American in Santiago 🇨🇱 A decade in Latin America. 12 years building a marketing agency. Somehow became Mexican along the way 🇲🇽
Santiago, Chile 🇨🇱
Joined July 2009
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Meanwhile…
I started sending business payments through an MCP connected to my bank today.
It’s awesome
I still have to physically click to approve the payments though.
SCOOP: Major U.S. banks are detecting unauthorized third-party AI agents inside customer accounts, including some attempting to take actions that appear to be independent of user instructions, sources told Axios.
The findings have alarmed banking executives, who are racing to restrict access to their systems as AI moves at a velocity faster than financial institutions can respond, multiple industry and bank executives told Axios.
Several banks are now preparing for worst-case and even “day after” scenarios, including how to rapidly secure or restore customer accounts if things go wrong, the people said.
Several bank executives told Axios they're struggling to distinguish between human users and AI agents. One executive said banks also struggle to determine whether agents are authorized by customers or potentially operating without their permission, more akin to rogue agent behavior.
Read my latest for Axios here: axios.com/2026/10/22/ai-agen…
Nearly 13 years working with small and mid-sized businesses…
I’ve watched a lot of people take on debt to buy a biz they have zero experience running.
Buying doesn’t skip the education.
Pricing, hiring, retention, cash flow. You still have to learn it all.
SBA loans just put a 10-year personal guarantee on your tuition.
Lat last year I almost bought a plumbing business for 750k. Would’ve have to personally guarantee a 10 yr SBA loan for a business doing 80k a month in revenue where half the net profit went to debt service.
Instead I took the down payment money and opted to start my own from scratch. 6 months in we hit the same monthly revenue as the other business but with no debt.
When analyzing a business to buy the question should always be asked, what would it take to start this and would I be better off in 12 months?
Domestic flights in Chile 🇨🇱 are insanely cheap…
I was pricing a trip to the Atacama Desert and started checking other routes.
JetSMART is advertising one-way fares from Santiago starting at:
• Antofagasta: 8,868 CLP ($10 USD)
• Concepción: 15,900 CLP ($18 USD)
• La Serena: 16,900 CLP ($19 USD)
• Temuco: 16,900 CLP ($19 USD)
• Calama (Atacama): 18,900 CLP ($21 USD)
• Puerto Montt: 31,900 CLP ($35 USD)
Promotional base fares before taxes and extras.
Some of these flights cost less than an Uber ride back in the USA 🇺🇸.
Chile stretches over 2,600 miles from north to south.
You can go from one of the driest deserts on Earth to the lakes, volcanoes, and glaciers of Patagonia without ever leaving the country.
With a little flexibility, exploring this country is surprisingly affordable.
Met a Brazilian 🇧🇷 from São Paulo who told me he'd never live there again…
Great for a wild weekend.
Brutal for daily life.
He lives in Chile 🇨🇱 now and has no plans to leave.
He loves that he can…
Walk around his neighborhood without worrying about being robbed at gunpoint.
Drive a car without bulletproof glass.
Let his kids walk to school on their own.
Count on most days going exactly as he expects.
In my 20s I wanted chaos…
now I just want things to work.
🇧🇷 I told you guys about the South of Brazil!
Do like the Brazilians do and leave organized crime hotspots like Rio and Sao Paulo where rich people have cars with bulletproof glass
Go South Brazil where you can have an actual nice life without fearing for your life
South Brazil is nothing like what you think when you think of Brazil
It's the safest place in Brazil, it's rich and feels a lot like Europe, which makes sense because it literally borders with Argentina and Uruguay
Uruguay is the richest country in South America and South Brazil is the richest part of Brazil
Florianopolis is a great start!
Magee Clegg retweeted
South America has a 10x better version of every place in the USA, for a fraction of the price.
If you like New York, Boston, or Chicago, go to Buenos Aires. A huge, walkable city with old buildings, great food, and a neighborhood for every type of person.
If you like Colorado or Montana, go to Patagonia. Glacial lakes, forests, and the Andes mountains in every direction, with all the space and privacy you could want.
If you like California wine country, go to Mendoza. The biggest wine region in South America, right at the foot of the Andes.
If you like the California coast, go to Florianópolis or the coast of Chile. Florianópolis for surf towns and island life. Chile for a thousand miles of cliffs and empty coastline.
If you like Seattle or Portland, go to Chile’s Lake District. Volcanoes, old growth rainforest, and lakes everywhere.
If you like Miami, go to Rio de Janeiro. Beaches and insane nightlife. It’s a city built entirely around the ocean.
If you like Texas or the Midwest, go to Paraguay or Eastern Bolivia. Hot, flat, cattle country, cheap land, and friendly people who barbecue every weekend.
If you like the New England coast or the Hamptons, go to coastal Uruguay. Punta del Este is the Hamptons. The towns up the coast are Cape Cod 50 years ago.
There’s a place for everyone. And it all comes with deep affordability.
Best ramen I’ve had in Santiago 🇨🇱
Goemon.
@Konst_Vatruba took me here last night. The man knows where to eat.
There are people in the USA 🇺🇸 who watch CNN or Fox News for four hours a day…
Then end their closest relationships over opinions they got from the television.
One of my favorite things about living in Chile 🇨🇱?
Nobody I spend time with talks about US politics.
Chileans 🇨🇱 eat roughly 200 lb (90kg) of bread per person per year…
After living here, I’m not surprised…
And now I’m part of the problem 😂
My weakness is the marraqueta. Crackly crust, soft center, baked in a cluster you tear apart by hand.
Bought warm from the corner panadería. Sold by the kilo. Eaten with avocado at 7pm.
In Chile, a baby who brings good fortune is said to arrive “with a marraqueta under its arm.”
I understand the saying now.
Magee Clegg retweeted
CHILE | Strait of Magellan traffic surged over 70% in Aug-Sept as Panama Canal drought and Middle East disruptions force ships to reroute.
(Emol)
A very important understanding has been lost among US citizens 🇺🇸 living abroad...
You're an ambassador for your country whether you signed up for it or not.
One of my first long stints outside the US was as a Fulbright Scholar in the Philippines…
The US Congress launched this program after WWII and has spent billions sending US citizens abroad for one reason:
To build goodwill with foreign countries, one person at a time.
Today…
Anyone with a passport and a laptop can move anywhere.
Which is amazing, but...
All it takes is one gringo flooding his building in Paraguay 🇵🇾 to begin the unraveling of 80 years of goodwill.
Unfortunately, the idiots are always more memorable.
A 49-year-old American just made the national news in Asunción 🇵🇾
His landlady asked him to leave the apartment over his behavior
According to the building manager, he responded by:
❌ Plugging the bathtub to flood the floors below
❌ Assaulting the doorman and a construction worker to force his way back in
❌ Throwing objects out the window onto the street, including a gas cylinder
Police have detained him three times... But each time he was back on the street within six hours, because that’s the legal limit they can hold him
This is the same sh*t anywhere though. Criminals always get rewarded
Anyway... neighbors have filed complaints for assault, extortion and death threats. The prosecutor’s office still hasn’t called anyone to testify
Two lessons for anyone moving here:
- Paraguay is easy to enter, and that means it also attracts people running from themselves. Changing your country doesn’t fix you
- The same slow system that leaves you alone also won’t rush to protect you. Vet your tenants, your neighbors and your building
And every foreigner who behaves like this makes it harder for the rest of us
Be a good guest
Your first stint abroad as a digital entrepreneur can be really scary…
And a complete disaster.
I’ve seen so many people dip a toe in… hate it.
Then go right back home to the life they were trying to escape because they expected the dream on the first try…
Not how this works.
After living in Asia, Europe, and Latin America, I think choosing where to live comes down to 4 things people underestimate:
How foreign do you actually want your life to feel?
Asia was incredible as a guy from the USA 🇺🇸…
Everything was different: culture, food, language, social rules.
That’s exhilarating for a while.
But after a year there full time, I realized I didn’t want everything to feel so foreign forever.
Europe was the opposite. As an American, it’s easy to get comfortable there culturally. I could absolutely live in Europe.
So why not Europe?
Which brings me to number two.
Where does your income come from?
My business mostly serves companies in the United States.
And getting dressed and mentally sharp for an 11 PM Zoom call is not fun.
You can tell yourself you’ll “control your calendar.”
But if you’re building a business, sometimes you take the call because that’s what it takes to grow.
Being on roughly the same clock as the people paying you is a massive quality of life advantage.
How much comfort do you actually want?
Traveling somewhere and living somewhere are very different things.
After a while, you want things to work.
Great gyms. Great restaurants. Good healthcare. Fast internet. Nice apartments. International flights. Modern infrastructure.
You might love spending two weeks somewhere without those things…
But living there for five years is another question.
Could you actually build a normal life there?
This might be the biggest one.
Can you make friends? Date? Build a community? Have hobbies? Get out into nature?
Would you enjoy an ordinary Tuesday there after the novelty wears off?
That’s why I landed in Chile 🇨🇱.
It’s foreign enough that life still feels interesting.
Different language, different culture, different way of doing things.
But Santiago is modern, comfortable, and connected.
I can actually build a life here.
And I’m on the same clock as my clients.
There’s no universally “best” country.
There’s just the place where your culture, work, relationships, and lifestyle fit together with the least friction.
My advice?
Don’t research it to death.
Pick a region you’re curious about.
Choose 3 cities.
Spend a month in each.
Two weeks in, you’ll usually know whether you want to stay.
And if you get it wrong the first time?
Good.
Now you know a little more about what you’re actually looking for.
Chile 🇨🇱 was designed by someone three pisco sours deep…
A desert so dry NASA tests Mars rovers in it.
Ninety active volcanoes.
Glaciers falling into fjords.
The biggest earthquake ever recorded.
And you can ski the Andes at dawn and be drinking Carménère in wine country by dusk.
I love it here.