The Rise of Calacanis

1. JCJason Calacanis0:00

   In the '90s, um, I, you know, I grew up in Brooklyn. Um, my dad had his bar, uh, seized by the feds because he didn't pay his taxes during the 1987 crash. He became, like, he got behind, and, uh, the feds showed up one day, and this was the maybe six weeks before I was set to go to college. And he said, "Hey, son, I can't help you with college. Good luck. Uh, and, uh, I might be going to jail, so take care of your mom." So he was, like, really behind on his taxes, and, you know, state liquor authority, they kind of take it serious. So feds come, shotguns, the whole thing. They seize the place. They seize everything in it. And, uh, I was like, "Wow, I guess I'm going to school at night, and I'm gonna work during the day." And I worked, uh, fixing laser printers, and, uh, that was, like, a really good racket. The HP had just come out and-

2. BGBen Gilbert0:55

   Were you set to go to college somewhere else?

3. JCJason Calacanis0:57

   Well, that's another story. But I was set to go to Brooklyn College. I had gotten into that. I had also taken the police exam to be a police officer. So my brother went into the force, and then I said, "You know what? I'm gonna see if I can go to college and make that work. So I'm gonna go to Brooklyn College." So I decided to work during the day, and then I went to school four nights a week, 6:00 to 9:00 PM, carried full credit, 16 credits a semester, and, uh, I would work fixing laser printers all day. I was a bad student. Uh, I was always that student who underperformed. I didn't find great meaning in academics, but I had a computer when I was in high school, and I was more interested in playing with my 300 baud modem, which then became a 1200 baud modem in my PC junior. So it kinda, you know, like many people of that era, we were sort of set on a path because we were the first generation to have a computer at home. Uh, I actually had an Atari 2600-

4. BGBen Gilbert1:47

   What-

5. JCJason Calacanis1:47

   And it could play Tank, was the game that came with it, and Pong. And so my dad bought this for us when I was six or seven years old in 1976, 1977, and he had one of the first Pongs in Brooklyn in his bar.

6. BGBen Gilbert1:57

   Oh.

7. JCJason Calacanis1:58

   So-

8. BGBen Gilbert1:58

   He, he must have cleaned up on that.

9. JCJason Calacanis1:59

   Oh my God, it was crazy. Um, and so we, uh, I, I just got exposure to video games and computers, and I was like, "Wow, this is incredible." Like, computers are gonna change everything. And then I happened to hack some software. We used to... I ran a lot of scams. Uh, but, uh, [laughs] that-

10. BGBen Gilbert2:15

    You told us about the, the VHS-

11. JCJason Calacanis2:17

    So VHS-

12. BGBen Gilbert2:17

    ... relay

13. JCJason Calacanis2:17

    ... Jason's Hot Tapes was technically my first business.

14. BGBen Gilbert2:19

    [laughs]

15. JCJason Calacanis2:19

    But there was a side job I had, which was cracking software. So we were, we would make copies of, like, Chess Master and stuff like that, and then sell them for 10 bucks, and then we started, like, hacking and doing what was called phone phreaking.

16. DRDavid Rosenthal2:31

    When, when you were doing this stuff, like, it took you to be reasonably technical to do it, not like the, you know, not like-

17. JCJason Calacanis2:36

    Yeah

18. DRDavid Rosenthal2:36

    ... Wozniak technical, but, like, y- you-

19. JCJason Calacanis2:39

    We soldered chips sometimes. We changed-

20. DRDavid Rosenthal2:40

    Yeah. Like-

21. JCJason Calacanis2:41

    You know, we put, we, to put memory in at that time, you had to, like, take the memory chips and put them in and then bend them over and stick them in.

22. DRDavid Rosenthal2:48

    Did you ever think about, like, did, did you consciously ever make a fork where you were, like, not tech media, and of course, media about tech-

23. JCJason Calacanis2:56

    Yeah

24. DRDavid Rosenthal2:56

    ... but you're like, "I'm not gonna be the guy doing the boards. I'm gonna be the guy writing about the people doing the boards"?

25. JCJason Calacanis3:02

    It's a very good question. I used to go to Bleecker Street. I used to hang out in the West Village or the East Village. It was, like, the cool places to hang out, and, um, like, a thing to do would be to go to Tower Records and look at the zine section.

26. BGBen Gilbert3:16

    Yeah.

27. JCJason Calacanis3:16

    So there was a concept of a zine, which was short for magazine, but a zine was something you wrote with your friends. You printed it yourself at a photocopy store.

28. DRDavid Rosenthal3:25

    It's like blogs before blogs.

29. JCJason Calacanis3:26

    Blogs before blogs, and I created a zine. I was like, "I'm gonna be a magazine publisher." So the first one I did was CyberSurfer, which was about dial-up magazine, dial-up services and CD-ROMs.

30. DRDavid Rosenthal3:36

    Yeah.

Episode duration: 7:46