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 #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…

Extras #21 – Climbing Out of the Pits of Despair – with Mollie West Duffy & Liz Fosslien

Extras 21 // June 6, 2023

Extras #21 – Climbing Out of the Pits of Despair – with Mollie West Duffy & Liz Fosslien

Content warning: This podcast contains conversations around self-harm and suicidal ideation.  The pit of despair is a tough and tricky place. How can you find a way through when it…

#165 – The Bones of Belonging – with Annahid Dashtgard

Episode 165 // May 23, 2023

#165 – The Bones of Belonging – with Annahid Dashtgard

In this episode of the Reboot Podcast, Jerry sits down with Annahid Dashtgard, a fellow author, activist, and champion for justice, equity, diversity, and inclusivity. The pair discuss Annahid’s latest…

#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…

Wisdom for Work #15 – Navigating Conflict & Difficult Conversations – with Chris VandenBrink & Andy Crissinger

Wisdom for Work #15 // April 18, 2023

Wisdom for Work #15 – Navigating Conflict & Difficult Conversations – with Chris VandenBrink & Andy Crissinger

If you work with people, odds are good that hard conversations will be part of your work life. Whether it’s firing an employee or dealing with tension in the executive…

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.…

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