He Lost His Son & Failed 30 Times — What He Learned About Leadership
May 1, 2026
Jason Reed built a company from his second bedroom into a 3,500-employee business with five brands across the nation. He's coached CEOs for 15 years, failed at over 30 companies, and lost tens of millions of dollars along the way.
But in March of 2018, Jason experienced the loss no parent should ever face — his 14-year-old son took his own life.
That moment changed everything. It changed how he leads, how he shows up for his people, and why he now dedicates his life to making sure no other parent misses what he missed.
In this episode of The Impactful Leader, host Chris sits down with Jason to talk about:
- Why he calls himself a "builder of people" — not a CEO
- What 30+ business failures taught him that success never could
- "Failure is an event, not an identity" — how to bounce back without losing yourself
- Why discipline and written goals separate leaders from dreamers
- The signs of mental health struggles he wishes he'd recognized sooner
- Why frontline managers MUST be equipped for mental health conversations
- How leading with vulnerability creates stronger teams — and real ROI
- "Do your employees want to give you a hug? If not, you're doing something wrong."
This is one of the most honest conversations we've ever had on this podcast.
Jason Reid shares how personal loss reshaped his mission, turning storytelling into a powerful tool for mental health awareness, workplace wellness, and deeper parent-child conversations.
In Episode 228 of the Say It Skillfully® podcast, Molly welcomes back storyteller, entrepreneur, and founder of Tell My Story , Jason Reid. After the tragic loss of his 14-year-old son Ryan to suicide in 2018, Jason transformed unimaginable grief into a mission to help families better understand youth mental health and create spaces where young people feel seen, valued, and supported. In this powerful and deeply human conversation, Jason shares the inspiration behind his new film Shift: Do What Moves You , which highlights how purpose, passion, and personal interests can help young people rise above depression and anxiety. The discussion explores the importance of creating safe conversations around mental health, the role of parents in supporting their children’s emotional wellbeing, and why having a hobby or passion outside of work or school can be life-changing. Jason also reflects on personal growth, the power of curiosity, and why learning about emerging technologies like AI is essential in a rapidly changing world. From parenting insights to leadership lessons, this episode is filled with practical wisdom for anyone seeking to live more intentionally and help others do the same. Jason’s message is both hopeful and practical: finding what moves you—and encouraging others to do the same—can create profound change in both individual lives and communities.
In Episode 228 of the Say It Skillfully® podcast, Molly welcomes back storyteller, entrepreneur, and founder of Tell My Story , Jason Reid. After the tragic loss of his 14-year-old son Ryan to suicide in 2018, Jason transformed unimaginable grief into a mission to help families better understand youth mental health and create spaces where young people feel seen, valued, and supported. In this powerful and deeply human conversation, Jason shares the inspiration behind his new film Shift: Do What Moves You , which highlights how purpose, passion, and personal interests can help young people rise above depression and anxiety. The discussion explores the importance of creating safe conversations around mental health, the role of parents in supporting their children’s emotional wellbeing, and why having a hobby or passion outside of work or school can be life-changing. Jason also reflects on personal growth, the power of curiosity, and why learning about emerging technologies like AI is essential in a rapidly changing world. From parenting insights to leadership lessons, this episode is filled with practical wisdom for anyone seeking to live more intentionally and help others do the same. Jason’s message is both hopeful and practical: finding what moves you—and encouraging others to do the same—can create profound change in both individual lives and communities.
In this episode of The Amanda Kaufman Show, I’m joined by Dana Christian Lee for a deeply human conversation about mental health, storytelling, and why asking a different question can change everything. Instead of starting with what’s broken, Dana invites us to start with presence. With curiosity. With the question: What moves you? We talk about why film opens conversations that advice often can’t, how young people experience pressure and disconnection, and why so many adults lose touch with what actually lights them up. This is a conversation about shifting from performance to presence, from problem-focused thinking to possibility, and from managing life to actually feeling it again. If you care about mental health, connection, or creating spaces where people feel seen without being fixed, this episode will stay with you. Ways to Connect with Dana Christian Lee Website https://www.tellmystory.org/ LinkedIn / tellmystory-org Facebook / 1tellmystory
This episode welcomes Dana Christian Lee, Executive Director of Tell My Story, an organization dedicated to suicide prevention and fostering authentic conversations between young people and their families. Dana discusses her own mental health journey, the heartbreaking loss that inspired Tell My Story, and the organiza
In this episode of The Amanda Kaufman Show, I’m joined by Dana Christian Lee for a deeply human conversation about mental health, storytelling, and why asking a different question can change everything. Watch the full video here
In this episode, I’m joined by Jason Reid, an entrepreneur, father, and founder of Tell My Story, an organization dedicated to transforming how families, schools, and communities talk about mental health.
A Father’s Loss That Became a National Mission
Today I’m talking with Jason Reid about one of the hardest parts of parenting: having real, honest conversations with our kids about the things nobody wants to bring up. The messy things. The scary things. The things we hope aren’t happening—but often are.
Join us for a powerful Say It Skillfully® livestream on youth mental health and the power of owning your story. Connect directly with Molly Tschang and special guest Jason Reid on your real-life questions about parenting, mental wellness, and how to create a culture where tough conversations save lives—live and unscripted.
