

#820 Can Insecurity Be Your Secret Weapon in Entrepreneurship?
Jan 16, 2025
15:48
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:
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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:
- Most people think of insecurity as negative. What is your view?
- Are there some good ways to fail and also bad ways?
- How do you scan for and mitigate risk? What are your favorite ways to take in more data?
- 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?
Become a supporter of this podcast: https://www.spreaker.com/podcast/the-small-business-radio-show--3306444/support.