April 19, 2023

Leonardo Da Vinci (Part 1)


It’s the 1470s Leonardo Da Vinci is hiking alone in the hills of central Italy, when he chances upon an enormous cave. It is unmarked, and there are no signs of human habitation. It is apparently undiscovered.

He later wrote in his journal what he felt at the time.

“Suddenly there arose in me two contrary emotions: Fear and desire. Fear of the threatening dark cave and desire to see whether there were any marvelous things within.”

He stands in front of the cave for a long time, bending back and forth to see if he can maybe make out even a faint outline of something inside, but it’s too dark. He can’t see anything.

He’s got a decision to make. Does he risk going into the cave and seeing what’s inside, or does he continue on with his day?

But he already knows what he’ll decide. Because Leonardo Da Vinci always chooses satisfying his curiosity over everything else. He enters the cave, and the reward for following that curiosity is that he discovers in the walls of the cave a fossilized skeleton of a whale.

The historian Kenneth Clark called Da Vinci the most relentlessly curious man in history. And I have to agree.

When you read enough of these biographies, you start to see certain archetypes, certain types of people. But I think Da Vinci is a one of one. I’ve never seen or read about a mind like his ever anywhere.

You are probably not wired like Da Vinci. That’s okay, I’m not, most people aren’t. I’m not sure anyone is.. But I think anyone can learn how to be more curious by learning about his story.

And curiosity, as it turns out, is a superpower. Da Vinci is widely regarded as one of the greatest artists of all time, if not THE greatest artist of all time. He painted what are probably the two most famous paintings of all time in the Mona Lisa and the Last Supper. His sketch of the Vitruvian man could also probably go on the list of most famous artworks.

He was also a shockingly insightful amateur scientist. When reading through the excellent biography of Da Vinci by Walter Isaacson, I was struck by how often you read the phrase “which wouldn’t be replicated for another 100 years” or 200 years, or even sometimes 300 years. He made observations about physics, biology, engineering, and material sciences that would literally take 100s of years to replicate.

He was also a tinkerer, an amateur inventor who came up with a number of userful inventions, and laid the groundwork for even more.

Steve Jobs said of Da Vinci “He saw beauty in both art and engineering. And his ability to combine them was what made him a genius.”

We hear a lot about the power of standing at the intersection of art and science. But few people actually do it. Da Vinci did, and he did it like no one before or since.

This is an episode about how to actually do it, how to combine art and science to become a great innovator.

So let’s get into it. This is part one on the life of Leonardo Da Vinci. Welcome to How to Take Over the World.

*** Dance Break ***

Leonardo Da Vinci was a bastard. His father was a minor nobleman from Vinci, a small town outside of Florence, and his mother was a 15-year orphan.

Luckily for him, renaissance Italy has been described as a golden age for bastards. In Florence especially, the culture was quite accepting of weirdness generally, and bastards in particular.

In fact I would say that it was weirdly accepting of the practice. At the time of Leonardo’s birth, his father, Pierro, was engaged to be married to a woman from a very prominent Florentine family. And yet when Leonardo was baptized at one day old, the whole Da Vinci family showed up for the baptism, and made a proper party out of it - apparently feeling no guilt or embarrassment.

If nothing else, you would think they would sweep it under the rug for the sake of the poor Florentine girl who Pierro was scheduled to marry in a matter of weeks, but no, they were quite proud of this illegitimate child.

In fact not only was illegitimacy not a problem for Leonardo, I think you can make the case that it helped him.

As I said, Leonardo was very curious, even as a boy. He was extremely bright and his talent as an artist was apparent from a very young age. But today we might call him ADD. He had a lot of trouble focusing, completing tasks, and focusing on anything that did not capture his interest. If he had been a legitimate child of Pierro, he would have been expected to take up his father’s trade as a notary. And for my American listeners, renaissance notaries were not like American notaries today, they were essentially lawyers, it was a prestigious occupation that could make you quite wealthy.

But Leonardo would not have been a good notary, because of his distractibility.

He also would have received a classical education from a young age.

Instead, he was allowed to have a carefree childhood exploring the Tuscan countryside, letting his imagination run wild, and learning by experimentation and observation. The only formal schooling he received was a couple of years in an abacus school, designed to teach young Florentine’s the rudimentary math required to engage in commerce. He also received some informal education. He was of course taught how to read and write and was given a rudimentary education at home.

At twelve years old, he moves from the small town of Vinci to Florence with his father. He later wrote in his journal how much he missed the countryside, the animals and plants that he had come to love, but at the same time he was thrilled by the intellectual scene in Florence.

This is peak renaissance in Florence. It’s an explosion of knowledge, culture, and art. There are a lot of reasons for this. One of the biggest ones is the printing press, which was invented the year Leonardo was born. Information could be disseminated at a fraction of the cost that it had cost to copy books by hand.

Another reason for the renaissance was the fall of Constantinople.

Constantinople had been one of the great centers of Christian learning. It was a cosmopolitan city where people from Europe, Asia, and Africa came together to trade and to learn. For more than a thousand years it had been one of the great cities of the world.

Well when Muslims conquered it in 1453, many Christian scholars decided that they might be better off under Christian rule in Western Europe, so they abandoned the city and came to places like Florence, bringing their knowledge with them - as well as a vast trove of books and manuscripts.

The fall of Constantinople and the invention of the printing press were like two waves in the ocean that crest on top of each other, creating a tidal wave. So the combination of new information with a new way to spread it is a big part of what created the renaissance - which is a complete revolution in everything: you’ve got innovations in science and engineering, in medicine, in art, in commerce, in technology, and more.

And Florence is the epicenter of all of this.

It was the richest city in Europe and one of the great centers of industry and commerce. Its merchants were rich, and they loved to show off their wealth by patronizing the arts.

When Leonardo first came to Florence, he would have heard the whirring and clacking of weavers shops, the hammers and furnaces of goldsmith shops, the bustle of wagons and carts carrying goods, the music of street performers, the shouts and hurried conversations of merchants like the Medicis trading in the markets.

It was the New York City of its time. It was the place where everything was happening commercially and artistically.

Now at first, Leonardo was just living with his father, presumably helping him out with odd jobs and tasks related to the notary business. But his father writes of him at this time that he “never ceased drawing and sculpting.”

So he has this obsession.

And so his father shows some of his drawings to a notable local artist named Andrea del Verrocchio. Verrocchio is very impressed by what he sees and takes the boy on as an apprentice at age 17.

His apprenticeship is interesting because it defies many of the stereotypes that we have about great artists.

First of all, the environment is not self-serious and ponderous. It’s more like a commercial shop than a fine art studio. There is a workroom on the ground floor, open to the street, where they are mass-producing products from easels, kilns, pottery wheels, and metal grinders.

These aren’t artistes, it’s a bunch of lads who are joking around and having a good time - making money, and also exploring their craft together, one-upping each other, competing, and collaborating on how to create better and better art.

It’s an environment that reminds me a lot of silicon valley in the 70s, or Thomas Edison and his It reminds me of silicon valley in the 70s, or of Edison and the traveling telegraph operators of the latter half of the 19th century.

Leonardo found it to be an ideal environment. He later wrote “drawing in company is much better than alone.”

And I think that is true of many pursuits. Perhaps, in the age of remote work, too many of us are doing creative work alone. Maybe it’s not just drawing that is better done in company. Maybe writing, and composing, and graphic design are much better in company than alone.

Now despite the mundane nature of some of his early work, it’s not long before Verrochio notices how gifted Leonardo is.

It’s during this time that he begins pioneering two new approaches. The first is called chiaroscuro, which means light and dark. Essentially, this is the practice of adding black pigments to create shadows. And this allowed Leonardo to much more realistically depict the effect of light and shading on a subject.

The other innovation was something called sfumato, which means smoke.

Leonardo, with his keen power of observation, noticed that in real life, we hardly ever see actual hard lines, but soft lines and shaded contours.

He wrote “your shadows and lights should be blended without lines or borders in the manner of smoke losing itself in the air.”

The best way to understand this is to Google The Baptism of Christ Da Vinci. This is a painting done by Verocchio and Da Vinci together. On the right side you can see John the Baptist, whose body was painted by Verocchio. Look at the leg, it’s painted accurately with lots of details, but you’ll see how it’s painted with hard lines.

Now look at the body of Jesus on the left, which was painted by Da Vinci. Look at the leg, with his use of Sfumato, he has rendered it much more realistically. The leg does not have hard lines, but subtle shading differentiates the various muscles in the leg.

The technique in this painting was so ahead of its time, that supposedly after The Baptism of Christ, Verocchio vowed never to paint again. And he never did another painting commission on his own. Think about that, Verrocchio was a famous painter in his own right with many notable pupils. And he’s only 40, he’s not old. The pupil had so thoroughly outpaced the master that Verrochio could only marvel. He thought that once he had seen a master like Da Vinci, the right thing was to leave the painting to a genius like him.

Now why was Leonardo so focused on these new techniques? He wrote that “The first intention of the painter was to make a flat surface display a body as if modeled and separated from this plane.” In other words, it was to render objects realistically, to make them appear three dimensional on a two dimensional plane.

In that way, Da Vinci was very much the Pixar of his time. Remember, Pixar started out as a technology company focused on the technical problem of rendering 3D images and only later became an animation studio.

Both Da Vinci and Pixar were consumed with how to render three dimensional objects on a two dimensional surface, the only difference was that Pixar’s objects moved.

And like Pixar, Da Vinci wasn’t just pioneering these technical innovations for their own sake, but because they allowed him to communicate more effectively through his art. He could better display movement and emotion and story by painting more realistically.

It’s an interesting paradox that those who are focused on the technical details of their craft are often those who create the most transcendent art.

There is a famous quote from Pablo Picasso “When art critics get together they talk about Form and Structure and Meaning. When artists get together they talk about where you can buy cheap turpentine.”

And for whatever reason, the people who talk about where to buy cheap turpentine create better form and structure and meaning than the people who talk about form and structure and meaning.

Now, in order to meet this technical challenge, Da Vinci not only pioneered new techniques, he also pioneered new materials. Instead of using traditional egg-based paints, he used many many layers of very transparent oil-based paints. And this also helped create a feeling of depth and three-dimensionality.

He also carefully studied perspective and optics. He observed how objects looked different at different distances, with different backgrounds, from different heights and angles.

Now we should also talk about Leonardo’s personal life at this time.

Everything about Leonardo was weird. He was a bastard. He was left-handed. He was a vegetarian because he was a great lover of animals and didn’t want them harmed. He dressed differently. He wore a rose colored tunic that came to the knees, where most people wore long tunics that went to the ground.

And his sexuality was different. In 1476 at age 24, he was accused of engaging in sodomy with a male prostitute, along with three other young men. The charges were dismissed because one of the accused was related to the Medicis, but this certainly does not prove that the incident never happened.

Florence at the time was much more tolerant of homosexuality than most other times and places in Europe’s history, but that had its limits. And the accusation seemed to have left an impression on Leonardo, who went into a little bit of a funk. Around that time, he wrote in one of his notebooks “If there is no love, what then?”

Of course, we can’t be sure of Leonardo’s sexuality, and applying terms like gay to the past can be anachronistic. But there are reasons to believe that he preferred male companionship.

He never pursued a physical or romantic relationship with a woman.

Throughout his career, he had a habit of painting androgynous figures, and while he was obviously interested in the male figure and drew many male nudes, he did not have a corresponding interest in the female figure.

In the one nude of a woman that he sketched, the genitalia looks dark and scary, and is anatomically incorrect.

So I’m not trying to play Sigmund Freud here but it does seem likely that he at least had some homosexual proclivities.

These anonymous accusations may have contributed to Da Vinci’s decision to eventually leave Florence in 1482. Although there was another, even bigger reason.

He had left Verrochio’s workshop to try to start his own, as would be expected from someone with his talent. But he was so unfocused and such a perfectionist that he could rarely ever actually finish a commission.

Soon, he’s got would-be clients hounding him to finish their paintings. Da Vinci of course wanted to finish the commissions and frankly needed the money, but he hated working on anything that didn’t fascinate him. And what fascinated him was learning. Generally, he had really high energy when a commission was started and he was figuring out the concept of the painting and the hurdles that needed to be tackled in order to make it happen.

But once solid progress was made, and he was sure he had figured out the problem, he would lose interest. He also hated finishing works because he hated imperfection.

This inability to finish works and the subsequent pressure from his clients sent him into a pretty severe depression. He wrote in his notebook at the time “Tell me if anything was ever done. Tell me. Tell me. While I thought that I was learning how to live, I have been learning how to die.”

Well in 1482, Da VInci turned 30, and decided to leave Florence. He was already an innovator and a recognized genius, but a remarkably unaccomplished one.

All he had to show for his effort were some contributions to paintings he did jointly with Verrochio, a couple of unfinished would-be masterpieces, and one undelivered portrait of a young woman.

Luckily, he would soon have the chance to start over.

He was actually sent from Florence to Milan as a diplomatic gift to the Duke of Milan.

Florence had commissioned a new type of lyre, which is a stringed musical instrument, and they sent Leonardo, who was a very gifted musician, to deliver the gift and play it for the duke.

The trip was 180 miles long, which Da Vinci knew because he developed a wooden odometer that made a mark with every wheel turn in order to track the length of the journey.

When he gets there, after he delivers the lyre, he writes to the duke of Milan to offer his services. He’s a little burned out on being a painter, so he really pitches himself as an inventor and military engineer. He says that he can design bridges, fortifications, siege weapons, canals, waterworks, public buildings, and more.

In his letter to the Duke of Milan, he throws in at the end, oh yeah, I can also paint. He puts it at the very end “likewise in painting I can do everything possible as well as any other man, whosoever he may be.”

Literally, by the way, I’m also the best painter in the world.

Luckily he is hired by the Duke of Milan. He never does make much use of his supposed skills in military engineering, but he produces pageants and theatrical performances, plays the lyre, writes, and paints a little for the court.


Pageants were a better medium for Leonardo than painting, because they had performance deadlines and therefore he was able to finish things.

He was apparently quite exceptional as a producer, it’s a shame that these productions are essentially lost to time. He had no way of preserving his plays as he did his paintings. But he put the same level of detail and interest into them.

In one play, there was a bird that flew through the scene. Now in a normal play, you maybe get a little fake bird, and fly it through the scene on a string.

But Da Vinci spent countless hours studying birds and their wings to find out exactly how they moved and at what speed and created an extremely realistic mechanical bird that flapped its wings.

But even pageants weren’t enough for Leonardo.

One of the reasons for being in Milan is that it was a larger city than Florence, and had a more diverse set of intellectual pursuits. Whereas Florence was the center for commerce and art, Milan also had more experts in fields like science, literature, medicine, and military engineering.

Leonardo had always been a doodler and a note taker, but it is in Milan that he starts keeping his famous notebooks.

The notebooks of Leonardo are incredible. He actually didn’t publish any of his scientific discoveries and observations in his lifetime, so it’s only through these notebooks that we get a glimpse of Leonardo’s true genius.

We see him propose an armored, human powered tank, flying machines, a telescope, siege weapons, waterworks, a machine-gun-like rotating cannon, a helicopter, scuba-like diving equipment, and much more.

We also see quirky observations from everyday life - such as the fact that a dragonfly's back wings go down as his front wings go up - and profound scientific discoveries - his realization that blood swirls and eddies in the heart wouldn’t be confirmed until the 21st century.

Leonardo dissected bodies and used the findings from these dissections to make the most accurate diagrams of the human body ever created to that point. It would take hundreds of years before they were again matched.

What comes through in these notebooks is his curiosity and the probing nature of his brain. On one page you’ll have a ground-breaking diagram of the heart, and a doodle of a tree, and a shopping list.

You’ll have the design for a new musical instrument and a riddle and a journal entry.

With the financial security that came from getting a regular salary from the duke of Milan, Leonardo had the freedom to let his curiosity truly run wild.

Now, all of this has to be caveated with the fact that he really only had one or two inventions that ever actually made it out of his brain and into the real world. And that’s still impressive. I mean, if in your obituary it said that you were the greatest artist of your generation AND you invented the wheel lock which was an important innovation in the science of warfare, I think you would consider that a very successful life.

But when you read through his journals, it becomes clear that he had so much more to contribute than he actually did.

The reason that he didn’t contribute more inventions and scientific discoveries was he didn’t have to. He loved learning for learning’s sake. In the field of art, commissions forced him to sometimes complete his work. Even then he often didn’t. But the fact that people were paying him and expected him to produce something forced him to take his innovations from the pages of his journals into real life.

But in the fields of science and engineering he had no such constraints and so he never actually finished things.

*** Break ***

The two great masterpieces that Da Vinci did finish during his first stint in Milan was the Vitruvian man and the Last Supper.

Now the Vitruvian man as not supposed to be a work of art. It was born from conversations he was having with his friends.

Leonardo had lots of friends. He was handsome, well-built and proportioned, generous, funny, and open. One friend he made was an architect and polymath from Siena named Francesco de Giorgio. Giorgio and Da Vinci traveled together to meet a scholar named Poggio Bracciolini who had recently translated the works of a Roman statesman and architect who lived in the first century BC named Vitruvian.

Vitruvian mostly wrote on architecture, but he had a long passage about human proportions and their relation to one another. It demonstrated that ideal, aesthetically pleasing bodies were defined by certain set proportions.

After meeting with Bracciolini, this translator, and reading his translation of Vitruvius, Giorgio and Leonardo, along with another one of their friends named Giacomo Andrea, set about trying to diagram the proportions laid out by Vitruvius.

Okay I just introduced a lot of names so I’ll go through that again. Vitruvius is the ancient Roman who originally tried to figure out the ideal proportions of a human body. Bracciolini is the one who rediscovered his work 1500 years later and translated from Latin into Italian. And Girorgio and Andrea are Leonardo's friends who are researching this stuff with him.

Giorgio and Andrea made their own attempts at diagramming the proportions set out by Vitruvius, and while they are impressive, more than anything, they serve to highlight the brilliance of Leonardo’s Vitruvian man.

For one thing, it is more scientifically correct than the others. The body looks more natural, the proportions more correct. It is also rendered more beautifully. The man is fully sketched out with proper shading.

The result is beautiful. Walter Isaacon describes Vitruvian man as “the ultimate symbol of the intersection of art and science.”

It has become a symbol of that, and also of the renaissance, of the beauty of the human body, of the reasoning capacity of man, and so much more. And I think it demonstrates the genius of Leonardo more than anything else.

It was not designed to be a work of art. It was a sketch in a personal notebook, created for no other reason than to satisfy his personal curiosity.

Can you imagine that? How amazing or an artist would you have to be for a glorified sketchbook doodle to become one of the great artistic works of all time?

His other masterpiece from this time was The Last Supper.

He was also doing it on purpose. It is in his time in Milan that he paints what is probably the second greatest painting of all time, the Last Supper.

The Last Supper was a masterpiece in every sense of the word. For years he had studied perspective and geometry in order to properly be able to paint scenes with depth, and The Last Supper was a masterpiece in creating the perception of depth.

He was also able to use sfumato and chiaroscuro to create the sensations of movement and emotion. The painting depicts the moment when Jesus has just told his apostles that one of them will betray him. His apostles appear to be in motion, talking, sulking, and gesturing their feelings.

Now I love the story of how he actually painted. So a contemporary wrote that he would “Come here in the early hours of the morning and mount the scaffolding and then remain there brush in hand from sunrise to sunset forgetting to eat or drink, painting continually.”

And then he goes on to say that on other days he would show up, stare at the painting for a while, and then leave without touching his brush.

It reminds me of the chapter in The Almanack of Naval Ravikant where Naval talks about working like a lion and not like a cow. Cows are walking around chewing grass all day. They are always kind of working. But lions rest and recharge, and then they spring and take down a gazelle and eat it. And he says that it’s better to work like a lion. And that’s what Leonardo does, he works like a lion, sometimes he works furiously, and then other times he doesn't work at all.

The biographer Vasari wrote about Leonardo and this habit: “Men of lofty genius sometimes accomplish the most when they work the least,” Let me repeat that. He goes on “seeking out inventions with the mind, and forming those perfect ideas which the hands afterwards express and reproduce from the images already conceived in the brain.”

And I think that’s true in many different fields. You have to take time away to think. Men of genius sometimes accomplish the most when they work the least.

*** BREAK ***

Okay, well this all happens in Milan but in 1500 the French invade and take over Milan and Leonardo has to flee for his life. So we will take over from there in part two, but I wanted to highlight a few things that I learned or took away from studying the life of Da Vinci.

The first is to strive to be curious. Challenge assumptions. Try to figure out how things work. I don’t think anyone can make themselves be as curious as Da Vinci.

The next is, and this is something that Walter Isaacons highlights in a really beautiful way, is how Leonardo combined observation and fantasy. So in Walter Isaacson’s book Leonardo Da Vinci he writes “Leonardo was one of history’s most disciplined observers of nature. But his observation skills colluded with rather than conflicted with his imaginative skills.”

In other words, he wasn’t just a keen observer of nature, of things that did exist, but he had a great imagination as well and was able to think up things that didn’t exist.

And I think both of those things make the other stronger.

I brought up the example of Pixar and talked about how people who are focused on the technical details, are also able to create some of the most creative and soulful art.

And I think that’s getting at the same thing. Observation and imagination aren’t mutually exclusive, as the quote said they collude.

And then the last thing I’ll say is Isaacson has a great line in his biography, he says obsession is a component of genius. And I would add that it is the greatest component of genius. The most important part.

And so it’s easy to look at the life of Leonardo and say “Man, he did some great things, but it is a real waste that he wasn’t able to complete more of his work. Imagine what he could have done if he was more disciplined about finishing things.”

But I don’t think it works that way. Leonardo was as great as he was in part because he ruthlessly followed his obsession. And if that meant that he lost interest half way then so be it.

And I think that is my biggest takeaway so far. Follow your obsession no matter the cost.


That does it for this episode. Tune in next time to hear more about Leonardo Da Vinci. Give me a follow on Twitter at BenWilsonTweets and please, if you liked this episode share it with a friend. More than anything, sharing the show is what will help me the most.

Until next time, thank you for listening to How To Take Over the World.

About Episode

The early life and career of Leonardo Da Vinci - artist, inventor, scientist, writer, playwright, and genius.

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FIND THE BEAUTY IN WHAT YOU DO - You can’t force yourself to be curious. Da Vinci was so curious because he saw beauty all around him. In the rocks and fields. In the little swirls of water and the curls of hair. That is why great artists make great scientists. Because that eye for beauty, that love, is what drives their scientific inquiry and passion.

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