[MUSIC PLAYING]
ERIC M. RUIZ: Ryan Holiday,
our guest this afternoon,
is the best selling author
of "Trust Me, I'm Lying,"
"The Obstacle Is The
Way," "Ego Is The Enemy,"
and other books about
marketing, culture,
and the human condition.
His work has been translated
into 28 languages, including
Spanish, and has appeared
everywhere from the "Columbia
Journalism Review"
to "Fast Company."
His company, Brass
Check, has advised
companies such as Google,
TASER, and Complex
as well as multi-platinum
musicians and some
of the biggest
authors in the world.
He lives in Austin, Texas.
All right.
RYAN HOLIDAY: All right.
ERIC M. RUIZ: So, Ryan, I've
been a huge fan of your work
and following your career since
the Tim Ferriss stoicism post
days, and something that I
noticed about your latest book
was that it was very
much kept under wraps.
RYAN HOLIDAY: Yeah.
ERIC M. RUIZ: Yeah, was that--
so can you tell us if
that was by design,
and can you tell us more
about your newest release?
RYAN HOLIDAY: Yeah,
so usually you
announce a book
when it comes out,
and you tell people you're
working on it because you
want pre-publicity attention.
With this one, there was a
number of other people circling
around it, and so
I sold it first,
but I didn't want to tell
people that I had sold it
because I wanted them to
think that they had more time.
So we kept it secret
for a long time.
I sold it-- instead of like
going out to an auction
to sell the rights to it, I
sold it to my same publisher
that I usually sell my books to.
And then when I was
interviewing people,
I told people that it was a
book about media, which it is,
but it's also
about other things.
And so yeah, it was sort of
secret, and I think part of it
was just fun.
I mean, it's a book
about conspiracies,
so it was fun to be a
little bit conspiratorial.
And then when we
announced it, we--
when we did announce
it, the book
was already 3/4 of the way
written, so I had a big lead.
I felt comfortable.
And then when we said
when it was coming out,
we put the release date
earlier than it really probably
ever was going to be
just to go, there's
no way you're going
to beat us on it.
I think-- and I heard from--
when it was announced, I heard
from a bunch of other writers
that were like--
they're basically
like, god damn it--
ERIC M. RUIZ: You beat me to it?
RYAN HOLIDAY: You beat me, and
now I'm not going to do it.
So that was sort of the idea.
ERIC M. RUIZ: Nice.
Well done.
RYAN HOLIDAY: Yeah, it worked.
It worked.
ERIC M. RUIZ: So yeah, this
book, this storyline, it's so--
it's crazy.
It seems like
something straight out
of the 19th century, where you
have these crazy characters
from disparate backgrounds,
some of the greatest crossovers
since Marvel's "Infinity War."
RYAN HOLIDAY: Yeah,
I mean, if you made--
if you made up--
so first, I've just the
simple story, which is--
this was a story of the
professional wrestler Hulk
Hogan having sex with
his best friend's wife.
His best friend was legally
named Bubba the Love Sponge,
and then Bubba the Love
Sponge was secretly
recording them having sex.
And then that tape is stolen,
leaked, a website runs it,
and then Hogan
sues the website--
sues Gawker for $100 million and
wins in court many years later,
and Gawker's put
out of business.
That would be weird--
that, in itself, was an insane
story that got headlines
all over the world.
I mean, that was great.
And then to zoom out a few
months later and find that,
actually, an enigmatic
libertarian billionaire
had put the entire set
of events into motion,
and he'd done so because nine
years previous, that website
had outed him as gay.
It's just-- and then to flash
forward and find out that
the same lawyers who are
involved on both sides of this
end up representing and fighting
a case between the President
of the United States, who is
Donald Trump of all people,
and Stormy Daniels
the porn star--
it's just-- I mean, if I was--
we're spit balling this idea,
and I was-- you'd be like--
you would have cut
me off at some point,
like we don't need anymore.
This is already
completely unbelievable.
It's like a choose
your own adventure
one where you pick like the most
ridiculous of all the options
over and over and over
again until it sounds--
it sounds like something
that could not have
possibly happened, let alone--
history is weird.
But I do feel like things
are less weird in the--
part of the reason this
story was such big news
is people don't do
shit like this anymore.
If you heard that Cornelius
Vanderbilt sued a media outlet
for embarrassing him,
you'd be like, OK,
that's what they did back then.
But it's much stranger, I
think, that this happened in--
the verdict came down in 2016.
It's very weird.
ERIC M. RUIZ: And to
follow along that thread,
it seems amongst our peer group
that there was two lines drawn,
where one side of the
sandbox, so to speak,
very much said this a
great example of what
happens when you do
things that aren't right.
RYAN HOLIDAY: Yeah.
ERIC M. RUIZ: And then
the other side of it
was like, wait, actually, a
billionaire just bankrupted
a journalism company.
This is the end of
journalism as we know it.
What president has
this [INAUDIBLE]??
RYAN HOLIDAY: Yeah,
well, it is weird
because there was
this period, and you
can see what people thought
during this two months--
two month period.
You can see basically
up through the trial.
In fact the coverage of
Gawker during the trial
is universally--
almost universally negative.
These people deserve
what's happening to them.
Even from the media itself,
how could they do this?
AJ Daulerio's testimony
is a sort of media crisis
where almost everyone
is uniformly anti-Gawker
at this point.
Then the verdict happens, and
the verdict surprises everyone
in just how enormous it is.
I mean, obviously having
a stolen sex tape of you
run has damages.
Are those damages $140 million?
That's pretty enormous.
But still, people were almost--
there was very--
in this two month
period between the verdict
and when Thiel's involvement
is revealed, the story is
seen as much less ominous
as it is after his unmasking.
So there is a period
where people--
even the "New York
Times--" the co-counsel
of the "New York Times"
has interviewed him
in a "New York Times"
story, and he's
like, there's no precedent here.
He's like, basically,
you just don't
run sex tapes of celebrities
without permission.
It's only when
Thiel's involvement
that suddenly everything--
all the history is revised,
and the entire narrative
shifts, which in some ways,
Thiel should have anticipated.
That he didn't--
I think there was some naiveness
there, or some wishful thinking
about how it would be seen.
He's the-- as soon
as you win, you're
not the underdog anymore, and
so there's that part of it.
But then the idea--
people go like,
he just set this--
I mean, he did nothing that
hasn't been done many times
in the past.
The difference here is that
media outlets don't usually
run stories that open them
up to such enormous damages
judgments, and they
usually settle cases
long before they ever--
media companies
know, basically, you
don't let cases get
in front of a jury.
Because once it gets
in front of a jury--
the jury is not
sitting there thinking
they have this immense
constitutional obligation.
In this case, they
were like, man,
you really screwed over
this Hulk Hogan guy who's
from the town that we live in.
Fuck you.
I think that was
the jury's verdict--
that was what reflected
the jury's verdict.
So I think in a
weird way, I think
the precedent is much less
than media personalities
and academics and stuff want
to make you think there is.
ERIC M. RUIZ: That's fair.
And to kind of follow
along with that,
too, something that I
found really fascinating
was that Gawker--
they have Valleywag, which is
where the article went out,
but then they had
this other outlet
they called Jezebel,
which I believe is still--
might still be running.
RYAN HOLIDAY: Yeah, yeah.
ERIC M. RUIZ: But Jezebel was
very much of the [INAUDIBLE]
protecting female celebrities,
going out of their way
to make sure that things--
that leaks like this
don't happen and get
posted on their site.
So isn't that kind of a
hypocrisy in and of itself?
RYAN HOLIDAY: Well,
to be perfectly fair,
I mean, there's conservative
voices at the "New York Times"
and liberal voices at
the "New York Times"
and different editors
at different times,
different divisions.
They're not going to necessarily
always be a uniform point
of view from any media outlet.
Just like YouTube or Google
has different departments that
do different things,
and sometimes, it
feels like those are in conflict
with each other, when really,
they're just not overlapping.
So it's not--
I don't think you want to
paint it as too hypocritical,
but there is an interesting--
I mean, there's one quote I have
in the book from a Jezebel--
they were like-- the story says,
do not out people who do not
want to be outed, end of story.
And it's like--
and then it's just
like, everyone has
a right to privacy.
And so there is some irony
that the media outlet that
owns Jezebel would then be
destroyed when they egregiously
out one person and
egregiously violate
the privacy of another
person, and that at any point,
instead of apologizing
or settling
the case or some
admission of wrongdoing,
they take it all
the way to a jury,
and then those exact words
are held against them
in that court of law.
ERIC M. RUIZ: Yeah, that
was really interesting,
about how at no point did they
ever just stop and say, wow,
maybe we should just settle.
Maybe we should just apologise.
RYAN HOLIDAY: Well,
they did try to settle.
Much later on, they
tried to settle,
but the right thing to
do, I think strategically,
would have been--
so Hogan files the case in 2012.
He does not-- it's
a $100 million case,
but I don't think
they necessarily
thought they would be
winning $100 million.
It's not until after the
discovery and then as Gawker--
as they go through the
case that their odds get--
so if Gawker had taken it
seriously at the outset,
and maybe they'd--
well, first off, they
get two cease and desist
orders that tell them--
that demand they
take the tape down.
So if they'd taken
it down then, we
wouldn't even be talking here.
So they ignore it, but
then if, at some point
they looked at the actual merits
of the case, and they said,
look, this isn't worth fighting.
Let's pay this guy a half
million dollars to go away,
or we offer him a certain
amount and an apology,
I think Hogan would
have taken it.
But as the case wound on,
Hogan is sort of lost.
He ends up losing his job
because of it, because
of things he did.
He said some racist
things on the same tape.
But Hogan got to this point of
no return, and so it was less--
less and less likely
that he would settle.
I think it's more
that, had Gawker
taken a tack that was,
essentially, look,
we're a media outlet, our
job is to run stories.
We ran this story
because we thought
it was newsworthy at the time.
We believed that we were within
our rights to publish it.
We did not intentionally
hurt anyone.
We've taken the story down.
We've apologized.
We've attempted to settle
this case many times.
I think that would have--
that legal strategy
would have played
much better in that courtroom
than the legal strategy which
they did run, which
was like, first,
we can run anything we want.
Why are we even here?
And then two, we believed
this story was newsworthy,
which is what they claimed.
But then that opened
up Thiel's legal team
to be able to go, OK,
what research did you
do before running this story?
Why was it newsworthy?
Why did you say
in your deposition
that you didn't believe
it was newsworthy?
So they really--
I think in some ways, they did
not get great legal advice,
and they ended up fighting this.
They were-- look,
they were fighting--
they weren't fighting on
first amendment grounds.
They were fighting on a
right to-- they were fighting
a right to privacy
case in Florida,
and they were fighting
the intentional infliction
of emotional distress.
And so this idea of, we've
said before that no one should
be outed, that they
shouldn't be hurt,
made it look very intentional
and very difficult to defend.
ERIC M. RUIZ: So 2007,
they write this article
about Peter Thiel.
RYAN HOLIDAY: Yep.
ERIC M. RUIZ: 2012, they
post the Hulk Hogan video.
So then how did Hulk Hogan
and Peter Thiel link up?
Because I'm assuming
there's a lot
of people that had
vendettas against Gawker.
RYAN HOLIDAY: Yeah,
yeah, obviously, they
weren't friends beforehand.
Actually, I went to a
dinner at Thiel's house,
sort of a victory
dinner, when I was
writing the book, which is in
the hills, and Hogan was there.
This was the first time they'd
ever-- this was in 2000--
early 2017.
It's the first time they'd ever
met or been in the same room
together, so this is
months after the verdict.
So they-- and Hogan
actually did not
know who was backing his case.
He just knew that a wealthy
businessman, or group
of businessmen,
was doing the case,
and that was, in
some ways, I think,
how they were able to keep
it secret for so long.
But what happened was--
so in 2011, Thiel had embarked
on this strategy of, OK,
we think that, in
Gawker's archives,
there are causes of action.
There are articles
they've written
that have crossed some line,
whether it's a copyright
violation.
Maybe they were running photos
they didn't have the rights to.
Maybe they were--
they thought maybe
there'd be something on
the affiliate commissions
they weren't disclosing, that
they were taking an affiliate
cut, or maybe that they had
violated someone's privacy,
any number of violations,
that they would find people
who were willing to let Thiel
back their case against Gawker.
And they really didn't
find anything right away.
They looked, but they
didn't find anything.
And so it's not until October
of 2012 that the tape runs,
and Hogan had actually been
very public about his intention
to sue whoever runs it.
And Gawker was aware
of this as well.
There's like a-- there's a
TMZ headline that's like--
and you can see this all
in the legal documents.
But there's a TMZ headline
that's like, Hogan--
I will sue whoever
runs sex tape.
And then the publicist
at TMZ sends it
to Gawker's tip line, which
goes to all their editors.
So they knew that this
was going to happen,
or they knew that there
was a risk of it happening.
And so he'd been
very public about it,
and then Gawker runs it.
And that's the--
Thiel is, at that point,
laying in wait for something
like that to happen.
So they see the tape when
it runs like everyone else,
and then Charles Harter, who's
the lawyer that was running
the conspiracy, puts a
call into Hogan and says,
hey, do you need any help.
And that sets this in motion.
ERIC M. RUIZ: Got it.
And earlier, when we were
describing the characters
in this book, there was one
that we didn't mention yet,
which is Mr. A, and he's
got-- so two questions there.
The first one is,
could he have--
was Mr. A the only option
for a secret agent name?
RYAN HOLIDAY: No, I mean--
I guess you're right.
It's not the most creative--
it's not Deep Throat or
something cool like that.
But no, I think--
he didn't want his
identity known, and that--
I wouldn't have chosen Mr.
A, but that's the name they--
that I first heard from them.
And so I was like,
OK, we'll use that.
ERIC M. RUIZ: We'll run with it.
And so he was
really the one that
brought this plan to Thiel?
RYAN HOLIDAY: He basically
pitches it like a tech startup.
He's-- he has a dinner with
Thiel in Berlin in April
of 2011.
And they're sitting
there, and Thiel's used
to getting pitched.
And he says, hey, look, I
know you don't like Gawker.
I have this idea.
And I think the
remark-- not just
like is it kind of remarkable
that he pitches this.
I think the remarkable
thing about that meeting
is he actually says I think
it'll take three to five years,
and I think it will cost
roughly $10 million.
And that's almost
exactly what happened,
so he completely called it.
But, yeah, this
26-year-old kid pitches
Peter Thiel on this idea, and
Thiel backs it on the spot.
And it sets in motion
all this stuff that--
the meeting's in 2011.
No one even knows
of Mr. A's existence
until the book came out
in February of 2018.
ERIC M. RUIZ: Yeah, something
like a Facebook post
or something, like a photo.
RYAN HOLIDAY: Well,
no, some people
obviously in Thiel's orbit
knew, and obviously the people
involved in the conspiracy.
Mr. A was the one
interacting with people.
That's how Thiel
kept his distance.
But I'm saying that
his involvement in it
was totally secret until even
the publication of the book.
So I guess it just goes
to show, on the one hand,
secrecy is really important,
but two, this thing that
had been covered by every major
media outlet on the planet
didn't go--
I think what's fascinating is
that it was actually easier
for people to hold onto the
idea that this billionaire was
personally reviewing
legal documents,
than the idea that he might
have paid someone to help him.
So I think it's also
illustrative of just how
little we understand how things
work and how superficial--
how willing we are to
just stop at the surface
and be like oh, OK.
We're like, oh,
Hogan's suing Gawker.
That's what it is, and
then it's like, oh,
Peter Thiel backed it.
OK, that's what it is.
No one was like,
what's the real story,
and that's why this
didn't get out.
ERIC M. RUIZ: And
so in this book,
you had access to Mr. Thiel,
to Nick Denton, Hulk Hogan
as well.
How did that come to be?
How did-- did both of
them reach out to you?
Did Gawker and Thiel's camp
come forward with information,
or did you reach out to them?
RYAN HOLIDAY: Yeah, so
Thiel emailed me first
because he'd read some of the--
I have a media column for the
"Observer," which he had read,
so he likes something.
He just sent me an email.
He said, hey, I
liked your column.
We should-- he said,
next time you're
in New York or San Francisco,
said we should have dinner,
we should talk about the MBTO,
and then in parentheses he
says, Manhattan Based
Terrorist Organization, which
is how he'd always refer
to Gawker, I guess.
So he's already giving me this
glimpse into how it works.
So we ended up
talking, and then--
so I was thinking about
doing a book about it,
and then independently, Nick
Denton reached out to me
because he'd read my more
philosophical writing and--
like that, and we were
talking about that.
And then I basically
was like, hey, look,
I'm talking to Thiel.
Will you talk to me?
And the fact that I was talking
to both of them, I think,
contributed to the--
became a dynamic
where neither of them
necessarily wanted to
disengage because then
it would be lopsided in
favor of their mortal enemy.
ERIC M. RUIZ: Something
that really stood out
from your description of
Thiel in the book was that--
and this is a quote
from the book--
you describe him as,
quote, "as if he is always
in the process of deciding what
he thinks," which is beautiful.
Can you talk more
about that line?
RYAN HOLIDAY: Yeah, I don't know
if it's beautiful necessarily,
but I appreciate that.
When you're talking to
Thiel, it's strange.
He has this tick.
At first, I thought
it was a tick,
and then I realized it was
more-- it was deeper than that.
If you ask him a-- if
you ask me a question,
and then I was just like--
ERIC M. RUIZ: That--
RYAN HOLIDAY: See, you're
getting uncomfortable.
ERIC M. RUIZ: Yeah.
RYAN HOLIDAY: Yeah, because
you're like why am I not--
and so he really just stops
and thinks about everything
before he answers.
And so it was actually weird.
I get uncomfortable
from that myself,
and so I'd always be like, oh,
did I ask the wrong question?
Should I ask a
different question?
And then by the time I'd
start the second question,
he was just getting around
to his first answer,
and so then that it was
this sort of comedy of,
you go this way,
I'll go this way.
But he's very--
I think he's a
very deep thinker.
He's a very considerate thinker.
Not necessarily considerate
to other people,
but I mean, he really considers
and deliberates about his work.
There's not much
sloppiness there.
He's not willing-- he's not
willing to just pull something
out of his ass.
He's really going
to think about it.
And then what I think is
interesting is that he has--
he does this every time,
even if it's something
he's talked about before.
So he sort of--
ERIC M. RUIZ: Like he's
willing to change his opinion?
RYAN HOLIDAY: Well,
no, it's like he's--
instead of having
this shortcut, like
I already have an opinion
about x, so that's my opinion.
If you ask him, I think he
almost goes to first principles
and thinks about it
from scratch again.
So that's why there's
the delay, like he's not
utilizing the shortcuts
that most of us are doing.
And so I think this does--
this is a much more--
this is a much less sloppy
way to think and act and talk.
So I think that's
where, I think,
some of these deeply
counterintuitive,
if not occasionally
strange, insights come from,
is that he's not
just winging it.
ERIC M. RUIZ: So
this is very much
a new type of book for you, and
I saw somewhere, maybe Reddit,
maybe your website,
that you read something
like 25,000 pages
of legal documents?
RYAN HOLIDAY: Yeah.
ERIC M. RUIZ: Wow.
RYAN HOLIDAY: A lot.
ERIC M. RUIZ: So tell
us, then-- can you
tell us about the process of
writing a new type of book?
What was that like?
RYAN HOLIDAY: Well,
my other books,
they're all about basically
dead-- they're either about me,
or they're about dead people,
so that's much easier.
And most of my books
are not chronological,
so I'm just telling different
stories here or there of stuff
that's interesting to me.
This was harder because
a set of things happened,
and they happened
in a specific order,
and then I had to tell them
more or less in that order.
So I had to first just
figure out what happened.
So obviously, I
haven't done a lot
of interviews for my previous
books, so that was new.
I had to read a lot of legal
documents, which was definitely
new.
There was 17 binders,
25,000 pages,
and that was after we got rid of
all the unnecessary pages, all
the redundant pages or
duplicates or whatever.
Yes, so I had to read it,
so yeah, it was different.
I just had to come up with
a different methodology
for writing.
I had to do much more
outlining, organization.
It was just different.
But I think it was--
I enjoyed the challenge
of it, for sure.
ERIC M. RUIZ: And it's--
got it.
And I read it, I think
it was last week,
that the book's been optioned.
RYAN HOLIDAY: It has, yeah.
ERIC M. RUIZ: There's a movie.
RYAN HOLIDAY: A
movie or a TV show.
I don't know.
My other books have
been optioned before,
and sometimes, they happen.
Sometimes, they don't.
But a bunch of really big
people are interested in it,
so we'll see.
I mean, I hope it happens.
I mean, you could not invent
a more cinematic series
of events.
I mean, like it was said, it
feels like fiction or history.
I mean, it's
basically the "Count
of Monte Cristo" in modern days
is how I've been describing it.
ERIC M. RUIZ: In Silicon
Valley and in Florida.
RYAN HOLIDAY: Yes.
Yeah, I mean, it's
a crazy story.
So it would be great--
it sort of reminds me of the
People versus OJ Simpson,
a contained legal drama.
So yeah, I hope it'll happen.
We'll see.
ERIC M. RUIZ: Nice.
Well, wish you the
best of luck with that.
And to kind of switch
tracks for a little bit,
you read a lot about
strategy, and it's
a theme in your other books.
It's also the underlying
theme in this book as well.
And to kind of start
off with, a quote that--
I think it was from a
master chess player.
It said that, to begin with,
you must study the end.
You don't want to
be the first to act.
You want to be the
last man standing.
RYAN HOLIDAY: Yeah.
ERIC M. RUIZ: Can you talk
about that a little bit?
RYAN HOLIDAY: So that's one of
Thiel's favorite quotes, which
is why it's in the book, and
it's from Raul Capablanca.
And its point is that you
have to know where you're
trying to end up, so then you
can evaluate your decisions
with that end in mind.
What oftentimes
happens, we're like,
oh, we generally want
to go in a direction,
and then we make decisions that
take us, because the decisions
compound on each other,
that take us in a completely
different direction.
So I think, in this
case, for instance,
Thiel wasn't thinking, oh, I
would like to just hurt Gawker.
I think he was like, I want
Gawker to not exist at the end,
which is somewhat ominous and
can be scary depending on where
he's--
but he had a very
clear end in mind,
which I think is the
strategic imperative.
You have to-- what are
we trying to accomplish?
What does success look like?
And if you don't have
that, how can you properly
evaluate opportunities and
decisions as they come up?
You can't.
You're looking too short term.
And so the decisions--
the logic that you're
doing might make sense
in those individual decisions,
but they get you further.
So the way this would
apply in ordinary life
would be like, if
you don't know what
you want to do, if you don't
know where you want to end up,
if you don't know what
happiness or success looks like,
you end up--
you're offered a
promotion, but it
requires you to move to a place
you don't want to live in.
Or you end up getting
paid more money,
but now you have to work more
hours, so you're less happy.
Or there's this opportunity to
do this thing in your career,
but it's going to inflict
a certain amount of stress
or damage that your
marriage cannot sustain.
And so people end up
making short term decisions
where it's like, of course,
if someone offered you
x amount of dollars
you should accept it,
or who wouldn't want
to live in this city.
Well, maybe the answer is you.
And so we go, oh,
I should do this,
or I have to do this
because it makes
so much overwhelming sense
in the context of these two
options.
But what you're not
seeing is, over here, you
have your giant pool
of options, and this
is shrinking as a result
of one decision or another.
And so for me, I love writing,
and then I'm pretty good at it.
And it's what makes me--
I'm happy when I'm writing.
But then I get offered all sorts
of other opportunities in life
that can shrink or expand the
amount of time that I have
to do writing, and so if I
don't know what the end--
what I'm working towards, what
I want my life to look like,
then I'm going to be--
of course, I should go here,
or of course, I should do this,
or of course, I should hop on
the phone with this person.
But it's actually-- it's a
short term success that's
causing a long term failure.
ERIC M. RUIZ: And that's one
I think about quite a bit.
I think, in our peer group--
I know we're both--
you're, what, from '87?
RYAN HOLIDAY: Yeah.
ERIC M. RUIZ: We're Reagan
babies. '87 as well.
RYAN HOLIDAY: OK.
ERIC M. RUIZ: And it
seems to me that my group
of friends and my
colleagues kind of fall
into one of two camps.
It's either, I have
too many options,
and I don't know
which one to take.
I don't know what
to optimize for.
Or I don't know what I want
to do, I have no options,
and I'm just stuck here.
And I feel like there's
this balance of,
you want to not be so focused
that you only have one--
one destination,
but you also don't
want to be so broad that
everything is now an option
RYAN HOLIDAY: Yeah,
those are two sides
of the same coin in the sense
that if you don't know what you
want to do, it looks like
you have less opportunities
than you actually do.
If you know-- if you know
clearly here's what I want
to do, there's lots of
little-- you might not be--
you might not have some world
changing opportunity right
in front of you, but
you have little things
you can do that might
put you on the path
to get where you want to go.
And then, yeah, if you
have too many options,
and you don't know
what you want to do,
it's obviously a
champagne problem.
Many people would
kill to be there.
But how-- you're not
going to optimize or make
the right decision in
that set of circumstances
because you don't know
which option is better
than the other options, and
there's always a better option,
I would think.
So I think this is also
true as a business.
If you don't know what--
if you don't know
what your business is
and what your business
does, how do you
know which opportunities
are in your wheel house
and which ones are
outside your wheel house.
ERIC M. RUIZ: And then
how do you balance
this idea of being happy
with what life has given you,
or the things that
you've worked for,
and then going
for the next step?
How do you know when
an impulse is ambition,
or if it's going to come at a
cost of more fame, more glory?
Which is-- in a way,
those are good things,
but what's the cost to that?
RYAN HOLIDAY: I
mean, that's-- yeah,
that's the million
dollar question.
How do you know?
I don't have-- like here's the
answer to all life's problems
in one sentence.
I wish.
But I do think you--
here's how I do it--
I go what do I want
my day to look like?
I think about it in
terms of one day--
one day, like right now?
What do I want one day to
look like in five years,
in 10 years?
What do I want my
life to look like?
And then I try to make decisions
that get me to that life.
So I had a conversation
with someone--
I had a conversation
with someone
pretty early on in my career.
I'd been successful
early, and I was
thinking about doing something.
And he said, what do
you do with your money?
And I was like,
what do you mean?
And he's like, what do you do?
Do you buy boats, or do save it?
Or do you give it
all to charity?
What do you do with your money?
And I was like, I don't
really do anything with it.
It just sits in a bank account.
I live a relatively
cheap lifestyle,
and I have what I want to
have, so I don't need it.
And he was like, so why
are you doing this thing?
Why are you doing this
thing that you don't really
like to get more of
a thing that you're
saying you don't really need?
And so that's a
long way of saying
that, I realize that having more
or less money within a range--
a normal-- not a
billionaire range or even--
just a normal range--
was not affecting my life in
any positive or negative way.
So it was like,
oh, OK, what do I--
then what do-- what does
positively or negatively affect
my life?
I fucking hate
going to meetings.
I hate living in certain
places that I've lived.
I hate getting on the
phone for no reason.
So it's like, oh, OK,
so I'm going to make--
the decisions I should
make should not be like,
is this going to
make a lot of money,
or is this going to get me
a lot of media attention?
But is this thing going to
increase the amount of phone
calls that I have to be on, or
decrease the amount of phone
calls I want to live on?
Or is this going to free me up
to live where I want to live,
or is it going to force me to
spend a lot of time in a place
that I don't want to be?
And so that is kind of how
I evaluate those decisions.
ERIC M. RUIZ: Got it.
Another quote that
really stuck out to me
was from BH Liddell Hart--
in strategy, the
longest way around
is often the shortest
way home, which is,
in a way, kind of changed
my life in a good way, where
it's like, ah!
RYAN HOLIDAY: What
does it mean to you?
ERIC M. RUIZ: To me,
I think it's that--
it's that idea that you have
to start from the end and work
backwards, where you have to
have that objective in mind
and know that it's not going
to be there immediately.
For example, let's say that I
want to write for a major blog.
Well, it's going to be very
hard to write for, let's say,
Fast Company.
RYAN HOLIDAY: Yeah.
ERIC M. RUIZ: But if I can write
for a few lesser known blogs
or maybe some very specific
ones to build my credibility,
it's going to take longer
as opposed to me just
pitching the guy
at Fast Company,
but if I can prove myself
in these three blogs,
I can then package that,
give myself some credibility,
and then go talk to the
guys at Fast Company.
RYAN HOLIDAY: Or you
could do all that,
and then you might
get an incoming email
from them asking you--
ERIC M. RUIZ: Exactly.
RYAN HOLIDAY: I think that's
what the quote means, yeah.
Oftentimes, we try-- and I think
this ties into the conspiracy
thing, or what happened in
this specific conspiracy, which
is that we think you should
do the straight forward
or the obvious thing.
That's like, oh, Thiel
says they outed me,
so I think the more reactionary
person in that situation
will go, I'm going
to sue you for that.
You shouldn't be
able to do that.
Well, the law is pretty clear.
I mean, there's some debate--
the law is pretty
clear that it's
not illegal to out someone.
It might be in bad taste.
It might not be cool.
It might cause consequences
for the-- but there's not--
even if you were to win, one,
the verdict would probably not
be very large, and two, I'm not
sure it would send that much.
It might almost send
the opposite message
that Thiel would want to say.
You essentially
are-- in that case,
you would be arguing
that, you outed me as gay,
and it's bad to be gay, so
by making me see-- being
seen as gay, you've hurt me.
That's not a strong
position, so he waits.
I mean, he waits for four years
until 2011 to have the meeting,
and then he waits until
another-- so a total
of five years, basically,
until he filed a case.
The Hulk Hogan-- the running
an illicitly recorded sex
tape that the person
had loudly said,
do not run that-- cease and
desists had been ignored,
et cetera, is a
much stronger case.
So that's the long way home.
That's the long way around.
He waited five years
for this opportunity.
But you could argue
that, from the minute
they filed that case, they
were on a track to win.
Do you know what I mean?
But had he filed a case
in 2007 or a weaker case
in 2008 or 2009, it might have
gone to trial much faster,
but what it would
have accomplished
would have been far less.
ERIC M. RUIZ: Got it, yeah.
It almost seems like,
again, going back
to our peer group, our
colleagues, our coworkers,
our friends.
It seems one of the
recurring themes
is this want to immediately
dart towards the finish line,
so immediately get to
wherever it is we're going.
And I think that one of
the downsides to that
is, and I think seemed
[INAUDIBLE] alluded to it,
is that you cut yourself off
from serendipity, for one.
And you also short
change and try
to hack a system that eventually
might hurt you down the line,
where it's like,
oh, that's Eric.
That's the kid that tried
to do this the wrong way.
I don't want to work with him.
RYAN HOLIDAY: Sure.
I mean, look, I'm
all for shortcuts
where you're cutting off
unnecessary things that you
don't need to do.
But yeah, I think
generally, doing it right
is better than doing it fast.
ERIC M. RUIZ: Yeah.
RYAN HOLIDAY: And
it's like whatever
the first thing you
think you should do
is probably not the right thing.
But I do-- not to stereotype
millennials, but I do--
I think we're-- having grown
up with the internet the way
we've grown up with it,
there is this belief that,
because everything is
at your fingertips,
because things can
magically go viral,
because it's so easy to gather
large amounts of people,
that that is--
that's the hammer that
we have, so everything
looks like a nail.
And those tools are a solution
to a very small subset
of problems.
Again, you can agree or
disagree with Thiel's criticism
of Gawker and the
outcome that he wanted,
but I'm not sure there
was any other way
to accomplish what he
wanted to accomplish.
So Denton said to me, if
Thiel's a libertarian,
why didn't he meet
speech with speech?
Why didn't he write
an op ed about Gawker?
Why didn't he start
a rival media outlet?
Why didn't he create a
public relations campaign?
And the reason he
didn't do those things
is that they
wouldn't have worked.
They wouldn't have
destroyed Gawker.
He was trying to destroy Gawker.
That was the thing he felt
needed to be accomplished.
Again, agree or disagree,
that's the fact--
that is the strategic
objective, and he
was willing to be patient
and creative enough
to find the strategy that
achieved that objective.
Meanwhile, I think we're
changing our Facebook photos
and things that--
think that's going to
intimidate the NRA or something.
ERIC M. RUIZ: But
the hashtags, bro!
RYAN HOLIDAY: Right.
No, we think we're--
look, a hashtag-- first
off, I'm not actually sure
there's that many
examples of viral videos
or hashtags or
social media activism
solving that many problems.
There is the AOS challenge.
That seemed like
it actually worked.
I wouldn't have thought it
would work, but that worked.
But very few-- that
is not something
that's infinitely replicable.
Power is somewhat
timeless in how it works,
and power is typically
required to fight power.
And I think we've--
you don't solve every
problem by marching.
ERIC M. RUIZ: I would
agree with that.
And on that note, I want to
leave some time for some FAQs
from--
QAs from you guys.
So without further
ado, any questions?
Yes, [INAUDIBLE]?
RYAN HOLIDAY: Do we have to
throw this weird microphone?
ERIC M. RUIZ: We do.
Would you like to do the honors?
RYAN HOLIDAY: No, you can do it.
ERIC M. RUIZ: No pressure.
Yes, my Tom Brady impersonation.
RYAN HOLIDAY: That
was brilliant.
ERIC M. RUIZ: Brett Favre.
AUDIENCE: Thanks very
much for coming today.
RYAN HOLIDAY: Of course.
AUDIENCE: It was
really interesting,
and I'm looking forward
to reading the book.
I was wondering, and you started
to touch on it a little bit,
about the meth addicted
ferret attention
span of people on the internet.
I feel like that's
progressively gotten worse.
RYAN HOLIDAY: Yeah.
AUDIENCE: And I was
wondering if you thought
that maybe that kind of
facilitates conspiracies
like this one to go
undetected for a long time
because, basically, everyone
put it out of their heads
that Peter Thiel had been
outed, and that was it.
They were on to the next
thing, and so there's probably
a lot more things
like this going on
that we don't know about
because everyone's looking over
there now.
RYAN HOLIDAY:
Well, look, I mean,
you could argue, depending
on what you think happened
in the 2016 election, whether
there was Russian collusion
or intrusion or
not, the truth is
we were up in arms
on social media
about a lot of shit
that didn't matter--
tweets-- as opposed to what was
happening behind the scenes,
what was really going on.
So I think you're totally right.
I would say two things
facilitate the conspiracy.
So one is that we don't
believe these things happen.
We sort of have this simplistic
understanding of the world.
We think everyone's friends,
everything's awesome,
and we don't realize
that people have agendas,
and they're trying to do things.
So that's-- there's a quote
from one of the Gawker writers--
it's in the book.
It's also in the documentary--
where he goes, we
scarcely could have
believed something so
vindictive and conspiratorial
could have happened.
Well, it's like, that's
exactly why it happened.
You literally couldn't
believe it could happen,
so you didn't see the somewhat
obvious signs in front of you,
so that's part of it.
And then yeah, as
the general public
follows titillating
story to story,
gets distracted by things,
is outraged all the time,
in some ways, this makes
it easier for people
to either get away with things.
Thiel was saying that, at
first, he was very nervous
that people would catch him.
And he was convinced
they would get caught,
and then he realized that no
one was even looking or thinking
about it at all, and
that, in some ways,
that was almost more alarming.
AUDIENCE: Yeah, you could argue
that the current administration
is taking advantage of the fact
that you don't remember what
happened last week because
five other things have happened
this week that you've already
put at the top of your brain
stack.
RYAN HOLIDAY:
Yeah, I think we're
lucky that the chaos
is probably more
of a byproduct of
the incompetence than
of Machiavellian mastery.
But yes, certainly,
whatever they are doing,
the fact that we're exhausted
from being outraged all
the time is-- makes--
the resistance is mostly
outrage resistance
as opposed to well organized,
established resistance
in that more traditional sense.
AUDIENCE: Right.
ERIC M. RUIZ:
Question over here?
AUDIENCE: Oh, right by me?
AUDIENCE: No, he was up first.
AUDIENCE: OK.
AUDIENCE: Thanks so much.
RYAN HOLIDAY: Of course.
AUDIENCE: Yeah, I've
read a few or your books,
and I enjoy them.
If you had to pick one
feature on social media
that you think is causing
a pernicious behavioral
incentive, which
feature would that be?
And I guess you can
eliminate that feature.
What feature would that be?
RYAN HOLIDAY: Well, I think
one of the more pernicious
and subtle ones was the 140
character limit on Twitter,
and I think Twitter's
over-representation--
media is on Twitter.
Normal people don't spend that
much time on Twitter anymore,
but reporters spend all
their time on Twitter.
And so I think there's
been this effect of--
you see these smart people
who write long form writing
for a living competing
with each other
to reduce complicated issues
to the shortest, snarkiest,
least nuanced version
of whatever it is.
It's like, you put the
hashtag section on Twitter,
and it's like you
click on it, and it's
the same top 100
journalists in America
immediately
responding and trying
to encapsulate this complicated
thing with as little nuance as
possible.
And I think that's very bad.
Obviously, the expansion
to 280 characters
is better, but probably still--
it's crazy to think that
the reason all of that--
the faux certainty
and simplification
and toxic culture of Twitter
just comes from the fact
that, when they launched, that
was how many characters you
could send in a text message.
That's totally insane to me, and
then it took so long for them
to expand it.
And I don't know what
they were worried about,
but it hasn't changed--
it made only a marginal--
it's definitely improved
the site, I think.
But that they didn't do that in
2010, I think, is a travesty,
and we're still dealing with
the consequences of that.
AUDIENCE: Indeed.
AUDIENCE: Hi, there.
Can you point to any
media or political event
since the Gawker
decision that you
think might have
turned out differently
had this case not been
decided the way that it was?
How has it impacted us?
RYAN HOLIDAY: I don't think so.
Well, OK, so on the
one hand, simple answer
would be, no, I don't think so.
More complicated answer--
Thiel and the people
around him told me
that what he learned in
that Florida courtroom--
he wasn't there.
But what he saw and how
this thing developed
was part of what gave
him both the confidence
and the insight to back
Trump in the election.
So in that sense, yes.
So I don't think
it's the precedent
of the verdict legally,
but more like the lessons
that were learned there.
And then I mean,
you could also argue
that Gamergate, which is a
movement loosely connected
to what happened here and
is very much anti-Gawker
becomes the alt-right,
which becomes this sort
of toxic force in our culture.
So I think, indirectly, yes.
Directly, no.
AUDIENCE: So is that something
we should be happy about,
then, that it hasn't
had a chilling effect
on media outlets in some way?
RYAN HOLIDAY: Well,
I mean, it's weird
because since 2016,
at least in terms
of traditional
journalism, you can
argue we're living in a golden
age of investigative reporting.
I mean, the Harvey
Weinstein stuff,
the entire MeToo movement--
this all-- I mean, the
traditional media is doing
a spec--
in some ways, I think they're
doing a terrible job reporting
on Trump because they get caught
up in things that don't really
matter.
But they're also
doing a fantastic job
of just nuts and bolts
reporting on what's happening.
So I mean, I don't think
there's been a chilling effect.
I think the irony is Gawker and
this breed of publish first,
verify later, rumors are just
as valid a form of journalism
as triple fact checked
news articles--
if anything, that contributed
to the decline in the public's
trust in the media, and
that maybe over time,
we can come out of
that on the other side.
But I don't think it's
had the effect that some
of the more histrionic critics
have tried to say that it has.
Can you think of an example?
I'd be curious.
AUDIENCE: Certainly not
off the top my head.
I kind of agree
with the golden age
of investigative journalism.
But I was also
wondering a little bit,
is that perhaps because Gawker
had this salacious reputation,
and if it had been
the "New York Times"
or some other reputable
media company,
that the jury might not have
been so willing to slap them
with such a huge penalty?
RYAN HOLIDAY: Well,
with the lawyers who
represented Hogan in Florida--
not Charles [INAUDIBLE],, but
the lawyers who represented him
in Florida who did actually most
of the arguments in the trial--
they represented Sarah
Palin in a lawsuit
that she did file against
the "New York Times."
It was a "Times" story.
They made a mistake.
They said that
she'd put a target--
they implied that
she'd said that guy
that had attempted to
assassinate Gabby Giffords
was incited by Sarah
Palin, which wasn't true.
And she sued the
"New York Times,"
but it was tossed out of court.
So I don't think Thiel
could have sued and beaten
the "New York Times."
One, I don't think they
would have handled it legally
the same way.
I think they would
have done a better job.
But two, I don't think he ever
would have had the opportunity
to do so because I don't
think they ever would
have run a story like this.
AUDIENCE: This conversation
is really interesting
because it's actually causing
me to reframe my own opinions
on the case because
before, I had thought
it was this really sad day for
our First Amendment rights,
and now I'm thinking maybe
this is sort of capitalism
at its finest,
where we're calling
the herd of media outlets
that maybe should have never
existed.
RYAN HOLIDAY: So there was some
argument about the chilling
effect.
They've called it
the Gawker Effect,
and for instance, there
was a story about R. Kelly
that a reporter in Chicago
tried to publish, that he--
the same sort of
R. Kelly stories
that have gone on
for a long time.
And a couple of outlets
passed on publishing it,
and then Buzzfeed published it.
And so there was some--
oh, they didn't
run it because they
were afraid-- the other outlets
didn't run it because they
were afraid of being sued.
But in the end, an
outlet did run it,
and they haven't
been sued for it.
So I mean, I don't
think a chill--
a chilling effect
sounds very ominous,
but if a chilling
effect is properly
defined as the media pausing
briefly before publishing
an article and making sure
that their T's are crossed
and their I's are
dotted, provided
that they do run
legitimate stories
that pass legal muster on
the other side of that test,
I'm not sure that's
a bad thing either.
And perhaps it's a bad thing
that it took this lawsuit
to get people to go, oh,
let's think about what--
let's think about
it before we run
videos that show up in an
anonymous brown envelope
from an unnamed source.
You know what I mean?
It could end badly.
AUDIENCE: Yeah, so I'm coming at
this from a strange perspective
because I've been at
Google for a year,
but before that, I did six
years working at Gawker media.
[LAUGHING]
Yeah.
ERIC M. RUIZ: Plot twist.
AUDIENCE: I've seen
some shit, guys.
I've seen some shit.
RYAN HOLIDAY: I'm sure you have.
What did you-- what
did you do there?
AUDIENCE: I ran film
partnerships here in LA.
RYAN HOLIDAY: Yeah.
AUDIENCE: Yeah.
I knew Nick Denton pretty well.
RYAN HOLIDAY: Sure.
AUDIENCE: But I had--
I have a bunch of questions.
RYAN HOLIDAY: Go for it.
AUDIENCE: To the point you just
made, though, don't you feel--
this is to everybody--
that there are a lot of-- there
potentially could be a lot
of stories that now news sources
are holding back that would
make powerful people
afraid for fear of--
so we don't really
know the impact
because people could be
holding these stories back
that could have legal
ramifications, which is--
RYAN HOLIDAY: No, it's true.
Look, Gawker's-- as you
know, Gawker sort of--
Nick would say that
Gawker's ideal story was
the kind of story that
two journalists would
gossip about at a
bar, the story that--
the real story that they
hadn't been able to run.
And that sounds great
in theory, but there
could be a lot of
reasons why they're not
able to run that story.
It could be that it's not true.
It could be that
they haven't been
able to prove it yet, that they
haven't done enough work on it.
There could be a lot of reasons.
And so two journalists
gossiping at a bar
that a big Silicon Valley
investor is semi openly gay,
is fine for two
journalists to gossip about
because it's two people.
That's what gossip is.
But when you publish it in
front of potentially millions
of people, then it
gets more complicated.
Do you know what I mean?
It gets more complicated.
Is it the right thing to do?
What is the news--
what is the news
value of this story?
Do the costs outweigh--
so I do think, Gawker's
instinct was always,
as you know, to publish.
Publish first and think
about consequences second,
and that is why they were
early to the Louis CK story.
They were early to a number--
the Bill Cosby story.
They were-- they got the
story of Rob Ford, the Toronto
mayor who was apparently
a crack addict.
They were early to
a lot of stories,
and they should be
commended for that.
Part of the reason
those stories didn't
have an enormous amount
of impact at the time
is because people also knew
that Gawker's standard for what
they ran was not the
same as other outlets.
AUDIENCE: Yeah.
I mean, Nick's
theory on the stuff
that other places wouldn't
publish is I worked there.
But I also think they did some
indefensible things, so yeah.
RYAN HOLIDAY: It's
complicated, and in a way,
I respect that Nick--
I think Nick is as--
we talked a lot
about Peter, but I
think Nick is as
brilliant and as creative
and as sort of singularly unique
as an individual as Thiel is.
And in a way, that's probably
why they ended up in conflict
with each other.
AUDIENCE: Totally.
RYAN HOLIDAY: And
so in some ways,
I very much respect that
was Denton's vision.
Denton's vision
was that the world
would be better if those stories
that people were gossiping
about would be published.
And you quoted [INAUDIBLE],,
he had real skin in the game.
He didn't just say
this in theory.
He built a whole
company around it.
It reached billions of people.
He fought for it.
He also made the calculation
rightly, up until this case,
that people would get
mad about Gawker stories,
but would rarely do
anything about it.
I think Denton had a very
high tolerance for being sued,
and he was-- that's why he was
willing to fight this case.
And had Thiel not been
backing Hogan in secret,
Hogan probably would have lost.
So Thiel-- so Denton made
the right calculation
given the facts that he had.
He just missed a
very important fact,
which is that several
years previous,
he picked a fight with
probably the wrong person.
AUDIENCE: Yeah, yeah, yeah.
So I guess my other question
why I wanted this was--
so you spent so much
time with all of this.
Where do you personally land
when it comes to the two posts
the question--
the outing and the sex tape?
Do you-- when it comes to,
did they have a constitutional
right to post it, and did
they have an ethical--
what are the ethics?
RYAN HOLIDAY: Yeah, so I
think, constitutionally, you
have the right to
out someone, just
in the way that you would have
the right to say that someone
is having an affair.
A pseudo-- Thiel was not a
completely private individual.
I mean, he'd sold a company
for a billion dollars to eBay.
I don't know the sexuality
of the other early Facebook
investors or really any of
the early Paypal investors,
but I think he would pass the
public figure test enough.
And I feel like it shouldn't
be seen as a bad thing
to be seen as gay, so although
he might think it's secret,
I don't think it was
illegal by any means.
I there was an
ethical consideration
that I would probably
disagree with Denton on.
But I'm also not gay, and
I haven't lived that life,
so I don't have super
strong opinions there.
I think the Hogan tape--
the First Amendment
is very expansive.
Celebrities give up a good
chunk of their privacy
by nature of being
public individuals who
benefit from publicity, but
there is a line somewhere.
If Jennifer Aniston
was in a changing room,
and someone had put a hidden
camera there and films her
and then leaked it
to TMZ, does TMZ
have the right to publish
that because she's
a public individual
because she's done
nude scenes in movies before?
I mean, of course not.
No one-- does the media have
the right to the Erin Andrews
footage?
I would say absolutely not.
So I feel like there
is a line somewhere,
and I think we can safely, and
without endangering our right
to free speech, say that
the line more or less ends
at private individuals
having sex--
any individual having
sex in the privacy
of a bedroom in a private home.
Where it gets
interesting, for instance,
is if there was video footage
of Donald Trump and Stormy
Daniels--
does the media have
the right to that?
Or if there were pictures
from the Bill Clinton-Monica
Lewinsky scandal--
is that right?
It does get-- there's not
a super right line where
I'd confidently say everything,
but I would say this tape,
I think the jury
made the right call.
$140 million may be too
much, but it shouldn't have--
I think I shouldn't have run it.
AUDIENCE: I waffle myself,
so I just was curious.
RYAN HOLIDAY: Yeah.
ERIC M. RUIZ: Awesome.
Well, I think we're--
yeah, we're close on time.
So, guys, thank you so
much for coming out,
and I think we have a couple
of books still available,
so don't be shy.
Come up and grab them.
Ryan, you can sign or
give high-fives or both.
RYAN HOLIDAY: Alright.
ERIC M. RUIZ: But,
guys, thank you.
RYAN HOLIDAY: Thanks.
ERIC M. RUIZ: Thank you, Ryan.
RYAN HOLIDAY: Yeah.
[APPLAUSE]
