Unprepared and Overconfident!
Unprepared and Overconfident is the ultimate hangout with Dan and Trent! Join us as we dive into conversations with fun guests, explore music, comedy, and whatever else comes to mind. We’re all about having a great time and letting the conversation flow naturally. No scripts, no pressure—just real talk, unexpected laughs, and whatever happens next.
Episodes

Tuesday Sep 30, 2025
Tuesday Sep 30, 2025
In episode 9 of Unprepared and Overconfident, Dan and Trent welcome the one and only RJ Dupree, aka “The Doop Show.” As a TV personality, baseball player, and poker dealer, RJ brings a unique flair to the conversation. Join them as they explore the worlds of baseball, poker, and modern dating, with plenty of laughs and unexpected tangents along the way.

Tuesday Sep 23, 2025
Tuesday Sep 23, 2025
This week on Unprepared and Overconfident, Dan and Trent welcome the one and only Brandon Jones! A poker enthusiast with a mission to taste every bourbon out there, Brandon brings his charm and wit to the table. Join us as we dive into fun poker tales, bourbon adventures, and the heartfelt story of the saddest day of his life. It’s a rollercoaster of laughs, deep moments, and plenty of surprises!

Tuesday Sep 16, 2025
Tuesday Sep 16, 2025
“In this episode of ‘Unprepared and Overconfident’ with Dan and Trent, we sit down with Karen Carrillo, the Blue-Haired Social Worker. We explore the world of therapy, her nonprofit endeavors, and even a dash of stand-up comedy, all in a fun and lighthearted chat!”

Monday Sep 08, 2025
Monday Sep 08, 2025
Send us a textGet ready for a bear-y entertaining episode 6 of ‘Unprepared and Overconfident’ with Dan and Trent! This week, we’re joined by the fabulous April Gill. We’re sharing some hilarious jury duty stories, a sprinkle of court cases, and a Un-bear-ably hilarious tale of a man saving a drowning bear. What was the bear thinking? Well, you’ll find out, especially with Dan in his bear suit! It’s a fur-tastic episode full of laughs and surprises—don’t miss it!”

Tuesday Sep 02, 2025
Tuesday Sep 02, 2025
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Join Dan and Trent for a chat with hilarious Angela Owens! In this episode, Angela shares her comedy styles, spills some behind-the-scenes secrets, and recounts her recent show in Scotland. It's a delightful mix of laughs, stories, and good vibes. Don't miss out on this fun chit-chat!

Tuesday Aug 26, 2025
Tuesday Aug 26, 2025
Send us a text“Brace yourself for a hilariously unpredictable episode of ‘Unprepared and Overconfident’ with Dan and Trent! This week, they’re joined by Jack Morrison from ‘Megan and Jack,’ and things are bound to get delightfully off the rails! Expect a mix of witty banter, behind-the-scenes insights, and plenty of laughs. It’s a podcast episode that’s sure to be a ‘Jack’ of all trades and a master of fun!”

Wednesday Aug 20, 2025
Wednesday Aug 20, 2025
Send us a textIn this episode of “Unprepared and Overconfident,” Dan and Trent dive into the world of movies and poker, all while having a blast and keeping it light. Get ready for some fun and unpredictable moments!

Monday Aug 11, 2025
Monday Aug 11, 2025
Send us a textJoin Dan and Trent for the second installment of “Unprepared and Overconfident,” where they attempt to redeem themselves after the first episode’s chaos. This time, they dive into some movie talk, sprinkle in a bit of poker strategy, and keep the laughs coming with their signature banter. It’s the perfect blend of fun and randomness—don’t miss it!

Tuesday Aug 05, 2025
Tuesday Aug 05, 2025
Send us a textWelcome to the very first episode of Unprepared and Overconfident. Join Dan and Trent as they dive into a spontaneous jib jab session that quickly goes off the rails. Expect random tangents, plenty of laughs and a sneak peek into the unpredictable fun that awaits in the future episodes. It's a wild ride from the get go, and you won't want to miss a second of it.





