Meet Trey Diller | Event Producer, 18 Wheeler Authority Owner, Real Estate Investor

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

Hi Trey, we’d love to hear more about how you thought about starting your own business?
I like to risk it for the biscuit. You fail at 100% of the things you don’t attempt so why not try and make the most of it when you can during this game of life. I come from an entrepreneur family and know quite a bit of people that work for someone else or a corporate company and most are not happy with their situation as they are only making their boss rich and they are barely able to make it. You get out what you put in with everything in life and hard work always pays off. I prefer to be involved with things I enjoy doing and that make me happy rather than making my pockets fat. My genuine pleasure in life is providing others with a good time and making them smile so that is why I do things that are different and unique that most would not even attempt to do.

Let’s talk shop? Tell us more about your career, what can you share with our community?
I am a former NFL football player that unfortunately went through a handful of surgeries when I got out of college and it prevented me from continuing my career on the football field. When I got done playing football, I had some money saved up and at the time the sneaker game was a thing so I decided to throw a sneaker show called Woodlands Sole Expo at Legends Sports Complex that consisted of 50+ food vendors, live music, food vendors, activities for all ages, and raffles. I made a profit and decided this industry was something I enjoyed because I was entertaining others and giving them something unique and different to be a part of. After Woodlands Sole Expo, I joined forces with a couple of my buddies and produced an event called Beyond the Pines, a country music festival in The Woodlands and had artists like Aaron Watson, Lukas Nelson, Parker Mccollum, and Flatland Cavalry perform. It rained so we lost money and after that my partners no longer wanted to pursue the industry. I did and to this day have produced over 70 festivals with my latest called Big as Texas held at the Montgomery County Fairgrounds to help raise awareness on suicide prevention and mental health. I have a passion for bringing people together and providing them with a good time and that is why I like doing large mass gatherings. Big as Texas was 20 months of 24/7 work but when it came time for the show all of the ducks were lined up and things worked out great for us. Be very strategic on who you go into business with and make sure you hold them accountable depending on how the entity is structured.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
If my friend was coming to The Woodlands area for a week the schedule would be something like this
Monday-Go hit LGND barbell in the morning for a workout. Always gotta start the mornings off with a workout for the physical and mental state. I would take them to Snooze Am for breakfast. Hit the Mall for shopping. Hit market Street. Hit Hughes Landing for dinner. Close out the night at Main Event or Dave N Busters.
Tuesday-Go hit LGND barbell in the morning for a workout. Always gotta start the mornings off with a workout for the physical and mental state. Would hit Another Broken Egg for breakfast. Go visit my father business Woodlands Car Care to show them what he built. Would then go by Pickle ball court and go grab lunch at Corkscrew followed by browsing Old Town Spring where we would then eat dinner. Finish off the night at Blend Bar and smoke a cigar.
Wednesday-Go hit LGND barbell in the morning for a workout. Always gotta start the mornings off with a workout for the physical and mental state. I would take him to Taco Church, a mens group that is my community and it ends at 9a. I would hit Dosey Doe for breakfast and then head to Houston. Hopefully Astros or Rockets are playing and we would attend one of the games. I would go to Post HTX for lunch and then go hit Galleria Mall until dinner time where I would want to go to Houstons for dinner before the sporting event.
Thursday-Go hit LGND barbell in the morning for a workout. Always gotta start the mornings off with a workout for the physical and mental state. I would take my friend to Huntsville to show them the Sam Houston campus where I went to college and then grab lunch at Humphreys or Farmhouse. Would stop in Conroe on the way home and hit Pappas on the Lake for dinner and hanging out before heading home for the night.
Friday-Go hit LGND barbell in the morning for a workout. Always gotta start the mornings off with a workout for the physical and mental state. We would hit Brookly Bagel for breakfast and then I would want to play a round of golf at one of the many courses here in town. Would eat lunch on the course and then spend some time in the sauna/hot tub before going to dinner at Federal American Grill. Would go to Cinemark for a movie and then maybe make a stop at Kirby Ice House to show them the night life.
Saturday-Go hit LGND barbell in the morning for a workout. Always gotta start the mornings off with a workout for the physical and mental state. Go hit all of the farmers markets in the morning and shop local. Would go visit Copendero and shoot some guns and have lunch there. After that we would go drive around the Woodlands and show him all of the real estate, shopping, and things to do. Would have dinner at Republic Grille and close out the night with Midnight Cravingz.
Sunday-Go hit LGND barbell in the morning for a workout. Always gotta start the mornings off with a workout for the physical and mental state. Would go hit church in the morning and then go grab brunch at Baja Cantina considering I was one of the founders of the restaurant on the Waterway. Would then go for a walk around the mal ring, waterway and from there take him to the airport to get him out of here after a long eventful week.

Who else deserves some credit and recognition?
I used to have an entourage everywhere I went but as I got 0lder and started to realize most were just riding coat tail and along for the ride, my circle got smaller and most of my “friends” became distant. You are who you surround yourself with and at this point in my life I value my mentors and community as well as my family as the most valuable friends in my life. I have a small men’s group that is called Taco Church where every Wednesday morning we meet at Abundant Harvest and it consists of 10-20 men that sit around at a table and discuss scripture and also life’s obstacles and how to overcome. It is a room where nobody will judge you or look at you cross eyed when you bring up some of the issues you might be dealing with and they will give you the exact guidance, good or bad, on how to overcome the obstacle and get yourself in a better place. Community is everything and if you have the right community to lean on, anything is possible to learn from.

Website: https://inspireprod.com

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