The Reboot Podcast

Be Without Deception Being without deception is an extension of telling the truth: it is based on being truthful with yourself. When you have a sense of trusting your own existence, then what you communicate to other people is genuine and trustworthy. -Chogyam Trungpa Rinpoche In 19 years of friendship and partnership in the startup world, these two have seen just about everything. In this conversation they share some stories from the Flatiron Partnership days, what makes a perfect board, the importance of trust in investing, and what makes a good leader. They even discuss the sheer terror they felt on their own entrepreneurial journey. In what we hope will be a series of several, enjoy this first Reboot conversation with Fred Wilson and Jerry Colonna.

“Knowing yourself is the beginning of all wisdom.” ― Aristotle For notes and more: http://www.reboot.io Entrepreneur and CEO Blaine Vess has an impressive story. Studymode, the company he helped start and bootstrap from his dorm room almost 16 years ago, now has 30 employees and sees between 60-90M visitors a month. It’s rare to find 15 year old bootstrapped companies. It’s rare to have the same CEO for 15 years as Blaine has been. But last year, Blaine wanted more for his company and himself. He wanted to know how to help push his company to the next level. To achieve that, he didn’t look elsewhere, he looked within. In this conversation, Jerry and Blaine talk about Blaine’s “year of introspection”. It included a stop at one of our bootcamps, working with a coach and a therapist, and that year ultimately helped him understand how and why he was holding himself back. Perhaps Blaine and Jerry’s conversation, our first of 2015, may spark your own year of introspection.

After years of rapid growth and expansion, followed by a serious year of depression, Rand Fishkin, founder and former CEO of Moz, found himself in a room surrounded by VC backed CEO’s and entrepreneurs where the question was posed: “How many of you struggle seriously with depression or severe anxiety or emotional issues?” He watched almost every person raise their hand. It’s shocking how universal depression is in startups. For anyone struggling with depression, it’s helpful to know you’re not alone. In this podcast, which is slightly different than past episodes, Jerry converses with Rand about his experience - his “loop,” how shame and guilt are at times his driver, the importance of understanding one’s emotional state, and how he’s made progress in coming out of his own depression, including his one piece of advice for entrepreneurs or anyone dealing with their own depression.

Do you have an innate desire to make people happy? And does that desire at times cause you to at hold back the truth, out of fear of perhaps hurting others and yourself? Carm Huntress is the CEO of RxReview, a company solving a big problem with big data - overspending on prescription drugs. The company started in January 2012 and is growing beyond it’s 11 employees. Carm realizes his nature as a people pleaser affects his leadership in detrimental ways. In this episode, Jerry and Carm unpack what it means to be fierce, and what’s behind the desire to make people happy. It’s a conversation that will leave you asking: “What if I led from a place where I knew I was good and also know there are things I want to do better?”

Joseph Chura is the founder and CEO of 2 startups that employ nearly a combined 100 people, yet he feels a constant drive for more. In this conversation with Jerry, Joseph shares his struggles to be present, especially at home with his wife and kids and they explore the question: Why is the drive to succeed, the itch to not sit still, so strong?

How can you save a business from the brink of bankruptcy and grow it 2,000% in 10 years, and yet feel like it could all go away in any given moment? Or face the fear, the weight, that you must be chief breadwinner...for you, your family, your co-founder and team’s family as well? Fear is pervasive in our lives, and in the crazy world of startups and entrepreneurship it is an always present participant. In this episode, we have two entrepreneurs dealing with two different and yet similar fears, fears that entrepreneurs will know all too well.

As CEO of a young startup, you can often feel what you are facing right now can make or break your company, can make or break you. And you will likely find yourself in this place more than once. Nigel Sharp, CEO of Armenian based Lion Sharp, finds himself in one of these very moments. He feels the energy of a promising product, and the reality of 6 months of runway. How do you balance the excitement and challenges? How do discuss the reality of your finances with your team? How do you discuss your fears, not only of failure but of success?

Duncan Morris, by any measure, had achieved a great deal success as co-founder and CEO of the international, 60 employee, online marketing agency - Distilled.net. And yet, something felt off for him. At our bootcamp in June he was touched and challenged by a question from Jerry: “What if you could truly understand who you are, and lead from that place?” In evaluating this question, a new question emerged for Duncan: “What if I don’t want to be a leader of a company with 60+ people?” In this conversation with Jerry, hear how exploring these questions has ultimately changed his work, his company, and his life.

Derek Flanzraich, CEO of one of the fastest growing health and wellness sites, Greatist, joins Jerry for this episode to share the story of his personal journey over the last 10 months. His journey of introspection started when he attended a CEO bootcamp last October and begin to reflect on a personal challenge, which ultimately lead him to a solution to a business challenge that could have destroyed his business. Derek’s openness and introspection is inspiring, and will inspire you to re-examine how your own stories impact your business and your life.