Alright – so today we’ve got the honor of introducing you to Kyle Williams. We think you’ll enjoy our conversation, we’ve shared it below.
Kyle, thanks for taking the time to share your stories with us today What was the most important lesson/experience you had in a job that has helped you as a business owner?
If are present in your job you will always find that you will use your strengths to do the job and those qualities will improve. I worked full time at a chocolate/fudge/ice cream shop when I turned 28 years old. The owners were amazing in that they wanted me to meet certain objectives but overall wanted me to be myself and do the job in how I thought was best. That gave me the opportunity to hone my skills of caring for customers, building a community of employees and finding creative ways to upsell,
It also increased my understanding of finances and how money really works.
Everyone thought I was foolish for taking an ice cream job but it taught me how to run a business that takes care of my employees and make money.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
In 2009, I graduated with a literature and art degree that focused on children’s literature. Upon graduation, I applied to an agency that rejected my portfolio. With one rejection, I thought I should refocus my art and consider fine art. I studied under one of the best plein air painters in my city. It was impactful to my understanding of color but I was bored in painting from observation. I then went back to school to study print making which allowed me to be more experimental in my art making. I was immediately invited for a year long residency where I worked with my graduate professor from MICA. The time was invaluable but after all that time, I did not like working so much time alone, I had no idea how to sell my art, and I wanted to be involved in a career that supports artists. I changed plans and worked full time in a chocolate/fudge/ice cream shop for 5 years where I learned how to run a business and have enough free time to make art. This unassuming job really allowed me to develop into a businessman and develop my compassion in a way that had healthy boundaries.
After five years, it was the beginning of 2021 and I felt done with my job. I quit with no career direction. It was at this time my mom had breakfast with her friend who owned an agency that represented children’s book illustratrators. The lady was ready to retire and wanted to sell her business to someone young who could continue on with it as well as develop it.
The owner told my mom that I would be a perfect fit for the job because of my business and art skills.
I was reluctant about the idea at first but decided that this was the job I had been dreaming to find after all these years. I should also mention that this was the agency I applied to when I first got out of college.
I have been running this agency for three years now. And I can honestly say I have found my dream job (or really, my dream job found me).

Can you talk to us about how your funded your business?
I was working as an employee to an ice cream/ chocolate/fudge shop with a salary that matched that type of job (which means I didn’t get a lot of money). The owners wanted to teach the staff how to gain passive income and they mentioned real estate as an option. So, I had the idea of owning property in my head. One day, I was walking with the owner in a neighborhood that I liked. They said, let’s dream of what house you like. I found a house and they said I should approach the owner about the property. I said, why would I do that when there is no for sale sign. 6 months later that house went on the market, and I put an offer on it. The offer before me declined and I my offer went through. I didn’t have much money so, I rented out bedrooms to help pay for the mortgage and repairs that were needed for this 70 year old house.
A couple years later, I’m walking in the neighborhood, and I see a house that I like, and so I call my real estate agent. I put an offer on the house, and after 6 months of off and on negotiation, I got the house. I was able to rent the house out soon after purchase.
Now, at this time, I rent out both of those houses. The passive income I make from those homes has helped me pay my loan to purchase the business I recently acquired.

Any advice for managing a team?
So, I work with artists who are basically independent contractors. Some time there is a lot of work and sometimes there is not a whole lot of work. I had to pivot the business to focus on where the money is available in our industry. That required artists to bump up their game and see the goal.
What I’ve had to do is spend a lot of energy casting vision. Giving them direction in their own art work. Writing emails that are full of excitement and passion to inspire them to keep building their portfolio. I also made phone calls with the artists to check up on them and see how they are doing.
It all hinges on me, so if I am not excited and believe in the best, neither will my artists.
Contact Info:
- Website: wendylynn.com
- Instagram: wendylynnco
- Linkedin: https://www.linkedin.com/in/kyle-andrew-williams/

