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.

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.
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.
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.

Chapters
00:00 - Post-interview banter and final setup

04:12 - Introduction to Vibe and Wave Charters in Baltimore

04:47 - What Vibe and Wave Charters offers on the water

05:40 - The story behind the third boat, Honey Lemon Pepper

06:30 - Captain K’s first job on the water and the spark of purpose

09:11 - Discovering Baltimore from the harbor instead of from land

11:39 - The original plan to start a charter business

13:33 - D explains how she helped bring the dream into reality

14:44 - Getting the captain’s license and the first years of sea time

16:59 - Learning from another Black charter operator in Baltimore

17:49 - Buying the first boat during a season of pressure and fear

20:15 - What the first boat was meant to do

21:07 - The financial and emotional cost of the mistake

22:19 - Going back to work as a captain for hire in DC

25:31 - Why people management is a core business skill

28:13 - Money management and the seasonal reality of maritime work

30:00 - Launching Honey O’Bey and targeting intimate cruise experiences

31:11 - Building the website and landing the first booking

33:43 - How the couple complements each other as business partners

36:08 - Advice for starting a business with a partner

38:31 - How D invested in Captain K’s license before they were married

41:19 - The early relationship story and why D believed in the vision

44:47 - Creating an intentional guest experience on the water

47:01 - Testing offerings and discovering what customers respond to

48:39 - Safety, comfort, and helping nervous guests relax

50:11 - Creative cruise ideas like themed karaoke, game nights, and wing competitions

52:52 - Why trust and calm had to start inside their relationship

54:23 - Black maritime history and why representation matters

57:53 - Being an example for future captains and maritime workers

59:19 - Access, barriers, and creating a space where guests can ask questions

62:35 - What they want their five children to learn from the business

65:11 - Passing the business down and building generational opportunity

67:32 - Showing kids partnership, love, and possibility

70:55 - What they are most proud of five years in

72:48 - Community giving and a diaper drive for local families

76:26 - Where to find Vibe and Wave Charters

78:10 - Rapid fire questions and final reflections

Resources"
Instagram: @Vibeandwavecharters
Website: https://www.vibeandwavecharters.com/