This was not how I had planned to spend my last forty-eight hours in Italy.

I had spent the previous week disappearing into the mountains of Garfagnana, hiking, mountain biking, smoking Tuscan cigars and eating slightly more than all that exercise could plausibly excuse.

I was only back in my hometown, Fano, for two days before flying home to Portugal.

Then, somewhere on the bus back to Fano, I discovered that I would arrive on the exact day of the twenty-second edition of La Fano dei Cesari, the biggest event in town after Carnival and BrodettoFest, a four-day celebration during which thousands of people gather to argue about the correct way to boil the entire Adriatic food chain in tomato sauce.

BrodettoFest celebrates our ability to turn fish leftovers into civic identity.

La Fano dei Cesari celebrates our equally flexible relationship with history: for one day, the entire town becomes ancient Rome, based mostly on costumes, alcohol and whatever people remember from Gladiator.

Each neighbourhood gets its own colour. People put on tunics and armour, build chariots, fill them with salami, cheese, fruit and, obviously, barrels of wine.

A lot of wine.

They then march through the historic centre until they reach the Pincio, where the fortress rises above the city. When I was younger, the area was mostly known as a convenient place to buy weed. Then it was cleaned up, filled with lights, and turned into something people could proudly bring their children to.

Progress.

Anyway, standing on top of that fortress, surrounded by several hundred Romans and overlooking an arena where horses would soon drag chariots around in circles, I had two revelations.

The first came while looking at the fence separating me from a very stupid death.

The second came while looking, possibly for slightly too long, at the beautiful Roman women around me.

The two revelations seemed unrelated.

One involved public infrastructure. The other involved lust.

It took me a while to understand that they were pointing at the same thing.

The fence came first.

Someone had spent years earning a degree, passing a state exam and becoming licensed to work on public projects. Then came the tender, the specifications, the meetings, the regulations and the liability. Finally, after all that, the fence.

Days spent inside AutoCAD. Measuring angles. Comparing materials. Calculating loads. Moving lines around a screen so that drunk Romans like me could lean over the edge of a fortress without becoming a municipal incident.

Then someone else had come to the fortress and built it.

The same fence. Two completely different relationships with reality.

The designer had worked through representations: drawings, measurements, regulations, numbers. The builder had touched the stone, carried the materials, fought against gravity, felt the sun, probably sworn several times and gone home with dust on his clothes.

This was unfair to the designer, whose work was real, necessary and probably much harder than I understood. Without those lines, there would have been no fence.

But one person had imagined the object.

The other had made the lines heavy.

Some jobs place you directly inside the physical world. Others happen one layer removed from it.

At least, that was how it felt to me. And I had spent most of the previous few years living in that extra layer.

Then I looked at the girls around me.

They were beautiful. Not in the polished, carefully selected way people look on dating apps. They were dressed as Romans, drinking wine, laughing with people they had probably known since primary school.

Fano is small enough that everybody knows everybody, or at least knows who everybody has slept with.

I had lived there for eighteen years before leaving for Milan, yet I seemed to know almost no one.

I had come to the festival with two friends.

The first was Lorenzo, probably my best friend, who looked like Roman Jesus. His long, curly hair blew in the wind as he wandered around in a tunic with the calm authority of someone who had already forgiven the Empire.

The second was Umberto, a close friend of Lorenzo’s who, until recently, had been more of an acquaintance to me. We had started seeing each other more often after discovering, outside a pub after a few drinks, that we both practised Brazilian jiu-jitsu.

The obvious adult response was to strip down to our boxers in Rocca Malatestiana at one in the morning and try to choke each other unconscious.

At the festival, Umberto was wearing no shirt and a very short red Roman skirt. This created a political problem because our neighbourhood was blue.

Out of the blue (see the pun?), my mother found a piece of rope, tied his wrists and declared him the captured slave of our division. This somehow made the red acceptable

Umberto is tall, well-groomed and offensively jacked. At least eight abdominal muscles were visible, which is surprising considering the amount of wine and nicotine pouches I have watched this man consume.

I would be lying if I said I wasn’t jealous of the attention he was getting. I tried to treat the jealousy as field research.

I could watch the women’s eyes follow him as he walked past. First the abs, then the face, then the verdict, all performed with enough nonchalance to preserve plausible deniability.

Umberto would notice, trace the gaze back to its source and simply walk over. He did not need an opening line. He would ask whatever stupid question entered his head.

So when does the march begin?

How do the chariots work?

How much do I have to pay for a slice of salami?

The questions did not matter. He was already there.

At one point, a goth-looking girl with perfect makeup watched him approach, narrowed her eyes and slowly bit one of her nails. It was so sexually explicit in its restraint that I had seen porn films begin with less.

It was humbling.

A few days earlier, I had asked ChatGPT how many Italians my age had as much money as I had in the bank.

It told me, with the statistical confidence of a machine that would never be held accountable, that the number was probably somewhere between 0.05 and 0.1 percent.

Not a single person on that fortress seemed particularly impressed.

Which was reasonable.

Money is useful even when nobody can see it. It buys freedom, time and the possibility of leaving situations you no longer want to be in.

But money becomes visible only through what it changes in your life.

Mine had mostly turned into travel, companies, bank accounts, tax residencies and a suspiciously detailed understanding of email deliverability.

It had given me options. It had not given me a body I felt completely at home in, a place inside the city’s social fabric or the confidence to walk across a square and speak to someone I found attractive.

The attention Umberto was getting had nothing to do with money.

He was simply there.

In his body. In the city. Among people who could see him.

I had spent the years when adult friendships and social circles were taking shape jumping from place to place, building businesses but few roots. I had never learned how to dress particularly well. My Italian had become littered with English words. I had let my hair and beard grow slightly feral, and I had returned from Garfagnana carrying several additional kilos of Tuscan cuisine.

Whatever I had accumulated existed mostly in accounts and dashboards.

That was the second revelation, or perhaps the same revelation seen from the other side.

I knew how to build an n8n automation, but I did not know how to dance.

I knew how to open companies, bank accounts and residencies in different countries, but I could barely cook myself a proper dinner.

I knew how to get around Google’s filters and deliver emails into thousands of inboxes, but walking across a square and introducing myself to a woman still seemed more complicated.

Sure, I had been on plenty of successful dates through dating apps.

But the apps were part of the same problem.

They allowed me to search, filter, match and message. They had turned intimacy into another funnel that a marketer like me could optimise.

Perhaps that was why I had been so comfortable using them.

They were outside life.

For years, I had become increasingly competent at things that protected me from the embarrassment of being physically present.

I had learned how to make money, move countries, generate leads and automate work.

All useful skills. None of them could cook for me, dance for me, build friendships for me or walk across that square and win over the beautiful goth girl on my behalf.

Some tastes, unfortunately, survive every attempt at optimisation.

Since that night, which was literally last week, I have been trying to force myself further inside life.

Not further inside my head. I have lived there long enough.

Inside life.

Get your hands dirty. Walk up to people before you have time to optimise the interaction. Learn things with no obvious return except a tired body, a new memory, a bruise or a story.

Ride a motorcycle somewhere. Sneak into a conference. Learn how to dress and build a wardrobe that actually feels like yours. Put your face and personality on camera and survive being seen.

Learn to fly a plane. Go scuba diving. Learn another language.

Learn Portuguese, for fuck’s sake. I have lived in Portugal for two years and still cannot speak it properly.

Learn all the apparently useless things with zero measurable ROI that remind you that you have a body, a soul and only one chance to use both of them.

I want the same from my work.

I no longer want a job that requires me to step outside life in order to earn a living.

I want work that grows out of living: going places, meeting people, attempting things badly, paying attention and coming back with something worth telling.

I want to make a living out of feeling alive.

Not watching life through a dashboard.

Not filtering it through an app.

Not moving representations of it around a screen.

Actually being there.

And you, reading this: do you feel like you’re living inside or outside your life?

The good news is that we can always step back in.

This is episode #1 of The Scenic Route, the long way around my life.

If you are joining somewhere in the middle, the full route is collected here.

If you want to understand why I started writing all this in the first place, read Cropped Out.

Before the agency became an agency, there was a phone call.

Let me explain.

I was forced to resign from Glaut on March 22, 2024, two days before my birthday.

Which was thoughtful of my former teammates, in the sense that they gave my existential collapse a clean calendar date I would never forget.

A few weeks later, I was still in Milan, screaming into a pillow and calling friends because I had no idea what to do next.

Some people get a mentor.

Some people get therapy.

I got Dylan.

Which requires a small detour, because Dylan was not exactly a random friend.

I had met Dylan years earlier through Aurora, a fellowship built for the kind of young people whose ambition, ego, and unresolved childhood material make them apply to something called a fellowship in the first place.

Inside Aurora, there was a €10,000 prize if you completed three challenges.

The first one was to write your own biography and get people to comment on it, which, considering what you are reading right now, may have been my villain origin story.

The second one was stranger.

They gave you a list of ten random people, and your job was to reach out, book calls with them, and somehow convince them to fill out a form certifying that you were a young talent.

Which is an insane thing to ask a teenager to do.

But also, apparently, an excellent way to manufacture a future cold email consultant.

I remember writing to PhDs, billionaires, IP lawyers, Nobel Prize physicists, mechanic shop owners, retired investors, and a suspicious number of people whose LinkedIn profiles looked like a government experiment, somewhere in the extended MK Ultra cinematic universe.

Obviously, as a teenager, I had absolutely nothing to offer most of these people except curiosity, audacity, and a subject line good enough to make them question their afternoon plans.

So my strategy was basically deep research, one weirdly specific question, and, when necessary, begging.

Which, in retrospect, might explain why a few years later I became disturbingly good at cold email.

My last certification came from one of the strangest people I’ve ever met.

Imagine an Italian Nikola Tesla, if Tesla had lived long enough to apply for EU grants and build giant wind farms in the sky.

He had apparently raised tens of millions of euros to build the next generation of energy infrastructure using kites flying 13,000 meters in the air to harvest tropospheric wind.

He claimed it could generate energy more efficiently than nuclear power, without the same toxic byproducts.

He also did not believe in global warming, lived in complete paranoia, and personally told me that Bill Gates had hired spies to follow his every move and sabotage his company.

Very normal networking experience.

After all that effort, I expected the third challenge to be some impossible intellectual trial.

Instead, it was a Google Meet interview.

Extremely anticlimactic.

Anyway, both Dylan and I passed everything, only to discover that the €10,000 prize had been removed a few weeks before we finished.

United by disappointment, mild betrayal, and the very specific humiliation of having competed for money that no longer existed, we became friends.

Over the years, our digital footprints kept crossing paths online, which is a very modern way of saying we stayed in touch.

We even met again a year later, both stuck inside a startup accelerator in Milan.

One of those accelerators so bad you don’t even put it on your LinkedIn profile.

At the time, Giovanni and I were building something called Livesey, which would later become the first of six pivots before Glaut finally became Glaut: an attempt to make GPT read a company’s internal documents through a vector database we had built from scratch.

Dylan was orbiting the chaos from the marketing side, helping us make each new version of the idea look slightly less doomed than the previous one.

In 2023, this was the bleeding edge.

Now it’s called RAG, and you can basically drag and drop a PDF into ChatGPT while eating a sandwich.

Time is cruel.

Still, the best memory I have from that period is not the company we were building, or the technology, or whatever delusional pitch deck we were using to convince ourselves this thing mattered.

It is Dylan coming over for the weekend and teaching Giovanni and me how to make tiramisù.

Because Dylan, being a distinguished gentleman from Treviso, apparently considered it his civic duty to educate two spiritually malnourished startup founders on mascarpone, coffee, and the structural integrity of ladyfingers.

There are people you remember for their strategic insight.

There are people you remember for their emotional presence.

And then there are people you remember because, at some point in your life, they stood in your kitchen and explained tiramisù with the seriousness of a constitutional lawyer.

Dylan belonged somewhere between all three.

He had round glasses, green-blue eyes, and the kind of buzz cut that only works on people who have never had to negotiate with their hairline.

He usually dressed like someone who might leave a business meeting and immediately go climb a mountain: technical clothes, gym clothes, outdoor gear, and those horrifying Keen hiking sandals he loved with the sincere devotion only practical people can feel for ugly objects.

Nevertheless, he was a freelance marketer.

An alchemist of sorts, capable of turning clicks into gold through all the little tricks that make people buy things they later pretend were rational decisions.

He once showed me the Figma archive he used for inspiration, and I remember being genuinely blown away by it.

He had documented hundreds of landing pages, funnel structures, signup flows, email sequences, and page progressions from the biggest tech companies in the world, placing them side by side with terrifying precision, as if he were trying to reverse-engineer capitalism one screenshot at a time.

It looked less like a normal marketing swipe file and more like one of those conspiracy boards from crime movies, with pins, red string, and the quiet implication that someone had either discovered the truth or completely lost their mind.

Except in Dylan’s case, the conspiracy was just:

“Why do people click?”

Which sounds insane until you realize that, unfortunately, it worked.

He was annoyingly good at it.

By then, he had already orbited enough of my projects from the marketing side that he no longer felt like a random internet friend.

So when I was falling apart in Milan, he was one of the people I called.

I don’t remember exactly how the call started, but I remember telling him the story.

The collapse.

The company.

The friendship.

The money that had existed mostly on paper.

The life I thought I was building and had somehow been cropped out of.

He listened for a while and then said something like:

“Phil, I know what you actually need. We’re organizing a trip to Bali. Come with us for a month.”

Which, in retrospect, is exactly the kind of sentence that either saves your life or ruins it more creatively.

And because I had no better plan, no emotional stability, and apparently very little resistance to plot development, I said yes.

But Bali was in May.

Which meant I still had a month in Milan to survive before the escape route became real.

And Milan, at that point, had become impossible to survive.

Not because Milan is an especially tragic city.

It is mostly just expensive, grey, ambitious, and full of people confusing cortisol with purpose.

The problem was that I had lived too much of myself there.

Every neighborhood had become a small museum of something I had failed to finish, lost, abandoned, or outgrown.

Lambrate reminded me of the physics degree I never completed.

Yes, reader, my mother is still unhappy about that.

Vigentino reminded me of the worst networking event of my life.

The drinks were terrible, the average person was forty, and the most innovative startup in the room seemed to be importing Japanese snacks into Italy with the geopolitical seriousness of the Marshall Plan.

Then there was this young guy.

Tall and broad like a wardrobe, baby-faced, with nerdy glasses, an intense stare, and long hair that made him look like a hobbyist hacker from the sixties who had discovered LSD the week before.

When he spoke, his voice came out deep and almost intermittent, as if every sentence had to buffer before becoming real.

That was Giovanni.

Navigli and De Angeli reminded me of living with him.

Bande Nere reminded me of the time Giovanni and I decided to spar Muay Thai in the middle of a public roundabout, for reasons still unknown to both urban planning and common sense.

Duomo reminded me of our first office.

Technically, it was in Piazza San Sepolcro, where the manifesto of Italian Fascism was signed.

I am not implying anything about our startup culture.

I am simply reporting a funny coincidence to the authorities.

Romolo reminded me of our second office.

And of the weight I gained by eating at the nearby Old Wild West far too often.

Porta Romana and its hostels reminded me of my youth passing by.

Of being young, broke, overworked, and typing on my laptop late at night while people my age were outside being drunk, beautiful, stupid, dancing, flirting, smoking, becoming stories.

And there I was, replying to emails.

Giambellino reminded me that I did not have enough money to live somewhere better.

Which is a very humbling realization when, not long before, you had been calling yourself a paper millionaire.

My apartment was five and a half square meters.

The bed alone took up half the room.

Mold on the ceiling.

At home, I used to work sitting on my bed, laptop on a tiny desk squeezed against the wardrobe.

There were eight roommates, each more annoying and chaotic than the last.

And next to my desk, there was a sink.

For a while, nobody explained it.

Then one day, a young art teacher who lived two rooms down told me the truth.

My room used to be a bathroom.

Man, people in Milan will do anything to squeeze more money out of an apartment.

They will look at a bathroom and see a business opportunity.

So I spent most of my days, and sometimes even my nights, in the office.

No shit.

The office was not comfortable either.

I slept on the floor, on two cushions that were not long enough to hold a human body.

One under my head.

One under my legs.

Nothing in the middle.

So every night my spine folded into a sad little V.

Still, it was better than going home.

At least until the cleaning lady came in at six in the morning, found me on the floor, and started screaming.

One time I had a date.

A successful one, somehow.

I invited her home.

She saw the room and left almost immediately.

The only thing she left behind was a blue bottle of Bombay gin.

I brought it to the office fridge.

For a while, before going back home, I used to take one sip of it in the office before returning to my architectural punishment.

My co-founders were not impressed.

“So what now?” they asked. “Gin, wank, and sleep?”

Porta Venezia made me question my heterosexuality with a consistency that felt almost administrative.

Via Lecco, which roughly translates from Italian as Licking Road, could not have been named anything else.

It was basically the closest thing Milan had to a gay Vatican.

My Swiss cousin liked hanging out there from time to time. She told me I could probably get free drinks and, for once in my life, experience what it felt like to be the one getting chased.

I don’t like guys.

But I do respect a favorable market dynamic.

And then there were CityLife and Isola.

The glass towers.

The aperitivos.

The startup people.

The founders who seemed to have kept what I had lost.

The offices, the investors, the equity, the confidence.

The LinkedIn posts written in that strange dialect where everyone is humbled, excited, and proud to announce the same sentence.

They had the story.

I had the footnote.

So no, Milan was not just a city anymore.

It was a map of open tabs in my nervous system.

Everywhere I went, the city handed me back an older version of myself.

And I had no idea how to become someone else while the whole place kept pointing at who I had been.

So I spent April doing the only sensible thing a recently exiled founder could do while waiting for Bali to become real.

Panic-selling his skills to anyone who might pay him.

I made an Excel sheet with completely made-up assumptions and called it a business case.

I was pitching it more or less like this:

Look.

If I send one email to every potential buyer in your market, and say, only 1% of them convert, and your average deal size is high enough, then you make an incredible ROI on my work.

If I can get you that kind of ROI, would you try it out?

P.S. I am a founder too. I raised money too. I did this at Glaut and got meetings with billion-dollar companies.

At the time, this was apparently the closest thing I had to a personality.

It was not exactly McKinsey.

But it had numbers, confidence, and just enough truth in it to be dangerous.

I even had a slide deck, because nothing says “I am processing this in a healthy way” like turning your nervous breakdown into a sales presentation.

By the time I left, I had managed to get two clients.

I was technically a freelancer, although “unemployed with clients” would have been more accurate.

And of course, while I was trying to rebuild my life, the cold email world was quietly rebuilding itself too.

Google had changed things.

The old tricks stopped working.

The little hacks I had used at Glaut started breaking one by one.

Before, you could blast an irresponsible number of emails from a single inbox through SMTP servers like SendGrid and call it marketing.

Now suddenly you needed multiple domains, multiple inboxes, warmup, rotation, backup infrastructure, inbox placement tests, and all the other words that make normal people regret asking what you do for work.

That was the beginning of the multi-domain, multi-inbox era, later popularized by tools like Instantly.

Some people remember their twenties through love stories.

I remember mine through email deliverability updates.

But eventually, even cold email historians have to pack a suitcase.

By the time I finally boarded the plane, I had two clients, €10,000 in savings, zero structure, a dying playbook, and a ticket to Indonesia.

Which, somehow, was still the best plan I had.

I was not moving toward Bali as much as I was moving away from Milan.

At the time, I thought that was the same thing.

It wasn’t.

The Scenic Route is a serialized biography told one place at a time.

Not in the clean order people usually use when they try to explain themselves.

More like memory works: cities, detours, bad decisions, unfinished versions of myself, and places that changed the plot by accident.

If you want to understand why I started writing all this in the first place, start with Cropped Out, then follow the route.

More soon, unless I finally become a stable person.

Unlikely.

Start here

The route

#2 — Bali

Coming soon

#3 — Lisboa

Coming soon

#4 — Bologna

Coming soon

#5 — Sofia

Coming soon

#6 — Paphos

Coming soon

#7 — Phuket

Coming soon

#8 — Chiang Mai

Coming soon

#9 — Bali, again

Coming soon

#10 — Lourdes

Coming soon

#11 — Marrakesh

Coming soon

#12 — Coimbra

Coming soon

#13 — Panamá

Coming soon

#14 — Bangkok

Coming soon

#15 — Koh Samui

Coming soon

#16 — Da Nang

Coming soon

#17 — Panamá, again

Coming soon

#18 — Coimbra, again

Coming soon

Act I
──✦──
In medias res

At 24 I was running my own business: a team of five making roughly $400,000 a year.

Most founders spend years trying to reach that point. I spent months trying to convince myself not to walk away from it.

To understand the decision, you first need to understand my questionable psychology.

It probably starts in childhood. Freud would have a field day with it.

Because my life has been... weird.

And when I say weird, I don’t mean the kind of weird you’d find between aisles 5 and 6 of a discount department store.

I mean the kind of life where, by my early twenties, I’d already been an award-winning jazz musician, a portrait photographer, a bartender on a pirate ship in Malta, an Olympiad physics student, a startup founder, and a university dropout who somehow convinced investors to hand him $1.4 million.

At some point IBM and Harvard gave me a scholarship to study quantum computing, and on random Tuesdays I’d study bioinformatics and genome sequencing algorithms for fun, because apparently my brain doesn’t know how to relax.

I won’t get into all of it here, mostly because I still haven’t figured out how to tell that story coherently, concisely, or without accidentally wandering off into a completely different one.

I actually tried to write part of it down back in 2022. Unfortunately for you, reader, the last four years only made the plot weirder.

The short version is this: in my endless search for creative freedom, I stumbled into entrepreneurship in high school, built my first startup, and from there ambition took over.

I may have read one too many biographies of the billion-dollar founders we all know and love. Or hate, depending on how allergic you are to capitalism. Either way, at some point I basically became a living Silicon Valley caricature.

I wanted to become one of them. The Italian Elon Musk, or at least that’s what I told myself at the time.

But here’s the thing.

It was never really about the money.

I probably peaked at twenty-one, the year I raised $1.4M for Glaut.

It felt like life had cracked open in front of me.

Suddenly, all those impossible founder stories no longer felt impossible. Forbes, Y Combinator, Sequoia. Whatever came next, I could already picture myself there.

Hell, they even brought me back to teach a class at the same university I’d dropped out of months earlier.

And from there, things escalated quickly.

I got invited into rooms I genuinely had no business being in.

Private dinners in skyscrapers with founders whose companies were worth billions.

At one point I spent ten minutes talking with Patrick Collison from Stripe.

I was trying very hard to keep my cool and pretend this was all somehow normal.

And because I was apparently incapable of having a normal human interaction with a billionaire, I asked him what he thought the next big thing in finance would be.

He went quiet for what felt like three minutes, then said: customer support.

This was October 2022, so at the time the answer sounded almost disappointingly boring. Especially since he’d just spent a third of my ten minutes staring into the distance.

Then ChatGPT came out a couple months later and I realized the guy probably knew something the rest of us didn’t.

That was the strange thing about those circles.

Everyone seemed to exist slightly ahead of reality.

Financially, I was so far behind that even the janitor was probably a millionaire.

I saw private jets parked like taxis, artwork hidden in vaults for tax deductions, and food so absurdly good it tasted more real than life itself.

Pride consumed me completely.

I genuinely thought I had made it.

And I didn’t want it to stop for a single second.

Then came my own Paradise Lost, except the apple was equity and everyone had a lawyer.

From the outside, Glaut was doing well.

That was almost the cruelest part.

It would have been easier if everything had clearly fallen apart. If the product had stopped working, if the market had rejected us, if the story had collapsed in some clean, obvious way.

But it didn’t.

The company was thriving.

It was the founding team that started to fracture.

We disagreed on product, on hiring, on legal. And slowly every conversation stopped being about the company and started being about the kind of people we thought we were.

Eventually, it became clear there was no place left for me in the company I had helped bring to life.

And then, almost comically, the erasure became literal.

Right before everything exploded, I had shot the team photos for the press release myself.

Photographer brain never dies, apparently.

By the time the article went live, I was already being pushed out, so they cropped me out of the official photo too.

And just like that, where I used to be, there was nothing.

The crop was so bad that it became LinkedIn comedy material for the Italian startup ecosystem for a while.

A bootleg startup version of The Picture of Dorian Gray, except the portrait didn’t reveal the corruption of my soul.

It revealed their disappointing Canva skills.

And the humiliating fact that my entire identity could be removed with one bad crop.

I had spent every waking second on that company. Thinking about it, building it, defending it, obsessing over it.

There was almost nothing of me outside that frame.

Without it, the future just felt blank.

Maybe I would go back to university.

Maybe get a normal job.

Maybe move back in with my parents.

Money was running low too. For a while, I had technically been a paper millionaire. Then I learned how cruel the word technically can be.

Most of it vanished before it ever became real.

Paper millionaire, cash poor.

But losing the company wasn’t even the part that hurt the most.

It was losing my best friend.

Giovanni.

For two years, Giovanni and I lived inside the same little universe.

Same apartment. Same office. Same gym. Same impossible dream.

Same arguments at 2am about product, money, strategy, life, meaning, and whatever else two half-insane young founders convince themselves matters while trying to bend reality before rent is due.

We spent so much time together people genuinely thought we were secretly dating.

And in some weird founder way, maybe we were.

Not romantically, obviously, but existentially. Our futures had become so intertwined that normal friendship stopped feeling like the right word for it.

At first, that kind of closeness feels like magic.

Then slowly, almost invisibly, it starts turning into something else.

You hear every story twice. Then ten times. Then a hundred. Every joke has already been made. Every opinion has already been litigated. Personal life disappears. Mystery dies. Familiarity stops feeling warm and starts feeling like a sink full of dirty plates nobody wants to wash.

Still, I thought the bond underneath all of that was real.

We had seen each other at our most delusional, exhausted, pathetic, and alive.

We had built something from nothing.

For a while, against all odds, the world seemed to believe us.

And then, when everything collapsed, he chose the other side.

Not mine.

Maybe that’s the childish version of the story.

But that was the first time I understood what happens when a dream turns into paperwork.

All the years, the nights, the debt, the hunger, the shared insanity. None of it shows up in the contracts.

Those pages only see shares, signatures, risk, and control.

Sometimes the rational move is also the cruel one. Legally correct, strategically smart, and still disgusting.

And in the end, the cap table won.

Even against everything that couldn’t be priced, signed, protected, diluted, or sold.

Including friendship.

A few months earlier I thought I was on my way to becoming the Italian Elon Musk.

Now I was twenty-one, standing in the smoking ruins of my own ambition.

Which left me with a question straight out of the gates of Hades. The kind you don’t want to answer, because you’re afraid of what the answer might be.

What now?

I had three options, and I hated all of them.

I could finish university and finally make my mom proud. I could get a normal nine-to-five at another startup. Or I could try to monetize the only thing I had left: the skills and the network I’d built at Glaut.

The third option was objectively the worst idea. So naturally, I chose it.

Partly because my ego was still far too unemployed to accept having a boss.

Partly because going back to normal life after everything I had lived through felt like waking up from a dream I was not ready to leave.

And partly because, at that point, I didn’t believe something was meaningful unless it was painful.

So I did what I always did when I didn’t know what to do: I turned the pain into work.

The agency wasn’t a dream. It was a scar with a revenue model.

At Glaut, I had been leading growth, and somehow I’d figured out how to consistently book 40 sales calls a month with no ads, no team, and no real budget.

Just thousands of emails going out every day, automated from a tiny apartment full of sleep-deprived optimism and questionable legal compliance.

I thought maybe I could replicate that system for other startups and help them get clients.

I also had a theory: if I could help companies make money, they would probably find budget for me.

The thing became profitable almost immediately.

Which, given the emotional state I was in, felt less like a victory and more like a design flaw in capitalism.

Because I already had the right relationships inside the Italian startup ecosystem, growth came surprisingly fast.

I’d call an investor on Monday and by Wednesday I’d have three sales calls lined up with top-tier startups from their portfolio.

Over time, the agency grew.

I went through a couple of co-founders along the way. But those are stories for another day, and a softer couch.

And eventually, that little post-traumatic survival experiment became the same $400k-a-year agency I opened this whole thing trying to explain.

But let’s step back for a second.

I’m not sure if you’ve realized it by now, but this essay has clearly stopped being only about why I shut down my agency.

Somewhere along the way, it became a biography with a small agency-shaped excuse attached to it.

I hooked you.

And unfortunately, I hooked myself too.

What started as an attempt to answer one clean business question became an excuse to keep writing. To remember stupid things that happened along the way. To excavate feelings I had conveniently buried under work.

And maybe to understand why the hell I keep burning down lives that were starting to look stable, functional, and almost socially acceptable.

Which is annoying, because I did not emotionally consent to writing a biography when I opened the blank page.

But here we are.

The actual answer to why I shut down the agency is at the end of this essay.

It is exactly 62 characters long.

Everything else is the scenic route.

And I have always had a weakness for the scenic route.

You think the point is to arrive somewhere, but then the road starts doing its thing.

The detours.

The breakdowns.

The wrong turns.

The ugly towns that somehow become beautiful because the sun was setting.

The single-serving people you meet once, love for three hours, and never see again.

The gas station sandwiches that were technically vegan, if you don’t count the microplastics.

The random parties where strangers offer you beer and a shot at karaoke in an alphabet you can’t read.

And somewhere along the way, you realize the destination was mostly an excuse to start moving.

Maybe this essay is the same.

I started writing because I thought I owed people an explanation. Why let go of profitable clients and loyal employees? Why stop optimizing a machine that was finally working?

But the more I wrote, the less I cared about the clean answer.

You already know it’s 62 characters long.

The hard part is understanding the kind of person who needed to build that machine in the first place. And the kind who eventually needed to leave it behind.

So here is the deal.

There are two roads out of this essay. Maybe three.

The short one: keep reading. A few more minutes and you get the 62-character answer, clean and done.

The long one is everything that made that answer inevitable. The life underneath it, one country at a time. The Scenic Route, the actual one. And it starts in Milano.

And then there is the third road. The one I’m on right now.

Because even if you read every word I write, I’m not sure two people can ever really know each other.

Maybe we are all a bit like flowers. Rooted in place, reaching for each other and never quite getting there.

So flowers do the only thing they can. They throw things into the air. Pollen, scent, color.

We do the same. Words, jokes, love, essays nobody asked for. Small desperate signals, hoping one of them drifts close enough to another soul.

But the wind decides where they land. Not us.

And maybe the reason you’re still here is that you’re holding one of your own.

A story you keep refusing to write, because some part of you knows that once you start, it will outgrow the question you began with.

If that’s it, you don’t need my essay. You need a blank page and the nerve to fill it.

So go. You can always come back later. Or not. The road rarely cares whether you arrive.

I meant to get back to the main story here and finally answer the question.

But my armodafinil-assisted hands seem to have developed a literary agenda of their own.

They are less interested in giving you a clean answer.

They are more interested in finding a version of my life I can actually live with.

If you came for the clean answer, this is where I stop taking the scenic route.

So I built the agency, and it worked.

For the first time in my life I wasn’t startup rich. I was liquid.

Money in my account every month. No board, no fundraising, no pretending a spreadsheet was the same thing as cash.

And because I kept moving, a new country every month, I got something I’d never had before.

Freedom. The real kind. The kind that lets you notice you might enjoy your life more than your work.

Then the noticing wouldn’t stop.

Travel had quietly taught me a few things I couldn’t unlearn.

That I had been living for the weekends, doing things I hated five days out of seven to afford the two where I felt alive.

That I was wrecking my body, my mind, and every relationship I had, to earn money I didn’t actually need.

That on a beach in Thailand or a $1,000 month in Vietnam, I felt richer than I ever had with a cap table.

That I would probably never love business itself, only the freedom it bought, and the two are not the same thing.

That nobody was watching my life as closely as I feared, which is terrifying for a day and then the most freeing thing in the world.

And that staying loyal to a promise my younger self made was just a polite way of betraying who I’d become.

None of my best memories had anything to do with work. They were all from the time off.

So I figured: why keep living for the weekends? Why not build a life where feeling alive is the job, not the reward for surviving it?

Why spend years mastering every secret of cold email deliverability, when I could just sit silently and watch a sunset?

The agency itself had never been the dream.

It was a profitable response to a trauma. Something I thought I’d do for a few years before moving on to something more interesting.

There was no vision except me with more money than before.

It didn’t fail. I wasn’t broke. There was no disaster.

It was working correctly the day I shut it down.

It had just become a life I no longer wanted to repeat.

And that turned out to be reason enough.

So, finally. Why did I close the agency?

Because it was boring, and your only chance at life shouldn’t.

That’s the answer. 62 characters.

If you want the rest — every country, every crisis, every version of me that had to happen first — that’s The Scenic Route. And it starts with Milano.