Always On Adventures

Jamie Villamor & Jon Gray
  • 5.0 (7)
  • Places & Travel
  • Updated Weekly

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

  1. Jun 12

    Q&A: Why I Lied to TSA, Stranded Survival & Unlearning Past Relationships

    It's our first Q&A episode and we're answering YOUR questions about travel, relationships, survival, and more. Jamie admits to lying to TSA about having diabetes to avoid paying $7 for water, Jon shares his saxophone tour story from when he was 15 in Europe, they debate who would survive longer stranded in another country (military connections vs. tipping baristas), and they get deep about what they had to unlearn from past relationships to make the blended family work. Plus: Jamie's tackle box of color-organized snacks, Jon's steer riding championship era, Blue Lagoon Iceland disappointment, the pink beach in Bali that needed filters, and why Jon absolutely refuses to do a serious photoshoot on a horse in Turkey (despite being the 1990 steer riding champion). They also discuss luxury travel letdowns, who handles pressure better while traveling, and Jon's refusal to acknowledge Jamie's handwritten 5-page letters. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    39 min

  2. May 29

    Joshua Tree Reset: Tipping Culture & Spanish Pronunciations

    Reset Joshua Tree: https://www.stayreset.com/ Jamie and Jon escape to Joshua Tree and stay at Reset, an incredible modern hotel made from shipping containers in the middle of the desert. While there, they have a heated debate about tipping culture—specifically about a drive-thru coffee girl who gives Jamie the same compliment every single time. Jon argues from the barista's perspective (he grew up in the service industry), while Jamie refuses to tip for a scripted compliment. They also visit high-end restaurants like The Kitchen in the Desert and Thirty-9 Palms, try the famous Mas o Menos matcha (where Jamie butchers the Spanish pronunciation), and attempt to fly a drone during a windstorm. Plus: Jon's custom Tipsy Goat cowboy hat from his buddy in Dallas, the RingConn Ring sponsorship (no monthly fees unlike other rings), creepy homesteads in the middle of nowhere that look like meth houses, Joshua Trees and vortexes, moon-charged water rituals, and an update on their son-in-law's soccer career (8 goals, leading the league, possibly heading to Europe). They also mention potentially taking him to Slab City—a lawless California art community—if he ever messes up with Jamie's daughter. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    28 min

  3. May 15

    Instagram Ruined Mother's Day: Social Media Pressure in Relationships

    Jamie and Jon get real about social media pressure in relationships—and it gets heated. What started as a Mother's Day celebration turned into a fight about Instagram captions, birthday posts, and whether any of it actually matters. Jon wrote Jamie a 5-page handwritten letter for Mother's Day, but his Instagram caption wasn't good enough. Jamie didn't post Jon on his birthday because he was taking a break from Instagram, so he felt invisible. They hash out the "tag your sponsor" energy, why Jamie's daughters not posting her crushed her soul, and the double standard of posting exes versus current partners. Plus: Jon thinks Billy Idol might be his dad after watching the documentary and immediately calling his mom, Jamie tries on her Frankie B low-rise jeans from high school (they don't fit), the complicated family tree explanation that requires a diagram, and why they finally agreed to stop putting pressure on birthday and holiday posts. They also cover DMs, commenting on shirtless photos, and why Jon would find every like from March 3rd. If you've ever fought about Instagram in your relationship, this episode is for you. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    23 min

  4. May 8

    The Cost of Free Trips: Are Influencer Collabs Worth It? | Always On Adventures #17

    Jamie and Jon break down the real cost of "free" influencer trips—and spoiler alert: they're not actually free. From deliverables and mood boards to feeling pressure to always be "on," Jamie reveals why she'd sometimes rather just pay for the room. They discuss ring lights at dinner (so embarrassing), drone crashes in the Bahamas and Hawaii, unpacking and repacking just to get the perfect arrival shot, and why hospitality makes all the difference (shoutout to First Phorm's incredible personalized lockers). Jon shares his theory that Billy Idol might be his dad after watching the documentary and immediately calling his mom, plus the wild story of how Billy Idol got caught cheating through a baby monitor. They also cover the difference between modeling (transactional) and influencing (relationship-building), why Jamie manifested a musician but got a saxophone player instead of a guitarist, and how Jon somehow always ends up as the star even when it's supposed to be Jamie's cover shoot. If you've ever wondered what goes into those perfect travel posts, this episode pulls back the curtain. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    23 min

  5. May 1

    What You Learn About Someone When You Travel Together | Always On Adventures #16

    Jamie and Jon break down what you REALLY learn about someone when you travel together—and why you should take a 5-7 day trip before getting serious. From packing styles to bathroom privacy (Jon still won't go near Jamie after 3 years), they cover the good, the bad, and the hilarious. Jon reveals he's banned from wearing "poop brown" around Jamie, they debate luxury travel versus weekend getaways, and share why their Komodo dragon adventure in Bali almost ended before it started when Jamie saw the boat. Plus: makeup transformations that end marriages, the couple who orders for each other at every restaurant, airport etiquette pet peeves (don't clap when the plane lands), why JJ makes them arrive 3 hours early then eats the entire lounge buffet, and the travel habits that will make or break a relationship. If you're wondering whether your relationship can survive a trip, this episode is for you. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    29 min

  6. Apr 24

    Strip Clubs, CO2 Lasers & Makenna's Moving Out | Always On Adventures #15

    Jamie and Jon sit down for what was supposed to be an episode about luxury travel versus weekend getaways... and instead ended up talking about Vegas strip clubs, Canadian coin tipping, why Jon doesn't go to strip clubs anymore, Jamie's CO2 laser horror story, and McKenna moving out of state with her boyfriend (Jamie can't keep a secret). They rank Vegas strip clubs from their era—Crazy Horse, Treasures, Little Darlings, Sapphire, and the legendary Cheetahs—plus Jon's controversial take on why these places exist. Jamie admits she can't tell the difference in her skin after burning her face off with lasers, Jon says she looked like "leather face" at the airport, and Nixon's brutal honesty about Jamie's post-laser glow. Plus: Jon won't let Nixon sit between them at the movies, Jamie's empty nest syndrome (that she swears she doesn't have), and why Jon thinks strip clubs just aren't his vibe anymore. If you came for travel tips, you're in the wrong place. This is pure chaos. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    40 min

  7. Apr 17

    Old Vegas vs New Vegas: What It's Really Like Living in Sin City

    Jamie and Jon break down what it's REALLY like being born and raised in Las Vegas—beyond the Strip. From slot machines at every gas station to living in hotels for a year with three kids, they share the side of Vegas nobody talks about. Jon reveals human-sized catfish lurking in the Hoover Dam, Jamie confesses to underage gambling (and panicking when she won), and they expose the dark reality of what happens at slot machines at 10am. Plus: the Neon Boneyard, card counters getting surrounded at the Palms, Jon's tight curls era, flash floods with people stranded on car roofs, and why there's no last call in Vegas. If you think Vegas is just casinos and nightclubs, this episode will change your mind. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    39 min

  8. Apr 10

    Michael Easter: Why Comfort is Killing You | Rucking, Misogi & The 2% Rule

    Michael Easter—bestselling author of The Comfort Crisis, Scarcity Brain, and Walk with Weight—joins Jamie and Jon to discuss why modern comfort is quietly destroying our lives. They dive into Jon's brutal 48-hour misogi (4 miles every 4 hours), why only 2% of people take the stairs, the problem with ChatGPT relationship advice, rucking as the ultimate fitness hack, and Michael's journey to sobriety. Plus: Jamie's deer hunting mental breakdown in Maui, Lucky Charms confessions from a health expert, and why walking with weight might be the most powerful thing you can do for your body and mind. Subscribe to Michael's 2% Newsletter: https://www.the2percent.co/ Get his latest book, Walk with Weight: https://www.the2percent.co/walk-with-weight ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

    1h 27m
See All (22)

Trailer

5
out of 5
7 Ratings

About

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

Information

  • Creator
    Jamie Villamor & Jon Gray
  • Years Active
    2025 - 2026
  • Episodes
    22
  • Rating
    Explicit
  • Copyright
    © Jamie Villamor & Jon Gray
  • Show Website
    Always On Adventures