Jason Calacanis is a smack-talking, poker-playing entrepreneur and angel investor. And he's been on a roll lately, thanks to some smart investments. He put money into Uber, which is now worth a fortune. Today it was reported that Raise, one of his other early investments, has raised money at a valuation of nearly $1 billion. In other words, he is striking gold all over the place.
But: While it is true that Jason Calcanis is now an incredibly wealthy man, he also came up hard — on the mean streets of Bay Ridge, Brooklyn. Now he is celebrating his accomplishments by spitting truth, in a rapper-style tweetstorm that gets a little bit, well ... uncomfortable.
Think Iggy Azalea, if Iggy Azalea were a middle-aged man. Below is that eight-part poetry slam tweetstorm that Calacanis threw down on Thursday, accompanied by analysis and translation for people unfamiliar with the argot of the streets:
In the past, some people in the venture community ignored me or were slow to return my calls. But now I have triumphed! I have mastered many modern forms of communication involving the Internet, and I have made a great deal of money. I no longer require your assistance.
Some of you may now call me or attempt to communicate to me via Twitter. Please do not, for I shall ignore your entreaties. Also, I have a wide network of associates, and we are very powerful. Indeed we are more powerful than you are.
Some traditional venture capitalists look down their noses at "angel" investors like myself. It is true that I do not possess as much wealth as some people. Nevertheless, I have accomplished great things by spotting opportunities sooner than others do.
Your shabby treatment of me in the past now reflects poorly on you, not on me. Also, I intend to steal business opportunities from you.
While you enjoy the wealth you have accumulated by visiting exotic locations typically frequented by wealthy, powerful individuals, I will be working.
You may have hoped that I would leave your industry. However, I am determined to stay and to continue annoying you. The performer in this video is one of my role models. Like me, he was a diligent young man from Brooklyn who achieved great things by working hard. His success rubbed some people the wrong way, but he did not care.
My role model was a rapper. Like him, I am a performer. My skills are greater than yours.
I realize that you probably find me obnoxious and don't like me. I am not bothered by that. I do not wish to be your friend. The man in this photo is also a performer and one of my role models. Like me, he grew up in Brooklyn and is now incredibly powerful.
Jason Calacanis founded Weblogs and sold it to AOL. He later founded Mahalo, and now runs a conference called LAUNCH. He is 44 years old.
[Photo by Christopher Michel, via Wikimedia.]