In this episode of Story Traders, Caleb and his brother-in-law Elias sit down with Josiah to share the first half of their epic adventure across Iowa on RAGBRAI—the Register’s Annual Great Bicycle Ride Across Iowa.

They recount the first four days of the ride, from meeting colorful characters along the way to tackling the physical and mental challenges that come with biking across an entire state. With small-town charm, unexpected moments, and plenty of laughs, Caleb and Elias paint a vivid picture of what it’s like to be part of this one-of-a-kind event.

In this episode of Story Traders, Caleb takes the lead to tell Josiah about the rocky start to his family’s recent trip to Iowa. What was supposed to be a smooth journey turned into a string of car problems, last-minute fixes, and a whole lot of stress.

From mechanical headaches to desperate prayers, Caleb walks through the challenges of getting everything back on track—just in time to make the main event of their vacation: a bike ride across Iowa.

In this episode of Story Traders, Josiah takes the spotlight to share stories from his and his wife’s recent trip to Myrtle Beach.

From days on the golf course to hours in the pool, the trip was packed with laughs, family time, and plenty of memorable moments.

In this down-to-earth (literally) episode of Story Traders, Caleb and Josiah share stories about the trials and tribulations of mowing their lawns—and for the first time ever, Caleb’s 2-year-old son Oliver makes a special guest appearance on the podcast!

Caleb starts off with a classic— when his lawn mower battery died the day before leaving for vacation, leading to a last-minute scramble to get the yard under control.

Josiah follows with stories from when he and his wife first bought their house, including the creative (and slightly ridiculous) methods they used to keep their yard somewhat tamed while figuring things out.

Full of lawn mower woes, homeowner hustle, and toddler charm, this episode brings plenty of laughs and a reminder that yard work never goes quite as planned.

In this milestone 20th episode of Story Traders, Caleb and Josiah share a couple of fresh, real-life stories that prove the funniest moments often come from everyday life.

Josiah starts things off with a story about a pair of sunglasses—and the hilarious misunderstandings some family members had about them. Let’s just say things didn’t quite look the way they expected.

Then Caleb shares a recent daycare mix-up that led to a priceless photo of his 2-year-old son, Oliver—a picture that now lives on in family legend.

It’s a fun, feel-good episode full of little surprises, big laughs, and the kind of moments you just have to share.

The embarrassment continues in this episode of Story Traders as Caleb and Josiah dig up more cringe-worthy moments that are just too good not to share.

Josiah kicks things off with a painfully awkward story about a cashier who just couldn’t get a transaction right. Then Caleb takes us back to his college days with a legendary story about a group project gone wrong. He and his lab partners completely missed a key instruction from their professor, leading to a hilarious mishap that’s still being talked about a decade later.

Full of secondhand embarrassment and unforgettable blunders, this episode reminds us all that sometimes the best stories come from the moments we wish we could forget.

In this episode of Story Traders, Caleb and Josiah share some funny and relatable stories from everyday life—proving that sometimes the best stories are the ones still unfolding.

Caleb kicks things off with recent tales about his 2-year-old son, Oliver, who’s just learning to talk and try new things—resulting in plenty of laugh-out-loud moments and toddler-sized chaos.

Josiah wraps up the episode with a series of mishaps involving his house and some stubborn door locks that just can’t seem to cooperate, adding a whole new level of fun to homeownership.

It’s a fresh batch of real-life stories filled with parenting laughs, home repair woes, and all the unpredictable moments in between.

In this cringe-worthy episode of Story Traders, Caleb and Josiah dive into some of their most embarrassing moments—the kind of stories that make you want to crawl under a table… but are too funny not to share.

Josiah kicks things off with a painfully awkward moment in front of a friend’s grandma—on her birthday, no less. Caleb follows with two epic fails of his own: a tech-related blunder at work and a hilariously misguided question he asked at a local brewery that still haunts him.

It’s an episode full of secondhand embarrassment, real-life awkwardness, and the reminder that sometimes, the best stories come from the worst moments.