Podcast Summary: Stay Tranquilo – "Cuban Cowboy in the 305: Orlando Mendez on Motherland, Miami Roots & the 'Always Summer' Six-Pack"

Date: December 3, 2025
Host: Andre, Stay Tranquilo Network
Guest: Orlando Mendez, "The Cuban Cowboy"

Main Theme & Purpose

This episode spotlights the Miami-born, second-generation Cuban-American artist Orlando Mendez, best known as the “Cuban Cowboy.” The conversation explores Orlando’s deep Cuban roots, his journey to embracing and modernizing his heritage, his path into country music, the emotional power of his breakthrough track “Motherland,” and the creative process behind his new, summer-soaked project, "Always Summer Six-Pack." The laid back yet passionate exchange celebrates cultural identity, storytelling through music, and the joy of keeping traditions alive in a Miami context.

Key Discussion Points & Insights

1. Miami Roots & Cuban-American Identity

Timestamps: 01:57 – 07:09

• Orlando shares his family’s classic immigrant story: fleeing Cuba during Castro’s regime, starting over in Miami with nothing, and the responsibility he feels as a second-generation Cuban-American to honor that legacy.

• Discussion on the “baton-passing” of culture and the challenge of maintaining traditions as the generations move further from the homeland.

• The hosts note the importance of embracing the Cuban-American identity rather than shying away from it.

• Notable Quote:

  • “At the end of the day, we are...almost more American than we are Cuban...But that culture that runs through our veins, that Cuban blood, that's still there. It's our job to carry it on. Because if not us, then who?” – Orlando Mendez (04:00)

• Orlando reflects on a period in his life (especially in high school) when he distanced himself from his Cuban roots, only to later reclaim and celebrate them, realizing their importance after losing his grandparents.

2. Discovering Country Music & the Birth of the “Cuban Cowboy”

Timestamps: 07:16 – 10:41

• Orlando’s unexpected path to country music blossomed in high school, inspired by artists like Darius Rucker and Tim McGraw.
• Unlike many in the genre, Orlando discovered modern country before delving backwards into the genre’s roots (e.g., Johnny Cash, Merle Haggard).
• The “Cuban Cowboy” persona represents this blend of American and Cuban culture—modernizing and owning both sides of his identity.

3. Pandemic Pivot: From Acting to Music

Timestamps: 10:42 – 15:02

• Before the pandemic, Orlando pursued acting in Miami and NYC, landing theater and indie film roles.
• The COVID-19 shutdown abruptly ended his acting momentum, forcing him to return home.
• Quarantined in Miami with “all the time in the world,” he finally taught himself guitar (with YouTube) and began songwriting in earnest.
• Notable Quote:
  • “I feel alive [entertaining]...COVID changed the trajectory of my life. I’ve never looked back, and I’ve never been happier.” – Orlando Mendez (14:52)

4. Songwriting Process & the Creation of “Motherland”

Timestamps: 15:07 – 19:52

• Orlando describes his early songwriting as raw and uninhibited—"straight from the heart, straight off the dome."

• Two life events sparked “Motherland”: participating in the influential Miami show Amparo (which deepened his connection to his Cuban roots) and losing his grandparents.

• “Motherland” became a local anthem, directly connecting his personal journey to the broader Cuban-American experience.

• Notable Quote:

  • “One of the first things I wrote was that Motherland song...it was just coming straight out of me.” – Orlando Mendez (15:39)

• Reflecting on the songwriting process now, Orlando shares how increased experience has made him more self-critical, sometimes complicating the process that used to be so free.

5. The “Always Summer” Six-Pack: Concept & Creative Process

Timestamps: 20:29 – 26:46

• In a rut in Nashville, Orlando had a “look in the mirror” moment on a flight back to Miami, reflecting on what brings him joy: sun, ocean, boats, and the perpetual Miami summer.
• The concept for “Always Summer Six-Pack” was born: six summer-themed, coastal-vibe country songs capturing the Miami spirit.
• The bulk of the project came together during a two-day writing retreat in Key Largo with collaborators from the Mr. 305 camp, yielding 4-5 songs and most vocals recorded onsite.
• Notable Quote:
  • “I was on a plane back to Miami...just low, man. And I started thinking—what makes me happy? The sun. The ocean. Summer. Wouldn’t it be cool to write a bunch of summer-sounding songs?” – Orlando Mendez (21:07)

6. Tracklist & Songwriting Approach

Timestamps: 24:43 – 27:49

• Orlando shares how the tracklist came together:
  • “Modern Day Pirates” (written in 30 minutes), “Hurt to Hit,” “Day Drinking Tonight,” “Built to Last,” “Saltwater Salvation,” and “Beers Back Home.”
• The team typically started with titles (“probably the one thing that I’m best at”) before building songs around those concepts.
• “Beers Back Home,” written before the writing camp, is a proof-of-concept single about the comfort of returning to Miami and one’s roots.

7. Overcoming Project-Release Challenges

Timestamps: 30:27 – 32:15

• The EP’s release was delayed from summer to December due to funding, industry logistics, and collaborative scheduling.
• Orlando notes the importance of supportive local sponsors and the hurdles of being an independent artist who must “wear all the hats.”

8. Miami's Summer Vibe: More Than Weather

Timestamps: 32:06 – 34:32

• Miami’s “Always Summer” essence isn’t just climate, but a mindset and way of life sustained by culture, friendships, and environment.
• Orlando aspires for the Always Summer Six-Pack to bottle that feeling in music.
• Jimmy Buffett is cited as an inspiration for creating a lifestyle through music—transforming escape, peace, and leisure into anthems with universal appeal.

9. Music as Life’s Soundtrack

Timestamps: 35:07 – 36:51

• The hosts swap stories about the power of music to define memorable life moments (weddings, homecomings).
• Orlando shares his dream:
  • “I want my songs to be anthems in people’s lives. Just like I have anthem songs...that help get you through the joyful and the tough moments...that’s what I want my legacy to be.” – Orlando Mendez (36:22)

Notable Quotes & Memorable Moments

• “At the end of the day, we are...almost more American than we are Cuban...But that culture that runs through our veins, that Cuban blood, that's still there. It's our job to carry it on. Because if not us, then who?”
  – Orlando Mendez (04:00)

• “COVID changed the trajectory of my life. I’ve never looked back, and I’ve never been happier.”
  – Orlando Mendez (14:52)

• “I want my songs to be anthems in people’s lives…through the joyful moments and the tough ones. That’s what I want my legacy to be.”
  – Orlando Mendez (36:22)

• On Miami: “It’s always summer up here [points to head]…and always summer in your heart.”
  – Orlando Mendez (32:12)

Important Segment Timestamps

• Miami/Cuban-American legacy: 01:57 – 07:09
• Country music discovery & Cuban Cowboy identity: 07:16 – 10:41
• Pandemic shift from acting to music: 10:42 – 15:02
• Creating “Motherland”: 15:07 – 19:52
• Origin & writing of the Always Summer Six-Pack: 20:29 – 26:46
• Beers Back Home, tracklist discussion: 24:43 – 27:49
• Project release hurdles & gratitude for community: 30:27 – 32:15
• Always Summer philosophy & Jimmy Buffett inspiration: 32:06 – 34:32
• Music as life’s soundtrack & anthems: 35:07 – 36:51

Flow & Tone

The episode is vibrant, affectionate, and deeply personal, rich with Miami flavor, Cuban family lore, and the insider’s grind of an independent artist. The back-and-forth is casual and brotherly, full of laughter, encouragement, and heartfelt appreciation for heritage, hard work, and the magic of music.

Where to Listen & What’s Next

• Orlando’s “Always Summer Six-Pack” project drops December 5th, capturing the Miami sun in country melodies.
• Follow Orlando on socials:
  Instagram & TikTok: @orlandojmendezmusic

Whether or not you’re Cuban-American or even a country music fan, this episode oozes Miami soul, immigrant pride, southern storytelling, and the healing optimism of summer and song.