Meet Your Guide

I’m Cory, and I built Pivot Trip because I wanted to travel the way I love—off the beaten path, away from crowds, exploring authentically and safely. After visiting 100+ countries across all 7 continents, I knew there were other gay men who wanted the same: depth over parties, culture over tourist traps, real exploration over cookie-cutter excursions.

Cory with the Egyptian pyramids in the background

Why Pivot Trip Exists (And Why You Should Care)

The Journey

I left corporate in October 2017. After 16 years in investment banking and Fortune 50 strategy, I was done. I booked a ticket to Antarctica to complete my 7 continents and figure out what I actually wanted to do with my life.

That trip changed everything. I realized I was happiest when I was traveling—not vacationing, but traveling. Exploring authentically. Moving at my own pace. Meeting locals. Understanding how people actually live in a place. I wanted to make that my life, not just a hobby.

So I created Pivot Trip as a wellness retreat company. In 2018, I led my first retreat in Bali—focused on inner work and transformation through travel. I loved helping people discover themselves. But I also discovered something: the emotional intensity of leading retreats was exhausting. People needed deep healing work, and while that was beautiful, it wasn’t what I wanted to keep building. I wanted adventure. I wanted fun. I wanted to explore the world with people who felt the same way. I wanted to travel like I actually travel.

On that final day in Bali, two gay guys pulled me aside. They said: “Cory, we loved this. You are such an amazing planner, why not just lead small group vacations. Instead of meditation and inner work, can we just do adventure? Culture? Exploration? And keep it exclusively gay men?”

That conversation made me realize something: I wanted the exact same thing. Not wellness retreats. Not party trips. Not cookie-cutter group tours. I wanted small groups of sophisticated, adventurous gay men exploring the world authentically, together. I wanted groups where you could have real conversations over wine in the moonlight at your stunning boutique hotel in Morocco. Where the people you met became actual friends, not just travel acquaintances. Where you could be completely yourself. Exclusively gay men. Maximum 12 people. Off-the-beaten-path. No party circuit. No tourist traps. No BS. I wanted to travel with my people.

So I committed to pivoting Pivot Trip from wellness retreats to small-group cultural immersion travel for gay men. And then the pandemic hit—terrible timing for a travel company, I’ll admit. But during lockdown, I realized this wasn’t just a business pivot. It was something I needed to build. Something I couldn’t not build.

Why Gay Men Only (And Why It Matters)

You might wonder: why exclusively gay and queer men?

It’s not exclusionary. It’s intentional.

When everyone in the group shares a fundamental part of your identity – being a gay or queer man – something shifts. The conversations go deeper faster. You don’t have to explain yourself or worry about judgment. Inside jokes land immediately. There’s an unspoken understanding that comes from shared experience.

Plus—let’s be honest—as gay/queer men, we want to travel to places like Morocco, Egypt, and beyond. But many of us hesitate to travel those places alone. Not because we can’t, but because navigating a destination safely and authentically takes local knowledge and vetted relationships. What I created is different: small groups of gay men traveling with a guide who has deep, trusted relationships in each destination. Our local partners understand the cultural context. They know how to navigate each place thoughtfully. They’ve vetted every restaurant, every guide, every experience to ensure you’re safe and welcomed.

You get to be completely yourself within the group—with 11 other gay/queer men who get it. You’re not traveling alone. You’re not wondering if you belong. You have a community around you and expert local partners who know the landscape. And honestly? The camaraderie that develops on these trips is unlike anything else I’ve seen. Friendships that last years. People who come back trip after trip because they don’t just love the destination—they love these guys and they trust the way I’ve built the experience.

That’s what I wanted to build.

Cory standing on the bowsprit of a sailboat with his arms out

What I Actually Realized (About You)

Since leading my first Pivot Trip, I’ve learned something important about our community: You don’t want to be treated like a tourist. You want authentic cultural experiences. You want to understand why things are the way they are, not just take photos in front of them.

You’re busy—really busy. You don’t have time to spend weeks planning a trip. You want someone you trust to handle all the logistics so you can just show up and explore. You want adventure. Not sitting on a beach all day. You want to hike, kayak, paraglide, cook with locals, challenge yourself. You want to travel with people who “get it”—who share your values. Not a random group of strangers. People you can actually be friends with. You want a single point of contact—not juggling five different emails from five different vendors. You want to know that one person (me) is responsible for making sure everything works.

Whether you’ve traveled to 40 countries or this is your first trip abroad, you know what you want: genuine experiences, not the standard tourist route. You want to explore places that matter to you, with people who care about getting it right.

That’s who I built Pivot Trip for. For anyone who wants to travel this way.

A photo of Cory in an exotic location

What I Bring to Every Trip

I personally lead every single trip. Not because I’m an ego-driven guide, but because: When the boat cancels at midnight in Costa Rica, you don’t email a customer service center. You may never know because I handle it directly and find other solutions. You just continue enjoying your experience knowing it will work out. When a local restaurant is suddenly closed, I know three backup restaurants—because I’ve actually traveled these places, not just googled them. When someone in the group gets sick, there’s one person managing the situation, not you trying to find a solution. When something magical happens—a moment where the group is absolutely present together—I’m there to recognize it and protect it.

My 16 years in business taught me how to organize complexity. My 100+ countries taught me how to navigate anywhere. My experience leading 100+ travelers taught me what actually matters in a trip. But what matters most is this: I care about whether you have the trip of your life. Not in a corporate way. In an actual, personal way. Because I’m the one leading it. I’m the one whose reputation is on the line. I’m the one who will remember you after the trip ends.

That matters.

Pivot Trip guide and owner, Cory with Machu Picchu in the background

What I Believe

If you’re considering a Pivot Trip, you should know what I believe:

Travel isn’t about checking boxes. It’s about perspective shift.
The best travel happens when you slow down, not when you rush.
Food and conversation are the real currency of travel—not Instagram photos.
You deserve to explore the world as your authentic self, not a hidden version of yourself.
You don’t need to be wealthy to travel well. You need to be intentional and willing to do the work to find authentic experiences.
The people you travel with matter more than the destinations. Though both matter enormously.
Adventure and safety aren’t opposites. Smart planning allows you to explore boldly.
You shouldn’t have to limit yourself. You should just travel smart.
Small groups of like-minded people create magic that big tours can never access.

Ready to explore the world differently? Join the Pivot Collective and be the first to hear about our upcoming adventures.

Join The Pivot Collective

100+

COUNTRIES
VISITED

CONTINENTS
EXPLORED

16+

TRIPS LED
(ALL CONTINENTS)

YEARS BUSINESS
LEADERSHIP

Contact Cory