We were lucky to catch up with Derek Diamond recently and have shared our conversation below.
Alright, Derek thanks for taking the time to share your stories and insights with us today. When did you first know you wanted to pursue a creative/artistic path professionally?
I’m an only child, so I had to find ways to entertain myself growing up. The primary way to do so became watching movies and TV shows. I can still remember watching the original “Star Wars” movie at my uncle’s house like it was yesterday. Before the movie, a behind the scenes feature explained some of the aspects of how the movie was made. From there, I was hooked. Once the internet grew (I was born in 1986, so I can still remember the internet in its infancy) I began to follow the process of how movies and shows are made. But never considered it as a career.
As I was completing my freshmen year of college, I still had no clue about what I wanted to do with my life.
At the time, I was a member of my college’s Student Government Association. One day, I found a brochure in the SGA office advertising a Digital Video/Broadcasting degree. After reading it, I sat it down and didn’t give it much thought. Then I read it again. And again. After reading it for a third time, I decided to try it for a semester. After my first TV Production class, I knew that this was the career path I wanted to take. Since then I’ve created numerous videos that cover a wide range of topics, including minor league baseball, weddings, and more.

Derek, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I’m a filmmaker and podcaster based out of Pensacola, Florida with 16 years of video experience.
I run my own production company called Anchor of Reality Productions and we specialize in film production and wedding videography. I started wedding videography in 2008 simply because I was desperate for money. Little did I know that it would become an important part of my professional life.
When it comes to film production, I enjoy the entire process but my favorite is the challenge of producing. I also enjoy the collaboration with brides and grooms as we work together to craft the capturing of their special day.
In 2017, my friend and fellow filmmaker Stephen Wise gave me the opportunity to work on set of “Sur’vi”, his award-winning short film that was made in Pensacola. This reignited my passion for filmmaking, and a year later I wrote and directed my first short film called “The Parker Syndrome.” After many personal and professional changes in my life, I returned to filmmaking in 2022 with “The Feature”, which is a short film influenced by some of the changes that I previously mentioned.
My most proud accomplishment has to be watching “The Feature” with my wife at the TCL Chinese Theater in Los Angeles. To see something that everyone involved worked so hard to make a reality play at the most famous theater in the world is an experience I’ll never forget.

Any resources you can share with us that might be helpful to other creatives?
I wish I had the confidence to ask questions and attempt to get more hands-on experience early in my creative journey. When I was a teenager, I developed a severe social anxiety that made my high school and college years a challenge.
I specifically remember taking Public Speaking in my freshmen year of college. On the first day of class, we had to deliver an impromptu icebreaker speech. I was so afraid to speak in front of a crowd that I cried.
My lack of confidence led me to missing out on opportunities that were offered to me, including going to film school. I’ll always consider myself a work in progress, but I think

For you, what’s the most rewarding aspect of being a creative?
Obviously seeing the final product, but one of the most rewarding aspects to me is the collaboration and learning experiences you gain along the way. I’ve been fortunate to work with some incredible people in every phase of my career, and I’ve learned something from all of them that I continue to carry with me to this day.
One of those people happens to be my wife Samantha Owens Diamond, who helped me polish the script for “The Feature” and also edited the film. Despite never having edited anything before, she completed the first cut of the film in two days! And now she’ll be directing her first short film, “Plain Jane”, this summer. She inspires me to be better every day and I’m glad that we get to share this journey together.
Contact Info:
- Instagram: https://instagram.com/ddiamondfilm
- Facebook: https://www.facebook.com/Derek.D.Diamond/
- Linkedin: https://www.linkedin.com/in/derek-diamond-66b748a8/
- Twitter: https://twitter.com/Derek_Diamond
- Youtube: https://www.youtube.com/@derek_diamond
- Other: My short films are available to watch on YouTube (My latest film, “The Feature,” will be available on June 11):
https://www.youtube.com/@anchorofrealityproductionsMy podcasts can be found here:
https://linktree.com/reelwisdompod
https://linktr.ee/nerdcaveretro




