Drake Robertson’s Stories, Lessons & Insights

We recently had the chance to connect with Drake Robertson and have shared our conversation below.

Drake , a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: Are you walking a path—or wandering?
Right now, I feel like I’m truly walking a path. For a long time, I was just wandering — figuring things out, chasing experiences, and honestly just winging it. I’ve always loved a little freedom and spontaneity, so that part of me will never go away. But now, everything I’m doing has direction and purpose.

I’m building something that not only fulfills me creatively, but also gives me space to grow, expand, and connect with others in more meaningful ways. Walking this path feels like alignment — like every project, every recipe, every conversation is leading somewhere bigger.

Can you briefly introduce yourself and share what makes you or your brand unique?
Hi, I’m Chef Hollywood — also known as Chef Drake Robertson — a personal chef, creator, and storyteller who’s been cooking my way through life, one lesson and one recipe at a time.

After more than a decade of traveling the world and cooking aboard luxury cruise ships, I’ve built a brand that blends food, storytelling, and self-growth. My company, Chef Hollywood’s Culinary Creations, started as a personal chef service but has grown into a full creative platform — from my cookbook and podcast, “Cooking Your Way Through Life,” to my YouTube channel where I share real recipes and real conversations about the ups and downs of life in and out of the kitchen.

What makes my work special is that it’s never just about the food — it’s about the meaning behind it. I use cooking as a way to connect with people, tell stories, and explore the idea that every experience — good or bad — teaches us something if we’re willing to taste and learn from it.

Right now, I’m focused on expanding the YouTube show and podcast, filming new episodes that bring together my love for cooking, travel, and honest conversation, while continuing to inspire others to find their own rhythm and flavor in life.

Okay, so here’s a deep one: What’s a moment that really shaped how you see the world?
Working on cruise ships changed everything for me. Growing up in a small town in Monroe, Georgia, my world felt comfortable — but limited. Traveling for the first time made me realize just how big and vast the world truly is. I met people from every culture, tasted foods I’d never heard of, and saw how differently people live, love, and connect.

That experience opened my eyes and changed how I approach life. It reminded me that growth happens when you step outside your comfort zone — and that the world is full of opportunity if you’re willing to explore it.

Was there ever a time you almost gave up?
Yes — in 2020. That year was supposed to be a major turning point for me. I had poured all of my savings into my business, picked up a ton of new clients, and even booked some TV opportunities. Then the world stopped. As a personal chef, I couldn’t work in people’s homes anymore, and everything I’d built felt like it disappeared overnight.

For a moment, I thought it was a sign that maybe cooking wasn’t my path anymore. But instead of giving up, I took that time to reset and rebuild — to think about how I could share my passion in new ways. That’s what led me to start focusing more on content, storytelling, and creating platforms like my podcast and YouTube channel. It reminded me that even when life pauses, your purpose doesn’t.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. Is the public version of you the real you?
Yes — what you see is the real me. One thing working on cruise ships taught me is that you can’t fake who you are for long. When you live and work with the same people for months at a time, any façade will eventually fade. That experience forced me to be authentic — to show up as myself every day.

I think a lot of people see me as an extrovert because I’m always creating, performing, and engaging with others, but deep down I’m actually an introvert. I value quiet moments, reflection, and solitude — they’re what keep me grounded and creative. What people see publicly is real; it’s just the more expressive version of me.

Okay, so let’s keep going with one more question that means a lot to us: What are you doing today that won’t pay off for 7–10 years?
Right now, I’m investing in my future — both creatively and financially. Everything I’m building through my YouTube channel, podcast, and cookbook is part of a bigger picture. I’m not just creating content; I’m building a legacy.

I’m also thinking about generational wealth, because my family doesn’t have that foundation yet. I want to be the one who changes that story. The hard work I’m putting in now — building my platforms, investing, and creating sustainable income streams — is for my future and the generations after me. It’s about planting seeds now so that years from today, I can look back and see how those efforts paid off.

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