We were lucky to catch up with Skylar Raye recently and have shared our conversation below.

Skylar , looking forward to hearing all of your stories today. Before we get into specifics, let’s talk about success more generally. What do you think it takes to be successful?

Growing up, my father drilled one word into my head: tenacity. As a serial entrepreneur, he built multiple successful businesses that still exist today. I never once saw him complain about staying late to fix machinery or being the first and last person at the office. He understood that success wasn’t about convenience—it was about perseverance.

To be successful, and especially to be a business owner, it takes tenacity. Choosing to be an entrepreneur means choosing the harder path. It means taking full responsibility for both your successes and failures. How hard you work, how resilient you are, and how much you push yourself forward is entirely up to you. There’s no roadmap, no boss holding you accountable—you have to be your own biggest motivator.

When I started my business about a year ago, I finally understood what my father meant by tenacity. Entrepreneurship isn’t just about having a great idea; it’s about the willingness to fail and not quit. It’s about choosing to keep going, even when things get tough. It’s about fully believing in the vision you’re striving to achieve and putting in the work, day after day, to make it a reality.

In my journey of building a digital marketing business, I’ve learned that success is built through failures—each mistake teaches you the right way to do things. Failures make you learn tenacity and give you experience. But just as important as tenacity is staying true to who you are. I believe one of the biggest reasons for my success is how deeply I care about each and every client we work with. We don’t just manage their social media or take their content; we become a part of their business, helping them shine in the digital world. We are strategists, but we’re also motivators—empowering other businesses to grow and thrive. True success isn’t just about what you achieve for yourself; it’s about lifting others up along the way.

So to be successful, it takes tenacity, true passion for your work, and a commitment to helping others succeed.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Skylar Raye, the founder of CS Digital Marketing & Media, a full-service agency specializing in social media management, branding, photography, and videography. Originally from Kansas City, I now live and operate my business out of Naples, FL, where I work with businesses to elevate their online presence and tell their story through digital media.

I originally went to school for business management and marketing, but I didn’t always know I wanted to pursue digital marketing. What I did know was that I had a deep love for photography, design, and social media. Growing up, I enjoyed managing my family’s business social media pages, taking on small design projects, and even drawing logos just for fun. I was always fascinated by branding and the way businesses visually communicate their identity.

What We Do & What Sets Us Apart

When I moved to Naples, I started working with real estate agents, capturing content and managing small social media accounts. That experience was a turning point—I realized just how much I loved helping businesses build their brand, create content, and connect with their audience online. From there, I decided to further my education in digital marketing, branding, and content strategy, and within a few months, CS Digital Marketing & Media was born.

At CS Digital Marketing & Media, we do more than just manage social media accounts—we help businesses stand out, grow, and thrive online. What sets us apart is our hands-on, personalized approach. We become an extension of your brand, working closely with our clients to ensure their vision is executed at the highest level. Unlike agencies that take a one-size-fits-all approach, we strategize, create, and adapt based on your specific business goals.

What I’m Most Proud Of

More than anything, I’m proud of the relationships we’ve built and the businesses we’ve helped grow. We don’t just provide services—we truly invest in our clients’ success. Seeing a brand come to life, a business flourish, or a client feel more confident in their digital presence is what drives me every day.

At CS Digital Marketing & Media, our focus is YOU. We believe that every business has a story worth sharing, and our mission is to empower you to shine online. The name CS stands for Chasing Skys, which reflects our philosophy—helping you dream bigger, reach higher, and achieve limitless success in the digital world.

Can you talk to us about how your side-hustle turned into something more.

Key Milestones in Scaling My Business

Realizing My Passion: The turning point came when I recognized that I wasn’t just managing social media—I was helping brands grow, tell their story, and establish a strong digital presence. This wasn’t just a job for me—it was something I truly loved.

Investing in My Education & Skills: Once I knew this was the direction I wanted to take, I immersed myself in learning—I studied branding, digital marketing, photography, videography, and strategy. I knew if I was going to turn this into a real business, I needed to offer top-tier expertise and further my education from the best.

Learning to Delegate & Build a Team: One of the biggest lessons I had to learn came from my dear friend, Faith Schwalback, who told me, “If someone else can do what you’re doing in your business, you shouldn’t be doing it.” That advice completely changed my mindset. As my client base grew, I had to loosen the reins and delegate tasks—I couldn’t do it all alone. Hiring a team meant trusting others to help manage the workload so I could focus on scaling and leading the business.

Taking the Leap & Going Full-Time: As my business expanded, I reached a point where I had to decide—was this just a side hustle, or was I going to fully commit? Taking that leap was terrifying but exhilarating. I officially launched CS Digital Marketing & Media, built a team, and refined our services to offer social media management, branding, photography, and videography.

Building a Brand, Not Just a Business: I knew I didn’t just want to be another marketing agency—I wanted CS Digital Marketing & Media to be a brand that truly empowers businesses. That’s why we operate with a hands-on, relationship-driven approach, working closely with our clients to help them chase skys and reach their full potential online.

What This Journey Has Taught Me

Turning my side hustle into my full-time career has been one of the most challenging yet rewarding experiences of my life. It has taught me resilience, the power of consistency, and the importance of truly believing in your vision.

For anyone looking to take their side hustle full-time, my advice is simple: be tenacious, invest in your growth, and never stop chasing bigger opportunities. And most importantly, don’t be afraid to delegate—you don’t have to do it all alone.

How do you keep your team’s morale high?

The best leadership advice I can give is simple: treat others how you want to be treated. Be the boss you would want to work for. Your team is an extension of you, and the way you lead directly impacts the way they perform.

In just a year and a half, I built a team of five entirely through word of mouth and literally the right place at the right time—not by actively recruiting, but by people approaching me, wanting to learn more about what I was building. They saw my dedication, work ethic, and the results it produced, and they wanted to be a part of it. That alone showed me that leading by example is one of the most powerful ways to inspire and grow a team.

I believe in leading with motivation and support, not just delegation. I jump in when needed, take on tasks alongside my team, and always make sure they feel valued. Small gestures, like buying lunch, recognizing their hard work, and showing genuine appreciation, go a long way in building morale. People want to feel respected, and when they do, they give their best.

At the end of the day, if you create an environment where your team feels respected, motivated, and proud to be part of something bigger, they will show up, work hard, and be just as invested in success as you are.

Contact Info:

• Website: https://chasingskysmarketing.com
• Instagram: cs.digital.marketing

Image Credits

All photos are taken by our CS Digital Marketing Team.