5 Questions With Dan Schawbel

5 Questions With Dan Schawbel


Episode 208: Steve Case

October 10, 2022

My guest today is entrepreneur, investor, and philanthropist, Steve Case. Steve is best known as the co-founder of AOL. For the past 15 years, through his company Revolution, he invested $1 billion in companies like Sweetgreen and DraftKings. We talk about his new book “The Rise of the Rest” and his entrepreneurial journey, during this episode.



This episode is proudly sponsored by Proximity, a workspace management company that streamlines how companies operate and manage their hybrid workspace. Go to www.proximity.space/fivequestions for a free Workspace Efficiency Audit.





The 5 questions I ask in this episode:



  1. What were the key moments early in your career that shaped who you are as a businessperson today?
  2. What would you say are the biggest business and cultural changes that have affected how entrepreneurs create and scale their companies?
  3. How did the people you met during your Rise of the Rest tour help educate yourself on the current state of entrepreneurship?
  4. What are the biggest challenges that prevent people from being entrepreneurs and what can they do to overcome them?
  5. What’s your best piece of career advice?

Video interview:



Follow Steve’s journey: