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: Investors

#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.…

#146 – The Cost of Failure – with Tom Eisenmann

Episode 146 // June 15, 2021

#146 – The Cost of Failure – with Tom Eisenmann

What are the factors that contribute to the failure of almost 90% of startup ventures? In this episode, Jerry sits down with author and Harvard Business School professor Tom Eisenmann…

Wisdom for Work #9 – Navigating Power Differences To Build Better Relationships – with Andy Crissinger & Dan Putt

Wisdom for Work 9 // May 18, 2021

Wisdom for Work #9 – Navigating Power Differences To Build Better Relationships – with Andy Crissinger & Dan Putt

In our coaching practice, one of the most common questions we receive from investors is, “How do I build more trusting and impactful relationships with leaders in my portfolio?” As…

#141 – What Is My Work To Do? – with Nathan Lustig

Episode 141 // February 16, 2021

#141 – What Is My Work To Do? – with Nathan Lustig

After spending the last seven years routinely moving from country to country in Latin America, Nathan Lustig’s nomadic life was upended when the Coronavirus pandemic began to grip the entire…

#119 – Investing in Trust – with Fred Wilson (re-release)

Episode 119 // February 14, 2020

#119 – Investing in Trust – with Fred Wilson (re-release)

In 19 years of friendship and partnership in the startup world, Jerry and Fred Wilson have seen just about everything.  In this conversation, they share some stories from the Flatiron…

#113 – Invest in Being Yourself – with Bryce Roberts & Chris Marks

Episode 113 // September 26, 2019

#113 – Invest in Being Yourself – with Bryce Roberts & Chris Marks

VC’s Bryce Roberts of OATV and Indie.vc, and Chris Marks of Blue Note Ventures both found the standard issue of the VC world was not a fit for them.  They…

#111 – Standing in the Gap – with Amy Nelson (re-release)

Episode 111 // August 29, 2019

#111 – Standing in the Gap – with Amy Nelson (re-release)

Although the challenges women leaders face today have been well documented and highly publicized and most of us recognize that women are often forced to tackle unique and disproportionate challenges…

#103 – What Kind of Company Do You Want to Work For? – with Chris Savage & Brendan Schwartz

Episode 103 // April 26, 2019

#103 – What Kind of Company Do You Want to Work For? – with Chris Savage & Brendan Schwartz

For entrepreneurs today, advice on the ‘best practices’ for building a fruitful company abound – prescriptions for raising capital, increasing revenue, and hiring the correct team are often just a…

Podcast Topic: Investors