The journey of a Brooklyn boy – Jason Calacanis

Jason Calacanis is one of the guy among the geeks who started with zero, made millions lost it & ended up as a millionaire investor at the age of 46.

A true story of life and a blog post can’t explain the journey of a Brooklyn boy who started working as a waiter, selling copies of “Empire Strikes Back” in 80’s, fixing laser printers in computer lab to working at Amnesty International as a PC specialist for 10 bucks an hour.

Calacanis said in an exclusive interview to Alyson Shontell – Editor in Chief, Business Insider – “it’s a trait that people either love me or hate me for. I’ve calmed down a little bit since, so the edge has been taken off, but yeah, for a long time, I felt very powerless, and I was very scared of being broke because when you have no money — if you’ve ever had that experience where your parents are fighting over having no money and you can’t fix your car or you can’t pay the mortgage, it’s pretty terrorizing for a 10-year-old or an 8-year-old just to witness that and I realize, now at the age of 46 — my God — I was just scared to death of being poor and I was scared to death of being a failure.

A lot of the fire that I had that people saw early on, which looked kind of spastic at times or charming or just offensive depending on the day you caught me, was really just my own fear of just, “My God — being poor sucks.” And so I just worked really hard with Silicon Alley Reporter and some of the other businesses to try to be powerful because I was a kid who had no power. “  

His interest on magazines and internet made him start his very first venture Silicon Alley Reporter in 1995 and when the company started earning nice shares, he got an offer of $20 million to sell the magazine but as a young kid he turned the offer down and then the dotcom bubble burst and he ended up selling it for nothing. It was a lesson for him as an entrepreneur which pushed him to start Weblogs Inc. & within 18 months after launching the magazine started generating revenue of $ 100,000 with hundreds of thousands of people checking down weekly. It was pretty great that there was no competition that time & when he received an offer of $30 million from AOL, without making any mistakes

About his first investment on Uber, he said to Alyson Shontell

“I loved the idea from the get-go because I suffer from motion sickness pretty horribly — it’s like my Achilles’ heel. So I would spend a hundred bucks on car service because they had really beautiful cars, and I sat in the front with a driver who was professional. When I saw that the same driver was using Uber but charging $60 or $70 for the ride, I was like, this is incredible.

I don’t have to have my assistant or have to call ahead and book the person and have wait time. I just call it on demand. It was just obvious this was going to be a huge win, and the billing was all automatic and I could see the receipt and I could see the route and I was like, oh my god, this solves so many problems.

So I thought it was a billion-dollar company, candidly. But the thing about angel investing, which I get into in the book a lot is, you actually don’t have to understand the idea, you don’t have to know if the idea is going to win, you just need to know if the person’s going to win in their life, and for someone like Travis, he’s a winner, he’s going to win. I can just tell by looking at somebody if they’ll be successful in their life. I don’t even have to have a conversation. I just look at their eyes while they’re talking and it becomes very clear to me.”  

And now Uber it’s a $67 billion company which made his fortune as predicted.


He even bought the first Tesla, the serial number is 00001 and there is a great story behind it of friendship which he shared in the interview-  “I was out at dinner with Elon and Tesla was going out of business; they had three weeks of capital left, it was the financial crisis, and SpaceX had just blown up the second or third rocket.

We were eating a steak together in Hollywood and I said, “What’s going on with SpaceX?” He said, “Oh I just blew up the third rocket.” I said, “Whoa, that sucks.” I said, “What happens if you blow up a fourth?” He’s like, “Game over, you know, it’s not going to continue.” He got that fourth rocket up.

I said, “What’s going on with Tesla? Is it true you only have four weeks of capital left?” He says, “Not true.” I said, “Oh great.” He said, “We have three.” I said, “Oh sh–.” Like, that was bad. I said, “What are you going to do?” And he said, “Well, a friend of ours is giving me a loan to cover my personal expenses.”

He was negative a billion, and a friend of ours basically gave him a loan. I said, “Elon, there’s got to be some good news.” He said, “Yeah, don’t tell anybody but let me show you this.” He takes out his BlackBerry and starts showing me the clay version of the Model 3. It was a full-size clay model, like people standing around it. I said, “That’s gorgeous — how much can you make it for?” He’s like, “Well, it’s going to go 200 miles — I think we can make it for $50,000 or $60,000,” and I was like, “Nice.”

I went home, I wrote two full checks for $50,000, and I wrote him a handwritten note. “Elon, looks like an incredible car … I’ll take two! Best, Jason.” Two or three years later, I get “Congratulations, your serial number is 00001,” “Congratulations, your serial number is 00073.” I have No. 1, but I just saw Elon tweeting about the fact that he has No. 1 of the Roadster and No. 1 of the X, but he doesn’t have No. 1 of the model S, so I told him he could have it back.”

He says “if Elon wants it, he can have it and he can have it for free, of course. He’s my friend.”


A big thanks to Alyson Shontell for interviewing him and letting the world know about Calacanis’s journey which will surely inspire young people to go out leave their dreams & never to give up on situations.

 Image Source :The Full Ratchet

by Pranoy Maitra, The Blogging Connection

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