BOBBYCAST Ep. 553: Vincent Mason on Touring, Milestones & Life on the Road

Date: November 11, 2025
Host: Bobby Bones
Guest: Vincent Mason (Country Singer-Songwriter)

Episode Overview

In this lively episode of the Bobbycast, Bobby Bones sits down with rising country artist Vincent Mason to discuss the whirlwind of his career, the realities of life on the road, and the release of his debut album, There I Go. The pair delve into everything from wild tour stories (including losing a van tire at 70 mph and hitting a black bear), the pressures of headlining versus supporting, the evolution from van to tour bus, money management as an artist, family influences, songwriting processes, and lessons learned from both music and sports. The conversation blends humor with honest insights about the music industry, personal insecurities, growth, and the satisfaction—and strangeness—of finding success.

Key Discussion Points & Insights

1. Life on the Road: Van vs. Bus

• Tour Mishaps:
  • Losing a van tire: “We're driving 70 miles an hour...the whole tire came off the axis, sparking down the road. I just see the tire, like, 40 yards in the air.” – Vincent Mason (35:18)
  • Wildlife encounters: “We hit a black bear...right in front of the van...and the next day, a hawk flew into the windshield.” (36:54)
• Hardships of Touring: Sharing a van with seven people, loading equipment, checking into hotels at 3 am, and playing frequent shows.
• Upgrading to a Bus: “The bus was, like, mythical by that point. ...You sleep more. You eat better. It's like a house.” – Vincent Mason (39:11)

Timestamps:

• Van story: 34:55 – 37:00
• Black bear/hawk: 37:48 – 39:05
• Bus upgrade: 39:11 – 40:24

2. Headlining vs. Supporting

• Pressure of Headlining: “There's nobody coming out there after you...I hope this show's not boring, or my songs are actually good.” – Vincent Mason (06:26)
• Success Milestones: Selling 1,000 tickets for a solo show was a personal goal come true.
• Tour Dynamics: Preference for headlining where you can build a relationship with the audience, but also appreciation for shorter support sets where "you can pop out the hits faster" (11:17).

Timestamps:

• Discussing nerves: 06:02 – 07:23
• Selling out presale: 08:04 – 08:14

3. Dealing with Self-Doubt and “Flat” Shows

• Acknowledgement that even when a performer's energy is off, the majority of audiences do not notice:
  • “I know a lot of times it’s me—even when I’m blaming ‘flat crowds.’” – Bobby Bones (09:47)
  • “95% of people would walk away being like, ‘I didn’t know anything was wrong.’” – Vincent Mason (09:56)
• Learning from Headliners: Headliners also feel this, and the ability to move past bad performances is critical.

Timestamps:

• Flat crowds & performance doubts: 09:21 – 10:37

4. The Money Side & Making It Work

• Business Milestones:
  • Hiring a business manager was both intimidating and a huge relief.
  • “It’s probably the thing I’m...most thankful for, having a business manager. Like, why is it that just because I can write songs and sing, I get to have a business?” – Vincent Mason (14:23)
  • Musings on artist income: “People think you’re selling a lot of tickets, make a lot of money, and you’re not. ...You don’t take that home. It’s expensive to have the bus, a band and a crew.” – Vincent Mason (69:53)
  • Tour sponsors (Monster Energy) make a noticeable difference in profitability (69:40)
• Spending Habits:
  • Vincent says he’s not a big spender, focusing mostly on essentials like a good guitar and reliable transportation.

Timestamps:

• Business manager: 14:20 – 15:35
• Sponsor discussion: 69:40 – 70:13

5. Family, Upbringing, and Support

• Parental Influence:
  • Dad is “like an A&R,” always honest and involved, especially on the business side, but never interfering with decisions (13:29).
  • Family attends as many shows as possible—approx. 10-15 a year (14:08).
• Honesty in Feedback:
  • “Everything goes—I send everything to my dad. He’s just a straight shooter.” – Vincent Mason (57:06)
• Relationship with his business manager and the importance of trust.

Timestamps:

• Family involvement: 13:21 – 14:18
• Feedback from dad: 57:06 – 57:28

6. Getting Started, Songwriting & Artistic Growth

• Songwriting Journey:
  • Began writing on a ukulele, moved to guitar at encouragement of his sister.
  • Learned writing mostly solo for years (“I didn’t start co-writing till two years in…I could have been anywhere, but I just moved to town because I knew this is where stuff happened.”) (28:16)
  • First song often covered: American Kids by Kenny Chesney (12:06)
• Songwriting Process:
  • Inspiration often comes from personal emotion and observing life, not necessarily direct autobiography.
  • Importance of keeping “the demo” feel; sometimes leaving a song as a single work tape on the album (54:29)
• Dealing with Demo-itis:
  • “You always lose a little something when you go to make it a full production.” (54:57)
• Favorite Artists: John Mayer and Parker McCollum as benchmarks for songwriting; validation when Parker quoted his lyrics (28:52 – 29:10).

Timestamps:

• Songwriting intro: 12:30 – 14:01
• Writing “Hell Is a Dance Floor”: 26:43 – 28:12
• Songwriting as growth: 25:27 – 25:46, 54:29 – 54:57

7. Viral Success & Notable Hits

• "Hell Is a Dance Floor":
  • Crossed 100 million streams.
  • “I don’t know what it was that made it the one that did that.” (52:52)
  • TikTok played a big role in viral lift, especially around the lyric “Rock bottom’s got a brand new view” (27:31).
• Reaction to Success:
  • "You put out song after song...then that's the one that catches everybody." – Bobby Bones (26:43)
  • Surprised by how little separates songs that "make it" from those that don’t.
• Authenticity in Music:
  • “I think now I write more about the feelings, and you use the story to get the feeling across. I don’t like it to be—this is about this person.” (59:03)

Timestamps:

• Viral hit details: 26:43 – 28:12

8. Touring Survival Stories & On-Stage Challenges

• Stage blunders:
  • "My mic didn't work for the first six minutes in front of 12,000 people. ...You have an internal anxiety attack." – Vincent Mason (41:04)
• Adaptability and Routine:
  • Found ways to feel “more at home” despite constant travel; routines developed over time make life easier but change frequently (24:23).
• Persistence through Adversity:
  • Surviving physically dangerous and emotionally taxing situations on the road deepens resilience.

Timestamps:

• Technical issues on stage: 41:01 – 42:08
• Making road life routine: 24:23 – 25:04

9. Imposter Syndrome and Navigating Success

• Both Bobby and Vincent admit to feeling imposter syndrome, especially when large opportunities or validation from idols arrive.
  • “Every one day you wake up and people just treat you a little different. ...It’s weird.” – Vincent Mason (34:25)
• Pressure to “amplify” a persona for public consumption; working to balance authenticity with performance.

Timestamps:

• Imposter syndrome: 33:22 – 34:48
• Amplifying personas: 50:21 – 52:26

10. Transferring Athletic Mentality to Music

• Vincent attributes part of his drive to his athletic background—valuing discipline, process, and persistence.
  • "I liked doing the work and being able to get better at it...Nick Saban talks about falling in love with the process." (70:28)
• Bobby notes that work ethic built in sports often transfers successfully to music.

Timestamps:

• Sports & process: 70:17 – 72:31

11. Reflections on Growth and Looking Back

• Both discuss how healthy it is to look back on older work and cringe, as proof of growth.
  • John Mayer anecdote: Even established stars struggle with loving their early work as much as their fans do.
  • “That’s always the goal—to look back and be a little [embarrassed]. That’s real growth.” – Bobby Bones (72:47)

Timestamps:

• Growth by looking back: 25:27 – 25:46, 72:34 – 73:36

Notable Quotes & Memorable Moments

• On Headlining Pressure:
  “There’s nobody coming out there after you...the first time I played a headline show, sold a thousand tickets...and then you’re like, oh, I hope this show’s not boring, or my songs are actually good.” – Vincent Mason (06:26)

• On Viral Hits:
  “I still feel like I don’t know what it was that made it the one that did that.” – Vincent Mason (52:52)

• On Tour Disasters:
  “The whole tire came off the axis...I see it like, forty yards in the air...we all lost sight of the tire.” – Vincent Mason (35:18)

• On Growth:
  “If you’re not in two years looking back at it going, oh, man, that means you haven’t gotten much better, you haven’t progressed.” – Bobby Bones (25:46)

• On Family Feedback:
  “Everything goes—I send everything to my dad. He’s just a straight shooter.” – Vincent Mason (57:06)

• On Athletic Mentality:
  “Nick Saban talks about falling in love with the process. ...It's so much easier to tune out the stuff that might get weird.” – Vincent Mason (71:09)

Additional Highlights and Fun Moments

• Vincent thought he saw Bobby’s doppelganger at his gym, leading to a recurring running joke about mistaken identity (04:14 – 05:36, 69:31).
• Discussed the surreal feeling of companies sending Vincent free clothes as “influencer” perks—and how odd it is that fame attracts free stuff only once you need it least (17:06, 23:41).
• Both shared insights into managing performance anxiety and “flat” crowds—recognizing that sometimes the issue is internal, not with the audience.
• The support of sponsors is revealed as a vital element in enabling artists to tour profitably (69:40).

Timestamps for Key Segments

| Topic | Timestamps | |------------------------------------|-------------------| | Meeting Bobby’s Gym Twin | 04:14 – 05:36 | | Touring: Van vs. Bus | 34:55 – 40:24 | | Headlining vs. Support | 06:02 – 11:41 | | Business Management & Money | 14:20 – 15:35 | | Family Influence | 13:21 – 14:18 | | “Hell Is a Dance Floor” Story | 26:43 – 28:12 | | Performance Doubt/Flat Crowds | 09:21 – 10:37 | | Imposter Syndrome | 33:22 – 34:48 | | Technical Stage Mishaps | 41:01 – 42:08 | | Songwriting Process | 12:30 – 14:01 | | Notes, Lyrics & Worktapes | 53:14 – 54:57 | | Passing the Growth “Cringe Test” | 25:27 – 25:46 | | Athletic Mentality in Music | 70:17 – 72:31 | | Sponsors’ Impact | 69:40 – 70:13 |

Closing

Vincent Mason’s chat with Bobby Bones reveals both the glamorous and gritty realities of modern country music—from van breakdowns to viral hits, and the weirdness of growing into success. For aspiring musicians, fans, and industry insiders, this episode is both entertaining and insightful—a candid look at the unpredictable, hard-working, sometimes hazardous, but always rewarding life of a traveling songwriter.

[Check out Vincent Mason's debut album There I Go and follow him on socials for tour updates.]