Pick any of my posts on entrepreneurship—or ask what I’ve been up to this year—and you’ll see I’m as enthusiastic about designing and building new ventures as I was eighteen years ago when I launched my first business. Ever since regaining some breathing space from my last enterprise in 2023, I’ve been asking myself a simple but unsettling question: Where do great enterprises really come from?

They say time can never beat timing. You can clear out your agenda and spend all the time in the world chasing your goal—and when you fall short, you can try to find even more. Yet things tend to happen when the time is right, whether you’ve worked for a lifetime or just long enough, whatever that means. Preparation matters, but developing a sensitivity for timing is just as important.

For someone who often feels stifled in Milan—by its provincialism, and by how far it still lags behind the world’s great urban centers—L’Aquila is an unlikely place to admire.

What does the British empire, the Pentagon, and Jensen Huang have in common? Bear with me through three short anecdotes. I bet it will give you a satisfying conclusion. Captains, sailors, and sovereign nations have been grappling with the challenge of measuring position over a parallel (longitude) for centuries—millennia, in fact…

For all the content out there on job seeking, career change, entrepreneurship, or the business of being a creative, there’s a remarkable emptiness on one crucial topic: how do you choose between two or more paths you’re already pursuing? Most books and training materials focus on the drawing-board stage. They typically lead you to take stock of three things, or a combination of: your assets, what you’re chasing, and what you want to escape from. At best, they offer frameworks to compare options before you’ve invested deeply in any one of them…

Last year my friend K introduced me to a simple but powerful metaphor: protein-rich content and carb-rich content. We were talking about podcasts, but the idea applies to every kind of media. Protein-rich content is what you can build on. It isn’t the easiest or most entertaining to consume—it demands attention, and without it, it can feel like background static. But when you engage, it delivers education and long-term knowledge. The definition of signal.

On a single morning dog walk, I heard two different hosts repeat the same line within forty minutes: “I Don’t Have to Work Another Day in My Life.” It’s a catchy line. No wonder it’s become the go-to phrase for so many successful creatives, writers, advisors, freelancers—and even the lady running the laundry shop in my neighborhood (one shirt, washed and pressed, for eight euros… really?)…

A slow, balmy Sunday. Creams, golds, rusts, mighty teals. Aged. Forsaken. Unseen by the eye. True to the soul. Long, steady tones in D minor…

I had never heard of Seth Godin until June 15th. He’s the author of 21 worldwide bestsellers, translated into 36 languages (I can’t even name 36 languages), writes a blog with over a million readers, hosts a top-ranked podcast with 200+ episodes, and—lest anyone think he only talks—has built and sold multiple multi-million-dollar companies. The joke was on me.

My first journal entry is dated November 15, 1979. I was born on December 19, 1979. Yes, my journal starts a month before I was born: a photograph of my mother, nearly nine months pregnant. And… trust me, I’m definitely in that photograph.

A few years back, I added a small atomic habit to my to-do dashboard: on the first of each month, I pick up a book from the library of those I’ve read and chosen to keep (roughly one in three makes the cut), and flip through all the pages I previously marked with one of my trusted Stalogy sticky flags.

This week was in a category of its own. Something happened in my life—my family’s life—that called for a moment of silence. I won’t go into the details, because I don’t feel comfortable doing so. But I’ll say this: I considered pausing my weekly post…

The bad news first. Entrepreneurship is not a finite game. There are no goalposts to tell you how you're doing, or how far you’ve come. Succeeding once—or several times—is no guarantee of a rerun. Failing once—or several times—doesn’t say much about whether this is the right path for you…

Barely a month ago, on June 16th — the one-year anniversary of this blog column — I published a post recounting the origin story of this very website. That piece explored how it all began, and how, through iteration after iteration, I arrived at what I then called Website 3.0 — the third complete overhaul, evolving in step with my own transformations. Well… here is Website 4.0…

Once more to London. Once more to see a show. The last time was March 15th, when I went to see Mr. Wynton Marsalis at The Barbican. This time, it was Michael Jackson. Well — he wasn’t there, of course. But Jamaal Fields-Green showed up in his stead…

Whenever we talk about self-renewal, it's impossible not to talk — explicitly or implicitly — about aging. If self-renewal is about change — not just in our behaviors, but in our identity — and if it’s true that self-renewal is never fast (because it takes time to truly understand what no longer fits in our life, and just as much time, plus trial and error, to reimagine what should take its place), then the question…

Yesterday marked the official launch of Jam Nation — in Milan, and, in spirit, anywhere else. It was the first event of its kind. I’ve written before about my journey with Jam Nation — when I chose it as my next adventure, upon the one year anniversary of its launch, and upon the recent realization that the launch wasn’t about proving anything — it was about celebrating the work.

My first website — version 1.0 — went live on November 29, 2020. It was little more than a digital photo album: a homepage featuring a single image I’d taken early on, soon after buying a camera — the day I realized photography was going to become something meaningful in my life. Alongside it, a quote.

Last Monday, I spent an entire day running an airtight background research operation. My target: a YouTuber who has no idea I exist — and likely never will…

Yesterday, May 31st, after several days of introspection and research, I found myself at my desk — working, creating, thinking, reading, journaling, and watching inspirational videos — when I had a moment of clarity…