Jason Calacanis

Worth Staying Up For

I was going to go to bed on time tonight, but I saw a lovely treat in my inbox from Fred Wilson's blog, so I'm staying up to watch that.  Usually I insist on 8 hours of sleep, but when there's an Fireside chat between your two favorite venture capitalists in your inbox, it's okay to only get 7.

But first- what a great day today- I woke up at 5, went to the gym, then went car shopping with my mom.  I'd gotten my car totalled a month ago, and she decided to help me out financially, and we finally hit a jackpot tonight.  My mom is a great stats person, and always makes up Excel spreadsheets for everything, and me, well, I just wanted a new car, so I was motivated to keep us focussed and just keep lining up the next viewing and the next viewing.  It turns out I'm quite comfortable negotiating too.  My birth chart says I'm bad at managing my own money and great at managing others' money, so I was dogged about keeping us under my mom's budget, and voila- LAST car of the day- my mom had a gut feeling about a car, we go to check it out, and this great young lady- a real credit to her parents who clearly raised her to think intelligently about finances- showed us an impeccable car that she took great care of over the years (and barely drove).  We made her a good offer and she accepted.  For two women who - let's talk Enneagram here for a second- who don't do power plays as first recourse- my mom and I were a solid team today and I'm proud of us. 

Now back to Fred Wilson and Jason Calacanis.  Back in 2011 when I left my government job, I became a bit of a tech nerd, I guess- my other passion besides the Enneagram and the Victoria's Secret franchise (I love the VC business, I love all things Victoria Secret, but I want people to know me first and foremost as someone who challenges them to look inward.  When I die, I want the bells to peal "Know yourself.  Know yourself". )

Anyway, in 2011, I developped a love affair with the internet and the people who invest in the technology that make the internet such a great place.  The article I read that got it all started was about a Jason Calacanis presentation to a computer science class at UPenn- I think I've written about it before- STILL the best pitch in my mind for entrepreneurship.  A must watch for all kids contemplating their direction in life after high school or university.  So I started watching Calacanis' TWIST videos, and when I started dating Mr. M, I connected him to this one interview between him and Brad Feld, another great investor in the Venture Capital field.  Which started us both just digging into this really exciting world of tech investments and the VC's who blog about it. 

One power couple we fell in love with was Joanne and Fred Wilson- proud New Yorkers, wife and husband, best friends, really sharp investors, and longtime bloggers who share their perspectives on new developments in technology.  Joanne, Fred, and their buddy Jason all got into the internet in New York in the late 90's when the first browser- Netscape- came out, made some good bets over the years, and have made very good return on their investments in the internet since.  So this fireside chat is Jason and Fred doing a retrospective of the last twenty years of their friendship and their investments- it's mostly about Fred, but you get to know Jason a bit here too.

One day I'm going to write about their Enneagram types.  Jason is a Type 7- probably a social/ sexual/self-preservation, and I'm still undecided about Fred's type- he could be an Eight or a One, but he's got two very important people in his life who are already Eights and Ones, so my back-up is Type Six, but he just doesn't worry enough to be a Type Six.  I just don't have enough information yet.

On the one hand, he could be a self-preservation One because I do see him being a body type, and he's about substance and "here"-ness, (not that that's a word, but his presence has heft to it, as opposed to buzzy and aversive head-space energy, or the ethereal and craving heart-space energy.)  However,  Fred's business partner, Brad, is definitely a Type One, and it would take some very special magic for two Type Ones to work together as effectively as they have over the years.  Fred and Brad definitely complement each other's strengths and weaknesses.

On the other hand, he could be a Type 8, but Joanne, his wife is a type 8.  I have a good mind that she's a social/self-pres Eight w Seven (although she could also be a 7w8), so because they also complement each other really well, it's possible he's also an Eight, but with an instinct stack of self-preservation/sexual or self-preservation/social. 

Fred is confident, has a drive toward "realness" and likes talking straight, getting to the point and cutting through bullshit.  He disdains fluff and goes with his gut- all Eight traits.  Another interesting trait- he and his wife don't invest in public markets because he doesn't like putting his money in with other people; for an Eight with the resources to make his wealth independently, you can see the type's signature survival instinct at play.  And then, some type Eights have this thing where they lower their forehead when they talk to you or pose for pictures, which you can see Fred doing in this interview- they've realized over the years that they come on too strong for some people and to minimize that effect, they unconsciously angle their head down, almost to prevent the intensity of their energy from drilling a hole in the other person.  Eights are intense whatever their instinct stack, and you get a taste of his intensity here, despite it being a laid-back interview.

So it's a really great, insightful chat between two long-time friends.  I hope you enjoy it.

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