We recently had the chance to connect with Clifford “Oujeroo” Williams and have shared our conversation below.
Good morning Clifford “Oujeroo”, it’s such a great way to kick off the day – I think our readers will love hearing your stories, experiences and about how you think about life and work. Let’s jump right in? What is a normal day like for you right now?
A normal day for me right now starts around 10 a.m. I’m up with my twins, making sure they’re good, and then I jump straight into work mode. From 10 to about 4 is my main block of focus, and in that time I’m wearing a lot of hats. I’m running Let’s Gravel, working with developers, refining our payment flows, and making sure everything lines up for the accelerator and investor conversations. At the same time, I’m planning trips for Black World Travelers—locking in hotels, refining itineraries, and negotiating rates for Costa Rica, Ghana, Thailand, Zanzibar, and more. I also support my Wife Amber with Rest Roam Reset—helping her shape branding, itineraries, and VIP experiences—and keep Aspera Group moving, whether it’s coffee and cacao exports from Haiti or real estate projects in Miami.
My day is a mix of strategy and execution. One moment I’m building out a pitch deck, the next I’m reviewing hotel options or going over coffee packaging details. It’s nonstop, but I thrive in it.
Once I wrap up around 4, I shift into dad mode again. The twins keep me on my toes—right now we’re deep in potty training—so a lot of energy goes into parenting, structure, and making sure the house runs smooth.
Evenings are family time with Amber and the kids, but I usually circle back into my work once the house is quiet. Sometimes it’s creative bursts—branding, itineraries, or pitch prep. Other times it’s big-picture thinking: where Let’s Gravel is headed, how to grow BWT, or how to balance all of this with family life.
Every day is a lot, but it’s purposeful. I’m building businesses, creating experiences, and being present for my family all at the same time.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Clifford “Oujeroo” Williams, and I’m an entrepreneur who builds experiences that connect people through travel, culture, and business. I’m the founder of Let’s Gravel, a group travel platform designed to take the stress out of planning trips, collecting payments, and making sure everyone actually shows up. I also lead Black World Travelers, where we curate global experiences for people who want more than just a vacation—they want culture, connection, and unforgettable memories. Alongside that, I run Aspera Group, which focuses on real estate projects and exporting Haitian coffee and cacao to the world.
What makes my work unique is that it all comes from lived experience. I’ve seen how hard it is to organize group travel and how many opportunities are lost when systems don’t exist to support people who want to see the world. That’s why I built Let’s Gravel. I’ve also seen how powerful it is when travel shifts people’s perspective—whether it’s exploring Ghana, Costa Rica, Thailand, or experiencing Haiti beyond the headlines.
Right now, I’m focused on scaling Let’s Gravel into the go-to tool for group travel organizers, expanding Black World Travelers’ reach, and continuing to grow Aspera Group’s footprint. At the heart of everything I do is one belief: travel is more than moving from place to place—it’s about transformation, community, and creating stories that last a lifetime.
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. Who taught you the most about work?
The people who taught me the most about work are my grandmother, my grandfather, and my mom. Growing up in Haiti, I watched my grandparents run multiple businesses, and that gave me an early example of what it means to hustle, to create, and to provide. Then when we moved to the States, I saw my mom start over from scratch and build something new for us. Those experiences shaped me—seeing resilience, entrepreneurship, and determination up close. They taught me that no matter the circumstance, you can create opportunities if you’re willing to put in the work.
What did suffering teach you that success never could?
Suffering taught me something success never could—gratitude. When you’ve been through hard seasons, you learn how to appreciate even the smallest things in life. Success feels good, but it can sometimes make you focus on the big wins. Suffering slows you down and makes you notice the details—the moments, the people, the little breakthroughs you might otherwise overlook. It taught me to be grounded, to stay thankful, and to never take anything for granted.
Next, maybe we can discuss some of your foundational philosophies and views? What would your closest friends say really matters to you?
My closest friends would say what really matters to me is family, legacy, and impact. They know I care deeply about creating opportunities—not just for myself, but for the people around me. They’d tell you I’m serious about building businesses that last, but at the same time, I never lose sight of making sure my family is good and that I’m showing up for them. They’d also say I value experiences, connection, and helping people see the world differently. At the end of the day, it’s not just about success—it’s about leaving something meaningful behind.
Okay, so let’s keep going with one more question that means a lot to us: What do you understand deeply that most people don’t?
What I understand deeply that most people don’t is that opportunity is everywhere—but it doesn’t always look like opportunity at first. Growing up, I watched my grandparents and my mom build from very little, so I learned early that resources don’t create success—resourcefulness does. Most people wait for the “perfect moment” or the “right conditions.” I’ve learned that if you move with what you have, keep your vision clear, and stay consistent, you can create something out of almost nothing. That perspective shifts how I approach business, travel, and even life—it’s about seeing possibility where others see limits.
Contact Info:
- Website: https://www.letsgravel.com
- Instagram: Oujeroo
