Another Year Around the Sun
Sending this from Bologna, Italy - August 10th - MY BDAY
I came to Italy to reset. A week between Bologna and Venice, solo, with no real agenda except to slow down, eat well, and clear my head. I’m sending this from a café in Bologna on my birthday, and I’m not going to sugarcoat it — three weeks after my last newsletter, life threw me another curveball. As Jamie Dimon said at a recent Acquired Podcast event I attended at Radio City Music Hall: “Shit happens.” Not the first, and I’m no stranger to setbacks. Like every time before, I’m coming back stronger.
Here’s what I know about setbacks — they’re data, not verdicts. You process it, learn what you need to learn, and use it as fuel to build something better.
So while Italians are out here mastering the art of slowing down, I’m doing the opposite. On the 10th is grinding. This isn’t some soft birthday reflection — it’s a gut check. When life swings, you either fold or fight. I fight. And if you’re still out here booking cookie-cutter trips and calling it luxury, we need to talk. Airport hotels? Tourist trap selfies? Olive Garden in Times Square? Come on. You know better. So do better. This year taught me one thing: average is optional. Let’s raise the bar — in travel, in business, in life.
On the 10th — Why I Started
A year ago, launching On the 10th felt like something people with big followings and deep thoughts did — not me. But I hit publish anyway. Apparently, I’m okay talking to myself in public.
Growth was — and still is — humbling. We’re talking “three friends and a cousin” level. But here’s the thing: friends started replying. A few mentioned they actually enjoyed what I was writing. That was enough fuel to keep going.
This was never about chasing followers or building some media empire. It’s about showing the real work of building Roam & Shine — the wins, the pivots, the 3 AM ideas, and the inevitable face-plants. It’s public accountability. It keeps me sharp. And it’s proof you don’t need perfect timing, a big plan, or a massive audience to start. You just need to hit send.
The Year around the Sun in Stamps
This year’s travel wasn’t just for fun — it was research. Seoul, Mexico City, Hamburg, Madrid — I moved with intention. Not to escape, but to understand what actually makes travelers happy, not just what looks good on Instagram.
Seoul reminded me luxury isn’t always thread count deep. I stood at the DMZ, explored ancient palaces, and dove into a café scene that makes Brooklyn look chill. The Four Seasons delivered, but the real magic was watching a city blend tradition and tech in one breath. (Click here to read my full insiders guide to Seoul)
Mexico City hit different — ancient pyramids by day, Michelin-level bites by night. But the moment? Sabering champagne at the St. Regis for my mom’s 75th — a private ceremony made possible through the hotel partnerships I’ve built as a travel advisor. That’s the kind of VIP moment I can pull off for any client. Because sometimes luxury isn’t marble — it’s the meaning behind the experience.
Summer brought Europe at full throttle — Montenegro’s family-run vineyards, Bordeaux doors that opened because of the right connections, Croatian seafood that made my iPhone camera cry.
Hamburg was my reset. No plans, just breathing. Madrid reminded me why nights start at midnight. LA? A quick rooftop moment to remember: confidence travels better than any carry-on.
Now in Italy, I’m reminded that “live well” isn’t a slogan, it’s a lifestyle. Every stop sharpened something -my taste, my perspective, my sense of what travel should be.
Truth is, most people chase aesthetics over experience. They’re curating for followers instead of collecting real memories. And they’re missing the whole damn point.
Building the Travel Advisor Game
Here’s where things shifted from “I love to travel” to “I’m building something that moves the needle.” Eighteen months ago, I became a travel advisor — not just because I’m obsessed with passport stamps, but because I saw how lost people are when it comes to planning a great trip.
Most think luxury means a bigger room or a bowl of fruit. Meanwhile, I’m texting GMs, calling concierges who know my name, and unlocking experiences most people don’t even know exist.
Free upgrades, daily breakfast, resort credits, early check-in, late checkout — all from a single message to the right partner. These aren’t Expedia perks. They come from real relationships I’ve spent years building.
And it goes way beyond hotels. I’m curating F1 experiences that put you trackside. Private tastings at cellars with no websites. Tables you’ve only seen on chef documentaries. Roam & Shine doesn’t just book — we engineer the trip people brag about for years.
Beyond Hotels: What's Next?
Here’s where things get interesting. I’m building a concept with an old college friend — merging curated luxury travel with exclusive access to high-end products through trusted, authorized sellers.
The idea? You’re already spending on luxury. But what if that purchase came with a moment worth remembering? Like a trackside F1 weekend tied to a limited-edition watch drop. Or a Mediterranean yacht trip where your rare wine collection gets the spotlight it deserves.
This isn’t shopping — it’s celebration. Milestones turned into once-in-a-lifetime experiences.
I’m also teaming up with private chefs and elite fitness pros to create retreats that actually reset you. Think sunrise yoga on the coast, followed by chef-led dinners with ingredients picked that morning. Or Hamptons weekends that blend serious training with serious indulgence. I’ve even been talking with a fellow advisor and certified yoga instructor about curating small retreats in the Catskills, where I have a cabin and five acres of open space for yoga, meditation, and outdoor workshops—paired with farm-to-table dining and local adventures.
The vision is simple: high-touch, meaningful experiences that go beyond the expected. You won’t find these on booking sites. You’ll remember them forever.
Most people settle for basic luxury. I’m building the kind that stays with you.
What This Means for You
Let’s be real — you can book your own trip. Spend hours scrolling TripAdvisor, reading reviews from people who think Applebee’s is fine dining. Refresh hotel sites hoping for a deal. Stand in line for the same five Instagram spots.
Or — you could let me handle it.
Milestone birthday? Multigenerational trip? Honeymoon that makes your friends question their relationships? I don’t just deliver. I make it look effortless.
My rates? On par with the big booking sites. For full-on curated experiences, there’s sometimes a small premium — but the value? Unmatched. And unlike a call center or some ghosting chatbot, I’m here when it counts.
Want luxury hotels, full itineraries, even business or first-class flights? Done.
You show up ready to enjoy. I handle the rest.
Chapter Two Starts Now
As I hit send from Bologna on my birthday, here’s what I know: that curveball three weeks ago? Might’ve been the best thing that could’ve happened. Sometimes life needs to shake you up so you finally build what you’re meant to.
Roam & Shine may still be a side hustle — but I’m done treating it like a side thought. This thing is growing, and it's changing how people think about travel, luxury, and what’s possible when you stop settling.
Every GM who texts me back. Every chef who actually cooks instead of just posting. Every connection I’ve built? It’s all been leading to this.
So here’s your wake-up call: stop putting off that trip. Stop waiting for perfect timing or telling yourself stories about why now isn’t the moment. Life’s already happening.
You want basic? Book it on Expedia. You want unforgettable? DM me, call me, email me. Best case — I plan the trip of your life. Worst case? You get free advice from someone who actually gives a damn.
