Unprepared and Overconfident!

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

January 20, 2026 95 mins

Dan’s on family leave for this one, so it’s just me in the chair with Mitch Lloyd. We talk baseball, swap some movie takes, and just settle into one of those conversations that feels easy and real. No agenda. No rush. Just two guys chopping it up and enjoying the ride.

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In this special musical episode of Unprepared and Overconfident, Dan and Trent take you behind the curtain to share some of the tunes they’ve crafted—whether it’s the intro music that kicks off each episode, fun jingles for their guests, or the quirky surprise chaos card tunes. It’s a little highlight reel of the musical side of the podcast that you’ve never heard before. Plus, a heads-up: Season 2 will be coming back in January, s...

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November 28, 2025 169 mins

In this week’s episode, we’re serving up a hilarious mix of comedy and cough drops! Join us as we chat with the one and only Paul Varghese. We dive into the world of stand-up, share a few movie moments, and even discuss the mighty power of Fisherman’s Friend lozenges. It’s all laid-back fun and good times, so tune in and have a laugh with us!

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In episode 16 of Unprepared and Overconfident, Dan and Trent sit down with Edward Smith—paratrooper, NSA veteran, and all-around fascinating guy. They jump from stories of his days jumping out of planes to his hot takes on basketball, football, and movies. Expect a bit of everything and a lot of laughs as they cover all the bases with Edward in this all-over-the-map chat!

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“Join us as we chat with Randy Sadler, aka 3Coin, about his journey from the iconic Sadler’s Smokehouse to the world of poker and fashion. We dive into what it means to build meaningful connections and live with integrity.”

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Join us as Dan and Trent sit down with Bree Dollarhide, an 81-year-old professional bodybuilder. Born in a bomb shelter in Frankfurt German during World War II, Bree is coaching, training, and embodying strength and resilience. Discover her incredible journey and the secrets behind her remarkable health and vitality!

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In this wildly unfiltered and unexpectedly heartfelt episode, Trent and Dan are joined by the witty and charismatic Iris Chadwick for a ride that starts with feng shui and favorite colors and somehow ends with crackhead economics, stolen footballs, and the meaning of loneliness. Between laughter and chaos, Iris opens up about connection, communication, and self-sabotage, while the guys debate everything from Journey lyrics to flopp...

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In this episode of “Unprepared and Overconfident,” we’re celebrating “Jennifer’s Day Off!” Join us as we dive into the dynamic world of Jennifer Foreman, a dedicated wedding photographer and eyebrow microblading specialist. Not only is she a huge fan of our podcast—she’s listened to every episode and loves to engage with us—but she also brings her love of lists into the mix, organizing everything down to the finest detail. From cap...

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Join Dan Gill for ‘The Trent Experience: Unprepared and Lovin’ It,’ featuring special guest Trent Edwards! Get ready to peel back the layers and get to know Trent like never before. Expect candid stories, personal insights, and plenty of laughs as Trent shares his journey, passions, and the moments that shaped him.”

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October 7, 2025 107 mins

 

“In this episode of ‘Unprepared and Overconfident,’ Dan and Trent are joined by therapist Joey Forman. While Joey brings his serious expertise in therapy, the conversation is also filled with spooky ghost stories and plenty of laughs. Joey will be wearing a wizard’s hat for Crazy Hat Day, and they’ll even dive into the fun debate: Is a taco a sandwich? It’s the perfect blend of serious insights and lighthearted fun!”

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September 30, 2025 97 mins

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.

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September 23, 2025 111 mins

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!

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“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!”

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September 8, 2025 58 mins

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Get 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 lau...

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September 2, 2025 126 mins

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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!

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“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!”

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August 20, 2025 75 mins

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In 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!

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August 11, 2025 67 mins

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Join 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!

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Welcome 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.

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