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.

Podcast Topic: Practical Skills

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.…

Extras #20 – Anger As Messenger – with Mollie West Duffy, Chrystal Bell & Ali Schultz

Extras 20 // March 8, 2023

Extras #20 – Anger As Messenger – with Mollie West Duffy, Chrystal Bell & Ali Schultz

What is your relationship to anger? For many of us, anger is information. Often, it tells us when an important boundary has been crossed or alerts us when a value…

Wisdom for Work #13 – Accountability & Trust

Wisdom for Work 13 // February 14, 2023

Wisdom for Work #13 – Accountability & Trust

We often say trust is one person’s assessment of another person’s competence, sincerity, and reliability. Accountability is a related concept to trust, but it’s also an inside job. Being accountable…

Podcast Topic: Practical Skills