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Letters from Italy

Happy 13th Tuesday of 2026,
I’m in Venice today, but it’s Tuesday — so I’ve inked my pen and I’m writing away on this newsletter. Why? Because 99% of humans give up on their new year’s goals. And I wanna be a human that’s in the top 1% who keeps their word like its their bond. If that’s not your vibe, unsubscribe.
If it is, keep reading.
Yes. Welcome back to Stay Curious — a newsletter I write once per week on 3 things keeping me curious, or I send one of you a 100 dolla bill for catching me if I skip.
Here’s what’s on my mind this week:
1. Leonardo da Vinci’s Checklist for a Perfect City

On my flight to Venice, I started digging into the Leonardo da Vinci book by Walter Isaacson. And tbh, it’s fire. So many golden nuggets. One of my favourites I ran into today was his checklist for a great city.
I thought you could read it and put it up against the current city you’re living in
Freedom
people can think, build, and create without friction
A wealthy, well-dressed population
not just surviving… visibly thriving
Clean, pure water
basic, but non-negotiable
A strong university
ideas flowing as much as money
(he literally called out teaching both Greek + accounting)
Masters of every craft
artists, engineers, builders, makers
Global commerce
banks + business agents connected to the world
Power + influence
a city that actually matters beyond its borders
Walter (the author of the book on da Vinci) literally called out that the reason Leonardo was so successful was due to the fact that he was born in Florence at this time, where all 7 of these things were intersecting with the city he was living and building his career in.
Pretty interesting, eh?
2. What’s Worse For Health: Loneliness or Smoking?
Something I always think about when I’m in Europe is how social everyone is.
You look around at cafes and everyone’s:
having an Aperol spritz
smoking a cigar
talking with their hands
enjoying a cappuccino
Then when I’m in North America, and I look around at cafes, people are:
on their laptop
on their iPhone
listening to their AirPods
No alcohol or cigar in sight
They’re alone on their phones, but they're “healthy” b/c they’re not smoking or drinking. But are they?
What’s really worse for you? Always gets me thinking.
3. Beautiful Chaos vs Calculated Calendars
The last couple of days I’ve fallen in love with the beautiful chaos of the streets of Venice. If you’re type A and married to your phone for GPS settings, you’d hate it here. But if you’re into the idea of “lingering” and getting lost or drawn to wherever the vibes may lead you, this is your place.
So much of my day-to-day life is calculated. Meetings. Gym. Dinners. Hangouts.
Italians operate under a beautiful chaos that enables them to linger, spill over into the streets and get lost into wherever something may lead them next.
And I am into that energy.
Are you?
P.S. Sign up to our fireside chat with the Poppi Founder April 2nd if you wanna hear how she sold her startup for $2Billion to Pepsi.
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Joel
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