Part 1: Jason Calacanis, An Entrepreneur Is Born

Sunil Rajaraman: To anyone watching on he Internet or anywhere else, this event is not sponsored by UCLA, the UCLA Anderson School of Management, or the UC system. The views expressed during this event do not reflect those of the UCLA Anderson School of Management, UCLA, or the UC system. And for those of you who know me well, that's probably a good thing.

Jason Calacanis: We should get right into the talk about Palestine and Israel and the official position of UCLA on it. [laughter] Sorry, something less controversial.

Sunil: I didn't do the big intro for Jason, but as we all know he's done a great deal. Can you tell us a little bit about your background, where you came from, what you're doing, what you're working on?

Jason: Sure. I'm a serial entrepreneur. I've done, I guess three sort of major companies and a couple of small minor ones that I don't talk about because they failed. We'll talk about those tonight. It's great - entrepreneurs always forget the failures, or at least don't talk about them. I grew up in Brooklyn and I live in Brentwood now so if I ever write a book, "From Brooklyn to Brentwood" might be the title or something. I live right down the block and grew up with a mom who's a nurse and a dad who's a bartender, and the big aspiration was to become a cop or a lawyer, or a doctor or something like that.

So I took the policeman's test when I was 18 years old and my brother wanted to become a cop and I started fixing laser printers. So my first job in technology was fixing laser printers, which I don't know if you guys remember the HP Laser Jet 1, I don't know how old people are here, but it was about that big. [gestures] It broke every week. It broke about every 500 pages you printed. So that was my first job, and then I was in the right place at the right time, which was New York City in the early '90s when the economy was total shit and there were no jobs and it was brutal and you were lucky if you could get a $20,000/year job working at Conde Naste or something and you were really careful to not piss off, you know, your really horrible boss.

It was a really dark time and a lot of us had a lot of pent up energy so at night we'd play with computers. We played with things like Prodigy and CD-ROMs. Being there when the CD-ROM became the standard - you know, CD-ROMs didn't come in computers in 1988 and 1989. You had to put them in.

So in the early '90s in Manhattan, you had photographers and you had writers, you had Madison Avenue and advertising, and you had technology. These artists started using Macs and Photoshop and PageMaker to lay out newspapers. Then you could put an MP3 or a Wave file in. People started saying, "If you put these things together, what would it be?" That was multimedia. I was there right as that happened.

There was a company that was going to become the next Microsoft, the next big thing. It was called Voyager and they were - Does anyone know what the term Voyager is? There were two technologies at the time. One was laser disks and everyone thought laser disk was going to change the world because you could pause it and it would look perfect and there was that menu. You could skip ahead and behind. There were notes about the film and two audio tracks. It was a mindblowing technological advance that all these crazy people started to play with and this company called Voyager by this guy named Bob Stein on lower Broadway. He made a DVD called A Hard Day's Night about The Beatles. They made one for Bob Dylan and this was all the '94-'95 timeframe when they started making CD-ROMs, maybe '92-93. Electronic press kits on 3.5" floppies. And essentially what was was it's like a web page. You click on it, you listen to a wave file, you look at a picture, and you're like wow, I'm on a computer but I'm seeing pictures and text and video. Then people just started going, this is incredible. You can have this really amazing business. You can put this in boxes and give them out and sell them for $50.

That was actually the false start. It cost a quarter million dollars to make one of these things so you couldn't actually do it. But some people had the money to do it, they had venture capital to do it. And people would go buy a $60 CD-ROM - did anybody here buy a CD-ROM in the early '90s and put it in their computer? Anybody? You put it in and you were like, what am I doing here exactly? I could have turned on my TV, whatever. That was a massive false start that then, when the Internet came out, and I had been working at Sony fixing computers like an IT guy, and I knew what the web was. So I put the Mosaic browser on a machine because I had it in college and I knew how to use FTP and all those things and there was this moment where somebody had put up Billy Joel's, covers of his albums on a web page.

So at Sony the legal department was like, we gotta kill this guy. He's still the Billy Joel covers. Literally they were JPEGs this big [gestures]. So I set up a web browser on three peoples' computers and one of them was Micky Chewboff, then CEO of Sony. So I'm like this 24 year old kid and I'm explaining what the Internet is and they're like, okay it was like that scene in PeeWee Herman's big adventure you know where they're about to kill him in the bar and they're like, we should stab him and then they're like no, we should hang him, and then like no, we should hang him and then we should stab him. So they're talking about what they're going to do to this kid who built a web page with Billy Joel's album covers and tracks. That's all it was. They said what'll we do, how do we find him? And I said, why don't we hire him? And it was dead silence and they all looked at me. And then they're like agh, back to let's kill him.

But I realized I got myself entree into this incredible world when I was at Sony. And actually Elliott who's sitting right here and is Vice President of Operations at Mahalo hired me for my first job there, in 1994. So it's kind of interesting how that happens in your career, but that's when I started becoming an entrepreneur. It was inside of Sony because nobody knew what the Internet was and Sony had to deal with the Internet so I became friends with the head of Sony, this guy Micky Chewmoff.

I was out here and he was launching this thing called the Playstation for the first time. Just being at the right place at the right time and knowing about technology - I'm talking to him about the Internet and the Playstation and I get a phone call in my hotel. "Mr. Chewmoff would like you to fly back with him to New York." I'm like, oh my god. I'm like an IT guy at Sony. I'm not fixing printers, I'm fixing computers. It's a big jump. And the CEO is about 8 people above me. This is a place where the hierarchy is everythnig. You're not allowed on certain floors in the building, let alone to talk. So I'm talking to his assistant, I'm like, okay, um, I'm flying Delta. What is Mr. Chewmoff flying? They said, he's flying on the Sony jet. I said, Oh, when is it leaving? She said tomorrow. I said what time? She said tomorrow. I said okay, what do I do? She said be at the hotel. I said okay. I said oh, one more thing, what do I do with this ticket for Delta. It was like $300? She's like, rip it up? I was a naive kid, you know, a poor kid from Brooklyn, from humble beginnings.

All of a sudden, I'm on a G5 with the CEO of Sony talking about the future of the Internet. I'm sitting there with him, talking about the Internet, and he doesn't know what the Internet is. Nobody knows what the Internet is. I said well, there's this company I know called Lycos. There's three people working out in Boston. You should buy them. And I started talking about these Internet companies I knew that some of my friends were doing. He started saying, you know, there's this $50 million movie we're doing with Arnold Schwarzennegger, the Last Action Hero. I'm like, we should buy these companies for like a million dollars each and I started trying to get him into it and long story short, it didn't work out, but...

Part 2: Starting Up, What is a real Entrepreneur?

Part 3: Are you an Entrepreneur or a Fauxtrepreneur?

Part 4: Age and risk as an Entrepreneur.

Part 5: Keep your eye on the goal, there's no downside risk!

Part 6: The realities of internet celebrity.

Part 7: A country of opportunities. Get in the game!

Part 8: The realities of the international internet.

Part 9: Build a better brand. Be a lot better!

Part 10: Defining success for you and your company.