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Julia Kelly: “You’ll end up surprising yourself”

You’re not too good to delegate. I wish I had started delegating much sooner than I did. I had the classic “no one can do this job as well as me” mindset that’s very common with business owners. Get over that as fast as you can. Your time doesn’t scale and neither will your business […]


You’re not too good to delegate. I wish I had started delegating much sooner than I did. I had the classic “no one can do this job as well as me” mindset that’s very common with business owners. Get over that as fast as you can. Your time doesn’t scale and neither will your business until you learn to delegate.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Julia Kelly — Founder of JK Expressions and co-founder of Rigits. JK Expressions provides live digital caricature artists to corporate events and celebrations. Rigits helps startups and small businesses with bookkeeping, accounting, and tax services.


Thank you so much for doing this with us Julia! Can you tell us a bit about your “childhood backstory”?

I’ve always been both a right and left brained person. I’ve been drawing ever since I can remember. I actually wanted to be a caricature artist when I grew up. My parents would take me to amusement parks and instead of going on rides, all I wanted to do was watch the caricature artists work and pepper them with questions.

But I had an analytical side as well. I interned at a nonprofit while in high school, doing filing and other administrative tasks, and I loved it. I always wanted to be busy, whether it was with art or other types of work.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

My first foray into making money from caricatures was when I got a job as a caricature artist at an amusement park here in San Diego while in college. I didn’t think it would turn into a business at the time. I just wanted to get paid to do what I loved and improve at drawing caricatures. I realized at the first day on the job that there’s a huge difference between drawing a caricature in the comfort of your own home with no time constraints, and drawing a live person while other people watch! It took a couple months before I was comfortable (and fast) at drawing live caricatures.

After working at the park for one summer, I started doing gigs on the side, mostly weddings and birthday parties. After my first couple gigs, I realized that there was a real business potential here. I became more strategic and systematic with my marketing efforts, invested in equipment to do digital caricatures, and eventually hired other artists and expanded into other cities and states.

I did all of this while completing my degree in accounting from San Diego State. The flexibility of running the caricature business made it the perfect fit for me while in college. I would do a bunch of gigs during summer break, and during the spring and fall semesters I would delegate more to the other artists on my team. My original plan was to intern at one of the Big Four accounting firms, then sit for the CPA exam and get a “real job” in accounting. However, by the time I graduated I was making more money doing caricatures that I would have as a first-year CPA candidate. I decided to go full time with my caricature business, JK Expressions.

I ran JK Expressions fulltime for a year after graduating. During that year I realized that while I loved to draw, I was missing the analytical challenges that I had while I was in school. I also missed the camaraderie of having classmates and co-workers. And while JK Expressions was doing well, there was no recurring revenue built into the business, which made it hard to scale to the level that I wanted.

I needed a new challenge, and the perfect opportunity fell into my lap when I was having dinner with my friend (now business partner) Elizabeth and her husband. She was employed as an accounting manager at another company and she wanted to start her own business. She had the domain expertise in accounting and I had experience in business development, so a couple weeks later we put together a business plan and our bookkeeping and our accounting firm Rigits was born!

Our first client was a friend of ours whose bookkeeper was taking another job. Within six months, we had enough clients for Elizabeth to quit her job and go full time with Rigits. Three years later we have over fifty clients and five employees.

I still run JK Expressions, though the day-to-day administrative and booking tasks are handled by my wonderful assistant. Now I get the balance between my left and right brain that I needed. I still get to be creative and draw caricatures, and I get to handle the analytical bookkeeping and accounting challenges which I love.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

For both companies I founded, I had full confidence that these were services that people were willing to pay for. Knowing that there was an existing market with willing customers gave me the confidence to turn it into a business. I would never start a business in a market where I had to educate my customers on what I’m selling: that’s a very expensive (and time-consuming) problem to solve. If lots of other competitors are in your space, that’s a great sign. It means the market can support you and all you have to do is figure out a way to stand out.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Get comfortable with selling and marketing. A great product or service is not enough to get a business off the ground — you also have to get in front of people and convince them to buy from you. If you’re not able to sell, your business won’t go anywhere.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I’m lucky that I get to participate in two completely different activities between Rigits and JK Expressions. On any given day I could be deep in spreadsheets and Excel formulas or in front of dozens (sometimes hundreds) of people making them laugh. The balance between the two keeps me fresh. I’m never bored!

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I love solving problems for my clients. Whether its wowing guests at a wedding with digital caricatures, or cleaning up a messy set of books — there’s so much satisfaction that comes from getting paid to make people’s lives better in a tangible way. I also love that we’re able to make our particular values the priorities of our company.

One of the major downsides to running JK Expressions by myself was lack of accountability and community. When it was just me, there was no one to keep me accountable and many times that meant my lazy side getting the upper hand (sleeping late, knocking off work early, getting easily distracted). I also dealt with feeling lonely and isolated as the only one who had skin in the game of my business. But starting Rigits with a business partner solved that problem; I have someone to keep me accountable, bounce ideas off of, and someone to talk to when I’m stuck on a challenge. The difference has been massive. I get so much energy from working together with Elizabeth and our awesome employees.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

That’s an interesting question. I never really had any set expectations about what either job would be like on a day-to-day basis. Both businesses grew organically and I didn’t know what the end would look like going into them.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

I felt that way about eight or nine months after graduating and running JK Expressions full-time. The work just wasn’t challenging enough. I had a lot of free time that I wasn’t used to having, and I missed working in a team. I knew I could grow JK Expressions bigger by expanding into other entertainment services and hiring lots more people, but I didn’t want to run an agency-type business. I felt stunted in my growth and I began to wonder if I was really cut out to be a business owner. It wasn’t until Elizabeth and I began to start talking about our own accounting firm that I saw a way out of that plateau.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was still pretty green at selling and I wasn’t confident in my pricing, I grossly undercharged for live caricature events. I once charged a client $100 total to draw at her party for two hours when the drive to her house was 90 miles round-trip! My rate after factoring in setup time and travel time was less than $20 per hour. After that gig I wised up, doubled my prices and stopped negotiating on price.

Who has inspired or continues to inspire you to be a great leader? Why?

My mom has always been a huge inspiration to me. She founded a clinic in Kathmandu, started and ran several medical groups throughout her career, delivered scores of babies in home deliveries, and raised four kids while somehow maintaining all kinds of creative hobbies. She taught me through example to be courageous, independent and always learning.

How have you used your success to make the world a better place?

The world is a better place because talented and smart people are doing great work consistently for our clients — either by making them laugh with caricatures or making their businesses run smoother with proper bookkeeping, accounting, and tax prep. I’m proud to make the world a better place by contributing a small part to this wonderful system we call the free market.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Get comfortable with being uncomfortable. Running a business will push you out of your comfort zone, a lot. Get comfortable with uncertainty, learning as you go, and not feeling completely in control. That’s the only way to grow.
  2. You’re not too good to delegate. I wish I had started delegating much sooner than I did. I had the classic “no one can do this job as well as me” mindset that’s very common with business owners. Get over that as fast as you can. Your time doesn’t scale and neither will your business until you learn to delegate.
  3. You’ll end up surprising yourself. If you had told me I’d end up with two businesses with over ten employees between them, I’d have run scared and screaming in the other direction. But if you start small and keep learning and iterating, you’ll surprise yourself with what you’re capable of.
  4. Find accountability and community. Running a business is really hard to do alone. Find a tribe — either in or outside of your business — and keep those relationships strong. Having someone on my side who is invested in the success of our business made all the difference for me. Without Elizabeth I probably would have quit being a business owner.
  5. Before you try something new, try doubling down on what’s already working: If you’re not a natural marketer (I’m not), the learning curves on various marketing initiatives can be steep and time-consuming. Of course you should try new things and expand your knowledge base in marketing, but before you try something new, ask yourself if you’ve really optimized what’s already working. Can you double or triple your efforts in an area that’s already proven successful? Try that before you start experimenting.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

A movement that would do the most good for the most amount of people? Whew, I’m not smart enough to do that calculation. However, I think a major problem in our world — one with “out-sized”, terrible effects — is loneliness. We’ve become such an atomized culture, with technology enabling us to go for days or even weeks without having to meaningfully interact with other humans. Problems like the opioid epidemic, school shootings, and online social media ugliness can in large part be traced back to loneliness. I think any movement or individual effort that can penetrate the digital veneer and help real friendships to form is doing massively important work.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“We are what we repeatedly do. Excellence then is not an act, but a habit”. — Will Durant

I’m very motivated by the idea that success is built through thousands of small decisions. I approach my life very methodically — I’m not one to tackle something in a massive burst of creative passion. Instead, I try to appreciate the significance of small decisions and small habits built over time. If I can build the habit of excellence through little habits that nudge me in the right direction, I’ll achieve success in a sustainable way.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I’d love to have lunch with Mark Andreessen. Not because he could give me a bunch of actionable advice (no doubt he could), but I’d just want to pepper him with questions about the future of work, technology, education, everything! He’s a futurist with access to the cutting edge of what’s coming down the pipe in technology, and he’s an optimist which is rare and refreshing. His Twitter feed and podcast interviews are delightful and evocative. I wish he published more!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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