We were lucky to catch up with Melissa Weinman recently and have shared our conversation below.
Melissa, thanks for joining us, excited to have you contributing your stories and insights. Let’s start with inspirations and heroes. Are there any historical figures you look up to?
I have been a fan of Bob Ross as long as I can remember. Watching him paint always feels like you are watching someone perform magic. He makes it look so easy! I grew up loving art and I dabbled in painting as a hobby, but I never seriously thought about teaching art. The laid back atmosphere of the new paint & sip parties my friend had started instructing made me comfortable with leading people through a painting, and the painters got great results! It was in 2014 that I started my own Paint & Sip business called Happy Trees Painting, with Bob Ross as an obvious inspiration. Bob says that, “talent is pursued interest,” and I try to spread that message to my customers any chance I get. I see so many people who come in and are afraid to put the brush to canvas or have anxiety about how well they will be able to paint. During the two hour class I work them through some of these fears and at the end of the class they have surprised themselves by what they were able to accomplish. Stepping outside your comfort zone, and having a work of art that you are proud of, is a great feeling. I hope people can take the experience of accomplishing something they didn’t believe they could do, and apply it to all kinds of areas in their lives.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
My creative journey started a little over 10 years ago when I came home from the 2011 Winfield Bluegrass Festival. I was determined to learn the guitar. I would practice along to a beginner’s guitar DVD every day when I got home from work until I got to know the chords pretty well. I had friends who were also learning to play and we got together to play cover songs and eventually writing our own original songs. We named our band Good Time Charley, and we started to book shows. It was a scary thing to stand in front of people and perform. Logically, I had a lot of reasons to be afraid (like not being very good at guitar) but my anticipated failures never really panned out. We had fun, played a good show, and then went on to play many more shows.
The experience of learning skills I once considered out of reach really opened up the way I approached life. Not long after I began to play music, an opportunity came along to teach painting classes for a friend’s business. I was not a confident painter and actually resisted taking the position before I finally agreed to give it a try. I discovered something I love: the repeated process of painting with others and coaching them through their own self-doubts. It has made my own painting and interpersonal skills sharper.
Opening myself up to new creative endeavors and persevering in the face of insecurities has changed my life. My mission is to encourage people to do those things they have always wanted to do and to fight the anxieties that hold us back.
We’d love to hear the story of how you turned a side-hustle into a something much bigger.
I started teaching painting parties as a part time job in 2013 at Hook Gallery in Westport. In 2014 I got a chance to open my own small location in the Crossroads, and this became known as Happy Trees Painting. I continued to teach occasionally for the Hook, in addition to the classes I was offering in the Crossroads.
I also worked during the day as a server at a local restaurant. When business was slow, I could get out my laptop and work on communications with customers and marketing for Happy Trees. I ran my business in the Crossroads for a couple of years before I ended up moving to the West Bottoms. I now offer classes both in the West Bottoms, as well as Hook Gallery, and have a small staff of instructors to help me out. Happy Trees is still a small business, but I have been able to do it as a full time job for the past eight years. My salary those 8 years may not be a desirable number to some, but I think if I had given it up for a bigger paycheck my creative growth would have suffered. Being in control of your own time is an investment in itself and I am constantly reminding myself of that.
Can you talk to us about how your funded your business?
When I started Happy Trees it was a slow but steady pace. If I had a big month I would invest in more easels or aprons. Eventually I had enough supplies that I could handle larger classes. I would always be thinking of new ideas for paintings to offer as examples and over several years created over 100+ designs.
I didn’t have money in the budget for a website until I had been in business for 5 years. Until that point social media, Groupon, and word of mouth were the ways I advertised. The other way I kept costs low was to teach out of shared spaces. It takes some coordinating, but it is worth it, and I have always enjoyed having studio mates.
Letting the business build over several years and not having a high overhead allowed me to approach growth in a natural debt free way. There are all kinds of ways to start a business and I don’t think other ways are wrong. There is a thinking sometimes of needing to have “this” before you can have “that” and that prevents us from starting simply with what we have.
Contact Info:
- Website: happytreespainting.com
- Instagram: happytreespainting
- Facebook: https://www.facebook.com/happytreesbyobpaintingco
- Youtube: https://www.youtube.com/@happytreespainting2455/featured
Image Credits
Photo credit to Zach Bauman and Morgan Miller