Charting New Courses: A Chat with Leyla Osorio, CEO and Co-founder of Global Cruises
As the head of a leading shore excursion company, Leyla’s days are packed with meetings, strategic planning, and collaborating with teams worldwide to ensure passengers have unforgettable experiences. But it's not all work—Leyla treasures her evenings spent with family, balancing her professional achievements with personal joy. In our relaxed chat, she shares the highs, challenges, and motivations that drive her in both life and business.
What's a typical day in your life look like?:
I'm an early bird, no doubt about it! My day kicks off at 4:45 AM sharp. I carve out about 90 minutes for exercise, meditation, and reflection, setting a positive vibe for what's to come. As CEO of Global Cruises, my schedule is always on the move. I start by touching base with teams, and diving into priorities and challenges, which can shift with the seasons. Throughout the year, we're collaborating with teams worldwide to deliver top-notch shore excursion experiences and services. Steering a team like this keeps me on my toes, constantly engaged in driving success for the company while also nurturing my personal growth. Evenings are all about family time and unwinding together after a productive day.
What is the most rewarding part of your work?:
The most rewarding part of my work is seeing experiences come to life and passengers creating lasting memories. There's nothing quite like witnessing the excitement on passengers' faces as they embark on their journey and engage in the activities we have curated for them. Knowing that our efforts contribute to these moments of joy and connection is incredibly fulfilling. It's what drives me and our team to continue striving for excellence every day.
What would you say has been your biggest obstacle in launching a successful career? How have you overcome it?:
Transitioning between industries was no easy feat. It felt like diving into the deep end without knowing how to swim. Starting from scratch in the tourism sector? Yeah, that was a whole new ball game. But hey, I'm not one to back down from a challenge. I rolled up my sleeves, put in the hours, and slowly but surely, things started to click. Learning the ropes, and understanding the ins and outs—it was quite the strenuous but rewarding journey, especially in such a solidified industry. But every stumble, every setback, it all just fueled my determination to make it work. This journey taught me the value of embracing change for personal and professional growth, showing me that taking risks can lead to great rewards.
What is the phrase, sentence, or conversation that stopped you in your tracks and changed your outlook in life?:
A conversation with my sister, Maria, was one of the inspirations behind starting Global Cruises. She asked me a simple question: "Leyla, how do you do it? You’re going to miss half of your kids’ lives." Those words hit me like a ton of bricks. It made me realize that my previous job, which required me to travel four out of seven days a week abroad, was taking me away from the moments that truly mattered—time with my family. It was one of the sparks that prompted me to make a change and create Global Cruises, not only as a career move but also as a way to be present with my family in the same city. While I do spend lots of time working on Global Cruises, being able to share those pockets of time with my children and husband in the same city means the world to me.
If you had the choice to go back to your past or fast forward to your future, which one would you choose? Why?:
If given the choice, I would fast forward to the future. Why? Well, I'd love to see if there's a pivotal moment in my future where I could make a difference for my children as they grow older. Being able to glimpse ahead and identify those critical moments where my guidance could shape their paths would be invaluable. It's all about ensuring I'm there for them where it matters most, you know? So yeah, bring on the future—I'm ready to see what it holds.
If you were to meet 10 year old you, what would you say to them?:
If I could meet my 10-year-old self, I'd say, "Hey there, Leyla. Listen up. No matter what life throws your way, never give up. Keep pushing forward, keep trying your best, because let me tell you something—you're going to make it. Trust me on this one. So keep that chin up and keep on going. You've got this."
When are you the happiest?:
I'm happiest when I'm with my family. There's just something about being surrounded by the people I love, sharing moments, laughing together, and creating memories. It's in those simple, everyday moments—whether we're cooking dinner, traveling, or just enjoying each other's company—that I feel truly content and fulfilled. Family truly is where the heart is, and it's where I find my greatest happiness.
What is stopping you?:
What's stopping me? Honestly, it's the perpetual struggle with time. There's always so much I want to do, so many places to go, and so many dreams to chase. So yeah, if I could have more time—just a little bit more—I know I could accomplish even more, see even more, experience even more. But hey, I guess that's just life! We do the best we can with the time we've got.
Hustle culture and burnout is so prominent in our community. How do you prioritize self care?:
Given the prominence of hustle culture and the risk of burnout in our community, prioritizing self-care is essential. For me, it starts with setting clear priorities and boundaries. I make a conscious effort to prioritize activities that promote well-being, such as meditation, regular exercise, and expressing gratitude. By carving out time for these practices, I recharge my batteries and maintain balance in my life.
What accomplishment are you most proud of, both in your personal and professional life?:
In my personal life, I'm most proud of my family. They're my rock, my support system, and my greatest source of joy. Watching my children grow and thrive, and nurturing strong, loving relationships with my spouse and loved ones, brings me immense pride and fulfillment. Professionally, my greatest accomplishment is building Global Cruises with our wonderful team. It's been a journey filled with challenges, risks, and rewards. Seeing the company grow and flourish, providing unforgettable experiences for countless travelers, is a testament to hard work, determination, and vision. I'm proud of what we've achieved.
Drink 🫖
What is Leyla’s go-to drink?
That’s so interesting, and I wonder what my coffee order reveals. My go to is a Cappuccino with skim milk. Simple, but reliable.
Listening To 🎧
What is Leyla listening to at the moment?
Ah, lately I've been diving into a variety of audio content. One thing that's really been feeding my mind is a Mark Cuban masterclass I recently listened to on winning big in business. It was packed with insightful nuggets that got me thinking. In the mornings, I start my day with meditation, and I've been exploring different sessions offered by Peloton. They've got a great selection that really helps set a positive tone for the day. Now, when it comes to music, that's my go-to for inspiration. Every morning, I kick off with some spiritual tunes that really uplift my spirits and get me in the right mindset. And I've been delving into James Clear's work lately too; his insights on habit formation and personal development have been quite influential for me. So, it's been a mix of learning, meditation, and music that's been shaping my mindset lately.
Your Truth 🗣️
What is a Leyla’s truth?
I've always been driven by the desire to break barriers and push boundaries. I thrive on leading teams and fostering environments where innovation and creativity can flourish. I believe in transcending limits, not just confining ourselves to one destination or concept but spreading our wings to multiple destinations, collaborating with local talents, and showcasing the unique beauty each destination has to offer.
What inspires me the most is the world itself. Every sight, every destination holds its own charm, its own story waiting to be discovered. Traveling opens my eyes to the diversity of cultures, landscapes, and experiences. And it's a constant reminder of the beauty and wonder that exists in our world.
As for where I'm headed, it's a journey of consolidation. Professionally, I'm focused on consolidating the footprint of our Shore Excursion company, Global Cruises, and expanding our reach while maintaining the integrity and creativity that drives us. And on a personal level, I'm in a phase of consolidating my family life. After fifteen years of marriage, my aim is to nurture and strengthen the bonds of love, family, and shared values. So, in essence, I see myself moving forward by solidifying what I've built, both in business and in life.
Your Plug 🔌
What is Layla plugging today?
Our latest endeavor with Global Cruises is truly something special. We're incredibly proud to announce our expansion into Canada and New England, marking a significant milestone in our journey. It's been a journey filled with challenges and doubts, but as we clear those hurdles and build something that will stand the test of time, the excitement only grows.
From the breathtaking destinations we'll visit to the communities nestled within them, and even the cruise lines themselves, our goal is to be a catalyst for showcasing the beauty and charm of these locales.
More about Leyla Osorio
Leyla Osorio is the CEO and co-founder of Global Cruises, one of the world’s most innovative shore excursion companies. As a strategic visionary of the company, Leyla manages and directs her team to develop and execute upon goals and objectives while assessing different scale-based opportunities to propel the company’s growth.
Over the course of the last 15 years under Leyla’s leadership, the company has grown and is now present in 100 ports around the world, serving more than half a million passengers per year. She earned her bachelor’s and master’s degrees in political science from La Universidad de Los Andes in Colombia. She went on to earn her MBA from Northwestern University, Kellogg School of Management. Leyla currently resides in Miami with her husband and three children. Her favorite travel destination is Cape Town, known for its scenery, a varying landscape found in very few other places at the same time.