The Reboot Podcast

Adeesh Agarwal is an architect who has worked in real estate, med-tech, and had started and managed his own design firm, which recently closed it's doors. He finds himself soul searching at 40 years old looking back at the choices he's made to have a job and be a responsible caretaker for his family. He struggles with finding work that isn't soul-sucking, that creates safety and opportunity for his family, and wanting to have a sense of stability and sense of progress in his life. As he looks at his life and the choices ahead, he asks: Who am I? What are my strengths? Jerry and Adeesh talk about how there's a much deeper existential question behind those questions, and how a better question is to ask: What am I made of? And how do the aspects of me come together in ways that I am proud of and ways that hold me back?

Derek Flanzraich, CEO of one of the fastest growing health and wellness sites, Greatist, joined Jerry for our very first podcast episode in 2014 to share the story of his personal journey over the last 10 months. His journey of introspection started when he attended the first CEO bootcamp and began to reflect on a personal challenge, which ultimately lead him to a solution to a business challenge that could have destroyed his business. In this conversation, Jerry and Derek talk about how in our challenges at work lies a conversation about what impacted who we are and how we relate to life, work, and money. Derek's openness and introspection may inspire you to re-examine how your own stories, upbringing and past experiences are impacting your business and your life. Links Greatist - https://greatist.com/ Twitter - https://twitter.com/derekflanz - https://twitter.com/greatist

Nancy Lublin, CEO of Crisis Text Line, a non-profit that provides free 24/7 support at your fingertips, is a successful serial social entrepreneur. Previously at Dress for Success and Do Something, her journey as a CEO has been one towards a more authentic and human style of leadership. This journey has informed how she see's her product and the companies she runs. In this candid conversation with Jerry Colonna, Nancy talks about what it means to be a social entrepreneur and being human centric in this world of chat bots, numbers, OKRs and KPIs. Links Crisis Text Line - http://www.crisistextline.org/ Nancy Lublin on Twitter - https://twitter.com/nancylublin

Throughout his life Adi Mashiach has been a brilliant student, a successful doctor, and has experienced two successful company exits. Along with his wife Mirella, Adi has stepped into the world of VC with the creation of Mesia Ventures. Having just moved to the United States less than a year ago with his family, Adi has started to feel the familiar pangs of belonging trying to break into new circles and begin building a new venture fund. Recently, Adi has begun to wonder how to live his passion for helping others, and how to fit in without losing himself in the fire (something he's experienced twice before in his life). In this episode, Jerry Colonna and Adi discuss how our intellect can help us figure out only so much in life, and how listening closely to our heart can reconnect us with the forgotten parts of ourselves that, once reclaimed, can sit beside us as we endeavor through life. Links Love after Love by Derek Walcott - https://onbeing.org/blog/love-after-love

In an entrepreneurial world where being a billionaire is a yardstick for self-worth, and unattainable goals can give us a false sense of responsibility, control and drive, what is the collateral damage to ourselves? As we chase a sense of perfectionism, and measure ourselves against big goals, how do we counteract the sense of self-loathing we can impinge upon ourselves when we fall short of the images we're up holding? In this conversation, Jerry sits down with Sharon Salzberg, on her new book "Real Love: The Art of Mindful Connection" to discuss the ways in which love might be a counter-intuitive antidote to the ups and downs of entrepreneurship. We learn that as we cultivate a sense of love and compassion for ourselves in our ambitious pursuits and adventures in life, we bolster our resiliency to face life as it is. Links "Real Love: The Art of Mindful Connection" by Sharon Salzberg - https://www.amazon.com/Real-Love-Art-Mindful-Connection/dp/1250076501 Sharon Salzberg on Twitter - https://twitter.com/SharonSalzberg #22 – Does Anyone Really Know What They Are Doing? – with Sharon Salzberg - https://www.reboot.io/episode/does-anyone-really-know-what-they-are-doing/

Sally Spencer-Thomas is a psychologist who found herself in a moment in which she was not prepared when her brother died of suicide. After that significant event in her life, Sally poured much of her life into engaging leaders and finding bold, gap-filling solutions for suicide prevention in schools, workplaces, and communities. Driven by the memory of her brother, Sally dove into her work, and along the way, she found a community and purpose around her brother's legacy. Over the last 14 years, Sally encountered her own onerous moments of depression. From these moments, she came to understand the power of community and the importance of a caring person. On her journey, Sally has become more attuned to asking, "What is this moment teaching me? What can I do to learn here?" a testament to her resilience. Now, she's facing big life transitions in both her work and her role as a parent, and she finds herself listening for what her inner voice is saying as she's wondering, "Who am I, now, in this season of my life?"

Khe Hy spent 14 years in Financial Services and was successful by all signs, but his work and life felt 'meh.' Something felt disconnected from him as he suited up in the morning and turned off the finance switch in the evening. He opted for a life of more meaning, and started RadReads, a passion project now grown into a community of sorts. But something still didn't feel right for Khe. Even though he preached a lot about what's important, he found that a hard talk to walk and instead found himself putting the most important things in his life - his wife and daughter - last on his list of priorities. Despite all of Khe's efforts in meditation, mindfulness and reflection, he struggled to figure out how to be present for his life. Instead he found himself thinking about ideas, people in his network, and ways to improve. As a self-proclaimed life-hacker, he struggled to find the metrics and hacks to be present. As Khe and Jerry discuss, perhaps the answer to being present is deeper than hacks and metrics. Perhaps the clue lies in what he's so afraid of. Links RadReads - https://radreads.co/ Khe Hy on Twitter - https://twitter.com/khemaridh

Al Doan led his family's fledgling small town quilting shop to a leading online retailer with over 450 employees in just a few short years. To the outside world, this rapid growth established Al has a wildly successful and admired leader, but behind closed doors Al was struggling. He found himself behaving in ways contradictory to his character and struggling to feel happy and content. Sure, he was killing it as an online quilting retailer, but was this really what he wanted his life to be? Recognizing things were not working, he reached out for help from a trusted friend and advisor. This friend connected Al with Jerry, leading to a new journey of self-inquiry and discovery for Al. A journey that has ultimately led him to walk through the fear and challenge of stepping down as CEO, to create the space for the life of his dreams to emerge. Links Missouri Quilt Company - https://www.missouriquiltco.com/ Al Doan on Twitter - https://twitter.com/drbillnye Signs you need to leave your startup - https://goo.gl/Q0YmtO CEO bootcamp - https://www.reboot.io/service/bootcamps/ Reboot Circles - https://www.reboot.io/service/peer-groups/ Episode #29 Who's in your corner? With Carrie Barry - https://www.reboot.io/episode/29-whos-in-your-corner-with-carrie-barry/

Simon Cant's path to becoming a VC has been a windy road. Building on a career that includes stints as a lawyer, founder, consultant, director of a non-profit and advisor, he is now an LP in Reinventure, an Australian fintech fund. Alongside his meandering career path, Simon has battled to slow the swing between a strong desire to exert control and an acute awareness of his own need to surrender. In this conversation Jerry leads Simon to remember that there is no such thing as a perfect surrender. Instead, surrender is a lifelong practice. Links Grace, VC and Surrender - https://hackernoon.com/grace-vc-and-surrender-4475a6c1e325#.hqn5apr6h Simon Cant on Twitter - https://twitter.com/simoncant

"If we have no peace, it is because we have forgotten that we belong to each other." - Mother Teresa For Bijan Sabet- an investor, US citizen by birth and descendant of Korean and Iranian immigrants- the January 27th Trump administration issue of an executive order banning the entry of residents and refugees from a number of Muslim countries deeply disturbed him for a number of reasons. Recalling his own early experience of being othered as the child of an Iranian immigrant during the Iran Hostage Crisis of the late 70s, his heart broke that other. Driven to mobilize his heart ache to action the best way he knew how, he launched a fund matching campaign for the ACLU. Bijan's initial expectations of a several month timeline to raise the funds were blown away when the campaign received overwhelming support and reached its goal (and beyond) in less than 3 days. In this conversation, Jerry and Bijan discuss the experience of feeling othered and how that changes what it feels like to belong. The shame and embarrassment of feeling different or outside, and the healing that occurs when we find ourselves on the other side- feeling a part of and knowing we are not alone anymore. Links Bijan Sibet on Twitter - https://twitter.com/bijan "Not Alone Anymore" - https://goo.gl/HXRgxH Episode #20 Investors Are Human Too - https://www.reboot.io/episode/investors-are-human-too/ Episode #19 Building a House of Belonging - https://www.reboot.io/episode/building-a-house-of-belonging Stickball - https://en.wikipedia.org/wiki/Stickball