Meet Jay Chevery

We had the good fortune of connecting with Jay Chevery and we’ve shared our conversation below.

Hi Jay, what is the most important factor behind your success?
The most important factor behind my success has undoubtedly been my ability to build and leverage a strategic network. Let me share a bit of my story. I didn’t grow up with a family that had connections in the industries I’ve thrived in, nor did I have the financial backing to lean on. There were even times when I was far from home, working in cities or countries where I didn’t know anyone. But I didn’t see those circumstances as obstacles—I saw them as opportunities to sharpen my skills in connecting with people.

Networking became my superpower. I learned that relationships are the foundation of any achievement. I built what I like to call a “spider web” of contacts, ensuring that the right people knew about my skills, services, or vision. Each connection became a thread that linked me closer to the people and opportunities I needed to grow my career or bring a project to life.

Networking isn’t just about asking for help; it’s about offering value and building trust. The more I expanded my web with intention—focusing on people who aligned with my goals—the clearer my path became. I wasn’t just growing a network for the sake of it; I was creating a system that supported my aspirations and aligned with my values.

For anyone looking to scale their business or achieve their goals, I can’t stress enough the importance of strategic networking. It’s not just about who you know—it’s about who knows you and what you stand for. By creating genuine, purposeful connections and ensuring your name is in the right conversations, you can open doors you didn’t even know existed. So, go out there, weave your web, and let it carry you to new heights.

Alright, so let’s move onto what keeps you busy professionally?
One of the most defining moments in my life was moving to a new country, to Miami, Florida and building an entirely new career from scratch. It wasn’t just a career transition; I was also navigating the complexities of government policies, supporting my pregnant wife, and then welcoming a newborn into our lives. Balancing all of that while striving to establish myself professionally was a monumental challenge.

But here’s the thing: passion and purpose don’t let you quit. Despite everything, I was able to carve out a path and secure a highly coveted role at one of the world’s most iconic five-star hotels, Faena Hotel Miami Beach. This achievement wasn’t just a milestone; it was proof that with persistence and strategic focus, you can rise to meet even the most overwhelming challenges.

What sets me apart is that I use these real-life experiences to connect with others. I have lived through the struggles of reinvention, the weight of responsibility, and the drive to succeed against all odds. Along the way, I’ve learned that success isn’t about perfection, it’s about perseverance, adaptability, and staying anchored to your passion.

Through all of this, I’ve developed a framework 25 steps that align with what I’ve observed in successful individuals. These steps revolve around becoming the person who naturally attracts the life you want. Using art, sports, and human behavior analogies, I break down these concepts into actionable insights that anyone can apply to their life.

What I want the world to know is this: no matter where you start, no matter how many obstacles you face, transformation is possible. My journey, from my early struggles to being named one of the top entertainers in the country, to rebuilding my career in a new country, to thriving in a high-profile role is living proof. You have the power to rise, to rebuild, and to create a life that reflects your deepest passions and values.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
If my best friend were visiting Miami for a week, I’d make sure they had an unforgettable time exploring the best of what this vibrant city has to offer. And, of course, the first stop would be the iconic Faena Hotel Miami Beach, a place that truly captures the magic of Miami.

We’d start with a dining experience at Pao by Chef Paul Qui, where the fusion of Filipino, Spanish, Japanese & French flavors make every meal unforgettable. After dinner, we’d head to The Living Room, a must-visit for its stylish ambiance, handcrafted cocktails, and nightly live band performances. For the weekend, nothing beats the energy of The Saxony Bar, where the exclusive vibe and curated music create a nightlife experience like no other. If we’re in the mood for a show, we’d check out what’s happening at Faena Theater, which always offers acclaimed performances. And if we’re lucky enough to catch Rocky Lane performing at one of these outlets, it’s an absolute must—she’s one of Miami’s most incredible entertainers.

Outside of Faena, there are plenty of other spots that I’d take them to. Medium Cool is one of my go-to bars for its welcoming staff, amazing ambiance, and consistently great music. It’s a perfect late-night spot to unwind. For breathtaking views, we’d head to Rosa Sky—it’s my favorite rooftop bar, where Emma and her team always make sure you have the best experience.

For daytime activities, nothing beats a walk along Miami Beach’s boardwalk, soaking up the sun and ocean breeze. We’d also venture beyond the beach to explore neighborhoods like Brickell and Coral Gables, which offer a mix of great restaurants, bars, and local charm. Miami Shores, where I live, is another hidden gem with a strong community feel, cozy cafes, and beautiful parks to relax in. And, of course, a trip to Miami isn’t complete without visiting the vibrant, artsy streets of Wynwood, where the murals, galleries, and unique energy make it a must-see destination.

From world-class dining and entertainment to breathtaking views and local gems, Miami has so much to offer, and I’d make sure my best friend experienced it all. Every moment would be filled with fun, flavor, and unforgettable memories!

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
Thank you for this wonderful question! It’s such a great reminder that success is never achieved alone—it’s always a culmination of the support, guidance, and inspiration we receive along the way. For me, there are two incredible people who deserve a huge shoutout, and I’ve even shared their stories in my self-development book, The Rise of The Jaytleman.

The first person is Stéphane Pauzé, my creative and artistic school teacher from Fernand-Gauthier School in Montreal. I was just 11 years old when he organized an artistic talent show where we recreated a musical awards ceremony. It was there that I stepped onto the stage for the first time, performing a juggling act and impersonating Will Smith as a 2nd act. That experience sparked something inside me—it was the moment the entertainer in me was born. Stéphane’s encouragement and vision showed me that art and creativity could be powerful outlets for self-expression, and that moment became the foundation of my entire career.

The second person I owe so much to is my friend François Fleurent. As a teenager, François asked me a question that literally changed my life. It was a late night in a park in Montreal-North. François and his best friend were DJs, hosting house and school parties. Seeing my passion for music and my entrepreneurial spirit, he asked if I wanted to join their crew. He promised they would teach me how to DJ if I helped them grow their business. That was my beginning—a DJ career that soon evolved into hosting and beyond. Together, under the name AZONE, we created something special. For years, we made a name for ourselves in Montreal nightlife, and that momentum launched me into the next stages of my career.

Both of these moments—Stéphane’s talent show and François’s late-night question—were pivotal in shaping who I am today. They remind me of the importance of community, mentorship, and how the belief of others can ignite our own potential. So to Stéphane and François, and to all the mentors, friends, and collaborators who’ve been part of my journey, I say thank you. You’ve been instrumental in my rise, and I’m forever grateful.

Website: www.jaychevery.com

Instagram: www.instagram.com/thejaytleman

Linkedin: https://www.linkedin.com/in/jaychevery

Youtube: www.youtube.com/@thejaytlemanshow

Image Credits
Maxim Huard, Esteban Cortazar