Reflections from Tallinn

There are moments when you find yourself in a room that reminds you just how small the world really is, and just how big its ideas can be. Standing on a stage in Tallinn, Estonia, last week, at the Smart North Summit, was one of those moments.

I was invited to join a panel — moderated by Estonian journalist Johannes Tralla — built around a question I haven't stopped thinking about since: when you're trading (doing business with and partnering) with the US, the Middle East, Africa, or Asia, what beats the bots? What do people know that ChatGPT doesn't?

Why Estonia?

Enterprise Estonia hosted the Summit to bring decision-makers from 14 countries together in one place, with one goal: help Estonian businesses reach beyond their borders. Global leaders in green energy, defense, and ICT sat side by side with Estonian founders and government leaders, sharing what it actually takes to build trade relationships that last.

Have you ever been in a room where you can feel a country's ambition? That was Tallinn for me. This is a nation of roughly 1.3 million people — about a third the size of the Portland metro area — and yet it has produced more tech unicorns per capita than almost anywhere on earth. Estonia isn't waiting for the future of technology and defense innovation to arrive. It's building it.

What Beats the Bots?

Here's where I landed on the panel: AI can model risk, price a tariff shift, and flag a supply chain disruption faster than any of us ever could. What it can't do is sit across a negotiating table in Nairobi, in Riyadh, in Seoul, and know the difference between a "yes" that means "let's keep talking" and a "yes" that means "we have a deal." That instinct — built from years of showing up, listening, and getting it wrong before getting it right — is still entirely human. That's what beats the bots.

A Dinner That Opened My Eyes

One evening, I found myself at a dinner at Tallinn's photography museum with business leaders from 17 different countries. Somewhere between courses, it hit me: a country this size had just brought nearly 20 nations to one table, talking openly about defense tech, green energy, and building a technology-forward government. Size isn't the ceiling people assume it is. Intent, and the courage to invite the world in, matters so much more.

A Region I Understand a Little Better Now

I also left with a much deeper appreciation for the Baltic and Nordic region — how the influence of neighboring powers still shapes how these countries think about sovereignty and self-reliance today. The KGB Museum, tucked right above my hotel, was a quiet, sobering reminder of how recent that history is. It's one thing to read about it. It's another to stand in the room where it happened, then ride the elevator down to a lobby full of founders building the next generation of defense technology.

Looking Ahead

If there's one thing I'm carrying home from Tallinn, it's this: the tools are table stakes now — everyone has access to the same data, the same models, the same automation. What's rare is still the relationship. The trust built over a dinner table. The read on a room that no algorithm can give you.

Thank you to Enterprise Estonia for pulling together an event that did exactly what it set out to do — bring the world a little closer to a small country with an outsized global footprint. 🌍