These are the important questions and only one investor is brave enough to ask.

It's hard to cast a better clusterfuck—or a worse caricature of Silicon Valley hustle—than what happened to tech investor Jason Calacanis. "Someone hacked my voicemail and changed my outgoing message to get me to invest," he wrote on Instagram yesterday, along with a recording of the new message.

About a year ago, millionaire tech investor and adult-sized baby Jason Calacanis proclaimed a simple message: if you're not successful in this country, you're not working hard enough. Every bias and bigot-ism is just an obstacle to hop over. This week he's at it again. Why is anyone still listening?

Let's put it this way: long-ago-successful venture capitalist Jason Calacanis isn't the absolute smartest man in the business. Otherwise, he probably wouldn't obviously post anonymously to Secret after the covert app rejected a slot on his podcast.

Entrepreneur and investor Jason Calacanis offered an exquisite example of the dangers created by loosening the rules around crowd-funding. During a PandoMonthly fireside chat last night, Calacanis not only argued that any consumer knows how to pick a winning startups, but that the populist thing to do is to let the masses bet on them.

Jason Calacanis, who once made a popular thing many years ago and has since been a go-to authority on race relations and poker, is ready with his forecast for the future of Google Glass. There's some bad news: the face computer's ruining his dance floor vibes, and he just might "punch you in the face" over it.

my World Series of Poker shirt: couldn't find $10k sponsorl;sponsored myself! still time left if u want your logo! pic.twitter.com/ACEZRzmyHH

If you're willing to ignore the existence of institutionalized prejudice and hustle, you might be the recipient of some cold cash from dot-com millionaire Jason Calacanis' impending investment firm. Let's hope he picks young startups better than he picks poker hands.