
The Reboot Podcast
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.
Latest episodes

Jul 16, 2024 • 56min
#173 - Celebrating Difference in Your Company - with Rob Castaneda & Jerry Colonna
Rob Castaneda, CEO of Service Rocket, discusses the power of empathy, celebrating diversity, and embracing cultural heritage in the workplace with Jerry Colonna. They explore personal migration stories, leadership philosophy, and the importance of inclusion for organizational success.

5 snips
Jun 18, 2024 • 39min
Wisdom for Work #24 - Unlocking Imposter Syndrome
Miriam Meima, a coach, and Ali Schultz dive into practical strategies for managing imposter syndrome. They discuss reframing self-perception, using breathwork for fear, and celebrating growth edges. The conversation emphasizes choice, self-awareness, and breaking free from self-doubt. Listeners gain actionable tools to reclaim a capable mindset.

Jun 4, 2024 • 57min
#172 - Finding Closure After Shutting Down the Business - with João Barros & Jerry Colonna
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 conversation with Jerry, João reflects on his entrepreneurial journey, making the gut-wrenching decision to close down his business, and how attending a Reboot Bootcamp empowered him during this difficult time. Join us as we challenge conventional success paradigms, honor diverse paths to leadership, and highlight why João embodies the essence of a servant leader. Discover why embracing change and letting go can lead to the most profound lessons. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: - How To: Leave a Review on Your iPhone: Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases.

May 14, 2024 • 27min
Wisdom for Work #23 - Cultivating Conditions of Courage
How can leaders create a safe space for honest conversations, even when those truths challenge the status quo? In this episode of Wisdom for Work, Reboot Coaches Ali Schultz and Virginia Bauman unpack the concept of "conditions of courage," exploring how fostering psychological safety within teams goes hand-in-hand with individual leaders cultivating self-awareness about the conditions that empower them to be honest. Through personal stories and insightful discussion, they unpack the power of setting boundaries and how embracing courage and authenticity in the workplace generates healthier relationships and boosts productivity. This episode is essential listening for anyone who wants to build stronger relationships, speak their truth, and navigate challenging conversations in the workplace. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: - How To: Leave a Review on Your iPhone: Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases.

18 snips
Apr 30, 2024 • 50min
#171 - The Great Midlife Edit - with Chip Conley & Jerry Colonna
Chip Conley and Jerry Colonna discuss embracing midlife as a time of growth and wisdom, highlighting the fear of aging and societal pressures. They explore the role of an elder, emotional intelligence, and leaving a positive legacy. The conversation delves into embracing uncertainty, impermanence, and transitioning through life's stages.

Apr 19, 2024 • 44min
Wisdom for Work #22 - Owning Your Strengths
Fellow coach Miriam Meima shares insights on taming the inner critic and unleashing the inner champion. Topics include recognizing strengths in the workplace, embracing personal strengths for fulfillment, and transitioning from self-criticism to self-advocacy in early career stages.

14 snips
Mar 30, 2024 • 35min
Extras #24 - Building High-Performing Teams Through Coaching - with Steph Yiu
Guest Steph Yiu discusses building high-performing teams through coaching at Automattic. They cover trust, open feedback, leadership role, empowering through tough conversations, and implementing coaching tools for personal and professional growth.

9 snips
Mar 15, 2024 • 30min
Wisdom for Work #21 - Engaging Your Team to Bring Out Their Best
Exploring team engagement and productivity, the podcast delves into the importance of clarity, communication, and understanding in a team dynamic. They discuss the significance of understanding team members' working preferences and values, setting clear expectations, and navigating team development challenges. Practical strategies to unlock a team's potential and the role of engaged teams in success and well-being are also highlighted.

Feb 27, 2024 • 35min
Wisdom for Work #20 - The Art of Firing Well
Heather Jassy, a fellow coach known for her empathetic approach to leadership, joins the discussion on the complexities of firing employees. They explore how to navigate the emotional impact of terminations while maintaining professionalism. Jassy shares her effective script, emphasizing clear communication and compassion. The conversation highlights the balance between supporting individual potential and prioritizing team effectiveness. Practical strategies for delivering difficult news with kindness and emotional awareness are also presented.

Feb 13, 2024 • 54min
#170 - The Brave Leader's Path: Fostering Inclusivity & Courageous Decision-Making - with David McQueen & Jerry Colonna
Jerry Colonna explores ethical leadership and brave decision-making with David McQueen, author of 'The Brave Leader.' They discuss the importance of inclusivity, brave conversations, acknowledging limitations, embracing vulnerability, and sense-making. They also explore the resistance against DEI programs, the distinction between morality and ethics in the pro-life and pro-choice debate, moving away from binary thinking, and creating organizations of belonging.