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.

Extras #15 – Working With Chronic Pain – with Liz Fosslien & Mollie West Duffy

Extras 15 // October 24, 2022

Extras #15 – Working With Chronic Pain – with Liz Fosslien & Mollie West Duffy

Chronic illness and chronic pain are topics that can bring up a big mix of interconnected feelings — uncertainty, burnout, anger, and even despair. They also challenge our perfectionism, make…

#161 – A Guidebook to Your Own Life – with Ian Sanders

Episode 161 // October 11, 2022

#161 – A Guidebook to Your Own Life – with Ian Sanders

In this podcast conversation, Jerry talks with Ian Sanders, author of 365 Ways to Have a Good Day, who found himself at the edge of rediscovery at the beginning of…

Extras #14 – Women’s Conversations: Your Personal Leadership Style – with Sally Helgesen

Extra 14 // September 27, 2022

Extras #14 – Women’s Conversations: Your Personal Leadership Style – with Sally Helgesen

Sally Helgesen is a women’s leadership expert who has written many books over the past few decades on women and leadership (How Women Rise, The Female Advantage, The Web of…

#160 – Learning From Regret – with Daniel Pink

Episode 160 // August 13, 2022

#160 – Learning From Regret – with Daniel Pink

What can we learn from regret? Regret gives us chance to see things from both sides. The experience we lived through, and the retrospective. Pausing to reflect on what was…

#159 – The Power of Shared Leadership – with Andrew Alexseyenko

Episode 159 // July 12, 2022

#159 – The Power of Shared Leadership – with Andrew Alexseyenko

When faced with uncertain times and unavoidable challenges, how we show up matters. For some of us, a healthy reaction might be to withdraw and tend to the tender parts…

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…

#158 – Show Up for Your Life – with Laurie Segall

Episode 158 // June 7, 2022

#158 – Show Up for Your Life – with Laurie Segall

Laurie Segall is an award-winning journalist, author, and the founder of Dot Dot Dot and D3 Network. In this episode, Laurie sits down with Jerry to chat about her tenure…

Wisdom for Work #11 – Career Transitions at Midlife – with Jim Marsden, Ray Foote, Marty Janowitz & Jerry Colonna

Wisdom for Work 11 // June 22, 2022

Wisdom for Work #11 – Career Transitions at Midlife – with Jim Marsden, Ray Foote, Marty Janowitz & Jerry Colonna

In this conversation, Coaches Jim Marsden, Marty Janowitz, Ray Foote, and Jerry Colonna sit down to explore career transitions at midlife. Together, they describe their unique midlife experiences and share…

#157 – When Are You Done? – with Chris Remus

Episode 157 // May 10, 2022

#157 – When Are You Done? – with Chris Remus

In this podcast, Jerry sits down with Chris Remus, Founder of Chainflow, to explore an enormously complex and personal question, “What does it mean to be done?” What unfolds is…

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