“What is the perfect first date that does not feel over the top?”

Overboard is my specialty, but I will behave for a first date. Assuming we’re in Miami, I want delicious food, a romantic atmosphere, and a place where we can hear each other. My go-to spots are Sunnys, Cote, or Smith & Wollensky for a sunset moment on the water. Nothing too flashy; just delicious and a good vibe.

“I want to propose over New Year but have not found the right ring. Tiffany feels overpriced. Do you have a guy?”

Designer brands absolutely have a markup. Beautiful stones without the label can be just as meaningful, but they’re not always cheaper. Big diamonds cost real money, and the entire wedding industry adds what I call a ‘love tax.’

The most important thing is working with someone trustworthy, so you’re not sold a poor quality stone or an inflated pricetag. For my high-end clients who want the very best, Wrist Aficionado is an excellent source for top-of-the line fine jewelry and rare stones. For a wider range of budgets, Ring Concierge is a strong option known for beautiful custom engagement pieces with fair and transparent pricing.

Take your time, understand what cut and clarity you love, and work with someone reputable who will source the right stone for the right price. The proposal is a moment; the ring is forever.

“Our fifth anniversary is in March. Warm getaway. I want to surprise my wife. Help.”

For holistic romance, try Aerial BVI. You get cliffside dinners, sound bath meditation next to ponies, and food grown right on the island. It feels like bliss. For an iconic European moment, Hotel du Cap Eden Roc or Villa d’Este in Lake Como are also timeless anniversary choices.

And if you’re not quite ready for that price point, I would recommend staying at Baha Mar in the Bahamas. The SLS or Rosewood offer good rooms there at a much friendlier price than Europe or the BVIs, while still giving you a stunning beach, great restaurants, and a fun but romantic atmosphere. It feels elevated and special for an anniversary, but in a way that’s easier on the budget.

“I am an F1 beginner. Is it worth going if I am not a millionaire?”

F1 is expensive, but the atmosphere alone is worth it. You do not need a $30,000 paddock ticket to feel like you’re part of the action. You can stay at Wynn or Encore for the weekend. We just wrapped F1 Vegas and the energy was unbelievable: the people, the parties, the conversations. You are fully in the mix without spending everything.

Gamble, party, network. Simply standing in the lobby bar at these five star hotels during an F1 weekend means you’re guaranteed to meet interesting people, hear wild stories, and stumble into something exciting. The whole city becomes one giant social playground. Go to the viewing parties, hop between hotel activations, hit the big dinners, explore the after parties, and then wander back to the casino at 2 AM to watch the chaos unfold.

Even if you don’t go to the actual race, you’ll still feel every bit of the adrenaline and excitement. It’s one of those weekends where opportunities find you as long as you are out and about.

“I have never been to the Middle East. Should I go to Qatar or Dubai? What is the best first-timer plan?”

Start with the icons in Dubai.

Book the Burj Al Arab or Atlantis The Royal or Atlantis The Palm.

Build your itinerary around luxury and culture. A desert safari at sunrise, dinner at Ossiano, and sunset drinks overlooking the skyline.

“I work in finance and want to spend my Christmas bonus on myself. What would your male clients splurge on?”

Rest. Real rest.

Finance guys run on pure cortisol. Book a four-day staycation at a property with an incredible spa. Get a big suite. Order room service. Disconnect. Sleep. You’ll feel like a new person afterward.

On the East Coast, I love The Cloister at Sea Island. It’s quiet, elegant, and has one of the best spa and wellness programs in the country. On the West Coast, Rosewood Miramar Beach in Montecito is an easy and peaceful reset with beautiful rooms and a calm beachfront. Internationally, Como Parrot Cay in Turks and Caicos is private, restorative, and perfect for someone who needs to disappear for a few days and breathe.

For a deeper wellness reset, there are world-class destinations that focus on longevity, detox, sleep, and complete mind and body restoration. Six Senses has exceptional programs at Vana and Douro Valley. SHA Wellness Clinic in Mexico and Spain is known for medical wellness and personalized programs. Kamalaya in Thailand is incredible for emotional and physical reset, and COMO Shambhala Estate in Bali is a favorite for a full holistic immersion. Chiva Som in Thailand and Ananda in the Himalayas offer some of the strongest wellness programs in the world.

If you want something unique, The Blue Lagoon Retreat in Iceland or JOALI Being in the Maldives offer highly personalized wellness journeys in some of the most beautiful and peaceful settings on earth.

All of these options give you something finance guys rarely get: space, silence, sleep, and the feeling of finally taking care of yourself.

“How do you plan a last minute couples ski trip?”

If Montage Big Sky or The Little Nell still have availability, take it immediately. Ship your skis, pack warm layers, and just go. The best ski homes and resorts sell out fast unless you have the right travel agent. You need someone who knows someone.

And if those are booked, look to Europe. Courchevel, St. Moritz, and Zermatt are incredible last minute options for couples. Courchevel has that glamorous ski-in and ski-out energy, St. Moritz is classic Swiss elegance with beautiful spas, and Zermatt gives you those iconic Matterhorn views that feel straight out of a movie. All three offer amazing skiing, cozy suites, great food, and a romantic atmosphere that turns a spontaneous trip into something unforgettable.

“If you had an unlimited budget, how would you spend it?”

I would move into Aman Tokyo for a few weeks and do the ultimate relaxing and food filled itinerary. Heaven. Aman Tokyo has some of the most calming interiors in the world, and the spa alone could keep me busy for days.

If I were going all out, I would book a private sushi experience at Sushi Saito or Sushi Yoshitake, both of which are almost impossible to get into unless you have the right connections. I would spend an afternoon at the Aman spa, then wander over to Ginza for a custom fragrance appointment at Shiseido or a private shopping session at one of the luxury department stores. I would splurge on a kaiseki dinner at Kagurazaka Ishikawa and end the night with cocktails at Peter: The Bar at The Peninsula or a private whiskey tasting at one of Tokyo’s hidden lounges.

Unlimited budget in Tokyo means eating well, relaxing deeply, and enjoying experiences that feel completely one of one.

“What gifting habits of the ultra wealthy can regular people copy?”

Put important dates in your calendar: birthdays, promotions, anniversaries. People love feeling remembered. It is the simplest luxury.

If you want to gift in a chic way without spending a fortune, think small, thoughtful, and seasonal. My clients love sending beautiful candles that match the person’s style, handwritten notes on thick stationery, or a favorite book with a personal message inside. In the winter, a cashmere pair of socks or a high quality blanket in a neutral color always feels expensive without actually being expensive. In the summer, a simple beach tote with the person’s initials or a high quality sunscreen set feels elevated.

It is never about the cost. It is about making someone feel seen, considered, and cared for. That is the type of gifting people remember.

“If you could recommend one hotel in the whole world, which one would it be?”

If I had to choose one property on earth, I would send you to Shebara in the Red Sea and book one of their overwater villas. It feels unreal in the best possible way. The architecture is futuristic and elegant, the water is crystal clear, and the entire experience feels like you are living on a private floating world.

The rooms are designed with a beautiful mix of modern Middle Eastern design and ultra serene minimalism. Waking up there feels like the world has gone silent. You step onto your deck, drink your coffee over turquoise water, and feel like you are completely unreachable. The staff is warm, intuitive, and discreet. The food is exceptional. The setting is cinematic.

If you want a hotel that gives you peace, privacy, design, and a feeling you cannot recreate anywhere else, Shebara is the one.

“What is the wildest request you have received and did you pull it off?”

A client once asked me for cartel diamonds. That was not happening…

Another client went vegan halfway through her yacht charter and demanded an entirely new grocery list in the middle of nowhere. The yacht was not scheduled to return for supplies. We still made it happen.

“Do your clients know you post about them on TikTok? Has it ever caused trouble?”

My clients are my biggest supporters. They watch everything like it is their own reality show. Most of them are like family to me. Many of my new clients come directly from the page.

“What is your stance on cruises?”

I love the right ones.

I am heading on a Ritz-Carlton Cruise very soon! I am also trying the Aman and Four Seasons cruises in 2026. My clients who book these ships love the large suites and the experience. 

“I am hosting for the holidays. How do I make my family and friends feel truly welcome?”

Personalization every time.

Handwritten notes at dinner. A framed photo on the nightstand. Embroidered slippers. It is not about price. It is about intention.

“What will be the next big travel destination in 2026?”

African safaris are the next wave. The Ritz Carlton property in Kenya is incredible and I always urge people to try it. It is private, immersive, and feels like stepping into a world that is entirely your own.

Privacy has become the ultimate luxury. My clients want to feel removed from the crowds. They want new experiences, but they want them to feel personal and protected. Whether it is a quick anniversary trip to Paris or a million dollar suite at the Super Bowl, the desire for unique and private adventures keeps growing. Private aviation is projected to rise significantly over the next year and the rest of the luxury market follows that pattern.

To give you an idea of how far this goes, I once had a client request that no other guests be visible during their entire resort stay. Not even in the lobby. We coordinated arrivals and departures with the management team, blocked off certain hallways, and essentially created a private hotel within the hotel. Another client refused to walk through a crowded beach, so we arranged a discreet back entrance and a golf cart transfer straight to a completely roped off beachfront section.

These are the types of experiences people are chasing now. Privacy, ease, and the feeling that the world quietly reshapes itself around them.