PILOT: EveryCity Whispers Pilot (Episode 0)

In this pilot episode, I explain the premise behind EveryCity Whispers and introduce myself. I also read excerpts from Paul Graham's essay, Cities and Ambition, which helped me frame what I'd like to cover with this show.

Background music credit: Long Season (Live) by Fishmans

TRANSCRIPT

There's a tiny sushi shop near my apartment in Tokyo. I've been going there once a week for a few years now. The master behind the counter, easily in his 80s, still makes every piece himself, one by one.

One day, I finally got the nerve to ask him in my clumsy Japanese how long he's been making sushi. He smiled and said, 55 years beginner.

Fifty-five years and I'm still a beginner. I'm still learning.

About 10 years ago, I co-founded a startup called Sideview. Back then, my understanding of startups was, we could just say, naive. I thought if you build something great and share it with enough enthusiasm, everything will fall into place. We spent nearly a year iterating and tweaking our app before ever putting it out into the wild. We thought that's what great craft demanded.

Not surprisingly, the business failed, but not without a few highs along the way. We did get an invite to WebSummit, which is one of the biggest tech conferences in the world, as part of their Alpha program. This basically means we got a free ticket, no travel expenses provided or anything. I still remember paying my own way to Dublin and Couchsurfing while I was there with a dude from Brazil named Reinaldo who was in Ireland studying English.

But we got a chance to short pitch a bunch of investors at the event. Basically like startup investor speed dating. And I distinctly remember a few asking me about our development process. And being naive as I was, I proudly talked about how we had tweaked and tweaked. It was basically like I was bringing my own thoughtful haiku to a rap battle. I misread the brief and completely committed.

It turns out that the tech world, which I'll basically equate with Silicon Valley, doesn't admire patience or mastery, no. It says, in no unclear terms, move faster, scale faster, disrupt, and win faster. That's a totally different message than what I've heard from Tokyo…master your craft… where deliberation itself can be a source of pride.

Japan is the fifth country I've lived and worked in on five different continents, and I've traveled to about 80 countries. I've practically made a living out of pushing my comfort zone and figuring out how to adapt. And I've spent shamefully little time to pause and reflect along the way.

But when I do, I realize every city whispers something to you. And most of the time, we don't even notice. That's what has led me here to kicking off this project, Every City Whispers, a deep dive into the invisible messages cities send us. The ones shaping who we are, what we value, and what we chase. Like a few flights I've taken in my life, I'm not totally sure where this one will land. But I've learned that's sometimes the best way to start. And I really appreciate you being along for the ride with me to find out.

There's a really interesting essay called “Cities and Ambition” by Paul Graham, who argues that great cities send you messages. New York, you should make more money. I don't care how you got it, but you should have more money. In San Francisco, eh, your money's nice, but you should have more power. That's what really matters. In Paris, ditch the sweats, ditch the athleisure. You need to dress better. I'll dig more into Graham's essay later, but basically, he suggests that we should go to the city that matches the ambition we already have.

I love Graham's essay so much that it inspired me to start this podcast, but there's a twist that I want to explore. What if the most important thing isn’t finding the place that echoes your ambition, but exploring the cities that challenge it? What if you could learn from the unspoken messages of every great city, the hustle of Sao Paulo, the discipline of Tokyo, the sensibility of Amsterdam… and bring them to you? What if we could take the ambition any city, every city, rewards and apply that energy into our own lives? That's what this project is all about . This isn't a travel podcast, but a way of thinking about cities. Each episode will dig into the question, "What does this city want from us? And what should we give to it?"

Some cities are in your face, suffocating you, while others are much more subtle and seductive. But often the real message isn't the loud one. It's the quiet, invisible pressure that shapes who we start to become without even realizing it. These subconscious rules that tell us how to behave, what's worth chasing, and who we should become. That's what EveryCity is about.

I won't be telling you where to eat or where to stay. There's plenty of resources for that. Instead, I envision EveryCity as a lens for navigating ambition, identity, and culture, where we can borrow lessons from everywhere and remix them into our own lives, wherever we happen to be.

Over time, I imagine this podcast to be less and less about me, but since I'm kicking it off, let me give you a short introduction. I'm Steven. Nice to meet you. I've lived and worked in five countries on five continents, and I've traveled to about 80. I grew up in Virginia. I studied in North Carolina and San Diego, California. I've worked in Washington DC and New York City. And for the past decade, I've been overseas working in the United Arab Emirates, the Netherlands, Brazil, and now Japan. In some places, I felt like a local. In other cities, I was definitely the outsider.

I've been living in Tokyo for about 5 years now, and the biggest takeaway for me has been learning to read the air. That's something we'll dig more into in the Tokyo episode, but really, it's about understanding the power of silence. In Sao Paulo, I'd say my biggest takeaway was that skills don't matter nearly as much as resilience. It's nice to be good at something, but what really matters is how long you can stay in the game…how resilient you can be.

Amsterdam taught me a lot about the beauty of public trust, but also that it only works when you respect the shared space.

In Dubai, let's just say if you're not already somebody, you probably should play the game like you are. And in In New York, I learned that I was poorer than I thought, but maybe also richer than I had realized. Wealth has layers, and you better figure out where you fit, because nobody's going to figure it out for you.

By now, I hope you understand the idea behind this project. Not just to explore cities, but to explore the quiet pressures, the invisible ambitions, the unspoken values that shape us without us even realizing. That's the premise, the leading question, but I'm not really sure how it will evolve from there. I tend to be a joking around kind of light and loose person. So, I can imagine we'll do a lot of playful segments…comparing cities to athletes or celebrities, personifying cities, things like that, ranking cities, all that kind of thing. But we'll keep it light, we'll keep it fun, and I hope that you'll be along for the ride.

I also I think it's worth reading “Cities and Ambition” in this pilot. It's quite a long essay, so I've chosen just selected excerpts, but it's still about 10 minutes. So, if you're not interested or you want to read on your own time, feel free to skip ahead about 10 minutes and I'll have a few closing remarks.

A quick bit about Paul Graham as well. Silicon Valley legend. He co-founded Y Combinator, which has incubated some of the most famous companies in the world. one of the most influential people in tech, but I see him as a modern-day philosopher who's really thoughtful in a way that very few people are. paulgram.com, I believe. So, tons of essays on there about a lot of stuff. Highly recommend giving it a read. But for now, here is selected parts of “Cities and Ambition” by Paul Graham.

***

Great cities attract ambitious people. You can sense it when you walk around one. In a hundred subtle ways, the city sends you a message. You could do more. You should try harder. The surprising thing is how different these messages can be. New York tells you above all, you should make more money. There are other messages too, of course. You should be hipper. You should be better looking. But the clearest message is that you should be richer. What I like about Boston, or rather Cambridge, is that the message there is you should be smarter. You really should get around to reading all those books you've been meaning to. When you ask what message a city sends, you sometimes get surprising answers. As much as they respect brains in Silicon Valley, the message the valley sends is you should be more powerful. That's not quite the same message New York sends. Power matters in New York, too, of course, but New York is pretty impressed by a billion dollars, even if you merely inherited it. In Silicon Valley, no one would care except for a few real estate agents. What matters in Silicon Valley is how much effect you have on the world. The reason people there care about Larry and Sergey is not their wealth, but the fact that they control Google, which affects practically everyone.

How much does it matter what message a city sends? Empirically, the answer seems to be a lot.You might think that if you had enough strength of mind to do great things, you'd be able to transcend your environment. Where you live should make at most a couple percent difference. But if you look at the historical evidence, it seems to matter more than that. Most people who did great things were clumped together in a few places where that sort of thing was done at the time.

I wouldn't try to fight this force. I'd rather use it. So, I've thought a lot about where to live. I'd always imagined Berkeley would be the ideal place, that it would basically be Cambridge with good weather. But when I finally tried living there a couple years ago, it turned out not to be. The message Berkeley sends is: you should live better. Life in Berkeley is very civilized. It's probably the place in America where someone from Northern Europe would feel most at home. But it's not humming with ambition. In retrospect, it shouldn't have been surprising that a place so pleasant would attract people interested above all in quality of life. Cambridge with good weather, it turns out, is not Cambridge. The people you find in Cambridge are not there by accident. You have to make sacrifices to live there. It's expensive and somewhat grubby, and the weather's often bad. So, the kind of people you find in Cambridge are the kind of people who want to live where the smartest people are, even if that means living in an expensive, grubby place with bad weather. Cambridge, as a result, feels like a town whose main industry is ideas, while New York's finance and Silicon Valleys is startups.

When you talk about cities in the sense that we are, what you're really talking about is collections of people. A city speaks to you mostly by accident and things you see through windows, in conversations you overhear. It's not something you have to seek out, but something you can't turn off. No matter how determined you are, it's hard not to be influenced by the people around you. It's not so much that you do whatever a city expects of you, but that you get discouraged when no one around you cares about the same things you do. There's an imbalance between encouragement and discouragement, like that between gaining and losing money. Most people overvalue negative amounts of money. They'll work much harder to avoid losing a dollar than to gain one. Similarly, although there are plenty of people strong enough to resist doing something just because that's what one is supposed to do where they happen to be, there are few strong enough to keep working on something no one around them cares about.

Because ambitions are to some extent incompatible and admiration is a zero-sum game, each city tends to focus on one type of ambition. The reason Cambridge is the intellectual capital is not just that there's a concentration of smart people there, but that there's nothing else people there care about more. Professors in New York and the Bay Area are second-class citizens until they start hedge funds or startups, respectively.

Not all cities send a message. Only those that are centers for some type of ambition do. And it can be hard to tell exactly what message a city sends without living there. I understand the messages of New York, Cambridge, and Silicon Valley because I've lived for several years in each of them. DC and LA seem to send messages, too, but I haven't spent long enough in either to say for sure what they are. The big thing in LA seems to be fame. There's an A-list of people who are most in demand right now, and what's most admired is to be on it or friends with those who are. Beneath that, the message is much like New York's, though perhaps with more emphasis on physical attractiveness. In DC, the message seems to be that the most important thing is who you know. You want to be an insider. In practice, this seems to work. much as in LA. There's an A-list and you want to be on it or close to those who are. The only difference is how the A-list is selected. And even that is not that different. At the moment, San Francisco's message seems to be the same as Berkeley’s. You should live better, but this will change if enough startups choose SF over the valley. I haven't found anything like Cambridge for intellectual ambition. Oxford and Cambridge, England feel like Ithaca or Hanover. The message is there, but not as strong.

Paris was once a great intellectual center. If you went there in 1300, it might have sent the message Cambridge does now. But I tried living there for a bit last year, and the ambitions of the inhabitants are not intellectual ones. The message Paris sends now is do things with style. I liked that actually. Paris is the only city I've lived in where people genuinely cared about art. In America, only a few rich people buy original art, and even the more sophisticated ones rarely get past judging it by the brand name of the artist. But looking through windows at dusk in Paris, you can see that people there actually care what paintings look like. Visually, Paris has the best eavesdropping I know.

Does anyone who wants to do great work have to live in a great city? No. All great cities inspire some sort of ambition, but they aren't the only places that do. For some kinds of work, all you need is a handful of talented colleagues. What cities provide is an audience and a funnel for peers.

You don't have to live in a great city your whole life to benefit from it. The critical years seem to be the early and middle ones of your career. Clearly, you don't have to grow up in a great city, nor does it seem to matter if you go to college in one. To most college students, a world of a few thousand people seems big enough. Plus, in college, you don't yet have to face the hardest kind of work, discovering new problems to solve. It's when you move on to the next and much harder step that it helps most to be in a place where you can find peers and encouragement. You seem to be able to leave if you want once you found both. The impressionists show the typical pattern. They were born all over France and died all over France. But what defined them were the years they spent together in Paris.

Unless you're sure what you want to do and where the leading center for it is, your best bet is to try living in several places when you're young. You can never tell what message a city sends till you live there, or even whether it still sends one. Often, your information will be wrong. I tried living in Florence when I was 25, thinking it would be an art center. But it turned out I was 450 years too late. Even when a city is still a live center of ambition, you won't know for sure whether its message will resonate with you till you hear it.

When I moved to New York, I was very excited at first. It's an exciting place. So, it took me quite a while to realize I just wasn't like the people there. I kept searching for the Cambridge of New York. It turned out it was way, way uptown, an hour uptown by air. [For those who don't know, he's actually referring to Boston where the Cambridge he's talking about is located. Uh, he's saying he never found it in New York. Back to the essay, and almost done.] Some people know at 16 what sort of work they're going to do. But in most ambitious kids, ambition seems to precede anything specific to be ambitious about. They know they want to do something great. They just haven't decided yet whether they're going to be a rock star or a brain surgeon. There's nothing wrong with that. But it means if you have this most common type of ambition, you'll probably have to figure out where to live by trial and error. You'll probably have to find the city where you feel at home to know what sort of ambition you have. ‘

***

So, that was "Cities and Ambition" by Paul Graham, or at least the parts that hit me the hardest. And what really stuck with me was the idea that most of us don't even realize we're being shaped by the places we live. It's not always in obvious ways, but in how we define success, how we spend our time, and what we envy in others. But here's the thing. Most of us don't get to live in 10 cities to figure out which message feels right. I just got lucky. Or maybe curious, maybe restless.

I've lived in five countries across five continents, from Sao Paulo to Tokyo, Amsterdam to Dubai, and a few corners of the US in between. And the message each place whispered to me was different. So, my hope is that this podcast can be a proxy for that kind of exploration, a way to eavesdrop on the unspoken ambition of cities you haven't yet lived in and maybe won't ever live in. I happen to live in Tokyo. But you don't have to live in Tokyo to think like Tokyo. You don't need to be in New York to ask yourself the tough questions New York would ask you. You can learn from what each city rewards, what it punishes, what it admires, and what it shames. And you can decide what parts of that do I want to bring into my life, wherever I am.

That's what Every City Whispers is all about. On a personal note, I've been sitting on this idea and a lot of others, for way too long. I kept waiting until I had more credentials, more polish, more permission until my voice sounded official enough. But what I've realized and what this show is really about is that you don't need someone else to tell you that your voice matters. You move first, you figure it out later. So, this is me moving. I studied journalism and cultural anthropology, but I ended up in digital marketing. Not because it was the dream, but because it gave me opportunities to live around the world.

I've seen a lot. I felt a lot, but I've rarely taken the time to share it. Partly out of self-doubt, partly out of perfectionism, self-consciousness, and partly because I thought I needed some sort of credential, some external stamp of permission to say, "This is what I've learned. You should listen."

But you know what the truth is? That I've lived through something a lot of people are curious about. And that curiosity. both yours and mine, is reason enough to hit record. Not because I'm an expert, but because sometimes just paying attention…just being curious… is enough to start.

This podcast is an experiment. The format might shift, the tone might evolve, the stories might get more layered and strange, human, and that's the fun of it. For now, I'll start with the cities I've lived in. Tokyo, Sao Paulo, Amsterdam, Dubai, New York. Eventually, I want to bring on guests, street level thinkers, artists, entrepreneurs, regular people who really know their city. But until then, I'll take the bumps on my own chin and figure it out one episode at a time, just like my neighborhood sushi man, still a beginner. Stick around with me because I can't wait to explore with you.

We don't just live in cities. Cities live in us. We can only be in one place at a time, but we can borrow lessons from all of them if we're willing to pause, pay attention, and listen.

This is Every City Whispers.

I'm Steven. Thanks for being here. Next stop, Tokyo.