The Daily Drop

Landon Overby | James Massey

5.0 (3)
Careers
Updated Biweekly

The Daily Drop Podcast explores how every experience, decision, and relationship adds a drop to the bucket that shapes who we become. Each episode uncovers the journeys of people from all walks of life—their defining moments, pivots, and lessons learned along the way. From education and career moves to personal connections and turning points, you’ll hear how every drop counts when it’s poured into the right bucket.

Sep 28

The Teacher | Kristen Reed

Learning a new language is about much more than words. It's about connection, opportunity, and belonging. In this episode, we talk with Kristen Reed, an ESOL teacher with over 15 years of experience, about what it's like helping students navigate not only a new language but often an entirely new culture. Kristen shares memorable experiences from the classroom, the challenges her students face, and the moments that remind her why she chose this career. It's an insightful conversation about education, empathy, and the lasting impact a great teacher can have on someone's life.
Sep 14

The Wedding Photographer | Kailey Kercher

Some people's careers are built around numbers, strategy, or operations. Kailey Kercher's career is built around moments. In this episode, we talk with the professional wedding photographer and business owner about the responsibility of documenting once-in-a-lifetime memories and the relationships that make her work so meaningful. Kailey shares insights into the wedding industry, the realities of running a business, and what she's learned from working with countless couples during some of the most important days of their lives. It's a conversation filled with practical advice, personal stories, and plenty of inspiration for anyone pursuing a creative career.
Apr 27

The Used Car Guru | Rome Fiore

For this episode, we’re diving into the world of used cars, relationships, and doing business with purpose. We sit down with Rome Fiore, owner of Narrow Path Automotive, a faith‑based used car dealership, to talk about what it looks like to run a business rooted in values while competing in a tough industry. From customer trust to long‑term vision, Rome shares his approach to building something that’s about more than just sales. It’s an easygoing conversation filled with real‑life lessons, honest perspective, and a few moments that really make you think. Whether you’re interested in entrepreneurship, faith‑driven leadership, or how integrity plays a role in business decisions, this one’s worth the listen.
Apr 13

The Director of Football Operations | Jeremiah Cartwright

For this episode, we’re stepping behind the scenes of college football. We sit down with Jeremiah Cartwright, the Director of Football Operations for the University of Florida, to talk about everything that goes into running a major Division I program beyond what fans see on game day. From organization and leadership to managing the daily grind of a top‑tier program, Jeremiah shares insight into a role that keeps the entire operation moving.
Mar 30

The Healthcare Tech CEO | Terry Boch

For this episode, we’re stepping into the world of healthcare technology and leadership. We sit down with Terry Boch, CEO of a healthcare technology company, to talk about what it takes to lead in a fast‑moving, high‑impact industry. From innovation and growth to navigating challenges in healthcare tech, Terry shares real insight from the top. It’s an easygoing conversation filled with leadership perspective, forward‑thinking ideas, and a few moments that really make you pause. Whether you’re interested in healthcare, technology, or what it looks like to lead with vision, this one’s worth the listen.
Mar 16

The Analyst | Michael Ingram

For this episode, we’re stepping into the world of finance and strategy. We sit down with analyst Michael Ingram of Capital Strategies, a tax‑driven life insurance firm that serves high‑net‑worth families, substantial businesses, and large non‑profit organizations. Michael breaks down what his role really looks like and how analytical thinking plays a major part in long‑term financial planning. It’s an easygoing conversation filled with practical insight, real‑world perspective, and a few “that makes a lot of sense” moments. Whether you’re curious about finance, interested in analytical careers, or just want a better understanding of how strategy drives smart decision‑making, this one’s worth the listen.
Mar 2

The Creative Businessman | JB Roberts

For this episode, we’re diving into the intersection of business and creativity. We sit down with business owner JB Roberts to talk about his journey building a company while staying connected to his love for music. From creative outlets to the realities of running a business, JB shares how passion and purpose can coexist—even when life gets busy. It’s a laid‑back conversation filled with honest insights, creative perspective, and a few moments that really make you think. Whether you’re building something of your own or just trying to keep your creative spark alive, this episode is definitely worth a listen.
Feb 16

The Career Expert | Glenn Gibney

For this episode, we’re bringing in some real wisdom. We sit down with the Associate Vice President of Career Readiness at Georgia Southern University to talk about what it actually takes to build a career you’re proud of. From helping students find their path to understanding what employers are really looking for, Glenn shares the kind of insight you wish you had on day one.
Feb 2

The Physician | Dr. Tyler Fuqua

In this episode, we’re switching things up and sitting down with a doctor to talk about their career journey. From the first spark that led them to medicine to the challenges and wins along the way, it’s an honest look at what it really takes to build a life in healthcare. If you’ve ever wondered what goes on behind the scenes of becoming a physician—or just love hearing real stories—this one’s for you.
Jan 19

The Hosts | James & Landon

In the first episode of The Daily Drop, James and Landon sit down to share their career journeys—the highs, the lows, and the unexpected turns that got them here. Just two friends talking about where they started and what they’ve learned along the way.
Jan 6

Welcome to The Daily Drop

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1 Trailer

10 Episodes

Trailer

Welcome to The Daily Drop

Peep the best new career journey pod

5

out of 5

3 Ratings

The Daily Drop Podcast explores how every experience, decision, and relationship adds a drop to the bucket that shapes who we become. Each episode uncovers the journeys of people from all walks of life—their defining moments, pivots, and lessons learned along the way. From education and career moves to personal connections and turning points, you’ll hear how every drop counts when it’s poured into the right bucket.

Creator

Landon Overby | James Massey
Years Active

2026
Episodes

11
Rating

Clean
Copyright

© Landon Overby | James Massey
Show Website

The Daily Drop