undefined cover
undefined cover
Toomas Hendrik Ilves: From Borders to Bytes cover
Toomas Hendrik Ilves: From Borders to Bytes cover
Inside Reinvention with Andrew Wrobel

Toomas Hendrik Ilves: From Borders to Bytes

Toomas Hendrik Ilves: From Borders to Bytes

47min |16/09/2025
Play
undefined cover
undefined cover
Toomas Hendrik Ilves: From Borders to Bytes cover
Toomas Hendrik Ilves: From Borders to Bytes cover
Inside Reinvention with Andrew Wrobel

Toomas Hendrik Ilves: From Borders to Bytes

Toomas Hendrik Ilves: From Borders to Bytes

47min |16/09/2025
Play

Description

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

Stay connected

Subscribe to Inside Reinvention.
Follow Andrew Wrobel (website, Linkedin and Instagram) and Reinvantage (website, Linkedin, Instagram) for new episodes, tools, and research.


Hosted by Ausha. See ausha.co/privacy-policy for more information.

Transcription

  • Speaker #0

    This is the one thing where we are on a level playing field. Everything else, we're way behind. Just trying to do things a little differently. I don't know why, but I've always had this thing, let's try it differently, let's try something some different way. It did show me that having learned something like that at an early age was important. Then I used a quarter century later to help digitize my country. You know, if you remain constricted by the rules, you don't come up with new ideas. So much of society, so many governments have abandoned the rational thought, and that's what really shocks me.

  • Speaker #1

    This is Inside Reinvention. I am Andrew Robel, and in this series, I speak with people who have rewritten the rules, sometimes by choice, often by necessity. It's not about starting over, it's about seeing differently, choosing deliberately, and moving forward with clarity. My guest today is Tomas Hendrik Ilves, a former president of Estonia. He is widely credited with shaping one of the world's most ambitious digital societies. But that's the outcome. What I want to understand is the thinking that led there, the doubts, the decisions, and the moments of clarity that shaped not just a country, but the way we think and talk about digital future. This conversation isn't about looking back. It's about how reinvention begins, how it unfolds, and what it continues to demand from us. A very warm welcome to the first episode of Inside Reinvention. Thomas, it's so great to have you here.

  • Speaker #0

    Well, we'll see. The first time, we'll see how it goes.

  • Speaker #1

    Okay, so before we talk about the title, before we talk about the impact, when you were still very, very young... You know, you were trying to imagine your place in the world. Who are you trying to become?

  • Speaker #0

    I don't know if I really did want to become anyone. I was just, I was more involved in just things that interested me rather than having a future goal. From a very early age, I didn't want to know as much as possible about everything. That was kind of the, I don't know. I mean, I was always reading stuff, you know, asking questions and. From an early age, I had, I mean, which was illusory, but I thought I had like a different way of looking at things. Had to write a paper in high school or something. I would come up with a new thesis and people would look at me weird. And then sometimes they'd go, well, anyway, I mean, it was basically just trying to do things a little differently. I don't know why, but I've always had this thing. Let's try it differently. Let's try something some different way. And probably I would say, you know, being self-deprecating, that I didn't think I could do it the way... everyone else was doing it, so I might as well try some other way. I think that's, you know, sort of imposter syndrome or something.

  • Speaker #1

    And do you remember your first job, the one you actually got paid for?

  • Speaker #0

    It's hard to say if it was a job. I did stuff that I got paid for, but it was nothing, nothing much. The only relevant job I would say that I had that, I mean, was not my first, but which showed me something that was really important for my later life. I mean, it was something I learned in college. But when I was 17, 16, 17, I had a brilliant math teacher who was doing her PhD at Columbia Teachers College in education. And her idea was, let's see if we could teach kids to program or code. This was in 1971. And so she did this, had this class of 12 of us, and she taught us basic. which is baby Fortran. I mean, she was still today, but at that time, it was, like I looked it up later, it had only been invented a year earlier. And she went and rented a Teletype machine with a Perfo tape, like a long yellow tape. No one remembers these things, but okay. It was, and then we had a big telephone modem. You take, you know, the old phone, you stick it into the, in there, and then it was connected. It was dial-up. connected to a mainframe computer, basically 50 kilometers or 30 miles away. And then we had a little budget to be able to do stuff. The reason you used the Perfotate was that you would basically test out your programs and write them there. And so I learned the code in BASIC. Well, okay. I mean, it was, I didn't think about it. All the other, the boys in the class, other boys in the class, they're all like tech millionaires today. I never, you know, I didn't do that. But then I went to, when I was an undergraduate, I saw a little ad back in the day when they had three-by-five-inch file cards that said, on the bulletin board, programmer, 10 hours, 10 to 15 hours a week in the site department. I said, oh, I know how to program. So I went there, and then it turned out. It was. Professor had bought, I think, the first commercially available lab computer, which was a PDP-8 put up by DEC, which is long out of business, Digital Equipment Corporation. It had 8K of memory. 8K, that's as much as an empty email today, right? But because it had 8K memory, and I have no recollection of what the processor was at the time, but I had a... program in assembler language, which is hexadecimal. I mean, base 16, zero through nine, A, B, C, D, E, F. But program is program. You just, instead of saying go to or whatever you do right on the higher level language, you just write the numbers in. And I said, wow, I could know program because basically it's the language itself is ultimately irrelevant. So that was what I really learned. I was making minimum wage, which at that That time was, I guess, $2.15 an hour. It was a long time ago. That was an interesting lesson. Otherwise, I mean, I had jobs doing stuff, but I mean, that was kind of meh. It wasn't anything where you had any engagement in a serious way or any real agency, but that at least, I mean, you didn't have much agency there either. I just had to sort of figure out how to program this computer. But it did show me that. having learned something like that at an early age was important, which then I used a quarter century later to help digitize my country, which we can get to later on.

  • Speaker #1

    Yeah. So speaking about that, I mean, you mentioned thinking out of the box or maybe even considering there was no box in the first place. And you mentioned Estonia. So before you became president, you have done some amazing stuff for the country. And we're talking about two different things, right? The first one is the digitalization. And we know that 100% of public services right now in Estonia have been digital for quite some time. But the other thing is having Estonia in the EU, which was not something people envisioned at the time, right?

  • Speaker #0

    Well, the digitalization came first. I mean, basically, it was a result of the extreme poverty of Estonia once it became independent again. It had been independent before World War II. And if you read, you'll find in volume two, the Cambridge economic history of Europe, little bar graph, and then it has GDP per capita of countries in Europe. And there it said Estonia had a slightly higher GDP per capita than Finland. That was in 1938, the last full year before World War II when everything went to hell. In 1939, the Finns were invaded, all this. So 1938 is like the last time to look at the countries. The next time, if you look at the GDP per capita of Estonian Finland in 1992, which was the first full year of our independence on our part, then the GDP of Finland at the time, the nominal GDP per capita nominal was $23,800. So basically $24,000 per person. The GDP per capita. of Estonia was 2,800. So basically, Finns had become in the interim eight and a half times richer. Now, what that meant? Well, I mean, I was invited to become, I had U.S. citizenship, I was working at Radio Free Europe, and then the president of the country after our first democratic election said, look, what are you doing over there? You know, come on, let's go come work and help build up the country. I said, okay. I didn't realize how much I was. What a cut in pay I would take. So I went to Washington. I was the ambassador. And we were so poor that there were times when they wouldn't send money from our country, from Estonia, to pay us. So then we'd live another three weeks on credit cards. And I was like, what do we do? How do we get out of this poverty? And the thing about the two aspects of poverty, which I want to talk about, one is that even the GDP figures per capita don't even say enough. because in the interim, we have not built... highway. We have not built, you know, modern hospitals. The buildings are all falling apart. The basic state of the country is much poorer, even if you eliminate the income differences. So because they've had 50 years of development, which we had not had. And the other problem was take from Zeno's paradox of Achilles and the turtle. One of his paradoxes, but it's, But, you know, it's like when the turtle starts going. then the fastest man in earth in Greek mythology, Achilles, by the time he catches up to where the turtle was, the turtle has moved on. Now, what that means in GDP. per capita or GDP, is that, okay, I mean, if Finland starts off at 24,000 US dollars per capita and they have a miserable year of 1% growth, and Estonia has an incredible 8% growth, which is a phenomenal growth rate, we would still lag more behind than we were before. So this is the fundamental problem of development. At home here in Estonia, where I am right now, there were all kinds of theories about what we should do. And so they were like the left, the hard left. They said we should just keep on with communism. And then you had the hard right saying, oh, we should become Singapore. And it was all basic sort of classic economic theory. I saw it differently, though. I mean, first of all, I was just as lost. And I was going, you know, it showed up when you couldn't pay any for anything. because I've been a geek. Because I learned to code when I was 17. And then people knew that and they'd known me. I dealt with this stuff, played around with it even before anything real happened. I bought my first Apple IIe in 1983 or something. So I played around. People thought I was a little weird. So a friend of mine sent me an email. And I was one of the few people who had emails even then. But I said, OK. And he sent me an email and said, look, check. this thing out. And what he told me to check out was Mosaic, which is the first ever web browser invented by Mark Andreessen, who was then a graduate student at Champaign-Urbana, University of Illinois, Champaign-Urbana. And the reason why a web browser was important was that even though Tim Berners-Lee invented... the hypertext transfer protocol or HTTP in 1989, it was not usable because if you know, if you look at your usual URL, it's just like a long string, alphabetical string of figures and numbers. But here, this was, if you put in the New York times, it would bring you to the New York times, but I didn't know that yet. So it seems he was a friend of mine. I said, go buy this and see what you think. And then, so I, back then I went to RadioShack, which is also out of business now along with that. And I bought... for, I don't know, $29.95, this like cardboard thing with seven floppy disks. It was just, I remember it was just big because, you know, they thought people would steal it or something. So I bought this seven floppy disks. You upload it, you know, and these days you download, for free, you download these amazing browsers. But, you know, then, and I upload, so I got this web browser and then I sort of see what it does. And I go, this is the one thing. where we are on a level playing field. Everything else, we're way behind. Roads, hospitals, telecommunications, everything, we're way behind. This is one area where, and then I looked at the numbers, basically, I mean, no one had anything. I mean, the U.S. was sort of in the lead, but in terms of the statistics you had then were actually a number of websites. But it was like everyone was behind. So the first thing I said, okay, what we got to do, if we really want to win, we got to pick a thing where we are on a level playing field with everyone else. And then I said, okay, how are we going to do that? And I figured the country's full of sticks in the mud. And they're like, what are you talking about? This is crazy. No way. Which was, in fact, the case. The other thing that, you know, I brought in this other knowledge, which was basically there had been in my country in the 1920s, this huge. language reform and and the way it was done which had we had got all these new words changed the old grammar did all this stuff and the way it was done was that there was this genius who was the sort of the guy who created these new terms to deal with the modern era he just made the book the elementary school text that all kids had to learn with a little thing in there saying if your teacher tells you otherwise don't listen to him but anyway so what happened was that 20 years after Afterwards, all the old words were forgotten, and the new words were what everyone thought were always being used. I said, this is what we got to do. We get the young people. And so I said, okay, what we should do is put computers, computer banks in every school. And on top of that, the government doesn't pay for all of them. Because another thing I once read somewhere, anyway, basically, you have to have skin in the game. There's a great example from like... Forty years ago, when the first computer games came out, then some sort of experimental psychologists realized that the skills involved in computer games were the same ones that were very, that translated into fighter pilots' skills. So then they put all these computer games in fighter pilots' barracks, and they just gathered dust. So then the Air Force went to some consulting company and said, what do we do? They said, oh, very simple. Just put a little slot in there and make them pay a quarter. And as soon as they did that, all the fighter pilots were lining up to be able to play the game. Because as long as it's free, it's like, ah, you know, who cares? So when I said, okay, how do we do this? I said, I explained to the government what we do is municipal governments, because that's the level of education here. They, you know, your town or village pays for, you know, for deal, I guess, the budget to deal with education. I said half for anyone who wants it. Well, the government pay for half. You kind of come up with the other half. So in the beginning, like there are four or five schools with some, you know, young, bright math teachers that we got to do this. And then the other wonderful motivator. as I predicted, the motivator of human behavior, envy kicked in. And so if you have a little township here, like, you know, it's got like 5,000 people in it, then they have like, you have the ones around it. And so what happened was the one would get it, and then all the other people around would say, how come they have that? We don't. Which they would then go to their board of education and say, we want that thing that they have there. What that meant was, I mean, the program took me from 93 to 95. to convince the government. And at those years, I was like, I mean, basically the Teachers Union newspaper did not, I mean, which is a weekly, did not, there was not an issue that did not attack me for one way or another from this idea as being completely stupid, ridiculous, the enemy of the culture, all this crap. Anyway, so we got the government to do it in 96. By the end of 98, 99, night. All Estonian schools were digital. If you fast forward from that 20 years, I was in my last year of my presidency, and I always go to startups, you know, just to pat them on the head and say, you're great. This is wonderful. And I started asking them, how did you get into this? Why are you doing this? You know, whatever you're doing, you're a startup. And I started counting them up. Basically, 80% of the time of these startups, people would say. oh, I was a kid in your program. So now they were like, you know, 32, 35. They've been coding for 20 years. So that's part of my explanation for why Estonia has the highest number of unicorns per capita, which we have one for every 133 people, 133,000 people in the country. I think Israel's number two. They're like one unicorn for every, I don't know. 800,000. But anyway, just the per capita, the highest number of unicorns and everyone. I mean, all of that's how we later on, once this thing started really going and that became like a thing and people, the government started trying sort of elementary digitization long before anyone else. The banks came up with electronic banking, which was better than anyone else's in the area. I mean, they ended up being taken by, you know, Swedish. banks to come and do theirs. And then what happened basically, and this is where it goes beyond me. I mean, I kickstarted it, but the much smarter people than I am figured out that if you really want to do digitization properly, you need to have a secure, unique identity for every person. You need to have a secure architecture. And then what came out of that is what we have in Estonia today, which is probably the most, I mean, with possible, you know, with maybe competing with Singapore, the most digitized government and public services anywhere. Even that, I mean, I guess the Estonian sort of approach that was kind of similar to what I did, I mean, sort of mentally, which was that they thought of the system we have as now it's been taken over by about 25 countries, more or less, to varying degrees. The thing that was unique, and this we can talk about later on when it comes to AI, is that we only invented one small part of that. All the rest existed. In fact, the unique identity part had existed for 25 years, since 1975, which was a chip card, which would allow you to do two-factor authentication, which is now common everywhere. I mean, all credit cards today, even in the US, chip. But back then, no one ever heard of it. Now, the thing is that you take something that's been around, a chip card or a chip in a car, basically, and you use it in a completely different way. And it provides you with something that no one else has. And so, too, with the architecture, which was invented locally, but it was invented by these kids in the university. I mean, they're 20-year-olds. And they said, OK. What we really need is a distributed data exchange layer so we have, you know, we don't have a single database anywhere that it can be hacked. You know, the worst case of that is the... OPM or Office of Personal Management hack in the US where they stuck everything in one place and everything was sucked out. Whereas in my country, all the data is individual. I mean, sort of my, here I have my driver's record, here's my health record, here's someone else's health record, here's someone else. So basically, the worst that can happen if someone breaks into the system, if they manage, is to get one cell, which would be, say, my... my health record you know even that would be bad but the point is it's not like when you someone hacks into the u.s government master file of all federal employees and you find you get things such as the you know the psychological profiles of cia officers and the home addresses of fbi agents i mean all the stuff that was just stolen because it's all dumped into one so that was the beginning of the that digitization program but you know so basically for you I would say what lessons learned one is have a broad range of experiences and readings so you can put things together and then use it in a different way.

  • Speaker #1

    I want to ask you about that resistance because you mentioned the teachers union paper that would criticize you every single week. What would be your advice that you'd share with leaders who actually have some brilliant ideas so that at least they think that they can do something differently and they need. to convince the crowd or the masses, really? Because, you know, you won't get too far if you don't get them on board.

  • Speaker #0

    Well, basically, the reason they attacked me was precisely because it was the reason I knew they would. Because the teachers, the math teachers, or the teachers didn't know how to program. And that's why I wanted to get the kids. Because if I get the kids, the kids will do it on their own anyway. They don't have to have a competent teacher. We know from, you know, from... years and years of experience. You give a kid a computer, okay, he may break it, but most likely he's going to figure it out much faster than older people. I mean, that's why I wanted to start young, so that I knew that, you know, I mean, basically, you know, educational reform to have an effect takes 15 to 20 years. I figured 15, 20 years, it's fine. Give them the computer now, and we'll see that, you know, there weren't enough qualified teachers to actually teach programming. The kids learn themselves. I mean, that was what I thought. That was what I hoped. And that's what happened. But the opposition was strong. Yeah. But well, basically, because of social pressure from parents saying, you know, we want our kids to have this, the opposition among other groups was lessened because the parents are the voters.

  • Speaker #1

    So the other large area you also had a role in is obviously the EU accession process. And that's a completely different story. It seems Estonia wasn't particularly interested in joining the European Union, right?

  • Speaker #0

    Well, Estonia itself was not interested, and most of Europe did not consider us a country that would ever join. And it was, you know, former Soviet Republic, blah, blah, blah. And the reason what Estonians didn't want to do is because they, because of our historical experience, experience getting invaded by the Soviets, invaded by the Nazis, invaded by again by the Soviets, and then 50 years of Soviet occupation was, we have to get into NATO. We have to get into NATO, NATO, NATO, NATO. And this was the attitude among basically all Eastern European countries. But there was a hope for Poland and the Czechs and the Hungarians that they could also join the EU. I mean, those countries also wanted only to get into... into NATO and all the other stuff, Moon cares. And Eastern Europeans were kind of anti-EU back then, kind of like, we don't need that socialist stuff or, I mean, whatever. On top of that, it became clear that certain countries, Germany first and foremost, were completely against our ever joining the EU even. So I thought about this. I was at the time, I was the ambassador in the United States. And I kept I kept getting these messages saying, forget it, forget it. You'll never get either one, especially not NATO. And then trying to figure out what do we do? I said, well, the problem with NATO, joining NATO, it is a strictly political decision. And so even if you could, you know, I could sort of schmooze the U.S. government to say, okay, we support you. I mean, because there were sympathetic people there, but, you know, they're still like, nah. But the opposition of... basically the large EU countries, I mean, Germany, first and foremost, France, Italy, UK at the time they were in the EU. I mean, in NATO, they would never let us in. But that's a political decision. Now, the EU, on the other hand, the decision as to whether, especially given the sort of the approach the EU took was, it was not political. It was, you have to meet certain criteria. They're very strict criteria. They're difficult criteria to meet. But I said, okay, we can do that. That's something we have agency in. We cannot change the political attitude regarding NATO. But we can change the attitude towards us based on our performance. There was some crisis in the Estonian government, and so I was appointed foreign minister. So since I'd been pushing this line, I said, okay, now we do this. The first meeting we had with the leadership of the foreign ministry was, I knew everyone, basically, you know, 15 people, different departments. And there was one person I didn't know. And it was this very young woman, I don't know, 23, 24. And I said, I don't know you. Who are you? And she goes, tell me your name. And I said, and what do you do? And I said, well, I run the European Integration Bureau. And I said, oh, how big is that? She said, I am the European Integration Bureau, which showed what the... foreign ministry's attitude towards joining the EU was. So I just completely changed that. I said, okay, we redo the budget. We don't have embassies. And like at that time, there are 12 countries in the EU. We opened all new embassies. We completely redid the whole approach to legislation, prioritizing which legislation gets done. Mirabile dicto. In 1997, when they came to decide who qualified, they chose six countries, and we were one of them, because our performance was like that. Now, I mean, that was just like, not in the cards that this would happen. But I mean, if you just push it and you do something that was weird, people came along and did it. Now, our two southern neighbors, Latvia and Lithuania, didn't have that kind of approach. Called me crazy. He said, you know, El-Wislam's on the EU. Why is he doing that? It's only in NATO that matters. But as it happened, I mean, the whole point of joining the EU, ultimately, and that was my nasty thought behind my mind, is that if we can get into the European Union, the other EU members in NATO can no longer veto us. So that basically eliminated all possible vetoes from the UK, Germany, France, Italy, and it basically left... three countries to convince. Turkey, Norway, well four, Iceland, not a problem, and the US. So if you get Canada, right, Canada, Norway, US, Iceland, and Turkey. Now, if those you get on board, you're it. And that's how we got into NATO. I mean, that was, again, it was something that the foreign ministry, when I became foreign minister, basically, as with the computers, it's crazy, This is stupid. This is not important, but I was foreign minister, so they didn't have any choice. So anyway, those are, I guess, the things that counted.

  • Speaker #1

    When I'm listening to these stories, I'm thinking that when a country wants to redefine itself, it really starts with clarity and intentionality. When was that moment when Estonia sort of stopped describing itself as a country in transition and began thinking in terms of designing the future? This is exactly where we are going. Do you remember that moment?

  • Speaker #0

    It happened in different parts of society at different times, I mean, different ministries. There were some that were very sort of forward-leaning, even resentful of this idea of transition. Today, you know, there's a yearly report that comes out, Nations in Transition, which is only about Eastern Europe. You know, I look at this, Estonia is like number two in the world in press freedom, number five in the world in social support for families. It's the only East European country that has legalized gay marriage. I mean, it is less corrupt than most of the EU. So And then I was like, what do you mean nations? Why don't you do a little transition for some of these other countries, right? Yeah, I mean, look at this. Estonia is number two in press freedom. You know what the U.S. is today? 57. I mean, it's like, come on. This whole idea of former Soviet republicans, like, that's a third of a century ago. We have completely changed. I don't want to hear it. So, I mean, the transition part. I mean, I started bugging me a lot earlier just because I would follow the statistics on who's where doing what. Then you look at these numbers and you go, you know, we're not there. I mean, we're not like those countries we should be transitioning to because we're better than they are. And that was kind of always annoying. Some of the problem was, I mean, they had to convince countries to do things like, well, we should we give you visa free travel to Europe? You know, what? So, I mean, all of that... As I said, it's changed dramatically, but it is, it's still, there is an attitude about Eastern Europe is like, oh, listen. Whereas, in fact, it's cleaner, less corrupt, better educated than most of Western Europe today. In fact, in non-Asian countries, that is outside Japan, Korea, Singapore, China, Taiwan. We have the best scores on math and language skills on the OECD PISA test, right? So our educational system is rather good, if that's the case, right? So all of that just shows that, you know, old stereotypes die hard. And I think if you ask, when did this whole idea of transition end? I think it ended with slowly realizing that in whatever your area is, you're actually at least as good, if not better. than the people who are sort of calling you a transitional venture.

  • Speaker #1

    So if you think about reinvention and transformation, it's really an ongoing process. It's not a one-off project. So when you think about Estonia, how do you think the country should or perhaps could reinvent itself right now?

  • Speaker #0

    And when I think about the direction things are going in, we have the big challenge is what happens to this little country in the era of AI? You know, we're small, right? I mean, we don't have that many people. How are we going to, I mean, we'll never be able to compete with the U.S. or China on this. On the other hand, being creative in using AI, you can do all kinds of stuff. One of the stories I tell a lot about is after I was president, I was invited to Stanford University because it was the center of IT in the world. So I go there. I mean, Stanford's very nice. I had to register my kid to go to school there. The way I did it, I had to take my electricity bill. I had to drive down to the headquarters of the school education department. I had to take a number to go in. I had to present my passport. I mean, 17 different documents all on paper. When I finally got to the person behind the desk, she took all the stack of papers, went over and photocopied them all. And then she came back, gave me the stuff back. And then... By hand, she started filling out, you know, whatever, from the photocopies, she started filling out these forms. I was kind of like, you know, Estonia, none of that happens. None of that, right? I mean, it's like, where do you live? We know where, I mean, you know, we know where you live. You get, because you're registered to live there and because it's Everest's birth and whenever you get, when the kid turns a certain age, you get a little email that says. By the way, September 1, school starts, and here's, you know, we give a little school supplies. Are the kids vaccinated? Medical records all exist. They're online. They can check to see. They can't see who you are, but they can see if you say, is this person vaccinated with the required vaccine? All of that's done. You know, this came up with my oldest son who came to the U.S. during COVID. And he got, he was there just for two weeks, but he got vaccinated. and you you came back and it is the yellow card. Here in Estonia, we had, in fact, Estonia was an Estonian company invented the app that is used all over Europe to show that you have been vaccinated because it checks. whether you are or not, without actually accessing your name and data, it just reports back saying, this person is vaccinated. And so he came back and he said, well, all right. And here he went to the doctor. Here, here's my little, my little card was filled out by hand saying vaccinated. What do I do with this? I mean, you know, you're not in the computer. So clearly in the United States, yeah, another example. It was only, I think in 2013, the U.S. military started using chips for two-factor authentication. I mean, we've been doing it for 13 years or so. And to this day, the US government, despite Doge, which is not what you have to know, Doge is not the way to do it. I mean, it's my son, my oldest son, who is now 37. Actually, because he grew up in this insane family, he was always like Anil Ander. Well, he eventually, he ended up being the CIO of the country. Well, he doesn't. published a paper for a German think tank. It's in English, but it's a German think tank, basically showing all of the issues you have to deal with in order to digitize or to use AI in a way that respects rights and freedoms and reform government. None of those are in Doge. No one thought they just went and just chopped things up as opposed to thinking it through. I mean, even the original. pre-AI period, it took us about three or four years to figure out all the legal connections that you have to make. I mean, who can see what? What kind of level of permission does a government official have to see something? Because certain things, you know, public health, you have to see something. People shouldn't be able to see your healthcare records. But on the other hand, in terms of, you know, if there's an epidemic or something, all these very difficult to find questions that must be defined by law. not you don't go in there with an axe and start cutting with and call yourself big balls what do you think estonia will sort of pivot what's next for estonia well i think that the way it'd be given the level of thinking here i think we probably will be one of the thought leaders on a use of ai in public services and that's one place where i think it could be most useful. All the other stuff. It could be a lot of fun and even all kinds of stuff. But as long as the citizen has to face traditional, usually undigitized, but even if slightly digitized government, I mean, what do I do? I want to get a fishing license. Well, I don't know. What do I do? I mean, I have to go get, I mean, I have to do something, whatever it is. I mean, we have part of this already working here since like 2000, which when I do my taxes, I get all my, I get my tax, they're filled out for me. everything's filled out everything i made everything all my charitable donations everything is in there and i did this we're sat there on the screen and you can check it all through and say is this right and it's always right it's always been and then you just press enter and your taxes are done right i mean so i mean the kinds of thing that to me we can foresee in the future is I mean, AI working out for companies. I mean, to think of government. as a service that government. So instead of going after a company that is, it hasn't paid its taxes because it's been, it's been in trouble. Instead, the AI will say, you know, your tax risk, your receipt, I mean, your income is not really meeting what your expenditures are and your loan obligations. And then maybe, maybe you should come and talk. to us, maybe we'll, you know, lighten your tax load so you get over this problem that you may not even know you have because, well, we do have sort of online reporting of all income and expenditures here. So we don't, I mean, we do quarterly reports if you want, but basically you can sign up and just everything happens digitally. So that information is there. It just could be sort of operationalized so that the tax department says, by the way, you know, doesn't look so good. Maybe we need to restructure your tax obligations and, you know, I mean, all these things that governments can do. Governments, I mean, sort of same thing with health care monitoring. I mean, if it's that it can notice, I mean, there's so many things that can notice it depending on how much you want to monitor. Right. I mean, there are ways of monitoring, constantly monitoring your level of health, your blood pressure, all these things can be done. And the AI will say... By the way, here, why don't you come in for something? That's where I see it going because, I mean, you're going to get amazing products from all kinds of huge companies whose yearly income is like a thousand times the GDP of my country. So I'm not worried about that. But it's the application side. And it's also my own experience with the level of application of the old digital revolution in other countries, which was none of it. really in public services. And it's especially true in the United States where, I mean, it doesn't really, you can't, the difference between what you can do, the amazing things that you can do with this here, compared to what private companies, compared to what I can do with in my country on here for whatever, filling out, I mean, applying for something, getting whatever. I mean, I can do it all night. Certainly, we've gotten to the point where the, until this year, there was only one thing you couldn't do online, which was get divorced. As of January 1, you can even get divorced online.

  • Speaker #1

    So I publish a weekly column that is focused on various aspects of reinvention. And I share articles that. discuss various topics and I ask questions. And there was one article from the Wall Street Journal recently saying that some AI models are already rewriting their own shutdown code. And this is because we're not teaching AI to think like us. We're teaching it to win. So my question was, what else are we handing over to machines that haven't truly understood what we meant, but will follow anyway? What are your thoughts about such trends and dangers that we're perhaps not seeing.

  • Speaker #0

    Well, what I have followed is this whole idea which has gone out of the United States in the last five months, which is that you collect all this data and put it into one place, which is something we specifically designed our system to compartmentalize everything. Now, aside from the security risks, I mean, you can actually, once you apply AI to these data, you can start finding out things that you probably wouldn't want to. You wouldn't want the government to know. And that's my worry is that, okay, the government then has a tool. I mean, especially because there's no legal basis for any of this. There's no law allowing the U.S. government to do what it just did in the past five months. In this country, you know, anything that changes the way anyone can look at data requires that legal foundation. And, you know, sort of going through the whole process, does this violate basic fundamental rights and privacy rights? Which makes it, you know, slower. On the other hand, we do it, which makes us feel a lot much safer.

  • Speaker #1

    So I want to go back to you now towards the end of the conversation. You've worked across a number of different identities. You were a journalist, diplomat, president, now a thought leader, an educator. How has your definition of reinvention or transformation changed across these roles?

  • Speaker #0

    Well, I don't know. I mean, basically every position I've been in, I've had some weird ideas and done things differently. It's always been like that, basically. I don't know. When I was at Radio Free Europe, I was head of the Estonian service. And then it was like 1988. And everyone was saying, oh, Glasnost perestroika. I was like 36 years old. No, I was like 34 years old. Yeah, 34 years old. I was head of the Estonian Serbs. I said, oh, well, how about I go visit the Estonian part of the Soviet Union? Now, I mean, for that, I mean, it was like, nope. The only people that ever got from Radio Free Europe to the Soviet Union were people who re-defected. So, but I said, you know, we should call them on their bluff. And then I went to my leadership, went up to Washington, you know, this crazy guy who wants to go to visit Estonia. And it took them like three months, right? I said, okay, you can try, but they won't let you in, right? Well, anyway, so as they said, okay, then I wrote to the so-called foreign minister of Estonia saying, by the way, in the spirit of Lasnost and Perestroika, you know, I say it's all open and free speech, and how about if you let me in? I mean, I like to visit. It's like, no, three months go by, you know, and then finally I get this notice. It's like, yeah, you can come. But then I went, I was in Munich. I went to the Soviet consulate there. They refused to give it to me. So I called them up. I said, what do you do? They said, well, I'll tell you what you do. Fly into Finland. And then you call this number. So, I mean, people were thinking out of the box in Estonia, too. This guy's KGB basically telling me, he says, call this number. And you meet this guy and give him your papers. And by the way, if he gets it done, give him a bottle of Western cognac. So that's what I did. I mean, I flew to Finland not knowing if I was going to get in. But I called up the guy and I gave him my papers and I got my visa and I gave him a bottle of Hennessy. It worked. But basically, you have to be, you know, if you remain constricted by the rules. You don't come up with new ideas, that's all. I mean, it just seemed like no one else had ready for your book. Oh, with Blasphemer's Perestroika, why don't we try this? It was just, I thought, well, it's kind of nuts, you know.

  • Speaker #1

    Okay, so what book is currently sitting on your bedside table?

  • Speaker #0

    New Mendelssohn translation of The Odyssey.

  • Speaker #1

    And I want to ask you before we close, if you could ask one deep, unsettling question of yourself, of leaders of the next generation, what would that be? What is the question that is still sort of challenging you specifically?

  • Speaker #0

    Oh, there's so many, I don't know. There's no single one. I mean, I would get... I was like, you know, what's your favorite color? Like, I don't know, one question. Well, I guess what I think about the most question, what I think about most is why is it after the complete victory of the Enlightenment and bettering, pulling us out of the Middle Ages and made a rational thought, scientific evidence, have we descended back into this sort of Again, I would say medieval conspiracy theory, rumor-based insanity that we see. And it's just so bizarre because, you know, you would never get this without the science that came out of the Enlightenment. But, well, they're the same thing. I remember reading, you know, 40 years ago, V.S. Naipaul's Among the Believers, you know, and you have this, like, total turn of Iran towards sort of medieval belief. Yet they all had modern weapons. I don't know how we got there that we've given up. So much of society, so many governments have abandoned the rational thought that from the 18th century on, well, maybe earlier, from the Renaissance on to through the Reformation and the Enlightenment, have brought us to a level of wealth, well-being, prosperity that was never, ever imagined. Thomas Hobbes said the life of a primitive man was nasty, brutish, and short. Well, I mean, how it stopped being nasty, brutish, and short was through science, evidence, rules, you know, all that. And yet we're turning against it. And that's what really shocks me.

  • Speaker #1

    Thomas, thank you so much for the conversation. I really enjoyed it. And I'm looking forward to meeting you in person.

  • Speaker #0

    Great. Well. If you're ever in Estonia, I would recommend doing it in the summer. All right. Great.

  • Speaker #1

    Thanks for joining me today. If today's story left you with a question or a quiet nudge, leave a comment or share the episode. Subscribe if you'd like to keep on listening. And remember, the next chapter doesn't always begin with a plan. Sometimes it starts with a pause.

Description

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

Stay connected

Subscribe to Inside Reinvention.
Follow Andrew Wrobel (website, Linkedin and Instagram) and Reinvantage (website, Linkedin, Instagram) for new episodes, tools, and research.


Hosted by Ausha. See ausha.co/privacy-policy for more information.

Transcription

  • Speaker #0

    This is the one thing where we are on a level playing field. Everything else, we're way behind. Just trying to do things a little differently. I don't know why, but I've always had this thing, let's try it differently, let's try something some different way. It did show me that having learned something like that at an early age was important. Then I used a quarter century later to help digitize my country. You know, if you remain constricted by the rules, you don't come up with new ideas. So much of society, so many governments have abandoned the rational thought, and that's what really shocks me.

  • Speaker #1

    This is Inside Reinvention. I am Andrew Robel, and in this series, I speak with people who have rewritten the rules, sometimes by choice, often by necessity. It's not about starting over, it's about seeing differently, choosing deliberately, and moving forward with clarity. My guest today is Tomas Hendrik Ilves, a former president of Estonia. He is widely credited with shaping one of the world's most ambitious digital societies. But that's the outcome. What I want to understand is the thinking that led there, the doubts, the decisions, and the moments of clarity that shaped not just a country, but the way we think and talk about digital future. This conversation isn't about looking back. It's about how reinvention begins, how it unfolds, and what it continues to demand from us. A very warm welcome to the first episode of Inside Reinvention. Thomas, it's so great to have you here.

  • Speaker #0

    Well, we'll see. The first time, we'll see how it goes.

  • Speaker #1

    Okay, so before we talk about the title, before we talk about the impact, when you were still very, very young... You know, you were trying to imagine your place in the world. Who are you trying to become?

  • Speaker #0

    I don't know if I really did want to become anyone. I was just, I was more involved in just things that interested me rather than having a future goal. From a very early age, I didn't want to know as much as possible about everything. That was kind of the, I don't know. I mean, I was always reading stuff, you know, asking questions and. From an early age, I had, I mean, which was illusory, but I thought I had like a different way of looking at things. Had to write a paper in high school or something. I would come up with a new thesis and people would look at me weird. And then sometimes they'd go, well, anyway, I mean, it was basically just trying to do things a little differently. I don't know why, but I've always had this thing. Let's try it differently. Let's try something some different way. And probably I would say, you know, being self-deprecating, that I didn't think I could do it the way... everyone else was doing it, so I might as well try some other way. I think that's, you know, sort of imposter syndrome or something.

  • Speaker #1

    And do you remember your first job, the one you actually got paid for?

  • Speaker #0

    It's hard to say if it was a job. I did stuff that I got paid for, but it was nothing, nothing much. The only relevant job I would say that I had that, I mean, was not my first, but which showed me something that was really important for my later life. I mean, it was something I learned in college. But when I was 17, 16, 17, I had a brilliant math teacher who was doing her PhD at Columbia Teachers College in education. And her idea was, let's see if we could teach kids to program or code. This was in 1971. And so she did this, had this class of 12 of us, and she taught us basic. which is baby Fortran. I mean, she was still today, but at that time, it was, like I looked it up later, it had only been invented a year earlier. And she went and rented a Teletype machine with a Perfo tape, like a long yellow tape. No one remembers these things, but okay. It was, and then we had a big telephone modem. You take, you know, the old phone, you stick it into the, in there, and then it was connected. It was dial-up. connected to a mainframe computer, basically 50 kilometers or 30 miles away. And then we had a little budget to be able to do stuff. The reason you used the Perfotate was that you would basically test out your programs and write them there. And so I learned the code in BASIC. Well, okay. I mean, it was, I didn't think about it. All the other, the boys in the class, other boys in the class, they're all like tech millionaires today. I never, you know, I didn't do that. But then I went to, when I was an undergraduate, I saw a little ad back in the day when they had three-by-five-inch file cards that said, on the bulletin board, programmer, 10 hours, 10 to 15 hours a week in the site department. I said, oh, I know how to program. So I went there, and then it turned out. It was. Professor had bought, I think, the first commercially available lab computer, which was a PDP-8 put up by DEC, which is long out of business, Digital Equipment Corporation. It had 8K of memory. 8K, that's as much as an empty email today, right? But because it had 8K memory, and I have no recollection of what the processor was at the time, but I had a... program in assembler language, which is hexadecimal. I mean, base 16, zero through nine, A, B, C, D, E, F. But program is program. You just, instead of saying go to or whatever you do right on the higher level language, you just write the numbers in. And I said, wow, I could know program because basically it's the language itself is ultimately irrelevant. So that was what I really learned. I was making minimum wage, which at that That time was, I guess, $2.15 an hour. It was a long time ago. That was an interesting lesson. Otherwise, I mean, I had jobs doing stuff, but I mean, that was kind of meh. It wasn't anything where you had any engagement in a serious way or any real agency, but that at least, I mean, you didn't have much agency there either. I just had to sort of figure out how to program this computer. But it did show me that. having learned something like that at an early age was important, which then I used a quarter century later to help digitize my country, which we can get to later on.

  • Speaker #1

    Yeah. So speaking about that, I mean, you mentioned thinking out of the box or maybe even considering there was no box in the first place. And you mentioned Estonia. So before you became president, you have done some amazing stuff for the country. And we're talking about two different things, right? The first one is the digitalization. And we know that 100% of public services right now in Estonia have been digital for quite some time. But the other thing is having Estonia in the EU, which was not something people envisioned at the time, right?

  • Speaker #0

    Well, the digitalization came first. I mean, basically, it was a result of the extreme poverty of Estonia once it became independent again. It had been independent before World War II. And if you read, you'll find in volume two, the Cambridge economic history of Europe, little bar graph, and then it has GDP per capita of countries in Europe. And there it said Estonia had a slightly higher GDP per capita than Finland. That was in 1938, the last full year before World War II when everything went to hell. In 1939, the Finns were invaded, all this. So 1938 is like the last time to look at the countries. The next time, if you look at the GDP per capita of Estonian Finland in 1992, which was the first full year of our independence on our part, then the GDP of Finland at the time, the nominal GDP per capita nominal was $23,800. So basically $24,000 per person. The GDP per capita. of Estonia was 2,800. So basically, Finns had become in the interim eight and a half times richer. Now, what that meant? Well, I mean, I was invited to become, I had U.S. citizenship, I was working at Radio Free Europe, and then the president of the country after our first democratic election said, look, what are you doing over there? You know, come on, let's go come work and help build up the country. I said, okay. I didn't realize how much I was. What a cut in pay I would take. So I went to Washington. I was the ambassador. And we were so poor that there were times when they wouldn't send money from our country, from Estonia, to pay us. So then we'd live another three weeks on credit cards. And I was like, what do we do? How do we get out of this poverty? And the thing about the two aspects of poverty, which I want to talk about, one is that even the GDP figures per capita don't even say enough. because in the interim, we have not built... highway. We have not built, you know, modern hospitals. The buildings are all falling apart. The basic state of the country is much poorer, even if you eliminate the income differences. So because they've had 50 years of development, which we had not had. And the other problem was take from Zeno's paradox of Achilles and the turtle. One of his paradoxes, but it's, But, you know, it's like when the turtle starts going. then the fastest man in earth in Greek mythology, Achilles, by the time he catches up to where the turtle was, the turtle has moved on. Now, what that means in GDP. per capita or GDP, is that, okay, I mean, if Finland starts off at 24,000 US dollars per capita and they have a miserable year of 1% growth, and Estonia has an incredible 8% growth, which is a phenomenal growth rate, we would still lag more behind than we were before. So this is the fundamental problem of development. At home here in Estonia, where I am right now, there were all kinds of theories about what we should do. And so they were like the left, the hard left. They said we should just keep on with communism. And then you had the hard right saying, oh, we should become Singapore. And it was all basic sort of classic economic theory. I saw it differently, though. I mean, first of all, I was just as lost. And I was going, you know, it showed up when you couldn't pay any for anything. because I've been a geek. Because I learned to code when I was 17. And then people knew that and they'd known me. I dealt with this stuff, played around with it even before anything real happened. I bought my first Apple IIe in 1983 or something. So I played around. People thought I was a little weird. So a friend of mine sent me an email. And I was one of the few people who had emails even then. But I said, OK. And he sent me an email and said, look, check. this thing out. And what he told me to check out was Mosaic, which is the first ever web browser invented by Mark Andreessen, who was then a graduate student at Champaign-Urbana, University of Illinois, Champaign-Urbana. And the reason why a web browser was important was that even though Tim Berners-Lee invented... the hypertext transfer protocol or HTTP in 1989, it was not usable because if you know, if you look at your usual URL, it's just like a long string, alphabetical string of figures and numbers. But here, this was, if you put in the New York times, it would bring you to the New York times, but I didn't know that yet. So it seems he was a friend of mine. I said, go buy this and see what you think. And then, so I, back then I went to RadioShack, which is also out of business now along with that. And I bought... for, I don't know, $29.95, this like cardboard thing with seven floppy disks. It was just, I remember it was just big because, you know, they thought people would steal it or something. So I bought this seven floppy disks. You upload it, you know, and these days you download, for free, you download these amazing browsers. But, you know, then, and I upload, so I got this web browser and then I sort of see what it does. And I go, this is the one thing. where we are on a level playing field. Everything else, we're way behind. Roads, hospitals, telecommunications, everything, we're way behind. This is one area where, and then I looked at the numbers, basically, I mean, no one had anything. I mean, the U.S. was sort of in the lead, but in terms of the statistics you had then were actually a number of websites. But it was like everyone was behind. So the first thing I said, okay, what we got to do, if we really want to win, we got to pick a thing where we are on a level playing field with everyone else. And then I said, okay, how are we going to do that? And I figured the country's full of sticks in the mud. And they're like, what are you talking about? This is crazy. No way. Which was, in fact, the case. The other thing that, you know, I brought in this other knowledge, which was basically there had been in my country in the 1920s, this huge. language reform and and the way it was done which had we had got all these new words changed the old grammar did all this stuff and the way it was done was that there was this genius who was the sort of the guy who created these new terms to deal with the modern era he just made the book the elementary school text that all kids had to learn with a little thing in there saying if your teacher tells you otherwise don't listen to him but anyway so what happened was that 20 years after Afterwards, all the old words were forgotten, and the new words were what everyone thought were always being used. I said, this is what we got to do. We get the young people. And so I said, okay, what we should do is put computers, computer banks in every school. And on top of that, the government doesn't pay for all of them. Because another thing I once read somewhere, anyway, basically, you have to have skin in the game. There's a great example from like... Forty years ago, when the first computer games came out, then some sort of experimental psychologists realized that the skills involved in computer games were the same ones that were very, that translated into fighter pilots' skills. So then they put all these computer games in fighter pilots' barracks, and they just gathered dust. So then the Air Force went to some consulting company and said, what do we do? They said, oh, very simple. Just put a little slot in there and make them pay a quarter. And as soon as they did that, all the fighter pilots were lining up to be able to play the game. Because as long as it's free, it's like, ah, you know, who cares? So when I said, okay, how do we do this? I said, I explained to the government what we do is municipal governments, because that's the level of education here. They, you know, your town or village pays for, you know, for deal, I guess, the budget to deal with education. I said half for anyone who wants it. Well, the government pay for half. You kind of come up with the other half. So in the beginning, like there are four or five schools with some, you know, young, bright math teachers that we got to do this. And then the other wonderful motivator. as I predicted, the motivator of human behavior, envy kicked in. And so if you have a little township here, like, you know, it's got like 5,000 people in it, then they have like, you have the ones around it. And so what happened was the one would get it, and then all the other people around would say, how come they have that? We don't. Which they would then go to their board of education and say, we want that thing that they have there. What that meant was, I mean, the program took me from 93 to 95. to convince the government. And at those years, I was like, I mean, basically the Teachers Union newspaper did not, I mean, which is a weekly, did not, there was not an issue that did not attack me for one way or another from this idea as being completely stupid, ridiculous, the enemy of the culture, all this crap. Anyway, so we got the government to do it in 96. By the end of 98, 99, night. All Estonian schools were digital. If you fast forward from that 20 years, I was in my last year of my presidency, and I always go to startups, you know, just to pat them on the head and say, you're great. This is wonderful. And I started asking them, how did you get into this? Why are you doing this? You know, whatever you're doing, you're a startup. And I started counting them up. Basically, 80% of the time of these startups, people would say. oh, I was a kid in your program. So now they were like, you know, 32, 35. They've been coding for 20 years. So that's part of my explanation for why Estonia has the highest number of unicorns per capita, which we have one for every 133 people, 133,000 people in the country. I think Israel's number two. They're like one unicorn for every, I don't know. 800,000. But anyway, just the per capita, the highest number of unicorns and everyone. I mean, all of that's how we later on, once this thing started really going and that became like a thing and people, the government started trying sort of elementary digitization long before anyone else. The banks came up with electronic banking, which was better than anyone else's in the area. I mean, they ended up being taken by, you know, Swedish. banks to come and do theirs. And then what happened basically, and this is where it goes beyond me. I mean, I kickstarted it, but the much smarter people than I am figured out that if you really want to do digitization properly, you need to have a secure, unique identity for every person. You need to have a secure architecture. And then what came out of that is what we have in Estonia today, which is probably the most, I mean, with possible, you know, with maybe competing with Singapore, the most digitized government and public services anywhere. Even that, I mean, I guess the Estonian sort of approach that was kind of similar to what I did, I mean, sort of mentally, which was that they thought of the system we have as now it's been taken over by about 25 countries, more or less, to varying degrees. The thing that was unique, and this we can talk about later on when it comes to AI, is that we only invented one small part of that. All the rest existed. In fact, the unique identity part had existed for 25 years, since 1975, which was a chip card, which would allow you to do two-factor authentication, which is now common everywhere. I mean, all credit cards today, even in the US, chip. But back then, no one ever heard of it. Now, the thing is that you take something that's been around, a chip card or a chip in a car, basically, and you use it in a completely different way. And it provides you with something that no one else has. And so, too, with the architecture, which was invented locally, but it was invented by these kids in the university. I mean, they're 20-year-olds. And they said, OK. What we really need is a distributed data exchange layer so we have, you know, we don't have a single database anywhere that it can be hacked. You know, the worst case of that is the... OPM or Office of Personal Management hack in the US where they stuck everything in one place and everything was sucked out. Whereas in my country, all the data is individual. I mean, sort of my, here I have my driver's record, here's my health record, here's someone else's health record, here's someone else. So basically, the worst that can happen if someone breaks into the system, if they manage, is to get one cell, which would be, say, my... my health record you know even that would be bad but the point is it's not like when you someone hacks into the u.s government master file of all federal employees and you find you get things such as the you know the psychological profiles of cia officers and the home addresses of fbi agents i mean all the stuff that was just stolen because it's all dumped into one so that was the beginning of the that digitization program but you know so basically for you I would say what lessons learned one is have a broad range of experiences and readings so you can put things together and then use it in a different way.

  • Speaker #1

    I want to ask you about that resistance because you mentioned the teachers union paper that would criticize you every single week. What would be your advice that you'd share with leaders who actually have some brilliant ideas so that at least they think that they can do something differently and they need. to convince the crowd or the masses, really? Because, you know, you won't get too far if you don't get them on board.

  • Speaker #0

    Well, basically, the reason they attacked me was precisely because it was the reason I knew they would. Because the teachers, the math teachers, or the teachers didn't know how to program. And that's why I wanted to get the kids. Because if I get the kids, the kids will do it on their own anyway. They don't have to have a competent teacher. We know from, you know, from... years and years of experience. You give a kid a computer, okay, he may break it, but most likely he's going to figure it out much faster than older people. I mean, that's why I wanted to start young, so that I knew that, you know, I mean, basically, you know, educational reform to have an effect takes 15 to 20 years. I figured 15, 20 years, it's fine. Give them the computer now, and we'll see that, you know, there weren't enough qualified teachers to actually teach programming. The kids learn themselves. I mean, that was what I thought. That was what I hoped. And that's what happened. But the opposition was strong. Yeah. But well, basically, because of social pressure from parents saying, you know, we want our kids to have this, the opposition among other groups was lessened because the parents are the voters.

  • Speaker #1

    So the other large area you also had a role in is obviously the EU accession process. And that's a completely different story. It seems Estonia wasn't particularly interested in joining the European Union, right?

  • Speaker #0

    Well, Estonia itself was not interested, and most of Europe did not consider us a country that would ever join. And it was, you know, former Soviet Republic, blah, blah, blah. And the reason what Estonians didn't want to do is because they, because of our historical experience, experience getting invaded by the Soviets, invaded by the Nazis, invaded by again by the Soviets, and then 50 years of Soviet occupation was, we have to get into NATO. We have to get into NATO, NATO, NATO, NATO. And this was the attitude among basically all Eastern European countries. But there was a hope for Poland and the Czechs and the Hungarians that they could also join the EU. I mean, those countries also wanted only to get into... into NATO and all the other stuff, Moon cares. And Eastern Europeans were kind of anti-EU back then, kind of like, we don't need that socialist stuff or, I mean, whatever. On top of that, it became clear that certain countries, Germany first and foremost, were completely against our ever joining the EU even. So I thought about this. I was at the time, I was the ambassador in the United States. And I kept I kept getting these messages saying, forget it, forget it. You'll never get either one, especially not NATO. And then trying to figure out what do we do? I said, well, the problem with NATO, joining NATO, it is a strictly political decision. And so even if you could, you know, I could sort of schmooze the U.S. government to say, okay, we support you. I mean, because there were sympathetic people there, but, you know, they're still like, nah. But the opposition of... basically the large EU countries, I mean, Germany, first and foremost, France, Italy, UK at the time they were in the EU. I mean, in NATO, they would never let us in. But that's a political decision. Now, the EU, on the other hand, the decision as to whether, especially given the sort of the approach the EU took was, it was not political. It was, you have to meet certain criteria. They're very strict criteria. They're difficult criteria to meet. But I said, okay, we can do that. That's something we have agency in. We cannot change the political attitude regarding NATO. But we can change the attitude towards us based on our performance. There was some crisis in the Estonian government, and so I was appointed foreign minister. So since I'd been pushing this line, I said, okay, now we do this. The first meeting we had with the leadership of the foreign ministry was, I knew everyone, basically, you know, 15 people, different departments. And there was one person I didn't know. And it was this very young woman, I don't know, 23, 24. And I said, I don't know you. Who are you? And she goes, tell me your name. And I said, and what do you do? And I said, well, I run the European Integration Bureau. And I said, oh, how big is that? She said, I am the European Integration Bureau, which showed what the... foreign ministry's attitude towards joining the EU was. So I just completely changed that. I said, okay, we redo the budget. We don't have embassies. And like at that time, there are 12 countries in the EU. We opened all new embassies. We completely redid the whole approach to legislation, prioritizing which legislation gets done. Mirabile dicto. In 1997, when they came to decide who qualified, they chose six countries, and we were one of them, because our performance was like that. Now, I mean, that was just like, not in the cards that this would happen. But I mean, if you just push it and you do something that was weird, people came along and did it. Now, our two southern neighbors, Latvia and Lithuania, didn't have that kind of approach. Called me crazy. He said, you know, El-Wislam's on the EU. Why is he doing that? It's only in NATO that matters. But as it happened, I mean, the whole point of joining the EU, ultimately, and that was my nasty thought behind my mind, is that if we can get into the European Union, the other EU members in NATO can no longer veto us. So that basically eliminated all possible vetoes from the UK, Germany, France, Italy, and it basically left... three countries to convince. Turkey, Norway, well four, Iceland, not a problem, and the US. So if you get Canada, right, Canada, Norway, US, Iceland, and Turkey. Now, if those you get on board, you're it. And that's how we got into NATO. I mean, that was, again, it was something that the foreign ministry, when I became foreign minister, basically, as with the computers, it's crazy, This is stupid. This is not important, but I was foreign minister, so they didn't have any choice. So anyway, those are, I guess, the things that counted.

  • Speaker #1

    When I'm listening to these stories, I'm thinking that when a country wants to redefine itself, it really starts with clarity and intentionality. When was that moment when Estonia sort of stopped describing itself as a country in transition and began thinking in terms of designing the future? This is exactly where we are going. Do you remember that moment?

  • Speaker #0

    It happened in different parts of society at different times, I mean, different ministries. There were some that were very sort of forward-leaning, even resentful of this idea of transition. Today, you know, there's a yearly report that comes out, Nations in Transition, which is only about Eastern Europe. You know, I look at this, Estonia is like number two in the world in press freedom, number five in the world in social support for families. It's the only East European country that has legalized gay marriage. I mean, it is less corrupt than most of the EU. So And then I was like, what do you mean nations? Why don't you do a little transition for some of these other countries, right? Yeah, I mean, look at this. Estonia is number two in press freedom. You know what the U.S. is today? 57. I mean, it's like, come on. This whole idea of former Soviet republicans, like, that's a third of a century ago. We have completely changed. I don't want to hear it. So, I mean, the transition part. I mean, I started bugging me a lot earlier just because I would follow the statistics on who's where doing what. Then you look at these numbers and you go, you know, we're not there. I mean, we're not like those countries we should be transitioning to because we're better than they are. And that was kind of always annoying. Some of the problem was, I mean, they had to convince countries to do things like, well, we should we give you visa free travel to Europe? You know, what? So, I mean, all of that... As I said, it's changed dramatically, but it is, it's still, there is an attitude about Eastern Europe is like, oh, listen. Whereas, in fact, it's cleaner, less corrupt, better educated than most of Western Europe today. In fact, in non-Asian countries, that is outside Japan, Korea, Singapore, China, Taiwan. We have the best scores on math and language skills on the OECD PISA test, right? So our educational system is rather good, if that's the case, right? So all of that just shows that, you know, old stereotypes die hard. And I think if you ask, when did this whole idea of transition end? I think it ended with slowly realizing that in whatever your area is, you're actually at least as good, if not better. than the people who are sort of calling you a transitional venture.

  • Speaker #1

    So if you think about reinvention and transformation, it's really an ongoing process. It's not a one-off project. So when you think about Estonia, how do you think the country should or perhaps could reinvent itself right now?

  • Speaker #0

    And when I think about the direction things are going in, we have the big challenge is what happens to this little country in the era of AI? You know, we're small, right? I mean, we don't have that many people. How are we going to, I mean, we'll never be able to compete with the U.S. or China on this. On the other hand, being creative in using AI, you can do all kinds of stuff. One of the stories I tell a lot about is after I was president, I was invited to Stanford University because it was the center of IT in the world. So I go there. I mean, Stanford's very nice. I had to register my kid to go to school there. The way I did it, I had to take my electricity bill. I had to drive down to the headquarters of the school education department. I had to take a number to go in. I had to present my passport. I mean, 17 different documents all on paper. When I finally got to the person behind the desk, she took all the stack of papers, went over and photocopied them all. And then she came back, gave me the stuff back. And then... By hand, she started filling out, you know, whatever, from the photocopies, she started filling out these forms. I was kind of like, you know, Estonia, none of that happens. None of that, right? I mean, it's like, where do you live? We know where, I mean, you know, we know where you live. You get, because you're registered to live there and because it's Everest's birth and whenever you get, when the kid turns a certain age, you get a little email that says. By the way, September 1, school starts, and here's, you know, we give a little school supplies. Are the kids vaccinated? Medical records all exist. They're online. They can check to see. They can't see who you are, but they can see if you say, is this person vaccinated with the required vaccine? All of that's done. You know, this came up with my oldest son who came to the U.S. during COVID. And he got, he was there just for two weeks, but he got vaccinated. and you you came back and it is the yellow card. Here in Estonia, we had, in fact, Estonia was an Estonian company invented the app that is used all over Europe to show that you have been vaccinated because it checks. whether you are or not, without actually accessing your name and data, it just reports back saying, this person is vaccinated. And so he came back and he said, well, all right. And here he went to the doctor. Here, here's my little, my little card was filled out by hand saying vaccinated. What do I do with this? I mean, you know, you're not in the computer. So clearly in the United States, yeah, another example. It was only, I think in 2013, the U.S. military started using chips for two-factor authentication. I mean, we've been doing it for 13 years or so. And to this day, the US government, despite Doge, which is not what you have to know, Doge is not the way to do it. I mean, it's my son, my oldest son, who is now 37. Actually, because he grew up in this insane family, he was always like Anil Ander. Well, he eventually, he ended up being the CIO of the country. Well, he doesn't. published a paper for a German think tank. It's in English, but it's a German think tank, basically showing all of the issues you have to deal with in order to digitize or to use AI in a way that respects rights and freedoms and reform government. None of those are in Doge. No one thought they just went and just chopped things up as opposed to thinking it through. I mean, even the original. pre-AI period, it took us about three or four years to figure out all the legal connections that you have to make. I mean, who can see what? What kind of level of permission does a government official have to see something? Because certain things, you know, public health, you have to see something. People shouldn't be able to see your healthcare records. But on the other hand, in terms of, you know, if there's an epidemic or something, all these very difficult to find questions that must be defined by law. not you don't go in there with an axe and start cutting with and call yourself big balls what do you think estonia will sort of pivot what's next for estonia well i think that the way it'd be given the level of thinking here i think we probably will be one of the thought leaders on a use of ai in public services and that's one place where i think it could be most useful. All the other stuff. It could be a lot of fun and even all kinds of stuff. But as long as the citizen has to face traditional, usually undigitized, but even if slightly digitized government, I mean, what do I do? I want to get a fishing license. Well, I don't know. What do I do? I mean, I have to go get, I mean, I have to do something, whatever it is. I mean, we have part of this already working here since like 2000, which when I do my taxes, I get all my, I get my tax, they're filled out for me. everything's filled out everything i made everything all my charitable donations everything is in there and i did this we're sat there on the screen and you can check it all through and say is this right and it's always right it's always been and then you just press enter and your taxes are done right i mean so i mean the kinds of thing that to me we can foresee in the future is I mean, AI working out for companies. I mean, to think of government. as a service that government. So instead of going after a company that is, it hasn't paid its taxes because it's been, it's been in trouble. Instead, the AI will say, you know, your tax risk, your receipt, I mean, your income is not really meeting what your expenditures are and your loan obligations. And then maybe, maybe you should come and talk. to us, maybe we'll, you know, lighten your tax load so you get over this problem that you may not even know you have because, well, we do have sort of online reporting of all income and expenditures here. So we don't, I mean, we do quarterly reports if you want, but basically you can sign up and just everything happens digitally. So that information is there. It just could be sort of operationalized so that the tax department says, by the way, you know, doesn't look so good. Maybe we need to restructure your tax obligations and, you know, I mean, all these things that governments can do. Governments, I mean, sort of same thing with health care monitoring. I mean, if it's that it can notice, I mean, there's so many things that can notice it depending on how much you want to monitor. Right. I mean, there are ways of monitoring, constantly monitoring your level of health, your blood pressure, all these things can be done. And the AI will say... By the way, here, why don't you come in for something? That's where I see it going because, I mean, you're going to get amazing products from all kinds of huge companies whose yearly income is like a thousand times the GDP of my country. So I'm not worried about that. But it's the application side. And it's also my own experience with the level of application of the old digital revolution in other countries, which was none of it. really in public services. And it's especially true in the United States where, I mean, it doesn't really, you can't, the difference between what you can do, the amazing things that you can do with this here, compared to what private companies, compared to what I can do with in my country on here for whatever, filling out, I mean, applying for something, getting whatever. I mean, I can do it all night. Certainly, we've gotten to the point where the, until this year, there was only one thing you couldn't do online, which was get divorced. As of January 1, you can even get divorced online.

  • Speaker #1

    So I publish a weekly column that is focused on various aspects of reinvention. And I share articles that. discuss various topics and I ask questions. And there was one article from the Wall Street Journal recently saying that some AI models are already rewriting their own shutdown code. And this is because we're not teaching AI to think like us. We're teaching it to win. So my question was, what else are we handing over to machines that haven't truly understood what we meant, but will follow anyway? What are your thoughts about such trends and dangers that we're perhaps not seeing.

  • Speaker #0

    Well, what I have followed is this whole idea which has gone out of the United States in the last five months, which is that you collect all this data and put it into one place, which is something we specifically designed our system to compartmentalize everything. Now, aside from the security risks, I mean, you can actually, once you apply AI to these data, you can start finding out things that you probably wouldn't want to. You wouldn't want the government to know. And that's my worry is that, okay, the government then has a tool. I mean, especially because there's no legal basis for any of this. There's no law allowing the U.S. government to do what it just did in the past five months. In this country, you know, anything that changes the way anyone can look at data requires that legal foundation. And, you know, sort of going through the whole process, does this violate basic fundamental rights and privacy rights? Which makes it, you know, slower. On the other hand, we do it, which makes us feel a lot much safer.

  • Speaker #1

    So I want to go back to you now towards the end of the conversation. You've worked across a number of different identities. You were a journalist, diplomat, president, now a thought leader, an educator. How has your definition of reinvention or transformation changed across these roles?

  • Speaker #0

    Well, I don't know. I mean, basically every position I've been in, I've had some weird ideas and done things differently. It's always been like that, basically. I don't know. When I was at Radio Free Europe, I was head of the Estonian service. And then it was like 1988. And everyone was saying, oh, Glasnost perestroika. I was like 36 years old. No, I was like 34 years old. Yeah, 34 years old. I was head of the Estonian Serbs. I said, oh, well, how about I go visit the Estonian part of the Soviet Union? Now, I mean, for that, I mean, it was like, nope. The only people that ever got from Radio Free Europe to the Soviet Union were people who re-defected. So, but I said, you know, we should call them on their bluff. And then I went to my leadership, went up to Washington, you know, this crazy guy who wants to go to visit Estonia. And it took them like three months, right? I said, okay, you can try, but they won't let you in, right? Well, anyway, so as they said, okay, then I wrote to the so-called foreign minister of Estonia saying, by the way, in the spirit of Lasnost and Perestroika, you know, I say it's all open and free speech, and how about if you let me in? I mean, I like to visit. It's like, no, three months go by, you know, and then finally I get this notice. It's like, yeah, you can come. But then I went, I was in Munich. I went to the Soviet consulate there. They refused to give it to me. So I called them up. I said, what do you do? They said, well, I'll tell you what you do. Fly into Finland. And then you call this number. So, I mean, people were thinking out of the box in Estonia, too. This guy's KGB basically telling me, he says, call this number. And you meet this guy and give him your papers. And by the way, if he gets it done, give him a bottle of Western cognac. So that's what I did. I mean, I flew to Finland not knowing if I was going to get in. But I called up the guy and I gave him my papers and I got my visa and I gave him a bottle of Hennessy. It worked. But basically, you have to be, you know, if you remain constricted by the rules. You don't come up with new ideas, that's all. I mean, it just seemed like no one else had ready for your book. Oh, with Blasphemer's Perestroika, why don't we try this? It was just, I thought, well, it's kind of nuts, you know.

  • Speaker #1

    Okay, so what book is currently sitting on your bedside table?

  • Speaker #0

    New Mendelssohn translation of The Odyssey.

  • Speaker #1

    And I want to ask you before we close, if you could ask one deep, unsettling question of yourself, of leaders of the next generation, what would that be? What is the question that is still sort of challenging you specifically?

  • Speaker #0

    Oh, there's so many, I don't know. There's no single one. I mean, I would get... I was like, you know, what's your favorite color? Like, I don't know, one question. Well, I guess what I think about the most question, what I think about most is why is it after the complete victory of the Enlightenment and bettering, pulling us out of the Middle Ages and made a rational thought, scientific evidence, have we descended back into this sort of Again, I would say medieval conspiracy theory, rumor-based insanity that we see. And it's just so bizarre because, you know, you would never get this without the science that came out of the Enlightenment. But, well, they're the same thing. I remember reading, you know, 40 years ago, V.S. Naipaul's Among the Believers, you know, and you have this, like, total turn of Iran towards sort of medieval belief. Yet they all had modern weapons. I don't know how we got there that we've given up. So much of society, so many governments have abandoned the rational thought that from the 18th century on, well, maybe earlier, from the Renaissance on to through the Reformation and the Enlightenment, have brought us to a level of wealth, well-being, prosperity that was never, ever imagined. Thomas Hobbes said the life of a primitive man was nasty, brutish, and short. Well, I mean, how it stopped being nasty, brutish, and short was through science, evidence, rules, you know, all that. And yet we're turning against it. And that's what really shocks me.

  • Speaker #1

    Thomas, thank you so much for the conversation. I really enjoyed it. And I'm looking forward to meeting you in person.

  • Speaker #0

    Great. Well. If you're ever in Estonia, I would recommend doing it in the summer. All right. Great.

  • Speaker #1

    Thanks for joining me today. If today's story left you with a question or a quiet nudge, leave a comment or share the episode. Subscribe if you'd like to keep on listening. And remember, the next chapter doesn't always begin with a plan. Sometimes it starts with a pause.

Share

Embed

Description

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

Stay connected

Subscribe to Inside Reinvention.
Follow Andrew Wrobel (website, Linkedin and Instagram) and Reinvantage (website, Linkedin, Instagram) for new episodes, tools, and research.


Hosted by Ausha. See ausha.co/privacy-policy for more information.

Transcription

  • Speaker #0

    This is the one thing where we are on a level playing field. Everything else, we're way behind. Just trying to do things a little differently. I don't know why, but I've always had this thing, let's try it differently, let's try something some different way. It did show me that having learned something like that at an early age was important. Then I used a quarter century later to help digitize my country. You know, if you remain constricted by the rules, you don't come up with new ideas. So much of society, so many governments have abandoned the rational thought, and that's what really shocks me.

  • Speaker #1

    This is Inside Reinvention. I am Andrew Robel, and in this series, I speak with people who have rewritten the rules, sometimes by choice, often by necessity. It's not about starting over, it's about seeing differently, choosing deliberately, and moving forward with clarity. My guest today is Tomas Hendrik Ilves, a former president of Estonia. He is widely credited with shaping one of the world's most ambitious digital societies. But that's the outcome. What I want to understand is the thinking that led there, the doubts, the decisions, and the moments of clarity that shaped not just a country, but the way we think and talk about digital future. This conversation isn't about looking back. It's about how reinvention begins, how it unfolds, and what it continues to demand from us. A very warm welcome to the first episode of Inside Reinvention. Thomas, it's so great to have you here.

  • Speaker #0

    Well, we'll see. The first time, we'll see how it goes.

  • Speaker #1

    Okay, so before we talk about the title, before we talk about the impact, when you were still very, very young... You know, you were trying to imagine your place in the world. Who are you trying to become?

  • Speaker #0

    I don't know if I really did want to become anyone. I was just, I was more involved in just things that interested me rather than having a future goal. From a very early age, I didn't want to know as much as possible about everything. That was kind of the, I don't know. I mean, I was always reading stuff, you know, asking questions and. From an early age, I had, I mean, which was illusory, but I thought I had like a different way of looking at things. Had to write a paper in high school or something. I would come up with a new thesis and people would look at me weird. And then sometimes they'd go, well, anyway, I mean, it was basically just trying to do things a little differently. I don't know why, but I've always had this thing. Let's try it differently. Let's try something some different way. And probably I would say, you know, being self-deprecating, that I didn't think I could do it the way... everyone else was doing it, so I might as well try some other way. I think that's, you know, sort of imposter syndrome or something.

  • Speaker #1

    And do you remember your first job, the one you actually got paid for?

  • Speaker #0

    It's hard to say if it was a job. I did stuff that I got paid for, but it was nothing, nothing much. The only relevant job I would say that I had that, I mean, was not my first, but which showed me something that was really important for my later life. I mean, it was something I learned in college. But when I was 17, 16, 17, I had a brilliant math teacher who was doing her PhD at Columbia Teachers College in education. And her idea was, let's see if we could teach kids to program or code. This was in 1971. And so she did this, had this class of 12 of us, and she taught us basic. which is baby Fortran. I mean, she was still today, but at that time, it was, like I looked it up later, it had only been invented a year earlier. And she went and rented a Teletype machine with a Perfo tape, like a long yellow tape. No one remembers these things, but okay. It was, and then we had a big telephone modem. You take, you know, the old phone, you stick it into the, in there, and then it was connected. It was dial-up. connected to a mainframe computer, basically 50 kilometers or 30 miles away. And then we had a little budget to be able to do stuff. The reason you used the Perfotate was that you would basically test out your programs and write them there. And so I learned the code in BASIC. Well, okay. I mean, it was, I didn't think about it. All the other, the boys in the class, other boys in the class, they're all like tech millionaires today. I never, you know, I didn't do that. But then I went to, when I was an undergraduate, I saw a little ad back in the day when they had three-by-five-inch file cards that said, on the bulletin board, programmer, 10 hours, 10 to 15 hours a week in the site department. I said, oh, I know how to program. So I went there, and then it turned out. It was. Professor had bought, I think, the first commercially available lab computer, which was a PDP-8 put up by DEC, which is long out of business, Digital Equipment Corporation. It had 8K of memory. 8K, that's as much as an empty email today, right? But because it had 8K memory, and I have no recollection of what the processor was at the time, but I had a... program in assembler language, which is hexadecimal. I mean, base 16, zero through nine, A, B, C, D, E, F. But program is program. You just, instead of saying go to or whatever you do right on the higher level language, you just write the numbers in. And I said, wow, I could know program because basically it's the language itself is ultimately irrelevant. So that was what I really learned. I was making minimum wage, which at that That time was, I guess, $2.15 an hour. It was a long time ago. That was an interesting lesson. Otherwise, I mean, I had jobs doing stuff, but I mean, that was kind of meh. It wasn't anything where you had any engagement in a serious way or any real agency, but that at least, I mean, you didn't have much agency there either. I just had to sort of figure out how to program this computer. But it did show me that. having learned something like that at an early age was important, which then I used a quarter century later to help digitize my country, which we can get to later on.

  • Speaker #1

    Yeah. So speaking about that, I mean, you mentioned thinking out of the box or maybe even considering there was no box in the first place. And you mentioned Estonia. So before you became president, you have done some amazing stuff for the country. And we're talking about two different things, right? The first one is the digitalization. And we know that 100% of public services right now in Estonia have been digital for quite some time. But the other thing is having Estonia in the EU, which was not something people envisioned at the time, right?

  • Speaker #0

    Well, the digitalization came first. I mean, basically, it was a result of the extreme poverty of Estonia once it became independent again. It had been independent before World War II. And if you read, you'll find in volume two, the Cambridge economic history of Europe, little bar graph, and then it has GDP per capita of countries in Europe. And there it said Estonia had a slightly higher GDP per capita than Finland. That was in 1938, the last full year before World War II when everything went to hell. In 1939, the Finns were invaded, all this. So 1938 is like the last time to look at the countries. The next time, if you look at the GDP per capita of Estonian Finland in 1992, which was the first full year of our independence on our part, then the GDP of Finland at the time, the nominal GDP per capita nominal was $23,800. So basically $24,000 per person. The GDP per capita. of Estonia was 2,800. So basically, Finns had become in the interim eight and a half times richer. Now, what that meant? Well, I mean, I was invited to become, I had U.S. citizenship, I was working at Radio Free Europe, and then the president of the country after our first democratic election said, look, what are you doing over there? You know, come on, let's go come work and help build up the country. I said, okay. I didn't realize how much I was. What a cut in pay I would take. So I went to Washington. I was the ambassador. And we were so poor that there were times when they wouldn't send money from our country, from Estonia, to pay us. So then we'd live another three weeks on credit cards. And I was like, what do we do? How do we get out of this poverty? And the thing about the two aspects of poverty, which I want to talk about, one is that even the GDP figures per capita don't even say enough. because in the interim, we have not built... highway. We have not built, you know, modern hospitals. The buildings are all falling apart. The basic state of the country is much poorer, even if you eliminate the income differences. So because they've had 50 years of development, which we had not had. And the other problem was take from Zeno's paradox of Achilles and the turtle. One of his paradoxes, but it's, But, you know, it's like when the turtle starts going. then the fastest man in earth in Greek mythology, Achilles, by the time he catches up to where the turtle was, the turtle has moved on. Now, what that means in GDP. per capita or GDP, is that, okay, I mean, if Finland starts off at 24,000 US dollars per capita and they have a miserable year of 1% growth, and Estonia has an incredible 8% growth, which is a phenomenal growth rate, we would still lag more behind than we were before. So this is the fundamental problem of development. At home here in Estonia, where I am right now, there were all kinds of theories about what we should do. And so they were like the left, the hard left. They said we should just keep on with communism. And then you had the hard right saying, oh, we should become Singapore. And it was all basic sort of classic economic theory. I saw it differently, though. I mean, first of all, I was just as lost. And I was going, you know, it showed up when you couldn't pay any for anything. because I've been a geek. Because I learned to code when I was 17. And then people knew that and they'd known me. I dealt with this stuff, played around with it even before anything real happened. I bought my first Apple IIe in 1983 or something. So I played around. People thought I was a little weird. So a friend of mine sent me an email. And I was one of the few people who had emails even then. But I said, OK. And he sent me an email and said, look, check. this thing out. And what he told me to check out was Mosaic, which is the first ever web browser invented by Mark Andreessen, who was then a graduate student at Champaign-Urbana, University of Illinois, Champaign-Urbana. And the reason why a web browser was important was that even though Tim Berners-Lee invented... the hypertext transfer protocol or HTTP in 1989, it was not usable because if you know, if you look at your usual URL, it's just like a long string, alphabetical string of figures and numbers. But here, this was, if you put in the New York times, it would bring you to the New York times, but I didn't know that yet. So it seems he was a friend of mine. I said, go buy this and see what you think. And then, so I, back then I went to RadioShack, which is also out of business now along with that. And I bought... for, I don't know, $29.95, this like cardboard thing with seven floppy disks. It was just, I remember it was just big because, you know, they thought people would steal it or something. So I bought this seven floppy disks. You upload it, you know, and these days you download, for free, you download these amazing browsers. But, you know, then, and I upload, so I got this web browser and then I sort of see what it does. And I go, this is the one thing. where we are on a level playing field. Everything else, we're way behind. Roads, hospitals, telecommunications, everything, we're way behind. This is one area where, and then I looked at the numbers, basically, I mean, no one had anything. I mean, the U.S. was sort of in the lead, but in terms of the statistics you had then were actually a number of websites. But it was like everyone was behind. So the first thing I said, okay, what we got to do, if we really want to win, we got to pick a thing where we are on a level playing field with everyone else. And then I said, okay, how are we going to do that? And I figured the country's full of sticks in the mud. And they're like, what are you talking about? This is crazy. No way. Which was, in fact, the case. The other thing that, you know, I brought in this other knowledge, which was basically there had been in my country in the 1920s, this huge. language reform and and the way it was done which had we had got all these new words changed the old grammar did all this stuff and the way it was done was that there was this genius who was the sort of the guy who created these new terms to deal with the modern era he just made the book the elementary school text that all kids had to learn with a little thing in there saying if your teacher tells you otherwise don't listen to him but anyway so what happened was that 20 years after Afterwards, all the old words were forgotten, and the new words were what everyone thought were always being used. I said, this is what we got to do. We get the young people. And so I said, okay, what we should do is put computers, computer banks in every school. And on top of that, the government doesn't pay for all of them. Because another thing I once read somewhere, anyway, basically, you have to have skin in the game. There's a great example from like... Forty years ago, when the first computer games came out, then some sort of experimental psychologists realized that the skills involved in computer games were the same ones that were very, that translated into fighter pilots' skills. So then they put all these computer games in fighter pilots' barracks, and they just gathered dust. So then the Air Force went to some consulting company and said, what do we do? They said, oh, very simple. Just put a little slot in there and make them pay a quarter. And as soon as they did that, all the fighter pilots were lining up to be able to play the game. Because as long as it's free, it's like, ah, you know, who cares? So when I said, okay, how do we do this? I said, I explained to the government what we do is municipal governments, because that's the level of education here. They, you know, your town or village pays for, you know, for deal, I guess, the budget to deal with education. I said half for anyone who wants it. Well, the government pay for half. You kind of come up with the other half. So in the beginning, like there are four or five schools with some, you know, young, bright math teachers that we got to do this. And then the other wonderful motivator. as I predicted, the motivator of human behavior, envy kicked in. And so if you have a little township here, like, you know, it's got like 5,000 people in it, then they have like, you have the ones around it. And so what happened was the one would get it, and then all the other people around would say, how come they have that? We don't. Which they would then go to their board of education and say, we want that thing that they have there. What that meant was, I mean, the program took me from 93 to 95. to convince the government. And at those years, I was like, I mean, basically the Teachers Union newspaper did not, I mean, which is a weekly, did not, there was not an issue that did not attack me for one way or another from this idea as being completely stupid, ridiculous, the enemy of the culture, all this crap. Anyway, so we got the government to do it in 96. By the end of 98, 99, night. All Estonian schools were digital. If you fast forward from that 20 years, I was in my last year of my presidency, and I always go to startups, you know, just to pat them on the head and say, you're great. This is wonderful. And I started asking them, how did you get into this? Why are you doing this? You know, whatever you're doing, you're a startup. And I started counting them up. Basically, 80% of the time of these startups, people would say. oh, I was a kid in your program. So now they were like, you know, 32, 35. They've been coding for 20 years. So that's part of my explanation for why Estonia has the highest number of unicorns per capita, which we have one for every 133 people, 133,000 people in the country. I think Israel's number two. They're like one unicorn for every, I don't know. 800,000. But anyway, just the per capita, the highest number of unicorns and everyone. I mean, all of that's how we later on, once this thing started really going and that became like a thing and people, the government started trying sort of elementary digitization long before anyone else. The banks came up with electronic banking, which was better than anyone else's in the area. I mean, they ended up being taken by, you know, Swedish. banks to come and do theirs. And then what happened basically, and this is where it goes beyond me. I mean, I kickstarted it, but the much smarter people than I am figured out that if you really want to do digitization properly, you need to have a secure, unique identity for every person. You need to have a secure architecture. And then what came out of that is what we have in Estonia today, which is probably the most, I mean, with possible, you know, with maybe competing with Singapore, the most digitized government and public services anywhere. Even that, I mean, I guess the Estonian sort of approach that was kind of similar to what I did, I mean, sort of mentally, which was that they thought of the system we have as now it's been taken over by about 25 countries, more or less, to varying degrees. The thing that was unique, and this we can talk about later on when it comes to AI, is that we only invented one small part of that. All the rest existed. In fact, the unique identity part had existed for 25 years, since 1975, which was a chip card, which would allow you to do two-factor authentication, which is now common everywhere. I mean, all credit cards today, even in the US, chip. But back then, no one ever heard of it. Now, the thing is that you take something that's been around, a chip card or a chip in a car, basically, and you use it in a completely different way. And it provides you with something that no one else has. And so, too, with the architecture, which was invented locally, but it was invented by these kids in the university. I mean, they're 20-year-olds. And they said, OK. What we really need is a distributed data exchange layer so we have, you know, we don't have a single database anywhere that it can be hacked. You know, the worst case of that is the... OPM or Office of Personal Management hack in the US where they stuck everything in one place and everything was sucked out. Whereas in my country, all the data is individual. I mean, sort of my, here I have my driver's record, here's my health record, here's someone else's health record, here's someone else. So basically, the worst that can happen if someone breaks into the system, if they manage, is to get one cell, which would be, say, my... my health record you know even that would be bad but the point is it's not like when you someone hacks into the u.s government master file of all federal employees and you find you get things such as the you know the psychological profiles of cia officers and the home addresses of fbi agents i mean all the stuff that was just stolen because it's all dumped into one so that was the beginning of the that digitization program but you know so basically for you I would say what lessons learned one is have a broad range of experiences and readings so you can put things together and then use it in a different way.

  • Speaker #1

    I want to ask you about that resistance because you mentioned the teachers union paper that would criticize you every single week. What would be your advice that you'd share with leaders who actually have some brilliant ideas so that at least they think that they can do something differently and they need. to convince the crowd or the masses, really? Because, you know, you won't get too far if you don't get them on board.

  • Speaker #0

    Well, basically, the reason they attacked me was precisely because it was the reason I knew they would. Because the teachers, the math teachers, or the teachers didn't know how to program. And that's why I wanted to get the kids. Because if I get the kids, the kids will do it on their own anyway. They don't have to have a competent teacher. We know from, you know, from... years and years of experience. You give a kid a computer, okay, he may break it, but most likely he's going to figure it out much faster than older people. I mean, that's why I wanted to start young, so that I knew that, you know, I mean, basically, you know, educational reform to have an effect takes 15 to 20 years. I figured 15, 20 years, it's fine. Give them the computer now, and we'll see that, you know, there weren't enough qualified teachers to actually teach programming. The kids learn themselves. I mean, that was what I thought. That was what I hoped. And that's what happened. But the opposition was strong. Yeah. But well, basically, because of social pressure from parents saying, you know, we want our kids to have this, the opposition among other groups was lessened because the parents are the voters.

  • Speaker #1

    So the other large area you also had a role in is obviously the EU accession process. And that's a completely different story. It seems Estonia wasn't particularly interested in joining the European Union, right?

  • Speaker #0

    Well, Estonia itself was not interested, and most of Europe did not consider us a country that would ever join. And it was, you know, former Soviet Republic, blah, blah, blah. And the reason what Estonians didn't want to do is because they, because of our historical experience, experience getting invaded by the Soviets, invaded by the Nazis, invaded by again by the Soviets, and then 50 years of Soviet occupation was, we have to get into NATO. We have to get into NATO, NATO, NATO, NATO. And this was the attitude among basically all Eastern European countries. But there was a hope for Poland and the Czechs and the Hungarians that they could also join the EU. I mean, those countries also wanted only to get into... into NATO and all the other stuff, Moon cares. And Eastern Europeans were kind of anti-EU back then, kind of like, we don't need that socialist stuff or, I mean, whatever. On top of that, it became clear that certain countries, Germany first and foremost, were completely against our ever joining the EU even. So I thought about this. I was at the time, I was the ambassador in the United States. And I kept I kept getting these messages saying, forget it, forget it. You'll never get either one, especially not NATO. And then trying to figure out what do we do? I said, well, the problem with NATO, joining NATO, it is a strictly political decision. And so even if you could, you know, I could sort of schmooze the U.S. government to say, okay, we support you. I mean, because there were sympathetic people there, but, you know, they're still like, nah. But the opposition of... basically the large EU countries, I mean, Germany, first and foremost, France, Italy, UK at the time they were in the EU. I mean, in NATO, they would never let us in. But that's a political decision. Now, the EU, on the other hand, the decision as to whether, especially given the sort of the approach the EU took was, it was not political. It was, you have to meet certain criteria. They're very strict criteria. They're difficult criteria to meet. But I said, okay, we can do that. That's something we have agency in. We cannot change the political attitude regarding NATO. But we can change the attitude towards us based on our performance. There was some crisis in the Estonian government, and so I was appointed foreign minister. So since I'd been pushing this line, I said, okay, now we do this. The first meeting we had with the leadership of the foreign ministry was, I knew everyone, basically, you know, 15 people, different departments. And there was one person I didn't know. And it was this very young woman, I don't know, 23, 24. And I said, I don't know you. Who are you? And she goes, tell me your name. And I said, and what do you do? And I said, well, I run the European Integration Bureau. And I said, oh, how big is that? She said, I am the European Integration Bureau, which showed what the... foreign ministry's attitude towards joining the EU was. So I just completely changed that. I said, okay, we redo the budget. We don't have embassies. And like at that time, there are 12 countries in the EU. We opened all new embassies. We completely redid the whole approach to legislation, prioritizing which legislation gets done. Mirabile dicto. In 1997, when they came to decide who qualified, they chose six countries, and we were one of them, because our performance was like that. Now, I mean, that was just like, not in the cards that this would happen. But I mean, if you just push it and you do something that was weird, people came along and did it. Now, our two southern neighbors, Latvia and Lithuania, didn't have that kind of approach. Called me crazy. He said, you know, El-Wislam's on the EU. Why is he doing that? It's only in NATO that matters. But as it happened, I mean, the whole point of joining the EU, ultimately, and that was my nasty thought behind my mind, is that if we can get into the European Union, the other EU members in NATO can no longer veto us. So that basically eliminated all possible vetoes from the UK, Germany, France, Italy, and it basically left... three countries to convince. Turkey, Norway, well four, Iceland, not a problem, and the US. So if you get Canada, right, Canada, Norway, US, Iceland, and Turkey. Now, if those you get on board, you're it. And that's how we got into NATO. I mean, that was, again, it was something that the foreign ministry, when I became foreign minister, basically, as with the computers, it's crazy, This is stupid. This is not important, but I was foreign minister, so they didn't have any choice. So anyway, those are, I guess, the things that counted.

  • Speaker #1

    When I'm listening to these stories, I'm thinking that when a country wants to redefine itself, it really starts with clarity and intentionality. When was that moment when Estonia sort of stopped describing itself as a country in transition and began thinking in terms of designing the future? This is exactly where we are going. Do you remember that moment?

  • Speaker #0

    It happened in different parts of society at different times, I mean, different ministries. There were some that were very sort of forward-leaning, even resentful of this idea of transition. Today, you know, there's a yearly report that comes out, Nations in Transition, which is only about Eastern Europe. You know, I look at this, Estonia is like number two in the world in press freedom, number five in the world in social support for families. It's the only East European country that has legalized gay marriage. I mean, it is less corrupt than most of the EU. So And then I was like, what do you mean nations? Why don't you do a little transition for some of these other countries, right? Yeah, I mean, look at this. Estonia is number two in press freedom. You know what the U.S. is today? 57. I mean, it's like, come on. This whole idea of former Soviet republicans, like, that's a third of a century ago. We have completely changed. I don't want to hear it. So, I mean, the transition part. I mean, I started bugging me a lot earlier just because I would follow the statistics on who's where doing what. Then you look at these numbers and you go, you know, we're not there. I mean, we're not like those countries we should be transitioning to because we're better than they are. And that was kind of always annoying. Some of the problem was, I mean, they had to convince countries to do things like, well, we should we give you visa free travel to Europe? You know, what? So, I mean, all of that... As I said, it's changed dramatically, but it is, it's still, there is an attitude about Eastern Europe is like, oh, listen. Whereas, in fact, it's cleaner, less corrupt, better educated than most of Western Europe today. In fact, in non-Asian countries, that is outside Japan, Korea, Singapore, China, Taiwan. We have the best scores on math and language skills on the OECD PISA test, right? So our educational system is rather good, if that's the case, right? So all of that just shows that, you know, old stereotypes die hard. And I think if you ask, when did this whole idea of transition end? I think it ended with slowly realizing that in whatever your area is, you're actually at least as good, if not better. than the people who are sort of calling you a transitional venture.

  • Speaker #1

    So if you think about reinvention and transformation, it's really an ongoing process. It's not a one-off project. So when you think about Estonia, how do you think the country should or perhaps could reinvent itself right now?

  • Speaker #0

    And when I think about the direction things are going in, we have the big challenge is what happens to this little country in the era of AI? You know, we're small, right? I mean, we don't have that many people. How are we going to, I mean, we'll never be able to compete with the U.S. or China on this. On the other hand, being creative in using AI, you can do all kinds of stuff. One of the stories I tell a lot about is after I was president, I was invited to Stanford University because it was the center of IT in the world. So I go there. I mean, Stanford's very nice. I had to register my kid to go to school there. The way I did it, I had to take my electricity bill. I had to drive down to the headquarters of the school education department. I had to take a number to go in. I had to present my passport. I mean, 17 different documents all on paper. When I finally got to the person behind the desk, she took all the stack of papers, went over and photocopied them all. And then she came back, gave me the stuff back. And then... By hand, she started filling out, you know, whatever, from the photocopies, she started filling out these forms. I was kind of like, you know, Estonia, none of that happens. None of that, right? I mean, it's like, where do you live? We know where, I mean, you know, we know where you live. You get, because you're registered to live there and because it's Everest's birth and whenever you get, when the kid turns a certain age, you get a little email that says. By the way, September 1, school starts, and here's, you know, we give a little school supplies. Are the kids vaccinated? Medical records all exist. They're online. They can check to see. They can't see who you are, but they can see if you say, is this person vaccinated with the required vaccine? All of that's done. You know, this came up with my oldest son who came to the U.S. during COVID. And he got, he was there just for two weeks, but he got vaccinated. and you you came back and it is the yellow card. Here in Estonia, we had, in fact, Estonia was an Estonian company invented the app that is used all over Europe to show that you have been vaccinated because it checks. whether you are or not, without actually accessing your name and data, it just reports back saying, this person is vaccinated. And so he came back and he said, well, all right. And here he went to the doctor. Here, here's my little, my little card was filled out by hand saying vaccinated. What do I do with this? I mean, you know, you're not in the computer. So clearly in the United States, yeah, another example. It was only, I think in 2013, the U.S. military started using chips for two-factor authentication. I mean, we've been doing it for 13 years or so. And to this day, the US government, despite Doge, which is not what you have to know, Doge is not the way to do it. I mean, it's my son, my oldest son, who is now 37. Actually, because he grew up in this insane family, he was always like Anil Ander. Well, he eventually, he ended up being the CIO of the country. Well, he doesn't. published a paper for a German think tank. It's in English, but it's a German think tank, basically showing all of the issues you have to deal with in order to digitize or to use AI in a way that respects rights and freedoms and reform government. None of those are in Doge. No one thought they just went and just chopped things up as opposed to thinking it through. I mean, even the original. pre-AI period, it took us about three or four years to figure out all the legal connections that you have to make. I mean, who can see what? What kind of level of permission does a government official have to see something? Because certain things, you know, public health, you have to see something. People shouldn't be able to see your healthcare records. But on the other hand, in terms of, you know, if there's an epidemic or something, all these very difficult to find questions that must be defined by law. not you don't go in there with an axe and start cutting with and call yourself big balls what do you think estonia will sort of pivot what's next for estonia well i think that the way it'd be given the level of thinking here i think we probably will be one of the thought leaders on a use of ai in public services and that's one place where i think it could be most useful. All the other stuff. It could be a lot of fun and even all kinds of stuff. But as long as the citizen has to face traditional, usually undigitized, but even if slightly digitized government, I mean, what do I do? I want to get a fishing license. Well, I don't know. What do I do? I mean, I have to go get, I mean, I have to do something, whatever it is. I mean, we have part of this already working here since like 2000, which when I do my taxes, I get all my, I get my tax, they're filled out for me. everything's filled out everything i made everything all my charitable donations everything is in there and i did this we're sat there on the screen and you can check it all through and say is this right and it's always right it's always been and then you just press enter and your taxes are done right i mean so i mean the kinds of thing that to me we can foresee in the future is I mean, AI working out for companies. I mean, to think of government. as a service that government. So instead of going after a company that is, it hasn't paid its taxes because it's been, it's been in trouble. Instead, the AI will say, you know, your tax risk, your receipt, I mean, your income is not really meeting what your expenditures are and your loan obligations. And then maybe, maybe you should come and talk. to us, maybe we'll, you know, lighten your tax load so you get over this problem that you may not even know you have because, well, we do have sort of online reporting of all income and expenditures here. So we don't, I mean, we do quarterly reports if you want, but basically you can sign up and just everything happens digitally. So that information is there. It just could be sort of operationalized so that the tax department says, by the way, you know, doesn't look so good. Maybe we need to restructure your tax obligations and, you know, I mean, all these things that governments can do. Governments, I mean, sort of same thing with health care monitoring. I mean, if it's that it can notice, I mean, there's so many things that can notice it depending on how much you want to monitor. Right. I mean, there are ways of monitoring, constantly monitoring your level of health, your blood pressure, all these things can be done. And the AI will say... By the way, here, why don't you come in for something? That's where I see it going because, I mean, you're going to get amazing products from all kinds of huge companies whose yearly income is like a thousand times the GDP of my country. So I'm not worried about that. But it's the application side. And it's also my own experience with the level of application of the old digital revolution in other countries, which was none of it. really in public services. And it's especially true in the United States where, I mean, it doesn't really, you can't, the difference between what you can do, the amazing things that you can do with this here, compared to what private companies, compared to what I can do with in my country on here for whatever, filling out, I mean, applying for something, getting whatever. I mean, I can do it all night. Certainly, we've gotten to the point where the, until this year, there was only one thing you couldn't do online, which was get divorced. As of January 1, you can even get divorced online.

  • Speaker #1

    So I publish a weekly column that is focused on various aspects of reinvention. And I share articles that. discuss various topics and I ask questions. And there was one article from the Wall Street Journal recently saying that some AI models are already rewriting their own shutdown code. And this is because we're not teaching AI to think like us. We're teaching it to win. So my question was, what else are we handing over to machines that haven't truly understood what we meant, but will follow anyway? What are your thoughts about such trends and dangers that we're perhaps not seeing.

  • Speaker #0

    Well, what I have followed is this whole idea which has gone out of the United States in the last five months, which is that you collect all this data and put it into one place, which is something we specifically designed our system to compartmentalize everything. Now, aside from the security risks, I mean, you can actually, once you apply AI to these data, you can start finding out things that you probably wouldn't want to. You wouldn't want the government to know. And that's my worry is that, okay, the government then has a tool. I mean, especially because there's no legal basis for any of this. There's no law allowing the U.S. government to do what it just did in the past five months. In this country, you know, anything that changes the way anyone can look at data requires that legal foundation. And, you know, sort of going through the whole process, does this violate basic fundamental rights and privacy rights? Which makes it, you know, slower. On the other hand, we do it, which makes us feel a lot much safer.

  • Speaker #1

    So I want to go back to you now towards the end of the conversation. You've worked across a number of different identities. You were a journalist, diplomat, president, now a thought leader, an educator. How has your definition of reinvention or transformation changed across these roles?

  • Speaker #0

    Well, I don't know. I mean, basically every position I've been in, I've had some weird ideas and done things differently. It's always been like that, basically. I don't know. When I was at Radio Free Europe, I was head of the Estonian service. And then it was like 1988. And everyone was saying, oh, Glasnost perestroika. I was like 36 years old. No, I was like 34 years old. Yeah, 34 years old. I was head of the Estonian Serbs. I said, oh, well, how about I go visit the Estonian part of the Soviet Union? Now, I mean, for that, I mean, it was like, nope. The only people that ever got from Radio Free Europe to the Soviet Union were people who re-defected. So, but I said, you know, we should call them on their bluff. And then I went to my leadership, went up to Washington, you know, this crazy guy who wants to go to visit Estonia. And it took them like three months, right? I said, okay, you can try, but they won't let you in, right? Well, anyway, so as they said, okay, then I wrote to the so-called foreign minister of Estonia saying, by the way, in the spirit of Lasnost and Perestroika, you know, I say it's all open and free speech, and how about if you let me in? I mean, I like to visit. It's like, no, three months go by, you know, and then finally I get this notice. It's like, yeah, you can come. But then I went, I was in Munich. I went to the Soviet consulate there. They refused to give it to me. So I called them up. I said, what do you do? They said, well, I'll tell you what you do. Fly into Finland. And then you call this number. So, I mean, people were thinking out of the box in Estonia, too. This guy's KGB basically telling me, he says, call this number. And you meet this guy and give him your papers. And by the way, if he gets it done, give him a bottle of Western cognac. So that's what I did. I mean, I flew to Finland not knowing if I was going to get in. But I called up the guy and I gave him my papers and I got my visa and I gave him a bottle of Hennessy. It worked. But basically, you have to be, you know, if you remain constricted by the rules. You don't come up with new ideas, that's all. I mean, it just seemed like no one else had ready for your book. Oh, with Blasphemer's Perestroika, why don't we try this? It was just, I thought, well, it's kind of nuts, you know.

  • Speaker #1

    Okay, so what book is currently sitting on your bedside table?

  • Speaker #0

    New Mendelssohn translation of The Odyssey.

  • Speaker #1

    And I want to ask you before we close, if you could ask one deep, unsettling question of yourself, of leaders of the next generation, what would that be? What is the question that is still sort of challenging you specifically?

  • Speaker #0

    Oh, there's so many, I don't know. There's no single one. I mean, I would get... I was like, you know, what's your favorite color? Like, I don't know, one question. Well, I guess what I think about the most question, what I think about most is why is it after the complete victory of the Enlightenment and bettering, pulling us out of the Middle Ages and made a rational thought, scientific evidence, have we descended back into this sort of Again, I would say medieval conspiracy theory, rumor-based insanity that we see. And it's just so bizarre because, you know, you would never get this without the science that came out of the Enlightenment. But, well, they're the same thing. I remember reading, you know, 40 years ago, V.S. Naipaul's Among the Believers, you know, and you have this, like, total turn of Iran towards sort of medieval belief. Yet they all had modern weapons. I don't know how we got there that we've given up. So much of society, so many governments have abandoned the rational thought that from the 18th century on, well, maybe earlier, from the Renaissance on to through the Reformation and the Enlightenment, have brought us to a level of wealth, well-being, prosperity that was never, ever imagined. Thomas Hobbes said the life of a primitive man was nasty, brutish, and short. Well, I mean, how it stopped being nasty, brutish, and short was through science, evidence, rules, you know, all that. And yet we're turning against it. And that's what really shocks me.

  • Speaker #1

    Thomas, thank you so much for the conversation. I really enjoyed it. And I'm looking forward to meeting you in person.

  • Speaker #0

    Great. Well. If you're ever in Estonia, I would recommend doing it in the summer. All right. Great.

  • Speaker #1

    Thanks for joining me today. If today's story left you with a question or a quiet nudge, leave a comment or share the episode. Subscribe if you'd like to keep on listening. And remember, the next chapter doesn't always begin with a plan. Sometimes it starts with a pause.

Description

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

Stay connected

Subscribe to Inside Reinvention.
Follow Andrew Wrobel (website, Linkedin and Instagram) and Reinvantage (website, Linkedin, Instagram) for new episodes, tools, and research.


Hosted by Ausha. See ausha.co/privacy-policy for more information.

Transcription

  • Speaker #0

    This is the one thing where we are on a level playing field. Everything else, we're way behind. Just trying to do things a little differently. I don't know why, but I've always had this thing, let's try it differently, let's try something some different way. It did show me that having learned something like that at an early age was important. Then I used a quarter century later to help digitize my country. You know, if you remain constricted by the rules, you don't come up with new ideas. So much of society, so many governments have abandoned the rational thought, and that's what really shocks me.

  • Speaker #1

    This is Inside Reinvention. I am Andrew Robel, and in this series, I speak with people who have rewritten the rules, sometimes by choice, often by necessity. It's not about starting over, it's about seeing differently, choosing deliberately, and moving forward with clarity. My guest today is Tomas Hendrik Ilves, a former president of Estonia. He is widely credited with shaping one of the world's most ambitious digital societies. But that's the outcome. What I want to understand is the thinking that led there, the doubts, the decisions, and the moments of clarity that shaped not just a country, but the way we think and talk about digital future. This conversation isn't about looking back. It's about how reinvention begins, how it unfolds, and what it continues to demand from us. A very warm welcome to the first episode of Inside Reinvention. Thomas, it's so great to have you here.

  • Speaker #0

    Well, we'll see. The first time, we'll see how it goes.

  • Speaker #1

    Okay, so before we talk about the title, before we talk about the impact, when you were still very, very young... You know, you were trying to imagine your place in the world. Who are you trying to become?

  • Speaker #0

    I don't know if I really did want to become anyone. I was just, I was more involved in just things that interested me rather than having a future goal. From a very early age, I didn't want to know as much as possible about everything. That was kind of the, I don't know. I mean, I was always reading stuff, you know, asking questions and. From an early age, I had, I mean, which was illusory, but I thought I had like a different way of looking at things. Had to write a paper in high school or something. I would come up with a new thesis and people would look at me weird. And then sometimes they'd go, well, anyway, I mean, it was basically just trying to do things a little differently. I don't know why, but I've always had this thing. Let's try it differently. Let's try something some different way. And probably I would say, you know, being self-deprecating, that I didn't think I could do it the way... everyone else was doing it, so I might as well try some other way. I think that's, you know, sort of imposter syndrome or something.

  • Speaker #1

    And do you remember your first job, the one you actually got paid for?

  • Speaker #0

    It's hard to say if it was a job. I did stuff that I got paid for, but it was nothing, nothing much. The only relevant job I would say that I had that, I mean, was not my first, but which showed me something that was really important for my later life. I mean, it was something I learned in college. But when I was 17, 16, 17, I had a brilliant math teacher who was doing her PhD at Columbia Teachers College in education. And her idea was, let's see if we could teach kids to program or code. This was in 1971. And so she did this, had this class of 12 of us, and she taught us basic. which is baby Fortran. I mean, she was still today, but at that time, it was, like I looked it up later, it had only been invented a year earlier. And she went and rented a Teletype machine with a Perfo tape, like a long yellow tape. No one remembers these things, but okay. It was, and then we had a big telephone modem. You take, you know, the old phone, you stick it into the, in there, and then it was connected. It was dial-up. connected to a mainframe computer, basically 50 kilometers or 30 miles away. And then we had a little budget to be able to do stuff. The reason you used the Perfotate was that you would basically test out your programs and write them there. And so I learned the code in BASIC. Well, okay. I mean, it was, I didn't think about it. All the other, the boys in the class, other boys in the class, they're all like tech millionaires today. I never, you know, I didn't do that. But then I went to, when I was an undergraduate, I saw a little ad back in the day when they had three-by-five-inch file cards that said, on the bulletin board, programmer, 10 hours, 10 to 15 hours a week in the site department. I said, oh, I know how to program. So I went there, and then it turned out. It was. Professor had bought, I think, the first commercially available lab computer, which was a PDP-8 put up by DEC, which is long out of business, Digital Equipment Corporation. It had 8K of memory. 8K, that's as much as an empty email today, right? But because it had 8K memory, and I have no recollection of what the processor was at the time, but I had a... program in assembler language, which is hexadecimal. I mean, base 16, zero through nine, A, B, C, D, E, F. But program is program. You just, instead of saying go to or whatever you do right on the higher level language, you just write the numbers in. And I said, wow, I could know program because basically it's the language itself is ultimately irrelevant. So that was what I really learned. I was making minimum wage, which at that That time was, I guess, $2.15 an hour. It was a long time ago. That was an interesting lesson. Otherwise, I mean, I had jobs doing stuff, but I mean, that was kind of meh. It wasn't anything where you had any engagement in a serious way or any real agency, but that at least, I mean, you didn't have much agency there either. I just had to sort of figure out how to program this computer. But it did show me that. having learned something like that at an early age was important, which then I used a quarter century later to help digitize my country, which we can get to later on.

  • Speaker #1

    Yeah. So speaking about that, I mean, you mentioned thinking out of the box or maybe even considering there was no box in the first place. And you mentioned Estonia. So before you became president, you have done some amazing stuff for the country. And we're talking about two different things, right? The first one is the digitalization. And we know that 100% of public services right now in Estonia have been digital for quite some time. But the other thing is having Estonia in the EU, which was not something people envisioned at the time, right?

  • Speaker #0

    Well, the digitalization came first. I mean, basically, it was a result of the extreme poverty of Estonia once it became independent again. It had been independent before World War II. And if you read, you'll find in volume two, the Cambridge economic history of Europe, little bar graph, and then it has GDP per capita of countries in Europe. And there it said Estonia had a slightly higher GDP per capita than Finland. That was in 1938, the last full year before World War II when everything went to hell. In 1939, the Finns were invaded, all this. So 1938 is like the last time to look at the countries. The next time, if you look at the GDP per capita of Estonian Finland in 1992, which was the first full year of our independence on our part, then the GDP of Finland at the time, the nominal GDP per capita nominal was $23,800. So basically $24,000 per person. The GDP per capita. of Estonia was 2,800. So basically, Finns had become in the interim eight and a half times richer. Now, what that meant? Well, I mean, I was invited to become, I had U.S. citizenship, I was working at Radio Free Europe, and then the president of the country after our first democratic election said, look, what are you doing over there? You know, come on, let's go come work and help build up the country. I said, okay. I didn't realize how much I was. What a cut in pay I would take. So I went to Washington. I was the ambassador. And we were so poor that there were times when they wouldn't send money from our country, from Estonia, to pay us. So then we'd live another three weeks on credit cards. And I was like, what do we do? How do we get out of this poverty? And the thing about the two aspects of poverty, which I want to talk about, one is that even the GDP figures per capita don't even say enough. because in the interim, we have not built... highway. We have not built, you know, modern hospitals. The buildings are all falling apart. The basic state of the country is much poorer, even if you eliminate the income differences. So because they've had 50 years of development, which we had not had. And the other problem was take from Zeno's paradox of Achilles and the turtle. One of his paradoxes, but it's, But, you know, it's like when the turtle starts going. then the fastest man in earth in Greek mythology, Achilles, by the time he catches up to where the turtle was, the turtle has moved on. Now, what that means in GDP. per capita or GDP, is that, okay, I mean, if Finland starts off at 24,000 US dollars per capita and they have a miserable year of 1% growth, and Estonia has an incredible 8% growth, which is a phenomenal growth rate, we would still lag more behind than we were before. So this is the fundamental problem of development. At home here in Estonia, where I am right now, there were all kinds of theories about what we should do. And so they were like the left, the hard left. They said we should just keep on with communism. And then you had the hard right saying, oh, we should become Singapore. And it was all basic sort of classic economic theory. I saw it differently, though. I mean, first of all, I was just as lost. And I was going, you know, it showed up when you couldn't pay any for anything. because I've been a geek. Because I learned to code when I was 17. And then people knew that and they'd known me. I dealt with this stuff, played around with it even before anything real happened. I bought my first Apple IIe in 1983 or something. So I played around. People thought I was a little weird. So a friend of mine sent me an email. And I was one of the few people who had emails even then. But I said, OK. And he sent me an email and said, look, check. this thing out. And what he told me to check out was Mosaic, which is the first ever web browser invented by Mark Andreessen, who was then a graduate student at Champaign-Urbana, University of Illinois, Champaign-Urbana. And the reason why a web browser was important was that even though Tim Berners-Lee invented... the hypertext transfer protocol or HTTP in 1989, it was not usable because if you know, if you look at your usual URL, it's just like a long string, alphabetical string of figures and numbers. But here, this was, if you put in the New York times, it would bring you to the New York times, but I didn't know that yet. So it seems he was a friend of mine. I said, go buy this and see what you think. And then, so I, back then I went to RadioShack, which is also out of business now along with that. And I bought... for, I don't know, $29.95, this like cardboard thing with seven floppy disks. It was just, I remember it was just big because, you know, they thought people would steal it or something. So I bought this seven floppy disks. You upload it, you know, and these days you download, for free, you download these amazing browsers. But, you know, then, and I upload, so I got this web browser and then I sort of see what it does. And I go, this is the one thing. where we are on a level playing field. Everything else, we're way behind. Roads, hospitals, telecommunications, everything, we're way behind. This is one area where, and then I looked at the numbers, basically, I mean, no one had anything. I mean, the U.S. was sort of in the lead, but in terms of the statistics you had then were actually a number of websites. But it was like everyone was behind. So the first thing I said, okay, what we got to do, if we really want to win, we got to pick a thing where we are on a level playing field with everyone else. And then I said, okay, how are we going to do that? And I figured the country's full of sticks in the mud. And they're like, what are you talking about? This is crazy. No way. Which was, in fact, the case. The other thing that, you know, I brought in this other knowledge, which was basically there had been in my country in the 1920s, this huge. language reform and and the way it was done which had we had got all these new words changed the old grammar did all this stuff and the way it was done was that there was this genius who was the sort of the guy who created these new terms to deal with the modern era he just made the book the elementary school text that all kids had to learn with a little thing in there saying if your teacher tells you otherwise don't listen to him but anyway so what happened was that 20 years after Afterwards, all the old words were forgotten, and the new words were what everyone thought were always being used. I said, this is what we got to do. We get the young people. And so I said, okay, what we should do is put computers, computer banks in every school. And on top of that, the government doesn't pay for all of them. Because another thing I once read somewhere, anyway, basically, you have to have skin in the game. There's a great example from like... Forty years ago, when the first computer games came out, then some sort of experimental psychologists realized that the skills involved in computer games were the same ones that were very, that translated into fighter pilots' skills. So then they put all these computer games in fighter pilots' barracks, and they just gathered dust. So then the Air Force went to some consulting company and said, what do we do? They said, oh, very simple. Just put a little slot in there and make them pay a quarter. And as soon as they did that, all the fighter pilots were lining up to be able to play the game. Because as long as it's free, it's like, ah, you know, who cares? So when I said, okay, how do we do this? I said, I explained to the government what we do is municipal governments, because that's the level of education here. They, you know, your town or village pays for, you know, for deal, I guess, the budget to deal with education. I said half for anyone who wants it. Well, the government pay for half. You kind of come up with the other half. So in the beginning, like there are four or five schools with some, you know, young, bright math teachers that we got to do this. And then the other wonderful motivator. as I predicted, the motivator of human behavior, envy kicked in. And so if you have a little township here, like, you know, it's got like 5,000 people in it, then they have like, you have the ones around it. And so what happened was the one would get it, and then all the other people around would say, how come they have that? We don't. Which they would then go to their board of education and say, we want that thing that they have there. What that meant was, I mean, the program took me from 93 to 95. to convince the government. And at those years, I was like, I mean, basically the Teachers Union newspaper did not, I mean, which is a weekly, did not, there was not an issue that did not attack me for one way or another from this idea as being completely stupid, ridiculous, the enemy of the culture, all this crap. Anyway, so we got the government to do it in 96. By the end of 98, 99, night. All Estonian schools were digital. If you fast forward from that 20 years, I was in my last year of my presidency, and I always go to startups, you know, just to pat them on the head and say, you're great. This is wonderful. And I started asking them, how did you get into this? Why are you doing this? You know, whatever you're doing, you're a startup. And I started counting them up. Basically, 80% of the time of these startups, people would say. oh, I was a kid in your program. So now they were like, you know, 32, 35. They've been coding for 20 years. So that's part of my explanation for why Estonia has the highest number of unicorns per capita, which we have one for every 133 people, 133,000 people in the country. I think Israel's number two. They're like one unicorn for every, I don't know. 800,000. But anyway, just the per capita, the highest number of unicorns and everyone. I mean, all of that's how we later on, once this thing started really going and that became like a thing and people, the government started trying sort of elementary digitization long before anyone else. The banks came up with electronic banking, which was better than anyone else's in the area. I mean, they ended up being taken by, you know, Swedish. banks to come and do theirs. And then what happened basically, and this is where it goes beyond me. I mean, I kickstarted it, but the much smarter people than I am figured out that if you really want to do digitization properly, you need to have a secure, unique identity for every person. You need to have a secure architecture. And then what came out of that is what we have in Estonia today, which is probably the most, I mean, with possible, you know, with maybe competing with Singapore, the most digitized government and public services anywhere. Even that, I mean, I guess the Estonian sort of approach that was kind of similar to what I did, I mean, sort of mentally, which was that they thought of the system we have as now it's been taken over by about 25 countries, more or less, to varying degrees. The thing that was unique, and this we can talk about later on when it comes to AI, is that we only invented one small part of that. All the rest existed. In fact, the unique identity part had existed for 25 years, since 1975, which was a chip card, which would allow you to do two-factor authentication, which is now common everywhere. I mean, all credit cards today, even in the US, chip. But back then, no one ever heard of it. Now, the thing is that you take something that's been around, a chip card or a chip in a car, basically, and you use it in a completely different way. And it provides you with something that no one else has. And so, too, with the architecture, which was invented locally, but it was invented by these kids in the university. I mean, they're 20-year-olds. And they said, OK. What we really need is a distributed data exchange layer so we have, you know, we don't have a single database anywhere that it can be hacked. You know, the worst case of that is the... OPM or Office of Personal Management hack in the US where they stuck everything in one place and everything was sucked out. Whereas in my country, all the data is individual. I mean, sort of my, here I have my driver's record, here's my health record, here's someone else's health record, here's someone else. So basically, the worst that can happen if someone breaks into the system, if they manage, is to get one cell, which would be, say, my... my health record you know even that would be bad but the point is it's not like when you someone hacks into the u.s government master file of all federal employees and you find you get things such as the you know the psychological profiles of cia officers and the home addresses of fbi agents i mean all the stuff that was just stolen because it's all dumped into one so that was the beginning of the that digitization program but you know so basically for you I would say what lessons learned one is have a broad range of experiences and readings so you can put things together and then use it in a different way.

  • Speaker #1

    I want to ask you about that resistance because you mentioned the teachers union paper that would criticize you every single week. What would be your advice that you'd share with leaders who actually have some brilliant ideas so that at least they think that they can do something differently and they need. to convince the crowd or the masses, really? Because, you know, you won't get too far if you don't get them on board.

  • Speaker #0

    Well, basically, the reason they attacked me was precisely because it was the reason I knew they would. Because the teachers, the math teachers, or the teachers didn't know how to program. And that's why I wanted to get the kids. Because if I get the kids, the kids will do it on their own anyway. They don't have to have a competent teacher. We know from, you know, from... years and years of experience. You give a kid a computer, okay, he may break it, but most likely he's going to figure it out much faster than older people. I mean, that's why I wanted to start young, so that I knew that, you know, I mean, basically, you know, educational reform to have an effect takes 15 to 20 years. I figured 15, 20 years, it's fine. Give them the computer now, and we'll see that, you know, there weren't enough qualified teachers to actually teach programming. The kids learn themselves. I mean, that was what I thought. That was what I hoped. And that's what happened. But the opposition was strong. Yeah. But well, basically, because of social pressure from parents saying, you know, we want our kids to have this, the opposition among other groups was lessened because the parents are the voters.

  • Speaker #1

    So the other large area you also had a role in is obviously the EU accession process. And that's a completely different story. It seems Estonia wasn't particularly interested in joining the European Union, right?

  • Speaker #0

    Well, Estonia itself was not interested, and most of Europe did not consider us a country that would ever join. And it was, you know, former Soviet Republic, blah, blah, blah. And the reason what Estonians didn't want to do is because they, because of our historical experience, experience getting invaded by the Soviets, invaded by the Nazis, invaded by again by the Soviets, and then 50 years of Soviet occupation was, we have to get into NATO. We have to get into NATO, NATO, NATO, NATO. And this was the attitude among basically all Eastern European countries. But there was a hope for Poland and the Czechs and the Hungarians that they could also join the EU. I mean, those countries also wanted only to get into... into NATO and all the other stuff, Moon cares. And Eastern Europeans were kind of anti-EU back then, kind of like, we don't need that socialist stuff or, I mean, whatever. On top of that, it became clear that certain countries, Germany first and foremost, were completely against our ever joining the EU even. So I thought about this. I was at the time, I was the ambassador in the United States. And I kept I kept getting these messages saying, forget it, forget it. You'll never get either one, especially not NATO. And then trying to figure out what do we do? I said, well, the problem with NATO, joining NATO, it is a strictly political decision. And so even if you could, you know, I could sort of schmooze the U.S. government to say, okay, we support you. I mean, because there were sympathetic people there, but, you know, they're still like, nah. But the opposition of... basically the large EU countries, I mean, Germany, first and foremost, France, Italy, UK at the time they were in the EU. I mean, in NATO, they would never let us in. But that's a political decision. Now, the EU, on the other hand, the decision as to whether, especially given the sort of the approach the EU took was, it was not political. It was, you have to meet certain criteria. They're very strict criteria. They're difficult criteria to meet. But I said, okay, we can do that. That's something we have agency in. We cannot change the political attitude regarding NATO. But we can change the attitude towards us based on our performance. There was some crisis in the Estonian government, and so I was appointed foreign minister. So since I'd been pushing this line, I said, okay, now we do this. The first meeting we had with the leadership of the foreign ministry was, I knew everyone, basically, you know, 15 people, different departments. And there was one person I didn't know. And it was this very young woman, I don't know, 23, 24. And I said, I don't know you. Who are you? And she goes, tell me your name. And I said, and what do you do? And I said, well, I run the European Integration Bureau. And I said, oh, how big is that? She said, I am the European Integration Bureau, which showed what the... foreign ministry's attitude towards joining the EU was. So I just completely changed that. I said, okay, we redo the budget. We don't have embassies. And like at that time, there are 12 countries in the EU. We opened all new embassies. We completely redid the whole approach to legislation, prioritizing which legislation gets done. Mirabile dicto. In 1997, when they came to decide who qualified, they chose six countries, and we were one of them, because our performance was like that. Now, I mean, that was just like, not in the cards that this would happen. But I mean, if you just push it and you do something that was weird, people came along and did it. Now, our two southern neighbors, Latvia and Lithuania, didn't have that kind of approach. Called me crazy. He said, you know, El-Wislam's on the EU. Why is he doing that? It's only in NATO that matters. But as it happened, I mean, the whole point of joining the EU, ultimately, and that was my nasty thought behind my mind, is that if we can get into the European Union, the other EU members in NATO can no longer veto us. So that basically eliminated all possible vetoes from the UK, Germany, France, Italy, and it basically left... three countries to convince. Turkey, Norway, well four, Iceland, not a problem, and the US. So if you get Canada, right, Canada, Norway, US, Iceland, and Turkey. Now, if those you get on board, you're it. And that's how we got into NATO. I mean, that was, again, it was something that the foreign ministry, when I became foreign minister, basically, as with the computers, it's crazy, This is stupid. This is not important, but I was foreign minister, so they didn't have any choice. So anyway, those are, I guess, the things that counted.

  • Speaker #1

    When I'm listening to these stories, I'm thinking that when a country wants to redefine itself, it really starts with clarity and intentionality. When was that moment when Estonia sort of stopped describing itself as a country in transition and began thinking in terms of designing the future? This is exactly where we are going. Do you remember that moment?

  • Speaker #0

    It happened in different parts of society at different times, I mean, different ministries. There were some that were very sort of forward-leaning, even resentful of this idea of transition. Today, you know, there's a yearly report that comes out, Nations in Transition, which is only about Eastern Europe. You know, I look at this, Estonia is like number two in the world in press freedom, number five in the world in social support for families. It's the only East European country that has legalized gay marriage. I mean, it is less corrupt than most of the EU. So And then I was like, what do you mean nations? Why don't you do a little transition for some of these other countries, right? Yeah, I mean, look at this. Estonia is number two in press freedom. You know what the U.S. is today? 57. I mean, it's like, come on. This whole idea of former Soviet republicans, like, that's a third of a century ago. We have completely changed. I don't want to hear it. So, I mean, the transition part. I mean, I started bugging me a lot earlier just because I would follow the statistics on who's where doing what. Then you look at these numbers and you go, you know, we're not there. I mean, we're not like those countries we should be transitioning to because we're better than they are. And that was kind of always annoying. Some of the problem was, I mean, they had to convince countries to do things like, well, we should we give you visa free travel to Europe? You know, what? So, I mean, all of that... As I said, it's changed dramatically, but it is, it's still, there is an attitude about Eastern Europe is like, oh, listen. Whereas, in fact, it's cleaner, less corrupt, better educated than most of Western Europe today. In fact, in non-Asian countries, that is outside Japan, Korea, Singapore, China, Taiwan. We have the best scores on math and language skills on the OECD PISA test, right? So our educational system is rather good, if that's the case, right? So all of that just shows that, you know, old stereotypes die hard. And I think if you ask, when did this whole idea of transition end? I think it ended with slowly realizing that in whatever your area is, you're actually at least as good, if not better. than the people who are sort of calling you a transitional venture.

  • Speaker #1

    So if you think about reinvention and transformation, it's really an ongoing process. It's not a one-off project. So when you think about Estonia, how do you think the country should or perhaps could reinvent itself right now?

  • Speaker #0

    And when I think about the direction things are going in, we have the big challenge is what happens to this little country in the era of AI? You know, we're small, right? I mean, we don't have that many people. How are we going to, I mean, we'll never be able to compete with the U.S. or China on this. On the other hand, being creative in using AI, you can do all kinds of stuff. One of the stories I tell a lot about is after I was president, I was invited to Stanford University because it was the center of IT in the world. So I go there. I mean, Stanford's very nice. I had to register my kid to go to school there. The way I did it, I had to take my electricity bill. I had to drive down to the headquarters of the school education department. I had to take a number to go in. I had to present my passport. I mean, 17 different documents all on paper. When I finally got to the person behind the desk, she took all the stack of papers, went over and photocopied them all. And then she came back, gave me the stuff back. And then... By hand, she started filling out, you know, whatever, from the photocopies, she started filling out these forms. I was kind of like, you know, Estonia, none of that happens. None of that, right? I mean, it's like, where do you live? We know where, I mean, you know, we know where you live. You get, because you're registered to live there and because it's Everest's birth and whenever you get, when the kid turns a certain age, you get a little email that says. By the way, September 1, school starts, and here's, you know, we give a little school supplies. Are the kids vaccinated? Medical records all exist. They're online. They can check to see. They can't see who you are, but they can see if you say, is this person vaccinated with the required vaccine? All of that's done. You know, this came up with my oldest son who came to the U.S. during COVID. And he got, he was there just for two weeks, but he got vaccinated. and you you came back and it is the yellow card. Here in Estonia, we had, in fact, Estonia was an Estonian company invented the app that is used all over Europe to show that you have been vaccinated because it checks. whether you are or not, without actually accessing your name and data, it just reports back saying, this person is vaccinated. And so he came back and he said, well, all right. And here he went to the doctor. Here, here's my little, my little card was filled out by hand saying vaccinated. What do I do with this? I mean, you know, you're not in the computer. So clearly in the United States, yeah, another example. It was only, I think in 2013, the U.S. military started using chips for two-factor authentication. I mean, we've been doing it for 13 years or so. And to this day, the US government, despite Doge, which is not what you have to know, Doge is not the way to do it. I mean, it's my son, my oldest son, who is now 37. Actually, because he grew up in this insane family, he was always like Anil Ander. Well, he eventually, he ended up being the CIO of the country. Well, he doesn't. published a paper for a German think tank. It's in English, but it's a German think tank, basically showing all of the issues you have to deal with in order to digitize or to use AI in a way that respects rights and freedoms and reform government. None of those are in Doge. No one thought they just went and just chopped things up as opposed to thinking it through. I mean, even the original. pre-AI period, it took us about three or four years to figure out all the legal connections that you have to make. I mean, who can see what? What kind of level of permission does a government official have to see something? Because certain things, you know, public health, you have to see something. People shouldn't be able to see your healthcare records. But on the other hand, in terms of, you know, if there's an epidemic or something, all these very difficult to find questions that must be defined by law. not you don't go in there with an axe and start cutting with and call yourself big balls what do you think estonia will sort of pivot what's next for estonia well i think that the way it'd be given the level of thinking here i think we probably will be one of the thought leaders on a use of ai in public services and that's one place where i think it could be most useful. All the other stuff. It could be a lot of fun and even all kinds of stuff. But as long as the citizen has to face traditional, usually undigitized, but even if slightly digitized government, I mean, what do I do? I want to get a fishing license. Well, I don't know. What do I do? I mean, I have to go get, I mean, I have to do something, whatever it is. I mean, we have part of this already working here since like 2000, which when I do my taxes, I get all my, I get my tax, they're filled out for me. everything's filled out everything i made everything all my charitable donations everything is in there and i did this we're sat there on the screen and you can check it all through and say is this right and it's always right it's always been and then you just press enter and your taxes are done right i mean so i mean the kinds of thing that to me we can foresee in the future is I mean, AI working out for companies. I mean, to think of government. as a service that government. So instead of going after a company that is, it hasn't paid its taxes because it's been, it's been in trouble. Instead, the AI will say, you know, your tax risk, your receipt, I mean, your income is not really meeting what your expenditures are and your loan obligations. And then maybe, maybe you should come and talk. to us, maybe we'll, you know, lighten your tax load so you get over this problem that you may not even know you have because, well, we do have sort of online reporting of all income and expenditures here. So we don't, I mean, we do quarterly reports if you want, but basically you can sign up and just everything happens digitally. So that information is there. It just could be sort of operationalized so that the tax department says, by the way, you know, doesn't look so good. Maybe we need to restructure your tax obligations and, you know, I mean, all these things that governments can do. Governments, I mean, sort of same thing with health care monitoring. I mean, if it's that it can notice, I mean, there's so many things that can notice it depending on how much you want to monitor. Right. I mean, there are ways of monitoring, constantly monitoring your level of health, your blood pressure, all these things can be done. And the AI will say... By the way, here, why don't you come in for something? That's where I see it going because, I mean, you're going to get amazing products from all kinds of huge companies whose yearly income is like a thousand times the GDP of my country. So I'm not worried about that. But it's the application side. And it's also my own experience with the level of application of the old digital revolution in other countries, which was none of it. really in public services. And it's especially true in the United States where, I mean, it doesn't really, you can't, the difference between what you can do, the amazing things that you can do with this here, compared to what private companies, compared to what I can do with in my country on here for whatever, filling out, I mean, applying for something, getting whatever. I mean, I can do it all night. Certainly, we've gotten to the point where the, until this year, there was only one thing you couldn't do online, which was get divorced. As of January 1, you can even get divorced online.

  • Speaker #1

    So I publish a weekly column that is focused on various aspects of reinvention. And I share articles that. discuss various topics and I ask questions. And there was one article from the Wall Street Journal recently saying that some AI models are already rewriting their own shutdown code. And this is because we're not teaching AI to think like us. We're teaching it to win. So my question was, what else are we handing over to machines that haven't truly understood what we meant, but will follow anyway? What are your thoughts about such trends and dangers that we're perhaps not seeing.

  • Speaker #0

    Well, what I have followed is this whole idea which has gone out of the United States in the last five months, which is that you collect all this data and put it into one place, which is something we specifically designed our system to compartmentalize everything. Now, aside from the security risks, I mean, you can actually, once you apply AI to these data, you can start finding out things that you probably wouldn't want to. You wouldn't want the government to know. And that's my worry is that, okay, the government then has a tool. I mean, especially because there's no legal basis for any of this. There's no law allowing the U.S. government to do what it just did in the past five months. In this country, you know, anything that changes the way anyone can look at data requires that legal foundation. And, you know, sort of going through the whole process, does this violate basic fundamental rights and privacy rights? Which makes it, you know, slower. On the other hand, we do it, which makes us feel a lot much safer.

  • Speaker #1

    So I want to go back to you now towards the end of the conversation. You've worked across a number of different identities. You were a journalist, diplomat, president, now a thought leader, an educator. How has your definition of reinvention or transformation changed across these roles?

  • Speaker #0

    Well, I don't know. I mean, basically every position I've been in, I've had some weird ideas and done things differently. It's always been like that, basically. I don't know. When I was at Radio Free Europe, I was head of the Estonian service. And then it was like 1988. And everyone was saying, oh, Glasnost perestroika. I was like 36 years old. No, I was like 34 years old. Yeah, 34 years old. I was head of the Estonian Serbs. I said, oh, well, how about I go visit the Estonian part of the Soviet Union? Now, I mean, for that, I mean, it was like, nope. The only people that ever got from Radio Free Europe to the Soviet Union were people who re-defected. So, but I said, you know, we should call them on their bluff. And then I went to my leadership, went up to Washington, you know, this crazy guy who wants to go to visit Estonia. And it took them like three months, right? I said, okay, you can try, but they won't let you in, right? Well, anyway, so as they said, okay, then I wrote to the so-called foreign minister of Estonia saying, by the way, in the spirit of Lasnost and Perestroika, you know, I say it's all open and free speech, and how about if you let me in? I mean, I like to visit. It's like, no, three months go by, you know, and then finally I get this notice. It's like, yeah, you can come. But then I went, I was in Munich. I went to the Soviet consulate there. They refused to give it to me. So I called them up. I said, what do you do? They said, well, I'll tell you what you do. Fly into Finland. And then you call this number. So, I mean, people were thinking out of the box in Estonia, too. This guy's KGB basically telling me, he says, call this number. And you meet this guy and give him your papers. And by the way, if he gets it done, give him a bottle of Western cognac. So that's what I did. I mean, I flew to Finland not knowing if I was going to get in. But I called up the guy and I gave him my papers and I got my visa and I gave him a bottle of Hennessy. It worked. But basically, you have to be, you know, if you remain constricted by the rules. You don't come up with new ideas, that's all. I mean, it just seemed like no one else had ready for your book. Oh, with Blasphemer's Perestroika, why don't we try this? It was just, I thought, well, it's kind of nuts, you know.

  • Speaker #1

    Okay, so what book is currently sitting on your bedside table?

  • Speaker #0

    New Mendelssohn translation of The Odyssey.

  • Speaker #1

    And I want to ask you before we close, if you could ask one deep, unsettling question of yourself, of leaders of the next generation, what would that be? What is the question that is still sort of challenging you specifically?

  • Speaker #0

    Oh, there's so many, I don't know. There's no single one. I mean, I would get... I was like, you know, what's your favorite color? Like, I don't know, one question. Well, I guess what I think about the most question, what I think about most is why is it after the complete victory of the Enlightenment and bettering, pulling us out of the Middle Ages and made a rational thought, scientific evidence, have we descended back into this sort of Again, I would say medieval conspiracy theory, rumor-based insanity that we see. And it's just so bizarre because, you know, you would never get this without the science that came out of the Enlightenment. But, well, they're the same thing. I remember reading, you know, 40 years ago, V.S. Naipaul's Among the Believers, you know, and you have this, like, total turn of Iran towards sort of medieval belief. Yet they all had modern weapons. I don't know how we got there that we've given up. So much of society, so many governments have abandoned the rational thought that from the 18th century on, well, maybe earlier, from the Renaissance on to through the Reformation and the Enlightenment, have brought us to a level of wealth, well-being, prosperity that was never, ever imagined. Thomas Hobbes said the life of a primitive man was nasty, brutish, and short. Well, I mean, how it stopped being nasty, brutish, and short was through science, evidence, rules, you know, all that. And yet we're turning against it. And that's what really shocks me.

  • Speaker #1

    Thomas, thank you so much for the conversation. I really enjoyed it. And I'm looking forward to meeting you in person.

  • Speaker #0

    Great. Well. If you're ever in Estonia, I would recommend doing it in the summer. All right. Great.

  • Speaker #1

    Thanks for joining me today. If today's story left you with a question or a quiet nudge, leave a comment or share the episode. Subscribe if you'd like to keep on listening. And remember, the next chapter doesn't always begin with a plan. Sometimes it starts with a pause.

Share

Embed