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.

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#146 - The Cost of Failure - with Tom Eisenmann & Jerry Colonna

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.

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#151 - The Heartbreak of Every Day - with Nitin Agrawal & Jerry Colonna

What does it feel like to connect deeply with the groundlessness that arises during times of anxiety? In this short clip, Reboot Coach and Facilitator Marty Janowitz leads a short meditation practice in compassionate abiding. 

In this introductory practice, you’ll focus on breathwork, sitting with uncertainty, and discovering what it means to reconnect with the cradle of our lovingkindness.

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Reboot Extra #12: Compassionate Abiding: A Guided Meditation for Anxious Times with Marty Janowitz

What are the benefits of adopting a coaching mindset in your leadership and life? 

In this podcast Extra, Reboot Coaches Andy Crissinger and Chris VandenBrink break down the three fundamental components of coaching - listening, inquiry, and mirroring. The duo describes how incorporating a coach's mentality in your leadership toolkit can foster growth, learning, and creativity within your organization, and provide examples of when and where the leader as coach skillset should be utilized and in which instances it should be avoided.

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Wisdom for Work #10: Leader As Coach - with Andy Crissinger & Chris VandenBrink

Science tells us that the best time to meditate is often when it’s not easy. Bringing mindfulness and perhaps even a pocket meditation for recentering to the situations when you are getting off-kilter, ungrounded, and upregulated are the moments that create more lasting change.

In this short clip, Reboot Coach and Facilitator Chrystal Bell leads a short meditation practice designed to support you in finding your center and returning to stillness amidst turbulent times. May it be a grounding practice for when you encounter the stormy weather of life.


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Reboot Extra #16 - Mountain Meditation: Finding Your Center

We often say trust is one person's assessment of another person's competence, sincerity, and reliability. Accountability is a related concept to trust, but it’s also an inside job. Being accountable means being ready to show up for the work that’s in front of us and be a contributor to the fulfillment of the goal of the whole.

In this Wisdom for Work, Coaches Ali Schultz and Virginia Bauman illustrate why the key to accountability is healthy channels of communication and cultures of trust. They make important distinctions between leader-led and self-led accountability and share why one method is often more impactful than the other. They discuss how leaders can model accountability to the rest of their team, and reveal why the highest-performing groups are often the ones that develop a mutual self-accountability muscle.

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Wisdom for Work #13: Accountability & Trust - with Virginia Bauman & Ali Schultz

In this Wisdom for Work, Andy Crissinger and Chrystal Bell consider the importance of cultivating lasting practices that link to your values and how these ordinary rituals can support you.

Chrystal describes the three key elements of practice: intention, attention, and repetition. The duo shares some simple micro-practices for grounding, centering, and setting intentions, and describes how adopting any of these practices can support you in becoming your best adult self.

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Wisdom for Work #14: Micro-Practices for Leaders: Finding Ground & Setting Intention

If you work with people, odds are good that hard conversations will be part of your work life. Whether it’s firing an employee or dealing with tension in the executive team or trying to get along with a challenging personality at the office, managing people at any level, and in any scenario, makes difficult conversations inevitable and also essential to working well together. 

In this podcast, Chris VandenBrink and Andy Crissinger talk about leaning into hard conversations so you can do so with skill and clarity.

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Wisdom for Work #15 - Navigating Conflict & Difficult Conversations

A common question we get asked at Reboot is: How do I know if coaching is right for me? 

In this episode, Reboot Coaches Dan Putt and Andy Crissinger delve into the world of coaching and its transformative impact on personal and professional growth. They shed light on what coaching entails, debunking common misconceptions and highlighting the importance of introspection and self-inquiry. Whether you are considering coaching for yourself or simply curious about the coaching process, this episode is sure to provide valuable insights.

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

Delegation is one of the most essential skills to master as a leader. Done well, it’s the fundamental behavior that impacts the culture, execution, and the bottom line. It creates inclusive leaders, flexible businesses, and the fostering of leaders in each seat in the organization.

In this episode, Reboot Coaches Ali Schultz and Virginia Bauman dive into the world of delegation, highlighting the importance of clarity, trust, and accountability in the process. Virginia shares a valuable mental model for delegation, emphasizing the factors of individual readiness and task importance. The pair explore the challenges faced by leaders in delegating tasks and provide valuable insights for both leaders and team members.

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

As a leader, how do you decide which inputs to listen to? What strategies do you use for personal growth and reflection? How do you create a work environment that supports and uplifts your team?

In this episode, Reboot Co-founder Dan Putt engages in a candid conversation with Noah Kagan, the CEO of AppSumo and author of the forthcoming book Million Dollar Weekend. Noah opens up about his path of personal and professional growth, sharing practical tools and hard-won wisdom for overcoming insecurities, finding your authentic leadership style, and creating a work environment where the collective thrives. The pair discuss the benefits of seeking honest feedback, empowering underdogs in business, and, most importantly, learning to like (and trust) yourself.

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Extras #23 - Unleashing Potential: Insights on Leadership - with Noah Kagan

What does it mean to lead bravely? In this powerful episode, Jerry Colonna explores the essential elements of ethical leadership with David McQueen, author of “The Brave Leader.”

David sheds light on the difference between ethical and moral decision-making, emphasizing the courage and resilience needed to navigate the gray areas while staying true to core values. He emphasizes the importance of not just fostering diversity, but building true inclusion, where every voice is heard, valued, and empowered to contribute. Together, they discuss the need for brave conversations, acknowledging limitations, and embracing vulnerability as essential tools for building trust and fostering genuine connection.

This episode is a call to action for leaders at all levels to step up, embrace courage, and become the changemakers their organizations need.

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#170 - The Brave Leader's Path: Fostering Inclusivity & Courageous Decision-Making

If you're a leader, few things can ruin your day more than needing to fire someone. It's just plain hard to do, even when you know it's the right decision.

In this insightful discussion, Ali and fellow coach Heather Jassy share advice for effectively and compassionately handling the challenging task of letting someone go from their job. Heather shares her script for handling the firing process with clarity and empathy, acknowledging the discomfort and awkwardness of such conversations while striving to maintain kindness and professionalism.

This podcast is full of valuable insights and practical strategies for leaders to consider when navigating difficult conversations around performance issues and termination.

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Wisdom for Work #20 - The Art of Firing Well

How do you engage your team to bring out their best? 

In this Wisdom for Work, Reboot Coaches Andy Crissinger, Jen Cody, Jim Marsden, and Chris VandenBrink gather to explore the critical importance of clarity, communication, and understanding within a team dynamic. The group highlights the significance of understanding team members' working preferences, motivations, and values to build relationships, set expectations, and create clarity within the team.

Join the conversation as they explore practical strategies to unlock your team's potential and discover why an engaged team is not just desirable but essential for success and overall well-being.

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

In this Podcast Extra, Andy Crissinger delves into the world of coaching and its transformative impact on corporate culture with guest Steph Yiu, Chief Customer Officer at WordPress VIP and leader at Automattic. 

They explore the extensive Reboot program at Automattic, which focuses on trust, open feedback, and building a supportive environment for personal and professional growth. Steph shares her journey of incorporating coaching tools into her leadership role, and they discuss how these tools have empowered her to lead through complex organizational reorganizations and facilitate tough conversations. 

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

We all have that nagging voice in our head, the inner critic, that loves to point out our flaws. But what if there was a way to silence that bully and amplify a different voice, your inner advocate? In this episode, Ali chats with fellow coach Miriam Meima about taming the inner critic and unleashing your inner champion.

This episode is for anyone who has felt like they're not good enough, replays past conversations in their head, or struggles to see their unique strengths.  

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Wisdom for Work #22 - Owning Your Strengths

In this episode of The Reboot Podcast, Jerry Colonna sits down with the insightful Chip Conley, author of "Learning to Love Midlife." Together, they explore the transformational journey of embracing midlife as a time of growth and wisdom. Chip shares his personal tale of crisis and renewal, emphasizing the fear and cultural pressures surrounding aging.

They ponder the role of an elder and the importance of embracing uncertainty, impermanence, and transition in life. The conversation touches on the significance of emotional intelligence, the three stages of transition, and leaving a positive legacy for future generations.

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

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.

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Wisdom for Work #23 - Cultivating Conditions of Courage

Full notes and more: reboot.io/podcast 
Who are you? What do you believe to be true?  What do you bring consciously to the world? And, even more interesting, what do you bring unconsciously to your work, your organization, your relationships? How does that which you have either denied about yourself, or feel uncomfortable about, shape your life, either positively or negatively?   What lies in this unseen shadow?  And why is it important for you to explore? 

The work of today’s guest shows up in just about everything we do here at Reboot so we are thrilled to have one of our key teachers, Parker Palmer, join Jerry for a discussion on a very important and powerful topic: Shadow and Leadership.  


#14 Shadow and Leadership - with Parker Palmer

For full video visit: https://www.reboot.io/podcast
JW Player has come a  long way. The JW player and platform is now used by over 2.5 million publishers and 20% of the fortune 1,000 companies. Each month about 1 billion people watch video on their platform.  Behind those numbers are real people--including three co-founders who, over the last eight years, have experienced their own profound personal growth and leadership transformations.  

In a special first video episode, only fitting for the co-founders of one of the world’s largest video platforms, we have the 3 co-founders of JW Player (Dave Otten, Jeroen "JW" Wijering, and Brian Rifkin) joining Jerry in person.  In a very open conversation, they explore key challenging moments in their company and partnership history -and how they emerged from those moments stronger and more committed than ever. It's an inspiring story of leaders born through adversity

#15 Becoming a Leader: The Crucible of Co-Founder Conflict

Do you love yourself enough to listen with the ears of your heart to the other voices of yourself speaking? 
- Beno Kennedy

In today’s special episode Jerry Colonna, Jim Marsden, and Jade Sherer talk about the power and opportunity of time on the land, Jerry’s own experience on a quest, which was guided by Jim and Jade, and why a quest could change your awareness forever.  If it terrifies you, you are ready...go apply at reboot.io/quest.


Links

Apply for the Reboot Quest
- http://www.reboot.io/quest

Jim Marsden on Twitter 
- https://twitter.com/jamarsden  

Jade Sherer 
- http://www.earthsecho.com/htm/about.htm 

Earth’s Echo Explorations 
- http://www.earthsecho.com/index.htm 

Animas Valley Soulcraft Program 
- http://www.animas.org/ 

Bill Plotkin 
- http://www.animas.org/about-us/our-founder/ 

"Soulcraft" by Bill Plotkin 
- http://www.amazon.com/Soulcraft-Crossing-Mysteries-Nature-Psyche/dp/1577314220 

#36 The Quest - with Jim Marsden, Jade Sherer, & Jerry Colonna

Parker Palmer is a man whose teachings mean so much to us and our work at Reboot, so it's wonderful to welcome him back to the podcast for a new conversation with Jerry.  

Jerry invited Parker back to explore some important questions:

- What is the role of community in responding to a toxic environment?

- How do I respond when my leader hasn't done their work and is leading from that place of shadow?

- What does it mean when a leader is using organization to resolve unconscious issues?

As is always the case when Parker and Jerry get together, this is a conversation packed full of deep lessons on leadership, the shadow, the importance of relational trust, and the incredible power present in community. This episode will leave you with new profound questions and answers about yourself, your role in your organization, and the power you hold, but may not yet accept.

Links

Parker Palmer 
- http://www.couragerenewal.org/parker/ 

"To Bless the Space Between Us" by John O’Donohue 
- http://www.amazon.com/Bless-Space-Between-Us-Blessings/dp/0385522274 

Nelson Mandela 
- https://en.wikipedia.org/wiki/Nelson_Mandela 

Rosa Parks 
- https://en.wikipedia.org/wiki/Rosa_Parks 

"A Ritual to Read to Each Other" by William Stafford 
- http://williamstafford.org/spoems/pages/ritual.html

#42 Building Relational Trust - with Parker Palmer & Jerry Colonna

“I am not what has happened to me, I am what I choose to become.” 
- Carl Jung

Amir Salihefendic, the founder and CEO of Doist, is the creator of the powerful and popular productivity tool, Todoist (which is awesome). He comes to Jerry feeling torn between two seemingly different directions for his business.  On one side, he feels the ambition to do big, world changing things and to be on every smartphone and desktop.  But on the other side, as the son of entrepreneurial parents who owned a grocery store, he knows how important it is to just keep the business alive and take care of yourself and your family (and to be grateful for that) - to not put your family, your health, yourself at risk. The ambitious path with burnout or the steady, safe path with possible regrets? He has wrestled with this as something he must decide, but what if there isn't a choice? Or what if there is a 3rd option he’s not seeing? 

Jerry and Amir explore this apparent conflict, talk about his upbringing and his family’s escape from the war in Bosnia when he was young, and in this exploration they uncover a new path forward for Amir and the business, one of integration.

Links

Amir Salihefendic on Twitter 
- https://twitter.com/amix3k
 
Doist 
- https://doist.com/ 

Todoist 
- https://todoist.com/ 

Todoist on Twitter 
- https://twitter.com/Todoist 

Reboot.io Podcast # 7 Depression and Entrepreneurship – With Jerry Colonna and Rand Fishkin
- https://www.reboot.io/episode/depression-and-entrepreneurship/

Parker Palmer 
- http://www.couragerenewal.org/parker/

#47 Embracing Both Sides of Yourself - with Amir Salihefendic & Jerry Colonna

“One does not become enlightened by imagining figures of light, but by making the darkness conscious. The latter procedure, however, is disagreeable and therefore not popular.” 

- C.G. Jung

Exploring one’s shadow is no easy undertaking. The idea of getting to know what Jung referred to as, “That which I do not wish to be” is rarely considered an exciting prospect.  Yet we implore all leaders to be courageous and get to know and learn to work with their shadow. It is only when we do the work to make the unconscious conscious, that we are able to build true compassion for ourselves and others; freeing us to become the leaders we were born to become.

James Hollis is a Jungian analyst, author and lecturer whose work has inspired and influenced us at Reboot. In this episode Jerry and James talk in depth about the Jungian concept of shadow, how shadow shows up in leadership, and what we can do once we become aware of our shadow.

Links

James Hollis’s website 
- http://www.jameshollis.net

"Why Good People Do Bad Things"
- goo.gl/cS6kWe

Episode #14 Shadow and Leadership 
- https://www.reboot.io/episode/shadow-and-leadership/ 

Episode #28 Reclaiming Shadow 
- https://www.reboot.io/episode/28-reclaiming-the-shadow/ 

Episode #42 Building Relational Trust 
- https://www.reboot.io/episode/42-building-relational-trust-parker-palmer

#51 The Love that Heals: Welcoming in Our Shadow - with Jerry Colonna & James Hollis

“Love isn’t merely some second-hand emotion; love is the fuel that powers great organizations.” - Jerry Colonna

In this episode of the Reboot Podcast, Jerry sits down with Steve Farber, author of Love Is Just Damn Good Business, for a conversation on leadership and the value of love in the workplace. As Steve reflects on the transformational power of love, Jerry unpacks the ways in which it cultivates trust, reaffirms feelings of safety and builds spaces of belonging. Together they consider the business case for love, reflecting on its ability to sustain healthy teams, drive personal growth, and foster self-actualization, ultimately lending a hand in providing spaces for humans to come together and do their best work. To close out their discussion, Steve highlights how companies built around cultures of love typically benefit from increased customer loyalty, boosts in profitability, and capture higher percentages of market share.

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#118 - The Business Case for Love - with Steve Farber & Jerry Colonna

The ability to differentiate between transition and change is important for leaders to understand when attempting to lead groups of people through uncertain times. In this short clip, Andy Crissinger, Reboot’s Director of Coaching, introduces a helpful framework for leading teams through times of transition.

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Wisdom for Work #3: Leading Through Transitions - with Andy Crissinger

In this release, Jerry sits down with leading diversity and inclusion expert Jennifer Brown to explore her latest book, ​"How to Be an Inclusive Leader: Your Role in Creating Cultures of Belonging Where Everyone Can Thrive."​ In this conversation, recorded at the beginning of 2020, Jennifer reveals why inclusive leadership is not only risky, but often uncomfortable, and why discomfort is necessary for individual and organizational growth. Jerry and Jennifer analyze why true inclusivity requires removing the barriers to belonging in the workplace and share that when those with whom we work feel a true sense of belonging, trust and productivity increase within an organization. They examine the power of pronouns, make the distinction between allyship and advocacy, confront the ways in which our biases direct us, and describe why leadership without inclusivity is not true leadership.

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#127 - Leadership Without Inclusivity Is Not Leadership - with Jennifer Brown & Jerry Colonna

Inquiry is an incredibly central and important skill, but it’s often underemphasized or even overlooked in the world of leadership. In this clip, coaches Andy Crissinger and Chris Vandenbrink share why adding inquiry as an additional tool in your toolkit can be in service of you, your team, and the work that you’re trying to do together.

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Wisdom for Work #5: Inquiry as a Leadership Skill - with Andy Crissinger & Chris VandenBrink

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.

Popular tracks by The Reboot Podcast