BTU #52 - Chris Pestel: Army to Photographer with ESPN, Playboy and more


iTunes | Stitcher | View Transcript

“From the process of going through West Point and then being an officer and then deciding where you're going to next, one of the first things that is told to you is that you can go do whatever you want; you can write your own path. I think I took that to heart. If I can do whatever I want, this is what I want to do. It was a thing where I picked up a camera and started photographing a few things, and really, really enjoyed it. It was very intuitive and I liked that. It was the closest thing I had found to playing sports, where I was building muscle memory and then let that instinctive ability take over and get lost in the flow of what's going on. And I really wanted to keep doing that - if I got to choose what I would do, that's what I wanted to do. Then just dove neck deep in it and tried to figure it out."– Chris Pestel

Chris Pestel is the Founder of Pestel Photography, and has worked as a freelance photographer for ESPN for nearly 9 years now. He started out at West Point after which he served as an Army Officer for five years. After his transition he started out as a photographer at Carolina Sports, before moving on to Playboy Enterprises as a Junior Designer & Photo Editor. He’s also served as the Director of Public Relations for his high school alma matter, Montini Catholic. Chris has run his company - Pestel Photography - for over 9 years, making him on the verge of the 4% of entrepreneurs who keep their company running for 10 years.

The top four reasons to listen to this episode are:

  1. Courage - Chris left the Army to become a photographer. I found it difficult to dive into entrepreneurship and that was from business school, in the bay area where startups are very normal. Chris, on the other hand, took a leap of faith to follow his passion. Initially, he had to tell people to ignore his background and education in order to consider him for jobs for which he seemed overqualified. And it worked. He owns his own company and has worked with both PlayBoy and ESPN.
  2. Do what you know - there was no roadmap for Chris. He talks about how he took baby steps to start with what he knew, and then work tirelessly to fill in the gaps
  3. Craft - Chris is a case study in honing one’s craft. He talks about it in a way that could benefit a listener in any industry - how he immersed himself, surrounded himself with a community, researched in the library, and more.
  4. Don’t panic - Chris went from earning $75k / year in the Army to $19k / year. He talks about making sacrifices to get to where you want to go, and the difference between patience and panic.

Our Sponsor

Audible is offering one FREE audio book to Beyond the Uniform listeners. You can claim this offer here, and see a list of books recommended by my guests at

Selected Links

Show Notes

  • 2:45 - Chris' background
  • 3:28 - Chris' decision to leave the Army
  • 4:35 - How Chris got his start with photography
  • 6:20 - How Chris decided to start a career in photography
  • 8:10 - How Chris found his first job in photography with Carolina Sports
  • 10:57 - What Chris' day-to-day life looked like at his first job with Carolina Sports
  • 13:30 - How Chris trained and improved himself as a photographer
  • 14:58 - Specific resources Chris would recommend to other aspiring photographers
  • 19:32 - How Chris transitioned from Carolina Sports to Playboy
  • 27:39 - What day-to-day life was like at Playboy
  • 30:00 - How Chris approached the opportunity at Playboy
  • 32:50 - How Chris' approaches mentors and role models as an artist
  • 37:12 - How Chris founded his own company, Pestel Photography
  • 40:31 - How Chris got started with ESPN
  • 43:24 - In what ways Chris' military service has helped him and in what ways he's had to break habits
  • 49:34 - If Chris could give advice to himself when he separated from the military, the one piece of advice he'd give to himself
  • 53:39 - Final words of wisdom