Welcome to Cruising Altitude — the podcast where we rise above the turbulence of life and step into the freedom, clarity, and luxury of living at our highest level.I’m Kelly O’Shea —business development consultant, private jet advisor, author, mom, and living proof that you can crash into life’s turbulence, pick up the pieces, and still arrive in style. Whether you’re navigating business, healing, or building a life that feels limitless, this is your boarding pass to living the life you were brave enough to chase.. So buckle up — we’re ready for takeoff.
with David Brauntz — Digital Marketing & SEO Specialist, New Business Partner of Kelly Florida vibes meet business mastery ☀️ Join Kelly as she welcomes her new business partner, David Brauntz, in this sizzling episode. Together, they dive into what it really means to rise in the Sunshine State — merging digital innovation, marketing muscle, luxury vision, and the unwavering drive to show up bigger than ever. What we’ll explore: How David built his digital marketing and SEO expertise, and...
27 Dec 2025
✈️Episode 9 — Couture & Cashflow: The Luxe Rise of Bosses in Heels
In this power-packed episode of Cruising Altitude, Kelly sits down with Alexis Ferguson — founder of Bosses in Heels PB, luxury connector, and unmistakable force in the Palm Beach elite. From the launch of a women-forward empire to commanding rooms where couture meets capital, Alexis shares how she built a brand that blends resilience, style, and strategic elevation. Expect a runway-ready conversation about: ✨ Turning vision into high-end experiences ✨ Scaling a community of ambitious women i...
20 Dec 2025
✈️Episode 8 — Repeating the Cycle
with Melissa Shelton — Kelly’s Middle-School Bestie who studied Child Psychology. What happens when the patterns we swore we’d outrun… start showing up in our own adult lives? In this deeply personal episode of Cruising Altitude, Kelly sits down with Melissa Shelton, a child psychologist and lifelong friend who has seen her evolution from the very beginning — all the way back to middle school. Together, they open up the early chapters of Kelly’s memoir: Chapter 1 — Princess Kitty Chapte...
13 Dec 2025
✈️ Episode 7 — The Light at the End of the Tunnel Is Inside of You
with Gabby Rothman What if the light you’ve been chasing… was within you all along? 💫 In this episode of Cruising Altitude, Kelly sits down with resilience advocate and radiant force, Gabby Rothman, to explore what it really takes to rise when life gets dark. From navigating deep tunnels of self-doubt to discovering a strength she didn’t know she had, Gabby shares the turning points, tools, and truths that helped her activate her inner light — and build a life that feels aligned, empowered, a...
6 Dec 2025
✈️ Episode 6 — This Ends With Us: Breaking Generational Curses & Building a Legacy with Dylan O’Shea
Some stories don’t just impact one life — they echo through generations. In this deeply personal episode of Cruising Altitude, I sit down with my son, Dylan O’Shea, to talk about breaking family patterns, reclaiming your story, and building a legacy rooted in choice, courage, and love. We dive into the moments that shook me to my core — the loss of his father, the end of a business partnership, and the termination of my longest-standing client campaign — all while navigating the challenges of...
29 Nov 2025
✈️ Episode 5 — The Warrior Awakened
Featuring: J.R. Hutter — U.S. Army Veteran, Recovery Coach, and Mentor Some battles are fought on the battlefield, and some are fought within. In this episode of Cruising Altitude, I sit down with J.R. Hutter, a U.S. Army Iraq War veteran, father, and former drug addict and alcoholic, to talk about his journey from darkness to discipline, purpose, and leadership. We share stories from our party pasts, the struggles that nearly broke us, and the choices that set us on a path to transformation....
22 Nov 2025
✈️ Episode 4: The Art of Reinvention: Finding Strength Through Motherhood with Blakely Giordano
This one hits close to home. Today’s episode features Blakely Giordano — a friend who’s been in my world since 2014, the year I stepped into a brand-new chapter of life. We open with the whirlwind: getting married in July 2014, bringing home Bailey that November, and welcoming Dylan on 11/27/15 — the moment everything changed. From a dream-life on paper to the shocking reality of being pushed out of my job at Magellan while caring for a newborn, and the unexpected pivot into baby brands, soci...
15 Nov 2025
✈️ Episode 3: From Strategy to Success: Mastering the Pivot with Paul Fioravanti
Turning Vision Into Reality with Paul Fioravanti — Interim CEO, Growth Strategist & Business Development Powerhouse. In this episode, we sit down with Paul Fioravanti, MBA, MPA, CTP — the executive leader companies call when the stakes are high and the path forward isn’t clear. With decades of experience as an interim CEO guiding organizations through transformation, Paul has become a master at turning strategy into measurable success. We also dive into my career journey — from NYC ...
8 Nov 2025
✈️ Episode 2 — Blooming Boldly Into Kings & Queens with David Breitenbach of BodyStreet
Some transformations don’t just happen in the gym — they happen in how you choose to show up for yourself. In this episode of Cruising Altitude, I sit down with David Breitenbach, my trainer from BodyStreet, to discuss the power of EMS training and how 20 minutes a day can feel like four hours in the gym — if you do it right. We dive into the moment I fully stepped into my power, aligning luxury, purpose, and emotional freedom, and explore how to separate yourself from others’ expectations to...
1 Nov 2025
✈️ Episode 1 — How to Rise After The Fall with Dr. Lisa C. Palmer, PhD, LMFT, CHT
Every rise has a beginning — and mine began long before I knew what resilience even meant. In this premiere episode of Cruising Altitude, I’m pulling back the curtain on the childhood stories, silent pressures, and early cracks that paved the runway for the woman I’m becoming today. I’m joined by Dr. Lisa Palmer — internationally recognized expert in trauma recovery and Director of The Renew Center of Florida. Together, we unpack the truth about growth: it doesn’t happen when life is smooth. ...
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