41. Orlando Magic’s Ryan DeVos on Legacy, Leadership & The Future of Sports

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41. Orlando Magic’s Ryan DeVos on Legacy, Leadership & The Future of Sports

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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:

00:00 Preorder Reminder: Human in the Room
01:05 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 Wings
08:30 Introvert to “Trained Extrovert”
10:20 Building a New Lane Inside a Legacy Organization
12:25 Failure Tolerance as the Precursor to Innovation
15:00 Family Ethos: Risk, Entrepreneurship, and Responsibility
17:20 Magic Gaming: Why the NBA 2K League Made Sense
20:10 How Ryan Built Trust and Credibility Early On
23:05 Opportunity + Responsibility and Seventh-Generation Thinking
26:10 Family First: Choosing a Different Path and Prioritizing Kids
29:10 Pickleball Play: Orlando Squeeze + Why It’s Growing Fast
32:20 Hamlin House: Elevating the Club Experience and Community
35:30 What’s Next: Managing Director Role and Focus for the Future
36:35 Where to Find Ryan + Hamlin House + Orlando Squeeze

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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/

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