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1.
To fail at something or to not achieve success consistently. A 'kaygo' will often live with their failure and eventually not even realize their mistakes. Instead living an oblivious existence.
"That guy is a total Kaygo"

"How Kaygo of you"
by lolcakez April 26, 2008
 
2.
Tech savvy, up-to-date, and overall winning. KayGo means the latest and the greatest news in all things tech, web, and social media. To be called KayGo pretty much means that you are a bright, charismatic, and forward-moving human being.
I KayGo, You KayGo. He, she, me, KayGo.

I WANT TO BE KAYGO.
by theonewiththehair123 November 03, 2011