What does it take to visit 192 countries, work alongside democracy activists on the front lines of history, and build a career around adventure and purpose? In this episode of the Agents of Innovation Podcast, host Francisco Gonzalez sits down with longtime friend Jess Yescalis, President of Yescalis Campaign Strategies, political strategist, fundraiser, and one of the most well-traveled people in the world. Jess has spent decades helping raise hundreds of millions of dollars for free-market causes while advising political leaders and pro-democracy movements across the globe. Along the way, he's worked with dissidents in Myanmar, trained parliamentary candidates in Egypt after the Arab Spring, navigated some of the world's most dangerous places, and pursued a personal goal of doing something fun or meaningful in every country on Earth. This conversation goes far beyond travel. It's about freedom, gratitude, leadership, courage, and the remarkable people Jess has met from every corner of the world. In this episode, you'll learn: * How Jess intentionally built a career that enables a life of global travel * What it's like working with democracy activists risking their lives for freedom * Stories from Egypt, Myanmar, Somalia, Central African Republic, and beyond * The biggest misconceptions about visiting nearly every country in the world * Why travel can change the way we see America—and ourselves * Lessons about human nature after meeting people from virtually every culture * Why most people, regardless of where they live, want the same basic things: freedom, opportunity, and hope The final five countries remaining on Jess's quest—and why two may have to wait Whether you're an entrepreneur, traveler, student of politics, or simply curious about the world, this episode offers a thoughtful perspective on living with purpose, embracing adventure, and appreciating the freedoms many of us take for granted. You can also watch this conversation on YouTube: https://youtu.be/RdEpXCxXuzs If you enjoyed this conversation, please subscribe to the Agents of Innovation Podcast, leave a review, and share this episode with someone who loves travel, entrepreneurship, or stories that inspire. Subscribe for more conversations with entrepreneurs, innovators, philanthropists, and artists who are shaping the future. Follow the Agents of Innovation podcast on: Instagram: / / innovationradio X: / https://x.com/agentinnovation Facebook: / / agentsofinnovationpodcast You can support this podcast and our Fearless Journeys community on our Patreon account: www.patreon.com/fearlessjourneys You can also join our network -- and our group trips -- through the Fearless Journeys community at: https://www.fearlessjourneys.org and subscribe to our free newsletter at: https://fearlessjourneys.substack.com Learn more: 🌍 Fearless Journeys: https://fearlessjourneys.org 00:00 Introduction 01:40 Visiting 192 Countries 03:10 Building an Intentional Life 04:50 Where the Travel Bug Began 06:40 When Travel Met the Fight for Freedom 08:10 Working with Dissidents in Myanmar 12:35 From Campaigns to Democracy Work 15:05 Raising Hundreds of Millions of Dollars 20:15 Structuring a Life Around Travel 22:45 How Travel Changed Over Time 24:15 Chasing the World's Greatest Sporting Events 26:50 The Final Five Countries 30:05 Traveling in Dangerous Places 34:50 Egypt and the Arab Spring 40:10 Lessons from Central African Republic 44:20 The Scariest Travel Experience 47:00 Lifelong Friendships Around the World 50:30 What 192 Countries Taught Him 54:45 A Greater Appreciation for America 1:00:45 Traveling with Children 1:04:40 The Countries Still Left 1:05:40 What Happens After Country #197? 1:08:40 Advice for Aspiring Travelers 1:11:30 Jess's Annual Travel Calendar 1:13:45 Where to Connect with Jess 1:15:00 Closing Thoughts