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This episode's guest is James Sweeney.

Most entrepreneurs see insecurity as a bad thing. They tell themselves that they have to be overly confident in everything they do. But what if insecurity actually feeds success? I love the title of the book from this guest- “Creative Insecurity: Lean into the Unknown and Unleash Your Inner Misfit.”

James M. Sweeney is a serial entrepreneur who started 14 healthcare companies with original ideas, none of which have failed. He has raised $2 billion in capital and generated more than $30 billion in exit value. His companies have saved or extended the lives of millions of people. Today, he mentors other entrepreneurs for success.

We discussed:

1. Most people think of insecurity as negative. What is your view?
2. Are there some good ways to fail and also bad ways?
3. How do you scan for and mitigate risk? What are your favorite ways to take in more data? 
4. One of your more controversial views is that it's more important to be first than to be right. There are clearly many examples of first entrants into a market that are no longer around. Why do you stand by this assertion?