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Kaelyn Query Caldwell leads Kentucky Event Company, an event planning and design firm

January 27, 2026

Please share a brief introduction and tell us something about  your business, Kentucky Event Company:

I’m Kaelyn Query Caldwell, and I started my first business by accident in high school. It grew organically over time, and in 2013, I officially launched my first registered business. My focus is on the hospitality and travel industry. Kentucky Event Company is an event planning, management, and design firm based in Kentucky, serving clients across the U.S. and select cities abroad.

Did you always know you wanted to be an entrepreneur?

No! I got into owning my business by accident and grew it without realizing it. Since my first registered business in 2013, I've opened, closed, sold, and bought many businesses - and even filed bankruptcy for one. And I'm still standing!

Take us back to when you launched Kentucky Event Company? What was your marketing strategy?

It was completely word of mouth. When I realized I'd made enough money to need an EIN, I put a name to the business and started using traditional marketing methods to get the word out.

What accomplishments are you most proud of to date in your business?

Surviving business bankruptcy for one of my companies based on a bad business deal and a bad business partnership. Creating a company culture where our team can thrive in business and in life.

What is one thing you wish you had known when you started your Entreprenista journey?

That at the end of the day, the work comes and goes, but your health is the TOP priority.

When hiring, what is your go-to interview question?

What color best describes you, and why?

What did you do before starting your own business?

I started in this industry through catering, restaurant management, and event planning.

What made you take the leap to start your own business?

I grew my business slowly, not really knowing it was a business at the time. I'd reached the point where I needed to pay taxes and realized that I had a viable business model.

Do you have any recent wins?

We exceeded our revenue goal (Which was already a 20% increase in sales from the prior year) by over 200%, and we broke the million-dollar revenue mark.

What's one app on your phone that you cannot live without?

My project management portal!

Who are Kentucky Event Company customers?

Typically, businesses that host conferences, tradeshows, or meetings/events. We normally work with HR, Marketing, Sales, and the admin departments.

What's your top productivity tip?

Time blocking! It's a game-changer!

What's your favorite business tool?

Basecamp - I have access to all client information in real time.

What's your approach to work-life balance?

I don't believe in "balance" - my life is my work, and my work creates opportunities for a wonderful life. I work hard to carve out time for both. They come in waves - busy season means more work and less "life", and in the slow season, I carve out more time for life than work.

How do you avoid burnout?

Ensuring you spend just as much effort on mental health, mindfulness, self-care, etc.

What advice do you have for aspiring Entreprenistas?

Start small and grow slowly. Work the business as long as you can before hiring employees.

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