Why you think it'll work: You think you see the world in a different way. You have a way with words. You heard that Kevin James bum makes $400K per episode of King of Queens and you deserve some of that syndication money.
Why it won't: The traditional method of touring comedy clubs is dead. So, there's that. If you go the webseries/viral video route it's a long play. Those Workaholics guys were life imitating art for years. Louis CK grinded for almost two decades before finding any real success and that guy's really funny. You're probably not that funny, you're just playing the odds.