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.

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#156 – Safety and Trust: The Crux of Adult Relationships – with Brad Feld & David Jilk

Episode 156 // April 12, 2022

#156 – Safety and Trust: The Crux of Adult Relationships – with Brad Feld & David Jilk

At Reboot, we firmly believe that the act of leadership affords everyone the opportunity to grow into their most adult selves. Inquiring radically into our own psychologies and facing up…

#155 – The Heart of the Matter – with Dr. Simon Maltais

Episode 155 // March 6, 2022

#155 – The Heart of the Matter – with Dr. Simon Maltais

As the Coronavirus pandemic continues to shape our lives, many of us are flat-out exhausted. While this enduring moment in time has impacted us all, the prolonged nature of this…

#153 – Everyone Is Scalable – with Matt Blumberg

Episode 153 // January 11, 2022

#153 – Everyone Is Scalable – with Matt Blumberg

For our first episode of 2022, Jerry sits down with Matt Blumberg, founder and CEO of Bolster, a marketplace for on-demand executive and board talent. In this conversation, Matt describes…

Operator’s Manual #4 – On Modeling Self-care and Building the Machine

Ops Manual 4 // January 25, 2022

Operator’s Manual #4 – On Modeling Self-care and Building the Machine

In this episode of our Operators Manual series, Ali and Jerry consider how the health and resilience of an organization can be directly tied to the CEO’s own modeled behavior…

Operator’s Manual #3 – The Great Re-Examination: How Do You Want to Spend Your Minutes?

Ops Manual // Dec 14, 2021

Operator’s Manual #3 – The Great Re-Examination: How Do You Want to Spend Your Minutes?

The phrase, “The Great Resignation,” has become abundantly popular in the media over the recent months. In this episode, Ali and Jerry discuss how pandemic life has ushered forth larger…

Operator’s Manual #2 – What Does It Mean To Step Back and Let Others Lead?

Ops Manual 2 // Dec 2, 2021

Operator’s Manual #2 – What Does It Mean To Step Back and Let Others Lead?

The more we work with clients, the more we see leaders longing for pieces of wisdom around the parts of the job that aren’t necessarily in any playbook. In this…

#152 – Facts, Not Flaws – with Philip Deng

Episode 152 // November 4, 2021

#152 – Facts, Not Flaws – with Philip Deng

After a decade of working in non-profits, Philip Deng has decided to build something of his own. In this conversation, Philip sits down with Jerry to chat about his company…

Operator’s Manual #1 – What IS the Job of the CEO?

Ops Manual 1 // Nov, 18 2021

Operator’s Manual #1 – What IS the Job of the CEO?

We wanted to bring you a new-ish kind of conversation to our podcast channel – but not new to the halls of Reboot. This one is for the operators, where…

#151 – The Heartbreak of Every Day – with Nitin Agrawal

Episode 151 // October 13, 2021

#151 – The Heartbreak of Every Day – with Nitin Agrawal

The Reboot Podcast has hosted a wide variety of conversations around the complexity and diversity of the co-founder experience, such as the importance of communication, the power of mindfulness in…