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I thought I was going home to Chicago for baseball, family time, and the Chicago Marathon buzz. What I came back with was bigger: I got selected to run the South Africa Marathon in Cape Town, and it lit a fire I didn’t expect. This isn’t just a race update, it’s the start of a new long-form story I’m calling “From The South Side Of Chicago To South Africa,” where marathon training becomes a way to finally understand my own roots.

I’m sharing the conversations that shook me, starting with my cousin Gina and the grief our family has carried after losing her parents. We talk about my dad and my Uncle Henry growing up in Mississippi during the Jim Crow era, and what it does to a man when he’s taught to hide every emotion. Those stories made me look in the mirror and ask hard questions about how I show up as a husband, a father, and a son, and what I might be carrying that I never named.

I also get into my cousin Erica, childhood memories, and the health wake-up calls that come with losing people you love. Then I rewind to the South Side neighborhood bonds, the violence that still echoes, and a lunch with my dad that revealed family history I honestly didn’t know. Along the way, I talk identity, what it meant to be “mixed” where I grew up, and why the mental side of running might be the most important part of this whole journey.

If you’re into marathon motivation, family history, personal growth, and real conversations, come ride with me. Subscribe, share this with a friend, leave a review, and tell me this: what question would you ask your own family if you had the chance?

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This episode of That First Mile Podcast is all about what happens when running becomes a family affair.

Randy sits down with his wife, Lili, daughters Liliana and Juli, and Ryan to talk about their experience running Ragnar together as a family.

They talk about the miles, the laughs, the exhaustion, the unexpected moments, and what it was really like spending 200 miles together as a family. Ragnar is hard enough on your legs, but doing it with the people you love creates a completely different experience.

This isn’t just a story about running a relay. It’s about family, memories, pushing each other when things get tough, and realizing that sometimes the best miles are the ones you share with other people.

Family ties. Tired thighs. A whole lot of memories.

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What if the right pair of running shoes could change your life?

In this episode of That First Mile Podcast, we’re joined by Rosemary Rios, manager of Sole II Soul Sports in Visalia, CA, to talk about far more than shoes. We explore how proper shoe fitting can prevent injuries, build confidence, and help people take that very first step toward a healthier lifestyle.

Rosemary shares her journey into the running community, what she has learned from helping runners of every experience level, and why local running stores continue to play such an important role in bringing people together. We also discuss common mistakes runners make when buying shoes, how often they should be replaced, and what every new runner should know before lacing up.

Throughout the conversation, we reflect on the connection between running and mental health, the power of community, and how small steps can lead to life-changing transformations.

Whether you’re training for your first 5K, your next marathon, or simply looking for motivation to get moving, this episode is packed with practical advice and inspiration.

Thank you for listening to That First Mile Podcast. If this episode encouraged you, please follow the show, leave a review, and share it with someone who’s ready to take their own first mile.