Cullen Roche Is An Intentional Investor

He got her sushi, her favorite food, as a surprise. He put it in the freezer to keep it fresh until she came over. It’s raw fish, you know? And then, when she got there and he told her, “I’ve got an amazing dinner for you,” he snuck into the kitchen, got the sushi out of the freezer, popped it in the microwave - to get it all steaming hot, obviously, and then he served her…

And they’re still together. Over 25 years later. Love and laughter have a funny way of going hand in hand. You have to be loyal to your people. You have to be disloyal to bad ideas.

People love to say they can cop to their mistakes. Walk into any public setting and ask a decent human with a remotely weathered forehead. They’ll gladly tell you, “Oh, I’ve made my share of doozies,” but, there’s a difference between copping to the general concept of screwing up and laying your uglies on the table.

I have a theory that markets people are better than average about this. Something about getting beat up, humiliated, and losing money in a business that will never let you forget, “All I know is that I don’t know nothing.” They have a way of copping to stuff like… the first time they got their significant other sushi (even when they’d never had sushi themselves) and just how badly they screwed it up.

So it’s been 25+ years later and our storyteller still shares a life (and 2 daughters) with that same woman, and they’re still laughing at his culinary crime. The doozies and the intellectual honesty and the relationships - it’s the difference between an accidental life and intentional life.

Cullen Roche - in a nutshell – is as unvarnished, authentic, and perpetually curious about how things actually work beneath the surface as they come.

In our conversation for The Intentional Investor on Epsilon Theory, Cullen reminded me that we're all trying to solve unsolvable puzzles, especially with careers in finance and economics. His metaphor has stuck with me, not just because I’m a puzzle guy, but because I’m a sucker for challenges like this too. Cullen said economics is "like trying to understand how a car operates, but then also having to understand that there is an insane person operating that vehicle."

Isn't that just life, though? We desperately want systems to be predictable, yet we're continually surprised when human behavior throws a wrench into our elegant models. Crazy drivers. With all their bad habits.*

Perhaps the most powerful takeaway from Cullen's journey was his intentional stance as a "lone wolf" who occasionally runs with different packs but never fully commits to any single one. In an industry obsessed with credentials and pedigree, he built his reputation through genuine intellectual exploration rather than aligning with a particular school of thought.

"I've just never been married to a specific process," he told me, "because I don't think there is any specific school of thought that always works all the time."

This intellectual independence isn't just refreshing, it’s relatable. To a younger me, 15 years ago with no fancy letters after my name, seeing Cullen in the public discourse without any social signifiers tied to his name either – it was revolutionary. It still is. Especially in a world where most of us instinctively huddle into ideological tribes.

Cullen's approach offers an alternative: what if we stayed curious enough to change our minds when evidence suggests we should? Not to shrug off our people, see, re: his family, his thoughts on loyalty, etc., but ideas ain’t people, you know?

So as you listen to Cullen tell these stories, you’ll really start to get a sense about how he balances his loyalty to his favorite people relative to his disloyalty to ideas that no longer make sense.

You can learn this. It helps if you live this. People will prove why they deserve to be your favorites, or not, just as easily as ideas can come in and out of working for you. The trick is, which comes with experience, is you can give your favorite people a lot more of a loyalty-lead than even the best of your fixed ideas. Balancing these truths takes practice. In his case, with seven siblings and parents who emphasized loyalty above all else throughout his upbringing, Cullen developed the rare confidence to take professional risks, knowing his core community would remain intact regardless of failure or success.

"I've always kind of known that if I fail or get pushed away from this group, it doesn't matter because I've got the group that matters the most," he explained.

There's wisdom here for all of us. Perhaps true freedom to explore ideas comes not from detachment but from having a secure base – whether family, friends, or chosen community – that loves us regardless of our intellectual wanderings.

In a world of financial punditry obsessed with being right, Cullen offers a different approach: "As you get older, all you kind of keep learning is that you know less than you thought you did." Kids help. A career of wild ups and downs help (re: his story of having no income in 2008/2009, followed by making a mint off his blog with advertising deals in the ensuing years, it’s true feast or famine stuff).

And, above all, he keeps reminding us to be loyal to our favorite people, and disloyal to the logic that no longer serves us. He’s got so many stories about how it’s been presented and re-presented to him through his entire arc. Especially in a financial world where we're constantly bombarded with certainties that crumble, finding your pack while maintaining your intellectual independence might be the only sustainable edge left.

Curious to hear more about Cullen's journey from unsophisticated sushi supplier to his eclectic fund managing/financial writing empire? Listen to our full conversation on The Intentional Investor, where we explore all of it, from his big Catholic family upbringings all the way to why building a life at the beach might beat grinding it out on Wall Street after all.

*yes, that’s an Offspring reference.