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🎙️ Youngest in The Yacht Club – Davy Rolando (Betting on Hustle & Building Tampa Culture)
In this powerful episode, host Vince Serrano sits down with Tampa’s own Davy Rolando, radio legend, entrepreneur, and culture builder for a deep-dive into his journey from local DJ to full-blown business mogul. Davy opens up about the grind, the glow-up, and what it really takes to make a name in the city while staying authentic.
From radio waves to barbershops, Davy’s story is one of hustle, heart, and high-level execution. This episode is for anyone who’s ready to bet on themselves, take risks, and leave a legacy.
đź•’ Timestamps
00:00 – Intro: Vince welcomes Tampa legend Davy Rolando
00:24 – Shoutout to barbershops & community buzz
00:41 – Who is Davy Rolando? Entrepreneur, hustler, Tampa staple
01:26 – “Hands in multiple pots”: Building different streams of income
01:51 – Davy’s rise through radio & DJ’ing at WiLD 94.1
03:00 – Transitioning from radio to real estate, barbershops & business ownership
06:12 – Learning from the streets vs learning from college
08:48 – Being the plug: the power of community relationships
11:20 – The mindset behind betting on yourself
13:30 – Davy’s thoughts on legacy and motivating the next generation
16:05 – What people misunderstand about Tampa’s culture
18:22 – Navigating egos & staying humble in a growing city
20:01 – Managing multiple businesses and creative freedom
23:34 – Advice to up-and-comers: consistency, discipline, & real networking
26:18 – What Davy wishes he knew in his 20s
28:00 – The importance of balance: family, health, and business
30:44 – Davy shares the real reason he never gave up
34:15 – Rapid-fire questions: music, travel, dream collabs
36:22 – What’s next for Davy Rolando?
39:40 – Final message to the youth: Bet on YOU, stay consistent
🔥 If you’re an aspiring creative, entrepreneur, or anyone on the grind, this episode is a masterclass in self-belief and community building.
🎧 Available now on YouTube & Spotify for Podcasters
👇 Follow & Connect
@YoungestInTheYachtClub | @VinceSerrano | @DavyRolando
đź”– Hashtags for Maximum Reach
#YoungestInTheYachtClub #DavyRolando #TampaCulture #EntrepreneurMindset #DJLife #BarbershopCulture #TampaBay #RadioLegend #SelfMade #CreativeGrind #LegacyBuilding #MotivationPodcast #SpotifyPodcasts #YouTubePodcasts #VinceSerrano
View all episodes
By Vince SerranoIn this powerful episode, host Vince Serrano sits down with Tampa’s own Davy Rolando, radio legend, entrepreneur, and culture builder for a deep-dive into his journey from local DJ to full-blown business mogul. Davy opens up about the grind, the glow-up, and what it really takes to make a name in the city while staying authentic.
From radio waves to barbershops, Davy’s story is one of hustle, heart, and high-level execution. This episode is for anyone who’s ready to bet on themselves, take risks, and leave a legacy.
đź•’ Timestamps
00:00 – Intro: Vince welcomes Tampa legend Davy Rolando
00:24 – Shoutout to barbershops & community buzz
00:41 – Who is Davy Rolando? Entrepreneur, hustler, Tampa staple
01:26 – “Hands in multiple pots”: Building different streams of income
01:51 – Davy’s rise through radio & DJ’ing at WiLD 94.1
03:00 – Transitioning from radio to real estate, barbershops & business ownership
06:12 – Learning from the streets vs learning from college
08:48 – Being the plug: the power of community relationships
11:20 – The mindset behind betting on yourself
13:30 – Davy’s thoughts on legacy and motivating the next generation
16:05 – What people misunderstand about Tampa’s culture
18:22 – Navigating egos & staying humble in a growing city
20:01 – Managing multiple businesses and creative freedom
23:34 – Advice to up-and-comers: consistency, discipline, & real networking
26:18 – What Davy wishes he knew in his 20s
28:00 – The importance of balance: family, health, and business
30:44 – Davy shares the real reason he never gave up
34:15 – Rapid-fire questions: music, travel, dream collabs
36:22 – What’s next for Davy Rolando?
39:40 – Final message to the youth: Bet on YOU, stay consistent
🔥 If you’re an aspiring creative, entrepreneur, or anyone on the grind, this episode is a masterclass in self-belief and community building.
🎧 Available now on YouTube & Spotify for Podcasters
👇 Follow & Connect
@YoungestInTheYachtClub | @VinceSerrano | @DavyRolando
đź”– Hashtags for Maximum Reach
#YoungestInTheYachtClub #DavyRolando #TampaCulture #EntrepreneurMindset #DJLife #BarbershopCulture #TampaBay #RadioLegend #SelfMade #CreativeGrind #LegacyBuilding #MotivationPodcast #SpotifyPodcasts #YouTubePodcasts #VinceSerrano