From Skeptic to Supporter: How This Billionaire Got ‘Red-Pilled’ by Trump
242 segments
what was your red pill moment was there
one specific thing or was it more of a
trickle of things it was both right it's
like it starts the wall starts crumbling
and then it comes down all at once so
for me it really
started early in 2013 I started reading
pirate wires and Mike salana and I
thought he was a little crazy at first
because he would write these articles
one he wrote was about how the Ukrainian
soldiers had swastikas on their helmets
and the New York times photographers
would ask them to take the swasa off for
photos and I said that can't be right
that can't be true and then four months
later it was in the New York Times
buried in the middle of the paper and I
kept seeing stories like that that that
he would be early on and so I just
started feeling uncomfortable and Queasy
about what was going on with mainstream
media and then in May of last year of 24
I read some article that talked about
Trump's speech in Charlottesville and
this has been well covered but but where
he said there was good people on both
sides and the article said it was
completely you know propaganda and not
what he actually not accurately
reflecting what he said that uh that he
denounced the Nazis a bunch of times in
his speech and so then I went and
watched that video and that was my red
pill moment I think it was for a lot of
people because it wasn't just the media
spinning it or politicians spinning it
that was like one of the pillars of why
you were supposed to hate Trump was that
speech and and then you
see Biden say that's why he had to run a
second time and you see Obama go to you
even see Biden bring it up again in the
beginning of the DNC and it's one of
their pillars and they clearly know that
they're misrepresenting things so for me
that was just that was beyond
uncomfortable I was just like okay now I
got to go back to First principles and
look at the primary data and listen only
to original speeches by people and I
just realized I couldn't trust
mainstream media so I was I became I
started questioning the Democrats as
soon as I started questioning the
Democrats I started getting a lot of
Shame and anger and hatred oh the other
thing that happened that was part of
this journey is that my chief of staff
parted ways with me after nine years in
April of last year and he was the main
person protecting me from myself on
Twitter and he was the one who would say
stay in your lane nobody wants to hear
what you think about politics or San
Francisco or anything other than you
know your area of products and investing
and with him gone I just started
tweeting whatever I felt and thought and
sometimes I got it wrong or it was a
little too emotional but first of all it
was really fun and then second of all I
found I got connected to this whole new
audience of people people who are these
kind of techno optimists I think you
guys probably talked about
it and that just brought me down this
path that eventually I came out two days
before the
election publicly for Trump um and it
was only because that's when I
completely got there and I was trying to
just be completely honest and authentic
with myself and on Twitter at the same
time and my daughters turned to me that
Sunday and they said you're you're going
to vote for Trump we know it and I said
yeah you're probably right and they said
well then you have to go say it on
Twitter and my daughter's like really in
this with me yeah so anyway and then it
was on the front page of the New York
Post on the day of the election that I
was uh this not that I'm such news but
maybe it was just was their news Peg um
that I was coming out for Trump and but
I'll get back to your re question but
what I love about my New York Times
about my New York friends is that they
did not give a f they were all pro comma
and they texted me and they're just like
oh that's kind of funny but it's one
thing I kind of love about New York they
didn't care back to your question on
Reed what I love about Reed was he was
already getting pings from people saying
what's going on with pinkis he's going
off the rails he's becoming a Trumper
you know it's you guys I'm sure have
gone down got a little bit of that too
about shamas in
freeberg yeah so like what's wrong with
him we got to bring him back into the
fold you know he's he's should we lock
him up is he crazy um and so Reed was
already getting these I had a lot of
anxiety about talking to Reed about it
and finally Reed and I got on
FaceTime and he just said I just want to
start by saying I'm team Mark and I said
I'm team Reed
and it gets out a little you know a but
well no Americans can get along even if
they disagree politically about a
candidate it's probably where we need to
get to especially you know now that
Trump's going to be in office in a
couple of days what was it like when for
Biden yeah okay well just to finish the
read part sorry but what what I love
about Reed is that we followed that with
a 4our dinner and he said I never
questioned your principles he said I
know you're a highly principled person
and I just want to understand which
principles it is and I'd like to
convince you to change your mind but
anyway
so hold on one second
so I you said something almost in
passing but I just want to double click
I think part of what Silicon Valley
actually gets wrong is that we don't
embrace the tism and what I mean by that
is everybody we're all a little socially
uncomfortable we awkward I wouldn't say
that we were the coolest people growing
up and there's this virent form of
blockers you called it Chief of Staff I
think that these folks can be very
detrimental which almost represent this
filter between your true self and
everybody else and there is this game
that's played about being a
gatekeeper I do think that executive
assistants are val valuable
administrative assistance are valuable
the reason I can say this is that my EA
went on maternity
leave I had and I experimented with a
chief of staff Etc and now I use Jason
service called Athena and I have a guy
that works with me in the
Philippines and it's about 3,000 a month
and I can honestly tell you this guy is
the single most effective administrative
support I've ever had and what there is
is all these opinions on what I can say
or do and I think that when you look at
a lot of these big companies if you look
at zuck's current transformation or what
you just spoke about there are all these
Interlopers that seem to get in the
middle of you and people's perception of
you I don't know if you have any
comments or reactions to that idea yeah
it's part of where I know you guys have
talked about Zuck coming out as Lisa's
based or his seemingly more authentic
self or sharing more about himself
and I can relate to it because I think
we all go through this this struggle as
you start to be more of a known person
inside your company outside your company
and you have people around you taking
the edges off and I think that we're now
in this time that I think we're having
authenticity is having a moment now
which is great for me because Reed said
to me I I've if you Google me you'll see
that there's lots and lots of bad things
written about me and a lot of it is my
high school quote was some people have
tacked and others tell the truth and
I've always been kind of just committed
to being honest even if it's nuanced and
it's not an easy sound bite and Reed
said to me early on you need to pick
what the easy narrative is or the Press
is going to make it up for you and he
was right and they did or my competitors
did so I think that now with long form
podcasts and there's just more and the
fact that we can kind of directly in a
lot of ways Elon was the first one to
directly defend himself you remember
when well he fired his do you remember
when he fired his whole PR team he fired
all those people there's just like
there's none of that infrastructure
between him and and everybody else but
do you remember when he would be on
Twitter all the time post PayPal trying
to correct the story
and just write long long diet tribes and
then and then when a New York Times
Reporter said something negative about a
Tesla he just went off for weeks about
them and and it seemed a little crazy
and deranged and then you started to see
that it worked like he actually and we
were told don't defend yourself if
something bad is written about you
you're going to prolong the press cycle
you're going to make the journalist
angry and so we've we're now Unshackled
I teach this class at Stanford and I
taught two backtack on Monday and I
looked around and I saw half the plard
said you know she her you know he him
his and I got a little Pang of like oh
do I have to watch one I'm say I'm like
no I don't I'm Unshackled I'm just gonna
this is just me and I'm gonna be Mark
unfiltered and it's the better version
of our so anyway I I'm glad that Zuck
feels like he can be he can present more
of his complete self out there now and I
think we can get into it later but I
have a lot of thoughts on how the
culture is going to kind of move more
towards base
Ask follow-up questions or revisit key timestamps.
The speaker recounts his 'red pill moment' starting in 2013, which led him to question mainstream media narratives, particularly after discovering misrepresentations of Donald Trump's Charlottesville speech. The departure of his chief of staff enabled him to express his unfiltered political views on Twitter, leading him to connect with new audiences and eventually endorse Trump publicly. He highlights a positive interaction with Reed Hoffman, who exemplified respectful disagreement. The speaker advocates for authenticity in public figures, criticizing 'blockers' like chiefs of staff that filter one's true self, and cites Elon Musk as an early adopter of direct public engagement.
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