Recent Episodes & Season Updates
Season 2 Launch: The show officially entered its second season in January 2026, following a special "Soundtrack Session" in December that showcased the music Dan and Trent craft for the show.
Reunited and it feels so good.
We’ve missed you! Dan and Trent are officially back together starting March 17th. We’re bringing you fresh stories, incredible guests, and plenty of laughs to kick off the spring. Grab a drink, get comfortable, and join the ultimate hangout.
Notable Guest Highlights:
Iris Chadwick: A deep dive into everything from feng shui and "crackhead economics" to the meaning of loneliness.
Paul Varghese: A stand-up comedy-focused episode that even managed to discuss the power of Fisherman’s Friend lozenges.
Bree Dollarhide: An interview with an 81-year-old professional bodybuilder born in a WWII bomb shelter.
Show Format & Platforms
The podcast maintains its "ultimate hangout" vibe, characterized by a lack of scripts and high-speed, natural conversations. You can listen to full episodes on: [5, 6]
Apple Podcasts (https://podcasts.apple.com/us/podcast/unprepared-and-overconfident/id1831394805)
Spotify
iHeart (https://www.iheart.com/podcast/269-unprepared-and-overconfide-291926745/)
Behind the Scenes
The hosts describe themselves as "chaos creators," with Dan playfully labeled as a "professional interrupter and self-proclaimed expert on everything". The show often blends comedy with heartfelt moments, covering topics ranging from 90s nostalgia (like floppy disks) to personal therapy-style insights.
Baseball, Movies, and a Good Sit-Down with Mitch Lloyd
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.
7 Dec 2025
Unprepared and Overconfident: The Soundtrack Session.
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, so stay tuned for more unfiltered fun and new surprises!
28 Nov 2025
“Laughs, Lozenges, and Paul Varghese”
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!
18 Nov 2025
From the Sky to the Sidelines: An Edward Smith adventure
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!
11 Nov 2025
“From Smokehouse to Poker: The 3Coin Journey”
“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.”
4 Nov 2025
Strength Through the Ages: The Bree Dollarhide Story
Join us as Dan and Trent sit down with Bree Dollarhide, an 81-year-old professional bodybuilder. Born in a bomb shelter in Hamburg 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!
28 Oct 2025
“Journey, Floppy Disks, and Finding Yourself”
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 floppy disks making a comeback. It’s part comedy, part therapy, and 100% Unprepared and Overconfident.
21 Oct 2025
Jennifer Foreman’s Day Off: ‘The question isn’t what are we going to do, the question is what aren’t we going to do!’
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 capturing beautiful moments to sharing her favorite tips, Jennifer makes every day an adventure. Get ready for inspiration, laughter, and a whole lot of list-making fun!
14 Oct 2025
‘The Trent Experience: Unprepared and Lovin’ It,’
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.”
7 Oct 2025
Therapy, ghost, and taco debates with Joey
“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!”
30 Sept 2025
The Doop Show unleashed with RJ!
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.
23 Sept 2025
Brandon doing Brandon things!
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!
16 Sept 2025
“Laughing Through Therapy with the Blue-Haired Social Worker.”
“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!”
9 Sept 2025
April Gill-ty as charged!
Send us a text 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 laughs and surprises—don’t miss it!”
2 Sept 2025
Angela has a cunning plan: Wit and wisdom!
Send us a text Join Dan and Trent as 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!
26 Aug 2025
Jack be nimble, Jack be quick, Jack be on with Dan and Trent!
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!”
20 Aug 2025
Once, Twice, Three Times the Podcast
Send us a text 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!
12 Aug 2025
”More Confident Still Unprepared”
Send us a text 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!
6 Aug 2025
The 1st jib jab Unprepared and Overconfident begins
Send us a text 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.
Reach and audience
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Apple Podcasts (US)
5.0 / 5
6 ratings
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