We’re excited to introduce you to the always interesting and insightful Casey Bollinger. We hope you’ll enjoy our conversation with Casey below.
Casey, thanks for taking the time to share your stories with us today What were some of the most unexpected problems you’ve faced in your career and how did you resolve those issues?
One of the most unexpected and challenging problems I faced in my career was getting laid off from a company I had dedicated my heart and soul to for five years. I worked for a national chiropractic franchise, starting when they didn’t even have a logo. I took on the enormous task of creating their brand identity from scratch. This included designing the logo, establishing the brand’s voice, colors, and rules, developing their website, and eventually building their national advertising and marketing strategies. The company became my passion project, and I treated it with the same care and dedication as if it were my own.
Then, unexpectedly, the company decided to move its headquarters from San Diego to Arizona. Along with this move, they revoked our unlimited vacation policy (which we rarely had time to use anyway) and required everyone to relocate. Remote work was no longer an option. I couldn’t subject myself to these new conditions and was let go within two weeks, with no severance or contract work to cushion the blow.
Finding myself suddenly unemployed, I spent the next three months applying to at least 20 jobs a day, with little to no response. It was a devastating experience, one that many of my friends and peers were also facing. The job market was oversaturated, especially in the creative industry, with many people being let go from startups and tech companies downsizing post-pandemic. The integration of AI into various roles added another layer of difficulty.
Despite the overwhelming circumstances, I tried to maintain a positive outlook. I moved out of my apartment to save money, living in my truck and staying with friends. Then, an opportunity to caravan down to Mexico with some friends arose, and I seized it. We stayed on beautiful, free beaches, using Starlink internet to stay connected. This adventure turned out to be an absolute dream. I met amazing people who were on similar journeys, discovered a new hobby in paragliding, and eventually made a connection that led me to my current job in West Yellowstone, MT.
This period taught me invaluable lessons about resilience and adaptability. Rolling with the punches and taking advantage of every situation became my mantra. I learned that our attitudes significantly shape our experiences. Choosing to see challenges as opportunities rather than setbacks made all the difference. Losing my job allowed me to take a much-needed break, make new connections, and ultimately find a job I truly enjoy.
I firmly believe that our perspective determines how we navigate life’s toughest obstacles. We can choose to see a layoff as a failure or as an opportunity for growth and new adventures. Embracing positivity, trust, and love for life, I’ve found that the universe often responds in kind. Staying prepared for the worst while expecting the best has helped me see the beauty in every twist and turn.
Remember, it’s up to us to decide how we let challenges affect us and how we overcome them. By choosing a positive outlook, we open ourselves up to the incredible possibilities that life has to offer.

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 was born and raised in Raleigh, NC, and graduated from the School of Design at NC State University with a degree in graphic design. My journey into the world of marketing and design began with a passion for creativity and a keen interest in how visual communication can influence perception and behavior.
With over 15 years of experience in the industry, I’ve consistently driven revenue growth through strategic brand positioning and compelling storytelling. My career has given me the opportunity to work with a diverse range of clients, including celebrities, tech startups, billion-dollar industries, franchises, and small businesses. This breadth of experience has allowed me to understand the unique challenges and opportunities across different sectors, and to develop a versatile skill set that I bring to every project.
As a growth-focused marketing and creative leader, my mission is to shape marketing strategy and creative direction in a way that fosters meaningful connections between brands and their audiences. I strive to produce innovative ideas and avenues that elicit positive reactions and engagement. By creating the right brand voice, positioning, and marketing execution, I focus on driving demand and ensuring that brands resonate with their target audience.
One of my core philosophies is building brands with sustainability. I believe that a brand should not only capture attention but also stand the test of time. This involves creating a cohesive brand identity that reflects the company’s values, mission, and vision, and implementing marketing strategies that are adaptable and forward-thinking.
I’m most proud of my ability to adapt and thrive in an ever-changing industry. Whether working with high-profile clients or small businesses, I approach each project with the same level of dedication and enthusiasm. My work is driven by a genuine passion for helping brands grow and succeed.
For potential clients, followers, and fans, I want you to know that my commitment goes beyond delivering excellent results. I aim to build lasting relationships based on trust and mutual respect. I take the time to understand your unique needs and goals, and I tailor my approach to ensure that your brand not only meets but exceeds expectations.

Is there mission driving your creative journey?
The driving force behind my creative journey is the lifestyle and adventure of the outdoors and nature. I find immense inspiration in combining nature with technology, allowing me to work while being immersed in the natural world. This unique blend fuels my passion and keeps me motivated every day.
Being outdoors not only provides a refreshing environment for creativity but also connects me with a community that shares similar values and aspirations. I believe in the power of nature to inspire and rejuvenate, and I aim to bring that sense of wonder and connection into my work.
My mission is to create opportunities where technology and nature can coexist harmoniously, enabling a lifestyle that embraces both adventure and productivity. Whether it’s through innovative marketing strategies, sustainable brand building, or community engagement, I strive to provide value to the community while maintaining and nurturing our natural surroundings.
This commitment to balancing work with the beauty and serenity of the outdoors is what keeps me going. It’s about more than just a career; it’s about fostering a way of life that encourages exploration, connection, and sustainable growth. Through my work, I hope to inspire others to see the potential of integrating nature and technology, and to pursue their own passions with the same fervor and dedication.

Any advice for managing a team?
When it comes to managing a team and maintaining high morale, it’s crucial to remember that teams are made up of individuals, each with their own unique strengths, perspectives, and motivations. Reflecting on what makes me appreciate a company or feel enthusiastic about my work helps guide my approach to leadership.
One common pitfall managers can fall into is micromanaging. It’s easy to think, “I know how to do this perfectly, so I’ll just show them and have them watch,” or “I’ll tell them exactly what to do to save time.” While this might seem efficient, it can stifle your team’s growth, hinder their problem-solving abilities, and dampen their enthusiasm for contributing their own ideas.
Instead, I believe in empowering team members by giving them the responsibility and trust to take ownership of their projects. When people have more responsibility, they naturally develop a stronger dedication to their work and strive for better results. A good mentor should guide and educate, but also allow their team the freedom to explore their creativity and solve problems in their own way.
Creating an environment where it’s okay to make mistakes is vital. As Ms. Frizzle from The Magic School Bus famously said, “Take chances, make mistakes, get messy.” This adventurous spirit should extend into the office as well. Encouraging a bit of adventure can spark new creative ideas and lead to unique solutions, just as it does outside the workplace.
Laughter and camaraderie are also essential for high morale. Whether in the office or on Zoom calls, make space for humor and light-hearted moments. These interactions build stronger relationships within the team and create a positive and enjoyable work atmosphere.
In summary, managing a team effectively means fostering an environment of trust, responsibility, and creativity. Avoiding micromanagement, encouraging ownership, allowing for mistakes, and promoting a sense of adventure and humor are key elements. By nurturing these aspects, you can build a motivated, innovative, and high-spirited team that is eager to contribute and excel.
Contact Info:
- Instagram: casey_bear
- Linkedin: https://www.linkedin.com/in/caseybollinger/





