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

#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…

Operator’s Manual #5 – Adaptive Leadership

Ops Manual 5 // February 1, 2023

Operator’s Manual #5 – Adaptive Leadership

Adaptive leadership is the notion that a fixed leadership style isn’t a quick fix or one-stop-shop for all your leadership needs. Adaptive leadership asks you to be keen enough to…

Extras #17 – Prep for Career Shifts and Job Changes – with Keith McAllister

Extra 17 // November 23, 2022

Extras #17 – Prep for Career Shifts and Job Changes – with Keith McAllister

Whether we decide to leave our job, make a career move, or unexpectedly find ourselves without a job, the space between secure positions elicits a lot of things–unprocessed fresh feelings,…

Wisdom for Work #12 – Collective Planning as a Leadership Team – with Andy Crissinger & Jerry Colonna

Wisdom for Work 12 // July 16, 2022

Wisdom for Work #12 – Collective Planning as a Leadership Team – with Andy Crissinger & Jerry Colonna

When considering collective planning as a team, what are the best practices leaders should adopt and what common pitfalls should they avoid? In this Wisdom for Work, Andy Crissinger and…

Podcast Topic: Practical Skills