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Today’s PrideNomad™ Quiz:

In Today’s Email:

True Confessions: Humiliation? Just $100.

On The Channel: Columbia’s Surprises

FLASH SALE: Get VIP for Less!

Battle of the Neighbors: Spain vs. Portugal. You Win!

TRUE CONFESSIONS:

Your Intuition is Smarter Than Your Ego.

I almost didn’t tell this story. It’s embarrassing. It’s infuriating. It makes me feel stupid. But it’s also honest—and I have a feeling I’m not the only one who’s fallen for something like this.

So here it is.

It was my very first night in Medellín. I was jetlagged, altitude-non-adjusted, and half-asleep when I got a message from this ridiculously adorable guy on one of the apps. He was flirty, friendly, and invited me to meet him and his two girlfriends at a bar nearby.

I should’ve stayed in bed.

But curiosity won. I figured I’d stop by, say a quick hello, and maybe head back to the hotel—with or without company. I don’t drink, so I had no desire to hang out long. But when I got there, the vibes were decent, he was cute, and I wasn’t not enjoying myself.

Then came the twist.

Just before I was about to leave, he gave me those puppy dog eyes and said,
“Come on, Big Daddy—buy us a round before you go?”

Now, I knew better.

But instead of trusting my gut, I tried to be polite. Tried to avoid awkwardness. Tried to play the “cool guy” instead of the wise one.

I said yes.

The drinks came. We stayed longer than I should’ve. Then the bill arrived—and surprise! Instead of just paying for the one round, they handed me the entire tab. Not a small one either. I was told, “We’ll get you the money after—just cover it now.”

And I did.

Because I didn’t want to make a scene.
Because I didn’t want to seem cheap.
Because somewhere in that moment, I forgot that I come first.

Was it “self-esteem amnesia”?
Whatever you call it, it was total stupidity.

By the time we left, the guy conveniently disappeared into the men’s room. The girls said they were heading to an ATM. Seconds later, they’d all vanished. I got a message from him a few minutes later: “Where are you? I can’t find you.”

Please.

They found that $100. And I found a lesson I won’t forget.

I share this not to fish for sympathy—but because I know I’m not alone. This wasn’t about sex. It wasn’t even about loneliness. It was about ego. About not listening to my own damn inner voice.

The lesson?

Stand up for yourself. Always.

Even if it feels awkward.
Even if it risks the moment.

Because people who are worth your time won’t pressure you to betray your instincts.

And if this helps even one of you avoid the same kind of scam—then I guess that $100 bought something worthwhile after all.

Have you ever fallen for a travel scam like this?
Hit reply and let me know—if enough of us share, we’ll do a full community edition soon.

Because no matter how smart or seasoned we think we are…

None of us are immune.
And the only way we protect each other—is by telling the truth.

In embarrased solidarity (and with my wallet firmly zipped shut),

Ken

ON THE CHANNEL:

What PrideNomads Need to Know About Colombia (I was surprised!)

In this video, I share:
💡 Why Colombia is rising fast on the 2025 PrideNomad Index
🌈 How Medellín is becoming a queer digital nomad haven
🧠 What most travelers still get wrong about safety here
🏳️‍⚧️ The truth about LGBTQ+ rights, visas, and vibe
✨ And why Jardín might be Latin America’s best-kept secret
Whether you’re dreaming of escape or just craving proof that joy is still possible somewhere—this is for you.

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Subscribe to 1440 today.

POST SUMMIT FOMO:

Well, the World Playground Summit may technically be over, it’s only just getting into full swing for our amazing VIP’s…

Here’s what they’ve been getting behind the scenes:

✨ Exclusive Ask Me Anything Session with Ken (Next Week)

VIP means more access, more support, more real talk. This LIVE session is your chance to ask questions, get insights, and go deeper on anything that’s come up during the summit. Wins, challenges, next steps—nothing’s off limits.

🔥 AI Freedom Formula Training (a $997 value-later this month)

Exclusive access to our brand-new live training on how to use AI to create freedom on your terms. This is a $997 program—and it’s included when you upgrade to VIP.

🎁 VIP-Exclusive Speaker Bonuses

The gifts have been rolling in—tools, free access and resources like free 1:1 consults and downloadable guides, and even discounts on queer community retreats—handpicked to help you move forward with clarity and confidence.

📺 Full Session Replays

Missed a talk or want to rewatch your favorite moments? VIPs get full access so nothing slips by.

If you’ve been thinking about upgrading… now’s your chance to get in for $50 off:

💥 FLASH SALE: Join VIP for just $147 (normally $197 during the summit)

Available until tomorrow night (Wednesday the 9th) at midnight.

We're offering this special price to remove any of those lingering excuses.

But it’s only available for a limited time—so don’t miss your chance to unlock everything.

👉 Upgrade to VIP now

No pressure—just possibility.

We’d love to welcome you inside.

P.S. Already feeling the FOMO? That’s your sign. 😉

BATTLE OF THE NEIGHBORS:

→ Spain vs. Portugal: The Visa Showdown That’s Not Really About Visas

Let’s talk about two countries at the top of everyone’s digital nomad list:

Spain and Portugal.

Both have sexy visa offers.
Both claim to welcome remote workers.
Both are remarkably queer-friendly.

And both give LGBTQ+ nomads real reasons to consider staying long-term.

And yet…

Beneath the sun-drenched rooftops and startup whispers, something else is brewing:

→ Locals being priced out of their own neighborhoods
→ Anti-tourist protests that are no longer subtle
→ A slow, simmering resentment toward foreigners—and yes, that includes nomads like us

So what happens when your freedom becomes someone else’s fight?

That’s the question more LGBTQ+ travelers are finally starting to ask.

🇪🇸 Spain: Big Queer Energy Meets Bureaucratic Curveballs

Spain’s visa is easier than it looks—especially if you’re already on the continent.
You can apply from inside the country as a tourist, which removes a lot of upfront risk.

Queer life? Loud. Present. Unapologetic.
Madrid. Sitges. Barcelona. Even Valencia is showing off.

But here’s the reality:
Barcelona locals are over it. Protests are growing. Airbnb is under fire.
In May 2025, Spanish authorities ordered Airbnb to remove nearly 66,000 listings that violated tourism and housing regulations.

And if you’re not careful, you can go from “fun guest” to “villain with a visa” faster than you can say, “I work in tech.”

🇵🇹 Portugal: Quietly Inclusive… and Quietly Angry

Portugal’s visa is stricter up front.
You need to earn more (after tax), and you’ll need a 12-month lease before you even apply.

But the cultural energy?
Gentler. Lisbon is a haven—for now. Porto still has charm. The Algarve remains dreamy. There’s a deep respect here for space, art, and softer forms of queer expression.

The problem?
Housing prices have more than doubled in recent years.
Locals are being pushed out. And in some cafés? Signs now read: “No Nomads.”

Not because they hate us.
Because they can’t afford to stay.

🌍 So… Which One Is “Better”?

On the PrideNomad Index, Spain ranks #1.
Portugal holds strong at #4.

But let’s be real—you can’t spreadsheet your way into the right life.

Because this decision?
It’s not about income thresholds or visa renewals.

It’s about who you want to become when you land.

→ Do you crave noise and celebration—or stillness and integration?
→ Do you want your life to pop… or to root?

Both are valid.
And the only way to know what’s best for you… is to try.

Consider life a buffet.
Taste freely.
If you like something, go back for more.

Because no one knows better than you what will feel like home.

🧭 What to Remember Before You Move

Visas are temporary.
So are currencies.
But how you show up in someone else’s country?
That leaves a mark.

If you go—go with curiosity.
Go with humility.
Go knowing that being welcomed doesn’t mean being entitled.

Because real belonging starts long before the paperwork.
And it lasts long after the honeymoon ends.

Wherever you go next… Go fully.

Your new life is already setting the table.
Aren’t you hungry?

Answer to Today’s Quiz

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