Trip Happens with Bert Weiss and Amanda Weiss

Today, we’re sitting down with legendary cowboy cook Kent Rollins and his wife, Shannon, to hear the story of how they met, fell in love, and built a life together on the open range. You've seen Kent on Cast Iron Cowboy on the Outdoor Channel, and he's competed on hit Food Network shows like Chopped Grill Masters and Beat Bobby Flay. Now, he's sharing the stories you won't hear on TV!

Plus, Bert and Amanda revisit some of their wildest celebrity interview stories, including encounters with Mariah Carey, Justin Bieber, J.Lo, Usher, and Chris Rock.

Follow Kent & Shannon Rollins and Listen to Cowboy Coffee Hour:
https://www.youtube.com/@CowboyKentRollins
https://pionairepodcasting.com/cowboycoffeehour/

Find us on Instagram, Facebook, and TikTok: @TripHappensPodcast

WRITE TO US!

Trip Happens
4279 Roswell Rd.#208 -221
Atlanta, GA 30342

For every postcard we receive from our listeners' travels, we'll donate $10 to Bert's Big Adventure, a nonprofit that takes kids with chronic & terminal illnesses and their families on a 5-day, VIP, all-expenses-paid trip to Walt Disney World.

Have a crazy travel story you want to share? Want Bert or Amanda to guest on your podcast? Email us! triphappens@pionairepodcasting.com

CHAPTERS
02:13 Bert’s Most Memorable Celebrity Interviews
03:24 The Truth About Justin Bieber
04:12 The Usher Interview That Made Worldwide Headlines
05:38 How an Usher Interview Inspired “Confessions”
06:30 What J.Lo Is REALLY Like Behind the Scenes
07:29 The Morning We Hung Up on Mariah Carey
09:18 Why Chris Rock Was One of Our Most Disappointing Interviews
10:21 The Biggest Food Fight in Our Marriage
12:03 Meet Cowboy Kent Rollins and Shannon
21:04 What Is Cowboy Culture, Really?
22:40 Why Cowboys Still Need Chuckwagon Cooks
23:28 What Life Is REALLY Like Cooking on a Ranch
30:43 The Tornado That Almost Forced Them to Abandon Camp
33:15 Cooking Through Extreme Weather: 117 Degrees to 90-MPH Winds
34:47 Why Kent Refused to Leave the Chuckwagon During a Storm
36:49 How Life on the Land Strengthened Their Faith
37:33 The “Luxury” That Turned Cowboy Camp Into a Spa
40:06 The Cowboy Who Loves Sushi and Beach Vacations
41:47 Cowboy Kent's Unexpected Pickleball Hobby
46:46 Ten Sleep, Wyoming: The Hidden Gem Most Travelers Miss
47:53 The Unexpected Hot Springs Between Saratoga and Rawlins
48:15 The Oklahoma Burger Worth Going Off the Beaten Path For
49:33 Would They Really Let Us Visit Their Ranch?
51:32 We're Starting a Pen Pal Project!

Advertising inquiries: advertising@pionairepodcasting.com

If you are interested in advertising on this podcast email advertising@pionairepodcasting.com

To request Bert & Amanda to be on your Podcast, Radio Show, or TV Show, reach out to talent@pionairepodcasting.com

This podcast is for entertainment purposes only. Views expressed on this podcast solely reflect those of the host and do not reflect the views of Pionaire.

In our first episode we are answering YOUR burning questions about our story, how we fell in love and why travel is so important to us. We thought there was no one better to help us tell our story than Gracie and Anthem Award winning radio veteran, Kristin Klingshirn. You’ve heard her on The Bert Show, Bob & The Showgram (and you can now hear her on her own show, Barely Functioning!), and today she’s helping us answer juicy questions like:

Why you should you travel with your partner before getting married?
What is our worst vacation accident?
When did we start dating?
What’s one positive trait we’ve brought out in each other?
What are our biggest “Icks” about each other?
What TRIP solidified us wanting to be together forever?
And more!

Follow Kristin Klingshirn and SUBSCRIBE to her new podcast, Barely Functioning below:
https://www.instagram.com/kriskling/
https://pionairepodcasting.com/barelyfunctioning/

Find us on Instagram, Facebook, and TikTok: @TripHappensPodcast

WRITE TO US!

Trip Happens
4279 Roswell Rd.#208 -221
Atlanta, GA 30342

For every postcard we receive from our listeners' travels, we'll donate $10 to Bert's Big Adventure, a nonprofit that takes kids with chronic & terminal illnesses and their families on a 5-day, VIP, all-expenses-paid trip to Walt Disney World.

Have a crazy travel story you want to share? Want Bert or Amanda to guest on your podcast? Email us! triphappens@pionairepodcasting.com

CHAPTERS
00:22 Meet Bert & Amanda Weiss
05:14 When Did Bert & Amanda First Catch Feelings?
06:54 How We Met: The Charity Trip That Started It All
17:16 Our Friends Thought This Relationship Was a Bad Idea
20:39 Our Biggest Relationship Icks
23:54 The Trip That Proved We Were Meant to Be Together
25:35 What Retirement Travel REALLY Looks Like
27:36 The Fourth of July Fireworks Disaster
33:50 Bert Crashes a Boat Into a Dock
35:41 The Tubing Accident That Terrified the Kids
37:52 Our Friend Kristin's Next Chapter After Radio
40:23 Getting Laid Off and Finding a Second Act
42:00 Midlife Crisis or Midlife Clarity?
46:46 How We Actually Plan Our Trips (Yes, We Use ChatGPT!)
48:37 Starting Over as a Stepparent
51:04 Does It Suck Traveling Without Your Partner?
52:33 The Secret to Feeling Safe in a Relationship

Advertising inquiries: advertising@pionairepodcasting.com

If you are interested in advertising on this podcast email advertising@pionairepodcasting.com

To request Bert & Amanda to be on your Podcast, Radio Show, or TV Show, reach out to talent@pionairepodcasting.com

This podcast is for entertainment purposes only. Views expressed on this podcast solely reflect those of the host and do not reflect the views of Pionaire.

Bert has three beefs with his wife, Amanda, and it all has to do with their trip to Slovenia. From the cute waiter in the restaurant to almost driving on the road, here's what went down...is he justified?

Ps. Justice for "The Sound Of Music"

Subscribe on Apple, Spotify, or check out episodes on YouTube - first episode drops October 29!

Find us on Instagram, Facebook, and TikTok: @TripHappensPodcast

Have a crazy travel story you want to share? Want Bert or Amanda to guest on your podcast? Email us! triphappens@pionairepodcasting.com

Advertising inquiries: advertising@pionairepodcasting.com

Launching Thursday, October 29th, Trip Happens is when life takes you somewhere you didn’t plan to go.
This isn’t just a podcast for people who love to travel. It’s for the non-travelers who would rather hear wild and remarkable stories than pack a suitcase. It's for anyone craving a sense of adventure while dealing with the chaos of everyday life.

From their own unhinged adventures that they’ve collected from traveling to 60 countries to the fascinating stories of their traveler guests, Bert Weiss and Amanda Weiss prove everybody has a unique traveling story to tell.
Travel is wild and life is even wilder, and the secret is to embrace it with open arms.

FOLLOW US: @TripHappensPodcast

Launching Thursday, October 29th, Trip Happens is when life takes you somewhere you didn’t plan to go.
This isn’t just a podcast for people who love to travel. It’s for the non-travelers who would rather hear wild and remarkable stories than pack a suitcase. It's for anyone craving a sense of adventure while dealing with the chaos of everyday life.

From their own unhinged adventures that they’ve collected from traveling to 60 countries to the fascinating stories of their traveler guests, Bert Weiss and Amanda Weiss prove everybody has a unique traveling story to tell.
Travel is wild and life is even wilder, and the secret is to embrace it with open arms.

FOLLOW US: @TripHappensPodcast

COMING OCTOBER 29, 2026
Trip Happens with Bert Weiss and Amanda Weiss

From fascinating travelers and unforgettable adventures to unexpected detours and the life lessons that come with them, Trip Happens is when life takes you somewhere you didn’t plan to go.

This isn’t just a podcast for people who love to travel. It’s for the non-travelers who would rather hear wild and remarkable stories than pack a suitcase. It's for anyone craving a sense of adventure while dealing with the chaos of everyday life.

From their own unhinged adventures that they’ve collected from traveling to 60 countries to the fascinating stories of their traveler guests, Bert Weiss and Amanda Weiss prove everybody has a unique traveling story to tell.

Travel is wild and life is even wilder, and the secret is to embrace it with open arms.

FOLLOW US: @TripHappensPodcast

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