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  • 52. 25 Years at Disney: Leadership Lessons & Career Reinvention with RK Kelley

    52. 25 Years at Disney: Leadership Lessons & Career Reinvention with RK Kelley
    2026/06/03
    In this episode of the B Student podcast, RK Kelley shares her incredible career journey from spending more than 25 years in leadership roles at Disney to becoming a driving force behind the Central Florida Pledge, a community initiative dedicated to fostering dignity, respect, and civil discourse across Central Florida.

    RK discusses career transitions, purpose-driven leadership, mentorship, women in leadership, community engagement, Disney leadership lessons, workplace culture, and the challenges facing organizations in today's divided environment.

    Throughout the conversation, RK discusses:
    • Disney Leadership Lessons: What 25+ years in global operations taught RK about workplace culture and respect.
    • Career Reinvention: Navigating the shift from a high-intensity executive role to a purpose-driven "second act."
    • The Central Florida Pledge: Why dignity and civil discourse are the most critical tools for today’s community leaders.
    • Redefining Success: How to prioritize family and values while maintaining professional impact.
    RK also shares how stepping away from a demanding executive career allowed her to redefine success, prioritize family, and embrace a purpose-driven chapter focused on creating lasting impact.

    If you're exploring a career change, leadership growth, personal development, women in business, nonprofit leadership, or community impact, this episode is full of actionable insights and inspiration.

    Time Stamps:
    00:00 Welcome to the Podcast
    02:01 What Is the Central Florida Pledge?
    04:26 Why RK Kelley Chose a Purpose-Driven Career
    06:45 How Businesses Can Get Involved
    09:12 Creating Respectful Dialogue Across Differences
    11:35 The Biggest Challenge Facing Communities Today
    13:57 A Vision for Central Florida's Future
    16:20 Why Listening Is a Critical Leadership Skill
    17:42 Lessons Learned from 25+ Years at Disney
    20:35 The Relaunch Program and Career Reinvention
    24:15 Mentorship, Self-Doubt, and Growth
    28:08 Redefining Success Through Purpose and Family

    -----------------------------------

    Listen to more episodes of The B-Student Podcast wherever you get your podcasts.

    -----------------------------------

    Connect with our Guest:
    LinkedIn: https://www.linkedin.com/in/rk-little-kelley

    Learn More about Winter Park Chamber of Commerce:
    https://www.winterpark.org/

    --------------------------------
    Podcast produced by Hi Hello Labs:     https://www.hihellolabs.com/
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    31 分
  • 51. The Soft Skills AI Can’t Touch: Career Success & Real Estate with Courtney Pelfrey

    51. The Soft Skills AI Can’t Touch: Career Success & Real Estate with Courtney Pelfrey
    2026/05/27
    How do you pivot careers from higher ed to real estate while managing motherhood and a family business? Courtney Pelfrey (Miller Grant & Company) joins Ashley Billings on the B Student Podcast to reveal the reality of building a relationship-based business in Winter Park, FL.

    In this episode, we go past the transaction to discuss the emotional side of home buying, the truth about career transitions, and the "secret" soft skill every professional needs: curiosity.

    Watch the full conversation to learn:
    • The Pivot: How Courtney moved from 10 years in collegiate career services into the real estate industry.
    • The "Baby" Metaphor: Why closing on a home is like bringing home a baby and why aftercare matters.
    • Curiosity vs. AI: Why curiosity is the leadership skill technology can't replicate.
    • Family Dynamics: The challenges and rewards of running a brokerage with your father and sister.
    • Working Motherhood: Practical wisdom on staying present as a mom while building a recognizable local brand.
    • Relationship Business: Why being "purpose-driven" wins over trends every time.

    Whether you're a relauncher returning to the workforce, a new agent, or a business owner in a new season of life, Courtney’s journey offers a roadmap for staying aligned with your values.

    If you enjoyed this episode, make sure to subscribe, leave a review, and share it with someone navigating a new season in life or business.

    Time Stamps:
    • 00:00 – Meet Courtney Pelfrey & Her Career Pivot Story
    • 02:12 – Why She Left Higher Education for Real Estate
    • 04:48 – Building a Family-Owned Real Estate Business
    • 05:31 – Why Closing on a Home is Like Bringing Home a Baby
    • 07:15 – Working With Family: Strengths, Roles & Dynamics
    • 09:42 – Creating a Relationship-Driven Real Estate Brand
    • 12:18 – The Emotional Side of Buying & Selling Homes
    • 14:36 – How Career Services Prepared Her for Real Estate
    • 17:08 – The Reality of Working Motherhood & Flexibility
    • 19:45 – Balancing Business, Kids & Boundaries at Home
    • 22:04 – Social Media, Branding & Standing Out in Real Estate
    • 24:26 – Advice for Young Realtors Starting Their Careers
    • 26:18 – Why Curiosity Is a Powerful Leadership Skill That AI Can’t Replace
    • 28:10 – Serving the Winter Park Community & What’s Next for Miller Grant

    -----------------------------------

    Listen to more episodes of The B-Student Podcast wherever you get your podcasts.

    -----------------------------------
    Connect with our Guest:
    Website: https://millergrantandco.com/
    Instagram: https://www.instagram.com/courtneympelfrey/
    LinkedIn: https://www.linkedin.com/in/courtneympelfrey/


    Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/
    --------------------------------

    Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
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    30 分
  • 50. How to Return to Work After a Career Break (With Confidence)

    50. How to Return to Work After a Career Break (With Confidence)
    2026/05/20
    Thinking about returning to work after a career break — but not sure where to start?

    In this episode, Ashley Billings interviews Betsy Gardner, CEO of Evermore Advisory and former President & CEO of the Winter Park Chamber of Commerce. After her own 13-year career break, Betsy created the Relaunch program — a proven return-to-work program now helping professional women confidently reenter the workforce across the country.

    Whether you've been out of the workforce for 2 years or 15, this episode breaks down exactly what it takes to come back — not at the bottom, but at your level.

    What you'll learn:
    • How to return to work after a career gap without starting over
    • Why women struggle with confidence after a career break (and how to rebuild it)
    • How to update your resume, LinkedIn profile, and personal brand for reentry
    • The 3 drivers of every career decision: control, content, and compensation
    • Why forward-thinking employers are actively hiring career returners

    The leadership and soft skills that make returning women high-value hires

    This episode is for you if:
    • You're woman considering returning to work after time off for family, caregiving, or personal reasons
    • You're mid career-transition and need a confidence reset
    • You're an HR leader or employer looking to hire experienced returning professionals


    Timestamps:
    (00:00) Introduction + Betsy Gardner and the Relaunch program
    (03:05) The origin of the Relaunch program
    (06:10) The business case for hiring women returning to the workforce
    (09:15) Why women leave the workforce and struggle to return
    (12:20) The confidence gap after a career break
    (15:10) Betsy's personal career reentry story
    (18:05) What Relaunch teaches (branding, resumes, LinkedIn)
    (21:00) The psychology of returning to work after years away
    (24:05) Control, content, compensation: the 3 Cs of starting a job
    (27:10) How employers should view resume gaps in 2026
    (30:00) The hidden skills career returners bring to the workplace
    (33:00) Final advice: stop waiting for the "right time" to return to work
    -----------------------------------
    Listen to more episodes of The B-Student Podcast wherever you get your podcasts.

    If this episode helped you, subscribe, leave a review, and share it with a woman who needs to hear it.

    -----------------------------------

    Connect with our Guest:
    Website: http://Humanintheroombook.com Or http://Betsygardner.com
    Instagram: https://www.instagram.com/thebetsygardner
    YouTube: @humanintheroompodcast

    Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/
    --------------------------------
    Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
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    36 分
  • 49. Why Creativity and Curiosity Matter in Leadership | Jennifer Deery | B Student

    49. Why Creativity and Curiosity Matter in Leadership | Jennifer Deery | B Student
    2026/05/14
    Today on the B-Student Podcast, Ashley Billings interviews Jennifer Deery, Executive Director of the Albin Polasek Museum & Sculpture Gardens, about her journey from corporate banking leadership to nonprofit arts and culture leadership in Winter Park, Florida.

    Jennifer shares how growing up moving frequently helped shape her adaptability, curiosity, and leadership style. She opens up about earning her Fine Arts degree, working as an art director in the corporate world, and eventually transitioning into museum leadership and nonprofit management.

    This episode explores:
    • Career pivots and professional reinvention
    • Leadership lessons from corporate and nonprofit spaces
    • Why arts and culture matter to local economies
    • The impact of museums and cultural institutions
    • The story and legacy of sculptor Albin Polasek
    • Creativity, curiosity, and lifelong learning
    • How art inspires innovation and community connection
    • Winter Park’s thriving arts and culture scene
    • Stroke awareness and resilience through creativity
    • Advice for young creatives and aspiring leaders
    Jennifer also shares exciting updates about upcoming exhibits, educational programming, collaborations with local organizations, and the museum’s vision for the future as it celebrates 65 years.

    If you’re passionate about leadership, creativity, entrepreneurship, nonprofit work, museums, community development, or personal growth, this conversation is packed with valuable insight.

    Time Stamps:


    00:00 – Introduction to Jennifer Deery & the Polasek Museum
    02:08 – Childhood influences, travel, and discovering museums
    04:12 – Jennifer’s first year leading the museum
    06:18 – The future vision for the Polasek Museum
    08:03 – Transitioning from board member to Executive Director
    10:38 – Why arts and culture are economic drivers in Winter Park
    13:02 – Collaboration between local museums and cultural organizations
    15:02 – Jennifer’s career path from art school to corporate leadership
    17:20 – Creativity, psychology, and leadership in business
    18:55 – Museum tourism and attracting visitors from around the world
    20:02 – Upcoming exhibits, events, and community programming
    23:24 – Albin Polasek’s resilience after stroke & advice for creatives
    Listen to more episodes of The B-Student Podcast wherever you get your podcasts.

    Like this video, subscribe, and comment your favorite London spot or what city has most transformed you.
    -----------------------------------
    Connect with our Jennifer:
    Website: https://polasek.org/
    LinkedIn: @jennifer-deery
    Instagram: https://www.instagram.com/polasekmuseum/

    -----------------------------------

    Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/

    Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
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    27 分
  • 48. She Quit Law Twice, Then Invented a Water Scooter | B Student | Lindsay Kiley

    48. She Quit Law Twice, Then Invented a Water Scooter | B Student | Lindsay Kiley
    2026/05/06
    Lindsay Kiley did it twice. She stepped away from law to raise her kids, went back to try again as a lawyer, and still something didn't feel right. It wasn't until she invented the Swelly water scooter that she finally built something that felt in alignment.

    In this episode, host Ashley Billings talks with Lindsay about what those in-between years looked like: the failed ventures, the slow realization that returning to law wasn't the answer, and what it takes to keep going when nothing is working.

    The overnight success part? It's the smallest part of the story.

    We get into:
    • Leaving law, returning to it, and leaving again
    • The Campable startup experiment and what it taught her
    • Entrepreneurship while raising kids, the parts nobody posts about
    • How Swelly went from a garage idea to retail shelves
    • What she'd tell anyone who feels like they've missed their window
    If you're mid-pivot, stuck, or rebuilding, Lindsay's been there. More than once.
    This episode is part of B Student: Summer School, a limited series featuring entrepreneurs and professionals who have gone through Winter Park Chamber of Commerce leadership and talent development programming

    #swelly #entrepreneurship #womeninbusiness #femalefounder #smallbusiness #productbusiness #careerpivot #careerchange #workingmoms #mompreneur #founderstory #youtubepodcast #spotifypodcast #businesspodcast

    Time Stamps:
    00:00 Introduction + Meet Lindsay Kiley
    02:45 Leaving Law + Entering the Unknown
    05:30 Trying Again (And Why It Still Didn’t Fit)
    08:10 Failed Paths: Campable + In-House Role
    10:50 Starting Over Without a Plan
    13:30 Building Resilience + Not Giving Up
    16:00 Mom Life + Returning to Work
    18:45 Entrepreneurship While Raising Kids
    21:30 Launching Swelly + First Wins
    24:00 Expanding the Brand + New Products
    26:30 Overcoming Fear + Stepping Outside Comfort Zone
    29:30 Advice for Career Pivots + Final Thoughts
    -----------------------------------
    Listen to more episodes of B Student wherever you get your podcasts.

    Like this video, subscribe, and leave a comment with the moment you knew it was time to make a change.
    -----------------------------------
    Connect with our Guest:
    Website: https://swelly.us/
    Instagram: https://www.instagram.com/swelly.us/

    Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/
    --------------------------------
    Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
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    31 分
  • 47. Graduation Day Betsy’s Final Episode

    47. Graduation Day Betsy’s Final Episode
    2026/04/22
    This is more than a farewell episode… it’s a leadership blueprint for the future of work.

    In this powerful final episode as host of the B Student Podcast, Betsy Gardner reflects on the biggest lessons learned from interviewing top leaders, entrepreneurs, and changemakers across the globe. From navigating business challenges to building meaningful relationships, this episode dives deep into what truly drives success in today’s world.

    You’ll learn why relationships matter more than strategy, how vulnerability becomes your greatest leadership advantage, and why soft skills are the most critical asset in the age of AI.

    This episode also explores:
    • Why human connection is the missing piece in modern leadership
    • The growing mentorship gap in today’s workforce
    • How vulnerability builds trust, influence, and impact
    • The importance of presence, polish, and personal brand
    • Lessons from top guests including entrepreneurs, chefs, and industry leaders
    • What’s next for the B Student Podcast and “B Student Summer School”
    If you’re a leader, entrepreneur, young professional, or someone navigating growth in your career, this episode will challenge how you think about success and equip you with the mindset needed for what’s ahead.


    Time Stamps:

    0:00 Graduation Day & Final Episode Begins
    1:30 Reflecting on the Podcast Journey
    3:00 Why Relationships Matter More Than Results
    4:30 The Mentorship Gap & Human Skills Crisis
    6:00 Vulnerability in Leadership & Personal Growth
    7:30 Learning to Show Up Authentically
    9:00 The Power of Feedback & Being Coachable
    10:30 Lessons from Guests & Real Conversations
    12:00 The Future of Work, AI & Soft Skills
    13:30 What’s Next: Summer School & New Chapter
    15:00 Betsy’s Next Move & Final Thank You
    -----------------------------------
    Listen to more episodes of The B-Student Podcast wherever you get your podcasts.

    Like this video, subscribe, and comment your favorite London spot or what city has most transformed you.
    -----------------------------------
    Connect with Betsy Gardner:
    Website: https://www.betsygardner.com/

    Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/
    --------------------------------
    Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
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    16 分
  • 46. Mayor Buddy Dyer: The "Airport Tram" Voice Who Led Orlando Through the Pulse Tragedy | B Student

    46. Mayor Buddy Dyer: The "Airport Tram" Voice Who Led Orlando Through the Pulse Tragedy | B Student
    2026/04/15
    Orlando Mayor Buddy Dyer sits down with Betsy Gardner for one of the most candid conversations he's ever had on camera.

    Before he became Orlando's longest-serving mayor, Buddy Dyer lost his first election, felt out of his depth at Brown University, and spent time selling industrial sealant door-to-door. This is the story he doesn't usually tell - and the lessons that shaped his leadership. In this episode of B Student, Mayor Dyer opens up about how losing early turned out to be the best thing that ever happened to him, the unexpected phone call from Pastor Sam Green that convinced him to run for mayor, and what he's learned about showing up for people when the stakes couldn't be higher.

    But the heart of this conversation is what happened on June 12, 2016. Mayor Dyer talks about the moment he got the 2am phone call about the Pulse nightclub shooting, what he did first, why he went toe-to-toe with FBI agents to insist that Orlando needed to see its mayor speak, and how grief from that night didn't fully catch up with him until the first anniversary of the tragedy.

    The conversation also goes deep on fatherhood, legacy, and - in a B Student exclusive - the name of Orlando's new first dog.

    If you're navigating setbacks, building something, or trying to lead people through hard moments, this one is worth your full attention.

    Time Stamps:
    • 00:00 Welcome + intro to Mayor Buddy Dyer
    • 02:15 The iconic airport tram voice & unexpected notoriety
    • 04:30 From top student to feeling average at Brown University
    • 07:45 Advice on competing in high-performance environments
    • 10:20 First political run… and losing early
    • 12:40 The “thank goodness I lost” mindset shift
    • 15:10 Selling “TerraSeal” and learning real-world skills
    • 18:00 Law school success + losing to Charlie Crist
    • 21:10 Networking, relationships, and winning people over
    • 24:30 Becoming an “accidental mayor” of Orlando
    • 27:45 Vision for Orlando + building a thriving city
    • 30:20 Leading through the Pulse nightclub shooting
    • 35:10 Crisis leadership, communication, and emotional resilience
    • 38:20 Fatherhood, legacy, and life beyond the mayor’s office
    Connect with Mayor Buddy at:
    X: https://x.com/orlandomayor

    Website: https://www.orlando.gov/Our-Government/Mayor-City-Council/Buddy-Dyer

    -----------------------------------
    Listen to more episodes of The B-Student Podcast wherever you get your podcasts.

    Like this video, subscribe, and comment your favorite London spot or what city has most transformed you.
    -----------------------------------
    Connect with Betsy Gardner:
    Website: https://www.betsygardner.com/

    Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/
    --------------------------------
    Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/


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    41 分
  • 45. The "Only You" Rule: Rollins President Brooke Barnett on the Future of Higher Ed

    45. The "Only You" Rule: Rollins President Brooke Barnett on the Future of Higher Ed
    2026/04/08
    On this episode of the B Student podcast, host Betsy Gardner sits down with Brooke Barnett, the 16th President of Rollins College, for a powerful conversation at the intersection of leadership, higher education, and the future of work.

    Just months into her role, Brooke offers a behind-the-scenes look at what it truly means to lead a modern institution in a time of rapid change, where AI, shifting workforce demands, and declining trust in traditional systems are reshaping everything we thought we knew about education.

    Together, they explore the evolving value of a liberal arts education, the role of storytelling in leadership, and why “human skills” like critical thinking, discernment, and communication may be the most valuable currency in the future.

    And stick around to the very end for an exclusive reveal of Fox Day 2026!


    This episode is a masterclass in leadership, innovation, and authenticity for anyone navigating complexity in today’s world.

    Time Stamps:
    00:00 Intro + Meet Rollins College President Brooke Barnett
    03:15 Leading Higher Ed in a Time of Disruption (AI + Workforce Shifts)
    06:30 Why Liberal Arts Still Matter More Than Ever
    09:45 Storytelling vs. “Just Giving Examples” in Leadership
    13:10 The Power of Place-Based Education (Why Rollins Stands Out)
    16:25 Preparing Students for the Future of Work
    19:40 Is College Still Worth It? Breaking the Trust Gap
    23:00 Barriers to Innovation (And How Leaders Miss Them)
    26:20 How to Challenge “We’ve Always Done It This Way”
    29:10 CEO Mindset: Focus on What Actually Matters
    32:00 Leadership Lessons from the President’s Seat
    35:00 Authenticity as a Leadership Superpower
    38:00 Final Takeaways + The Future of Higher Ed

    Connect with Brooke at:
    Linkedin: https://www.linkedin.com/in/brooke-barnett-65a74592/
    Website: https://www.rollins.edu/

    -----------------------------------
    Listen to more episodes of The B-Student Podcast wherever you get your podcasts.

    Like this video, subscribe, and comment your favorite London spot or what city has most transformed you.
    -----------------------------------
    Connect with Betsy Gardner:
    Website: https://www.betsygardner.com/

    Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/
    --------------------------------
    Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/

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    39 分