We recently connected with Anthony Gregg and have shared our conversation below.

Hi Anthony, thanks for joining us today. We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.

CanvasRebel: Anthony Gregg “Taking A Risk” Life’s Journey

Diving headfirst into Gregg Design Company was the riskiest move of my life, both professionally and personally. But let’s set our time machine back about 30 years to a small farming town in NW Ohio. My family has owned John’s Sons Donut Shop for over four decades, a place where the sweet scent of Bavarian cream and apple fritters hung thick in the air! Growing up in a donut wonderland like that, my brothers and I learned life’s lessons while indulging in, let’s say, one too many donut holes. We were practically raised on a diet of hard work, humor, and the occasional sprinkle mishap.

It eventually led to working the graveyard shift in the back shop during high school. Those moments, shared with my older brother and sister-in-law, set the stage for my future. It was those moonlit cigarette breaks on the curb that hold dear to my heart to this day. Their mentorship created a safe place to think bigger and to elevate my mind on what is possible in the world today.

Despite these experiences, I was initially hesitant about leaving the comfort of my small town and setting sail on my own. In my last two years of high school, I attended a vocational school, where I found communication arts and discovered a career path for those who loved to draw. My teacher provided invaluable mentorship, boosting my confidence in illustration. I knew this was the direction I wanted to take for my career, and so, in my senior year, I applied for scholarships to the Art Institute of Pittsburgh and the Art Institute of Seattle.

The day the Art Institute of Seattle called to inform me that I had been awarded a quarter-tuition scholarship was a moment filled with excitement, fear, and commitment. This scholarship, along with the support of my family and older brother, allowed me to become the first person in my family to attend college, and I ended up in the Pacific Northwest, far from my Ohio roots.

Arriving in Seattle, I was essentially fresh bait, with no clue about what may lay ahead. It was just me, my art supplies, and my skateboard. The sight of mountains and the ocean air left me in awe, but it also marked the beginning of my first significant challenge as a young adult – proving that I could make it on my own without letting down the family that believed in me the most.

While adapting to this new environment, I also grappled with shyness and a wild side that occasionally got me into trouble. Alcohol and weed became my coping mechanisms as I navigated the unfamiliar territory of Seattle. Still, I was determined to show that the Midwest had molded some of the hardest-working and most genuine people in the country. I was no longer a local, but I held onto my small-town ethos as I tried to make my presence known.

In college, I threw myself into every project, working tirelessly to prove my worth and gain recognition for my work. I also had a job while in school and found a positive release at the local skate parks, where my wild side had a creative outlet. The skate culture in Seattle pushed my boundaries and expanded my sense of what was possible. Through these new relationships, life took on new meaning, and I discovered a sense of fearlessness.

During my sophomore year of school, I decided to take the plunge and move into a house with my buddies, Rob and Mitch. Little did I know, this would be a friendship for the ages. Rob and I shared a passion for art, music, and every obscure art movement you could think of. Oh, and let’s not forget our mutual love for partying! We pushed each other academically and held each other accountable – even if it occasionally involved a bit of property damage and a 4 AM Pat Benetar concert in our living room!

Next entered the “Mortar House” days, a skate punk haven where I faced a growing contrast between my current reality and where I was supposed to be. Picture this: basement mosh pits at death metal shows, skateboarding sessions on the collapsed garage roof, and the occasional, uh, ‘pyrotechnics’ display with M-80s making their way into the fireplace. And all the while, I was somehow trying to keep it together and finish up my last year of school! Sure, I might’ve made a few regrettable choices and burned a bridge or two but it was all part of my wild journey.

At the skatepark, I encountered my second mentor, Chris Farrar of Stonefly Design, who owned a screen-printing shop. It took me a year to convince him to give me a chance. Chris took me under his wing, teaching me the art of screen printing, and more importantly, serving as a positive male role model in my life. He played a pivotal role in shaping both my professional and personal growth.

Meanwhile, Rob had moved back to Reno, Nevada, after school and landed a fantastic job designing backstage passes in the entertainment industry. I stayed in Seattle, continuing to work with Chris. However, I knew that being a screen printer wasn’t my ultimate destiny, and I longed to return to the world of design and illustration. Seattle’s competitive design market posed challenges in securing a job with my student portfolio.

So, I decided to roll the dice once again, and thus, Risk number 2 was born: “Let’s roll to Reno!” With Chris’s guidance and help, I acquired Donuts, A Beat Up ’77 Ford Maverick, and a Pink Boombox. I had a meager $900 in my pocket, which I was convinced would cover my first month’s rent in Reno. Optimism was my co-pilot! I crash-landed at my buddy Rob’s place, determined to find work in the design industry and hoping to secure a position with the firm he worked for. However, there were no immediate openings, and they referred me to their competitor in town.

Undeterred, I applied to both companies and began visiting various design agencies in person, leaving my resume and sample work behind. I’d strategically park my ’77 Maverick, complete with a pink boombox blasting ZZ Top, around the corner so they wouldn’t see what I was driving. After two weeks of relentless effort, I finally secured a job at Reno Type, diving headfirst into a larger scale print company. This experience laid the foundation for my understanding of print and letterpress printing, leaving a lasting impact on my design style.

Fast forward two years, and I received a call from the competitor that had previously turned me down with no openings at the time. This new opportunity allowed me to have my first full-time design job, and I was on my way to Cube Services, Inc.!

Cube Services, Inc. turned out to be a pivotal job that shaped my experience in the design and print industries. Cube specialized in backstage passes and security credentials for the entertainment industry, and was the king of the backstage pass world. My love for print and the fact that Cube manufactured everything in-house made it the perfect place for a budding designer like me. It was like a playground of specialty printing on steroids—foil, UV, glow in the dark, advanced variable printing, die-cutting, metal, you name it. I loved the work culture at Cube and built lifelong friendships with my colleagues.

I became part of teams that excelled in design, winning multiple national design and illustration awards, along with over 30 local and district awards for our backstage pass and collateral designs. My buddy Rob continued to be a huge design influence even though he worked for our competitor company. His trust and similar path is a true bond that we developed over the years. After 15 years, and as I started a family with my wife, Andrea, I began to wonder what more was out there. Approaching my 40s, I realized that I was becoming an aging designer who needed to stay relevant in the digital age. It became a running joke that I was just a caveman designer trying to survive in the digital world. What would I do if I lost my job or needed to find work elsewhere? The COVID-19 pandemic intensified these concerns and forced me to seriously reconsider my career path. It was a daunting but necessary step.

During my time at Cube, I also developed a passion for logo design and sought to learn more about brand identity and how it helps companies achieve greater awareness, align their mission and vision internally, and connect more authentically with their target audiences. This interest led me on an educational journey that I’ve been exploring for the past five years, ultimately shaping my next move.

While working at Cube, I also took on freelance projects on the side, increasingly focusing on branding and logo design to build my portfolio. It proved to be a challenging endeavor, often leading to burnout. With young children at home, maintaining focus on my professional goals was difficult, and I often felt like I was falling short both at home and at work. However, I knew that I needed more experience to confidently strike out on my own.

Lacking a background in design agency operations, the concept of understanding and running a freelance business was intimidating. While at Cube, I enjoyed benefits like insurance, a reliable paycheck, and retirement plans, but I wasn’t seeing a clear path forward, and I wasn’t happy. With a family to help support, I needed to save, crunch numbers, and devise a plan for a more calculated risk. It took me five years to consider making this risk a reality. Tragically, during this period, my close friend Rob’s unexpected passing served as a poignant reminder of life’s fleeting nature and the profound significance of our choices.

I finally took the plunge and resigned from Cube, taking a part-time job with a reputable boutique design firm in Reno. This opportunity allowed me to delve deeper into brand and visual identity systems, understand how different agencies operate, gain exposure to website projects, learn about financial management, improve time tracking, and enhance my client communication skills. It was a challenging time in my life, as I had just left a company I had been with for 15 years and was struggling to adapt to a new design firm with a different culture. It felt like going through a divorce and not understanding the world I had left behind.

My freelance side gig continued to grow, gradually becoming my long-term goal. Freelancing was where my passion projects thrived, but I needed more experience to transition it into a viable business. I was terrified, but I found myself at another crossroads, unable to fully dedicate my time and energy to both my job and my freelance work. Something had to give, and I was reaching a boiling point. At 40, I was no longer as fearless as I had been in my youth, and self-doubt crept in, affecting both my professional and personal life. This was a low point, and I stood on the plank of either sinking or soaring. I wanted to be more present for my family and reshape Gregg Design Company with a new perspective, helping clients understand the purpose and strategy behind branding. However, I was deep in a hole, trying to figure it all out for myself.

And then, I took the leap! This time around, armed with more than $900 and a battered pink boombox, I decided to go all-in. With the unwavering support of my wife and our family, I threw myself into the venture that would become Gregg Design Company. I didn’t hold back – I enrolled in freelance courses, immersed myself in the intricacies of brand identity and strategy, and continued my illustration projects to keep those creative juices flowing.

Our deep-rooted passion for design, coupled with our extensive background in illustration, sets us apart from the crowd in our industry. Today, we’ve sharpened our focus on collaborating closely with our clients to define their strategic vision before diving headfirst into the design process. This approach not only solidifies our sense of purpose but also empowers us to create a lasting impact for our clients and our community. It brings much-needed clarity to the design journey, ultimately helping our clients achieve their goals.

As Gregg Design Company approaches its second year in business this spring, we reflect on the journey we’ve embarked upon. The past year was like a roller coaster ride without a safety harness, filled with incredible highs and humbling lows that illuminated areas where we needed to grow. It was a powerful motivator, driving us to build an all-star team of talented contractors who can handle any job, regardless of its size or complexity. Our specialty lies in logo and brand design. Our distinctive style strikes the perfect balance between emotion and functionality. Every case study in our portfolio exudes energy and attitude, but we also recognize when to temper these qualities to suit the specific needs of a project. This understanding is what positions us as the kind of design studio that businesses turn to when they want their brand to shine.

Taking the risk to establish and nurture Gregg Design Company has provided a profoundly humbling approach to business building. It has allowed me to not only shape our company’s future but also to recognize my own areas for personal growth. One of the most significant rewards has been the newfound flexibility in my schedule, enabling me to be more present with my wife and, most importantly, our children. Through their innocent and unbiased perspectives, I find endless inspiration, knowing that our actions can have a lasting impact. When I look back in 10 years, I’ll cherish the memories of being able to drop off and pick up my kids from school, volunteering with their sports and activities, and realizing that I took a risk to create a brighter and dream-oriented future. I want my children to understand that I gave it my all, no matter the unknown outcomes that may lie ahead.

Anthony, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m Anthony Gregg, founder of Gregg Design Company. We’re not your typical design studio. In a world swarmed with template based designs, we champion uniqueness and defy the mundane. Our journey started from a passion for art and individuality, rooted in a passion for art that grew from NW Ohio to the Pacific Northwest and the high desert of Reno, Nevada, which led to the creation of a studio where creativity is our guiding principle.

We specialize in brand identity, logo design, and illustration, but our core lies in crafting stories that resonate. We ignite our clients’ raw voices, bringing purpose to their missions with designs that balance emotion and functionality. Our approach? Collaboration and understanding the soul of each brand.

What distinguishes us? Our dedication to working with, not just for, our clients, and our knack for creating designs that truly embody a brand’s spirit. We’re not just about grabbing attention; we’re about capturing the heart of your brand.

At Gregg Design Company, we’re proud to weave unique brand stories with lasting impact. We’re thrilled to have forged international connections, like our decade-long friendship designing for Bergenfest in Norway, working with icons like George Thorogood, and helping local businesses find their voice. All this while balancing roles as a husband and being a dad. Join us on a journey where your vision evolves into a compelling, unforgettable narrative.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

I touched on this within our main story “Taking a Risk”!

Have any books or other resources had a big impact on you?

Absolutely! My main guidance for setting a foundation to start my freelance career was the amazing incredibly in depth course from Micheal Janda called “The Ultimate Freelance Course” and I am also involved in his mentorship program called “More Creative Academy”.

https://michaeljanda.com/courses/
https://morecreativeacademy.com

Books:

Mindful Creative by Radim Malinic – Mental Health for Designers

Creativity for Sale by Radim Malinic

The Pen & Ink Book, Materials and Techniques for Today’s Artist by Jos A. Smith – Illustration principles book from college that I still reference to this day

Manage Your Day-To-Day: Build Your Routine, Find Your Focus & Sharpen Your Creative Mind – By 99U

The Creative Act: The Way of Being by Rick Ruben

Contact Info:

• Website: www.greggdesignco.com
• Instagram: @greggdesignco.com
• Facebook: @greggdesignco.com
• Linkedin: @greggdesignco.com
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