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

#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.…

Wisdom for Work #22 – Owning Your Strengths – with Miriam Meima

Wisdom for Work #22 // April 16, 2024

Wisdom for Work #22 – Owning Your Strengths – with Miriam Meima

We all have that nagging voice in our head, the inner critic, that loves to point out our flaws. But what if there was a way to silence that bully…

Extras #24 – Building High-Performing Teams Through Coaching – with Steph Yiu

Extras 24 // April 5, 2024

Extras #24 – Building High-Performing Teams Through Coaching – with Steph Yiu

In this Podcast Extra, Andy Crissinger delves into the world of coaching and its transformative impact on corporate culture with guest Steph Yiu, Chief Customer Officer at WordPress VIP and…

Wisdom for Work #21 – Engaging Your Team to Bring Out Their Best – with Team Reboot

Wisdom for Work #21 // March 12, 2024

Wisdom for Work #21 – Engaging Your Team to Bring Out Their Best – with Team Reboot

How do you engage your team to bring out their best? In this Wisdom for Work, Reboot Coaches Andy Crissinger, Jen Cody, Jim Marsden, and Chris VandenBrink gather to explore…

Wisdom for Work #20 – The Art of Firing Well – with Heather Jassy & Ali Schultz

Wisdom for Work #20 // February 27, 2024

Wisdom for Work #20 – The Art of Firing Well – with Heather Jassy & Ali Schultz

If you’re a leader, few things can ruin your day more than needing to fire someone. It’s just plain hard to do, even when you know it’s the right decision.…

#170 – The Brave Leader’s Path: Fostering Inclusivity & Courageous Decision-Making – with David McQueen

#170 // February 5, 2024

#170 – The Brave Leader’s Path: Fostering Inclusivity & Courageous Decision-Making – with David McQueen

What does it mean to lead bravely? In this powerful episode, Jerry Colonna explores the essential elements of ethical leadership with David McQueen, author of “The Brave Leader.” David sheds…

Extras #23 – Unleashing Potential: Insights on Leadership, Self-Discovery, & Overcoming Fear – with Noah Kagan

Extras 23 // January 30, 2024

Extras #23 – Unleashing Potential: Insights on Leadership, Self-Discovery, & Overcoming Fear – with Noah Kagan

As a leader, how do you decide which inputs to listen to? What strategies do you use for personal growth and reflection? How do you create a work environment that…

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