We caught up with the brilliant and insightful Amanda Rainear a few weeks ago and have shared our conversation below.
Amanda, appreciate you joining us today. How did you come up with the idea for your business?
I am the Event Manager of Event Painting by Jamie, and I oversee the administrative side of the business. While searching for ideas for our own wedding after we got engaged in 2015, I came across live wedding painting. The idea had not exploded in popularity the way it has today, and I thought this would be a great opportunity for Jamie to explore. He is a classically trained painter, having graduated art school in 2008 and focusing on original paintings in the years following his graduation. At the time I discovered live wedding painting, Jamie was currently painting live full time as an instructor, and I thought this would be the perfect way to evolve what he was already doing. After a lot of brainstorming, we came up with the name “Event Painting by Jamie” and put together a website in late 2015. Just a few hours after putting up the website, we got our first inquiry, from a mom planning her daughter’s wedding and looking for something unique to add to her daughter’s special day. She became our first client, and Jamie painted his first live wedding painting in 2017. In the meantime between our first client’s inquiry and her daughter’s wedding, Jamie began creating wedding paintings from photos for practice. The first wedding painting he created was based on a photo of his brother’s wedding, and that painting resulted in another couple (who had been married at the same venue) commissioning Jamie for a painting based on one of their wedding photos. That painting is still on our business card to this day.


Amanda, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Event Painting by Jamie is a live wedding painting company with two locations in Orlando, FL and Philadelphia, PA. Live wedding painters do just what the service sounds like- they create paintings at weddings live as the wedding is happening. It is a great piece of entertainment for guests to watch the painting come to life, and the painting becomes an heirloom for the couple and their family. Event Painting by Jamie features classically trained fine artist Jamie Pogue, who has been painting professionally for 14 years. Jamie has painted for hundreds of couples and captured hundreds of special moments on canvas. He also paints other events such as corporate gatherings, showers, charity events and more. At Event Painting by Jamie, we pride ourselves on our dedication to the best and quickest customer service support, personal relationships with our couples, and our ability to adapt to events of all shapes and sizes.
Can you talk to us about how your side-hustle turned into something more.
Event Painting by Jamie became a solid side hustle for us shortly after opening the business in late 2015. Event Painting by Jamie went quickly from a side hustle to something more in 2018, when we moved from Philadelphia, PA to Orlando, FL. The demand for live wedding paintings was much higher in Orlando, and it was clear we could scale the business to be our full-time living. Jamie had a full-time office job when we first moved to Orlando, so I became involved in the administrative side of the business in order to help us grow while Jamie continued to work at his office job. We planned to scale the business large enough for it to be full-time for both of us, and we were looking at 2022 for this. Unfortunately, Jamie lost his job in March 2020, moving our schedule up by almost two years. Plus, as we all know, the event industry ground to a halt around the same time. However, we made it work, and Event Painting by Jamie is now a full-time job for both Jamie and myself.



Can you share a story from your journey that illustrates your resilience?
In March 2020, Jamie lost his full-time office job just as the event industry shut down. In order to keep Event Painting by Jamie going, we showed up everywhere we could. This included joining podcasts as guests, completing paintings at networking events to get in front of industry professionals who may not have heard of us, painting at wedding photo shoots in order to meet new venue owners, adapting our marketing strategy to find new engaged couples who were still planning their weddings despite shut downs and so much more. Keeping our name on the radar of other event industry professionals and couples paid off, and word of mouth referrals were high by the time events resumed. We have now cemented Event Painting by Jamie as the leading live wedding painting service in Central Florida.
Contact Info:
- Website: www.eventpaintingbyjamie.com
- Instagram: @eventpaintingbyjamie
- Facebook: www.facebook.com/eventpaintingbyjamie
Image Credits
Image of Jamie and me together- Stephanie Lanni Photo (www.stephanielanniphoto.com) Image of bride pointing at canvas- Sara Purdy Photography (www.sarapurdyphotography.com) Image of Jamie painting with couple blurry in the background- B Rhodes Photo (www.brhodesphoto.com) All other photos are our property.

