On this episode of Cowboy Shit, we’re joined by Filipe Masetti Leite—long rider, award-winning journalist, and the youngest person to cross the Americas on horseback.

Over 8 years, Filipe rode more than 16,000 miles through 12 countries, traveling from Alaska to Ushuaia, Argentina with 11 different horses. Along the way, he faced extreme terrain, isolation, and moments that tested his will to continue.

We talk about perseverance, resilience, leadership, and the powerful bond between humans and horses—plus what it takes to chase a dream when quitting feels easier. Filipe’s journey is now documented in his free film, The Long Rider, available on YouTube.

This episode is a reminder that the long way is sometimes the only way worth taking.

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