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John, how did you come to be a CIA spy?
When I was nine years old, I told my parents that I wanted to be a spy when I grew up.
It came time to apply for college, and I only applied at one university, George Washington University in Washington, because it was two blocks from the White House, and it was one of only three schools in America that offered a Middle Eastern studies program.
I was one of only four people in that brand new Middle Eastern Studies program.
I stayed for a master's degree in legislative affairs with a focus on foreign policy analysis.
I was taking a class in that program called The Psychology of Leadership.
It was taught by an eminent psychiatrist named Dr. Gerald Post.
And
He gave us an assignment one day where we had to shadow our bosses.
We had to just follow our bosses for a week.
Your bosses?
Yeah.
I worked at a labor union called the United Food and Commercial Workers Union.
And so we were just supposed to follow our boss around for a week and then write a psychological profile.
I used dozens of footnotes from psychology texts, and I ended up saying that he was a sociopath with psychopathic and possibly violent tendencies, and I had these citations.
I passed the paper in.
Dr. Post gives it back to me a week later, gave me an A, and then he wrote, please see me after class.
So I went up to him after the class, and I said, Dr. Post, you wanted to see me.
He says, come to my office.
So we went down there.
He closed the door, and he says, listen.
I'm not really a professor here.
I'm a CIA officer undercover as a professor here.
And I'm looking for people who would fit into the CIA's culture.
I think you would fit into the CIA's culture.
Would you like to be a spy?
And I said, yes, I would.
He picked up the phone and called a number.
And he said, Bob, this is Jerry.
I've got a good one for you.
Do you have some time?
And he said, sure.
He writes an address on a scrap of paper and he says, be at this address in 20 minutes.
It was only one subway stop away.
So I jumped on the metro.
I went to Roslyn, Virginia, just across the river.
I had to buzz to be let in.
And a woman opens the door.
She says, are you here for Bob?
And I said, yes.
She says, come on in.
I'm sitting there for a moment and then this like six foot six, 350 pound giant barrels out of his office.
And he says, John, Bob, how the hell are you?
I want you to be at the George Washington University Medical School Saturday morning at eight o'clock.
We've got some tests for you.
I said, okay.
And then we shook hands and I left.
So Saturday morning, I went to the GW Medical School auditorium.
There were like, I don't know, 200 people there.
And they hand us a test.
My wife picked me up.
She said, how did you do?
I said, I have no idea.
Does your wife at this point know that you're applying for the CIA?
Yes, and that was going to be pretty much the extent of what she ended up knowing.
Because once I got in...
But you were allowed to tell her?
I was not allowed to tell her.
No.
So you told her anyway?
Yeah.
Yeah.
When I first applied, they said, listen, don't tell anybody because you may go under cover, you may go under deep cover, and we can't have people out there who know that you're a CIA officer.
Presumably, the CIA are smart enough to be able to check if you've told her.
Yeah.
And they ask you on the polygraph, did you tell her?
Really?
And I said, yeah, I told her.
She's my wife.
What am I going to do?
But it got to the point where I'd get home from a day where I broke into some guy's house and planted a camera on a bug.
And I'd get home and she'd say, how was your day?
I'd say, great.
What did you do?
Not a darn thing.
And then my phone would ring at midnight and a guy would say, the rain in Spain falls mainly in the plain.
And I'd say, mares eat oats and does eat oats and little lambs eat ivy.
And that means meet me at the yacht club parking lot in three hours.
And then I'd leave.
She would say, where are you going?
It's midnight.
I got to work.
So I'd leave.
I'd do my meeting.
I'd come home, 6 o'clock in the morning, just in time to shower and shave and get dressed to go to work.
And she would say, what was her name?
And I remember this one terrible time.
That's what she said to me.
What was her name?
The truth is, I had been sitting in a garbage dumpster.
Waiting for a guy to drive by down the alley and throw a bag of documents in.
And I stunk of garbage.
And I said to her, do I seriously smell to you like I've been with a woman?
Seriously.
So we ended up getting a divorce.
So you do the assessment.
Presumably you get in.
Yeah.
He called me like two weeks later.
Bob did.
And he said, you blew the doors off those tests.
I said, oh, great.
OK.
So a month later, they summoned me to headquarters.
And I was interviewed by the Office of Near Eastern Operations, the Office of Near Eastern Analysis, and the Office of Leadership Analysis.
I was offered the analysis job on the Iraq desk.
And what is the sum total of the training you were given in the variety of different roles?
Like, how do they train this body?
That's a good question.
And the answer is vastly different depending on where you start your career.
So because I started mine in analysis, the immediate...
Training was in mastering the CIA's writing style.
So the most important product that the CIA writes every day is the PDB, the President's Daily Brief.
And it tells the president what?
What you think he needs to know.
Okay.
So for example...
When the Iraqis began moving to the Kuwaiti border, we had this big debate.
Are they going to cross the border?
Yes or no?
So I said, listen, why don't I call the American defense attache in Baghdad?
And I'll just ask him to drive down there and look and tell us what he sees.
He drives down there, drives back.
He calls me and he says, literally the entire Iraqi military is on its way to the Kuwaiti border.
So we wrote a thing for the president saying Iraq is going to invade Kuwait and it's probably going to happen in the next 48 hours.
And when did the president see that particular briefing?
At 7 a.m. the next morning.
Okay.
And is there ever situations where the president would get it in the middle of the night?
Yes.
Yeah.
And be told in the middle of the night that.
Yes.
There are these levels of immediacy.
There's routine, which is like who cares.
And then there is priority, which means I'll get to it sometime today.
Then there's immediate, which means you should probably read it first.
But then there's flash, which means, oh, my God, something terrible just happened.
You should probably wake the president.
And then there's critic, which means they're coming over the embassy walls.
We're at war.
Wake up the president.
Scramble the jets.
9-11.
9-11.
That's a critic.
So going back to this question of your training, what is it that the CIA teach you about human nature and how to use human nature to your advantage?
That could be transferable to other disciplines in life like business or…
Well, this is going to sound not very nice, but it's real life.
It's everyday life, especially in business.
The CIA actively seeks to hire people who have what they call sociopathic tendencies.
Not sociopaths.
Sociopaths have no conscience.
They'll just blow right through a polygraph exam.
But they're impossible to corral.
They're impossible to keep.
Under rain, and it's because they're not able, their brains won't allow them to feel regret or remorse.
Now, in business, most CEOs are sociopaths.
Most, not all, but most, especially in big companies because they claw their way to the top, usually on the backs of the people around them.
They don't feel bad screwing the next guy to get that next promotion.
The CIA wants people like that.
Because those are the people who are going to break into a foreign embassy.
A normal person would not advocate breaking into a foreign embassy that's sovereign territory of a foreign country.
I would.
I'd be glad to do it.
Why?
Because we're the good guys.
So do you have sociopathic tendencies?
Absolutely.
And what are your sociopathic tendencies?
My sociopathic tendency was to operate in legal, moral, and ethical gray areas specifically.
That's what it was.
I'm really curious about what we can learn about human nature from someone whose job was to meet strangers and to get them to basically sometimes to turn against their own country.
I'm really interested in – and I think it's informative because so many of us, you know, when we think about what good leadership is or what good salesman or womanship is –
It seems like there's transferables.
I guess for some people it's family.
I guess for some people it's something else.
That hook that you're talking about, that thing that gets them.
And the word that they use at the CIA for the hook is a vulnerability.
And it's not really a vulnerability in every case.
95% studies have been done about this internally at the CIA.
95% of the people who agree to become spies for us do it for the money.
It's a simple cash transaction.
You give me money, I'll give you secrets.
95%.
So you're telling me that you think human motivation is 95% driven by money?
Yes.
Really?
Yes.
The rest was love and family, ideology.
Revenge and excitement.
You're going to get a handful of people who are hooked on James Bond movies and they will do it.
I mean, you're going to pay them anyway, but they will do it just for the adrenaline rush.
It's interesting because when I look at this list of things and I compare it to business...
I would say it's slightly different from my experience of hiring people, specifically of hiring people.
I tend to think that
You know, one would ask themselves, why would someone leave a company right now like, I don't know, OpenAI and go work at a startup?
They're going to get paid way more at OpenAI.
You've got this equity and these grants.
But people are en masse doing that.
And even when I think about the early days of Google, people left the big conglomerates that would pay them more.
And they went and worked for Larry and Sergei.
Getting paid way less, but to be involved in something small, scrappy, exciting.
And this is what I think about when I sit, you know, probably I've had thousands of people in my life now across my businesses.
And money is a factor, but it doesn't tend to be the biggest factor necessarily.
It tends to be, in my experience, there's a particular hero's journey in their mind that they want to be seen through.
They want to complete.
You know, there's a particular way that they see themselves and they want to fulfill that.
Oh, I could get that.
I work with a very, very tiny startup right now called Ivy Cyber, and it focuses on privacy software, things like scrambling your data so it can't be intercepted, that sort of thing.
And I've participated in a couple of pitches to angel investors.
And they all say exactly the same thing that you did.
And this is why I was confused when I heard that money was 95%, because I just think, especially in the work that you, I don't know, especially in the work that you do, I would assume...
But look at it this way.
I think this would explain the discrepancy.
You're comparing people who are making a life versus people who are betraying their country.
True.
And what's interesting as well is in those examples that you've given, money is actually a proxy to be able to take care of my family.
Yeah.
And to be able to, you know, fulfill my ideology.
And maybe to get excitement and revenge.
Do you know what I'm saying?
So even that guy that wanted the plane ticket so he could fly home.
Yeah, the money could have got him home if you'd just given him.
But the reason why he wanted to go home was because his family.
His family.
That was it.
What's the extent of the things that the CIA can get as an incentive for someone to turn against their nation to give secrets?
Quite literally anything you can imagine.
Even if it's against the law?
Well, they're not going to get like drugs or, you know, child prostitutes or no, not stuff like that.
What if someone said, I want you to get me a green card?
Oh, yeah, sure.
What if they said...
If the information is good enough, not a problem.
What if they said, I want you to, I've got this tax bill.
I want you to make the tax bill go away.
Okay.
Give me the plans to that Russian tank.
We'll make it happen.
What if it was an American?
Would they speak to the IRS here and just get rid of it?
Oh, if it was an American citizen, you mean?
Yeah.
No.
But why?
No.
We normally don't recruit American citizens.
By law, the CIA can't operate domestically, although they have offices all over the country.
Those offices are generally to debrief.
Business leaders, C-suite officers who traveled to denied areas.
For example, if you take a trip to North Korea, let's say, I'm going to call you and I'm going to say, you don't know me, but I'm from the CIA and I understand you just went to North Korea.
And I was wondering if I could come over to your office for an hour and just ask you about your trip.
99.99% are going to say yes because they're patriots.
So I go to your office, I give you my business card, and we just chat about, you know, your impressions of the place and that kind of thing.
Just to close off on this point, are there any skills that the CIA taught you or trained you in that you think are transferable for business that we haven't talked about?
They trained us also in lying and lie detection.
That was actually quite important.
You know, at the CIA, you're a trained liar.
And this is why the divorce rate is so high.
It's the highest divorce rate of any entity in the U.S. government.
It's upwards of 80%.
Trained to lie.
How do they train you to lie?
Hi, my name is Dave Phillips.
I work for an import-export company.
But do they teach you the art of lying?
Oh, yeah.
And what is the art?
You know, it's hard to pin down.
You just sort of have to have it.
You have to have that ability.
But the hard part is you have to keep the lies straight.
I'll give you another example.
I've never told this story before.
I was asked by headquarters.
I was overseas in the Middle East.
And I was asked by headquarters to target one specific officer of this foreign country.
Target?
Yeah.
Hi, how are you?
Oh, we've never met.
I'm John.
So nice to meet you.
Let me take you to lunch.
He had access to information that we really needed.
So they told me to accidentally bump into him.
So I surveilled him for a week and he was single.
And on Saturday morning, he went to a coffee shop.
So I go into the coffee shop and I'm looking at him and he's looking at me and I said, I know you.
Ministry of Foreign Affairs?
He said, yes.
Do I know you?
I said, I am John from the American Embassy.
Oh, nice to see you.
I said, hey, good to see you too.
Do you live in the area?
Yes, I do.
I said, oh, so do I. I didn't.
I lived like across town.
Oh, fancy meeting you here at this coffee shop.
I come here all the time.
Do you?
Yeah, he says.
I come here all the time.
Why don't you have a seat, he says.
So I sit down.
At the end of the conversation, I go back to the embassy and I read a cable and I said, he's gay.
I'm 100% sure he's gay.
So then we started this conversation, headquarters and I, how can we use that to our benefit?
Did he have a wife?
No.
Which was unusual at his age.
How did you know he was gay?
Oh, I just, it was a vibe.
Okay.
So headquarters says, we want you to pretend that you're gay.
I said, oh, come on, you guys.
No, we really need the information.
You got to pretend that you're gay.
I said, okay, I'll do it.
I'll do it for uncle Sam.
So I call him and I said, Hey, I have two tickets to this show.
And I was hoping maybe you'd be free.
Maybe we'll grab some sushi afterwards.
He said, yeah, I'd love to.
So we go to the show.
He thoroughly enjoyed it.
And we go for sushi afterwards.
And then we go out again.
And he says, why don't you come over to my place some night and I'll make dinner.
I said, great.
So I go over to his place.
He made a lovely dinner.
And then I thought, well, I have to invite him to my place.
So I told my wife, you're going to have to like get out.
So she left.
I made dinner.
I removed all the pictures of us together and we had just gotten married.
So we had like our wedding picture up and everything.
At the dinner.
He leaned in to kiss me, and I instinctively backed off.
And he said, oh, my God, I'm sorry.
I thought you're gay.
And I said, oh, no, I am gay.
I'm not into hairy guys.
And he's like, oh.
Okay.
I said, I'm sorry.
I think you're great, but I'm not feeling it.
You didn't kiss him?
No.
So we remained friends.
And in the end, he gave me the information.
Because we were friends.
And then he opened up.
He's like, I can't tell anybody I'm gay.
They suspect I am.
And they passed me over for promotion.
And my boss asked me, is there something in your personal life that you're not telling me?
He knows I'm gay.
I said, listen, your culture's backwards.
Don't tell them you're gay.
Just say that you've just never met the right woman.
And inshallah, the right woman is coming, you know, in your life at some point.
And I actually Googled him a couple of years ago and he did become an ambassador finally.
And he's still working in that country now.
Does that kind of still happen a lot in the CIA where you have to take one for the team?
Yes.
Have you ever taken one for the team?
No.
I'm not sure you're telling the truth.
Well, it came close.
When did it come close?
So I was overseas.
I was a brand new operations officer.
And there was a woman in this foreign intelligence service who was the ugliest woman I've ever seen in my life.
Like you want to avert your eyes.
Like she came off the side of Notre Dame.
She was a stone gargoyle with a giant mole right here with a giant hair coming out of it, that kind of ugly.
So I took her to lunch, and she was very nice.
And then I thought – I did something kind of gutsy by CIA standards because it was early on in our relationship.
I invited her –
To go to lunch on a Saturday.
Now, as a rule, the people in this country were not allowed to socialize with us privately.
It had to be like their whole office or several of them together.
So I asked her just to meet me
Privately for lunch on saturday don't tell anybody
So she was someone from the middle east yes and she agreed
And i was like oh my god she said yes and i ran back to the office
I was like she said yes to a lunch on saturday alone and my boss says okay here's what i want you to do
I want you to fuck her
And I said, what?
I said, have you ever seen her?
And he said, I know, but we're the good guys and you're going to have to take one for the team.
And I go, oh my God.
I said, I go, okay, I'll do it.
And he says, no, you're not going to fuck her.
We don't do that.
I said, I don't know.
I just started this.
I've never been an operations guy before.
How am I supposed to know?
He said, come on.
He said, just develop her like a normal person.
You don't have to fuck her.
I said, oh, my God.
You almost gave me a heart attack.
But they –
Might not be mad if you did.
So long as I reported it and I got the recruitment out of it.
It wasn't illegal to, you know, sleep with assets.
Yeah, you're not supposed to sleep with assets.
It has happened to a couple people I know.
And they end up being pulled back to the United States.
You have to sit in the penalty box if you do that.
You're not supposed to do that.
But, yeah, it happens sometimes.
So sextortion isn't a real thing.
It can be.
We don't.
When I first got hired, one of the old-timers told me the story about an ayatollah that they were trying to recruit.
And they set this ayatollah up with a prostitute.
And he had sex with this prostitute in a room where they had cameras everywhere.
And so they bumped him afterwards.
They bumped into him and said, hey, we have all these pictures.
And they laid out the pictures of him butt naked with this prostitute.
And he said, yeah, give me that one, an 8x10.
Give me two 5x7s of that one.
How about some wallet size for this?
He's like, get out of here.
And he said, you know, after that, we just stop doing that.
It doesn't work.
When you recruit somebody, you really do need the relationship to be based on mutual trust.
Not coercional pressure or threats.
Threatening somebody, it's not going to result in a productive relationship.
The Russians do it.
The Israelis do it.
But most intelligence services around the world don't.
Because you've been in this world, what is it that you know about the nature of the reality that we all live in that the average person really has no idea about?
Do you know what I mean?
Yeah.
Because, you know, going back to what I said earlier, three years ago before I started doing all this podcast stuff and started interviewing people that had been involved in spy work and the CIA and all this, I was kind of like naive to the way that the world worked.
Sure.
I thought if I have a password on my device, my device is secure.
And I thought that, you know.
Right.
All these kind of just simple things.
But what is it that you know about the nature of reality that most people don't?
Well, I guess it's a couple of things.
You know, John Kennedy called the CIA the best and the brightest.
And we're not, we're just average people.
And we're not as smart as we think we are.
We're not as worldly as we think we are.
We've pretty much missed every major global development since 1947 from the rise of the Berlin Wall to the fall of the Berlin Wall to the fall of the Soviet Union to the Suez Crisis and the Iran hostage crisis and 9-11 and everything else.
We missed it.
We're really good at day-to-day updates for the president.
We're really good at recruiting minor hangers-on around terrorist groups, but the big picture items, we're just not good at it, number one.
Number two.
Until 9-11, it was against the law, like in stone, to spy on Americans.
And now billions of dollars are spent spying on Americans, whether it's NSA or CIA or FBI or intelligence community contractors.
Nothing is secret.
Nothing.
And to make matters worse, let's say maybe you did do something that law enforcement might be interested in.
They don't need a warrant anymore.
They don't need to go to a judge and say, well, we have reason to believe, blah, blah, blah.
All they have to do is just buy your metadata because it's for sale.
Just go to the carrier.
Just buy it.
They don't need a judge's order to do that.
It's all out there.
We've made ourselves vulnerable.
All of our lives are out there, whether it's on Facebook or X or Insta or whatever.
If they really want to get you, they're going to get you, which reminds me of a book called
Written by Dr. Harvey Silverglate.
He's a professor of law at Harvard, and it's called Three Felonies a Day.
And he argues in this book that we are so over-criminalized, so over-regulated in this country that the average American on the average day going about his or her normal business commits three felonies every day.
You may not mean to, but you do every day.
So if they decide they want you, they don't like your politics, they can get your metadata.
They can go through that metadata, find crimes that they can charge you with and ruin your life.
And there's nothing you can do to protect yourself.
To some extent, they did that to you.
Yeah, they did.
They did that to me.
Because you spoke out about a torture program that was happening in the CIA.
Yeah, John Brennan wrote a letter to Eric Holder and said, charge him with espionage.
And Holder wrote back.
Eric Holder was the attorney general.
Holder wrote back and said, my people don't think he committed espionage.
And John Brennan wrote back to Holder and said, charge him anyway and make him defend himself.
So they arrested me and charged me with five felonies, including three counts of espionage.
Espionage can be a death penalty case.
Charged me with espionage.
They waited until I went bankrupt 10 months later with $2 million in legal fees.
And then they dropped the espionage charges.
And they said, we can re-add the espionage charges or you can take a plea to this lesser charge.
What are you going to do?
Roll the dice knowing that the government wins 98.2% of its cases according to ProPublica?
Or do you just take the deal and make it go away?
And that's what I did.
And you got roughly two years in jail.
Yeah.
I ended up doing 23 months.
Mm-hmm.
And for anyone that doesn't know, this was because at some point in your career, you spoke out about torture programs that were happening in Guantanamo Bay and elsewhere.
Yeah, and at secret prisons that the CIA had set up around the world, right?
Yeah.
And going back up to the top of my question here, I'm really trying to speak to Jane, Dave, who's listening to this right now.
Sure.
They have a normal life.
Yep.
They're not really aware that spies exist in the extent of the work they do.
They kind of assume that everything they see and people they interact with are normal and they think their devices and everything else is secure.
What message do you have for them?
A word of warning or caution about the reality?
Yeah, that's a good question.
Eliot Spitzer, the former governor of New York, when he was attorney general of New York, he said –
Don't nod when you can motion.
Don't speak when you can nod.
And don't ever put anything in a text message.
At the CIA on our very first day, they told us not to ever say or do anything
That we would be ashamed to see on the front page of the Washington Post.
I took that seriously.
The truth of the matter is, because of technology the way it is today, our whole lives are out there potentially for someone to see, for someone to use against us.
So be careful what you say, be careful what you write, even in jest, because it can be taken out of context to target you.
And what about digital security?
You talked about the fact that it's possible for these forces, and not just the US, but other countries, to be able to hack and crack your devices and see anything on your devices.
I think we all go around assuming that our devices are secure.
They're not secure at all.
At all.
It's not just NSA, CIA, FBI that you have to worry about.
It's the British, the French, the Germans, the Canadians, the Australians, the New Zealanders, the Russians, the Chinese, the Israelis, the Iranians.
I mean, everybody has these capabilities.
Everybody.
So you've got to be very, very careful.
Capabilities to do what?
To intercept communications.
I've heard you say that they can hack car systems.
So they could theoretically hack into my car.
Yes, we know that from WikiLeaks.
There was something in 2017 called the Vault 7 revelations.
There was a CIA software engineer who was disgruntled.
And instead of going to the Russians or the Chinese –
He went to WikiLeaks and he downloaded thousands, tens of thousands of pages of documents classified above top secret.
And they became what WikiLeaks called the Vault 7 documents.
So they included things like...
The CIA, for example, will hack into, let's say, the Iranian Ministry of Interior computer system.
But they'll leave little electronic clues all written in Cyrillic.
Cyrillic is what?
Cyrillic is the alphabet, the Russian alphabet.
Oh, okay.
Yep.
Or…
They can take control of your smart TV remotely and they can make the speaker turn into a microphone.
So even though the TV is off,
It can still hear everything that's being said in the room and broadcast back to the CIA.
Can they do that with devices?
Oh, they could do that.
When I first got hired, they were able to do that.
So you could be doing that right now with no iPad.
Oh, totally.
Absolutely, yes.
That's old technology.
And then the thing about the car, this was revelatory.
They can take control, again remotely, of a car's computer system in order to –
Well, I mean, in order to kill you.
Crash the car.
Crash the car, take it off a bridge, take it into a tree.
Sure.
What you just listened to was a most replayed moment from a previous episode.
If you want to listen to that full episode, I've linked it down below.
Check the description.
Thank you.
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Their portfolio managers approach data from multiple perspectives.
Analyzing trends and conducting deep research to give you their curiosity-backed active management expertise.
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Investors generally incur the cost of the spread between the prices at which shares are bought and sold.
Buying and selling shares may result in brokerage commissions, which will reduce returns.
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