How a future president spotted a level playing field—and rewired a country around it.

My guest today is Toomas Hendrik Ilves. A former President of Estonia, he’s widely credited with shaping one of the world’s most ambitious digital societies. But that’s the outcome. We dig into the thinking that led there—the doubts, the decisions, and the moments of clarity that changed not just a country, but how we talk about digital futures. This isn’t nostalgia; it’s a masterclass in starting differently, staying deliberate, and building trust into the system.

What you’ll get:

• Pick the winnable wedge: choose plays where you’re on a global level playing field.

• Design the trust layer: unique digital ID and a distributed exchange—no single honeypot.

• Drive adoption without perfect teachers: seed youth first, co-fund for “skin in the game,” and let social proof do the work.

• Turn geopolitics into sequence and leverage: how criteria-driven EU entry unlocked NATO.

• Govern with AI + law: proactive public services, privacy by design.

Conversation map:

00:00 Why this conversation, why now
03:05 Early sparks: BASIC in 1971, a PDP-8, and learning that “language is irrelevant—programming is thinking”
10:40 Poverty as strategy: spotting the web as Estonia’s level playing field
17:20 Wiring the schools: co-funding, envy, and a generation that learned by doing
25:10 Architecture, not apps: unique IDs, chips, and a distributed exchange layer (no single honeypot)
33:45 Copying Estonia? What travels—and what absolutely shouldn’t
39:20 EU before NATO: controlling the criteria when politics says “no”
46:10 Beyond “transition”: flipping old stereotypes and what the data actually shows
51:00 What’s next: AI in public services, proactive tax/health, and why law must lead
55:10 The resistance playbook: when critics don’t code, start with kids and parents
57:00 Quickfire

On his nightstand: Homer — The Odyssey: A New Translation by Daniel Mendelsohn (Amazon)

The question he leaves us with: Why are we turning away from rational, evidence-based thinking after centuries of progress?

Guest links

X/Twitter: @IlvesToomas
LinkedIn: Toomas Hendrik Ilves

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