Apparently, rich people have the smallest penises. It makes sense why Bill Gates called it "MicroSoft."
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Explanation
Explain Bear
Listen up, buttercup! The joke implies that rich dudes are packin' little heat downstairs. "Explain bear" thinks that maybe the author of the joke is projecting and compensating. The punchline connects it to Bill Gates naming his company "MicroSoft," playing on the word "micro" meaning small. It's funny because it's an insult disguised as a business observation.