Caricature Artist Julia Kelly on Art, Business, and Bookkeeping (e011)

Listen to this episode of Hacker Practice on iTunes.

Julia Kelly and Justus in the Cayman Islands

Do you know somebody who loves to argue?

I’m one of those people. So is Julia Kelly.

We’re great together.

Julia is the most renowned caricature artist west of the Mississippi. She built her business from scratch and is currently starting business #2.

I guess I caught her at a good time.

When I asked her to do an interview with me. She made an interesting request: “Let’s wing it!”

She’s been on some pretty awesome podcasts including: Entrepreneur on Fire, Double your Freelancing, and Afford Anything. She says: the less scripted the show, the more fun the interview.

My old college buddies would agree: Justus loves “doing it live”. So I agreed to do the episode with ZERO PREPARATION.

Typically I prepare for interviews with rigorous research and outline a list of topics to talk about. In this case I did no such thing. Shoot, I didn’t even take notes until after we recorded the conversation.

The result was a fascinating conversations that covers art, business and everything in between. Enjoy 😀

[00:00] This is an unconventional episode. Julia explains why.

[01:55] How Julia introduces herself as

  • A Bookkeeper
  • A Caricature Artist

[4:30] How to be a success without trying very hard

  • Morning rituals and meditation are for the birds
  • How to be successful without them: Show up, do good work, and keep your word.

Sine qua non noun

  1. an essential condition; a thing that is absolutely necessary.

[07:00] Some ways Julia and Justus are different

[10:00] Why Julia is moving into the bookkeeping business

  • Recurring revenue, predictability, stability
  • Partnership

[13:30] Julia shoots down the concept of “following your passion”

  • It’s a fleeting feeling

[16:00] How Julia developed the craft of caricature art

  • Time on task is the most important aspect of developing artistic ability
  • Got a job at LEGO Land
  • The job had a 6-hour training program where everything was done in a marker
  • No erasing
  • Don’t be a perfectionist (“If it’s 80% good, ship it!”)

[24:00] Julia’s and Justus’ artistic influences

Julia Kelly’s Bust of JRR Tolkien

[32:30] The story of the Captain’s hat and lessons Justus learned from an experiment in fame

  • Fame is cheap
  • Anonymity is priceless

[37:30] Julia’s struggles with identifying her strengths

[40:30] Julia’s friend who knows Tom Cruise

  • Confidence is extremely valuable.
  • Fake it ‘til you make it

[42:30] Julia’s story getting started freelancing

  • Market focus made all the difference

[45:30] Selling to trade show marketers

  • Tracking ROI is important
  • “Connect what you do to the outcomes they want.”
  • Attract traffic
  • Create follow-up opportunities
  • Create the right marketing language and identify with their needs
  • Get one customer and drill them for what sold them
  • Get feedback to improve (Peter Dunbar echoed this in episode 8)

[53:30] What lessons from caricature art transfer to bookkeeping

  • Pricing for bookkeeping is more custom, so don’t advertise fixed prices
  • Longer sales cycle for bookkeeping

[56:30] Successes and failures in bookkeeping

  • 3 client since August
  • Cold email works!

[57:30] How to cold email effectively using LinkedIn

  • Julia sends 70 canned emails a day
  • The 556th email hit!

[1:00:00] Justus tells a story about canned cold emails that worked on him

  • Follow up 4 times!
  • Follow up again!

Yet Another Mail Merge Google Sheets Extension

[1:04:00] Julia’ Bookkeeping goals and differentiating factors

  • 7 figure business
  • Totally remote
  • Flat monthly fees

[1:05:45] Julia’s ideal client is hands-off, casual, comfortable with remote bookkeeping, and wears plaid

  • Rapidly growing startups are a good fit in many cases

[1:08:30] Julia wants everyone to go read Slatestarcodex and talk to her about it.

Check Julia out at

Also, Julia thinks GMO’s are safe. That is all.

What else?

That’s all. Actually, wait, no. Go to iTunes and subscribe to the show. And leave us a review 😀

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