Interested in starting your own entrepreneurial journey in photography but unsure what to expect? Then read up on our interview with Kasey Levine Hilleary, Founder & Creative Director of KLH Photography LLC, located in Trumbull, USA.

What's your business, and who are your customers?

I'm a professional photographer specializing in headshots for actors, models, performers, business owners, and business professionals.

Tell us about yourself

I'm a picture taker. Whenever my family and I would go anywhere, I'd be the one capturing the moments. So one year, my husband bought me a "grown-up" camera, and I just had to learn everything about it. "What does this wheel do?" "What is an aperture?" "Shutter speed, what's that?" I went to school to learn everything technical and then studied with some top photographers on posing, marketing and business. After trying several genres, I found I fell in love with capturing compelling headshots of people. I love putting people at ease, getting to know new people, and showing them they actually CAN take a good picture. "I'm not photogenic" is not a thing.

What's your biggest accomplishment as a business owner?

I feel like my biggest accomplishment is how I've developed the ability to make every client that walks into my studio feel comfortable and be seen. Nobody - except maybe actors and models - skips into my studio excited to be photographed. However, by the end of every session, my clients typically say something like, "That was fun. I felt so comfortable." I love that. I love making people feel good about themselves in the 30 minutes to an hour I'm with them.

What's one of the hardest things that comes with being a business owner?

Marketing myself. I spend very little time wearing that marketing hat. They say if you want 10 clients, you need to get in front of 100 people. That takes a lot of work and takes me away from my camera. Yuck.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Get a great headshot (call me). People want to know who you are, and a picture says a lot. Make sure the photographer you hire can capture YOU with connection, good lighting, and a great genuine expression.
  2. You have to put on the marketing hat every day to attract customers. Come up with a marketing plan for every quarter of the year.
  3. Make sure you value your work so you can price yourself at a sustainable level, especially when the product is you. This is sometimes the hardest thing to do, but know that you deserve it!

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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