Welcome back to today's deep dive. I am really
excited about this one because we are looking
at a guy who has practically shapeshifted right
alongside the Internet itself. Yeah, it is a
wild trajectory. It really is. We are pulling
from a comprehensive Wikipedia biography today
on Jason Calacanis. And, you know, if you have
ever been curious about how someone actually
builds real influence in Silicon Valley, this
is the deep dive for you. Absolutely. Our mission
today is to trace the anatomy of a career built
on just constant reinvention. I mean, from the
early dot -com boom in New York City all the
way to the absolute peaks of venture capital
and tech startups. It's essentially a map of
how the Internet evolved. Right. OK, let's unpack
this. So when you look at Calacanis' career.
It really is tracing the last 30 years of online
media. You go from print newsletters to blogs,
then to web directories, and finally to podcasts.
He didn't just passively watch these shifts happen.
He aggressively put himself in the center of
them. Which is fascinating when you look at his
origins. He was born in 1970 in Bay Ridge, Brooklyn.
He has this half Greek, half Irish background.
But the detail that really stands out from the
source is his education. He got a B .A. in psychology
from Fordham University. Not computer science.
Exactly. Not finance, not engineering. And honestly,
that might be the key to everything he did later.
We always treat tech like it is this purely mathematical
field. But venture capital, investing in tech
startups, it is fundamentally a behavioral science.
Oh, that makes a lot of sense. You are dealing
with human founders. You have to read what motivates
them or predict how consumers will react to a
product. The psychology degree gives you that
framework for weeding people. And you see him
applying that hustle and that people reading
skill immediately. Back in the 1990s, he starts
out as a reporter covering the Internet in New
York. Which they called Silicon Alley back then.
Yes, Silicon Alley. And in 1996, he founds Rising
Tide Studios and launches the Silicon Alley Reporter.
But I want to emphasize the sheer scale of the
hustle here for you listening. This was not a
polished website. No, not at all. It started
as a 16 -page photocopied newsletter. He is literally
making this thing at a copy machine. Just stapling
pages together. But that is the brilliant part.
He was throwing these massive parties and networking
events alongside it. He actually earned the nickname
the yearbook editor of the Silicon Alley community.
The yearbook editor. I love that. Because if
you catalog who is who, you become the toll booth.
Everyone has to come to you to find out what
is going on. And he grew that photocopied zine
into a 300 -page magazine. He even did a West
Coast version. But then the dot -com crash happens.
Print media takes a hit. He has to pivot. Right.
He pivots hard. In 2003, he co -founds Weblogs
Inc. with Brian Alvey. To get it going, he brings
in angel money from Mark Cuban. Which, again,
that is the 90s networking paying off. He could
just call Mark Cuban. Seriously. And they start
building this network of niche blogs. Now, the
source has this incredible stat. By just pumping
out targeted content and putting Google AdSense
on the pages, they were generating $1 ,000 a
day. Which in the early 2000s is just massive
for a lean digital operation. Huge! And legacy
media totally missed this, but Time Warner's
AOL saw it, and in 2005, they bought... Weblogs
Inc. for $25 to $30 million. A massive win. Completely
life changing. He even stays on briefly as AOL
CEO of Weblogs and the general manager of Netscape.
But he doesn't stay long. No, he steps down in
2006. And here's where it gets really interesting.
He leaves corporate life to join Sequoia Capital
as what they call an entrepreneur in action,
an EIA. What's fascinating here is the leverage
of that position. Sequoia is arguably the top
venture capital firm in the world. As an EIA,
you are essentially a scout. You sit in on pitches,
you give operational advice, but mostly you get
to see the best early stage deal flow on earth.
You are in the room. You are in the room before
anyone else even knows the room exists. And because
he was in that room, he meets a founder named
Travis Kalanick. Yep. Kalanick is pitching a
black car service. Calacanis decides to write
a $25 ,000 check through that EIA program. And
that company was Uber. And this is the magic
of the Angel Investor Power Law. You can sell
a blog network for $30 million, and that is fantastic.
But getting into Uber at the ground floor? The
numbers are just mind -boggling. The source notes
that by 2017, that specific $25 ,000 investment
was worth roughly $100 million. $100 million
from $25 grand. That is the kind of perfectly
timed check that just defines an entire career.
It really is. It turned him into a Silicon Valley
legend. But it is not all smooth sailing from
there. Not every bet is an Uber. No. Definitely
not. Because right after that, he launches into
what the source describes as this massive web
directory called Mahalo. Hawaiian for thank you.
Right. Mahalo. This was 2007. And he raises $20
million for this. The backing is insane. Sequoia,
News Corp, CBS, Mark Cuban again, Elon Musk.
The concept was human curated search results
to fight spam. And it was working for a bit.
They hit 15 million unique monthly visitors.
They even became profitable in 2011. They did.
But then came the brutal defeat. And this is
a terrifying lesson in platform risk for anyone
listening. Google rolled out an algorithm update
called Google Panda. The Panda Crush. Yeah. Google
decided they needed to penalize what they called
thin content or content farms. Because Mahalo
was mostly human -written summaries and links,
the algorithm basically swept them up in that
net. It wiped out their search traffic overnight.
When your entire business model relies on Google
sending you people and Google changes the rules,
you are done. Exactly. The traffic just fell
off a cliff. And despite all that $20 million
backing, Mahalo had to be shut down in 2014.
But you have to look at the resilience here.
The broader picture of tech is that you take
these massive hits and you keep moving. He pivoted
to Inside .com, raising $2 .6 million for thematic
newsletters. He always bounces back. Oh, and
I have to mention this quirky detail from the
source around 2007. started this internet trend
called fat blogging. Fat blogging, yes. He was
trying to lose weight, so he would exercise and
then publicly post his weight online to get community
support. Which sounds so casual now, but think
about that. He was building community accountability
mechanics way before apps like Strava made it
a standard feature. He just inherently understood
internet culture. He did. But going into the
late 2000s, his biggest disruption was going
to be in the venture capital space itself. He
became this sort of angel agitator. Right. He
was very vocal. In 2009, he founded the Open
Angel Forum. And the reason why is so revealing.
He was absolutely furious about these pay to
pitch forums. Oh, those were terrible. These
groups were charging startups anywhere from $1
,000 to $8 ,000 just for a 10 to 15 minute presentation.
It is entirely predatory. You have founders who
are broke trying to build a company and the investors
are treating them like the revenue stream. Exactly.
So he creates the open angel form to destroy
that model. He stops the fees. And founders obviously
love this. He built this massive, heavy hitting
portfolio. Robin Hood, Wealthfront. Yes. Descott
Metals, Superhuman. He invested in Calm, the
meditation app, which ended up reaching a $1
billion valuation. And he didn't just invest
quietly. He raised a $10 million fund. specifically
to write checks for startups at his own launch
conference. Small checks, 25 to 100 grand. He
even wrote a book in 2017 just called Angel,
laying out his whole playbook. But when you operate
like that, loud, aggressive, calling out industry
norms, you are going to make enemies. Oh, venture
capital is a very small, quiet club. You are
not supposed to yell. And he yells. The source
highlights two major feuds that really show this
friction. First, in 2016, Sam Altman, who was
running Y Combinator at the time, actually banned
Calacanis from attending YC's demo day. Right.
And Y Combinator is the most prestigious startup
accelerator in the world. Altman said the ban
was because of negative feedback they got from
their own founders about his behavior. Exactly.
And then in 2018, he takes on Mark Zuckerberg.
He publicly announced he sold all his Facebook
stock. He goes on a podcast and calls Zuckerberg
completely immoral. He actually warned founders
to never sell their companies to him. See, in
the tight knit world of Silicon Valley, holding
strong public opinions like that is a massive
tradeoff. It creates incredibly loyal followers
who love the transparency, but it also creates
very powerful detractors. It does, which perfectly
explains his next major pivot into becoming a
media empire builder. If the traditional VC club
is mad at you, you just build your own microphone.
And his microphone is massive. Huge. He starts
this week in startups, or Twist, back in May
2009. His first guest was Brian Alvey, his old
Weblogs partner. And Molly Wood actually co -hosted
with him later on, up until 2023. Twist really
set the standard for tech podcasting. But the
real dominance came recently with the All In
podcast. This is with Shamath Palihapitiya, David
Sachs, and David Friedberg. That show shifted
the entire landscape. They aren't just reporting
on tech. They are four billionaires and massive
investors moving the markets with what they say.
They even held the all in summit in Miami in
2022. It is just a juggernaut. And the influence
of this group is so tangible. In 2022, when Elon
Musk bought Twitter, Calacanis and David Sachs
were right there helping him transition the company.
Right in the war room. Literally helping figure
out the management restructure. But with that
level of global visibility comes extreme scrutiny
of your personal network. Inevitably. Now, I
want to pause here for a second. For you listening,
we are impartially reporting the source material
today. We are not endorsing any political viewpoints
left or right. We are simply conveying the facts
provided in our biographical source. It is important
to look at the data objectively. Exactly. So
impartially reporting the facts from the text.
First, Calacanis was an early supporter and founder
of the effort to recall San Francisco District
Attorney Chesa Boudin in 2022. OK. Second, the
source notes he was listed as a contact in Jeffrey
Epstein's little. Black Book, which gained massive
public attention after Epstein's conviction and
death. This raises an important question about
hyper -networking. When someone's entire strategy
for 30 years is to be the yearbook editor to
catalog and connect with every single person
of wealth and influence, their address book is
going to include thousands of people. And mathematically,
you are going to find your associations, your
political actions, and even your contact lists
heavily scrutinized by the media. When you sit
at the center of the web, every strand is eventually
examined. That makes perfect sense. The network
is your greatest asset, but it also becomes public
record. Exactly. So what does this all mean?
If you take a step back and look at this entire
Wikipedia deep dive, Calacanis' career proves
that success in tech is almost never a clean,
straight line. Never. It is not about avoiding
controversies or somehow dodging algorithmic
disasters like Google Panda crushing Mahalo.
It is about an absolute relentless drive to place
bets. He shifted from print magazines to blogs
to massive audio empires. And through all of
it, he leveraged his network to make sure he
was always in position for that one lucky $25
,000 check. That is the ultimate takeaway, the
resilience and the adaptability. But it does
leave you with a fascinating angle to consider.
What's that? Well, when you look at a career
spanning photocopied newsletters to billion -dollar
podcasting syndicates, you have to ask yourself,
is the ultimate skill in Silicon Valley predicting
the technology itself? Or is it simply predicting
where human attention is going to shift next?