Alexander the Great was a remarkably driven and fearless leader who lived only 32 years, yet left an enduring legacy. Born into a militarized Macedonian kingdom, he displayed early signs of self-discipline, ambition, and a hunger for glory, even as a teenager. Under his father Philip’s guidance, Alexander was educated by the renowned philosopher Aristotle, gaining not only ethical and political wisdom but also access to esoteric knowledge reserved for a select few. This deep intellectual foundation, combined with his unrelenting willpower, enabled him to lead vast military campaigns across Asia and Africa, conquering empires and expanding the known world. Despite being physically and emotionally vulnerable—experiencing wounds, alcoholism, and personal tragedy—he remained committed to action, speed, and decisive leadership. His belief in divine lineage and heroic destiny fueled his boldness, while his refusal to accept defeat or delay proved pivotal in victories. Though criticized for arrogance and excess, Alexander demonstrated self-awareness and a willingness to repent. His story resonates across time because it embodies the tension between ambition and self-destruction, highlighting how extreme drive—when channeled with discipline and purpose—can lead to greatness. Modern reflections on entrepreneurship, leadership, and education echo Alexander’s journey: the value of learning from rare mentors, the power of endurance, and the danger of arrogance. Ultimately, Alexander’s legacy is not just in conquest, but in the enduring human traits of courage, resilience, and relentless pursuit of excellence.
Alexander lived for 32 years and eight months.
He ruled for 12 years and eight months.
He was handsome, embraced, hardship, and had the sharpest of minds.
He was extremely brave and dedicated himself to both honor and to taking risks.
He had an insatiable appetite for glory.
Even when circumstances were unclear, he was highly skilled in seeing what needed to be
done.
When it came to drawing up, arming and equipping his army, he was highly knowledgeable.
He was able to raise morale among his soldiers, to fill them with hopes, and through his own
fearlessness to dispel their fear in times of danger.
At moments of uncertainty, he acted with the greatest courage.
He kept his promises.
It is true that passion or temper may have sometimes led Alexander astray, that to some
degree he inclined towards arrogance.
But Alexander was noble enough to repent for his errors.
Whoever would reproach Alexander should first weigh up his own personality and achievements
against Alexander.
It is my opinion that at that time there was no nation, no city, not even one man who
had not heard the name of Alexander.
That is an excerpt from the last chapter of the book I'm going to talk to you about today,
which is Alexander the Great, the brief life and towering exploits of history's greatest
conqueror, as told by his original biographers.
Okay, before I jump back into the book, I want to go back a few episodes ago on episode
number 226.
I read this book called Heroes.
It is by this fantastic writer named Paul Johnson, who I just discovered and absolutely
loved.
And I'm starting to devour his books.
And he breaks down.
There's like 30 heroes throughout history, Alexander being one of those heroes.
He's got this fantastic chapter in the book.
It's called Earth Shakers.
And it's one chapter dedicated to Alexander the Great and Julius Caesar.
And I want to read a few quotes, I want to review some quotes from that book before we
jump into this new Alexander biography.
And so this is coming from the book Heroes.
Again, you can see the episode and the book link on episode number 226.
So first he says it's talking about the introduction to this paragraph is comparing the traits
that Julius Caesar and Alexander the Great both share.
And it says they carved out vast empires for themselves and hammered their names into
the history of the earth.
Each was brave, highly intelligent, almost horrifically self-assured, whose ambitions knew no
bounce.
They were both also selfish, cruel, without scruple and fundamentally unlovable.
But they were admired, inevitably more perhaps than any other two men of their kind.
They were giant like almost superhuman in every respect.
And then I just want to pull out a few sentences from just about Alexander.
So it says he was a man of formidable achievements.
He was highly creative.
He woke up early.
His diet was spare.
He learned to drink heavily and that was, to my opinion, his downfall, which I'll get
into more in his biography.
He was skilled with the sword and the spear and an expert at all forms of arms drills.
This was his trade from boyhood.
He dressed to be seen in that flamboyant dress and goes into detail in the Alexander
biography.
He dressed like that even during battle, which seems a bit crazy because the fact that
he's standing out makes him a greater target.
He read Homer all of his life and he knew the passages by heart.
It was to him a Bible.
It was like the book was a guy to heroic morality, a book of etiquette and a true adventure story.
He believed he was descended from the gods.
This belief gave him a certain fatalism which made the risk of death unimportant to him.
Alexander traveled over 20,000 miles.
Most of it on foot in difficult mountain and desert terrain.
How did he do it?
The most important factor, as always with successful statesmen and men of action, was sheer willpower.
He had supernatural self-confidence and persistence.
There is no substitute for will.
He invariably led from the front.
He was wounded nine times.
And finally, Alexander thought, decided, and above all, moved swiftly.
He appreciated the importance of speed and the terrifying surprises speed made possible.
He invented the blitzkrieg.
Okay, so now I want to jump into today's book.
Here Heroes is 226.
The reason I recommend that book is because I think it's like 200 pages.
The episode I did before that, episode 225.
It was also written by Paul Johnson and it was a 190 page biography of Churchill.
And what I liked about it is Paul writes in very short sentences.
There's no fluff.
It's very easy to understand.
To this book, although the book I'm holding my hand is only 150 pages, it's more difficult
reading and I'll tell you why.
Because outside of the introduction, so the introduction is going to be written by the
scanning Michael Wood.
The rest of the text is biographies of Alexander that are 2000 years old.
Okay, so it says the text in this collection are drawn from three ancient biographies of
Alexander the Great, who died in Babylon in 323 BC at the age of just 32, having conquered
half of the known world.
His is one of the stories in history that has had the power to captivate every generation.
So that's a crazy statement.
If you look up, okay, how long is generation?
People say it's usually between 20 and 30 years, so let's take the middle point 25 years,
that means that's 92 generations since Alexander died and we're still talking about them.
And it gets into why, why would that be a little bit here?
Says the internal fascination with Alexander is not due only to his amazing events he set
in motion, but also to the tangle of history and the myth that surrounds him.
As the Greeks said, those whom the gods love die young.
Then the book gives us a little bit of background into the environment that Alexander was born.
In addition to reading this book, I also re-listened, I've recommended this podcast
too much times, but it's Dan Carlin's Hardcore History Addendum Feed.
It's called Glimpses of Olympias.
It's like a three and a half hour podcast and the main character of the podcast is Alexander's
mother, but it also talks about a lot of Alexander and about his father, and so we're going
to get into that.
The Macedonians were a rugged people.
Alexander's father, Philip, had created the kingdom of Macedonia with a powerful army
that crushed all opposition.
And the reason he just referenced that episode is because it talks about how formidable Dan
talks about how formidable Philip was.
The accomplishments of that Alexander achieved in his lifetime would have been impossible
if he was born to a different father.
So it talks about there's a prehistory to Alexander's birth and it's this constant war
between the Persians and the Greeks and the Greeks and so it says, and this is also the
reason I'm reading this section to you is because it gives you an insight to just how
grand and a little bit crazy that Alexander was.
150 years earlier, the Persians had attempted to conquer Greece only to be decisively defeated.
To the Greeks, the Persian War represented a Latter-day heroic age.
They had never forgotten the desecration of their temples and they had long been long been
talk of mounting a war of revenge.
Okay, so they're talking about something that happened 150 years earlier, right?
Alexander became ruler of Macedonia at the age of 19 after his father's assassination.
Two years later, he set out on the Great War of Retribution against the Persians.
So in the previous book talks about, hey, he had an unquenchable thirst for glory.
He thought he was a senate from the gods.
He had no fear of death.
Think about this at 19 years old, you think it is your place in history to take revenge
on something that happened 150 years previous.
It is unapologetically extreme, so from this point, when he starts this war with Persia
until he dies, he is just going around conquering the entire world.
So to give a brief overview, I'm going to go to the end.
This is just the introduction, keep in mind.
So it says that at this point, the heat, the monsoon rains, disease, and local resistance
all began a road morale.
Alexander's army showed its disinclination to go any further.
From then on, certainly with hindsight, his dream begins to unravel.
We hear reports of drunkenness and get the impression of a lack of direction.
The death of his friend and lover, after a massive binge, seems to have led to fits of
murderous fury and bouts of depression.
Wounds and sickness had also taken, no doubt taken their toll, and in 323 Alexander died
in Babylon.
Probably from medical complications exacerbated by alcoholism, although there were persistent
rumors that he had been poisoned by disenchanted members of his court.
Those are the bare bones of the story, it was one of the great episodes of history of the
world, in the history of the world, an extraordinary tale of bravery and cruelty, endurance, and
excess.
Chivalry in greed, a journey of 10 years and 20,000 miles.
The empire broke up rapidly after Alexander's death.
Then it goes into the fact that he was famous in his own day, right after, and as he continues
to be really famous today, so says his legend spread to every corner of the old world.
Alexander appears in the Bible, he appears in the Quran.
There are over 200 different Alexander epics and poems in mid-Evil European languages
alone.
There's an Indian legend about Alexander that said he had found the speaking tree, which
had foretold his destiny, to die young but win eternal glory.
And then before I continue in the introduction, I want to go back to that one paragraph where
it talks about, he starts binge drinking, becomes alcoholic, I think one of the benefits
of reading biographies is that you see all these very smart and formidable people make
mistakes and struggle.
And one thing that you notice is the same extreme traits that allow them to achieve abnormal
or unusual success can also cause their downfall.
And so the less than I always take away from this, this is very, these kind of personality
types.
It's very hard.
It's almost no such thing as moderation to them.
I always think back to that Edwin Landquot, where he's like, there's something they don't
teach at Harvard Business School, and it's if anything's worth doing, it's worth doing
to excess.
And so I think Charlie Munger has the right idea on this, it's just you have to understand
you're highly driven, somewhat crazy person to pursue.
I think almost all entrepreneurs, that's why. these things called the misfit feed, right?
We're just not normal people.
And so entrepreneurship is a vehicle to channel all this energy
into something positive.
But Charlie Munger makes the point that a large part
of succeeding life is just avoiding bad habits.
And there's a number of quotes he has about this,
but one specifically about alcohol
to relate it back to what we're learning about Alexander right now.
He talks about, this is a quote from Charlie Munger.
He says, "The four closest friends of my youth
were highly intelligent, ethical, humorous types.
They were favored in person and background.
Two are long dead with alcohol, a contributing factor.
And a third is a living alcoholic.
If you call that a living."
And so you go back and you really think about what--
how he started off this thought.
He brought up the point because you say,
oh, this alcohol, that person's just
undisciplined, not very intelligent.
He let-- they let the substance destroy their lives.
But Charlie starts out that sense, that paragraph,
with they were highly intelligent.
And that ties back to what you and I are doing,
in fact, that we're reading biographies.
We're learning from biographies constantly.
You'll see this over and over again, OK?
This is a smart, driven, formidable person
that made a mistake.
It's silly to think that I won't do the same thing.
So I need to learn from their experience.
I want to avoid.
I do not want to die.
Young or have my hopes and dreams dashed
because I couldn't stop drinking or being addicted to drugs.
OK, so let's go back to the book.
The guy writing the introduction, his guy name Michael Wood.
What he is doing while he's writing the introduction,
he's retracing Alexander's steps through,
like literally where he goes, right?
So he's trying to follow this path.
It's like 20,000 mile path.
And he's reading these three biographies.
He has the three biographies with him.
And the crazy terrain and the terrible weather
and all the stuff that Alexander had to endure,
he talks about that here.
So he's giving us insights into Alexander the Great.
And I want to combine something that Michael writes here
with a discussion I just had with a founder and investor
who listens to this podcast.
So he says, well, we also gain on the ground.
And especially from his night marches at high altitude
in the pitch dark was, of course, an insight
into Alexander's character.
The implacable drive were morseless, unstoppable.
His incredible mental energy and almost
excessive tolerance of fatigue.
What one of his biographies calls his pathos,
his desire to win and excel his drive.
And so I double underline that one section,
where it says, almost excessive tolerance of fatigue.
And so I get to the section, I was like, wait a minute.
That's a really interesting trait to have.
And I think it should be combined with another trait
that I just learned about.
So there's a founder and investor named Seth,
who listens to this podcast.
I've talked to him before he happened to be in town.
We went up meeting up and just discussing all kinds
of ideas about entrepreneurship for a few hours.
And he was telling me about one of the most formidable
entrepreneurs that's part of his portfolio.
And the way this guy thinks and some traits he has.
And Seth said something.
And after he said, I said, hold up.
I had to pull up my phone.
I was like, I got to write that down.
I cannot forget that what you just said.
And he said that this founder had an intolerance for slowness.
So the importance of speed comes up over and over again
in these biographies, right?
But what if like now where we are in this section of the book,
the renewing off myself is we should combine
an excessive tolerance of fatigue
with an intolerance of slowness.
And the reason I think that came to mind
when I was reading this is because I think Alex and I had
both of those traits.
He prioritized speed over and over again.
There's sometimes where he's getting more resistance like some
as he goes around all these conquests.
Some people just fold or he moves fast.
Where he kind of runs over the opposition rather quickly.
But there's sometimes when he's pushed back
and he's got a great creative or find another way in.
And there's a discussion was like, oh, maybe instead of spending
an extra day or two here, maybe should just move on
to something to another city that I could conquer faster.
And so then the author continues here.
This is going to remind me one of my favorite things
become like almost like a maximum or something
I repeat myself over and over again when it's inevitable
that you're going to come into some form of discomfort
in your work, right?
And it's the fact that what the founder for seasons
is the sharp said.
And he said the excellence is the capacity to take pain.
And so that is a main theme in this book.
And Alexander specifically says that over and over again
that all the things that you want in life
are on the other side of difficulty and discomfort.
And so his point to his troops is like, therefore,
it's not something to avoid.
It's something to embrace.
And so it says, nothing put him off.
In spite of everything, Alexander just kept coming on and on.
The freezing cold and the starvation
made it a tremendous task, but they could not stop him.
And in the end, his enemies were struck
with fear and amazement at the speed of his advance.
And so the introduction ends with Michael getting
to the end of Alexander's journey.
So it says, when our own journey in Alexander's footsteps
was over, I remember sitting in the sweltering little
port on the edge of the forbidding Mark-Marc-Marcran desert,
which Alexander crossed on his desperate return from India.
As a wind, as a wind hot as an oven,
swept in over the fiery gravel landscapes
and sand dunes of the desert, I turned to Aryan's last page.
So this is one of the, his, one of the biographies that's
quoted heavily in this book.
And this guy's writing 2,000 years ago.
And this is what he says.
Anyone who belittles Alexander has no right to do so
on the evidence.
It is my belief that never in the world
was there another like him.
OK, so from here on in the book,
they take these three ancient texts
and they organize them and build a unique narrative,
the combination of these texts.
And they do that because some biographers
are very negative about Alexander.
Some are very positive.
A lot of the text is details about specific battles,
stuff like that. I'm not going to talk about that at all.
I'm interested in who he was as a person,
the traits he had that we could use in our own work.
And then if he has like a useful idea or something like that,
I pulled that out.
And so we're in the section about his early life.
He's about a teenager.
And it just goes in chronological order from here.
So it says, even when he was still a boy,
he gave plenty of evidence of his powers of self-control.
His passionate desire for fame implanted in him
a pride and a grandeur of a vision
which went far beyond his years.
And so before I read this section, I'm going to read you my note,
which is just a summary of this section.
I think hearing it beforehand will help you.
It says he was disciplined.
He had an intense desire for fame and glory.
He desires useful information for revenge on Persia.
He is 16.
Around 16 years old, it was a section about to retail.
He wanted to wrote-- this is a quote from a description
of Teddy Roosevelt who also is very similar to Alexander
and that they both, they wanted to struggle.
And they had-- they also forced themselves.
They had internal discipline, but they
had external forces of discipline as a way
to make sure they can make themselves do what they want
to do if that makes sense.
But the note I left myself after reading the section
was the fact that there's a line in one of the biographies
of Teddy Roosevelt that I read.
And it says that Teddy wanted to row in a boat, right?
Row over the roughest waters in the smallest boat
in the hottest sun.
He purposely put himself over and over and over again.
I mean, that book, The River of Doubt,
I did on Teddy Roosevelt.
He's a perfect example of that.
He wanted struggle.
He saw-- he did not avoid discomfort.
He ran towards it.
And the sickness that he winds up and all the stuff
that he goes to on The River of Doubt
winds up contributing to a relatively early death.
I think he died when he was what, 60 or 62, something like that.
That's Founders Number 175, if you don't know him talk about.
It's a fantastic book to read, by the way.
The writing is amazing.
The River of Doubt, I've been giving that as a gift to friends
and they've all loved the book too.
OK, so let's go back to the section
what spawned all these notes I just met.
So at this point in the story, his father's
out conquering other places.
And so he leaves like his teenage son in charge.
And it says on one occasion, some ambassadors
from the King of Persia arrived in Macedonia.
And since Philip was absent, Alexander
received them in his place.
This is what I meant about he constantly
sought out useful information.
He talked freely with them and quite won them over,
not only by the friendliness of his manner,
but also because he did not trouble them
with any childish or trivial inquiries.
He questioned them about the distances they had traveled,
the nature of their journey, and the character of their king,
his experience in war, and the military strength,
and prowess of the Persians.
Three years later, are thereabouts, maybe three to five years
later after this conversation, he's
going to use that information and he's
going to overthrow and attack them.
And so while this is happening, Philip's
having a lot of great victories.
He's becoming more famous, more powerful, richer.
Alexander does not like that, because he desires for--
he wants the fame and glory for himself, right?
Whenever he heard that Philip had captured some famous city
or one in overwhelming victory,
Alexander would show no pleasure at the news.
But he would declare to his friends,
my father will forstall me in everything.
There will be nothing great or spectacular for you and me
to show the world.
He cared nothing for pleasure or wealth,
but only for deeds of valor and glory.
And this is why he believed that the more he received
from his father, the less would be left for him to conquer.
And this is a crazy sentence as I said.
So every success that was gained by Macedonia
inspired in Alexander the dread that another opportunity
for action had been squandered on his father.
He had no desire to inherit a kingdom which
offered him riches, luxuries, and the pleasures
of the senses.
His choice was a life of struggle, of wars,
and of unrelenting ambition.
And so this is the section where I met
that he also had external-- he was extremely self-discipline,
but he also had external forces of discipline.
So it says a great number of nurses, pedagogs, and teachers
were appointed to take part in his upbringing.
So I had to look up-- there's a bunch of words in this book
that I came across, I had no idea what they meant.
That's one of them.
So it says a pedagog is a teacher, especially a strict one.
And so he has this guy named Leonidas.
says he will.
who was one of his pedagogues.
So it says they're all appointed to take part
in his upbringing, but the man who supervised them all,
meaning all his teachers, was Leonidas,
who was a severe disciplinarian.
So then Philip comes back, and there is a story.
If you read it, if I've watched documentaries
on Alexander before, this story then,
about tell you comes up over and over again.
It's a story about Alexander breaking in a wild horse.
And it's really the reason I'm reading this to you
is because the realization, he's gonna do this right
in front of his dad, the realization of who his son is
or who his son could be by Philip.
'Cause again, Philip's not, he's very smart.
Dan Carlin makes that point in that podcast.
Like this is not a dumb person by any means.
So it says the king went down to watch this horse
and came to the conclusion that the horse was too wild
and quite unmanageable.
So Philip orders the horse to be let away,
but Alexander remarked, what a horse they were losing.
And all because they don't know how to handle him
or dare not to try.
Philip asked him, "Are you finding fault
with your elders because you think you know more
than they do, or can you manage a horse better?
At least I can manage this one better."
Retorted Alexander.
So as far as I go, "Okay, go ahead and try."
And so they're watching them and he looks
to be very dangerous to get thrown off.
He could be stomped, whatever he says.
I'm skipping over him breaking in the horse.
We're gonna get to the punchline here.
At first, Alexander and his friends held their breath
and looked on in the agony of suspense
until they saw Alexander reach the end of his gallop,
turn in full control and ride back,
try and fit and exulting into success.
His father wept for joy.
And when Alexander had dismounted, he kissed him and said,
"My boy, you must find a kingdom big enough
for your ambitions.
Macedonia is too small for you."
And so he learned something about his son.
He's like, "I cannot just bully him
into just doing whatever I want him to do.
I have to persuade and I have to reason with them."
Philip had noticed that his son was self-willed
and that while it was very difficult to influence him by force,
he could easily be guided towards his duty
by an appeal to reason.
And he therefore made a point of trying
to persuade the boy, rather than giving firm orders.
Besides this, he considered that the task of training
and educating his son was too important
to be entrusted to the ordinary run of teachers.
Now this is gonna be a weird thought for you.
So while I'm reading this, like a week or two ago,
maybe longer, a listener sent me a podcast.
It's the knowledge project episode with Mark and Dries
and it just came out.
And he said, "Listen to the last 10 minutes of this.
It sounds exactly what you're doing."
And in the last 10 minutes, Mark and Dries
was talking about, you know, he's read hundreds of biographies.
He's a devotee of history.
And he talks about building mental models of great people.
And some of these people are still alive.
So he's like, "I have, this is Mark talking."
Mark's like, "I have a mental model of Mark and Dries."
I have a mental model of Elon Musk.
I have a mental model of Peter Till.
He's a mental model of all these people.
And by reading about them, by listening to him speak,
in some cases, knowing them, he's able to,
when he's presented with a decision,
he has such an interesting way to put this.
He says he stress-tests his ideas.
Do you like the scope of the history of entrepreneurship?
And so that's why I think to listen or send.
So hey, listen to the last 10 minutes.
It sounds like what we're doing in the podcast.
Where he's able, okay, I'm presented a decision
in my life and my business.
What would Elon Musk say?
What would Charlie Munger say?
What would Edwin Lans say?
What would Steve Jobs say?
And he has all these different mental models.
As a way to help him make sure that he's making
the right decision, which obviously Mark's brilliant.
I was like, "Of course, he's gonna come up with that."
And say it explicitly, even if we're trying,
we say so implicitly, right?
That's exactly what's happening.
But also, I listen to the whole episode,
'cause anytime Mark's, I get a chance to listen
to Mark's speak, I try to.
And he brings up the fact that like, they're like,
"Oh, he's asked the question something."
Oh, like, how do you, you know,
fix our broken educational system?
And he's just like, "You don't."
Like, that system's never gonna be fixed.
There is no reform.
Like, you have to build something new in its place.
And I sounded like to me, at least when I listened
to this part two times so far,
that he is a six-year-old child,
and that he wants some form of like,
homeschooling or your own curriculum.
And that's exactly what Philip realizes here.
He says, "Listen, besides that,
he considered the task of training and educating his son
was too important to be entrusted
to the ordinary run of teachers."
And unfortunately, Mark goes into details
about what his theory on why this has occurred,
but like, that's the description of our education system.
And so I think Mark's solution is very similar
to Philip's solution, although as if Philip's solutions
in the extreme, one of my favorite things
that I learned about Alexander is the fact
that his private tutor was Aristotle.
That is crazy to me.
So Philip sent for Aristotle, the most famous
and learned of the philosophers of the time,
and rewarded him with the generosity
that his reputation deserved.
And so the idea of setting up your child
or whatever with a private tutor,
that's out of reach for most of humanity, right?
But if you are rich or if you are wealthy,
like, is there something better
that you could actually spend your money on
in the education of your child?
And there is very low cost, almost even free version
of this, as you can actually curate
all the abundant educational resources
that the internet provides.
But there is something to be said about purchasing access
to the greatest minds, because there's weird examples
that come up over and over in these books.
So I think of Dr. Seuss as an example of this,
Sidney Harmon, who I just did on episode number 229,
Michael Bloomberg on episode 228.
They're all, and there's a much more examples in the books,
but they talk about, they're like, I learn more
from this one person in 10 minutes
than I learned in the previous 10 years.
And that sounds so crazy, but it's not.
And you know it's not, because people,
people that don't know each other
lived in different times, worked in different industries,
all talk about having an experience
of being guided by somebody
that has just a fundamental understanding
of what they're trying to learn.
And they can convey key insights
in a very short amount of time.
But I also had this experience too,
because a long time ago, so I went,
I told the story before, but when I was in college,
I was in the pilot entrepreneurship program.
So the very first year, this was like 15 years ago,
something like that.
No, maybe more.
And you know, the last two years,
you're in the entrepreneurship program,
it's like 300 people in the program,
and a lot of it, like anybody else has told you,
like Charlie Munger-Won Buffet talks about the quality
of business schools, I don't know.
But what struck me is the fact that there was a guy,
he was an entrepreneur, he was donating a building.
So I think he was going to donate,
I think he was building a building at the time
for like $3 or $5 million, some number like that.
And he's like, I have one prerequisite attached to this money.
And he's like, I wanna talk to your entrepreneurship students
before I give you the money.
And so he gives like a 30, 40 minute talk,
and then he just lets us light him up
with as many questions as we want.
And I learned more from that guy in one hour
than I did in two years.
And it was just basic, the common sense of an entrepreneur.
He started a company.
His company was, they used to call tires plus.
It's like these places where they'll change your tires,
but they do like basic stuff like oil changes.
And you know, they're not like full mechanics,
but they do like basic maintenance on your car.
And he told us an entire story of like,
how he got the idea, how he expanded,
how he picked the right locations,
just very useful information.
And then he told us a story about the way he sold the company
is he wind up being the largest customer
for Bridgestone tires.
And so Bridgestone was just a giant company.
And now because his other,
because this guy's, I don't remember his name.
He's, because his company grew so large,
when such a large percentage of the tires
that Bridgestone sold to retail businesses, they had to buy him.
And like, if this guy chooses to say,
what if he goes with, you know,
I don't know, other tire brand, Toyota tire, whatever.
Like that, that's too big.
We have to, we have to buy your company.
And so he was forbidden to tell us like the amount,
but he said, hey, you know, hypothetically,
this is what we're doing in sales.
And you know, in this industry,
a good purchase price would be whatever, seven percent
or 10 percent or whatever it was.
But I remember doing the math
and it was something like 40 or 50 or $60 million
or something like that.
So anyways, I guess the point is that learning
and education is non-linear.
And so it's very difficult to design a system
where you can actually optimize for the benefit
of, you know, the mass.
And I just highly recommend listening to, to that podcast.
Not only his, Mark and Jason's thoughts
on building mental models, which comes towards the end,
but also his opinions on the education system.
I thought we're, we're interesting and useful.
Let's go back to this.
So Aristotle's now tutoring Alexander.
It says it seems clear that Alexander was instructed
by his teacher not only in the principles of ethics
and politics, but also those secret
and more esoteric studies, which philosophers do not
impart to the general run of students,
but only by word of mouth to a select circle
of the initiated.
Some years later, now this is very fascinating.
I'm never gonna get through this book
if I keep taking these tangents, but this is very fascinating.
So it's saying, okay, Aristotle has like one set of curriculum
that's public available for everybody else.
And then he's got some other stuff
that's only for a select circle.
So this is very similar to why how many autobiographies
have you and I gone over on this podcast?
A ton, I don't know, 100, it's a large number.
They're not writing no entrepreneur rights biography
in the middle of his career, his or her career.
They wait till the end.
And so they're teaching, you know,
the main theme of this podcast is the fact
that the best founders started themselves as teachers.
Go back to that founder of Costco, Jim Synagogue.
He's like the leader of the company.
That means if you're not spending
as the leader of the company, as the founder, as the CEO,
if you're not spending 90% of your time teaching,
you're not doing your job.
It's insane how many of these founders
talk about themselves as teachers,
but they're only teaching people inside their company.
You have to wait.
You can download Sam Walton's best ideas
for building company, Phil Nights,
all these other people's best ideas,
but you have to wait till their end.
They write these books either when they know they're dying,
Ingvar Camperod, and the list goes on and on.
They have founder of IKEA.
They wait till they're older.
They're like 70, 80, whatever the case is.
We just did this with Sidney Harmon, right?
He was 80, 80, 80 years old when he wrote that book
that I just did the Dunkin' Donuts guy.
He waited till he's 84.
He was offered to write a biography back in the 1960s.
It's like, nope, I'm gonna wait till I'm 84.
And Steve Jobs picked up on this.
This is a quote that I repeat over and over again
to think about this, because there's a lot of people saying,
like a lot of people will publicize
and help use some information to other entrepreneurs,
But you know that there's--
They're saving their best stuff for themselves because they don't want them why because they
don't want to produce more competitors.
And so Steve was learning this because he's doing this extensive when he's trying to help
grow Pixar.
He's in this extensive study of the movie industry of animation.
And so he talks about this.
He says, "Listen, this is a direct quote from Steve.
I love this guy."
I miss him so much.
You can't go to the library and find a book titled "The Business Model for Animation,"
Steve explained.
The reason you can is because there's only been one company, Disney, that's ever done
it well and they're not interested in telling the world how lucrative it is.
And so we see, that's just, in my opinion, constant of human nature, we see Aristotle doing
the same thing 2,300 years ago.
He's like, "Listen, I got a lot of stuff that I can teach you.
The more esoteric, right?
It's only going to be kept with us, and so obviously he's being paid very anxiously.
As he should be, I think teachers should, I think teachers should make a ton of money.
And I think with the internet, you're clearly seeing the best teachers in the world who
will make, I think it was a Chimoff Pala hapatia.
He said that teachers, in his opinion, teachers are going to be paid like athletes.
That you're going to see teachers making $30 million a year, whatever the case is, over
the internet, obviously.
So it says, esoteric studies with philosophies that do not impart to the general run of students,
but only by word of mouth to a select circle of the initiated.
Some years later, Alexander learned that Aristotle had published some of these conversations
they're having, that deal with these esoteric matters, and he wrote to him in blunt language
and took him to task for the sake of the prestige of philosophy.
This was the text of his letter.
So Aristotle's pissed.
He's like, "You're telling other people where you told me, 'Shut up,' Aristotle, greetings.
You have not done well to write down and publish those doctrines, you taught me by word
of mouth.
It's an advantage."
This is why.
This is wild.
Because what Alexander's picking up here is exactly what Steve Jobs realized about Disney.
He's like, "You're telling everybody what you taught me."
And then why is he mad about that?
That's what Alexander says.
What advantage shall I have over other men if these theories in which I've been trained
are to be made common property?
I would rather excel the rest of mankind in my knowledge of what is best than in the extent
of my power.
Farewell.
So that's a play way of saying, "Shut up," right?
This is another example.
I'm still on the same page.
This is crazy.
And that's what I've realized about this book.
It's like a feast in famine, where there's some pages where I can't stop highlighting and
taking notes.
And then there's an entire chapter where I have nothing.
It's not an easy book to read by any means.
Even though I thought, when I picked up, I was like, "Oh, 150 pages."
What I thought of is like, that's 150 page biography of Alexander.
This is going to be like that 190 page biography of Churchill.
It's really not.
He worked for it.
So this is really a reminder, it's like, you've got to read all the time.
And so before I read this to you, I want to read, you know, let's go back to Grandpa Charlie.
What do Grandpa Charlie Margaret tell us?
In my whole life, I have known no wise people over a broad subject area who didn't read
all the time.
None.
Zero.
And the great thing is, I think now with the invention of podcasts and audiobooks, the
fact that you can read.
I was just listening to an interview with Tim Urban, the writer of "Wait But Why."
You know, that guy reads a ton and does a lot of research for his blog, but he's like,
audiobooks has been the best invention for him because he's like, "I'll go to the store."
Right?
I have to walk to the store, get my groceries, come back.
I just read, you know, 30 minutes.
If you read 30, he does this math where if you can read 30 minutes a day, you'll read
a thousand books in 20 years or 40 years.
I forgot.
Basically over your lifetime, you can read a thousand books, right?
And he's like, "I'm standing in line with TSA.
I'm reading.
I'm on this boring plane ride.
I'm reading."
And his method, his audiobooks, but again, physical books, whatever, you just have to read
all time.
Alexander was also devoted by nature to all kinds of learning and was a lover of books.
He regarded the Iliad as a handbook of the Art of War and took it with him on his campaign.
This is crazy.
The copy of the Iliad he had was annotated by Aristotle.
This became known as his casket copy, I'm not sure what that means, and which he always
kept under his pillow with his dagger.
And his campaigns had taken him far into the interior of Asia, and he could find no more
books.
He ordered his treasurer to send him some.
Send him some.
Oh, and then it moves in a different direction, so we're now skipping over his love of reading
into the fact that he was engaged in war, even when he was 16 years old.
This is something he's very happy because Philips out gone.
So they think, "Oh, Philips not there.
We're going to take over, you know, we're going to attack and we're going to make quick
work of his son that just doesn't happen."
So he was only 16 years old, he defeated the Medea who had risen in revolt, captured
their, who had risen in revolt, Alexander captured their city, drove out its inhabitants
and established the colony of Greeks, assembled from various regions, and named it Alexander
Heropolis.
Because of these achievements, Philip became extravagantly fond of his son, so much so that
he took pleasure in hearing the Macedonian speak of Alexander as the king and Philip as
their general.
Not long after this, Philip is assassinated, there is some rumors, and Dan Carlin goes into
the way more detail on his podcast, I highly recommend you, listen to it, if you're interested
in this kind of stuff, that no one really knows who, they know who assassinated Philip, it
was who actually stabbed him.
But there is rumors that Alexander and his mother were the ones that initiated the plot.
And so in that podcast, Dan Carlin talks about, he's like, this is who, and he always talks
about the ancient world is so foreign and bizarre to the world we live in, so it's hard
to understand that.
So he uses the analogy of the JFK assassination.
And so Dan uses this metaphor, he's like, listen to understand how bizarre this sequence
of events is.
Imagine if Jackie is the one that convinced Lee Harvey Oswald to kill her husband.
And then the added twist is that Lee Harvey Oswald and JFK were lovers.
And so Dan's point was like, that is what many people believe happened here.
Okay, so at the beginning of all these chapters, they have like a brief description of what
is about to occur in this chapter, I'm just going to give you this overview.
So it says, as the new king of Macedonia, the 20 year old Alexander immediately sets
out reestablishing his father's control over Greece, he does encounter resistance, notably
from one, from one, one of the key powers in Greece, which he swiftly defeats, destroying
the city, and selling almost all the surviving citizens in slavery.
Athens is then quick to surrender.
Only Sparta, the major remaining power in Greece, maintains its independence from Macedonia
rule.
So then it goes into detail, like I said earlier, I'm skipping over the battle parts,
we're really just trying to figure who Alexander was, right, as a person.
And so he winds up stumbling, like he's going around and conquering all these areas,
right?
But there's also many examples in the book where he seeks out interesting people and he wants
to meet them.
And so there's a bunch of interesting supporting characters.
And so one of these is this guy named Diogenes, which is he's one of the founders of the
cynic philosophy.
And so I want to read a section to you because I love that there's all these weird independent
characters and all these biographies, and some of them just stick in my mind.
So this guy, for whatever reason, or in reading this section, there's something that happens
in George Lucas' biography that popped my mind.
So it says, many of the Greek statesmen and philosophers visited Alexander to offer
their congratulations, and he had hoped that Diogenes would do the same, right?
So come and give me adulation.
He's not going to do that, right?
So it says, however, since he paid no attention, whatever to Alexander, he continued to live
at leisure in the suburb of Corinth.
So if all these people are keeping track of these current events going and trying to seek
favorite Alexander, this guy's off in the cut just doing his own living his own life.
He's kind of ignoring.
He's almost like muted the world as the way to think about that.
And so he's like, I'm not even paying attention to Alexander.
And so it says, so this peaked Alexander's interest.
Alexander went in person to see him and found him basking in the sun.
So the legend here is like he stumbles upon him, he's just sunbathing naked.
And it says, when he saw so many people approaching him, Diogenes raised himself a little
on the elbow and fixed his gaze upon Alexander.
The king greeted him and inquired whether he could do anything for him.
Yes, replied the philosopher.
You can stand a little to one side out of my son.
Alexander said to have been greatly impressed by this answer and full of admiration for
the hotor and independence of mine of a man who could look down on him with such condescension.
That is a weird response, right?
So much so that he remarked to his followers as they were leaving because they were laughing
at the fact that in mocking the philosopher, right?
Alexander had a different point of view.
He says, you may say what you like, but if I were not Alexander, I would be Diogenes.
And so one of my favorite books that I've ever read for the podcast, I think it's episode
number 35.
It's George Lucas' biography.
I will definitely reread it in the future and make another podcast on it.
And what I found really fascinating about that is that there's a collection when they're
in their early 30s, right?
This is maybe the late 20s.
So there's a group that is not yet famous, that will be famous, and they all know each other
and hang out.
So you got George Lucas, Francis Ford Coppola, Stephen Spielberg, Martin Scressace and
Brian Dupalma.
And so the book covers who these people were before they became famous and successful
with Star Wars and Jaws and the Godfather and all these other movies, right?
And so a lot of them did not like it at the time.
I think it was in the early 60s.
I can't remember the time, the decade, exactly.
But they didn't like the standard way that the movie industry was set up.
And they were looking for a different path in.
And so this is, I'm going to relate this to, you know, just have this guide.
There's like these independent characters that are kind of, they just set up their life
the way they want to do it regardless of how other people, or other people tell them
they should or the industry thinks you should.
And I just find these people extremely admirable.
I like these people just like Alexander like Diochini's, right?
And so this is the guy named George.
John Cordy and John Cordy is essentially like the Blueprints, the business model and
the modus operandi that George Lucas is going to copy and then take to an extreme level,
right?
And so it says, I'm going to quote from George Lucas's book for a minute, sitting next
to him was 31 year old independent filmmaker from Northern California named John Cordy.
And it says while Cordy spoke eloquently on the topic at hand, it was when he digressed
into the details of his filmmaking that Lucas really took an interest.
This is the Blueprint Lucas is going to follow.
For the past three years, Cordy had been running his own filmmaking facility out of his
barn at Stinson Beach, which is a small town just north of San Francisco.
George Lucas winds up setting up shop in a similar area because he's like, "I don't want
to be an L.A.
Everybody tell me I have to be an L.A.
I'm not going to do that.
That's where Bill Skywalker ran.
So anyways, this is many years in the future."
He had, uh, Cordy had privately raised $100,000 for his movie by hitting up friends, colleagues
and even actors for the money.
He shot the movie locally, then edited it on his own equipment.
This is all the stuff that George Lucas is going to do.
At the film's premiere at the Museum of Modern Art in San Francisco, it received a lengthy
standing ovation and Hollywood executives fell over themselves scrambling to distribute
it and distribute the movie and recruit Cordy.
But now we see this fierce independence of mine in Cordy.
We just saw it in Diodyogenes.
We see it in Henry Singleton.
We see it in Claude Shannon.
We see this over and over again.
And so it says, "But Cordy was having none of it.
From what I saw of Hollywood, they can keep it.
I would rather work for myself.
In Hollywood, you have a producer breathing down your neck.
Hollywood is dying slowly.
Here in Northern California, I am happier working with less money.
The risk of failure is far less.
We can complete a film in a year, getting the results that we want."
And so Coppola and Lucas are realizing this guy nails it.
This is exactly what we should do.
Coppola and Lucas had seen the future in Cordy's barn on the beach.
They were going to build their own cinematic community somewhere.
If you can do it, he had told Cordy enthusiastically we can.
And this is the punchline.
This is exactly what they had in mind for themselves.
Cordy inspired us both.
He was a real innovator.
And so there's no books written on John Cordy.
You know, there's no biographies.
Most people don't know who he is.
But if you read a ton of biographies, you come across these just independent, really interesting
characters that can then influence your thinking.
Just like Cordy influenced George Lucas and Francis for Coppola's thinking, he's definitely
influenced mine.
And tons of other people that have discovered his way of thinking.
And so the book goes into quite, I would say, half the book about this fight that he's
having with trying to revenge what's it called, Persia, like the 150, the battle of Persia
that happened 150 years before he was born.
Imagine being the leader of Persia and it's like, "Wait a minute guy, you're seeking
retribution for something that happened 125 years before he was born."
So he's going to wind up overthrowing Darius.
This part is just incredible because this is what I know to another of myself.
This is incredible, read this part slowly.
The Persian king doesn't want to hear the truth.
And so there's been all these like skirmishes, but Darius knows that Alexander is coming
for him, right?
And so Darius is asking in vice from this guy who has no reason to lie to him because
he doesn't like Alexander.
So it says Darius turned to the Athenian.
His name's, I don't know how to pronounce this, so I'm going to call him Chad.
So he turned to the Athenian Chad who was an experienced soldier with a grudge against
Alexander because of his exile.
It was on Alexander's command that he had been expelled from Athens.
And he proceeded to ask whether in his opinion, so Darius is asking Chad his opinion, if he
was well enough equipped to crush his enemy with no thought for his own circumstances and
the vanity of royalty, Chad answered, "Perhaps you do not want to be told the truth, and yet,
if I do not tell it to you now, it will serve no purpose to admit it at another time."
This magnificent army, this conglomeration of so many nations, can strike terror into
your neighbors.
He's describing Darius' army.
It gleams with purple and gold.
It is resplendent with armor and an opulence so great that those who have not witnessed it
simply cannot conceive of it.
Now he's going to compare where you have Darius to what Alexander has.
This is not going to go well for you, Darius.
The Macedonian line is certainly coarse and ineligent, so let's think about that.
Yes, another weird thought for you.
I was struck.
I cannot stop thinking about the Dunkin' Donuts book.
And the fact that the arrogance of his son, you have, so you have, what is Chad telling
us?
Like your army's great number, you're wearing fancy clothes, you have gold and all this
other stuff, and you're going up against this Macedonia.
And they're coarse and they're ineligent, right?
But they're skilled.
That's the difference here.
So you have this 25 year old son of the Dunkin' Donuts founder who grew up in a wealthy house,
right?
Because his dad, his dad, if you haven't listened to that episode, the guy that found the Dunkin'
Donuts writes the book when he's 84 years old, okay?
He's been working full time since he was 14.
He has an eighth grade education and had to drop out because his dad's business and the
depression went under.
And so he was forced to learn how to make money from a young age.
Every dollar he made had to turn, in turn, be given to support his family.
So over the course, so you take that set of skills that he started at 14.
Now, fast forward, he's 50 years old.
He's been making a ton of money for a long time because he's a really good entrepreneur.
But he only has an eighth grade education.
His son grows up in an environment opposite that he grew up in, right?
He grows up, his dad's making money.
His dad has enough prestige that he can get into Harvard Business School.
Then he comes out at 25 years old, right?
So now you have a 25 year old with a Harvard Business School education and no experience
at all, making money.
And then you have a 50 year old entrepreneur with almost 40 years of experience.
He's built two amazing businesses.
One of them went public, right, which is Dunkin' Donuts.
That 50 year old that has all that experience is not twice as smart as a 25 year old no experience.
He's 1,000 times in terms of entrepreneurship, right?
He's 1,000 times smarter.
And then you, we are perceived as you read that book.
You're preceded to just hear the story of this arrogant kid.
Being advised by his dad, right, your dad loves you more than anybody else in the world.
He has all this experience.
He's telling you, hey, don't do that.
This is a bad idea.
This is why you shouldn't do that.
But he defers to his son.
He's like, you shouldn't do this.
His dad goes, okay, thanks, or his son goes, thanks for the advice, dad.
I'm going to do the opposite.
And then he proceeds to run the company into the ground where they literally had to find
a white knight to be bought out.
Or else Dunkin' Donuts is going to have a hostile takeover.
And his son was like, he even said it in quotation marks that you and your dad, you and
your crew, like your executives are not sophisticated.
That is a line in the book.
That is insane.
And he said it's not sophisticated because you don't do reports and sit in meetings like
we do.
You can't believe that this is true.
You just cannot, like, you're reading that book and like, what the hell?
I think if you listen to that podcast, I start dropping f-bombs because I'm so, I'm
the incredulous at the arrogance, the undeserved arrogance that's coming from his son.
And the focus on the absolutely wrong thing.
So we're going to see that here.
So it says, okay, you guys are great, you're in gold, okay, that's nice.
The Macedonian line is certainly coarse and inelegant.
But it protects behind its shields and lances, immovable wedges of tough, densely packed soldiers.
The Macedonians call it a failings, an infantry column that holds its ground.
They stand manned, next to man, arms interlocked with arms.
They wait eagerly for their commander's signal and they are trained to follow the standards
and not break ranks.
To a man, they obey their order.
So what is he saying?
You may think they're elegant, you may think they're coarse, but they're disciplined and
they're skilled and they're not going down without a fight.
And from top to bottom, this organization is much more formidable than yours.
The commander says the common soldier is no less skilled than the officer.
And don't think what motivates them is desire for gold and silver.
This is exactly what the Dunkin' Dona says.
Until now such strict discipline has been due to poverty's schooling, that is a crazy
line.
He's like, you guys have been rich for generations, these guys grew up poor.
And their discipline is due to the education that you learn from poverty.
When they are tired, the earth is their bed.
They don't need the fancy tents that you guys have and all the gold and all this other
stuff.
They are and the fancy food.
They are satisfied with food.
They can prepare why they work.
Their sleeping time is of shorter duration than the darkness.
So this goes on for some while.
Imagine if you're some spoiled, rich king.
You're not going to like people talking to you like that, right?
Which is exactly the opposite of what we just learned from Alexander, Dionysius or whatever
the guy's name is.
I can't pronounce it.
He was like, get out of my son and he thought it was funny.
What you need is strength like theirs.
You must look for help in the land that produced those men.
He's talking about the unique environment molded them like a sculpture.
Send off that silver and gold that you have and hire soldiers.
That is a hell.
You don't have soldiers.
You have an army.
And so Darius had Chad dragged off and executed.
And he did this at a time when Chad was making very useful recommendations.
And so the lesson there that's tied to us, like we're obviously not going to be conquering
the world but I can't help but think of what the founder of UPS told us.
He's like, I don't want to get my information from my executives.
Their incentives is to give me good information, to flatter me so they can make more money.
He's like, when I'm driving around the city and I see a UPS driver at truck, I immediately
stop and I get out and I talk to the driver because that driver is the end point.
He's the connection to my customer.
He's the foundation upon which my empire rests.
He will tell me the truth, the day-to-day of like, what do we need to do better?
What are we doing well?
What can we improve at?
My executives will not.
So you need people that will tell you the truth.
A main, like I would say, the supporting character in this story is difficulty.
He talks about the importance of difficulty, but, again, he seeks things out.
And I'm just going to give you one example.
The fact that it is difficult makes it more important.
That is something Alexander believed.
Once he arrived to the city, Alexander gave orders for the siege to be put together, only
to be advised by his engineers that the steepness of the hill would make it impossible to take
the city by force.
Alexander believed that these difficulties actually made the capture of the city even more
essential, as such unexpected success would strike terrible fear into his enemies, whereas
failure would bring disgrace upon him.
And then, you know, some of his, not some, almost all of his behaviors is unapologetically
extreme because he believed, and like he was the descendant of the God, he believed
his fate was to rule the entire world.
So you know, this is why he's talked about, you know, 2,500 years later, what are the
cases?
The scope of his ambition is just, it's limitless.
So he's talking to the priest, he says, the oldest of the priests, Alexander proceeded
to ask whether he was fated to rule over the entire world.
The priest answered that he was going to rule all over all of the earth, and that he added,
the priest added, that Alexander would remain undefeated until he went to join the gods.
And then this is a hell of a line.
A hell of a line considering that this was written 2,000 years ago, and it's a description
of Alexander but really of human nature, fortune generally makes those whom she has compelled
to put their trust in her alone more thirsty for glory than capable of coping with it.
Alexander was more thirsty for glory than capable of coping with it.
I think the lesson for us there, like be careful what you wish for.
Humans are terrible, terrible at predicting what they actually want.
Another trait for you here, it's interesting, my wife asked me this morning, she's like,
what did you learn from Alexander?
Alexander's great, the first thing that came out of my mouth was like, he had a high tolerance
for pain.
And again, that was not, I didn't have that prepared, that's what stumbled out immediately.
This is an example of that.
For besides all of his other hardships, he had recently been wounded below the knee by
an arrow, which had splintered his shinbone.
On another occasion, he had received such a violent blow on the neck from a stone that
his vision became clouded.
In spite of all this, he continued to expose himself unsparingly to danger.
He had crossed the river, routed some other tribe, and pursued them for 12 miles.
Even though all the while, he was suffering from an attack of dysentery.
And so this is very closely in the book, this is his apex.
This is a description of the chapter before you read the chapter.
So it says, "Yet, even though Alexander is advised that these lands are written, he's
in India at the point."
He's trying to overtake India.
Yet, even though Alexander is advised that these lands are rich and that the victory should
be within his grasp, his men are exhausted.
Their spirits are broken at last by hardships of the monsoon.
Led by an old and respected general, they refuse to continue.
Having come so close to complete domination of India, Alexander is forced to give in to
his men and begins his retreat.
So that is as far as he gets this apex shortly after is when he's going to die.
There's a line in this book that Jeff Bezos would be extremely proud of, terrified by
the unbelievable boldness of the Macedonian.
So bold.
I can't tell you how many times he uses that.
If you've read Jeff's shareholder letters, it might be his favorite word.
So he's having this great war with this, another, almost like the version of Alexander
if he was born in India.
And it's just remarkable.
Look at how Alexander treats and respects genuine excellence, even in an enemy.
This part was really surprising to me, this guy is like hell of a, there's all these
kinds of crazy stories in the book.
But this guy is fighting.
The guy that Alexander's about to defeat has like an army of elephant.
He shows up to battles like 85 elephants and like 30,000 troops and all kinds of crazy
things.
And Alexander's like just defeated him.
It looks like the guy's going to die.
So Alexander's talking to him.
He's like, why didn't you give up essentially what he's saying?
He's like, you know who I am.
You've heard my, now he's a decade into his conquest.
Like, why would you even attempt to fight me and then die for this?
And so let's pick up this conversation, which is just remarkable.
What folly forced you knowing as you did the fame of my achievements to try the fortunes
of war?
Since you were asked, replied porous, I shall answer you with the frankness your inquiry
has granted me.
And again, there's always another you, you know, you're not the only, I love, let me
go back to Tim Urban.
One of my favorite ideas I learned from him is like, he's like when I'm writing a post,
I just envision a hundred thousand other Tim's.
He's like, there's people out there, various, we have similar traits, we're interested
in the same things.
And so what Alexander realizes, like this is another me.
And so porous says, I shall answer you with the frankness your inquiry has granted me.
I did not think there was anyone stronger than I, though I knew my own strength.
I had not yet tested yours.
And now the outcome of the war has shown you to be the stronger.
Alexander questioned him further, asking his opinion on what his victor should do with
him.
But this day tells you to do said porous, the day on which you have discovered how transitory
good fortune is.
Porous's advice did him more good than please would have done.
His greatness of spirit, meaning porous, was not crowd or broken even in adversity.
So Alexander's like, this is another me.
And when two people realize, okay, this is another me, I always use the example I've gone
back and I was obsessed with my good Jordan when I was a kid.
And I've read a lot about Kobe where I listen to him speak because his mindset, right?
I wasn't even a Laker fan, but I really enjoyed his mindset.
And he realized that too because there's a ton of examples when Jordan becomes an older
brother to Kobe because he realizes like Kobe won't back down.
So Phil Jackson, there's two stories I want to tell you real quick.
Phil Jackson talks about, hey, he's currently coaching Kobe at this time.
He's like, hey, Michael, come by.
The practice.
If you got free time, and so he's talking, he's kind of trying to test Kobe Bryant.
He's like, oh, you can't guard me.
They're talking back and forth.
And at this time, people were afraid of Michael and Kobe's like, you can't guard me.
And so they go back and forth.
And he's like, well, I got shoes.
We can do this right now.
And so they wound up leaving, Michael walks away with a modra shot who was also there.
And he turns to him and goes, man, I love that dude.
That dude is a warrior.
And a mod is now interviewing Kobe, this is what I'm watching.
And a mod's like, how old were you when that happened in Kobe's like 21?
And then later on, Kobe tells a story.
He comes in the league.
I think he's like 70.
The first time he plays against Jordan, he's like 18 or 19 years old, something like that.
And you know, it idolized Jordan growing up, copied his moves, studied him.
And so his teammate right before the game's like, hey, you want some advice?
He's like, yeah, what's that?
And he goes, don't look him in the eye.
And Kobe's like, what?
Excuse me?
And so Kobe tells the story's like, well, my teammate didn't realize it's like, I'm
that too.
You can't look me in the eye either.
And that mutual admiration, even if they're competitors, it's like, okay, this is a, this
is a very, this guy thinks like me, this is very similar to me.
It doesn't usually engenders respect.
And it's really the only way to deal with a formidable individual, because a lot of these
formidable individuals, if we've seen time and time again in these books, they'll run
over you.
If they think you're weak or you're going to give in, like they strength, respect, strength.
You cannot.
And Kobe realizes like, I don't want to look at the guy in the eye.
You think I'm going to be able to beat him on the basketball court?
Like, those are ridiculous.
So let me tie this back to what Alexander does, because this is insane.
He just, he just ran over the guy, he almost tried to kill him.
And he's going to wind up recruiting him.
He's like, I want you on my team.
So it says, Porus's advice did more good than please would have done.
His greatness of spirit was not cowder, broken, even in diversity.
And we've seen that Alexander wouldn't cow or break in adversity.
And Alexander felt obliged to treat him not only with mercy, but with respect.
He tended to his wounds just as if Porus had fought on his side.
And when they recovered, contrary to, and when Porus recovered, contrary to everyone's
expectations, I thought he was going to die.
Alexander made him one of his friends.
And shortly afterward, bestowed on him an empire larger than Porus had formally held.
That's insane.
In fact, no trait of Alexander's was more firmly held are enduring than his admiration
for genuine excellence and brilliant achievement.
And so that is what separates.
We talk a lot about the naysayers, the negative people we know of that with Dunkin Donuts guy
last week.
He talks about this.
It's just a part of human nature.
The 10% of people that overachieve have positive mental attitudes.
That right there separates the losers from the winners.
Winners don't go around leaving negative comments about other people winning.
There was no trait of Alexander's more firmly held are enduring than his admiration for
genuine excellence and brilliant achievement.
When a mediocre person is faced with genuine excellence, they retort.
They become negative because they see in themselves everything that they are not.
They're the greatest founders, investors ever.
They do not denigrate the past.
They build upon it.
They go out and seek these people.
Let's read that one more time.
And then now we got to the part where he's facing declining morale and he gives in my opinion
just a remarkable speech.
So it says Macedonian resolve was flagging as the men watched their king pursuing a relentless
campaign that was fraught with hardship and danger.
Remember, I said that supporting Cass in this book is hardship, right?
It's difficulty.
He's embracing it.
This is why I think it's fantastic because he really synthesizes his worldview and
it's the fact that everything that you want is on the other side of discomfort and danger
and uncertainty and terror.
Macedonia resolve was flagging as the men watched their king pursue a relentless campaign
that was fraught with hardship and danger.
In the camp, meetings were taking place where the more moderate among them complained about
their predicament, while others utterly refused to follow any further, even though Alexander
was leading them.
As soon as Alexander heard what was going on, he explained it to Alexander.
going on, and before the disorder and despondency among the soldiers could get any worse, he
called a meeting and gave the following speech.
Now that I see that you, my Macedonians and allies, no longer have the spirit to follow
me into dangers.
I have called you together so that I might either persuade you and forge ahead or let
myself be persuaded to turn back.
If indeed there is some cause for reproach regarding the hardship that you have endured
up to now, or regarding my leadership, taking the opposite path that Darius did earlier,
we didn't want to hear the truth, right?
Or regarding my leadership, it is pointless for me to continue addressing you.
But the result of the hardship that you have endured, you now occupy and then he's listing
all these places that they conquered.
It's like if you were in, it's like if you had, let's say, because I don't know the names
of these things, I'm just going to give you an example of how long this goes on.
Imagine that somebody came and you started conquering like individual states and Americans.
As a result of the hardship, you have endured, you now occupy Louisiana, Maine, Maryland,
Minnesota, Oklahoma, North Dakota, New Mexico, New Hampshire, Tennessee, Utah, Virginia,
Washington, Wisconsin, Wyoming, it just goes on and on.
Why then do you shrink from adding Alabama, Alaska, Arizona, Delaware, Florida, it goes
on and on, and the people's behind are, and the people's beyond like Canada and Mexico,
two year Macedonian empire.
And then he makes the point.
He's like, I don't have any of these limits.
My limit is the entire world.
So he says, as far as I can see, true men need no reward for their labors, aside from
those labors themselves, as long as they have noble consequences.
Nevertheless, if any of you, if anyone should wish to know what limit is set for our campaign,
then let me tell you that it is only the whole of the earth.
The boundaries of this empire will be those that God has laid for the entire world.
And then he ends by summarizing himself.
So stand firm for it is toil and danger that lead to glorious achievements, while pleasure
lies in a life of courage and in a death that brings undying fame.
And that is where I'll leave it for the full story by the book.
If you buy the book using the links in the show notes, you'll be supporting the podcast
at the same time.
If you want to buy a friend, a gift subscription to founders, that link is below as well.
That is 232 books down 1,000 to go, and I'll talk to you again soon.
Podcast Summary
Key Points:
Alexander lived for 32 years and ruled for 12 years, demonstrating exceptional longevity and leadership.
He possessed extraordinary courage, intelligence, and a relentless drive for glory, often acting with fearless determination in uncertain situations.
Alexander combined physical and mental discipline, leading from the front, enduring extreme conditions, and maintaining high morale through personal bravery and strategic vision.
Summary:
Alexander the Great was a remarkably driven and fearless leader who lived only 32 years, yet left an enduring legacy. Born into a militarized Macedonian kingdom, he displayed early signs of self-discipline, ambition, and a hunger for glory, even as a teenager. Under his father Philip’s guidance, Alexander was educated by the renowned philosopher Aristotle, gaining not only ethical and political wisdom but also access to esoteric knowledge reserved for a select few.
This deep intellectual foundation, combined with his unrelenting willpower, enabled him to lead vast military campaigns across Asia and Africa, conquering empires and expanding the known world. Despite being physically and emotionally vulnerable—experiencing wounds, alcoholism, and personal tragedy—he remained committed to action, speed, and decisive leadership. His belief in divine lineage and heroic destiny fueled his boldness, while his refusal to accept defeat or delay proved pivotal in victories.
Though criticized for arrogance and excess, Alexander demonstrated self-awareness and a willingness to repent. His story resonates across time because it embodies the tension between ambition and self-destruction, highlighting how extreme drive—when channeled with discipline and purpose—can lead to greatness. Modern reflections on entrepreneurship, leadership, and education echo Alexander’s journey: the value of learning from rare mentors, the power of endurance, and the danger of arrogance.
Ultimately, Alexander’s legacy is not just in conquest, but in the enduring human traits of courage, resilience, and relentless pursuit of excellence.
FAQs
Alexander died at the age of 32.
Alexander was handsome, brave, highly intelligent, self-assured, and driven by an insatiable desire for glory and adventure.
Yes, he was skilled with swords and spears, highly knowledgeable about army organization, and led from the front in battle.
He demonstrated fearlessness and used his own courage to boost morale, showing soldiers that they could face danger without losing hope.
Alexander drank heavily, and this is considered one of his weaknesses, possibly contributing to his downfall and eventual death.
He was driven by a desire for glory and revenge, motivated by the Persian wars that had happened 150 years earlier and a belief that he was destined to achieve great things.
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