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...
Jun 15, 2021•43 min
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 Podc...
Jun 01, 2021•44 min•Ep. 145
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 dime...
May 18, 2021•21 min
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 abo...
May 05, 2021•50 min•Ep. 144
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 ul...
Apr 20, 2021•48 min•Ep. 143
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 ad...
Mar 30, 2021•21 min
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 everyda...
Mar 16, 2021•43 min•Ep. 142
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: www.reboot.io/leave-itunes-review-via-computer/ - Ho...
Mar 02, 2021•14 min
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 ro...
Feb 16, 2021•46 min•Ep. 141
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, an...
Feb 04, 2021•1 hr 1 min
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 consid...
Jan 25, 2021•1 hr 7 min•Ep. 140
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 conseq...
Jan 09, 2021•57 min•Ep. 139
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 ...
Dec 17, 2020•45 min•Ep. 138
"Not everything that is faced can be changed. But nothing can be changed until it is faced." - James Baldwin In this release, Jerry sits down with Forest Richter, Co-founder and CEO of Uncrowd.io, a software platform that serves to connect underrepresented startup founders with investors. Forest shares how his ongoing battle with imposter syndrome has undermined his self-confidence and has called forward deeper questions around whether he, as a cis-gendered white man, can effectively execute the...
Dec 04, 2020•55 min•Ep. 137
Joining Jerry on this episode of the Reboot Podcast is Marcus Aurelius Anderson, author of "The Gift of Adversity: Overcoming Paralysis and Pain to Find Purpose". While preparing to deploy with the US Army, Marcus suffered a severe spinal cord injury which left him paralyzed from the neck down. In this conversation, Marcus shares how turning to gratitude provided the antidote to the denial and anger he felt in the aftermath of his accident, describing how his paralysis forced him to literally st...
Nov 12, 2020•44 min•Ep. 136
In this release, Jerry welcomes back close personal friend Brad Feld to the show. In his sixth Reboot Podcast appearance, Brad (author, and co-founder of Foundry Group and Techstars) introduces listeners to the concepts highlighted in his newest book, "The Startup Community Way." Jerry and Brad explore the impact COVID-19 has had on the state of work, and consider how virtual environments influence and enable connection across broader startup communities. They contemplate how the shift from pl...
Oct 30, 2020•53 min•Ep. 135
For many founders, the ups and downs of the startup rollercoaster feel like a natural component of the entrepreneurial journey, but what happens when the ride becomes too much and what's best for you, and the company, is to walk away? In this episode of the Reboot Podcast, Jerry sits down with Fritz Brumder, co-founder and former CEO of Brandlive. Fritz speaks candidly about his exit as CEO, describing how the process was simultaneously painful and relieving, and admits to the uneasiness that co...
Oct 13, 2020•52 min•Ep. 134
Along the entrepreneurial journey there comes a time and place for all leaders where we lift our heads from the fog of busyness to find ourselves on an unknown path. Knowing where we are isn't exactly where we intended to be, we look to the past for clues to how we've landed in this spot. For many, this is the integral moment in which we come to realize that our internal and external selves have fallen out of alignment. Our guest on this episode of the Reboot Podcast is Shizu Okusa, Founder &...
Sep 24, 2020•1 hr 1 min•Ep. 133
For this podcast release, Jerry sits down with David Sax to chat about his latest book, "The Soul of an Entrepreneur: Work and Life Beyond the Startup Myth." In their conversation, David outlines how the archetype of the hero entrepreneur has been glorified by Silicon Valley and illustrates how this particular prescriptive formula for startup success can be limiting and exclusionary for under-represented groups. David addresses how romanticizing the startup myth stymies creation and limits what ...
Sep 10, 2020•51 min•Ep. 132
What is psychological safety and why is it so important for the success of our teams? In this clip, Reboot Coaches Andy Crissinger and Ali Schultz, share what we can learn from horses about group dynamics and highlight some best practices for leaders looking to cultivate psychological safety in their teams and workplaces. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave ...
Sep 04, 2020•30 min
Joining Jerry on this episode of the Reboot Podcast is Leslie Feinzaig, Founder & CEO of the Female Founders Alliance, whose mission is to accelerate the success of venture-scale, women and non-binary founded companies. In this conversation, Leslie shares how attempting to lead and manage her team amongst the fallout of a global pandemic has led her to shift her thoughts to family in distant countries. The granddaughter of Holocaust refugees and a Costa Rican native, Leslie left her country ...
Aug 27, 2020•1 hr 9 min•Ep. 131
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 ...
Aug 13, 2020•52 min•Ep. 130
On this episode of the Reboot Podcast, we introduce you to Erine Gray, founder of Aunt Bertha, a nationwide search and referral platform for connecting people in need with available government and charitable programs. In his time with Jerry, Erine recounts growing up as a poor child in a small town and how the experience repeatedly left him feeling judged and unaccepted, triggering feelings of anger and shame. He opens up about his struggle to shake the underdog mentality and how it undermines h...
Jul 30, 2020•53 min•Ep. 129
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. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ ...
Jul 23, 2020•18 min
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, Co-founders of Evolving Dynamics, 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 ...
Jul 16, 2020•54 min•Ep. 128
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 rem...
Jun 26, 2020•54 min•Ep. 127
The fundamental unit of doing that great work is conversation. Conversations happen easier, clearer, and more harmoniously if we can connect as human beings, look each other in the eye, trust, and feel safe naming what's up for us. In this clip, coaches Andy Crissinger and Chris VandenBrink share Reboot's Red-Yellow-Green model for check-ins and how it's implementation can shift the tone of how you relate to folks and hold meetings such as 1-1's and offsites. Leave us a review on Apple Podcasts!...
Jun 18, 2020•17 min
On this episode of the Reboot Podcast, Jerry sits down with Rha Goddess, author, entrepreneurial soul coach, and founder of Move the Crowd. In this conversation, which centers around Rha's new book The Calling: 3 Fundamental Shifts to Stay True, Get Paid, and Do Good, Rha describes the ethos of soul work and shares why calling forth the qualities and attributes that live in the truest and purest expression of ourselves are crucial for those who lead. Jerry and Rha explore what it means to lead f...
Jun 12, 2020•54 min•Ep. 126
Feelings of isolation and loneliness have been well documented amongst today's leaders. That's why the simple question "Are you ok?", asked with genuine concern, can elicit such a profound impact for those who are struggling through a tough time, such as shutting down a business like Avni Patel Thompson. At the time of this recording, Avni was in the wake of shuttering her previous company, Poppy. In this exchange, Jerry and Avni discuss the trauma and pain that go hand in hand with closing a bu...
May 29, 2020•55 min•Ep. 125
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. Leave us a review on Apple Podcasts! Follow our step by step guides: - How To: Leave a Review on Your Computer: www.reboot.io/leave-itunes-review-via-computer/ - How To: Leave a Review on Yo...
May 21, 2020•17 min
