Orlando Magic’s Ryan DeVos on Legacy, Leadership & The Future of Sports
Leading Through Family Values, Innovation and Hard Work
March 11, 2026
In this episode of the B Student podcast, Betsy Gardner sits down with Ryan DeVos, Managing Director of the Orlando Magic and founder of the Orlando Squeeze. Beyond the box scores and arena lights, Ryan reveals the "shirt-sleeves" philosophy that governs one of America’s most prominent sporting families, and the delicate balance of honoring a multi-generational legacy while navigating the high-growth frontiers of professional pickleball and NBA innovation.
Whether you are navigating a family business or leading a team in a competitive industry, these five takeaways from Ryan's conversation offer a roadmap for sustainable success. Here are our top moments from this week's episode of the B Student podcast:
1. Honor Your Legacy While Forging Your Own Path
Ryan DeVos knows the unique dynamic of acknowledging his own success while honoring his family's legacy, emphasizing that true leadership requires a delicate balance. His perspective is to respect the foundation built by the generations before him, while choosing not to simply live in its shadow. Instead, he uses that legacy as a launching pad to forge his own unique path forward and create impact - and recommends you do the same.
2. The 90% Rule: Prioritizing Family in a High-Pressure World
By the time children turn 18, parents have already spent about 90% of the in-person time they will ever share with them. As kids grow older, time together naturally decreases. Ryan's message is clear: prioritize family when you can, even if that means missing out on some work opportunities.
3. The "Shirt-Sleeves" Rule: Safeguarding the Future of Family Business
A family motto: "shirt-sleeves to shirt-sleeves in three generations" reflects a harsh business reality, a staggering 96% of family businesses fail by the time they reach the third generation. This is often due to a lack of protective structures and poor succession planning. However, DeVos emphasizes that this outcome is preventable through careful planning and teaching the next generation core values of working hard, being responsible and planning for the future.
4. Full Commitment: Why Success Requires Diving In Head First
True entrepreneurship demands unwavering risk tolerance and the willingness to fully commit. Ryan shares the incredible story of his grandfather launching a flight school for GIs returning from World War 2, despite neither founder actually knowing how to fly, followed by a drive-in diner. Both ventures ultimately failed. However, the critical lesson is that these failures weren't wasted efforts; they were the essential stepping stones that forged his entrepreneurial mindset. Successful leaders don't just cautiously test the waters; they dive in fully, understanding that embracing risk and inevitable failure is a mandatory part of success.
5. Relationship First, Trust Second: The Foundation of Authentic Connection
Trust cannot be demanded, assumed, or fast-tracked; it must be earned through genuine relationship-building. In this clip, DeVos emphasizes that without a solid relationship foundation, people can easily misperceive your character, your intentions, and your approach. These misperceptions are the ultimate enemy of credibility. True leaders understand that investing time in authentic, one-on-one relationships is mandatory for building the kind of trust that allows their vision and influence to actually resonate with their team, clients, or community.
Ready to dive deeper into the conversation?
Don't miss the full conversation! Catch the complete episode with Ryan DeVos on YouTube to hear firsthand how the next generation honors their family's legacy while innovating for the future. You can also listen and subscribe on Apple Podcasts, Spotify or wherever you get podcasts.
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