2. About the Author
• Ryan Holiday is a writer and media strategist.
• Dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power.
• Made a successful marketing career at American Apparel.
• Founded Brass Check, a creative agency which had clients like Google, TASER, and Complex, as well
as many prominent bestselling authors like Neil Strauss, Tony Robbins and Tim Ferriss.
• Ryan is the author of ten books, including The Obstacle Is the Way, Ego Is the Enemy and Stillness
is the Key which have sold more than 2 million copies in thirty languages around the world.
• The author spends much of his time on a ranch outside Austin, Texas, writing and working in
between raising cattle, donkeys and goats.
Interesting fact about Ryan
Ryan wrote letters encouraging his father not to vote for Donald Trump in 2016 and 2020.Despite his
public opposition to Trump's 2016 Presidential campaign, Holiday was offered a communications
director position within the Trump administration, which he did not accept. However, he supported
Joe Biden in the 2020 United States presidential election.
3. The book is
Not a love story
Not a motivational story
Nor a biography
It’s a true story of revenge
4. The
Characters
Terry Eugene Bollea
“Hulk Hogan”
Charles Harder
Peter Thiel
Nick Denton
A.J. Daulerio
Heather Clem &
Bubba the Love
Sponge
• Entrepreneur
• Founder of PayPal
• First investor of
Facebook
• The mastermind
behind Conspiracy
• Wrestler
• TV Personality
• Gawker leaked
his tape with
heather clem.
• An American lawyer
• Fought Bollea vs.
Gawker case.
• Referred as “The
Gawker Slayer”
• Entrepreneur
• Founder of
Gawker Media
• Journalist and
Blogger
• American writer
and blogger
• Editor at Gawker
and Deadspin
• Man behind
Gawker’s fall
• Model and
American
Radio
Personality
5. “A conspiracy without any coconspirators is
not a conspiracy. It’s just a crime. This is also basic legal principle. If you
kill someone by yourself, in the heat of the moment, it’s murder.
If you meticulously plan it with someone else beforehand, that's
conspiracy.”
-Niccolò Machiavelli
6. INTRODUCTION
Have you ever had your personal information leaked online? whether or not you've experienced this
firsthand, human beings have always been afraid of gossip. we worry about someone seeing us with
this person or at that place, we worry about what we've said after we've had one too many glasses of
wine, we worry that people will talk but with the advent of the Internet our fears have gotten even
scarier, and the threat of exposure is now more realistic than ever. Unfortunately, Peter Thiel has lived
this nightmare that we dread. He knows what it's like to wake up one day and discover that your most
personal secrets have been outed to the world. his is the story of how he chose to fight back
7. Chapter 1 – Peter’s privacy was violated
• Peter Thiel is gay ,who cares right? But it can sometimes come with some unfortunate consequences.
• It is not OK for someone to out another person or share their story without their permission but that's
what happened to Peter Thiel.
• One morning in 2007 Peter woke up to see a blog post published by Gawker media entitled “Peter
Thiel is totally gay”.
• Peter was the founder of PayPal and as the article itself states “the clubby ranks of VC's are mostly
straight white and male they instinctively prefer entrepreneurs who remind them of themselves at
best”
• The blog that published this article was called “Valleywag “
• Valleywag is controlled by its parent company Gawker media.
• Gawker generates gossip for its readers to gawk at, in fact its founder Nick Denton was so interested in
gossip that he had a habit of deliberately leaking the secrets of public figures just to create hype.
• He accomplished this by employing a team of snarky bloggers who've lived to find dirt on celebrities.
• Individuals enjoyed his expose so much that by 2005 he could boast $120,000 in monthly revenue
alone and by 2012 the figure soared to a whopping $40 million.
8. Chapter 2 - Does controversy makes for bad journalism
• Generally, the answer to that question is No. A skillful journalist can easily start a conversation that
encourages people to weigh in on controversial issues without going too far.
• Denton had a vested interest in actively causing damage he frequently pushed ethical boundaries to dig
up dirt on his latest victims.
• Although the world has become a much more inclusive place as of 2022. It wasn't the case in 2007as
many states didn't even recognize gay marriage or civil partnerships at the time.
• In addition to the invasion of his privacy and the potential repercussions of his professional life, Thiel had
also been outed in an era that was still overtly hostile towards gay people.
• Gawker posted another article, publishing clandestine snapshots of Thiel and his boyfriend along with
salacious rumors about Thiel's sex life.
• Although Thiel might have felt like it was a personal attack on him, the truth is that this was standard
behavior for Denton and his team of bloggers.
• Despite it might have been nothing more than business to Gawker, the problem was that their business
was comprised of other people's lives.
• Gawker was proud of leaking stolen material like illegally obtained celebrity sex tapes and Peter started
referring to them as the (MBTO) i.e., Manhattan based terrorist organization.
9. Chapter-3 How to pick a fight with a journalist
• An old saying about how the pin is mightier than the sword, well Thiel knew how true that was,which
meant he faced dilemma in looking for a unique way to fight Gawker.
• How do you bring down someone who has the full power of the media behind them? It took Thiel four
years to figure that out and he spent the period between 2008 and 2011 plotting his revenge.
• Thiel realized that he couldn't even try and shame Gawker into withdrawing their smear campaign
because they already thrived on drama. If he fought back, it would only create more of a scandal one
that would backfire on him and to make Gawker more successful.
• The more he thought about it the more Gawker seemed indestructible, but after four years of racking his
brain, Thiel finally found the perfect plan.
• The plan was recruiting the help of a new business partner known only as Mr. A. Thiel established a shell
corporation, this new company would recruit investigative journalists, lawyers and fact checkers who had
only one job - to dig up dirt on Gawker.
• As journalist's Thiel's new team had a unique access to gawker's files and the media savvy to comb
through them for any evidence that Thiel could use to challenge Gawker in court.
• Thiel knew that freedom of speech cases were tough to prosecute and almost impossible to win. He also
knew that technically they hadn't done anything illegal but that just meant he had to find another piece
of evidence he could legitimately take to court.
10. Chapter 4 - Opportunity knocks
• Thiel’s plan was solid unfortunately however so was gawker's alibi. The investigation revealed that
nothing was too low or too slimy for Gawker.
• Despite combing through thousands of files, Thiel and his team found nothing but in 2012 opportunity
knocked in the form of someone else's tragedy.
• In 2012,professional wrestler known as Hulk Hogan discovered he had been filmed having intimate
relationship with his best friend's wife. It popped up one morning on gawker's website.
• Just like Thiel, Hogan tried to fight back. He played nice at first taking discrete legal action by having his
lawyers send Gawker sending cease and desist letter, but Gawker predictably refused to honor hogan's
request.
• Hogan recognize that it would be impossible to beat Gawker with a case predicated on violating freedom
of speech laws, instead he argued that Gawker had violated his right to privacy.
• Thiel instructed Mr. A to contact Hogan and ask if he would be interested in filing his lawsuit in
partnership with an anonymous third party.
• Thiel understood that revealing his interest might be dangerous. If Gawker learned that he was
campaigning to destroy them, their attacks on him might escalate so he wisely concealed his identity and
bankrolled hogan's powerful lawsuit against Gawker quietly waiting for the right time to strike.
11. Chapter 5 - Pride goes before a fall
• Hogan was suing them for $100 million in damages, Denton assumed that Hogan would eventually get
tired of the draining legal fees and back off.
• Denton’s company generated billions in revenue. So, he had the resources to fight lawsuits without
draining a significant portion of his income.
• When the case dragged on and was finally about to go to trial, Gawker began to realize that Hogan
wasn't giving up and that's when they started to worry.
• Gawker offered to settle out of court for a measly $10 million but that wasn't about to dissuade Hogan
who knew that with Thiel backing him, he could fight for far more.
• The case proceeded with the trial ultimately going before a jury and that's when Gawker realized it was
all over for them.
• Unable to play by the fast and loose codes of ethics they had employed in Manhattan, Gawker no longer
had the support that it was expecting.
• Hogan was a hometown hero, Jury didn't want to see their local icon slandered by some media outlet
they had never heard of, so in 2016 the jury came back with a speedy verdict that Hogan had been
awarded $140 million in damages.
12. Chapter 6 – Gawker’s collapse
• Gawker might have had the funding to bankroll an expensive lawsuit even when that dragged on for a while, but
they didn't have the capital to fund a lawsuit for $140 million settlement. Financially crippled by the damages
Gawker had no choice but to fold and declare bankruptcy.
• Hogan and Thiel got what they wanted, justice was served, and gawker's reign of terror had come to an end, but
the story doesn't quite end so happily.
• Thiel had managed to maintain his secrecy during the trial, and he only told a few close friends at the beginning
about his plans. It wasn't long before the story took on a life of its own becoming an international news.
• Surely,the media and the American public should have hailed Thiel as a hero, except they didn’t.
• Gawker was recast as the underdog and Thiel was suddenly configured as a billionaire with a vendetta who
attacked a free speech media house for his own personal gain.
• The public no longer cared about gawkers attack on him or the violation of his privacy, all that mattered was the
impression that they had somehow been deceived.
• Thiel thought he had done the right thing for himself, for Hogan and for everyone else who had been the victim of
gawker's smear campaigns, considered himself a hero.
• Although Gawker might be not upfront about the identity of hogan's benefactor, he didn't do anything illegal and
unlike Gawker he didn't even do anything slimy or unethical. He simply concealed his identity to preserve the
integrity of hogan's lawsuit and ensure that an unethical company was taken down.
• When it comes to cases like this, everyone has an opinion. everyone seems to have their side of the story or their
own version of what they would do in Thiel shoes.
13. Central idea of the book
• Conspiracy doesn’t only bring happiness.
• No one has the right to have the access of other’s privacy.
• Having fun over other’s personal choice
• People move away when you are ageing.
• Even you are a star, once caught you are done.
• Never trust any person blindly.
• Patience.
• Over confidence
• Using money, you can only survive short term.
• Hard work pays off.
16. • Bribing employees at Gawker to leak information.
• Hiring operatives to ruin the company from the inside.
• Instructing hackers to break into Gawker’s email servers.
• Stealing the cell phone of Nick Denton while he dined at Balthazar on a fine morning.
• Attempting to bug the Gawker offices.
• Funding a rival website and operating it at a loss while slowly eating away at the razor-
thin margins of Gawker’s business.
• Creating a blog that writes gossip about Gawker’s writers—returning the very pressure
and scrutiny they’d put on other people.
Identifying and evaluating alternatives
17. Have you ever framed a conspiracy and
got caught before it was fulfilled?
18. • Improvement in gawker’s reputation and fall in Thiel’s.
• Another gossip for gawker.
• Relocation of Gawker’s legal strategy.
• Turning the entire media against him.
• Disturbance in his personal life.
• Negative effect on Co-conspirators.
What if Peter Thiel would have got exposed before the climax?
19. • Misdirecting the viewers of conspiracy.
• Establishing a connection to silicon valley, if law firm was based in San Francisco.
• Threat of being caught in New York or Washington D.C.
• Less popular(Before this case)
• Compartmentalization-Sticking to his job.
Why Wolf Rifkin and Charles Harder, not someone else?
Why Mr. A was chosen by Peter Thiel?
• Young and Ambitious.
• Foreign, No footprint to speak of.
• No connection between him and Peter.
• Act like a Shadow.
• “Professional Son”
• Had same motive as Peter i.e. Destroy Gawker.
20. Gawker vs Peter-Kayfabe or Shoot
Kayfabe-The outcome is predetermined.
Shoot-The script is dopped and real fight begins.
“Gawker thinks this is all kayfabe, but its about to become
a shoot.”
21. • Lack of Lawsuits.
• Start-up by a Peter’s friend.
• Funded by peter in 2016.
• Supporting lawsuits financially which had high chances of winning.
Funding Legalist
22. “The bad economist confines himself to the visible effect, the good economist takes into account
both the effect that can be seen and those effects that must be seen.”
The aftereffects
• Peter’s conspiracy gave the intended outcome.
• Peace prevailed.
• Gawker lost its power to write more.
• New leader took over the other sites.
• Bad articles were removed.
What about the aftereffects of the conspiracy?
23. • The things people don’t say are precisely the things that need to be said.
• As Cicero said, “The beginnings of all things are small”.
• Conspiracies require patience and fortitude.
• There is evil in not acting, in assuming that a bad situation will resolve itself for you or
that others will resolve it for you.
• How do you respond when told “it’s impossible” — is that the start of a new
conversation or the end of it?’
• Lawrence Freedman-Combining with others constitutes the most strategic move”
• “The Briefcase technique”
• ‘To begin, you must study the end. You don’t want to be the first to act — you want to
be the last man standing.‘ — Jose Raul Capablanca
• ‘What do I know about this company that other investors don't know?
• Slow and steady wins the race. But you need to decide which race to run.
• Battle plans are great but ultimately subject to friction — that is, delays, confusion,
mistakes and complications — Clausewitz
• It is difficult to study an enemy you don’t know exists.
What New age entrepreneurs and Managers can learn from the book
24. • The essential trait of a successful man is not only to persevere but almost a perverse expectation
of how difficult it is going to be. The earlier you spot and anticipate setbacks, the less
demoralizing they will be.
• It’s a game of spouses too.
• Hope is rarely enough against an opponent consumed by their cause with victory in sight.
• The greatest sin for a leader isn’t in being defeated. It is in being surprised.
• There is only one danger to a successful conspiracy; when someone is left who may avenge the
dead prince’
So, you must crush your enemies totally
• The best defence to speech you don’t like is to develop a thick skin.
• One person’s liberation can be another’s oppression.
• ‘It is much better to be the last mover’ — Peter Thiel
• Conspiracies have 3 phases:
Planning, Doing and Aftermath
What New age entrepreneurs and Managers can learn from the book
25. • Is spending millions just for the sake of revenge, an act of courage or
foolishness?
• Was it correct to join a 3rd party for the case, without knowing the identity of
investor.
• A short story dragged too long?
• Hiding his own identity, an act of philanthropy or gaining popularity in media?
Our views on the book and story.
How can this book help in one’s career and overall
development?
