☕️ (R)emote Expresso #52

☕️ (R)emote Expresso is your weekly dose of creator insights on remote collaboration designed to fuel your day, delivered once a week in your inbox 💌

Hey Remote Dreamers, Strategic Founders & Quiet Hustlers,

What if your biggest deal of 2025 didn’t start with a pitch deck…

…but over a glass of vinho verde on a cliffside in Madeira?

Every year, hundreds of seasoned founders, community builders and ambitious freelancers head to the Nomad Island Festival — not for slides and stages, but for something deeper.

Not a retreat.

Not a conference.

A one-week business experience designed to unlock your next level.

This isn’t for the curious. It’s for the committed.

And this year, we’re going as a community — with backstage access, real perks, and the chance to scale smarter, not harder.

Let’s unpack why this might be your best decision of 2025 👇

✨ You Deserve a Smarter Way to Grow

Imagine this.

You’re on a cliffside terrace in Madeira, cocktail in hand, surrounded by people who get it. Founders, creators, and remote leaders who aren’t here to pitch — but to partner. Someone next to you just signed a new client. Across the table, someone else found their next CTO.

You? You’re finally breathing again — and you’re not even halfway through the week.

Welcome to the Nomad Island Festival 2025.

Seven days to scale your business, reconnect with your drive, and meet the people who will change your next 12 months.

🚀 Why This Isn’t Just Another Retreat

Forget the awkward networking, endless keynotes, and overpriced hotel coffee.

This isn’t a conference. It’s an experience — crafted to move you forward on every level.

🧠 In the mornings, you’ll dive deep:

Practical workshops led by global experts. From scaling without burnout to pitching with purpose, every session is built to help you implement — not just take notes.

💬 In the afternoons, real connections happen:

You’ll co-work with people building real things. You’ll hike, dive, and dine with humans who might become collaborators, investors, or lifelong friends.

🌙 And in the evenings, you’ll recharge with intention:

Thematic dinners. Rooftop DJ sets. Fireside conversations.
Because growth without joy is just another job.

🤝 What makes this year different

The Nomad Island Fest isn’t just another event. It’s a curated gathering for founders, creatives, and remote leaders who want more than likes and leads — they’re looking for clarity, alignment, and deep human connection. Just like we are.

From the first mastermind breakfast to the last clifftop dinner, what you’ll find in Madeira is a community in motion: generous, grounded, and unapologetically ambitious.

We’re proud to partner with The Nomad Escape to offer our members an exclusive 20% off — not because we think it will sell out (it will), but because we genuinely believe this kind of space should be accessible to the right people, at the right moment.

🌴 Ready to take the leap?

When: December 4–10, 2025
Where: R Generation Hub live room
Duration: 7 days of curated connections, strategy workshops, and unforgettable experiences in a 4-star oceanfront setting.

💸 How much?

• Basic Pass €1,076 (instead of €1,345)

• Premium Pass €2,396 (instead of €2,995)

Use the promo code RGEN2025 to unlock your 20% community discount.

🧳 Next steps?

Sales will close on November 25th, and this event sells out fast. If this sounds like your kind of December reset…

Here's what you actually need:

You’ve read the posts. Taken the courses. Followed the experts. But growth doesn’t happen in isolation. It happens in motion — and in the right rooms.

Nomad Island Fest isn’t just a getaway.

It’s a powerful convergence of ambition, clarity, and momentum — curated for those who don’t just dream big, but build big.

You might come for the workshops, the coastline, or the people.

But what you leave with — connections, confidence, and capital — could be the best business decision of your next 10 years.

See you on the island 🏝️

— The (R) Generation Team 🧡 💪

👨‍💻 Big Desk Energy: our biggest startup insights, & stories

✈️ Nomad Cloud: get the latest on remote work and location independence.

🌎 Thrive Remotely: lifestyle and wellness for remote workers

👩‍🎤 Customer Success Jobs: our remote high-paying jobs for you

🤖 Americans Abroad: insights about visas, residency, & cost of living

🔴 Creator Spotlight: inspiration for world class creators journeys

BE A PART OF
THE R GENERATION COMMUNITY

R GENERATION brings together remote professionals from 50+ countries to explore the future of work through events, workshops, and AI-powered collaboration. Join a community where curiosity meets innovation and connections transcend borders.

Join us where bold ideas meet global community, and where we protect what we've taken back - together.