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: Practical Skills

Wisdom for Work #19 – Strategic Delegation: Building Trust & Setting Clear Expectations

Wisdom for Work #19 // Jan 9, 2024

Wisdom for Work #19 – Strategic Delegation: Building Trust & Setting Clear Expectations

Delegation is one of the most essential skills to master as a leader. Done well, it’s the fundamental behavior that impacts the culture, execution, and the bottom line. And, it…

#169 – Rupture + Repair = Resilience in Co-founder Relationships – with Lizzy Karp, Gill Damborg & Emma Devin

EPISODE 169 // December 8, 2023

#169 – Rupture + Repair = Resilience in Co-founder Relationships – with Lizzy Karp, Gill Damborg & Emma Devin

In today’s episode, Jerry Colonna engages in an insightful and deeply personal conversation with Emma, Gill, and Lizzy, the co-founders of Brood, a startup aiming to revolutionize modern family care.…

Wisdom for Work #17 – The Power of Retrospectives: Learning From the Past To Shape the Future – with Andy Crissinger

Wisdom for Work #17 // September 26, 2023

Wisdom for Work #17 – The Power of Retrospectives: Learning From the Past To Shape the Future – with Andy Crissinger

Retrospectives play a crucial role in building resilient teams. As organizations face constant change and uncertainty, having a regular ritual of collective learning provides stability and a sense of groundedness.…

Operator’s Manual #8 – The Arc of Dysfunction: From Unhealthy Chaos to Healthy Creativity

Ops Man #8 // September 12, 2023

Operator’s Manual #8 – The Arc of Dysfunction: From Unhealthy Chaos to Healthy Creativity

What exactly is the Arc of Dysfunction, and why is it important for all organizations, especially startups? From the unhealthy and dysfunctional beginnings to the healthy and dysfunctional apex, Jerry…

Wisdom for Work #16 – The Brightest Bulb Challenge – with Ray Foote & Andy Crissinger

Wisdom for Work #16 // August 1, 2023

Wisdom for Work #16 – The Brightest Bulb Challenge – with Ray Foote & Andy Crissinger

For individuals stepping more fully into leadership roles, the transition from individual contributor to team leader can bring about a myriad of feelings. What happens when you go from making…

#166 – We Can Choose to Ride the Roller Coaster of Entrepreneurship – with Jean Smart

EPISODE 166 // JULY 19, 2023

#166 – We Can Choose to Ride the Roller Coaster of Entrepreneurship – with Jean Smart

For leaders, navigating the roller coaster experience of entrepreneurship can be flat-out exhausting. The constant fluctuation of riding highs and surviving lows often leaves little time for reflection, much less…

Extras #22 – Scaling as a Technical Founder & CEO – with Evan Drumwright

Extras 22 // June 20, 2023

Extras #22 – Scaling as a Technical Founder & CEO – with Evan Drumwright

Being a technical founder poses particular challenges to scaling in your role as CEO. Scaling a company is challenging. Leading through that scale as your role as CEO is also…

#164 – How To Be a Stable Board Member – with Aileen Lee & Brad Feld

Episode 164 // May 5, 2023

#164 – How To Be a Stable Board Member – with Aileen Lee & Brad Feld

When markets are volatile and times are turbulent, being a VC can be a nerve-wracking experience. How should seasoned board members handle themselves when anxieties are high? In this podcast…

Operator’s Manual #6 – The Benefits of Bootstrapping

Operator's Manual #6

Operator’s Manual #6 – The Benefits of Bootstrapping

Ever wonder what happened to building a good ol’ profitable business? Maybe you wonder if there are benefits to bootstrapping in this world of high-growth, venture-backed companies with bloated valuations.…

Podcast Topic: Practical Skills