1. Jason Calacanis on $100K to $100M

Brooklyn Roots

Jason Calacanis shares his experiences growing up in Brooklyn during the late seventies and early eighties. He describes the socio-economic challenges and the vibrant, yet dangerous atmosphere of the time. Jason's upbringing in a diverse and tough environment shaped his resilience and adaptability, which later influenced his career path 1.

I grew up in Brooklyn when it was dangerous and authentic and blue collar, not hips. We had no hipsters back then. Zero hipsters.

--- Jason Calacanis

His Greek heritage and the blue-collar nature of Brooklyn during that era played a significant role in his formative years.

   

From Crime to Capital

Jason's early exposure to crime and law enforcement significantly influenced his initial career aspirations. He recounts how his father's bar was frequented by both criminals and police officers, providing him with a unique perspective on law and order 2. This environment initially led him to consider a career in law enforcement before he transitioned to entrepreneurship.

My instructions were to give them a bill, and the bill would be $10 each so they could drink and eat whatever they wanted for $10.

--- Jason Calacanis

These experiences taught him valuable lessons about resilience and dealing with adversity.

   

Purpose and Resilience

Jason's career has been marked by significant transitions, from journalism to entrepreneurship and finally to investing. He emphasizes the importance of purpose and resilience in achieving success. Jason believes that having a clear purpose is crucial for enduring challenges and staying motivated 3.

You have to be able to disconnect yourself from failure and not take it so personally that it doesn't, it keeps you from going on to the next big thing in your life.

--- Jason Calacanis

His ability to bounce back from setbacks has been a key factor in his career development.