Episode 89 - Davin Gentry: It Takes A Lot Of Bumps And Bruises

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Davin Gentry is a creator and artist who is the co-founder behind both Premium Co and Diet Starts Monday. Even with seeing himself on a billboard in Los Angeles, having hundreds of people waiting outside of his store or taking pictures with fans, it all feels natural to him because he feels he’s doing what he’s supposed to be doing at the time he’s supposed to be doing it.

Growing up in Madisonville, Kentucky he was embarrassed as a kid to admit he lived in a trailer park with his mother and would get dropped off blocks away so his friends wouldn’t know. One of his early passion was basketball which was what kept him focused and out of the streets. Finishing up high school he attended community college for a year and a half and then transferred to Western Kentucky and majored in Advertising. After graduating he sold hand painted shirts for six years until he and Tyler Hundley got Premium Co off the ground in 2011.

A text conversation with designer John Geiger about only working out in order to fit into designer clothes led to the launch of their clothing line Diet Starts Monday in 2017. Incorporating the idea of procrastinating diets, they launched what was planned to be a 3 month pop-up event that turned into a full year round operating restaurant and retail space in Washington D.C. With a recent collaboration with Five Four, they’re just getting warmed up with what has yet to come for the brand.

In this episode Davin discusses the balance of making what we want and what the customer is looking for, building the right relationships sets us up for a promising future, his definition of success is being financially stable enough to create what he wants, recognizing that some things are completely out of our control, his day-to-day routines and appreciating all the bumps and bruises that have helped get him to where he is today.  


Podcast Outline (Time Markers For Audio Version Only)

  • Davin Gentry is a creator / artist who runs both clothing lines Diet Starts Monday and Premium Co

  • Growing up in Madisonville, Kentucky. Was embarrassed to tell friends he lived in a trailer park (5:35)

  • Spent 8 months in court after being charged with assault on a police officer + resisting arrest (7:50)

  • Father was in / out of most of his childhood. Didn’t get along with step-father (16:30)

  • Basketball kept him focused: “You eithered play ball or you were in the streets” (19:15)

  • Went to community college then to Western Kentucky for advertising (20:00)

  • Hand painted shirts for six years after graduating, was living full-time as an entrepreneur (22:10)

  • Working at a community center for kids teaching how to paint shirts (25:15)  

  • 2011 co-founded Premium Co with Tyler Hundley selling necklaces/bracelets with gemstones + precious medals (28:15)

  • The biggest turning point for Premium Co was the Perseus Tee (36:15)

  • Balance of making what we want and what the customer is looking for (43:40)

  • Meeting designer John Geiger in 2013 and wanting to start a brand together, they launched Diet Starts Monday in 2017 (48:55)

  • Held a private launch party at the Cosmo in Las Vegas for D.S.M. (54:45)

  • Building the right relationships (57:40)

  • A 3 month pop-up event of a restaurant/retail space “Come For The Clothes, Stay For The Food”  turned into much more (60:20)

  • Having a billboard on the cross streets of Fairfax and Melrose to promote collab with Five Four (63:45)

  • Getting blacklisted from Agenda Show (66:20)

  • Biggest lesson learned from John Geiger is to be confident in yourself (71:00)

  • Davin’s definition of success: Financially stable enough to create what he wants (76:00)

  • Creating the way I’m supposed to be creating at the time i’m supposed to be doing it (81:20)

  • Day - to - day routines include gym, eating clean, mediating etc (84:25)

  • Some things are out of your control (91:30)

  • Davin’s purpose is to create something that is exciting for people and also create a way to help facilitate places that don’t have it (95:25)

  • Ask Bobbay 1 question: What’re your routines / Since being in LA, have you felt yourself slipping away? (101:40)

  • Drama’s podcast Short Story Long and Devin’s career has a synergy (107:50)

  • Picture frame 10 years from now: Surrounded by his friends, girlfriend, dog Louie and a gallery of his work (111:45)

  • Find Davin on social media

  • Advice for find a passion/purpose (119:20)

    • Try different things

    • You aren’t supposed to have the perfect plan

    • Everything you’ve been through gets you ready for the moment when it comes