PP 202: Boss Dog on Escaping the 9-5, Finding Your Style, & Selling Merch


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The Secret = Being Yourself in Your Brand

So many people I talk to feel like they have to have all the answers before they can “confidently start” their creative pursuits.

The path is never clear in the beginning. You have to be on that level of “crazy” that you’re so borderline obsessively passionate/interested in something that you’re willing to pursue it no matter what happens.

You have to be committed to the dream yet embracing that things can always change. You just know you’re ready to enjoy the ride and show your work to grow along the way.

This brings me to today’s guest who has an inspiring story to back up their incredible work.

I’m talking about my new creative brother from another artistic mother, Mikey McKennedy of Boss Dogg Art Department.

Mikey, and his partner-in-crime, Sam, are an independently owned and operated artist brand slanging some of the most incredible artwork on the best merch in the universe. (Bold statement but true).

When they’re not partnering with behemoths like Zumiez, they’re creating one of a kind designs that pack a powerful message to inspire you to start living a life that’s true to yourself (while standing out and looking slick AF rocking their gear).

The road from side hustle to successful full-time grind today has been a rollercoaster, to say the least, and I’m hella pumped I get to share that journey with you today.

In today’s’ episode, Mikey and I chat about:

  • Setting yourself up with a plan to escape the 9–5.

  • Knowing what your brand is about.

  • Finding your aesthetic and owning it.

  • Committing to a path that isn’t always clear.

  • Getting started with merch, having a thick skin, and so much more.

Straight up, this has been one of my favorite conversations to date. 

If you’re ready to embrace yourself in your brand in order to make an impact and change with work that feels like play, then you’re going to dig this one.



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PP 203: Ben Jenkins of Warstic on Making Your Side Hustle Your Main Hustle

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BEST HITS | PP 125: Elizabeth Gray with 3 Tips for Growing Your Online Engaged Audience