The Reboot Podcast

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

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

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 o

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 and encouraging those women to run for elected office, and a proud Kentuckian to boot. Amy sits down with Jerry to chat about her time in the military, how it shaped her views on service and honor, and why she felt compelled to run for the US Senate in the 2020 election. Amy discusses her new book, "Honor Bound: An American Story of Dreams and Service" and shares the valuable leadership lessons she’s learned over the course of her career; the pair address the threat of complacency and share why democracy, like a garden, requires constant tending. 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.

On this episode of the Reboot Podcast, Jerry hosts a conversation with David Hieatt, co-founder of Hiut Denim Company. In this exchange, David recounts how the sale of his first company left him feeling listless and ungrounded. He shares how he regained his sense of purpose after founding Hiut, a company that revived the denim industry in the small town of Cardigan, Wales. David describes the difficult process of temporarily closing the factory due to COVID-19 and how these past few months have given him the space to reaffirm the company’s values and solidified the importance of taking care of not only the people of his organization but the community as a whole. Jerry and David acknowledge the value of servant leadership, remark on the beauty of team building, and consider what happens when your company grows you. 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 news

In moments of conflict, it can be difficult to stay present amongst our discomfort. However, when we lean into love and compassion we might begin to see conflict in a generative light. In this episode of the Reboot Podcast, Jerry is joined by Regina Smith, MA and Amanda Aguilera, PsyD, experts in the field of power dynamics, conflict, and equity. In this conversation, Regina and Amanda examine and characterize the intersectionality of power dynamics and expound on the various ways power is conferred in our culture (and our workplaces). They highlight how conflict avoidance is often most detrimental to those in the down power role and why expanding our capacity to be in conflict is necessary for progress. The conversation explores how cultivating a positive outlook towards conflict supports our ability to engage empathetically and skillfully when moments of friction arise. By introducing the notion of generative conflict (and the idea of radical collaboration), they underscore why love, community, and connecti

When it comes to confidence, feeling A-Ok with showing vulnerability, and trying to avoid the sneaky snares of Imposter Syndrome, we often feel at odds, torn between the parts of us that say, “Who do you think you are?” and the parts of us who know who we are. Self-doubt and inadequacy can creep in and color the most assured parts of us at times. But, what’s really at play here? We know it’s an inside job to keep ourselves clear-headed and attuned with our inner knowing, regardless of what the world throws our way in terms of perceptions, biases, and double standards. How do we, as women, stay in our own bodies, hold fast to our own truths, and not view ourselves through the eyes and expectations of others in the world-at-large? Who do you choose to be? What life do you want to lead? In this third episode of our Women Conversation series, Reboot Co-founder Ali Schultz joins fellow coaches Ann Mehl, Heather Jassy, and Miriam Meima for an exploration of how imposter syndrome grips women, the masks they feel t

What are the factors that contribute to the failure of almost 90% of startup ventures? In this episode, Jerry sits down with author and Harvard Business School professor Tom Eisenmann to discuss the patterns that often precipitate the vast majority of startup failures. The pair take a closer look at how the advice to “fail fast” often leads founders to false start — risking capital and time on the wrong solutions. They shine a light on the pressure founders feel to grow the business rapidly, the lionization of venture capital, and the true human cost of failure. 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.

Suneel Gupta is an entrepreneur, Harvard professor, and author of “Backable: The Surprising Truth Behind What Makes People Take a Chance on You.” In this episode, Suneel chats with Jerry about his personal struggles with fundraising and how it led him to attend a Reboot Bootcamp. They host a larger conversation around identity, the way our fears keep us small and safe, and why living and leading from our fullest selves requires confronting the monster in our head. 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 our coaching practice, one of the most common questions we receive from investors is, “How do I build more trusting and impactful relationships with leaders in my portfolio?” As coaches, we believe the core challenge that limits the ability for founders and investors to connect in a more collaborative way is rooted in the dynamics of power. In this short clip, Dan Putt, Reboot Co-founder and Director of Client Engagement and Reboot’s Director of Coaching, Andy Crissinger define the three dimensions of power and share their advice for navigating power differences to build better founder-investor relationships. 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.

This being human is a profoundly awesome adventure; our lives are peppered with moments of happiness, joy, and wonder, but our experiences can be messy, exhausting, and heavy too. As leaders, how do we manage the cacophony of emotions that we inevitably carry with us to the workplace? What holds us back from opening up, sharing, and being true with our colleagues, especially when we’re struggling? Ryan Caldbeck is the Founder and Executive Chairman of CircleUp. In this episode, Ryan opens up about the inherent loneliness that comes with being a CEO and reveals how a particularly challenging period in his life exacerbated those feelings of isolation. He describes how an interaction with his young daughter drove his decision to step back from his role as CEO, the relief that sharing his experience with his colleagues brought, and the grief that comes hand in hand with closing this chapter of his life. Jerry encourages Ryan to see that in his sadness lives an opportunity to turn towards curiosity and inquire dee

As frequent listeners of the podcast can attest, a well-formed open, honest question can be a catalyst for radical self-inquiry and deep inner work. For Gino Zahnd, the founder of Cozy and Seabright, that question was, “What would I like the people that I work with to know about me that they don’t know?.” Gino, who lives with a rare genetic order called Fabry Disease, shares how one profound question asked at Reboot Bootcamp gave him the courage to share his health struggles with his team and ultimately led to a life-changing kidney donation from a colleague. Jerry chats with Gino about how things have changed since his Bootcamp experience in 2016, his decision to step down as CEO of Cozy, and his new life in Colorado. 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.

At Reboot, we believe making and keeping commitments is a necessary building block for sustained collaboration and growth within an organization. In our coaching we’ve seen first hand the damaging impact the breakdown of commitments can have on trust, performance, and workplace culture. In this clip, Andy Crissinger and Jeff Riddle share why coordinated action, the process of requesting and making commitments, requires good hygiene around elements of communication, especially as organizations adapt to working in virtual environments. 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.

Jeremy Bloom is a 3x World Champion, 2x Olympic Skier and former football player for the Philadelphia Eagles and the Pittsburgh Steelers. He is the founder of Wish of a Lifetime and CEO of Integrate, a venture backed marketing software company. In this conversation, Jeremy shines a light on the burdens elite athletes face and describes the toll it has on mental and emotional well being. Jerry and Jeremy discuss the striking parallels between the pressures elite athletes encounter and the everyday stressors entrepreneurs endure. The duo contemplate the inertia that arises from failure and consider the perils of allowing our self worth to be defined by the attainment of our goals. Jeremy shares why the hardest aspect of leadership is managing your own psychology and why honing the ability to differentiate signal from noise is paramount for today’s leaders. 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: Ne

At Reboot, we believe feedback can be one of the best ways to maintain relationships and strengthen connections within an organization. In this clip, Coaches Andy Crissinger and Jen Cody share why creating an underlying culture that supports the health and safety of an organization through feedback is such a valuable leadership tool. 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 spending the last seven years routinely moving from country to country in Latin America, Nathan Lustig’s nomadic life was upended when the Coronavirus pandemic began to grip the entire world. As the Managing Partner of Magma Partners, Nathan became accustomed to a transient lifestyle as he worked to build his early-stage venture capital firm. Now facing the first prolonged travel hiatus of his recent career, Nathan sits down with Jerry to unpack the ways in which his aversion to setting roots has served him personally and professionally. Jerry reminds Nathan that in this moment lives an opportunity to reflect clearly on the lessons he’s learned in lockdown, and to inquire deeply about who he wants to be moving forward, and most importantly, what his work is to do in the world. 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

In this fourth episode of our Women Conversation series, Reboot Coach and creator of The Third Jamie Kim sits down with Bunny and Taran Ghatrora, co-founders of Blume, a venture-backed self-care company. Taran and Bunny open up about their experience navigating the unforeseen challenges brought about by COVID and describe how their own self-care needs have shifted in the last year. The trio hosts a discussion around the unique hurdles many BIPOC female founders face when obtaining VC funding, and seek to define what it means to lead from a place of feminine leadership. 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 fresh release, Jerry sits down with past client, former CEO of Etsy, and fellow executive coach, Chad Dickerson. In this episode, Chad describes the shift from CTO to CEO and the anxiety he experienced in the months after his transition. He gives insight into some of the unique challenges he faced in his six years as CEO of Etsy, and opens up about his painful departure from the company. Jerry and Chad contemplate what it means to lead with compassion, humanity, and integrity, and consider how moments of heartbreak deliver greater resiliency and cultivate equanimity. 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.

Sydnie L. Mosley is an artist-activist, educator, and Artistic Director of SLM Dances, a New York City-based collective of women and nonbinary people who tackle issues of race and gender through experimental dance. In this conversation, Sydnie shares how expression through dance necessitates deep presence and connection to our bodies and highlights the ways in which its practice supports self-actualization and living into the fullness of our humanity. Jerry and Sydnie contemplate the real consequences and untold harm disembodiment has had on our organizations and in our communities, and why coming home to ourselves allows for connection, empathy, compassion to ripple out through the circles we inhabit. 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.

When the disquiet and unease of turbulent times weigh heavy on our hearts, can opening ourselves up to joy provide respite from the loads we carry? Ingrid Fetell Lee, designer and author of ​Joyful: The Surprising Power of Ordinary Things to Create Extraordinary Happiness, joins Jerry for an exploration of how the experience of joy can serve as a balm in times of crisis. In this episode, Jerry and Ingrid define joy (and how it can be differentiated from happiness) and consider the role it plays in our lives. Ingrid describes how humans are hardwired to find joy and underscores the extraordinary ways in which it serves to combat stress and fortify resiliency in times of adversity. Ingrid reminds us that times of stillness can broaden our capacity for finding delight in ordinary moments, and how those small joys can sustain us in arduous times. 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