Should you borrow money from pessimists because they don't expect it back?

In response to last week’s question, "Should you borrow money from pessimists because they don't expect it back?", my writing and sailing friend Rich responded, "The essence of giving without an expectation of return is charity. Would you deny the pessimist the pleasure of charitable giving? Not to mention the joy of the charitable tax deduction. The only way you could mess this up would be to defy pessimistic expectations and repay the loan with interest on which the pessimist will have to pay capital gains."

My dad's beach buddy Bob lamented, "Pessimists?  All my friends are bankers."

My CFO turned broadcaster friend Bill advised, "A pessimist is merely an optimist who once loaned money to a friend or family."   My golden retriever rescue friend Kate added, "A big YES to that question; but, you'll never hear the end of it."

My product mgmt friend, Doug, who recently moved to Austin recommends, "You should ALWAYS borrow money from pessimists.....  That's the only reason you have them for friends." 

My friend Chris shared, "Only if you are a pessimist yourself because you don't expect yourself to pay it back either :)  "  Yet my sailing friend Kurt challenged, "You can't borrow money from a true pessimist, they know they will not get it back so won't lend it in the first place."

My friend Richard summarized, "A pessimist would not lend any money because they are certain you won’t pay it back.  You borrow from optimists because they naively believe you will pay it back.  Before the economic collapse of 2008, banks were optimists, as evidenced by their insane lending practices and “creative” loans.  Now the banks are pessimists who won’t lend to anyone, no matter how solvent….   An optimist sees the glass as half full. A pessimist sees the glass as half empty.  A realist sees the class is cracked.  A cockeyed optimist realizes it’s a dribble glass."

Please share your thoughts about "things that make you go 'Hmmm' “:

            Should a business protect its customers 

       from the customer's own stupidity? (from my banking friend Ashley)

Love truly. Laugh uncontrollably. And never regret anything that made you smile!

Hal

Just thought I'd re-share my birthday bud Jon's conversation to eating grouper alone: 

PS:  I was floundering before I came up my answer. 

                   But you responded just for the halibut. 

                  You're giving me a haddock. 

[Thanks to Demetri Martin, Steven Wright and George Carlin for the inspiration.]