Why the Best Investors Read Poetry

I recently asserted that consultants make good founders, and was subsequently asked why. I paused, and a somewhat polished answer came first – they understand the market and frame problems well. But the more I thought about it, the more I realised the real answer is more nuanced: they've seen patterns across industries.

A consultant working on a retail transformation project picks up frameworks that apply to healthcare. A McKinsey associate building a pricing model for airlines learns something useful for SaaS. The domain expertise isn't the point. The cross-pollination is.

This is why I think interdisciplinary thinking is the most underrated edge in investing.

Let me explain.

The Limits of Pattern Recognition

Early-stage investing is about making bets with incomplete information. There's no LBO that tells you whether a founder will figure it out. No sensitivity analysis that captures market timing. You're pattern-matching against everything you've ever learned.

The best investors don't just know their sectors. They pull from everywhere.

Warren Buffett reads five newspapers a day and quotes Benjamin Franklin. Charlie Munger built an entire philosophy around "mental models" borrowed from psychology, physics, and biology. Peter Thiel studied philosophy at Stanford before founding PayPal. Marc Andreessen famously told founders to read history.

None of this is accidental.

When you're evaluating a company doing something genuinely new, sector expertise hits a wall. You can't model the future by extrapolating the past. You need adjacent knowledge to see around corners.

A healthcare investor who's read about regulatory capture in other industries will spot the wedge opportunity faster. A fintech VC who understands behavioural economics won't just evaluate the product – they'll evaluate whether people will actually change their behaviour to use it.

But pattern recognition has a failure mode. It overfits. Founders get evaluated against prior successes. Markets get compared to earlier categories. Ideas get judged by how quickly they can be explained using existing mental models.

This is how genuinely new ideas get missed.

Poetry, literature, and history train a different muscle. They force you to sit with ambiguity. To interpret meaning without collapsing it prematurely. To recognise emotional truth before it can be articulated cleanly.

Those aren't soft skills in venture. They're foundational.

The Pattern Works in Reverse

Stewart Butterfield studied philosophy before building Slack. Patrick Collison was obsessed with programming, economics, and history before Stripe. Brian Chesky trained as an industrial designer, not a hospitality executive.

Airbnb worked because someone with a designer's eye looked at a hospitality problem and asked different questions. Stripe worked because someone who'd thought deeply about developer experience applied it to payments – which incumbents treated as infrastructure rather than product.

When you're building something new, you're not competing on expertise. Everyone has expertise now. You can hire it. The competitive advantage is synthesis – the ability to pull from multiple fields and see connections others miss.

Why I Collect Quotes About Emotions

For years, I've kept a document I call The Emotional Almanac. It's organised by feeling – love, grief, loneliness, anger, joy, shame, and more. Hundreds of quotes from poets, philosophers, novelists, random corners of the internet.

People always ask why.

Part of it is personal. When you're in the middle of something, having words for it helps. Articulating experience creates distance from it; it is everyone's first time living, but others have worn similar shoes in almost all scenarios.

The bigger reason is that if you're going to invest in companies, you're investing in people. Founders specifically. And founders are not spreadsheets. They're humans running on fear, ambition, ego, insecurity, and occasionally joy.

A founder motivated by proving their parents wrong will make different decisions than one motivated by intellectual curiosity. A CEO processing grief will lead differently than one riding a manic high of headlines.

These aren't edge cases. They're the norm. And if you can't read them, you're flying blind.

Someone once told me that half the job in VC is knowing when a founder needs a lawyer recommendation and when they need a therapist. That really stuck with me. The Emotional Almanac is my practice for that. Every quote is a compressed insight about how humans work. I won't remember all of them. But reading them over years changes how I see people.

Living With Uncertainty

One of the hardest parts of venture is sitting with uncertainty for long periods of time.

You make a decision. You commit capital. And then, for years, you don't know whether you were right. Feedback is delayed. Signals conflict. Confidence oscillates.

Most people are uncomfortable with that. They seek resolution. They gravitate toward consensus. They prefer explanations that reduce ambiguity quickly, even if incomplete.

Poetry does the opposite. It rewards patience and resists closure. It allows multiple interpretations to coexist without forcing a conclusion.

I believe that mindset is useful in venture. It makes you less reactive, less dogmatic, and more willing to let a thesis evolve as reality unfolds.

The Practical Case for Liberal Arts

I studied Economics and Politics at Edinburgh. Not computer science, not finance, not anything obviously vocational.

At the time, I wasn't thinking strategically. I was following curiosity. Economics gave me a framework for how systems work. Politics taught me that incentives and institutions matter more than individuals. Together, they trained me to think about second-order effects.

That's useful in VC. When I'm evaluating a company, I'm not just asking whether the product works. I'm asking: what happens when this scales? Who gets disrupted and how will they respond? What regulatory capture might emerge? Where do the economic incentives actually point?

These aren't questions you learn from a financial modelling course. They're questions you learn from thinking about systems.

The liberal arts often get a bad rap in tech circles, but the founders building the most interesting companies often have exactly this background. They learned how to think, not just what to think. That flexibility is the point.

Building the Range

What does this look like in practice?

Reading outside my lane – history, philosophy, fiction – not to become an expert but to build a library of patterns I can draw from later. Writing, even when no one reads it, because writing forces you to clarify what you actually think. And collecting things that resonate. I collect quotes. Other people collect mental models or historical case studies. The specific format matters less than the habit of noticing and storing insight.

The best conversations I've had recently have been with artists, doctors, teachers. Not because they know about venture – because they don't. They see the world differently.

The Real Edge

The venture industry is getting more competitive. More capital chasing deals. More ex-bankers and consultants entering the space. More tools that democratise access to information.

In that world, what's actually scarce?

Not financial modelling skills. Not deal sourcing networks. Not sector expertise.

What's scarce is the ability to see what others don't. To notice a pattern that doesn't fit the spreadsheet. To understand a founder's motivation before they articulate it themselves. To ask questions nobody else thinks to ask because you've read something they haven't.

That's the edge. And it doesn't come from specialisation.

The Emotional Almanac isn't a side project. It's my training.