Interested in starting your own entrepreneurial journey in fine arts but unsure what to expect? Then read up on our interview with Matt Philleo, Founder of Fine Art by Matt Philleo, LLC., Realistic Acrylic Portrait School, located in Chippewa Falls, WI, USA.

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

I am a professional portrait artist. I paint custom acrylic portraits for collectors worldwide. I also teach artists how to paint realistic portraits they can be proud of.

Tell us about yourself

I’ve always loved doing art. As a child, I would draw pictures to pass the time. My mom noticed and encouraged me to keep drawing. When I was 14, I could draw a portrait of one of my favorite rock bands that looked just like a photo! I started getting commissions around this time, and it encouraged me to keep going.

Art school didn’t quite work out for me, as they pushed me into abstract work. I ended up doing a lot of different jobs to make ends meet. Finally, when I was 32 and my job was downsized, I decided to step out in faith and use the talent God gave me as a full-time artist. The first few years were a real challenge. Some months we didn’t have money for rent. We had two young children, so it was kind of scary! But my wife and I would pray. And God would often provide a commission or painting sale to keep us afloat.

Finally, in 2016, I started teaching portrait painting. I had no experience at all, but some fellow artists in a co-op gallery encouraged me to do it. And I found I liked it! I taught what I had been doing for several years. I began recording classes and lessons on YouTube and Teachable. Each day, I am motivated by a desire to glorify God with the talent He gave me and serve the people I influence.

What's your biggest accomplishment as a business owner?

In the spring of 2020, just when the COVID pandemic hit, I was worried about what would happen, like many business owners. How could I teach classes or sell my work? A successful online entrepreneur I follow, Graham Cochrane, said on a podcast, “while others are holding back out of fear, this is a time to be insanely generous.”

Then an idea hit me: what if I start a portrait painting challenge in my Facebook group? What if I teach people how to paint a portrait in acrylic from start to finish—for free?

“But no one will ever buy your courses again,” a thought accosted me. But I felt like God was saying, “Be generous. And trust Me.” So I did. I kicked off the Acrylic Portrait Painting Challenge in April. Over 700 artists from all over the world signed up to take it!

I taught the entire process of painting a portrait. Some artists were advanced, but most were complete beginners. So many artists painted realistic portraits for the first time! And several wrote me and told me this challenge kept them from fear and despair during the lockdowns.

In the end, I opened up a subscription-based membership website for more classes, and over thirty people joined! My business grew exponentially during COVID. I am proud of these artists who have succeeded in their skills and are painting beautiful portraits of their loved ones or on commission.

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

Focus is one of the hardest things about being a business owner. What should you do next? You don’t have a boss telling giving you work assignments. You don’t know what daily activities will pull the right levers to keep the business profitable.

The second most challenging thing is to know how to balance your time. Because you set your hours and agenda, work can easily flow into your family life if you let it. But the freedom and flexibility are excellent. It’s a double-edged sword. I try to keep the blade going in the right direction!

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

If you want to start a business, go with the online model. There’s never been a better time to be an entrepreneur than today. There are many online apps, software tools, and venues to build an audience that knows, likes, and trusts you.

The information/ teaching business is the best way to go. You have no inventory and little overhead. You can start nearly for free. Look at what you’re good at doing and have a passion for. Then, start teaching others how to do that same thing.

You can build an audience on Facebook and YouTube for free. Invite people to join your email list by giving them something valuable in exchange, like a free mini-class or downloadable PDF guide. Then, continue to add value by sharing helpful tips and teaching with them. After doing that, you can sell books, classes, products, or coaching services with them. The sky’s the limit!

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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