The Rise of Calacanis

1. 0:00 – 0:31

   Brooklyn upbringing and a family financial crisis before college

   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."

2. 0:31 – 1:28

   Working by day, college at night: learning hustle through laser printers

   1. JCJason Calacanis0:31

      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

3. 1:28 – 1:59

   Early exposure to computers, modems, and the conviction tech would change everything

   1. JCJason Calacanis1:28

      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-

   2. BGBen Gilbert1:47

      What-

   3. 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.

   4. BGBen Gilbert1:57

      Oh.

   5. JCJason Calacanis1:58

      So-

   6. BGBen Gilbert1:58

      He, he must have cleaned up on that.

4. 1:59 – 3:02

   Teenage entrepreneurship and gray-area tech: copying software and phone phreaking

   1. 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-

   2. BGBen Gilbert2:15

      You told us about the, the VHS-

   3. JCJason Calacanis2:17

      So VHS-

   4. BGBen Gilbert2:17

      ... relay

   5. JCJason Calacanis2:17

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

   6. BGBen Gilbert2:19

      [laughs]

   7. 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.

   8. 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-

   9. JCJason Calacanis2:36

      Yeah

   10. DRDavid Rosenthal2:36

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

   11. JCJason Calacanis2:39

       We soldered chips sometimes. We changed-

   12. DRDavid Rosenthal2:40

       Yeah. Like-

   13. 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.

   14. 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-

   15. JCJason Calacanis2:56

       Yeah

   16. 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"?

5. 3:02 – 3:36

   Choosing media over engineering: discovering zines as proto-blogs

   1. 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.

   2. BGBen Gilbert3:16

      Yeah.

   3. 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.

   4. DRDavid Rosenthal3:25

      It's like blogs before blogs.

   5. 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.

   6. DRDavid Rosenthal3:36

      Yeah.

6. 3:36 – 3:51

   Early collaborators and future internet-media lineage (Brian Alvey and beyond)

   1. JCJason Calacanis3:36

      And I did it with my friend Brian Alvey, uh, whom you might have heard of in my career.

   2. DRDavid Rosenthal3:41

      Yeah.

   3. BGBen Gilbert3:41

      He-

   4. JCJason Calacanis3:41

      We went to high school together

   5. BGBen Gilbert3:42

      ... did weblogs maybe?

   6. JCJason Calacanis3:43

      We did weblogs together, yeah. So, but in the early '90s, I did, which is-

   7. DRDavid Rosenthal3:47

      Engadget, TWAD.

   8. JCJason Calacanis3:48

      All of that stuff. Uh-

   9. DRDavid Rosenthal3:49

      Yeah

   10. JCJason Calacanis3:50

       ... TurboState.

   11. DRDavid Rosenthal3:50

       Everything you sold to AOL.

7. 3:51 – 4:38

   Breaking into venture orbit: meeting Jerry Colonna and Fred Wilson (future Flatiron)

   1. JCJason Calacanis3:51

      Things I sold to AOL. Uh, but anyway, before that, I did this mag... I did that magazine, and then I had met Fre- I met Jerry Colonna at, uh, Internet World, the first one, and he, there was a booth.

   2. DRDavid Rosenthal4:02

      That's right, when Jerry was a VC before he was, like, the-

   3. JCJason Calacanis4:05

      Before he was a VC-

   4. DRDavid Rosenthal4:06

      ... whisperer of startup coaches

   5. JCJason Calacanis4:06

      ... he was consulting for Lycos, and I think CMGI-

   6. DRDavid Rosenthal4:08

      Oh, nice

   7. JCJason Calacanis4:09

      ... did it. And so there was a Lycos booth, and I had met this young lady at it, and we hit it off, and we're talking, and then she introduced me to Jerry Colonna. And then I met Jerry Colonna in an office no bigger than this room in, on, uh, Union Square, and he said, "Listen, I'm leaving Lycos, but I'm gonna start this Acme Ventures with my friend Fred. Um, I want you to come, um, read business plans for us." And so I met Fred Wilson, and I would go up to them, and they were doing, JP Morgan was gonna back them for their venture firm. This was 1994, '95.

   8. BGBen Gilbert4:34

      This became Flatiron.

   9. JCJason Calacanis4:34

      It became Flatiron.

   10. DRDavid Rosenthal4:35

       JP Morgan-

   11. BGBen Gilbert4:36

       Which was the-

   12. DRDavid Rosenthal4:36

       ... was the first big anchor of Flatiron?

8. 4:38 – 5:14

   The Flatiron backing story and the GeoCities moment

   1. JCJason Calacanis4:38

      They were half of it, and Masayoshi Son, SoftBank, was the other half.

   2. DRDavid Rosenthal4:41

      No way.

   3. JCJason Calacanis4:42

      No shit.

   4. BGBen Gilbert4:42

      So they wanted you to come, like, be a VC associate.

   5. JCJason Calacanis4:44

      Not a VC, just to read business plans.

   6. DRDavid Rosenthal4:46

      [laughs]

   7. JCJason Calacanis4:46

      So the deal was they would take me for sushi and pay me 1,000 bucks-

   8. DRDavid Rosenthal4:49

      Wait, what do VC associates do-

   9. JCJason Calacanis4:50

      ... to read business plans

   10. DRDavid Rosenthal4:50

       ... besides just read business plans?

   11. JCJason Calacanis4:51

       Exactly.

   12. DRDavid Rosenthal4:52

       [laughs]

   13. JCJason Calacanis4:52

       Well, anyway, it was a thing, and so I had the magazine started, Silicon Eye Reporter, and they were paying me, and so I read, uh, about this, um, um, Beverly Hills internet company, which got rebranded as GeoCities.

   14. BGBen Gilbert5:04

       Oh.

   15. JCJason Calacanis5:04

       And I wrote a little coverage of it, and I said, "You should invest."

   16. DRDavid Rosenthal5:06

       Oh.

   17. JCJason Calacanis5:06

       I'm 24 years old. I don't even know what a VC is.

   18. DRDavid Rosenthal5:08

       That's where Flatiron made all their money.

   19. JCJason Calacanis5:10

       Yeah. Uh, they were gonna invest anyway, so-

   20. DRDavid Rosenthal5:12

       But Flatiron became SV, right?

   21. JCJason Calacanis5:14

       Yeah

   22. DRDavid Rosenthal5:14

       ... Silicon Valley Ventures?

9. 5:14 – 6:15

   Mentorship and the fork: Fred Wilson challenges him to choose a path

   1. JCJason Calacanis5:14

      Flatiron went with Jerry Colonna. Then when Jerry decided he wanted to move to Colorado and just chill-

   2. DRDavid Rosenthal5:19

      Yeah

   3. JCJason Calacanis5:20

      ... um, he had made enough money, I think, and-

   4. DRDavid Rosenthal5:22

      Coach founders.

   5. JCJason Calacanis5:23

      Coach founders, I think, and yeah, maybe he had, like, uh, I think he's been pretty public about it, like, I don't wanna say a nervous breakdown, but a kind of, like, maybe a fork in the road, like making a decision about what you want in your life kind of situation.

   6. BGBen Gilbert5:34

      He wrote that great book about it.

   7. JCJason Calacanis5:35

      Yeah, yeah, yeah. And so Jerry was a good mentor, but Fred actually became ultimately my, my deep mentor, uh, at that time. And, uh, Fred said to me, "Listen, you're doing Silicon Eye Reporter. You're writing about us and the companies we're investing in, and, um, you're doing stuff. Which do you would rather do?" And I was like, "I think I'll do the magazine."

   8. BGBen Gilbert5:53

      Wow.

   9. JCJason Calacanis5:53

      Uh-

   10. BGBen Gilbert5:53

       This was before. Now it's like-

   11. DRDavid Rosenthal5:54

       Wow. So that was so-

   12. BGBen Gilbert5:54

       ... I do both. [laughs]

   13. JCJason Calacanis5:56

       And now it's like I do both. Yeah.

   14. DRDavid Rosenthal5:57

       Yeah.

   15. JCJason Calacanis5:57

       Why choose?

   16. BGBen Gilbert5:57

       But ju- just to back up to GeoCities.

   17. JCJason Calacanis5:59

       Yeah.

   18. BGBen Gilbert5:59

       That sold to Yahoo for, like, three-

   19. JCJason Calacanis6:00

       Five billion

   20. BGBen Gilbert6:01

       ... and-

   21. JCJason Calacanis6:02

       I think four or five

   22. BGBen Gilbert6:02

       ... Flatiron was the main investor.

   23. JCJason Calacanis6:04

       Yeah, Flatiron maybe owned 5 or 10% of it, I think.

   24. BGBen Gilbert6:06

       Oh, crap.

   25. JCJason Calacanis6:06

       It was, like, a huge win for them. I mean, Fred was on fire. For a New York VC and Jerry, they did pretty well. They had done-

   26. BGBen Gilbert6:10

       How did that happen, right? Like, I mean, Silicon Valley-

   27. JCJason Calacanis6:13

       So-

   28. BGBen Gilbert6:13

       ... was here, but they-

   29. JCJason Calacanis6:14

       Yeah

   30. BGBen Gilbert6:14

       ... were in New York. Like, what was going on?

10. 6:15 – 6:49

    Owning New York’s internet beat: scaling niche publishing into a real business

    1. JCJason Calacanis6:15

       Yeah, we just, there was a lot of good companies brewing in New York, and my concept with Silicon Eye Reporter was, well, they have Red Herring and-

    2. DRDavid Rosenthal6:22

       In the Bay Area

    3. JCJason Calacanis6:22

       ... Upside in the Bay, but I own New York, and I had Silicon Eye Reporter. And then I started one called Digital Coast Reporter in LA. So I had two magazines, two conferences, two email newsletters. I was kind of king of New York, right? I grew that business to $10 million in revenue off my credit cards.

    4. DRDavid Rosenthal6:38

       Damn.

    5. JCJason Calacanis6:38

       Um, and, um, had, uh, 75 to 100 people working for me when I was 27 years old, and I didn't know anything about how to run a magazine, how to run ad sales. I taught myself everything.

11. 6:49 – 7:45

    Sudden prominence in the dot-com era: media fame and the ‘New York internet guy’

    1. BGBen Gilbert6:49

       What'd your family think of this? Like...

    2. JCJason Calacanis6:50

       It was pretty heady stuff because I wound up being on the cover of The New York Times, on Charlie Rose, and they wrote a feature story, me, about me for 8,000 words in The New Yorker. So anyway, it's a really cool time in New York because at that time you were either in media or finance or art, publishing. It was like a s- finite set, and I was in publishing, but I was also in this new thing, technology.

    3. DRDavid Rosenthal7:08

       Mm.

    4. JCJason Calacanis7:09

       And so everybody wanted in on that. It would be like the equivalent of crypto is today-

    5. DRDavid Rosenthal7:15

       [laughs]

    6. JCJason Calacanis7:15

       ... like, at its peak, where, like, and you were the equivalent of, like, Satoshi or something. Like, it was crazy to be-

    7. DRDavid Rosenthal7:23

       Yeah

    8. JCJason Calacanis7:23

       ... the New York internet guy.

    9. SPSpeaker7:26

       [upbeat music] Who got the truth? Hmm. Is it you? Is it you? Is it you? Sit me down, say it straight. Another story on the way. Who got the truth? Who got the truth now? Hmm.

Episode duration: 7:46