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: Greater Resiliency

#172 – Finding Closure After Shutting Down the Business – with João Barros

#172 // June 4, 2024

#172 – Finding Closure After Shutting Down the Business – with João Barros

There’s more to leadership than building the next billion-dollar unicorn. Our guest, João Barros, has walked a fascinating path – from professor to CEO and back again. In this candid…

#171 – The Great Midlife Edit – with Chip Conley

#171 // April 30, 2024

#171 – The Great Midlife Edit – with Chip Conley

In this episode of The Reboot Podcast, Jerry Colonna sits down with the insightful Chip Conley, author of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age.…

#168 – ​​The Healing Power of Tears: Building Empathy and Connection in a Numb World – with Benjamin Perry

Episode 168 // Oct 17, 2023

#168 – ​​The Healing Power of Tears: Building Empathy and Connection in a Numb World – with Benjamin Perry

What is your relationship to crying? When was the last time you allowed yourself to weep openly? In this compelling episode of the Reboot Podcast, Jerry sits down with Benjamin…

#167 – From Isolation to Openness: Engaging Fully with Real Life – with Sharon Salzberg

Episode 167 // August 25, 2023

#167 – From Isolation to Openness: Engaging Fully with Real Life – with Sharon Salzberg

When confronted with the realness of our lives, how we choose to respond matters. It’s no easy feat to turn toward suffering when the world around us gets messy. However,…

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 #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…

Podcast Topic: Greater Resiliency