The Reboot Podcast

The Reboot Podcast showcases the heart and soul, the wins and losses, and the ups and downs of leadership. Join Jerry Colonna and Reboot Coaches as they go deep with entrepreneurs, CEOs, and leaders like you, to explore the emotional journeys we all face.

The Reboot Podcast

Podcast Topic: Greater Resiliency

#180 – Navigating Darkness, Perfectionism & Purpose as an Entrepreneur – with Melissa Berstein

#180 // October 23, 2025

#180 – Navigating Darkness, Perfectionism & Purpose as an Entrepreneur – with Melissa Berstein

At the heart of entrepreneurship lies not just innovation and ambition, but a deeper journey of self-discovery, resilience, and embracing our most authentic selves. Entrepreneurship, often glamorized for its successes,…

#179 – The Work of Getting Free: Redemption, Gratitude & Hope – with Shaka Senghor

#179 // September 10, 2025

#179 – The Work of Getting Free: Redemption, Gratitude & Hope – with Shaka Senghor

In this episode of The Reboot Podcast, Jerry sits down with Shaka Senghor, author, mentor, and leading voice in criminal justice reform, for a tender conversation about transformation, freedom, and…

#177 – What Does It Mean To End Well? – with Randy Goodman

#177 // May 22, 2025

#177 – What Does It Mean To End Well? – with Randy Goodman

How do we navigate seismic shifts in our industries and our lives while striving to remain true to ourselves and those we care about? In this episode, Jerry sits down…

Wisdom for Work #26 – Staying Grounded Throughout the Work Day – with Miriam Meima

Wisdom for Work # 26 // December 3, 2024

Wisdom for Work #26 – Staying Grounded Throughout the Work Day – with Miriam Meima

Some days can get away from you before you sit down at your desk, while other days can be a slog. As our days pull us along or come at…

Extras #26 – Moving From Fragility to Robustness – with Kelly Wendorf

Extras 26 // October 30, 2024

Extras #26 – Moving From Fragility to Robustness – with Kelly Wendorf

Where are your delicate and vulnerable spots that, when touched, cause a defensive reaction? In this thought-provoking episode, Ali explores the concept of fragility with Kelly Wendorf, founder of Equus…

#173 – Celebrating Difference in Your Company – with Rob Castaneda

#173 // July 16, 2024

#173 – Celebrating Difference in Your Company – with Rob Castaneda

In this episode of The Reboot Podcast, Jerry sits down with Rob Castaneda, the founder and CEO of ServiceRocket. Together, they unpack the importance of empathy, fostering a sense of…

Wisdom for Work #24 – Unlocking Imposter Syndrome – with Miriam Meima

Wisdom for Work #24 // June 18, 2024

Wisdom for Work #24 – Unlocking Imposter Syndrome – with Miriam Meima

In this episode, Ali Schultz reunites with coach Miriam Meima for a heartfelt conversation about imposter syndrome. They move beyond simply acknowledging the phenomenon, and instead, share practical strategies for…

#172 – Finding Closure After Shutting Down the Business – with João Barros

#172 // June 4, 2024

#172 – Finding Closure After Shutting Down the Business – with João Barros

There’s more to leadership than building the next billion-dollar unicorn. Our guest, João Barros, has walked a fascinating path – from professor to CEO and back again. In this candid…

#171 – The Great Midlife Edit – with Chip Conley

#171 // April 30, 2024

#171 – The Great Midlife Edit – with Chip Conley

In this episode of The Reboot Podcast, Jerry Colonna sits down with the insightful Chip Conley, author of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age.…

Podcast Topic: Greater Resiliency