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The Reboot Podcast

The Reboot Podcast

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The Reboot Podcast is a business podcast hosted by Reboot.io. It has 254 episodes, with the latest published April 2026.

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEOs, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

business ·en ·254 episodes

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1

Wisdom for Work #31 - Navigating the Neutral Zone: Embracing Change & Transition

2

#183 - The End of Suffering - with Sharon Salzberg & Jerry Colonna

3

Extras #27 - Reflection & Intention for the New Year - A Meditation Practice with Marty Janowitz

4

#182 - What AI Therapy Misses: The Power of Human Presence - with Dr. Jud Brewer & Jerry Colonna

5

#181 - Building The Company That 15-Year-Old You Needed - with Oliver Ravn & Jerry Colonna

6

#180 - Navigating Darkness, Perfectionism, and Purpose as an Entrepreneur - with Melissa Bernstein & Jerry Colonna

7

#179 - The Work of Getting Free: Redemption, Gratitude & Hope - with Shaka Senghor & Jerry Colonna

8

Wisdom for Work #30 - The Art of Influence: Building Trust & Connection at Work

9

#178 - Discovering What Matters in a Distracted World - with Soren Gordhamer & Jerry Colonna

10

Wisdom for Work #29 - Frameworks for Leading & Managing People

11

#177 - What Does It Mean To End Well? - with Randy Goodman & Jerry Colonna

12

#176 - Balancing Growth & Inner Purpose - with Christian Fenner, Mathias Tholey, Sebastian Ross, & Jerry Colonna

13

Wisdom for Work #28 - Working With Intuition

14

Wisdom for Work #27 - Parsing Emotional Data

15

Wisdom for Work #26 - Staying Grounded Throughout Your Work Day

16

Extras #26 - Moving From Fragility to Robustness - with Kelly Wendorf & Ali Schultz

17

#175 - Beyond the Self: Embracing Interconnectedness - with Luis Duarte & Jerry Colonna

18

#174 - Leading With Love & Intention - with Dr. Nicole Marie Ortiz & Jerry Colonna

19

Extras #25 - The Power of Horses for Coach Development - with Kelly Wendorf & Liz Stewart

20

Wisdom for Work #25 - The Art of Generative Listening

21

#173 - Celebrating Difference in Your Company - with Rob Castaneda & Jerry Colonna

22

Wisdom for Work #24 - Unlocking Imposter Syndrome

23

#172 - Finding Closure After Shutting Down the Business - with João Barros & Jerry Colonna

24

Wisdom for Work #23 - Cultivating Conditions of Courage

25

#171 - The Great Midlife Edit - with Chip Conley & Jerry Colonna

26

Wisdom for Work #22 - Owning Your Strengths

27

Extras #24 - Building High-Performing Teams Through Coaching - with Steph Yiu

28

Wisdom for Work #21 - Engaging Your Team to Bring Out Their Best

29

Wisdom for Work #20 - The Art of Firing Well

30

#170 - The Brave Leader's Path: Fostering Inclusivity & Courageous Decision-Making - with David McQueen & Jerry Colonna

31

Extras #23 - Unleashing Potential: Insights on Leadership, Self-Discovery, & Overcoming Fear - with Noah Kagan

32

Wisdom for Work #19 - Strategic Delegation: Building Trust & Setting Clear Expectations

33

#169 - Rupture + Repair = Resilience in Co-founder Relationships - with the Co-founders of Brood

34

The Reunion Podcast - Episode 2 - Connecting with Ancestors & Embracing the Influence of Place

35

The Reunion Podcast - Episode 1 - What If We All Belonged to Each Other? Ancestral Reunion, Belonging, and the Path to Healing

36

The Reunion Podcast - Episode 0 - Reclaiming Our Stories: A Journey of Belonging and Reunion

37

Wisdom for Work #18 - Is Coaching Right for You? - with Dan Putt & Andy Crissinger

38

#168 - The Healing Power of Tears: Building Empathy and Connection in a Numb World - with Benjamin Perry & Jerry Colonna

39

Wisdom for Work #17 - The Power of Retrospectives: Learning From the Past To Shape the Future

40

Operator's Manual #8 - The Arc of Dysfunction: From Unhealthy Chaos to Healthy Creativity - with Ali Schultz & Jerry Colonna

41

#167 - From Isolation to Openness: Engaging Fully with Real Life - with Sharon Salzberg & Jerry Colonna

42

Wisdom for Work #16 - The Brightest Bulb Challenge: Moving From Individual Contributor to Team Leader

43

#166 - We Can Choose to Ride the Roller Coaster of Entrepreneurship - with Jean Smart & Jerry Colonna

44

Operator's Manual #7 - When Should You Shut Down the Business? - with Ali Schultz & Jerry Colonna

45

Reboot Extra #22 - Scaling as a Technical Founder & CEO - with Evan Drumwright & Andy Crissinger

46

Reboot Extra #21 - Climbing Out of the Pits of Despair - with Mollie West Duffy & Liz Fosslien

47

#165 - The Bones of Belonging - with Annahid Dashtgard & Jerry Colonna

48

#164 - How To Be a Stable Board Member - with Aileen Lee & Brad Feld

49

Wisdom for Work #15 - Navigating Conflict & Difficult Conversations - with Chris VandenBrink & Andy Crissinger

50

Operator's Manual #6 - The Benefits of Bootstrapping - with Ali Schultz & Jerry Colonna

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