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by Betsy Gardner
The B Student Podcast is hosted by Betsy Gardner, the President and CEO of the Winter Park Chamber of Commerce. The podcast focuses on exploring the "B side" of influential and dynamic professionals. Just like the B-side of a record, where deeper, more personal passions often live, this podcast highlights the less publicized yet deeply impactful aspects of these individuals' work and lives. Betsy brings her extensive experience as a CEO, speaker, consultant, and executive coach to dive into conversations with experts from diverse fields. The goal is to provide listeners with actionable insights, strategies, and inspiration to help them succeed and create meaningful impact in their own careers and communities. Each episode introduces listeners to unique perspectives and lessons on topics like leadership, emotional intelligence, community building, and personal growth—empowering the audience to "be" more successful and impactful in their own lives. About the host: Betsy Gardner is a dynamic leader with a diverse professional background. Since January 2017, she has served as the President and CEO of the Winter Park Chamber of Commerce, where she has been instrumental in modernizing the organization and implementing innovative programs to support local businesses and the community. Under her leadership, the chamber has received national recognition, including the North American Chamber Innovation Grand Prize, surpassing larger chambers such as Greater Boston and Vancouver. Before her tenure at the chamber, Gardner co-founded Longwave Apparel Ltd. in London, a company specializing in luxury UV-protective swimwear. She also served as the Director of Business Development for Mentore Consulting Ltd., focusing on mentoring programs for women in leadership roles. A native of Winter Park, Florida, Gardner holds a degree in History from the University of Florida, where she was recognized for her leadership and academic achievements. She is passionate about community development and has been involved in various initiatives, such as "Relaunch: Career Re-entry for Professional Women," which assists women returning to the workforce. She is also known for advocating for important issues and her efforts to make the chamber's programming more inclusive and relevant. Her leadership style is characterized by a strong bias toward action, strategic clarity, and a commitment to driving transformative revenue growth and innovation. She is dedicated to building diverse and inclusive teams and is recognized for her ability to energize cross-functional teams to consistently outperform targets.
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- Jun 24, 202641 min
55. From Homeless to Helping 20,000 People a Month | Stephanie Bowman | B Student
Stephanie Bowman survived severe domestic violence, battled addiction, experienced homelessness with her two kids, and eventually lost custody of her children. But her story didn't end there. Today, she is the Founder and CEO of One Heart for Women and Children, an organization that feeds and supports over 20,000 people in Central Florida every single month.In this episode of the B Student podcast, host Ashley Billings sits down with Stephanie for a raw, honest look at what it takes to rebuild your life from nothing. Stephanie shares the daily realities of recovery, what it’s like to start a massive community movement with zero money or business plan, and the unbelievable, true story of how a stolen trailer unexpectedly became the catalyst for a million-dollar campaign.If you are going through a dark season, trying to launch a passion project, or just need a reminder of what human resilience looks like, listen to this conversation.What we discuss in this episode:The reality of escaping domestic violence and surviving on the streets with two children.Navigating addiction recovery, the foster care system, and finding the confidence to start over.How to launch a thriving nonprofit when you have no funding, no building, and no business plan.Breaking the stereotypes around food insecurity in Central Florida and helping those who need it.The wild story of the stolen trailer that completely changed the trajectory of One Heart.Time Stamps: Meet Stephanie Bowman and the mission of One Heart for Women and Children The Victory Cup journey and 11 years of persistence Building relationships that fueled a million-dollar campaign Feeding families with dignity and ending hunger in Central Florida Escaping domestic violence and becoming homeless with two children Addiction recovery, foster care, and rebuilding her life Faith, mentorship, and finding the courage to move forward Starting a nonprofit with no money, building, or business plan The stolen trailer that unexpectedly changed everything Serving 20,000 people a month and the realities of food insecurity Breaking stereotypes about who needs help Stephanie's message of hope for anyone facing their darkest season-----------------------------------Listen to more episodes of The B-Student Podcast wherever you get your podcasts.-----------------------------------Connect with our Guests at:LinkedIn: https://www.linkedin.com/in/stephanie-bowman-8484998/?isSelfProfile=falseWebsite: https://bstephanie.com/Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/--------------------------------Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
- Jun 17, 202635 min
54. What Hiring Managers Really Think About Your Career Gap
If you've taken a break from the workforce, you’ve probably worried about how to explain the empty space on your resume. But do career gaps actually hurt your chances of getting hired, or could they be the exact thing that makes you stand out?In this episode of B Student: Summer School, Ashley Billings hosts a live panel discussion with Central Florida employers - including The Mayflower at Winter Park, Orlando Health Winnie Palmer Hospital for Women and Babies, Florida Blue, and The Bar Method Winter Park - and hiring leaders to pull back the curtain on modern workforce trends. As artificial intelligence changes how businesses operate, recruiters are looking for the exact human skills that technology can’t replicate, like emotional intelligence, adaptability, and resilience.The panel shares honest feedback on why a career pause to raise children, care for family, or navigate a major life transition doesn't diminish your professional value. In fact, it often builds the exact leadership experience today's companies are looking for.What we discuss in this episode:The shifting reality of how hiring managers view resume gapsWhy soft skills and emotional intelligence matter more than ever in an AI worldTurning volunteer work and life transitions into professional leadership experienceHow to build confidence and own your story when returning to the workforceBehind the scenes of the Relaunch mock interview experienceActionable advice for women and younger professionals entering a competitive job marketTime Stamps:-00:00 - Why Career Gaps Are More Valuable Than You Think-02:35 - Meet the Employers Behind the Panel-05:12 - What Stands Out in Today's Hiring Process-07:48 - Why Initiative Matters More Than Resumes-10:15 - The Soft Skills Employers Want Most-13:08 - What AI Can’t Replace in the Workplace-15:52 - How Career Pauses Build Leadership Skills-18:40 - Volunteer Work as Professional Experience-21:25 - What Employers Love About Relaunchers-24:10 - The Confidence Advantage of Life Experience-26:58 - Inside the Relaunch Mock Interview Experience-29:12 - Advice for Younger Professionals Entering the Workforce-31:35 - Why Relaunch Changes Lives-33:18 - What Employers Really Think About Career Gaps-34:45 - Final Encouragement for Women Returning to Work-----------------------------------Listen to more episodes of The B-Student Podcast wherever you get your podcasts.-----------------------------------Connect with our Guests at:Taylor Womack: https://www.linkedin.com/in/taylor-mckenzie-womack-855b68b5/The Mayflower at Winter Park: https://www.linkedin.com/company/the-mayflower-at-winter-park/Joshua Montemayor: https://www.linkedin.com/in/joshua-montemayor-647a7a24a/Orlando Health: https://www.linkedin.com/company/orlando-health/Karl Davis: https://www.linkedin.com/in/karl-davis-b7489b84/Florida Blue: https://www.linkedin.com/company/florida-blue/Karen Moreno: https://www.linkedin.com/in/karen-moreno-59317735/The Bar Method Winter Park: https://barmethod.com/locations/orlando-winter-park/Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/--------------------------------Podcast produced by Hi Hello Labs: <a href="https://url.avanan.click/v2/r01/___https://www.hihellolabs.com/___.YXAzOndpbnRlcnBhcms6YTpvOjc1N2I2YjkxNjlhMTRkMmQyZDNiYjM2NjAxNjVmOTJlOjc6NjE0Nzo5YzkyNTgyNThlYzE1OWNjNzE0ZDhjODJiNTdjOTc0NGMzNDJiOGYzNzFjNmMxMWQzN2Q3MGVjZDhmMmJlYzU2Omg6VDpO" target="_blank" rel="noreferrer noopen
- Jun 10, 202635 min
53. From Launching Old Navy & PINK to Building a Local Coffee Shop | Tracy Liffey | B Student
Tracy Liffey spent years helping launch some of the most iconic retail brands in the world, including Old Navy and PINK by Victoria's Secret, eventually overseeing creative teams of more than 100 people. But despite a highly successful corporate career, she chose to make a major pivot. Today, she is the founder of New General Café, a beloved clean food and coffee brand in Winter Park, Florida.In this episode of the B Student podcast, host Ashley Billings sits down with Tracy to talk about what it takes to leave corporate America and build a business from scratch. Tracy shares an honest look at the identity shift that happens when you leave a major job, the daily realities of entrepreneurship and working motherhood, and how to build a business that values community and connection over quick trends.Throughout this episode, Tracy shares:The realities of walking away from an executive corporate careerBehind-the-scenes lessons from launching global brands like Old Navy and PINKLearning a completely new industry from scratch and building New General CafeHow to listen to your customers and pivot when things get tough (including navigating COVID)The identity shift that comes with leaving a successful career to start overBalancing the demands of entrepreneurship with working motherhoodPractical advice for anyone navigating a major career transition or launching a small businessTime Stamps: Welcome to The B Student Podcast How New General became a community hub Leaving corporate America to be more present The original vision for New General Cafe Listening to customers and pivoting fast Creating healthier coffee and food options Learning the food and beverage business Building with community support in Winter Park Navigating COVID as a small business The reality of entrepreneurship as a working mom Lessons from Gap, Old Navy, PINK, and Victoria’s Secret Advice for women considering a career pivot-----------------------------------Listen to more episodes of The B-Student Podcast wherever you get your podcasts.-----------------------------------Connect with our Guest:LinkedIn: @tracy-brand-liffeyWebsite: https://www.newgeneral.us/Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/--------------------------------Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ #BStudentPodcast #WinterParkFL #NewGeneral #WomenInBusiness #CorporatePivot #Entrepreneurship #OldNavy #VictoriasSecretPINK #SmallBusinessOwner #CareerTransition
- Jun 3, 202631 min
52. 25 Years at Disney: Leadership Lessons & Career Reinvention with RK Kelley
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 Podcast02:01 What Is the Central Florida Pledge?04:26 Why RK Kelley Chose a Purpose-Driven Career06:45 How Businesses Can Get Involved09:12 Creating Respectful Dialogue Across Differences11:35 The Biggest Challenge Facing Communities Today13:57 A Vision for Central Florida's Future16:20 Why Listening Is a Critical Leadership Skill17:42 Lessons Learned from 25+ Years at Disney20:35 The Relaunch Program and Career Reinvention24:15 Mentorship, Self-Doubt, and Growth28:08 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-kelleyLearn More about Winter Park Chamber of Commerce: https://www.winterpark.org/--------------------------------Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
- May 27, 202629 min
51. The Soft Skills AI Can’t Touch: Career Success & Real Estate with Courtney Pelfrey
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 Story02:12 – Why She Left Higher Education for Real Estate04:48 – Building a Family-Owned Real Estate Business05:31 – Why Closing on a Home is Like Bringing Home a Baby07:15 – Working With Family: Strengths, Roles & Dynamics09:42 – Creating a Relationship-Driven Real Estate Brand12:18 – The Emotional Side of Buying & Selling Homes14:36 – How Career Services Prepared Her for Real Estate17:08 – The Reality of Working Motherhood & Flexibility19:45 – Balancing Business, Kids & Boundaries at Home22:04 – Social Media, Branding & Standing Out in Real Estate24:26 – Advice for Young Realtors Starting Their Careers26:18 – Why Curiosity Is a Powerful Leadership Skill That AI Can’t Replace28:10 – 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/
- May 20, 202636 min
50. How to Return to Work After a Career Break (With Confidence)
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 overWhy women struggle with confidence after a career break (and how to rebuild it)How to update your resume, LinkedIn profile, and personal brand for reentryThe 3 drivers of every career decision: control, content, and compensationWhy forward-thinking employers are actively hiring career returnersThe leadership and soft skills that make returning women high-value hiresThis episode is for you if:You're woman considering returning to work after time off for family, caregiving, or personal reasonsYou're mid career-transition and need a confidence resetYou're an HR leader or employer looking to hire experienced returning professionalsTimestamps: Introduction + Betsy Gardner and the Relaunch program The origin of the Relaunch program The business case for hiring women returning to the workforce Why women leave the workforce and struggle to return The confidence gap after a career break Betsy's personal career reentry story What Relaunch teaches (branding, resumes, LinkedIn) The psychology of returning to work after years away Control, content, compensation: the 3 Cs of starting a job How employers should view resume gaps in 2026 The hidden skills career returners bring to the workplace 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.comInstagram: https://www.instagram.com/thebetsygardnerYouTube: @humanintheroompodcastLearn More about Winter Park Chamber of Commerce: https://www.winterpark.org/--------------------------------Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
- May 14, 202626 min
49. Why Creativity and Curiosity Matter in Leadership | Jennifer Deery | B Student
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 reinventionLeadership lessons from corporate and nonprofit spacesWhy arts and culture matter to local economiesThe impact of museums and cultural institutionsThe story and legacy of sculptor Albin PolasekCreativity, curiosity, and lifelong learningHow art inspires innovation and community connectionWinter Park’s thriving arts and culture sceneStroke awareness and resilience through creativityAdvice for young creatives and aspiring leadersJennifer 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 Museum02:08 – Childhood influences, travel, and discovering museums04:12 – Jennifer’s first year leading the museum06:18 – The future vision for the Polasek Museum08:03 – Transitioning from board member to Executive Director10:38 – Why arts and culture are economic drivers in Winter Park13:02 – Collaboration between local museums and cultural organizations15:02 – Jennifer’s career path from art school to corporate leadership17:20 – Creativity, psychology, and leadership in business18:55 – Museum tourism and attracting visitors from around the world20:02 – Upcoming exhibits, events, and community programming23:24 – Albin Polasek’s resilience after stroke & advice for creativesListen 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-deeryInstagram: 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/
- May 6, 202630 min
48. She Quit Law Twice, Then Invented a Water Scooter | B Student | Lindsay Kiley
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 againThe Campable startup experiment and what it taught herEntrepreneurship while raising kids, the parts nobody posts aboutHow Swelly went from a garage idea to retail shelvesWhat she'd tell anyone who feels like they've missed their windowIf 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 #businesspodcastTime Stamps:00:00 Introduction + Meet Lindsay Kiley02:45 Leaving Law + Entering the Unknown05:30 Trying Again (And Why It Still Didn’t Fit)08:10 Failed Paths: Campable + In-House Role10:50 Starting Over Without a Plan13:30 Building Resilience + Not Giving Up16:00 Mom Life + Returning to Work18:45 Entrepreneurship While Raising Kids21:30 Launching Swelly + First Wins24:00 Expanding the Brand + New Products26:30 Overcoming Fear + Stepping Outside Comfort Zone29:30 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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About B Student Podcast
The B Student Podcast is hosted by Betsy Gardner, the President and CEO of the Winter Park Chamber of Commerce. The podcast focuses on exploring the "B side" of influential and dynamic professionals. Just like the B-side of a record, where deeper, more personal passions often live, this podcast highlights the less publicized yet deeply impactful aspects of these individuals' work and lives. Betsy brings her extensive experience as a CEO, speaker, consultant, and executive coach to dive into conversations with experts from diverse fields. The goal is to provide listeners with actionable insights, strategies, and inspiration to help them succeed and create meaningful impact in their own careers and communities. Each episode introduces listeners to unique perspectives and lessons on topics like leadership, emotional intelligence, community building, and personal growth—empowering the audience to "be" more successful and impactful in their own lives. About the host: Betsy Gardner is a dynamic leader with a diverse professional background. Since January 2017, she has served as the President and CEO of the Winter Park Chamber of Commerce, where she has been instrumental in modernizing the organization and implementing innovative programs to support local businesses and the community. Under her leadership, the chamber has received national recognition, including the North American Chamber Innovation Grand Prize, surpassing larger chambers such as Greater Boston and Vancouver. Before her tenure at the chamber, Gardner co-founded Longwave Apparel Ltd. in London, a company specializing in luxury UV-protective swimwear. She also served as the Director of Business Development for Mentore Consulting Ltd., focusing on mentoring programs for women in leadership roles. A native of Winter Park, Florida, Gardner holds a degree in History from the University of Florida, where she was recognized for her leadership and academic achievements. She is passionate about community development and has been involved in various initiatives, such as "Relaunch: Career Re-entry for Professional Women," which assists women returning to the workforce. She is also known for advocating for important issues and her efforts to make the chamber's programming more inclusive and relevant. Her leadership style is characterized by a strong bias toward action, strategic clarity, and a commitment to driving transformative revenue growth and innovation. She is dedicated to building diverse and inclusive teams and is recognized for her ability to energize cross-functional teams to consistently outperform targets.
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