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

Jack, looking forward to hearing all of your stories today. What was one of the most important lessons you learned in school? Why did that lesson stick with you?

After receiving a degree in Communications I enrolled into a graduate-level advertising school based in Minneapolis, MN. Although, mostly a portfolio program, I honed in on learning creative processes and how to fully embrace the concept of monetizing creative work.

At the time, I didn’t realize how vital a certain class I had was. This class was called Creative Solutions.

I was taught how to leverage being ‘creative’ and how to be prepared in different professional settings to keep the fresh ideas rolling in.

Creative Solutions highlighted the intangible skills of what makes a great creative: effectively receiving feedback, having an endless well of new ideas, and how to work through writer’s block/fleeting motivation—all while doing this in high stress business environments.

As years went on and I started taking a more directorial role leading a creative team, I found myself going back to practices I learned in this class specifically. Among many other techniques I encourage my team to practice when facing creative barriers—the single most important to success has been something called “morning pages”.

Essentially, the idea is to convert whatever thoughts, images, and ideas you have as fast as possible in journal format. It was recommended to do this as the first activity you do each day—hence the name “morning pages”. For 10 minutes, do not stop writing. Do not stop to ponder readability, grammar, or structure. Do not tell yourself “this makes no sense”. Even if we had no ideas, we were ironically instructed to write about our writer’s block. Just get an ‘endless flow of consciousness’ onto the page. It could be related to a current project, what you want for breakfast, or anything that comes to mind.

The lesson learned that stuck with me practicing this technique is that ruminating is a creative’s worst enemy. Morning Pages is all about embracing the ideas that aren’t directly related to your work as an anrtist and being able to compartmentalize our consciousness and letting the dust settle. Eventually, you will find your focus sharpens as you narrow down and get into a flow state of mind. If you don’t stop for anything and just emphasize bringing your ideas into the physical world by writing them down that, eventually, one will stick.

Jack, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

Jolly Mammoth Co. was born from a desire to create something refreshing in the world of branding. I started off freelancing where I worked exclusively with environmental/sustainability clients. However, I soon realized that as a freelancer, I was stuck in a never-ending cycle of client acquisition and project delivery—without the ability to charge agency prices. It wasn’t sustainable. This led to the idea of scaling my work into a full-fledged agency, so I could offer a higher level of service, creativity, and strategic value.
Years after this idea was seeded, I came across a group of like-minded individuals with complementary creative talents and quickly hit the ground running. At Jolly Mammoth Co., we specialize in branding services for clients in creative industries, particularly those either starting out or undergoing a rebrand. Our process begins by working closely with business owners to understand the heart of their brand—what they want it to represent, how they want it to connect with their audience, and what their vision is for the future. From there, our talented team of creatives—including copywriters, graphic designers, and video producers—help bring those ideas to life with tailored branding solutions. Whether it’s revamping a website, redesigning a logo, or defining a new tone for a brand, we ensure that every project is aligned with the client’s unique goals. One challenge many clients face is articulating their brand to a specific target audience, especially when they’re not part of that audience themselves. We help bridge this gap by developing brand identities that speak directly to their ideal market, making their messaging and positioning more impactful.
What sets Jolly Mammoth Co. apart is our commitment to offering creative services specifically for creative people and brands. Unlike traditional agencies that may rely on cookie-cutter solutions, we approach every client with a blank canvas. We’ve cultivated a team of distinctive creatives whose individual styles cannot be replicated, allowing us to provide highly customized and authentic branding. Our boutique agency model allows us to be mindful and selective in selecting the contributors we work with, ensuring that each project we take on is infused with passion, individuality, and a fresh perspective.
I’m most proud of the fact that Jolly Mammoth Co. has become a reliable partner for clients who want their brand to truly reflect their vision and mission. Being able to offer a full suite of creative services—while maintaining a personal, collaborative approach—has been incredibly fulfilling. I’m also extremely proud of the talented team we’ve built; their passion for our clients’ brands is unmatched, and they truly go above and beyond to make each project a success. Without them, none of this would be possible.
At Jolly Mammoth Co., we live by the motto that life should be lived in a way that makes you “jolly.” Our agency is founded on the belief that when people embrace their passions, they lead more fulfilling lives—and that same philosophy drives our work. We help clients unlock their creative potential and offer business solutions that turn dreams into reality, all while staying true to the individuality of each brand we work with. It’s about more than just branding—it’s about building a life and business that aligns with what truly makes you happy.

How do you keep your team’s morale high?

I constantly reiterate to my team how I am still learning how to be a better leader with each new project. I remember a time when the thought of leading a team in the role of Creative Director gave me a lot of unease and anxiety. It was frightening, in some regard, to entrust others with the brand reputation, and trust that whatever feedback/direction I give will be clearly communicated in reaching the end goal. I found two key things that helped to overcome this. 1) Clearly lay out expectations. Like players on a sports team, the agency contributors need to be able to rely on each other to fulfill their individual role. I know what to expect of the creative contributors and they know what to expect from me as creative director. We believe communication is the most beautiful language in the world, and use it frivolously. 2) Take each win, setback, and confusing situation with a grain of salt. The minute you start to ride the ups and downs that are innate with leading a team & running a business is the minute that you become subject to the results over the process. Trusting your mission and reminding yourself why you started on this certain path is the best way to ensure longevity.

For you, what’s the most rewarding aspect of being a creative?

The most rewarding aspect of what I do is being able to meet and work closely with some amazing creative people. The peace of mind that comes with doing something I am passionate about is rewarding on its own. Doing it in a professional environment to help others do the same is a cherry on top.

Contact Info:

• Website: https://jollymammoth.co
• Instagram: https://www.instagram.com/jollymammothco/