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Almost all successful entrepreneurs will fail – if not fail, fail, fail, and fail again – on their path to success. Every human being made choices in their lives which they regret, are embarrassed of and have caused them deep shame. What would your life be like if you were known only by the worst thing you had ever done?
Catherine Hoke is the founder of Defy Ventures, a program that helps incarcerated individuals transform their hustle to entrepreneurial ventures. Following a chance visit (as a guest) to a prison at the age of 26, Catherine left behind a successful investment career to launch a program to build on what she recognized were valuable entrepreneurial skills – simply applied to illegal businesses. Through the journey of building two wildly successful organizations, Cat had her own personal experience of failure, great shame and having to grant herself grace, and a second chance.
Nestled in this conversation about failure, mercy and second chances, is an important second discussion. Joined by investor Brad Feld, this episode also includes a heartfelt reflection on the lottery of birth, acknowledging our own privilege, and what we can do when confronted with these realizations.