From the Appalachian Trail to a Mission to End Homelessness | Stephen Jelinek #20

by | Jul 16, 2026 | Interview

Every life has a story—but some stories refuse to fit into a single chapter.
 
In this deeply personal conversation, Jeff Gould sits down with Stephen Jelinek, a veteran, entrepreneur, long-distance adventurer, and man of unwavering faith whose life has been marked by extraordinary highs and devastating lows.
 
Stephen shares stories of serving in a nuclear missile wing during the Cold War, hiking the entire Appalachian Trail, kayaking the length of the Mississippi River, ministering to the homeless, surviving divorce and depression, and facing the unimaginable loss of his son to murder. Through it all, he explains how faith has shaped his response to suffering and inspired his vision for “Highway Heaven,” an ambitious plan to provide purpose, work, and hope for people experiencing homelessness.
 
Topics include:
• Growing up under the influence of a remarkable grandfather
• Military service during the Cold War
• Depression, divorce, and rebuilding a life
• Living alongside the homeless and what most people never see
• Hiking the Appalachian Trail and kayaking the Mississippi River
• Forgiving the man who murdered his son
• The vision behind Highway Heaven
• Faith, purpose, resilience, and redemption
 
Whether you agree with every conclusion or not, this conversation offers an honest look at loss, forgiveness, perseverance, and the power of holding onto hope when life takes unexpected turns.
 
If this story resonates with you, please like the video, subscribe to the channel, and share it with someone who might need encouragement today.
 
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