Hi there,

Last week, I attended the “Super Bowl of tech events”, AWS Re:Invent. An event I formerly planned while on the AWS Training and Cert team, and now as a consultant, help clients attend and stand out in meaningful ways. It’s an event that is a necessary evil (IMHO) as there’s the cost in NOT showing up when your competition is there, but it’s also extremely challenging to get attendee attention in an event with 60K attendees and 500 events happening simultaneously.

This year, I wanted to try something different…an executive event so magnetic that attendees would remember it days later. The concept? A poker tournament that proved sometimes the best business conversations happen when you're betting on a pair of jacks.

There's a reason why tech executives—from the All-In podcast hosts to Silicon Valley's most successful founders—are obsessed with poker. It's not just a game; it's a masterclass in decision-making under uncertainty, reading people, managing risk, and knowing when to go all-in. Poker mirrors the executive experience itself: incomplete information, calculated bets, and the ability to maintain composure when the stakes are high.

Let me break down why this event succeeded in executive engagement—and how you can apply these principles to your next high-stakes gathering.

The Hook That Actually Hooked Them

Here's the thing about executive events during massive conferences like re:Invent: your audience is drowning in dinner invitations and cocktail hours. Everyone's offering drinks. Everyone's promising "networking." So how do you stand out?

Gianna's Gem: The best event invitations don't promise networking—they promise an experience that’s engaging and offers a clear CTA (call to action).

This event led with a poker tournament, and the prize was worth playing for: two US Open tickets and VIP hospitality (valued at $3K). As one attendee shared with me during the cocktail hour, "That's what got my attention." Not another wine-and-cheese reception. Not another "please come network with us" ask. An actual, competitive, engaging activity with a prize that signals "we know you're successful, and we're offering something worthy of your time in an intimate setting where we’ll also feed and entertain you."

Poker is also a "birds of a feather" signal. When you invite executives to a poker tournament, you're not just offering entertainment—you're curating a room of people who share a common language, appreciate strategic thinking, and understand the thrill of calculated risk. It's instant bonding through shared values.

The psychology here is brilliant. Poker tournaments create what behavioral economists call "active participation"—you're not just showing up, you're invested. You're thinking. You're engaged. And most importantly? You're sitting next to someone for extended periods, which is how real relationships actually form.

Layering Delight and elevating emotion strategically: The Magician Element

But here's where this event went from good to unforgettable: we brought in a magician. Not just any magician—a skilled performer who wove card tricks into the poker theme and created awe and delight before the tournament got started. The laughter and delight that rang out in the air when he shocked and awed the most discerning and cerebral executives set the mood that this was going to be a memorable event of Executive caliber. PS - Dennis is my favorite magician in residence from The Battery and you can book him using a discount code for my Gems here.

Second, we had an AI-generated portrait station where attendees could get custom caricature drawings generated by a bot in real-time. This wasn't just entertainment; it was experiential. While guests waited for their portraits, they naturally networked and filmed the cute bots (and then shared on their social feeds). When they received their drawings, they immediately pulled out their phones to share on social media—tagging the event, tagging each other, creating organic buzz that extended far beyond the room.

Gianna's Gem: The best events create moments of unexpected delight that disrupt the "just another corporate dinner" narrative and elevate emotions which later translate to brand affinity as your brand is associated with positive emotions and experience.

Think about the emotion this creates. You're at a business event, but suddenly you're experiencing genuine wonder. That magician isn't just entertainment—he's a pattern interrupt. He's creating that "you had to be there" moment that makes attendees want to share the experience. It's story-telling-worthy without trying too hard. It's memorable without being gimmicky.

The tie-in to the poker theme shows intentionality. This isn't random entertainment; it's curated to enhance the narrative of the evening. Cards. Strategy. The element of surprise. It all coheres.

The Psychology of Premium Food & Drink

Now let's talk about what happened before and after the tournament during the 7-8pm and 10-11pm reception windows. This is where the strategy is in the details and execution. The menu was enticing and premium:

Raw bar
Grilled and carved tomahawk steaks, salmon
Poke Bar
High quality passed appetizers
Premium wines, cocktails and ports

Gianna's Gem: Exceptional food and wine aren't luxuries at executive events—they're neurochemical strategies for building trust and closing deals.

Here's what most people miss: when we share exceptional food and drink, our brains release oxytocin—the bonding hormone. Cortisol drops. People feel like they’re being taken care of and feel gratitude. That executive who was skeptical about your pitch? They just shared a perfectly seared tomahawk steak and bourbon with you while discussing their favorite vacation spot. You're no longer vendor and client—you're two people who just had a memorable experience together.

The raw bar and premium wines signal something else crucial: "We value quality, and we value you." These choices say, "We're not cutting corners on this relationship."

And let's be honest—at a massive conference like re:Invent, where attendees are running between sessions and grabbing whatever they can, offering a genuinely excellent meal solves a real pain point. You're not just feeding them; you're rescuing them from another mediocre beer and pizza experience.

The Intimate Architecture of Poker Tables

Here's something I love about a poker tournament for Executive event design: poker tables force intimate conversation.

Unlike cocktail receptions where people drift and network superficially, poker creates what I call "enforced intimacy"—you're literally sitting shoulder to shoulder next to people for extended periods. But here's the magic: rather than feeling stuck at a dinner table next to people, you actually start to bond at these tables and get to know the other players in a more authentic (rather than forced) networking setting.

Gianna's Gem: The best business relationships aren't built in 30-second elevator pitches—they're built in 30-minute conversations where business happens to come up naturally.

While you're focused on your cards, conversations naturally spring up around your kids, your company challenges, your golf game, your thoughts on the keynote you just saw. The poker becomes the vehicle for the conversation in a subtle way.

The reception windows (7-8pm pre-tournament and 10-11pm post-tournament) were strategically set as well and intended to give our sales and leadership opportunities to circulate, make introductions, and capitalize on the goodwill created by the experience. People who just had fun together are far more receptive to business conversations and naturally start inquiring more about the products (people psychologically feel a need to repay positive gestures).

Giveaways That Keep Giving

The event didn't stop when guests left. Three smart takeaways ensured the evening had durability for our brand:

AI-generated caricature drawings - Every attendee left with a personalized piece of art. This wasn't just a standard giveaway; it became another interactie component of the experience that delighted people, generated social posting/videos of the cute AI drawing bots, and became a conversation starter that sits on someone's desk for months after the event, reminding them of the positive experience they had wth our brand.
Custom card decks - Branded but tasteful, these reinforce the poker theme while serving as a practical item people will actually use and see regularly (and over the years) as a reminder of our event, whether they’re used for playing card games or performing magic tricks!
The US Open tickets prize - This created social sharing opportunities throughout the event ("Who's winning?" "What's at stake?") and post-event as the winner celebrated their prize on social and via word of mouth.
We created a physical prize for the Poker Tournament winner (DM me for a photo of what this was!) so they could place it proudly on their desk and likely share about it on social and with many other people they encountered daily in meetings, etc.

Gianna's Gem: Great event swag isn't about randomly placing your logo on merchandise that will likely be chucked —it's about creating physical reminders of the emotional experience you created together.

These weren't random tchotchkes. Each item tied back to the experience and served as a memory anchor. Months from now, when that executive sees their caricature or shuffles those custom cards, they're not thinking about your product—they're remembering how you made them feel.

The ROI of Experiential Executive Events

Let's talk business impact. Events like these cost more than a standard dinner. The magician, the premium food, the prizes, the custom giveaways—it adds up. So why is it worth it?

Because you're not buying dinner—you're buying mindshare.

At a conference with 60,000+ attendees and hundreds of competing events, you created the one people actually attended and talked about / shared about afterwards. You created the one that felt exclusive without being exclusionary (we had different levels so everyone felt they could participate, and others who just wanted to watch as spectators which was also entertaining). You created real conversations, not forced networking.

And here's what research consistently shows: deals happen when relationships exist. Relationships happen when shared positive experiences create trust. Trust happens when people let their guard down. And people let their guard down when you create an environment that's genuinely enjoyable—not transactional.

Key Takeaways for Your Next Executive Event

If you're planning a high-stakes executive event, here's what this poker tournament teaches us:

1. Lead with the hook, not the ask

Don't invite people to "network." Invite them to compete, experience, enjoy.
Make the experience the story, not your company.

2. Layer your experience strategically

Activity (poker tournament) = engagement and enforced conversation
Surprise element (magician/AI photo bot) = delight and shareability
Premium F&B = trust-building and pain point elimination
Structured timing (pre/post reception) = sales opportunities

3. Design for the story they'll tell

"We went to another vendor dinner" vs. "You won't believe the poker tournament they threw"
Which story would you rather have attendees telling?

4. Create memory anchors

Physical items (caricatures, card decks) that trigger positive recall
Prizes that generate social proof and aspiration
Moments (card tricks, winning hands) that become "you had to be there" stories

5. Solve real problems

At a massive conference, great food solves the "I'm exhausted and haven't eaten well" problem
At a week of networking, structured activity solves the "another awkward cocktail reception" problem and adds some play, delight and awe into the long week
Memorable experiences solve the "how do we stand out" problem

The Bigger Picture

What I love most about this event is that it understood something fundamental: in an age where everyone's doing "immersive experiences" and "activations," sometimes the most innovative thing you can do is create genuine human connection.

Poker isn't new. Magic isn't new. Great food isn't new.

But combining them thoughtfully, with strategic timing, premium execution, and authentic hospitality? That creates something your competitors can't easily replicate—because replication requires understanding not just what you did, but why it worked.

Gianna's Gem: The best events aren't the ones with the biggest budgets—they're the ones where every dollar spent ladders up to a cohesive experience that makes people feel something.

This poker tournament didn't just feed executives and hope for the best. It created an emotional journey: anticipation (the invite), excitement (the competition), delight (the magic), connection (the intimate table conversations), satisfaction (the food and wine), and lasting impression (the takeaways).

That's not event planning. That's experience design. And in the world of high-stakes executive engagement, that's what separates the forgettable from the unforgettable.

In a world where AI can automate so much, the experiences we create—the moments of genuine connection, delight, and human warmth—become more valuable, not less.

So the next time you're planning an executive event, ask yourself: Am I designing an obligation or an experience? Am I offering another dinner or a story they'll want to tell?

The answer to that question might just determine whether your event gets forgotten by Tuesday or remembered for years.

What I'm Loving This Week: Monet

Speaking of revolutionizing the events industry, I'm thrilled to announce that I've joined an early stage but very hot event tech startup, monet.io as an advisor.

Here's what really blows my mind: Monet can generate entire showfloor layouts for conferences and expos—something that traditionally takes weeks of back-and-forth with venue teams, agencies, sponsors, and operations. The platform doesn't just create a generic floor plan; it uses intelligent algorithms to recommend optimal sponsor booth placements based on traffic flow, sponsor tier, and strategic visibility.

Think about what this means for event planners managing large-scale conferences: instead of manually juggling sponsor requirements, attendee flow, and venue constraints in CAD software or PowerPoint, Monet does the heavy lifting while you focus on the strategic decisions. It's like having an expert event designer and operations manager working 24/7 on your team.

For sponsors, this means better ROI—their booth placement isn't arbitrary, it's data-driven. For attendees, it means better navigation and experience. For planners, it means hours (sometimes days) of work condensed into minutes.

If you're managing complex events—especially in the enterprise space where showfloors, sponsor management, and multi-stakeholder coordination are involved—I encourage you to check out what the Monet team is building. They're not just creating software; they're creating space for event professionals to do what we do best: design experiences that matter. Drop me a line if you want an intro and a Gianna’s Gems VIP discount on their product.

Learn more at monet.io

Gianna Gaudini is an event strategist, advisor, and author of the Amazon bestselling book "The Art of Event Planning." She's held leadership roles at Google, AWS, SoftBank Vision Fund, and Airtable, creating unforgettable experiences that drive business results. For more insights on creating exceptional events, visit GiannaGaudini.com or connect with her on LinkedIn.

Interested in having your event or venue featured in Gianna's Gems? Reach out at gianna@gaudini.com