Reboot Podcast Episode #65 – What You Choose to Become – with Derek Flanzraich

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Episode 65 // July 27, 2017


Derek Flanzraich

Derek Flanzraich

CEO of Greatist

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Episode Description

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 our challenges at work lies a conversation about what impacted who we are and how we relate to life, work, 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.

Derek Flanzraich on Twitter | Kandinsky Squares with Concentric Circles

Show Highlights

Top Quotes:

“It was only then when I really realized where we were, and looked at the money in the bank, and said, “Well, we’re running out of money.” And, “how did this happen?”” – Derek Flanzraich

“What was the emotion that you felt when you realized that you’re running out of money and that you hadn’t been paying close enough attention to that?” – Jerry Colonna

“What is unreasonable is to expect that those personal constructs are not going to affect the business.” – Jerry Colonna

“The self-inquiry process is like “who the fuck am I” and “what am I working with here.” – Jerry Colonna

“You’ve got, from childhood, a very interesting relationship with money. …Which then led to not paying attention to the sustainability of the business.” – Jerry Colonna

“You cannot make an impact without creating wealth to support it.” – Derek Flanzraich

“The numbers didn’t mean anything to me …” – Derek Flanzraich

“What was so threatening to you about the notion of pursuing money for money’s sake that you would reject the discipline that financial discipline creates?” – Jerry Colonna

“I think the fear is that I can’t, that I am not like my dad: I can’t make money.” – Derek Flanzraich  

“The fear is the force in your head is telling you can’t.” – Jerry Colonna

“We all are wounded by our parents, and I say that as a parent.” – Jerry Colonna

“All of our work is to take what happened to us and shape our own self.” – Jerry Colonna

“…took me a long time to really understand that numbers and dollars are just another form of language that tell stories.” – Jerry Colonna

“The work of closing the wound in your heart is your work.” – Jerry Colonna

“The world was trying to define what healthy should look like for me, but I wanted to define what it looked like for myself.” – Derek Flanzraich

“Greatist – with an I-S-T – is someone who’s working on being their version of great, just like an artist works on art.” – Derek Flanzraich

“A universal truth is that we are not comfortable with who we are, and that we must rail against the world and as David Whyte says “and it’s hard need to define you.”” – Jerry Colonna

“Defy how other people are trying to define it for you.” – Derek Flanzraich

“Learning to push yourself but also accept yourself, to integrate the totality of who you are is a path to that, is what you would call being the greatest.” – Jerry Colonna

“All of our businesses, all of our heart, all of our expressions in the world are expressions of the inner landscape.” – Jerry Colonna

“Don’t even underestimate the power of your subconscious to give you exactly what you need when you need it, you just have to pay attention to those messages.” – Jerry Colonna

“Your job is to create a sustainable container for the business so that you can then achieve the purpose. ” – Jerry Colonna

“It’s about sustainability, it’s about making sure that there is a tomorrow in the company.” – Jerry Colonna

“Container without content is pointless. And content without container is ineffective. You need purpose, but you need the sustainable container. Otherwise, you’ll never deliver what you’re trying to deliver.” – Jerry Colonna