really matter," he's showing you what presence actually looks like. Not performance. Not optimization. Just showing up for something that matters, like a father's lifelong commitment to his son, and vice versa.

These aren't outliers. We found 10 of them, easily. Enough to scratch the surface. Enough to whet your appetite. And many of them, you already know.


Behold The Intentional Investor supercut - a collaboration between Epsilon Theory and Cultish Creative, now available on both channels - pulling from conversations with:

Goal vs. Vision (Justin Castelli

Entrepreneurs as Risk Mitigators (Jason Buck

Mentorship and Gratitude (Jenny Rozelle

Competition on Merits (Perth Tolle

Gap-Fillers (Tyrone Ross

Creative vs. Craft (Pablos Holman

Authenticity (Kris Abdelmessih

Earnestness and Cynicism (Rusty Guinn

Openness (Jared Dillian

Time and Presence (Grant Williams)

The supercut is 20 minutes. It's a taste. The full episodes - detailed personal histories, drawn out through genuine curiosity - those are deeper. Some of these conversations run two hours. They're unrushed. No soundbites. No hot takes. Just people thinking, and a host willing to actually listen.

This format matters. You don't end up in conversations like this by accident or performance. We want to talk to people who still believe that depth and nuance are worth the time - and we want to listen to those conversations, then talk about them more with colleagues, peers, and each other.


Panoptica is always going to be about parsing the stories in which we swim. We accept that headlines will always be built on the most potentially viral stories. The non-headline-worthy people, and their stories, don't deserve to get entirely buried. We just need new ways to help them get told - and new ways to share them with one another.

That's why this collaboration exists. That's why this space is being built. Not to preach about earnestness, but to point at it. To say: these people exist. They think differently. And if you're looking for signal in a noisy world, this is where I found it.

If you want to hear what it sounds like, the full catalogue is out there. Pick a few favorites. Explore. And if you know someone who should hear one of these stories - send them the link. That's the whole idea in practice.

Earnestness used to be assumed. Now it's curated. That shift tells you something about where we are.

 

 

JPR

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