Alright – so today we’ve got the honor of introducing you to Gilleon Smith. We think you’ll enjoy our conversation, we’ve shared it below.

Gilleon, thanks for joining us, excited to have you contributing your stories and insights. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.

I’d get painfully clear on what I actually do and who I do it for, and I’d build my brand narrative around that instead of trying to be everything to everyone. Clarity over complexity—every time. I’d also invest in hiring a coach early on. Someone who could challenge my blind spots, help me focus, and hold me accountable to moving with purpose instead of panic. That kind of guidance would’ve saved me years of trial and error.

Then, I’d stop trying to “DIY” my way through everything. That doesn’t make you scrappy—it makes you exhausted. I’d immediately invest in a few solid systems: a streamlined CRM, branded email marketing, and a beautifully designed Showit site (obviously) that wasn’t just pretty, but positioned to convert.

And I would’ve leveraged social media as the business tool it is, rather than treating it like a place to post up out of boredom or obligation. Once I understood it as a visibility engine, relationship builder, and sales channel—not just a feed—I moved completely differently. I showed up with strategy and purpose, not just for vanity metrics.

Lastly, I’d surround myself with community sooner. Not just internet friends or peers, but people I could be honest with about fear, money, and momentum. Building something beautiful doesn’t have to feel like a secret solo mission.

So yeah—more clarity, better systems, early mentorship, and treating platforms like the marketing departments they are. If I had all that dialed in from day one? I’d still hustle—but I’d be doing it a whole lot smarter.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m the founder of GASM Brands, a business strategy and web design consultancy helping bold entrepreneurs turn their message into magnetic brands that actually move. I combine clarity, storytelling, and clean, elevated design to build brands that aren’t just pretty—they’re profitable.

I started my career in New York as a casting director, running my own agency and collaborating with major brands and creative teams. When I moved to Los Angeles, it was to work in celebrity representation—developing brands for talent during one of my only real 9-to-5 jobs ever. But it was the middle of the pandemic, the industry was chaotic, and to be honest, I was burnt out doing the heavy lifting for other people’s legacies.

And then—life flipped. After years of being told I might not be able to have children and over a decade of marriage, I got pregnant unexpectedly. It was a miracle moment that forced me to reflect deeply on my future, my values, and my time. I knew I needed ownership. Not just over my schedule, but over my impact.

I realized that if I could build visibility, presence, and profitability for big names, I could absolutely do it for other entrepreneurs—especially those navigating big transitions, big ideas, or big energy with no clear brand direction. So I taught myself digital systems, studied user experience, learned platforms like Showit, and built the agency I wished existed for me.

Now, I offer everything from full-service brand identity and website builds to strategic consulting, sales page creation, and content design. My clients are wellness pros, service providers, beauty founders, speakers, creatives, and women rewriting their narratives. I help them articulate who they are, package it with style and strategy, and build businesses that feel like home.

What sets me apart is that I lead with both clarity and care. I don’t just give you visuals—I give you a story, a system, and a strategy that can scale. I build brands that you’ll actually want to show up for.

I’m proud of the depth, the intention, and the transformation I bring to the table—and the fact that I built this while building a family and healing parts of myself I didn’t know were broken.

If you’re wanting to create a brand that matches your growth, your gifts, and your next level—I’d be honored to help you build it.

Can you talk to us about your experience with buying businesses?

Yes, technically I have bought a business—though the way it happened was a little less “boardroom acquisition” and a lot more “right place, right time, right grind.”

The first casting agency I ever worked for was owned by a friend and mentor. I had been managing the day-to-day for years, and when she was preparing to have her second child—and deep in the trenches of motherhood—she offered me the opportunity to take it over.

At the time, I had zero financial safety net. I scraped together my life savings, borrowed money from my then-boyfriend (now husband of 13+ years), and acquired the business. It was generating okay revenue at the time (this was back in 2010), and I saw the potential to build something bigger.

I restructured the operations, elevated the brand, streamlined client experience, and began scaling strategically. I eventually turned that business into a multi–six figure agency and used it as a launchpad to create a second casting company focused on high fashion runway and commercial talent—also scaling that to six-figures.

The acquisition was rooted in hustle, vision, and respect. That experience taught me what it means to take ownership—of a brand, of a reputation, and of an opportunity. It also showed me that you don’t need investors or a trust fund to build something meaningful—you need clarity, resilience, and the willingness to make bold moves before you feel ready.

That moment was the beginning of stepping into being a boss—and the foundation for everything I do in business now.

Conversations about M&A are often focused on multibillion dollar transactions – but M&A can be an important part of a small or medium business owner’s journey. We’d love to hear about your experience with selling businesses.

Yes, I sold my casting agency—but it wasn’t just a business decision. It was a personal evolution.

I had built two successful multi–six figure casting companies in NYC—one focused on extras commercial work, the other in high fashion runway—and while I was proud of what I’d accomplished, I was growing increasingly frustrated with the industry. It was traditional, political, and often petty. I was doing high-level work but still felt boxed in, undervalued, and constantly navigating gatekeeping energy that no longer aligned with who I was becoming.

One day, I casually mentioned my desire to sell in a shared office space—and it just so happened someone powerful was within earshot. Right place, right time, right hustle. He was experienced in business sales and offered to help me understand what it would take to actually exit. He introduced me to a broker and helped me start crunching the numbers. That was the first time I realized that I’d built something valuable enough to be acquired.

It didn’t happen overnight—it took a few years of positioning, negotiating, and truthfully, soul-searching. When the right offer finally came from the right company, I was ready. The process was grueling. Incredibly intrusive, emotionally intense, and at times deeply uncomfortable. But it also gave me a crash course in maturity, self-worth, and long-term vision.

The biggest lesson? Don’t just build a business that makes money. Build a business that holds value—with or without you.
That means:

Strong positioning
Documented systems
Professional relationships that outlast personality
And the courage to see yourself not just as a founder, but as a CEO
Selling that business expanded everything for me—my confidence, my capacity, and my understanding of what’s possible when you move with both strategy and self-respect.

It gave me the runway to launch my next chapter on my own terms. And now I help others do the same.

Contact Info:

• Website: https://ilovegasm.com/
• Instagram: https://www.instagram.com/gilleonsmith/
• Facebook: https://www.facebook.com/gilleonsmith
• Linkedin: https://www.linkedin.com/in/gilleon-smith-mercado-9197b063/

Image Credits

https://www.instagram.com/therealluthercherry/