Always on Adventures
is a free-wheeling conversation show hosted by entrepreneur, international cover model, and TeamUSA sponsored competitive shooter Jamie Villamor alongside hospitality innovator and experiential expert Jon Gray. Jamie and Jon, each a powerhouse in their own right, also happen to be a couple who spend their days globetrotting across countries and continents.
Their conversations always begin previewing or recapping their adventures together, spanning all corners of the earth. Where those conversations end, though, is anyone’s guess. Between their three kids (each!), their b
New York Fashion Week Has Changed | Ep. 29, Part 1
Jamie returns from New York Fashion Week with an insider’s perspective on how the industry has changed—from runway standards and the rise of influencers to models working for exposure. Drawing on her own modeling career, she shares what surprised her and why free products don’t pay the bills.
Meanwhile, Jon’s outfit gets rejected mid-podcast, Jamie makes her case for sexy grandmas, and a solo trip becomes a New York food tour thanks to Jon’s restaurant recommendations. Next week, the adventure continues in Washington, D.C., where Jamie discovers she’s agreed to more than she realized.
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FOLLOW US ON SOCIAL MEDIA!
Always On Adventures Website: https://alwaysonadventures.world/ (https://alwaysonadventures.world/)
Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ (https://www.instagram.com/jamie_villamor/)
Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ (https://www.instagram.com/grayjon/)
Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ (https://www.instagram.com/alwaysonadventures/)
Have a suggestion for the show? Email us: hello@alwaysonadventures.world (mailto:hello@alwaysonadventures.world)
Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/ (https://www.instagram.com/mr_george_carmona/)
9 Oct 2026
The Baby Shower Debrief, Part 2: Candy Wars & Blended Family Drama
The baby shower is over, but the debrief isn’t. Jamie and Jon pick up with candy-bar drama, disappearing decorations, and a dog accident that turned into a family argument—with 80 guests in the house.
Then they get into the realities of blended families: relatives you’d rather avoid, sons-in-law who need a family tree, and why Jon gets along with Jamie’s ex-husband. Plus, a 6:30 a.m. wake-up call proves that grown kids don’t stop needing Mom—or her credit card.
____________________________
FOLLOW US ON SOCIAL MEDIA!
Always On Adventures Website: https://alwaysonadventures.world/ (https://alwaysonadventures.world/)
Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ (https://www.instagram.com/jamie_villamor/)
Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ (https://www.instagram.com/grayjon/)
Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ (https://www.instagram.com/alwaysonadventures/)
Have a suggestion for the show? Email us: hello@alwaysonadventures.world (mailto:hello@alwaysonadventures.world)
Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/ (https://www.instagram.com/mr_george_carmona/)
6 Oct 2026
80 Guests & Zero Boundaries: The Baby Shower Debrief
The baby shower is over, the family has flown home, and Jamie and Jon have plenty to unpack. From hosting 80 women and resetting breakers to gift-opening fatigue, candy-bar drama, and a badly timed dog accident, Makenna’s celebration delivered more than a few stories.
They also get honest about navigating blended families, whether you should pretend to like relatives, and why grown kids still treat Mom’s house like their own. With two daughters pregnant, Jamie’s next adventure is getting closer—and apparently, nobody is giving up their childhood bedroom.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
7 ratings
Spotify
5.0 / 5
6 ratings
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