WEBVTT 00:00:00.000 --> 00:00:03.000 Welcome back to today's deep dive. I am really 00:00:03.000 --> 00:00:05.360 excited about this one because we are looking 00:00:05.360 --> 00:00:08.820 at a guy who has practically shapeshifted right 00:00:08.820 --> 00:00:11.060 alongside the Internet itself. Yeah, it is a 00:00:11.060 --> 00:00:13.080 wild trajectory. It really is. We are pulling 00:00:13.080 --> 00:00:15.800 from a comprehensive Wikipedia biography today 00:00:15.800 --> 00:00:19.079 on Jason Calacanis. And, you know, if you have 00:00:19.079 --> 00:00:21.300 ever been curious about how someone actually 00:00:21.300 --> 00:00:24.179 builds real influence in Silicon Valley, this 00:00:24.179 --> 00:00:26.589 is the deep dive for you. Absolutely. Our mission 00:00:26.589 --> 00:00:29.850 today is to trace the anatomy of a career built 00:00:29.850 --> 00:00:33.130 on just constant reinvention. I mean, from the 00:00:33.130 --> 00:00:35.950 early dot -com boom in New York City all the 00:00:35.950 --> 00:00:38.689 way to the absolute peaks of venture capital 00:00:38.689 --> 00:00:40.990 and tech startups. It's essentially a map of 00:00:40.990 --> 00:00:43.189 how the Internet evolved. Right. OK, let's unpack 00:00:43.189 --> 00:00:44.990 this. So when you look at Calacanis' career. 00:00:45.560 --> 00:00:47.880 It really is tracing the last 30 years of online 00:00:47.880 --> 00:00:51.060 media. You go from print newsletters to blogs, 00:00:51.079 --> 00:00:53.399 then to web directories, and finally to podcasts. 00:00:53.840 --> 00:00:56.500 He didn't just passively watch these shifts happen. 00:00:56.679 --> 00:00:58.920 He aggressively put himself in the center of 00:00:58.920 --> 00:01:00.640 them. Which is fascinating when you look at his 00:01:00.640 --> 00:01:03.659 origins. He was born in 1970 in Bay Ridge, Brooklyn. 00:01:03.939 --> 00:01:06.420 He has this half Greek, half Irish background. 00:01:07.000 --> 00:01:09.519 But the detail that really stands out from the 00:01:09.519 --> 00:01:13.500 source is his education. He got a B .A. in psychology 00:01:13.500 --> 00:01:16.200 from Fordham University. Not computer science. 00:01:16.459 --> 00:01:19.859 Exactly. Not finance, not engineering. And honestly, 00:01:20.060 --> 00:01:22.239 that might be the key to everything he did later. 00:01:22.579 --> 00:01:26.420 We always treat tech like it is this purely mathematical 00:01:26.420 --> 00:01:30.359 field. But venture capital, investing in tech 00:01:30.359 --> 00:01:33.959 startups, it is fundamentally a behavioral science. 00:01:34.159 --> 00:01:35.920 Oh, that makes a lot of sense. You are dealing 00:01:35.920 --> 00:01:39.500 with human founders. You have to read what motivates 00:01:39.500 --> 00:01:42.140 them or predict how consumers will react to a 00:01:42.140 --> 00:01:44.719 product. The psychology degree gives you that 00:01:44.719 --> 00:01:46.920 framework for weeding people. And you see him 00:01:46.920 --> 00:01:48.879 applying that hustle and that people reading 00:01:48.879 --> 00:01:52.000 skill immediately. Back in the 1990s, he starts 00:01:52.000 --> 00:01:54.140 out as a reporter covering the Internet in New 00:01:54.140 --> 00:01:56.180 York. Which they called Silicon Alley back then. 00:01:56.200 --> 00:01:59.859 Yes, Silicon Alley. And in 1996, he founds Rising 00:01:59.859 --> 00:02:03.099 Tide Studios and launches the Silicon Alley Reporter. 00:02:03.379 --> 00:02:05.340 But I want to emphasize the sheer scale of the 00:02:05.340 --> 00:02:07.640 hustle here for you listening. This was not a 00:02:07.640 --> 00:02:09.780 polished website. No, not at all. It started 00:02:09.780 --> 00:02:13.860 as a 16 -page photocopied newsletter. He is literally 00:02:13.860 --> 00:02:16.919 making this thing at a copy machine. Just stapling 00:02:16.919 --> 00:02:19.259 pages together. But that is the brilliant part. 00:02:19.379 --> 00:02:21.639 He was throwing these massive parties and networking 00:02:21.639 --> 00:02:24.840 events alongside it. He actually earned the nickname 00:02:24.840 --> 00:02:27.680 the yearbook editor of the Silicon Alley community. 00:02:27.939 --> 00:02:30.159 The yearbook editor. I love that. Because if 00:02:30.159 --> 00:02:32.599 you catalog who is who, you become the toll booth. 00:02:33.519 --> 00:02:35.180 Everyone has to come to you to find out what 00:02:35.180 --> 00:02:37.960 is going on. And he grew that photocopied zine 00:02:37.960 --> 00:02:40.680 into a 300 -page magazine. He even did a West 00:02:40.680 --> 00:02:43.719 Coast version. But then the dot -com crash happens. 00:02:44.139 --> 00:02:47.259 Print media takes a hit. He has to pivot. Right. 00:02:47.560 --> 00:02:51.419 He pivots hard. In 2003, he co -founds Weblogs 00:02:51.419 --> 00:02:54.400 Inc. with Brian Alvey. To get it going, he brings 00:02:54.400 --> 00:02:56.580 in angel money from Mark Cuban. Which, again, 00:02:56.639 --> 00:02:58.840 that is the 90s networking paying off. He could 00:02:58.840 --> 00:03:01.080 just call Mark Cuban. Seriously. And they start 00:03:01.080 --> 00:03:03.340 building this network of niche blogs. Now, the 00:03:03.340 --> 00:03:06.219 source has this incredible stat. By just pumping 00:03:06.219 --> 00:03:08.919 out targeted content and putting Google AdSense 00:03:08.919 --> 00:03:11.900 on the pages, they were generating $1 ,000 a 00:03:11.900 --> 00:03:14.199 day. Which in the early 2000s is just massive 00:03:14.199 --> 00:03:18.139 for a lean digital operation. Huge! And legacy 00:03:18.139 --> 00:03:20.580 media totally missed this, but Time Warner's 00:03:20.580 --> 00:03:24.129 AOL saw it, and in 2005, they bought... Weblogs 00:03:24.129 --> 00:03:29.250 Inc. for $25 to $30 million. A massive win. Completely 00:03:29.250 --> 00:03:32.330 life changing. He even stays on briefly as AOL 00:03:32.330 --> 00:03:35.150 CEO of Weblogs and the general manager of Netscape. 00:03:35.250 --> 00:03:37.409 But he doesn't stay long. No, he steps down in 00:03:37.409 --> 00:03:40.129 2006. And here's where it gets really interesting. 00:03:40.569 --> 00:03:43.710 He leaves corporate life to join Sequoia Capital 00:03:43.710 --> 00:03:45.830 as what they call an entrepreneur in action, 00:03:45.990 --> 00:03:48.810 an EIA. What's fascinating here is the leverage 00:03:48.810 --> 00:03:51.919 of that position. Sequoia is arguably the top 00:03:51.919 --> 00:03:54.580 venture capital firm in the world. As an EIA, 00:03:54.819 --> 00:03:57.120 you are essentially a scout. You sit in on pitches, 00:03:57.219 --> 00:04:00.379 you give operational advice, but mostly you get 00:04:00.379 --> 00:04:02.840 to see the best early stage deal flow on earth. 00:04:03.000 --> 00:04:04.780 You are in the room. You are in the room before 00:04:04.780 --> 00:04:07.020 anyone else even knows the room exists. And because 00:04:07.020 --> 00:04:08.860 he was in that room, he meets a founder named 00:04:08.860 --> 00:04:11.419 Travis Kalanick. Yep. Kalanick is pitching a 00:04:11.419 --> 00:04:13.680 black car service. Calacanis decides to write 00:04:13.680 --> 00:04:17.399 a $25 ,000 check through that EIA program. And 00:04:17.399 --> 00:04:20.029 that company was Uber. And this is the magic 00:04:20.029 --> 00:04:22.759 of the Angel Investor Power Law. You can sell 00:04:22.759 --> 00:04:25.439 a blog network for $30 million, and that is fantastic. 00:04:25.699 --> 00:04:28.639 But getting into Uber at the ground floor? The 00:04:28.639 --> 00:04:30.879 numbers are just mind -boggling. The source notes 00:04:30.879 --> 00:04:34.579 that by 2017, that specific $25 ,000 investment 00:04:34.579 --> 00:04:38.240 was worth roughly $100 million. $100 million 00:04:38.240 --> 00:04:41.060 from $25 grand. That is the kind of perfectly 00:04:41.060 --> 00:04:44.139 timed check that just defines an entire career. 00:04:44.319 --> 00:04:46.220 It really is. It turned him into a Silicon Valley 00:04:46.220 --> 00:04:48.920 legend. But it is not all smooth sailing from 00:04:48.920 --> 00:04:51.670 there. Not every bet is an Uber. No. Definitely 00:04:51.670 --> 00:04:54.069 not. Because right after that, he launches into 00:04:54.069 --> 00:04:56.329 what the source describes as this massive web 00:04:56.329 --> 00:04:59.209 directory called Mahalo. Hawaiian for thank you. 00:04:59.350 --> 00:05:02.449 Right. Mahalo. This was 2007. And he raises $20 00:05:02.449 --> 00:05:05.430 million for this. The backing is insane. Sequoia, 00:05:05.449 --> 00:05:08.709 News Corp, CBS, Mark Cuban again, Elon Musk. 00:05:08.889 --> 00:05:11.769 The concept was human curated search results 00:05:11.769 --> 00:05:13.850 to fight spam. And it was working for a bit. 00:05:13.949 --> 00:05:16.569 They hit 15 million unique monthly visitors. 00:05:16.730 --> 00:05:19.769 They even became profitable in 2011. They did. 00:05:20.360 --> 00:05:24.120 But then came the brutal defeat. And this is 00:05:24.120 --> 00:05:26.379 a terrifying lesson in platform risk for anyone 00:05:26.379 --> 00:05:29.379 listening. Google rolled out an algorithm update 00:05:29.379 --> 00:05:33.240 called Google Panda. The Panda Crush. Yeah. Google 00:05:33.240 --> 00:05:35.339 decided they needed to penalize what they called 00:05:35.339 --> 00:05:38.839 thin content or content farms. Because Mahalo 00:05:38.839 --> 00:05:40.839 was mostly human -written summaries and links, 00:05:41.000 --> 00:05:43.259 the algorithm basically swept them up in that 00:05:43.259 --> 00:05:45.519 net. It wiped out their search traffic overnight. 00:05:46.199 --> 00:05:49.319 When your entire business model relies on Google 00:05:49.319 --> 00:05:51.620 sending you people and Google changes the rules, 00:05:51.860 --> 00:05:53.980 you are done. Exactly. The traffic just fell 00:05:53.980 --> 00:05:56.000 off a cliff. And despite all that $20 million 00:05:56.000 --> 00:05:59.120 backing, Mahalo had to be shut down in 2014. 00:05:59.720 --> 00:06:01.259 But you have to look at the resilience here. 00:06:01.360 --> 00:06:03.379 The broader picture of tech is that you take 00:06:03.379 --> 00:06:06.100 these massive hits and you keep moving. He pivoted 00:06:06.100 --> 00:06:09.720 to Inside .com, raising $2 .6 million for thematic 00:06:09.720 --> 00:06:11.819 newsletters. He always bounces back. Oh, and 00:06:11.819 --> 00:06:13.720 I have to mention this quirky detail from the 00:06:13.720 --> 00:06:16.519 source around 2007. started this internet trend 00:06:16.519 --> 00:06:19.120 called fat blogging. Fat blogging, yes. He was 00:06:19.120 --> 00:06:21.279 trying to lose weight, so he would exercise and 00:06:21.279 --> 00:06:23.639 then publicly post his weight online to get community 00:06:23.639 --> 00:06:26.360 support. Which sounds so casual now, but think 00:06:26.360 --> 00:06:28.800 about that. He was building community accountability 00:06:28.800 --> 00:06:31.800 mechanics way before apps like Strava made it 00:06:31.800 --> 00:06:34.139 a standard feature. He just inherently understood 00:06:34.139 --> 00:06:37.259 internet culture. He did. But going into the 00:06:37.259 --> 00:06:39.800 late 2000s, his biggest disruption was going 00:06:39.800 --> 00:06:43.160 to be in the venture capital space itself. He 00:06:43.160 --> 00:06:46.079 became this sort of angel agitator. Right. He 00:06:46.079 --> 00:06:48.980 was very vocal. In 2009, he founded the Open 00:06:48.980 --> 00:06:52.540 Angel Forum. And the reason why is so revealing. 00:06:52.860 --> 00:06:55.779 He was absolutely furious about these pay to 00:06:55.779 --> 00:06:57.480 pitch forums. Oh, those were terrible. These 00:06:57.480 --> 00:06:59.779 groups were charging startups anywhere from $1 00:06:59.779 --> 00:07:03.839 ,000 to $8 ,000 just for a 10 to 15 minute presentation. 00:07:04.560 --> 00:07:06.879 It is entirely predatory. You have founders who 00:07:06.879 --> 00:07:09.920 are broke trying to build a company and the investors 00:07:09.920 --> 00:07:11.680 are treating them like the revenue stream. Exactly. 00:07:11.899 --> 00:07:13.779 So he creates the open angel form to destroy 00:07:13.779 --> 00:07:16.680 that model. He stops the fees. And founders obviously 00:07:16.680 --> 00:07:19.060 love this. He built this massive, heavy hitting 00:07:19.060 --> 00:07:21.959 portfolio. Robin Hood, Wealthfront. Yes. Descott 00:07:21.959 --> 00:07:25.160 Metals, Superhuman. He invested in Calm, the 00:07:25.160 --> 00:07:27.160 meditation app, which ended up reaching a $1 00:07:27.160 --> 00:07:30.360 billion valuation. And he didn't just invest 00:07:30.360 --> 00:07:34.329 quietly. He raised a $10 million fund. specifically 00:07:34.329 --> 00:07:36.709 to write checks for startups at his own launch 00:07:36.709 --> 00:07:40.209 conference. Small checks, 25 to 100 grand. He 00:07:40.209 --> 00:07:42.410 even wrote a book in 2017 just called Angel, 00:07:42.610 --> 00:07:45.129 laying out his whole playbook. But when you operate 00:07:45.129 --> 00:07:48.029 like that, loud, aggressive, calling out industry 00:07:48.029 --> 00:07:51.170 norms, you are going to make enemies. Oh, venture 00:07:51.170 --> 00:07:53.930 capital is a very small, quiet club. You are 00:07:53.930 --> 00:07:56.750 not supposed to yell. And he yells. The source 00:07:56.750 --> 00:07:59.129 highlights two major feuds that really show this 00:07:59.129 --> 00:08:02.740 friction. First, in 2016, Sam Altman, who was 00:08:02.740 --> 00:08:05.180 running Y Combinator at the time, actually banned 00:08:05.180 --> 00:08:07.879 Calacanis from attending YC's demo day. Right. 00:08:07.920 --> 00:08:09.959 And Y Combinator is the most prestigious startup 00:08:09.959 --> 00:08:12.579 accelerator in the world. Altman said the ban 00:08:12.579 --> 00:08:14.339 was because of negative feedback they got from 00:08:14.339 --> 00:08:16.480 their own founders about his behavior. Exactly. 00:08:16.480 --> 00:08:19.319 And then in 2018, he takes on Mark Zuckerberg. 00:08:19.339 --> 00:08:21.259 He publicly announced he sold all his Facebook 00:08:21.259 --> 00:08:24.019 stock. He goes on a podcast and calls Zuckerberg 00:08:24.019 --> 00:08:27.000 completely immoral. He actually warned founders 00:08:27.000 --> 00:08:29.149 to never sell their companies to him. See, in 00:08:29.149 --> 00:08:31.310 the tight knit world of Silicon Valley, holding 00:08:31.310 --> 00:08:34.350 strong public opinions like that is a massive 00:08:34.350 --> 00:08:37.309 tradeoff. It creates incredibly loyal followers 00:08:37.309 --> 00:08:40.029 who love the transparency, but it also creates 00:08:40.029 --> 00:08:43.169 very powerful detractors. It does, which perfectly 00:08:43.169 --> 00:08:45.610 explains his next major pivot into becoming a 00:08:45.610 --> 00:08:48.720 media empire builder. If the traditional VC club 00:08:48.720 --> 00:08:50.580 is mad at you, you just build your own microphone. 00:08:50.779 --> 00:08:53.919 And his microphone is massive. Huge. He starts 00:08:53.919 --> 00:08:57.120 this week in startups, or Twist, back in May 00:08:57.120 --> 00:09:00.620 2009. His first guest was Brian Alvey, his old 00:09:00.620 --> 00:09:03.360 Weblogs partner. And Molly Wood actually co -hosted 00:09:03.360 --> 00:09:06.320 with him later on, up until 2023. Twist really 00:09:06.320 --> 00:09:08.539 set the standard for tech podcasting. But the 00:09:08.539 --> 00:09:10.539 real dominance came recently with the All In 00:09:10.539 --> 00:09:13.360 podcast. This is with Shamath Palihapitiya, David 00:09:13.360 --> 00:09:15.789 Sachs, and David Friedberg. That show shifted 00:09:15.789 --> 00:09:17.809 the entire landscape. They aren't just reporting 00:09:17.809 --> 00:09:20.529 on tech. They are four billionaires and massive 00:09:20.529 --> 00:09:22.629 investors moving the markets with what they say. 00:09:23.000 --> 00:09:25.200 They even held the all in summit in Miami in 00:09:25.200 --> 00:09:28.259 2022. It is just a juggernaut. And the influence 00:09:28.259 --> 00:09:31.220 of this group is so tangible. In 2022, when Elon 00:09:31.220 --> 00:09:33.820 Musk bought Twitter, Calacanis and David Sachs 00:09:33.820 --> 00:09:35.720 were right there helping him transition the company. 00:09:35.879 --> 00:09:38.059 Right in the war room. Literally helping figure 00:09:38.059 --> 00:09:40.279 out the management restructure. But with that 00:09:40.279 --> 00:09:43.779 level of global visibility comes extreme scrutiny 00:09:43.779 --> 00:09:46.559 of your personal network. Inevitably. Now, I 00:09:46.559 --> 00:09:49.159 want to pause here for a second. For you listening, 00:09:49.340 --> 00:09:51.600 we are impartially reporting the source material 00:09:51.600 --> 00:09:54.840 today. We are not endorsing any political viewpoints 00:09:54.840 --> 00:09:57.240 left or right. We are simply conveying the facts 00:09:57.240 --> 00:10:00.379 provided in our biographical source. It is important 00:10:00.379 --> 00:10:02.919 to look at the data objectively. Exactly. So 00:10:02.919 --> 00:10:04.899 impartially reporting the facts from the text. 00:10:05.240 --> 00:10:08.279 First, Calacanis was an early supporter and founder 00:10:08.279 --> 00:10:10.379 of the effort to recall San Francisco District 00:10:10.379 --> 00:10:14.700 Attorney Chesa Boudin in 2022. OK. Second, the 00:10:14.700 --> 00:10:17.100 source notes he was listed as a contact in Jeffrey 00:10:17.100 --> 00:10:19.500 Epstein's little. Black Book, which gained massive 00:10:19.500 --> 00:10:22.159 public attention after Epstein's conviction and 00:10:22.159 --> 00:10:24.600 death. This raises an important question about 00:10:24.600 --> 00:10:28.100 hyper -networking. When someone's entire strategy 00:10:28.100 --> 00:10:31.440 for 30 years is to be the yearbook editor to 00:10:31.440 --> 00:10:34.000 catalog and connect with every single person 00:10:34.000 --> 00:10:36.480 of wealth and influence, their address book is 00:10:36.480 --> 00:10:39.320 going to include thousands of people. And mathematically, 00:10:40.139 --> 00:10:42.419 you are going to find your associations, your 00:10:42.419 --> 00:10:44.960 political actions, and even your contact lists 00:10:44.960 --> 00:10:47.820 heavily scrutinized by the media. When you sit 00:10:47.820 --> 00:10:50.399 at the center of the web, every strand is eventually 00:10:50.399 --> 00:10:53.019 examined. That makes perfect sense. The network 00:10:53.019 --> 00:10:54.820 is your greatest asset, but it also becomes public 00:10:54.820 --> 00:10:57.000 record. Exactly. So what does this all mean? 00:10:57.159 --> 00:10:59.279 If you take a step back and look at this entire 00:10:59.279 --> 00:11:02.960 Wikipedia deep dive, Calacanis' career proves 00:11:02.960 --> 00:11:05.720 that success in tech is almost never a clean, 00:11:05.820 --> 00:11:08.529 straight line. Never. It is not about avoiding 00:11:08.529 --> 00:11:11.350 controversies or somehow dodging algorithmic 00:11:11.350 --> 00:11:13.529 disasters like Google Panda crushing Mahalo. 00:11:13.769 --> 00:11:17.169 It is about an absolute relentless drive to place 00:11:17.169 --> 00:11:20.769 bets. He shifted from print magazines to blogs 00:11:20.769 --> 00:11:23.730 to massive audio empires. And through all of 00:11:23.730 --> 00:11:25.730 it, he leveraged his network to make sure he 00:11:25.730 --> 00:11:28.629 was always in position for that one lucky $25 00:11:28.629 --> 00:11:31.629 ,000 check. That is the ultimate takeaway, the 00:11:31.629 --> 00:11:34.090 resilience and the adaptability. But it does 00:11:34.090 --> 00:11:35.850 leave you with a fascinating angle to consider. 00:11:35.990 --> 00:11:37.879 What's that? Well, when you look at a career 00:11:37.879 --> 00:11:40.519 spanning photocopied newsletters to billion -dollar 00:11:40.519 --> 00:11:43.000 podcasting syndicates, you have to ask yourself, 00:11:43.200 --> 00:11:46.279 is the ultimate skill in Silicon Valley predicting 00:11:46.279 --> 00:11:49.799 the technology itself? Or is it simply predicting 00:11:49.799 --> 00:11:52.080 where human attention is going to shift next?