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: Believing in Yourself

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…

#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…

#149 – Tending the Garden of Democracy – with Amy McGrath

Episode 149 // August 11, 2021

#149 – Tending the Garden of Democracy – with Amy McGrath

Amy McGrath is a retired US Marine Corps Lieutenant Colonel, the founder of Honor Bound – a 501(c)(4) nonpartisan organization committed to leadership development for women with a service background…

#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…

#91 – Do I Even Have a Superpower? – with Kent Cavender-Bares (re-release)

Episode 91 // September 20, 2018

#91 – Do I Even Have a Superpower? – with Kent Cavender-Bares (re-release)

Have you ever asked yourself the question: I wonder if we’d be better off with someone else in my role? In this podcast, a listener, Kent Cavender-Bares from Rowbot comes…

#63 – Remember Who You Are – with Adi Mashiach

Episode 63 // June 22,2017

#63 – Remember Who You Are – with Adi Mashiach

Throughout his life, Adi Mashiach has been a brilliant student, a successful doctor, and has experienced two successful company exits. Along with his wife Mirella, Adi has stepped into the…

#58 – The Joy of Surrender – with Simon Cant

Episode 58 // April 6, 2017

#58 – The Joy of Surrender – with Simon Cant

Simon Cant’s path to becoming a VC has been a windy road. Building on a career that includes stints as a lawyer, founder, consultant, director of a non-profit and advisor.…

#50 – A True Place of Belonging

Episode 50 // November 7, 2016

#50 – A True Place of Belonging

Virginia Bauman and Iris Bainum-Houle have experienced great success- Virginia as an entrepreneur and founder,  Iris as a designer for film and entertainment- and both have also experienced great feelings…

#48 – When are you really an Entrepreneur?  – with Sarah Weiler

Episode 48 // September 22, 2016

#48 – When are you really an Entrepreneur? – with Sarah Weiler

What makes an entrepreneur an entrepreneur? Sarah Weiler followed her passion to bring creativity and playfulness into the workplace by founding The Power of Uke eight months ago. The business is growing, but Sarah remains reluctant to identify as an entrepreneur. In this conversation she and Jerry talk about what is holding her back from doing so, and how she can take her seat as an entrepreneur.

Podcast Topic: Believing in Yourself