We had the good fortune of connecting with Chris Gillett and we’ve shared our conversation below.

Hi Chris, can you walk us through the thought-process of starting your business?
I had been a trial lawyer for almost two decades but never really enjoyed it. It was a good living, and I worked with some great people, but my heart was never in it. It never felt like a great fit for my abilities. It’s a long story, but I got into headshots and did it as a side hustle for a while. At some point, I turned around and realized I was doing something in town that nobody else was doing. My thought process was “hey, maybe I can do this instead of the law thing and be able to pay my bills and be happy.“ A decade later here I am earning a good living and happier than ever.

Alright, so let’s move onto what keeps you busy professionally?
Expressions and making people look their best. It’s crazy that in 2025 headshot photographers still seem to be generally poor at helping their clients with expressions and looking their best. The industry is still full of “turn this way, smile, <click>.” When I was a lawyer and getting crappy headshots, I never imagined that it would get any better than that. I figured that’s what I look like and that’s what I got. When I finally did the right stuff in front of the camera and lit myself properly, it changed how I felt about myself. It was like “OK I don’t look like Clooney, but I look pretty fucking good. I should be happy with this.“And I was. It changed how I felt about myself. It brought my self acceptance gap to a manageable point. I love doing that for other people now.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I’m old so don’t get too excited, but here it is: if they’re from out of town, we have to go to NASA. Then that evening hit a steak joint like steak 48 or Turner‘s and then drinks afterward at a speakeasy like Emelia‘s Havana.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
There are so many people. I could certainly think my family for putting up with me. The truth, however, is that I get great clients. Super exceptional and successful people. I’ve never been happier than I am now, and it’s these great people that make it possible.

Website: LikeTheRazor.com

Instagram: 6illett

Linkedin: Gillett

Facebook: LikeTheRazor

Image Credits
S. Christopher Gillett

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