Get Wonky

Patrick O’Shaughnessy runs one of the largest investing podcasts in the world.

When I ask my friends why they religiously listen to every episode, they say: “There’s nothing else like it on the Internet.” His podcast, Invest Like the Best explores the business world with a level of wonkiness that MBA programs don’t even sniff. Unlike the wonk-free, lowest-common-denominator publications we grew up on, he assumes his listeners are resourceful and hyper-intelligent. As a result, he’s attracted a legion of impressive listeners who’ve become his guests such as Spotify CEO Daniel Ek, Shopify founder Toby Lutke, and Stripe co-founder John Collison.

As the show has grown, the episodes have become wonkier. They now go so far into the details that a causal observer would say: “Nobody’s interested in that.” And yet, the wonkiest episodes tend to be the most popular ones. As Patrick says: “On the internet, the more focused you are, the more wonky and niche you are, the bigger your audience is. I think the internet rewards the edges of distributions, and I just happened to be really interested in one of those edges, which was deep, wonky business and investing discussions.”

Wonky people have an enthusiastic interest in the specialized details of their domain. They ignore the social incentives that shame people for having unique interests. Wonkiness is the opposite of how you’re trained in school, where you’re taught to follow the syllabus and repeat exactly what the teacher said in the exact way they said it.

Wonkiness is an algorithm for fresh ideas. It’s how you liberate yourself from the handcuffs of precedent and in our oversocialized world, it’s increasingly rare. The trick is to nurture it until you have passion without ideology and obsessiveness without dogmatism. Wonkiness is how Prince played with gender, adopted a flamboyant style, and blended rock, soul, R&B, and synth-pop to shatter the unwritten rules of music. It’s why Casey Neistat turned the camera around and started filming himself instead of the world beyond him, even after HBO cancelled his show and people mocked him. 

But once you get wonky, you’ll have a combination of ideas nobody’s ever seen before.

Cover Photo by Christina Kirschnerova on Unsplash

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