Vibe and Wave Charters: The Boat Business That Started With a Dud and a Second Chance

<p>On this week’s episode, I traveled to Baltimore Harbor to interview the husband and wife team behind Vibe and Wave Charters: Caption Kay and D. <br /><br />What started as one man’s unexpected connection to the water has grown into a business built on joy, perseverance, partnership, and purpose. From a first boat that didn’t quite go as planned to creating unforgettable experiences for locals and visitors alike, their story is about taking a leap, learning along the way, and building something their family and community can be proud of.<br />At the heart of their journey is a shared commitment to their faith, their family, and their desire to inspire and serve others. Through entrepreneurship and their love of the water, Dee and Captain Kay are building a legacy that extends beyond their business—one that creates opportunities, brings people together, and gives their family something meaningful to pass on to the next generation.<br />In this episode, we get into entrepreneurship, legacy, representation on the water, and what it really takes to turn a dream into a thriving business.<br /> <br />Chapters<br />00:00 - Post-interview banter and final setup<br /><br />04:12 - Introduction to Vibe and Wave Charters in Baltimore<br /><br />04:47 - What Vibe and Wave Charters offers on the water<br /><br />05:40 - The story behind the third boat, Honey Lemon Pepper<br /><br />06:30 - Captain K’s first job on the water and the spark of purpose<br /><br />09:11 - Discovering Baltimore from the harbor instead of from land<br /><br />11:39 - The original plan to start a charter business<br /><br />13:33 - D explains how she helped bring the dream into reality<br /><br />14:44 - Getting the captain’s license and the first years of sea time<br /><br />16:59 - Learning from another Black charter operator in Baltimore<br /><br />17:49 - Buying the first boat during a season of pressure and fear<br /><br />20:15 - What the first boat was meant to do<br /><br />21:07 - The financial and emotional cost of the mistake<br /><br />22:19 - Going back to work as a captain for hire in DC<br /><br />25:31 - Why people management is a core business skill<br /><br />28:13 - Money management and the seasonal reality of maritime work<br /><br />30:00 - Launching Honey O’Bey and targeting intimate cruise experiences<br /><br />31:11 - Building the website and landing the first booking<br /><br />33:43 - How the couple complements each other as business partners<br /><br />36:08 - Advice for starting a business with a partner<br /><br />38:31 - How D invested in Captain K’s license before they were married<br /><br />41:19 - The early relationship story and why D believed in the vision<br /><br />44:47 - Creating an intentional guest experience on the water<br /><br />47:01 - Testing offerings and discovering what customers respond to<br /><br />48:39 - Safety, comfort, and helping nervous guests relax<br /><br />50:11 - Creative cruise ideas like themed karaoke, game nights, and wing competitions<br /><br />52:52 - Why trust and calm had to start inside their relationship<br /><br />54:23 - Black maritime history and why representation matters<br /><br />57:53 - Being an example for future captains and maritime workers<br /><br />59:19 - Access, barriers, and creating a space where guests can ask questions<br /><br />62:35 - What they want their five children to learn from the business<br /><br />65:11 - Passing the business down and building generational opportunity<br /><br />67:32 - Showing kids partnership, love, and possibility<br /><br />70:55 - What they are most proud of five years in<br /><br />72:48 - Community giving and a diaper drive for local families<br /><br />76:26 - Where to find Vibe and Wave Charters<br /><br />78:10 - Rapid fire questions and final reflections<br /><br />Resources"<br />Instagram: @Vibeandwavecharters<br />Website: <a rel="noopener noreferrer nofollow" href="https://www.vibeandwavecharters.com/" target="_blank">https