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Where does it say he was a couch surfer?. The title the submitter chose seems a bit of an ad hominem.
It's implied, but not explicitly stated, in paragraph 20:

> Uber moved back to Omaha because "I knew I could go from couch to couch to couch"

"couchsurfing" is a worldwide community of people that is quite different from just going from couch to couch.
"Couch surfing" is a slang term for being homeless (by choice or necessity) and moving from couch to couch. This term predates couchsurfing.com.
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This is bizarre. The guy in charge is spouting gibberish.
What are we supposed to take away from this article? The journalist didn't get this dude Chet to state one single actual substantiated thing about anything at all.

Man, I'm sick of watching professional journalists write articles about computers full of quotes like "We've found people attacking from Kuala Lumpur. Here's the attack pattern."

His name is "Chet Uber"?!?! He's the ultimate Chet?!?! "Chester Superior"

My uncle Chet is going to raise hell when he finds out there's a Chet claiming to be a better Chet than he.