Gianna's Gem: Five Unforgettable Event Experiences for C-Level Executives

Hi there,

A few months ago, I was chatting with a CMO at a dinner I had planned, watching her genuinely laugh with delight for what she told me later was the first time in months. We were at a private celebrity chef’s vineyard, the chef was presenting the first course which featured hand-pulled mozzarella that she and her colleagues had made themselves earlier that evening, and the sun was doing that golden California thing it does right before it disappears.

She leaned over and said: "This is the most authentic joy and connection I’ve experienced at a work event in years - why aren’t we doing these more often”?

That's the whole point.

After 23+ years designing experiences for executives at Google, Amazon, SoftBank Vision Fund, Airtable, Cognition and others, I can tell you with complete confidence: the conference room is not where relationships are actually built. The suite upgrade and the branded tote bag are not what people remember. What they remember is the moment they didn't see coming. The experience that made them feel something. The connection that would have only happened from meeting another person out of the typical work context and connecting on a human level at a shared experience.

C-suite executives are the hardest audience in the world to impress. They've been everywhere. They've seen the standard playbook so many times they can predict the next move before you make it. And yet - and this is what I find endlessly exciting about my work - they are just as susceptible to genuine delight as anyone else. Maybe more so, because they encounter it so rarely.

Gianna's Gem: The most powerful thing you can give a C-level executive isn't access or information. It's an experience they couldn't have planned for themselves, shared with others who are experiencing the magic simultaneously.

This week I’m sharing five of my favorites, the ones I come back to again and again because they work, and they’re timeless.

It’s crazy season, so this week I’m giving you a more snackable overview of the concepts, but please get in touch if you’d like to have a brainstorm session on any of these concepts that sound intriguing.

1. The Mystery Private Jet Experience

Guests board a private jet knowing only what to wear, and the duration of the evening’s experience, not where they're going. The plane itself is part of the experience: curated beverage service, facilitated conversation, and an atmosphere of intrigue. The reveal might be a Napa Valley vineyard with a celebrity chef waiting at the vines, or a mountain setting with a private musical performance under the stars. The return flight is equally intentional, relaxed, reflective, and memorable with dessert and warm cozy beverages or night caps served as guests choose who they want to sit next to for a deeper conversation to close out the evening meaningfully.

Why it works: Anticipation is a powerful emotional primer. By removing the destination from the equation, guests arrive fully present, curious, connected, and ready to engage in a way a known itinerary never allows. It also leads to word of mouth storytelling since this is not the standard event format.  When you bookend the destination with intimate opportunities for conversation, the result is bonds and conversations that are much more meaningful that any networking dinner.

• Attendees: 8 – 30 guests. 

• Timing: Half day or 4-hour evening is optimal for this Executive Crowd.

2. The Executive Tailgate

Forget the standard hospitality suite. Instead wy not create a private, white-glove tailgate featuring a local celebrity chef who brings the region's culinary identity to life before kickoff. Think wood-fired brisket, craft cocktails, live music, and the energy of game day, all in an exclusive, curated setting. Box seat tickets to the game, of course, complete the experience.

Why it works: Sports create common ground across titles and industries. Pairing that with the nostalgia of a tailgate, up-leveled with exceptional local food and hospitality turns a game into a genuine cultural experience that guests will talk about long after the final score.

• Attendees: 15 – 50 guests. 

• Timing: Half day.

3. The Ranch Retreat

A working ranch setting becomes the backdrop for a day of unexpected activities such as axe throwing, falconry demonstrations, horseback rides, custom cowboy-hat fitting and monogram branding. As the sun sets, guests gather for an evening meal featuring locally grown, seasonal cuisine, with the land itself as the centerpiece. Rustic, intentional, and deeply grounding.

Why it works: Executives love competition and pairing it with unique physical and grounding activities away from city/office life helps them reconnect and engage. Activating that instinct and pairing it with stillness at the dinner table where they can share their experience creates a powerful arc from adventure to reflection that strengthens bonds quickly.

• Attendees: 12 – 40 guests. 

• Timing: Full day or overnight.

4. The Closed-Door Tasting Room

A private session with a master sommelier or whiskey distiller in a venue not open to the public such as a private winery, a working barrel room of a cult wine or whiskey, or a private home. Guests taste through rare and library selections no available for purchase, guided by someone who makes the subject come alive and paired with cuisine that is as beautiful as it’s delicious. Think imported cheese, locally grown fruit that’s harvested that morning paired with locally sourced meat and fish and served on artisanal ceramics. Small groups only. No phones at the table. A bonus if you can provide access to something at the venue that is truly priceless. 

I once hosted guests at a venue that featured a famous Film Director’s private art gallery and it was one of the most memorable aspects of the event for guests to tour the gallery and identify/share their favorite piece of art as a conversation starter).

Why it works: Access is the ultimate luxury at the C-suite level. When guests experience something they genuinely couldn't arrange on their own, it signals respect for their time, and creates a shared story worth telling. 

• Attendees: 6 – 20 guests. 

• Timing: 2 – 3 hours.

5. The Sunrise Summit

An early morning guided hike, canoe ride, or scenic drive to a breathtaking overlook, timed perfectly for sunrise. A private chef or catering team awaits at the top with a beautifully prepared champagne-breakfast spread. Minimal agenda, maximum atmosphere. What gets said over coffee at elevation, at this hallowed time of day, watching the world wake up, tends to be far more honest, and far more memorable, than anything said in a boardroom.

I once hosted test-drives of the most priceless luxury vehicles for CEO’s at SoftBank Vision Fund’s CEO/Investor Summit at sunrise in the canyon of LA. Being able to drive those roads when they were traffic free, and then pause to enjoy fresh-made espresso and breakfast overlooking the ocean was a story I kept hearing the executives talk about throughout the day. 

Why it works: Starting the day before the noise begins strips away the armor. The shared effort of getting there, combined with natural beauty and nourishment, creates authentic connection faster than almost any other format.

• Attendees: 8 – 25 guests. 

• 2-3 hours first thing in the morning.

I've produced versions of all five of these for executive audiences across tech, finance, and even for celebrities and I can tell you that the right experience for your group depends on who's in the room, what relationships you're trying to build, and what you want people to feel when they go home. That's the part that can't be templated.

If any of these sparked something, reach out. I'd love to get on a call and help you imagine what extraordinary looks like for you.

Have an extraordinary week!

XX, 

Gianna

What I’m loving this week: Savvy Sleepers Dallas Getaway Guide

If you know me, you know I don't recommend things lightly. So when my friend Dale Schroeter, a woman who spent years as a bona fide tastemaker in Dallas, someone who genuinely knows that city from the inside out, publishes a destination weekend guide, I read every word. And then I immediately forwarded it to three people.

Dale's piece for Savvy Sleepers, The Perfect Weekend in Dallas, is exactly what the best travel guides are: opinionated, specific, and written by someone who has actually done the research with her own two feet. She covers it all: where to stay (The Joule and Hotel Crescent Court are on the list, and for good reason), where to eat (Monarch at the top of Hotel Swexan, Sassetta, Pecan Lodge in Deep Ellum), and where to wander (Katy Trail in the morning, Highland Park Village in the afternoon, Bird Bakery for a vanilla cake that will genuinely change you).

A few of my personal highlights from the guide: the case she makes for a Dallas Mavericks game, even if you don't follow basketball, she's right that American Airlines Center is one of the best arenas in the country and the tickets are shockingly affordable. The Harwood District morning coffee suggestion is perfection. 

What I love most about Dale's guide is that it reflects how she's always thought about a city not as a checklist, but as a feeling. Where to go to feel like yourself. Where to go to feel a little elevated. Where to go to make a memory.

And speaking of making memories with a group, I was recently on Fox Good Morning Dallas sharing my favorite tips for planning group trips without the stress. Whether you're planning a girls' weekend or a bigger gathering, so much of it comes down to a few smart decisions made upfront. You can watch the full segment here if you’re in search of group event or vacation tips stat: fox4news.com/video/fmc-2aruboxutn9k2rgl

Dallas is more than worth the trip. Read Dale's full guide at Savvy Sleepers — and then start planning.