The Art Biz ep. 44: A Live Painting Business with Jennie Tucker

In 2014 then-promising artist Jennie Tucker received a challenge out of the blue from a friend: Paint my wedding. At my wedding. In front of all the guests.

Most of the artists I know and love would have (1) laughed out loud thinking, Obviously she jests, or (2) run the other way. Fast.

Not Jennie. She accepted the challenge and rose to the occasion.

More interestingly, she found she really liked it.

Jennie Lou live painting in Dallas, Texas. @linejergunsen – Caroline Jergunsen Photography.

Jennie, who was single at the time (read: freer), enjoyed traveling and painting at weddings. She liked interacting with guests and painting within the time and location constraints. She didn't mind people looking over her shoulder to see what was on the canvas.

She became an artist-performer of sorts, and the word spread.

Jennie found a niche for herself: a live painting business. Before long, she was in demand for other live events, like corporate parties and conferences.

The opportunities abounded. Every one of them happened by word of mouth and, eventually, as a result of her social media sharing.

There was no way she could accept all of the invitations that came her way. She had to start saying No.

In this latest episode of the Art Biz Podcast, I asked Jennie Tucker about the business side of live painting. We discuss the importance of contracts (and what to include in them), dealing with people and their many personality quirks, income streams, and her desire to help more artists start doing this work.

Jennie openly shares the challenges and a somewhat embarrassing story from a most memorable wedding.

Listen Now

Music by Wildermiss.

©Jennie Tucker – Jennie Lou Art, Live Wedding Painting. Acrylic on Canvas. 24 x 36 inches. Used with permission.


  • Jennie's background in graphic design and teaching. (2:00)
  • How Jennie painted as a hobby and sold undervalued work to friends and family. (3:00)
  • Jennie's first experience with live painting at a friend's wedding. (3:45)
  • Her leap to creating a business around her art, starting with a website and business cards. (5:40)
  • When Jennie first realized she could build a lifelong career as an artist. (6:50)
  • Why live painting interested her and the reaction her first demonstration received. (7:40)
  • How Jennie feels like Teach for America prepared her to take chances and learn through trial and error. (9:30)
  • How she defines live painting and what it entails. (11:20)
  • Jennie's role as a performer and how that influences her dress choices and more. (14:20)
  • The step-by-step process for booking the live events with clients, including the value of her website rankings. (16:40)
  • Jennie's pricing model and contract. (19:00)
  • The demand for live painting and how far in advance she books events. (22:00)
  • What Jennie wishes she would have known earlier including, “People are not going to value your time and your talent as much as you are.” (25:00)
  • Jennie's favorite part of live painting and how it fuels her passion for connection and art education. (27:10)
  • The most challenging part of live painting and how she deals with this. (30:50)
  • How Jennie stays organized and the “imperfect” systems she uses. (34:20)
  • Jennie's advice about staying calm when things go wrong. (39:10)
  • Her income streams. (39:50)
  • Jennie's warning not to take things personally. (42:30)
  • The workshops she's leading for artists looking to get into live painting and her heart for helping others in the industry. (43:10)


Emily Jeffords, artist
HoneyBook bookkeeping software
Dorothy Collier's Positively Creative Podcast
Teach for America

About My Guest

Jennie Lou at work during a wedding in Houston, Texas. Joseph West Photography.

Originally born and raised in Austin, Texas, self-proclaimed people person and extrovert Jennie (Pitts) Tucker grew up embracing a Texas way of life and soaking up the world around her. She graduated from college in 2011 from Baylor University with a BFA in graphic design. After graduation, she got a job with Teach for America in South Carolina to teach world history to 6th graders in a rural community.

In 2014, Jennie moved to Boulder, Colorado for new experiences—the mountain town and her odd jobs at a foster home and as a barista, nanny, Young Life volunteer, and eventually a pediatric orthodontic assistant (after meeting an orthodontist on an airplane). That spring, Jennie was encouraged by friends and family to start her own art business, and it was not long before she was doing it full time. She specializes in live event painting and custom artwork.

Follow her on Instagram @jennielouart.


Music by Wildermiss.

This episode is sponsored my signature business-building program, the Art Career Success System.

All of the lessons you learn in the Art Career Success System are tasks you will do over and over again throughout your art business and career. That’s why it’s a SYSTEM.

In the ACSS you will build a strong foundation using my video and audio lessons, worksheets, and transcripts. And you will be part of a community of artists who are forward-thinking and forward-moving.

Follow your ambitions and join us now

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