I spoke with an entrepreneur out of Detroit named Ray recently.  Ray owns an Allstate agency.  He drives a brand new Escalade that is a fleet vehicle from a side hustle transportation company he started.  He’s in the process of buying a large building for his agency.  Most of the space he’s going to lease to other businesses.  And he’s planning on having his company build him a house to live in which he’ll rent from the company.  

All of this is bank funded.  Ray exhorted me to take out a loan and buy something.  “It’s free money! Whatever you’ve been dreaming of doing you can do it!  Start a transportation company and buy that $100,000 Lamborghini you always wanted.  Develop some assets.”  

In my imagination, I was watching the bank take Ray’s home because his business had run up against some loss he hadn’t foreseen.

How affected by fear do you think you are?

How does fear impact your business decisions?

For myself, I’ve almost never felt scared or anxious in business, but fear has had a larger impact on my choices than any other factor.  Bigger than luck, bigger than the market, bigger than the limits of my skill or knowledge.

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