The most in-depth startup podcast you’ll ever listen to.

Join Jerry Colonna and other members of Team Reboot as they go deep with entrepreneurs, CEOs, and startup leaders like you, exploring the emotional journeys we all face.

The most in-depth startup podcast you’ll ever listen to.

The Reboot Podcast showcases the heart and soul, the wins and losses, and the ups and downs of leadership.

Beyond spreadsheets and strategy lies the beating heart of leadership. The Reboot Podcast isn’t just about business; it’s about the soul of building something meaningful. Join Jerry Colonna and other members of Team Reboot as they go deep with entrepreneurs, CEOs, and leaders like you, exploring the emotional journeys we all face.

Forget the sanitized success stories. Here, we dive into the wins and losses, the triumphs and breakdowns, the moments where vulnerability and courage dance on the edge of the unknown.

Each episode is a raw conversation, a shared experience. From imposter syndrome to burnout, major transitions, anxiety, and even co-founder conflict, no challenge is off-limits. You’ll find laughter, tears, and moments of profound wisdom as you discover tools and strategies to navigate the emotional rollercoaster of being a leader to today’s complex world.

This isn’t just a podcast; it’s a community. Whether you’re seeking inspiration, practical tips, or simply a reminder that you’re not alone, we’re so glad you’re here.

Become a guest!

  • One of "the 12 Best Podcasts for Entrepreneurs...Forbes has sampled a whole bunch (of podcasts), and recommends these 12 as some of the best and most educational out there." ... view link

    Brian Solomon

    Brian Solomon

    Forbes (October, 2015)

  • “The Reboot Podcast has changed my life. It's like a release valve that I can pull on daily when I don't feel like I can meaningfully deal with my own concerns. The interviews and blog have helped me reach beyond what I thought was my capacity to be vulnerable and to love.”

    Tracy Lawrence

    Tracy Lawrence

    CEO of Chewse

  • “Holy crap your podcast is so amazing that I have to stop it and absorb what was said so I could think about it. I've had issues that were so tough for me to deal with that I looked away. But for founders, that's a haaard thing to admit. I savor your work guys. Thank you for making it.”

    Andrew Warner

    Andrew Warner

    Founder of Mixergy

  • "Your podcast came at the right moment. I am listening your advice line by line. And I understand what I did...Thank you Jerry. Your messages are like a lighthouse in the sea of startup life."

    Sooinn Lee

    Sooinn Lee

    CEO of Enuma

Recent Podcasts

#175 – Beyond the Self: Embracing Interconnectedness – with Luis Duarte

#175 // September 24, 2024

#175 – Beyond the Self: Embracing Interconnectedness – with Luis Duarte

Join Jerry and Luis Duarte for a thought-provoking conversation on the power of interconnectedness and the importance of finding purpose in our lives. Luis, a passionate entrepreneur and Founder of…

Extras #25 – The Power of Horses for Coach Development

Extras #25 // August 15, 2024

Extras #25 – The Power of Horses for Coach Development

In this Wisdom for Work episode, Ali sits down with Liz Stewart and Kelly Wendorf to talk about Reboot’s upcoming Coach Retreat, the value of coach supervision, and how working…

#174 – Leading With Love & Intention – with Dr. Nicole Marie Ortiz

#174 // August 27, 2024

#174 – Leading With Love & Intention – with Dr. Nicole Marie Ortiz

In a world where intentional action seems like a rarity, Nicole Ortiz, Director of Leadership and Belonging at the Denver Zoo, stands out with her deliberate approach to work and…

Wisdom for Work #25 – The Art of Generative Listening – with Miriam Meima

Wisdom for Work #25 // July 29, 2024

Wisdom for Work #25 – The Art of Generative Listening – with Miriam Meima

In this episode, Miriam Meima returns to explore the art of generative listening with Ali Schultz. They explore the significance of optimizing interactions, the pitfalls of selective listening, and the…

#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…

Wisdom for Work #23 – Cultivating Conditions of Courage

Wisdom for Work #23 // May 14, 2024

Wisdom for Work #23 – Cultivating Conditions of Courage

How can leaders create a safe space for honest conversations, even when those truths challenge the status quo? In this episode of Wisdom for Work, Reboot Coaches Ali Schultz and…

#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.…

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