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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Magee Clegg retweeted
Third time visiting San Pedro de Atacama 🌵 🇨🇱 and it never ceases to amaze me.
This time, I got to visit Laguna Cejar and Tebinquinche, two places I hadn’t explored before. The first one was freezing cold, but it was absolutely worth taking the plunge.
I’ve come to realize that some of the moments when I feel happiest are those when I connect with nature🦩
When I dip my feet in the water and laugh. When I let myself be a child again and hide inside caves. When I feel the wind, when my eyes take in wonders, and when I get to experience all of this with someone I love 💕.
Thank you, Chile, for reminding me once again how beautiful you are 🇨🇱✨
A good man I met years ago died last week...
65 years old.
Built a successful business from scratch.
Three beautiful daughters.
Never smoked, and did CrossFit most mornings while the rest of us were still finding our coffee.
He'd recently retired with plenty of money in the bank…
The third act laid out in front of him, ready to be lived.
Then the doctor called...
Cancer.
That was two months ago.
And just like that, gone.
I've been sitting with this the last few days. Not because death is surprising.
It's the one thing on the schedule that never gets rescheduled...
But because from everything I've heard, he built a damn good life. And that's the part that lands. Not what he lost. What he did with the time he had.
Which brought me back to something @BuySellBA posted recently:
"What if you only had 3 years left to live?"
I know what the easy answer sounds like. I've lived in 6 countries, been to over 60, and spent most of my adult life ignoring whatever I was supposed to be doing…
People assume a guy like that already has his answer.
I don't.
Because here's the thing nobody tells you about chasing the life you want:
you still accumulate a waiting room. Calls you keep meaning to make. The trip you've been "about to" book since 2021. People you love who are getting older in a different time zone while you tell yourself there's time.
There isn't. There's just the illusion of it.
So I'm asking the uncomfortable ones this morning.
What am I actually putting off?
Who do I want more time with, and why am I not already on a plane?
What fear is still running the show?
And what is the worst thing that happens if I just do it?
Even this gringo living the dream en el culo del mundo has to sit with those questions once in a while.
This morning they're sitting with me.
We spend our whole lives obeying the quiet voice that says what we're supposed to do.
The louder, better question is what we actually WANT to do.
Then go do it. Before the doctor has a reason to call.
Every single time I've followed that instinct, life has gotten a hell of a lot more interesting.
Most people are waiting for retirement to see places like this…
I just came for the weekend.
Chile 🇨🇱❤️
U.S. citizens 🇺🇸 Google how to move to Canada 🇨🇦
Brazilians 🇧🇷 Google how to move to Paraguay 🇵🇾
Every country has somewhere its citizens threaten to move after an election…
But almost nobody actually goes.
Except the Brazilians 😂
23,500 got Paraguayan residency in 2025.
Another 22,600 in the first half of 2026.
As a foreigner living in Chile 🇨🇱…
Every time I’m out drinking piscolas with Chilean friends, the same debate comes up…
“who pays on the first date?”
I’m surprised by how many guys expect her to split it. Or quietly pray she offers 😂
If I ask a woman out, I’m picking up the damn check.
💙💔 Feel so sorry for females today. There are so many male losers out there in the world today.
This girl dodged a bullet. Guys that talk about ROI and dates are morons.
Have run into this so many times hearing guys talk about this. Or guys expecting the girl to pay half of the date.
We have slid so far away from normal. The good news for guys that are not creeps and gentlemen is that it's very easy competing against these kind of guys.
In Chile 🇨🇱
Qualifying small businesses pay just 12.5% in corporate income tax…
And President Kast wants to make that rate permanent.
The fine print:
• Your company needs to average roughly $3M USD or less in annual revenue
• The 12.5% rate is temporary and starts climbing after 2027
• Larger companies are getting a cut too: 27% down to 23% by 2029
The permanent 12.5% isn’t law yet. The bill is expected to reach Congress in November.
But if Kast pulls it off…
Chile won’t just be el mejor país de Chile 🇨🇱
It could become one of the most interesting places for digital entrepreneurs to build a business.
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.