The Reboot Podcast

How often do you connect with those who came before you? What do you know about them? What was life like for them? What did they live through? What were their unfulfilled dreams? What stories are still alive in your family to this day? When doing the work of learning about our past, we can forget that we are here because of many generations of love expressing itself. In this podcast Extra, Jamie Kim offers a visualization to connect with those who came before you and to feel the magnitude of that love and support. 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.

In this episode of our Operator's Manual series, Ali and Jerry consider how the health and resilience of an organization can be directly tied to the CEO’s own modeled behavior around self-care. Jerry reminds us that the CEO’s job is to build the machine that builds the products and services, not to build the products and services. 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.

Matt Blumberg, founder and CEO of Bolster, shares his insights on entrepreneurship after years of leading Return Path. He discusses the transition to launching Bolster in his 50s, emphasizing the need for a seasoned team. The conversation touches on his book, Startup CXO, which outlines essential skills for functional roles. They also explore the advantages of using fractional executives to scale efficiently and highlight the importance of empathy and proactive planning in leadership, especially for founders navigating diverse roles.

The phrase, “The Great Resignation,” has become abundantly popular in the media over the recent months. In this episode, Ali and Jerry discuss how pandemic life has ushered forth larger questions around how we want to work and live. They consider how this unique period in time has brought about a rare opportunity for companies, leaders, and employees to re-examine their values, and to put people back at the heart of our organizations. 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.

The more we work with clients, the more we see leaders longing for pieces of wisdom around the parts of the job that aren't necessarily in any playbook. In this conversation, Ali Schultz sits down with Jerry to explore the question: What does it mean to step back and let other people step up and lead? 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.

We wanted to bring you a new-ish kind of conversation to our podcast channel - but not new to the halls of Reboot. This one is for the operators, where we talk about the practical-tactical challenges that come from scaling an organization and growing in your leadership. In these conversations, Ali Schultz sits down with Jerry Colonna and gets him to wax-practical the common topics we see leaders face. In this episode of our Operators Manual series, Ali and Jerry discuss: What is the job of the CEO? 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.

After a decade of working in nonprofits, Philip Deng has decided to build something of his own. In this conversation, Philip sits down with Jerry to chat about his company Grantable, which helps individuals and organizations make grant writing more efficient. Philip, who identifies as Asian American, opens up about the loneliness he’s faced as a leader and CEO. He reflects on how the events of his childhood, specifically his parents divorce, left him with complicated feelings about his self-worth and ability to belong. Jerry supports Philip in coming to understand the ways in which he unconsciously gets in his own way and explains how the subroutines he developed during childhood (the ghosts in his machine), can simultaneously hold him back and be his greatest superpower. 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.

The Reboot Podcast has hosted a wide variety of conversations around the complexity and diversity of the co-founder experience, such as the importance of communication, the power of mindfulness in partnerships, and shared our advice for navigating co-founder conflict. Co-founders looking to meet the day-to-day challenges of running a business must commit to consistent work in aligning their vision and purpose for the organization, but what happens when an unforeseen tragedy throws all your preparation out the door? In this episode, Nitin Agrawal, Co-founder and CEO of Interstride, describes the loneliness and pathlessness he experienced in the wake of the sudden death of his dear friend and fellow co-founder, Christian. Nitin details the experience and soul searching it took to rediscover his purpose and recounts how his journey through grief restored confidence in his own ability to lead. Jerry and Nitin explore what it means to manage the heartbreak of the every day and share advice for finding the strength to land on your feet when your foundation gets shaken to its core. 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.

In this 150th episode, we are privileged to share Jerry’s conversation with Ashanti Branch, Founder and Executive Director of The Ever Forward Club, whose mission is to transform the lives of underserved youth by providing safe opportunities for academic, personal, family, and community development. Ashanti reflects on his experiences as a young black man, the pressure he felt to conceal his true emotions from his peers, the ways in which men are conditioned to neglect their feelings, and why his own memories compelled him to create a protected space for the young men of his classroom. Jerry and Ashanti discuss the importance for men to find trusted circles in which they share their true feelings, and why removing the masks we wear allows us to become better partners, leaders, and community members. 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.

In order to become the leaders we were born to be, we must first be willing to radically inquire within. By cultivating a deep growth mindset, we’re able to mature and develop not only as leaders but as humans. Getting curious about our blind spots in leadership and seeing clearly our strengths and weaknesses as well as understanding how we are perceived is the basis for any leadership development plan. We cannot grow if we don’t understand the work we have to do. In this episode, Andy Crissinger sits down with Courtney Joyce, coach and 360° Program Director, to talk about Reboot’s approach to 360 reviews and why they are so incredibly powerful for leaders who are looking to take their development to the next level. The pair connect with Nick Francis, CEO of Help Scout, to chat about his 360s experiences, and the impact they’ve had on his personal and professional growth. 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.