11 March 2026
41. Orlando Magic’s Ryan DeVos on Legacy, Leadership & The Future of Sports
B Student Podcast
About
In this episode of the B-Student Podcast, Betsy sits down with Ryan DeVos, Managing Director of the Orlando Magic, for a candid conversation about legacy, leadership, and building something new without abandoning what came before.
Ryan opens up about what it was like to grow up carrying the DeVos name, why he chose Orlando to “spread his wings,” and how he learned to lead with humility while building trust in high-stakes environments. They explore Ryan’s approach to innovation inside legacy organizations, including launching Magic Gaming and stepping into emerging spaces like Major League Pickleball with the Orlando Squeeze, and co-creating the elevated social club experience behind Hamlin House.
This is a conversation about responsibility and opportunity, entrepreneurship with a seventh-generation mindset, and the real discipline of prioritizing family while building a career at the intersection of sports, community, and business.
Time Stamps:
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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.
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Connect with Betsy Gardner:
Website: https://www.betsygardner.com/
Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/Pre-order your copy of Human in the Room today! Use code BSTUDENT through Friday, March 27 to receive 10% off.
Books can be preordered at humanintheroombook.com.
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Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/
Ryan opens up about what it was like to grow up carrying the DeVos name, why he chose Orlando to “spread his wings,” and how he learned to lead with humility while building trust in high-stakes environments. They explore Ryan’s approach to innovation inside legacy organizations, including launching Magic Gaming and stepping into emerging spaces like Major League Pickleball with the Orlando Squeeze, and co-creating the elevated social club experience behind Hamlin House.
This is a conversation about responsibility and opportunity, entrepreneurship with a seventh-generation mindset, and the real discipline of prioritizing family while building a career at the intersection of sports, community, and business.
Time Stamps:
- 00:00 Preorder Reminder: Human in the Room01:05 Welcome Ryan DeVos (First Podcast as a Guest)03:00 Growing Up DeVos: Legacy, Pressure, and the “Fishbowl”06:10 Why Orlando and Rollins: Spreading His Wings08:30 Introvert to “Trained Extrovert”10:20 Building a New Lane Inside a Legacy Organization12:25 Failure Tolerance as the Precursor to Innovation15:00 Family Ethos: Risk, Entrepreneurship, and Responsibility17:20 Magic Gaming: Why the NBA 2K League Made Sense20:10 How Ryan Built Trust and Credibility Early On23:05 Opportunity + Responsibility and Seventh-Generation Thinking26:10 Family First: Choosing a Different Path and Prioritizing Kids29:10 Pickleball Play: Orlando Squeeze + Why It’s Growing Fast32:20 Hamlin House: Elevating the Club Experience and Community35:30 What’s Next: Managing Director Role and Focus for the Future36:35 Where to Find Ryan + Hamlin House + Orlando Squeeze
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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/Pre-order your copy of Human in the Room today! Use code BSTUDENT through Friday, March 27 to receive 10% off.
Books can be preordered at humanintheroombook.com.
--------------------------------
Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/