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.

Wisdom for Work #18 – Is Coaching Right for You? – with Dan Putt & Andy Crissinger

Wisdom for Work #18 // November 1, 2023

Wisdom for Work #18 – Is Coaching Right for You? – with Dan Putt & Andy Crissinger

A common question we get asked at Reboot is: How do I know if coaching is right for me?  In this episode, Reboot Coaches Dan Putt and Andy Crissinger delve…

#168 – ​​The Healing Power of Tears: Building Empathy and Connection in a Numb World – with Benjamin Perry

Episode 168 // Oct 17, 2023

#168 – ​​The Healing Power of Tears: Building Empathy and Connection in a Numb World – with Benjamin Perry

What is your relationship to crying? When was the last time you allowed yourself to weep openly? In this compelling episode of the Reboot Podcast, Jerry sits down with Benjamin…

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…

#167 – From Isolation to Openness: Engaging Fully with Real Life – with Sharon Salzberg

Episode 167 // August 25, 2023

#167 – From Isolation to Openness: Engaging Fully with Real Life – with Sharon Salzberg

When confronted with the realness of our lives, how we choose to respond matters. It’s no easy feat to turn toward suffering when the world around us gets messy. However,…

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…

Operator’s Manual #7 – When Should You Shut Down the Business?

Op's Man #7 // July 6, 2023

Operator’s Manual #7 – When Should You Shut Down the Business?

How do you know when it’s time to shut down the business? What does it take to come to this realization as the entrepreneur behind the wheel? In this Operator’s…

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…

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