Interview with Pep Rally Inc.

Our Interview with Pep Rally Inc.

We recently had the pleasure of sitting down and chatting with the awesome crew over at Pep Rally Inc, Jay Giroux, Josh Pearson, and Greg Bryon. A group of talented painters, illustrators, photographers, builders, and overall creative powerhouses, we’ve have a hard time concretely saying what each of them do. As we’ve come to find out, each member of Pep Rally contributes various skills and talents to each project, so defining them as only painters or only photographers does them no justice. You can check out their website HERE, as well as checking out their Facebook, Instagram, and Twitter.

With out further delay, please enjoy our interview with the founders of Pep Rally Inc.


Was there a specific moment during your young creative career where you decided to pursue art or design or just being a creative in general?

The short answer for all of them was no. There was no defining moment where they suddenly realized that they wanted to do this one thing for the rest of their lives. Generally, all three members said that they found something that they love by way of natural progression. They had a skill set and there was a lot of trial and error in figuring out where they could apply those skills; Josh said “There was never a moment where I said ‘Maybe I’ll be an attorney’… It was more so ‘What can I do with this skill set?’” All three talked at some point about how the creativity was always there and that finding it wasn’t really the issue; it’s figuring out how and when to apply it.

What’s been the most difficult part about selling yourselves as creative entrepreneurs?

Defining yourself as a creative has been and will always be a struggle for many. This was one of the bigger points Pep Rally had to make about setting yourself up as a creative and more specifically as a creative entrepreneur. Here’s what Josh had to say: “The biggest struggle is narrowing down what it is that you do and making sure that you’ve worked on your craft so everything that you do is on the same level.”

Another challenge faced by every creative is having the guts to tell someone that you’re good at what you do; finding that self-assurance and telling yourself that the work that you put out is solid. Jay said, “Probably [the hardest part of being a creative entrepreneur was] gaining that level of confidence where we could understand our value and just asking have a crack at [client work].”

One of the last struggles we talked about as far as being a creative entrepreneur goes was building something with other people, while trying to make sure that everyone is fulfilled by their work. Collaboration is great, but not when it stifles your wants and needs; it’s all about finding balance, which Greg talks about later.


Josh Pearson

What were the steps that you all took to build your client base?

This was an especially interesting discussion, not really because of the question, but because the answers morphed from how Pep Rally Inc built their client base to how to be the best creative you can be and then again into how real things get as an entrepreneur; it started off with building a rapport with clients. The members from Pep Rally said that they were able to build a client roster by showcasing their work which meant inviting people to their job sites. Jay told us, “We did something that showed a variety of what we could do. We were smart by inviting people in during the actual building process, so people were getting excited because they got to see the project come to life. And then when we finished the installment, it got a lot of attention.”

They said that, as you could guess, being an entrepreneur at first is hard, really, really hard; “we had no idea where clients were going to come from.” One of the things that they said helps with not only building a client base but also with being a better creative is to be invested in the creative community. Each member of Pep Rally has side projects, hobbies, and passions that they pursue outside of their work; sometimes those things coincide with their job, and sometimes they don’t. Being an active player in your community is what Josh said helped them out in the beginning, “What this lead to, and what I didn’t expect and was overwhelmed with, was that when we finally did decide to jump and we created Pep Rally Inc, the out pouring of support was incredible.”

On the contrary, in response to taking that leap of faith, Jay told us not to quit our day jobs. The advice that given was to go to work and get as much out of it as you can like meeting new people, doing things that you don’t know how to do, and getting stuff done. Then after that, you get home and you work on what you want to do. The thing or things that make you happy or fulfill you in ways that other things can’t. Jay said to “have the understanding that it’s a slow build,” and that you “…kind of just chip away and chip away.” Here they emphasized the importance of keeping your own creative identity, especially if you work in a creative environment, “it’s important for you to have your own creative outlet, because then you have a net; you can always go to that thing that encompasses you. If you’re a creative and you’re in or own a creative business and that’s all you invest in, you could start loosing your sense of self or the reason of why you started in the first place.”

And the last snippet of wisdom on this topic came from Josh, as he said that there’s a fluidity between personal work and work for your job, “I love that back and forth: define yourself as a creative, do good client work, do something in between, collaborate and then mix it all together. It makes everything better. It makes your client work better, it makes your personal work better, and it makes your team better. I love that.”

Pep Rally Hero

Jay Giroux

Is it hard to balance all of the aspects of your life, from work, to being a creative, to family and friends to side passions to anything else?

All of them laughed at this question. When we met them with blank stares, each of them said something to the effect of “Every single day”. They each had their own advice to give and their own experiences to share about keeping all of your life aspects in check.

Jay talked about how, as a creative, you have to come to the understanding that it’s ok to not do everything all at once. He thinks about painting all day, every day and since he knows that about himself he said, “I can put it aside for a second to focus on this other thing. Or getting this other thing organized, and then I can move back around to it, that thing that anchors me.” When we try to take on everything all at the same time, we put ourselves in danger of burnout; “it’s ok sometimes to just put things aside, focus on this one thing, get that going, and then you start to feel ok because you’re not pressuring yourself.”

Greg takes a different approach to balancing the aspects of his life. He told us that instead of separating all of the elements of his life, he views them all as one thing, one experience, one unifying life experience that has all of these moving parts. Greg said, “I always say it’s my life, meaning that if I have a whole bunch of stuff to do that pertains to keeping my lights on, or going to get something to eat, or traveling and producing work; there’s no separation for me. Work, life, hobbies, family, all of that stuff, it’s all at an equal level for me and I try to keep it there.”

We wrapped up this question with a response from Josh, who talked about the potential pitfalls of having a life where all of the aspects are closely related, work for your job and personal work, for example. He told us that one of the harder parts to being a creative and loving your work is finding that balance, like Greg said, and not putting one or more aspects of your life on the back burner; “The thing that tends to happen is that the people closest to us pay the hardest price.” Josh talked about times where making time for loved ones or anything outside of work was incredibly hard, especially when he was in the thick of it; “I think that’s the hardest part about all of this is finding that balance so that we don’t push away the people that are closest to us and that care about us the most.”


“It’s about taking what you do know and applying that knowledge to what you want to do and where you want to go.”

– Greg Bryon

If you had to give advice to any aspiring creative, what would it be?

This question elicited about 15 to 20 minutes of some amazing advice. Since they all had something to add, we’ll break it up by the individual again.

Josh started out by touching on the topic of opportunities and how a lot of people wait for them to get started on anything. He said, “I don’t feel like it works that way. Yes, it’s super risky to quit [your day job] and do those other things, so you start working now. You do the things you want to do. Instead of waiting until a client says “Here’s a great website for you to build”, just build that website. Build what you want to build, constantly. Get there how ever you want to get there.” Josh said that the single most important thing for any up and coming creative is to work every single day towards the life that you want.

The second piece of advice that he gave was to always learn from the people around you. He told us to stay humble, especially in the beginning because when you keep your ego in check, you realize that everyone you meet on your career path can teach you something; “See what they have to offer and then define what you have to offer and always, always contribute that. Give it everything that you have. Give it everything that they gave you when you couldn’t give it.”

The recommendation that Greg gave was to achieve some sort of balance in you life, while also figuring out how you can apply the experience that you already have to get you to where you want to be. He talked to us about his college career and about how a lot of college goers or young creatives feel pressured to figure out their entire lives right now; “college makes a lot of people crazy because you feel like you have to set the rest of your life in concrete, but that’s not how life goes.”

He also touched on how one of the keys to being happy is in being ok with where you are, and never being desperate to get to somewhere where you’re not; “Find balance and never chase; never chase the money because then you can’t enjoy it once you have it. You can’t even chase the feeling of enjoying stuff because it’s not something that you find; it finds you.”

Lastly, Jay helped wrap up our interview by offering some insights on taking the time to make sure that you’re doing things right. He told us that “It’s the whole rabbit and hare thing. You’re going to get there regardless, so you could get there gracefully, or you could get there in a hurry and be flustered. But not being there right now makes people uncomfortable. So if you can take some of that energy and conserve it, or put it into other aspects of your life, it’ll go a long way.”

This lead to an interesting point, which was that a lot of creatives put an enormous amount of pressure on themselves to always be better or to get where they want to go right now and to stay relevant. Jay told us that your career, or how you spend your life is a long, and sometimes hard road; “I think that you could take the long road and just sort of, be consistent. It’s so incredibly important to be consistent. Always be putting out work and never too much, and never too little, but like Greg was saying, just finding that balance.

We ended the interview by talking a bit about how what all of us are doing right now is something that our future selves will thank us for. The trials and tribulations that we face on a daily basis, the ones that pull us down and drag us through the dirt, the ones that steal our breath; those are the things that help us grow. Take what you have right now and apply it to where you are right now to get to where you want to go.

If you enjoyed reading the highlights from our interview with Pep Rally and are looking for more, you can find the complete transcript HERE.

We wanted to give a huge shout out and thanks to Pep Rally Inc. for providing us with amazing art, inspiration, and incredible insights. Thank you to everyone for reading and keeping up with us! Be sure to follow us on FacebookInstagramTwitterLinkedin, and Dribbble for more cool interviews with creatives in the Tampa community!