Meet Oliver Roldan of Status Boulevard

Today we’d like to introduce you to Oliver Roldan.

Hi Oliver, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
On the outside I might look like a success story, but the truth is everything I’ve built was born from loss, survival, and a relentless will to keep going when it felt like the world was collapsing.

My father was my hero. In the early 2000s he built a home health business from nothing. But when the economy crashed, so did his company. And over time, so did his health. I watched the man I admired most pour every ounce of himself into a sinking ship while trying to stay present for four kids. He worked late nights, weekends, holidays. He gave up everything for us. And in 2013, he passed away. Not from illness alone, but from years of silent sacrifice that eventually caught up to him.

We didn’t inherit wealth. But my dad left me something far more valuable: Blueprints for grit. The quiet strength to keep going. And the stubborn belief that from nothing, you can build something.

After he died, I moved in with my girlfriend (now wife). We were starting from rock bottom. I bartended to pay the bills while she was in school. We were so broke that I skipped meals. I used to dig through the apartment dumpsters for fast food coupons just to get through the month. I’d eat at work and bring home leftovers for us to share. When the apartment next door got infested with roaches, we didn’t have the money to move. So we stayed. We endured.

In 2017 after 16 years together, I finally proposed. I was working two bartending jobs for 80 hours a week, sleeping in my car between shifts to save for a wedding. I missed birthdays. Baby showers. Moments I can’t get back. All so we could inch forward.

Then came 2020.

The pandemic hit like a wrecking ball. I lost both jobs. We lost seven family members. Everything we had left slipped through our fingers. No income. No safety net. No light.

So I delivered groceries. Not for the money, it barely paid. But because standing still felt like giving up.

That’s when our family friends Jameson and Abby Wang sat me down and asked if I had ever thought about going back to school. I was initially closed to the idea. I was in my mid 30s competing with Ivy League and pre-med graduates. Months earlier I was behind a bar asking if customers wanted salt or no salt on their margarita. Now I was going to enroll in Codesmith, the most elite coding programs in the country. The Wangs were gracious enough to front the deposit and off I went, back to the classroom.

I was the worst in the entire cohort. I couldn’t keep up. I forgot how to learn and organize my thoughts in a structured way. The stress wrecked me physically to the point where I ended up in urgent care and missed two days of class.

But I didn’t quit.

I showed up early. I stayed late. I asked questions that made me feel dumb. Then somehow just before graduation, I was chosen to lead and teach future cohorts the same curriculum I once struggled to understand just a month prior. Two weeks after that fellowship ended, I landed a software engineering job at a Fortune 500 company. That job didn’t just change our finances. It helped heal a decade of emotional wounds I didn’t even know I was still carrying.

Once life gave us a sliver of breathing room, I chased a passion I’ve always had: Timepieces.

I looked up to Ben Baller, Johnny Dang, and Pejman Ghadimi as industry leaders who made the barrier to entry not so insurmountable. In 2023 I bought my first Tag Heuer for $960, scared out of my mind. “What if it’s fake?” “What if I got scammed?” “What if I bought a stolen watch?” But I stayed curious. Took courses. Found local mentors. That $960 watch turned into buying, selling, and trading $20k – $100k timepieces in under two years. What once started as a simple flip quickly became a business I now love.

But no matter how far I go, I will NEVER…EVER…forget where I started. With a father who gave his life for his family. A wife who never once stopped believing in me. And a younger version of myself who refused to give up when life gave him every reason to.

I’m not self-made. I’m community-made. I’m built on sacrifice, legacy, and love.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Was it smooth? LOL Not even close.

I swear it felt like I hit every trap, stumbled into every dead-end, and faceplanted into every mistake possible. I like to say I “mistaked” my way to success because that’s exactly how it felt. Do I miss it? Would I go back? Man hell no absolutely not! I don’t want to go back ever again. BUT….

…If I had to sum it up I’d say it like this: If life treated me like a grape – crushing me emotionally, physically, and financially, then somehow all those years of pressure ended up producing the finest wine. Cheesy? Yeah maybe. Is it true? Every drop of it.

As you know, we’re big fans of Status Boulevard. For our readers who might not be as familiar what can you tell them about the brand?
At Status Boulevard, I specialize in buying, selling, trading, and consigning modern high-end luxury timepieces from Omega, Panerai, and Cartier to Rolex, Audemars Piguet, Patek Philippe, and Richard Mille. At its core, this business is about more than just watches. It’s about people, stories, and milestones.

A timepiece is rarely just a watch. It’s often a symbol of a promotion, a dream realized, a memory, or a hard-earned win. What sets me apart is the care I take in understanding why a watch matters to someone. Whether you’re a first-time buyer or a seasoned collector, I make sure you’re truly heard. I don’t just ask what you’re looking for, I ask what it means to you. I believe great customer service isn’t just about the sale. It’s about how someone feels throughout the process and long after.

I started this business to break the mold. Yes I’m completely aware, the name Status Boulevard has some edge to it. Although it’s not about flexing wealth or chasing status for the sake of status. To me it’s about owning your journey. It’s about reminding people that success has many forms, and no matter where you start, you’re never stuck. You CAN level up. You CAN rewrite your story. That message is deeply personal to me…because I’ve lived it.

Though I’m based in Los Angeles, I serve clients across the country and internationally. Whether it’s helping you track down a grail piece, evaluating your current collection, or walking you through your first luxury purchase, I’m in it with you from start to finish. Once we do business together you’re not just a client – I’m the guy who checks in months later to make sure you’re still loving your piece, sends you surprise merch, and becomes your go-to watch plug, consultant, and if needed… unofficial life coach.

At the end of the day, I just want people to feel empowered, understood, and proud of what they wear because it should represent something real. Something you earned. And if I can play a small role in that story? That’s what makes it all worth it.

Any big plans?
Right now I do everything with my own two hands and the same 24 hours we all get, but I know the vision is bigger than me. My goal is to expand beyond just what I can personally touch. I’m working toward building a team: people who believe in the mission, who can help me scale operations, grow the brand, connect with more people, and yes, to create the best watch memes in the game.

I hope to open a physical storefront down the road…not just to showcase beautiful timepieces, but to create a space where people feel inspired to dream bigger, believe in themselves, and maybe see a little of their own story in mine. It’ll be more than a watch shop: it’ll be a hub for growth, culture, and community.

There’s a long road ahead, but I’m excited for every step. I’ve come too far to stop now, and I truly believe the best is still to come.

Contact Info:

• Website: https://www.statusboulevard.com
• Instagram: https://www.instagram.com/statusboulevard/
• Facebook: https://www.facebook.com/people/Status-Boulevard/61573197568362/
• Twitter: email: [email protected]
• Youtube: Text: (310) 776-9530
• Other: https://maps.app.goo.gl/wkanFZkVAA58C5A9A

Image Credits
Brian Encarnacion Instagram @encarnation
Erwin Encarnacion Website: photoswitherwin.com