Interested in starting your own entrepreneurial journey in arts but unsure what to expect? Then read up on our interview with Jake Kenobi, owner of Spring Break Jake, located in Bend, OR, USA.

What's your business, and who are your customers?

I am an Illustrator, Muralist, & Artist working under the moniker Spring Break Jake. My customers are anyone looking for my particular breed of artwork, whether they need apparel graphics, wall murals, or fine art commissions.

Tell us about yourself

I've been drawing since before I can remember, so becoming an artist and illustrator almost feels like destiny. I started off doing graphic design professionally. Then I got more specific doing freelance illustration work, and once I established my style, I started getting mural commissions and making fine art paintings. I'm motivated each day mainly by the sheer joy I get from practicing creativity but also by the chance to express my and my client's values through my art.

What's your biggest accomplishment as a business owner?

Practicing vulnerability and creating art around the causes I care about, such as mental health and climate change.

What's one of the hardest things that comes with being a business owner?

Being able to compartmentalize your business as much as you can so you're not thinking about it or worrying about it when you need to be resting or enjoying friend/family time. Breaks and separation are key.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Go to therapy! Figuring yourself out and cultivating self-compassion and self-awareness will only benefit every area of your life, especially your work.
  2. Be extremely clear on why you want to do what you're setting out to do. If it's for the right reasons, your why will only serve as motivation when times get tough.
  3. Lean on your existing relationships to find work/clients/customers.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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