On this episode of Recode Decode, hosted by Kara Swisher, author Walter Isaacson talks about his new biography of Renaissance artist and inventor Leonardo da Vinci, which he describes has a “culmination” of themes he explored in past books about Ada Lovelace, Ben Franklin and Steve Jobs. Isaacson explains how da Vinci’s life story can inform our thinking today about innovation and technology.

You can read some of the highlights here, or listen to the entire interview in the audio player below. We’ve also provided a lightly edited complete transcript of their conversation.

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Kara Swisher: Hi. I’m Kara Swisher, executive director of Recode. You’re listening to Recode Decode, a podcast about tech and media’s key players, big ideas and how they’re changing the world we live in. You can find more episodes of Recode Decode on Apple Podcasts, Spotify, Google Play Music, or wherever you listen to podcasts, or just visit recode.net/podcasts for more.

Today in the red chair is Walter Isaacson, who I’ve interviewed many times before. He’s the author of a new biography of Leonardo da Vinci, perhaps our first and greatest inventor.

Walter Isaacson: What a great inventor.

What a great inventor, but Walter has previously written biographies of people like Albert Einstein, Benjamin Franklin and Steve Jobs — also great inventors — and is CEO of the nonprofit Aspen Institute. But that’s changing, is that ... We’ll talk about that in a bit. Walter, welcome to Recode Decode.

It’s good to be back with you, Kara.

Thank you. You are just like a machine of creating books. Your last book ...

I’ve been working on this for like 15, 20 years.

Oh, really?

It’s sort of the mountain I wanted to try to scale.

Because last time we talked, you had written about women in tech and stuff like that, and Steve Jobs before that, and obviously Franklin and Einstein. Let’s give the listeners a little background of all the books you’ve written, focused on inventors, really — on tech and inventors.

Yeah. I’ve written about a lot of smart people, Ben Franklin and Steve Jobs and Einstein, and I began to realize that smart people are kind of common. They don’t usually amount to much. You have to be inventive, as you said, innovative. You have to be creative and have imagination, and one of the things I learned from Steve Jobs, just watching him onstage, he always showed the intersection of the liberal arts street with technology street. He said, “That’s in the DNA, if you can stand at that intersection between the arts and sciences or between beauty and engineering. That’s where you’ll be the most creative.”

He really looked up to Leonardo da Vinci, and Bill Gates had just bought the Codex Leicester, which is Leonardo da Vinci’s great notebook on geology and science, and I realized that Leonardo was a person who best connected beauty to technology, best connected art and science, and so I decided that would be a combination of all these books about, “What is creativity and how do we achieve it?”

All right. So let’s talk about the books you’ve done already. You obviously are a journalist. Give a little background for yourself, because not everybody knows you.

Well, I grew up in New Orleans and worked on the paper down there.

Yeah, I hear that.

Yeah. Then, came up to Time Magazine back in the days when paper-based weekly news magazines actually were thriving.

Yeah. Some bad news for Time this week, actually.

Yeah. I know, I know. At Time Magazine, a couple of things happened. First of all, I was what was called a floater for a while. A floater means that one week, you’re writing in the medicine section, the next week you’re writing in the music section. Then, one week you’re doing business, next week you’re doing technology, then world affairs. You try to understand the patterns across nature. You don’t get siloed. You see many different disciplines.

It struck me that that’s been Franklin’s strength. He was a scientist. He did the lightning experiments, but he’s also a writer. He has “Poor Richard’s Almanac” and was a diplomat and everything, a musician. I said, “There’s some people who are great at being specialists. They’re great at geeking out, drilling down, but there are other people who see the patterns across nature.”

Now I realize, Steve Jobs was that way, even Einstein. When he gets stymied with his equations for general relativity, he pulls out his violin and plays Mozart because it helps connect him to the harmonies of the spheres. That, too, led me to Leonardo da Vinci, because everything ... he thought of himself as an engineer, and inventor, and a scientist.

At one point he’s writing a job application letter, right, when he’s reaching that very scary milestone of turning 30. He writes a job application letter to the Duke of Milan, it’s 11 paragraphs. The first 10 are all he can do in engineering, in invention. Says, “I can invent portable bridges, I can make great public buildings, I can divert water, I can make military weapons.” Only in the very last paragraph he says, “I can also paint.” So that ability to dance with nature across different fields ...

Which has been the commonality, all the people you’ve been writing about.

Commonality.

So before we get to Leonardo, because I want to talk only about Leonardo the whole time, but when you’re thinking about this idea of who you’re going to write about, can you just go through your process? Like, you say you’ve been writing this for 15 years. Tell me about that.

Well, I’ve loved Florence and used to go there as a student, and you’re always gathering string on Leonardo, and I saw some of his notebooks and I realized there was a lot of material there. But my process was, I was at Time Magazine, a close friend of mine, Evan Thomas and I were working there, and we were kind of frustrated because in the pre-internet days you’d write one page a week, and it was pretty, a little bit too easy.

We said, “Well, let’s do a book.” We did it, it was called “The Wise Men,” it was about six friends and how they created Cold War foreign policy. Not exactly a runaway bestseller, but fun to do. After I decided, “Well, I like writing books,” because in this day and age when we’re swamped with information, there’s something kind of cool about narrative, which means it starts at the beginning and goes step by step through time, and you see how people’s minds change, how they mature, how things build.

So I kind of liked writing books. I did Henry Kissinger, partly because “The Wise Men” ended with Vietnam and I wanted to try to do Vietnam. And frankly, after doing Kissinger it’s like, okay, after dealing with him I need to do somebody who’s been dead for 250 years.

You pick a lot of dead people.

Well, and Ben Franklin ...

Because Leonardo’s really dead.

Yes, well, 500 years, but he’s still alive on his notebook pages. But Ben Franklin, one reason I chose him is that at the end of Kissinger, I got to a point about realism in American foreign policy, how we sometimes do balance of power games. I realized Ben Franklin did that as a diplomat in Paris. He balanced the Bourbon-pact nations of France and Netherlands and Spain against the British alliance, in order to get the treaty that ended the Revolutionary War, but nobody writes about Franklin as a diplomat. They write about ... usually great English professors who write about him.

Then I discovered at the end of Franklin that his electricity experiments were so important. We sometimes think of him as a doddering dude flying a kite in the rain. No. The single fluid theory of electricity is an awesome discovery, and so too is the invention of the lightning rod. These are not little things we read in our childhood books and then forget about.

I realize that somebody like Franklin would have thought you a Luddite if you didn’t keep up with the latest in science. So I wanted to wrestle with science and then moved on to Einstein. Einstein, after I did Ben Franklin, Albert Einstein, Steve Jobs called me and said, “Do me next.” My first reaction was, yeah, well, okay Franklin, Einstein. I said, “Let’s wait 30 or 40 years till you retire.” But then I realized that ... Because I realized that I was told he was sick, that oh, if you’re going to do it, do him now.

That was a great opportunity that most people don’t have, other than Boswell with Dr. Johnson, to get very, very close with a person who significantly made a dent in the universe. I mean, I walk here and everybody’s on their iPod and their GPS and they’re tweeting and they’re doing all these things, and they’re calling Uber or they’re getting to their Airbnb, none of which would have existed if you hadn’t had an iPhone and then third-party apps on the iPhone.

So that was truly an opportunity to try to get right the most creative and beautiful and spiritual inventor of our era. After that, because he reminded me so much of Leonardo da Vinci, and then as I say Bill Gates was interested in Leonardo da Vinci. I had been sort of 12, 15, 20 years, every now and then get somewhere and say, “Oh there’s a Leonardo da Vinci notebook here in Paris or in the British Library or Windsor or in Milan,” or it would come on tour. I realize that basing something on his notebooks could show me how the innovation, engineering and invention connected with art and the beautiful.

So you started writing it 15 years ago. Talk about that. You were collecting string or you just had been long interested in him?

I’d been long interested in him. My wife had done her junior year abroad in Florence, and what struck me as I was gathering string was — not being able to see Virgin of the Rocks at the Louvre or the one in the National Gallery in London, but actually seeing his notebooks. They’re weird because he writes in mirror script because he’s lefthanded, and paper is sort of a premium, so on any page of the notebook you see a mind that’s beautifully dancing with nature, because he’ll go from a sketch of people at a table that might help him with The Last Supper, to a set design for a play he’s doing, to a flying machine that’s both part of the play but actually might become a real flying machine, to the mathematical problem of squaring the circle, all crammed onto a page.

In fact, there’s a wonderful page I love, I have it in the book so you can see it, a spread in the book in color, because after all these little things he’s doing on that page, he writes about boiling certain types of nuts in oil, and that you can use it to dye your hair blond, Connie blond is the word. I’m thinking, oh my gosh, he’s in his early 30s ...

It’s chemistry, right?

No, it’s not just chemistry. He’s a beautiful guy, when he’s young. In fact, Vitruvian Man, the naked guy spread eagle in the circle and square, that’s largely a self portrait, that’s what he looked like. He’s drawing himself inside the earth, the universe, and seeing how we fit into creation. So he’s kind of vain. He dresses really well, in purple and wonderful tunics and stuff, and there he is figuring out how to dye his hair blond. I go, “Yes! This guy is human.”

Through the notebooks, rather, I can humanize him, as opposed to just doing like other writers on Leonardo [who] mainly start with the 12 great painting masterpieces and discuss his life. I said, “No, let me do it page by page through the notebooks.”

One other thing, looking at those notebooks, this is a tech show, we’re on a podcast, we know all sorts of forms of new media. No doubt you’ve tweeted out the podcast and it’s on Instagram and Facebook and Snap and everything.

Instantly it will be.

Paper’s not a bad technology. It is really a good technology for the storage and retrieval of information. After 500 years, we still can turn the pages of Leonardo’s notebooks. From the 1990s, Steve Jobs had some memos on a NeXT Computer in his house. Even with his tech [abilities], we couldn’t retrieve that, because the NeXT operating system no longer can retrieve the documents that well. So every now and then, one of the lessons I learned is take notes on paper in a notebook. They’ll be around 50 years for ... You’ve got two kids, for your grandchildren or great-grandchildren. They’ll be around maybe 500 years.

Or try to do nothing on paper. There’s paper right here, but it’s unusual for me.

Yeah the paper here, I know, but I just mean maybe in the evening just keep a journal of a few things.

Well, we’ll get to that in a second, the lessons of Leonardo we’ll do at the end. But let’s talk about, so you started doing it, talk about the research, and then in the next section I’d like to talk about the meat of the book. It’s an enormous book, besides being sizeable. What was your thinking, how did you want to approach, as the definitive biography of him, or what was your thinking?

It was, to me, the biography that would weave together the science of invention and art. You take Kenneth Clark, great biography, but he says — I think it was written 80 years ago or so. He says, “Oh, if Leonardo hadn’t wasted so much time on math and invention he could have finished more paintings, it’s a shame.” I’m going, “No, no, he wouldn’t have been Leonardo if he wasn’t as curious about math and science and innovation.” Martin Kemp has written great books on Leonardo, but mine are kind of more chronological. They begin with him being born and they end at the end of his life. So it’s a way to weave together in a narrative, chronological way, all the aspects of his life.

All the aspects of his life. All right, we’ll let’s talk about him, because when you mentioned this to me I think two years, whenever you were working on it, I was surprised. Then I thought, oh of course that makes perfect sense, because just the things you just talked about. Talk about, you think the key things people get wrong about Leonardo, and then we’ll get into his life and how he conducted it, especially the math and science part of it. What do you think the conception of him is and is it close to the person who you have written about?

Well, I think the key thing people get wrong, who are scholars on him or art critics, is what I said about Kenneth Clark, which is that his time spent doing engineering and math was a waste, because none of his ... the helicopter never really flew, he tried to divert the Arno river and it didn’t get diverted, and the tanks never rolled, and he never squared the circle, which is the problem he spent his whole life doodling in his notebooks on.

I feel that if you don’t have the depth and breadth of interest of Leonardo, you don’t end up painting the Mona Lisa, or for that matter discovering how the aortic valve works. That was a major discovery. He does it because he loves how water flows and swirls, which is part of his art, it’s part of the curls of the people he paints, and it’s part of his science and it’s part of his anatomy dissections. So I guess that would be, to me, the biggest misconception, is that he was just a painter.

Which I don’t think people think anymore. It’s an interesting thing, because he’s known for everything.

Yeah, you’re right.

But let’s start in this section, the painter part. Talk about his painting and then I want to mostly talk about his science and technology.

Well, one of the thing he does in art that is truly significant is what’s called sfumato, which is the blurring of the lines, as if they were like smoke, because it stems from his science. He realizes that there are no sharp lines. You’re looking at my face right now, it’s not something you can draw in lines because the light hits the curves, the curves make different shadows. But also we have two eyes with large retinas, and so any line in nature is slightly blurred. So that’s a key to his paintings. So different, say, from Michelangelo, who draws with a disegno style, sharp lines.

Secondly, his ability to project three dimensions on a two-dimensional panel or surface was a huge leap of art that was happening around that time in the Renaissance. He’s very collaborative and he learns from Brunelleschi and Alberti, but also all the painters in the studio where he’s working. But he’s able to capture the mathematics of perspective and play tricks with it, so when you look at The Last Supper, the room looks deeper than it is because it’s an accelerated perspective. Well, that’s different from the flat paintings that came along then. But you’ll notice in both those cases, I talked about how the science and the art were blended together.

And how he used that. Especially, talk about the Mona Lisa in that way.

The Mona Lisa is the culmination. This evening, we’re in Washington now, I’m going to be at the National Gallery in front of Ginevra de’ Benci, which is a early, early portrait he did of a cloth merchant’s wife in Florence. It’s a great painting, but it’s not one of the world’s greatest masterpieces, because he’s trying to connect the rivers of the earth to the body and her emotions, but they’re things that don’t quite work. Near the end of his life, in fact at the end of his life, because he takes 16 years with the Mona Lisa, he spent a lot of time with it, it’s by his deathbed when he’s still dabbling with it. It’s the same type of picture. It’s a cloth merchant’s wife, a wife named Lisa, in three quarters profile with the river flowing from the eons of time, connecting her to the spirit of the earth, just like Ginevra de’ Benci, but they’re so different, the paintings.

So a lifetime spent in dancing with nature and being curious about every aspect of nature is reflected in the Mona Lisa. I can give you one specific example which I love, which is the smile. The greatest, most memorable smile ever. There are two things he does to make that smile work. First of all, he dissects more than 30 human faces. Peeling the face off cadavers and delineating every muscle that touches the lips, why the lower lip can move separately from the upper lip but the upper lip can’t move easily separately from the lower lip. Things you and I could figure out but we don’t, he did. He looked at every nerve that touches every muscle and whether it comes from the brain or the spinal cord. On like the 15th page of his notebook where he’s drawing these dissections, there’s a faint sketch, I have it in my book, that whole page, and at the top is a faint sketch which is the first attempt at the smile of the Mona Lisa. There she is, smiling, just the lips, smiling from the page.

Secondly, he had dissected the human eye. So he knows that light that comes directly into the eye and hits the very center of the retina sees detail, but the light that hits the edges of the retina see mainly shadows. So if you look directly at the corner of the lips of the Mona Lisa, there’s a tiny part of a detail that turns down slightly. But the shadows turn upward. So it’s a smile that’s elusive. You see it best when you’re not looking for it. If you’re staring directly at her, she may not seem like she’s smiling, it’s kind of enigmatic. But when your eyes wander to her forehead or her chin or her cheek, suddenly the smile lights up. It’s an augmented reality. It’s interactive.

We first see the Mona Lisa when we’re young, and we hitchhiked ...

Yes, it’s one of those paintings.

Back when we used to hitchhike a lot in Europe, you hitchhike to Paris, you get there, and there’ll be a whole lot of tourists. Nowadays you go there and there’s 200 people and they all have their iPhones and they’re not looking at the picture, they’re all taking selfies with themselves, or pictures of the picture. But as you stare at that picture, it suddenly dawns on you, I get it. This is in a class by itself.

Right. Do you think it’s one of the greatest painting, or has it become such a tourist attraction?

No, I think that there’s a reason that it has become an icon.

Why?

Because it is the greatest painting.

It is, because it’s an AR, I had no idea it was AR.

It’s interactive, your emotions change as you look at it, and then so do hers. Not only her smile, her eyes, famous. Mona Lisa eyes, they follow you, etc. Those type of things make it so that you’re not just seeing a flat portrait, you’re seeing something that ... a person who has emotion. And all of his life in his notebooks he’s trying to say, how do our inner emotions get reflected in our outward gestures and motions? Here it is, culminating in the Mona Lisa, it’s not just a portrait, it’s a psychological drama that you and I get to interact with. Nobody has come close to painting a painting like that.

I had no idea about the technology. All right, we’re here with Walter Isaacson.

You’re a tech podcast.

I know, it’s true, but I had no idea, now I know. We’re here with Walter Isaacson, his new book is about Leonardo da Vinci, the great inventor and painter. When we get back we’re going to talk about his focus on science and technology, which was vast, and a lot of his things that he thought about creating have come to pass, we’re going to talk about his background, how he got there. He’s one of the first, I think, probably one of the first famous entrepreneurs and inventors that we learn about as kids.

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We’re here with Walter Isaacson, the prolific writer, the journalist, someone I’ve known very well. He’s a New Orleans resident now, is that right?

At least half time.

He’s a man of the world, a man of letters and science.

So let’s take apart Leonardo. We just talked about his art, which I think most people know him best for, but of late a lot of people have been talking about his inventiveness and the science around it, and you noted that Bill Gates bought some of his notebooks, his most famous notebooks.

The Codex Leicester, an awesome, awesome notebook.

Yeah. So how much did he pay for that?

I do know, but I’ve sort of forgotten. I try not to.

Lots.

It was I think somewhere between 30 and 40 million, but it wasn’t a lot. It was definitely worth it.

Yes, why did he buy that, and let’s go into the discussions about his technologies.

I think Bill Gates, not to speak for him, but has a wide-ranging interest. He just listens to Richard Feynman lectures, he loves all forms of science, but also a great humanism to him. As we see. I think he was interested in Leonardo. I once heard Bill Gates say that Leonardo was the person in history who tried to know the most about everything that could be known. That’s something that’s quite inspiring, and there’s no better example of it. We have more than 7000 pages of his notebooks, but this one, the Codex Leicester, which shows water flowing into a pond, it shows the sun, it shows how light reflects from the earth to light up the new moon. All of these wonderful dances with nature, I think that — not speaking for Bill Gates — but that’s why anybody would want that notebook.

So talk about how he got this way. Not Bill Gates, but maybe that’s another biography for later for you. You shook your head.

He writes his own books.

That’s true, but he could be written about. So talk about what made Leonardo this way. How do you become a person that is that curious?

I think he had the great good fortune to be born out of wedlock.

Oh, okay. Most people don’t think of that as great good fortune, especially now.

Well, had he been legitimate born, he would have had to be a notary like his father and grandfather and great-grandfather were. Secondly, he would have been sent to one of the classical schools in Florence for the aspiring upper-middle classes and rising middle classes, or a university, and he would have been stuffed full of the medieval scholastic learning of the time.

Which was?

Yeah, which was medieval. I mean, that’s ... And it was before the scientific revolution and the Renaissance. Instead, he’s unschooled. So he has to teach himself. He calls himself a man without letters, meaning not schooled, a person who has to teach himself, and he says that made me a disciple of experience.

So that means even as a young kid in the village of Vinci, he is looking at swirls of water, testing things, drawing how water flows and erosion happens, drawing landscapes. Then when he moves to Florence at age 12, he’s always experimenting with things, because he has to teach himself.

So who did he grow up with? He grew up with his ...

He grew up with both his father, who was a notary, who at age 12 moved him to Florence, but his mother, who for the first time this year, working with Martin Kemp and Pallanti and others, we now know who his mother was, it’s in my book, which is a 14-year-old orphaned peasant girl from the village of Vinci. She also helped raise him, so he had a good-enough childhood. Being born out of wedlock was not ... Even popes around that time had lots of out-of-wedlock children.

So it wasn’t as bad.

In fact, it was once, Jacob Burckhardt, one of the 19th century historians, calls it a golden age for bastards because it actually liberated you from going into whatever the family business was and you got to become an artist, a poet, a gold-beater, or whatever.

It was around, it was not an orphan life, essentially.

Oh, it was definitely not an orphan life. And his father brings him to Florence, and apprentices him with Verrocchio, who has a studio. Now, this was a great studio because it’s doing not only art and sculpture, but pageants and plays, and it’s taking the copper ball, that has to be engineered and soldered using mirrors that concentrate the rays of light of the sun. It has to be soldered to be put on top of the dome of Florence’s cathedral, the Duomo, that little copper ball.

Who does it? Leonardo. He’s a young apprentice. He’s also posing for the statue of David as a 12-year-old kid. So we know what he looks like. He’s drawing all of these mechanisms that the studio is using to put the copper ball on top of the dome. So he’s teaching himself. He also has the good fortune to be born in 1452, right when Gutenberg opens up his print shop and starts selling books. It comes to Italy like wildfire. Italy actually becomes the center of publishing by the time Leonardo’s 15.

So in his notebooks we see Leonardo listing every week the books he wants to buy. It’s like Audible, we have to make our list. It’s like, “Get the Euclid,” and fortunately they were all being translated, because Leonardo wasn’t great at Latin, so, “Get the new translation of Euclid that’s at the stationers by the bridge.” These are the type of notes in his notebook.

So what makes him curious? What makes him curious is it wasn’t crammed out of him by some medieval scholastic schooling when he was 10 or 12, and he becomes curious. He wants to learn everything. So he’ll write, “Why is the sky blue?” Now, you and I quit wondering about that at about age 10. We outgrow our wonder years.

Right, absolutely.

Partly maybe because people cram it down and say, “Hey, hey, quit asking.” Leonardo never outgrew his wonder years.

Right, that’s a really good way of putting it. So he grows up, does this apprenticeship. Talk a little bit about the biography that gets him to the person.

Well, he’s an apprentice, and as I said, Verrocchio, his teacher and the master of the shop, does a lot of pageants, including for the Duke of Milan when he’s visiting Florence.

A pageant being a show, essentially.

Shows, outdoor shows. You know, we forget that there’s no TV, no internet, no movies, whatever. So what they do in the evening is they have performances. Some of them are plays, some of them are pageants, some of them are readings or debates. They stage Aspen Institute-like debates, but on grand stages. And they have parades, so one of the first drawings we have of Leonardo is a helmet for one of the costumes ...

I remember that.

For when the Duke of ... Yeah, it’s a beautiful metalpoint, silverpoint in the British Museum, I remember seeing it for the first time. You go ... What people don’t realize, they think it’s a piece of art. No, no. He’s working for Verrocchio, the Duke of Milan is coming to visit Florence, and they’re putting on a parade, and they have to give everybody helmets, and there’s a dragon and eagle’s wings coming out of it, it’s a great fantasy helmet that you and I may have done when we were 10 or 12 years old. Leonardo’s still doing it when he’s 15 or 20. So I think we don’t realize how important plays and pageants were.

Sure, right, to him.

To his growing up.

What do you think gave him, besides being a bastard, an entrepreneurial bent? Or just people are born with it? Because you’ve written about a lot of different people who are entrepreneurs.

Well, first of all he had an imagination, because one of the things about doing plays, pageants and spectacles is you have to blur the line between fantasy and reality. So he’s inventing things. You know that helicopter screw that everybody says, “Oh, he invented the helicopter.” Not exactly. I studied the notebooks. That aerial screw thing was actually done for a play. They’re bringing the angels down from the rafters, and it curves like that. He loves that spiral form of the curve and he loves the flying of the angels and what he called ingenue, ingenious devices.

So he starts inventing ingenious devices for the theater. He blurs the line between imagination and reality. Then he says, “Okay, now let’s try it in the real world.” And now he then does try to make flying machines. He makes gliders. He makes all sorts of weaponry and machinery that are sort of based on some of this theatrical imaginations.

Why is he the one? Because a lot of people do that in theater and then they don’t take it to the next step. What do you think it was about him that he wanted to keep doing it? There’s just this restless curiosity?

I’ll push back a little on the great entrepreneurial spirit, because he was inventive, and he always, he’d invent something that would carve needle ... I mean, would create sewing needles, like a thousand of them per hour, a machine. He said, “This is going to make me wealthy.” He even calculates how wealthy he’s going to be by how much he does. But then he never fully follows through on it.

So his ideas.

There’s something about Leonardo who loves the conception more than the execution. So we have a lot of inventions that never got made. We have a lot of paintings that never got finished. We have treatises that never got published. It’s a bit of a flaw, it’s also a humanizing thing about Leonardo, and it also is, I mean I remember Steve Jobs holds up shipping the original Macintosh because the circuit board inside is not beautiful enough. Steve Jobs knew that sometimes in month you have to follow the normal rule of real artists ship, you get things out the door, but sometimes in life you have to follow the rule which is let the perfect be the enemy of the good. Leonardo sometimes — often — let the perfect be the enemy of the good.

You say Steve Jobs executed quite well and Leonardo didn’t.

But that’s why, by the way, Steve executed quite well, although better on his second tour of duty at Apple than in his first. One reason he leaves Apple in 1985 is, shall we say, the Macintosh is a work of absolute beauty but the execution, sales, supply chains and everything are not working all that well. Likewise, with Leonardo, he executes very well on certain things, but he keeps his inventions and his paintings with him rather than deliver them to patrons all the time. He did not dance to the financial incentives of patrons.

What would you say his personality was like?

Very collegial.

Collegial, rather than ...

He loved everybody around him. You have a contrast of the two great geniuses in Florence at the time. Michelangelo, Leonardo. Michelangelo’s a recluse, sleeps in his dark clothes and boots, doesn’t have any close friends. Leonardo, the other extreme. Throughout his notebooks and the letters and notebooks of contemporaries, he seems to have about 30 best friends. Luca Pacioli, the mathematician, Bramante, you know, a great artist and architect. He goes down the list of all the anatomists who help him, they’re going to do an anatomy book together.

Leonardo is always walking around town, famously in Florence and later in Milan, dressed to the nines, quite a dandy, with an entourage of really interesting people around him, having debates and discussions in town squares, riding off to Pavia for when they’re in Milan to try to figure out how do the proportions of a human relate to the proportions of a church, and he kept Vitruvian Man, that guy in the circle and the square.

One of the things I discovered in my book — and Toby Lester’s written a book about this too, others have done it — is that wasn’t a solo drawing. That was done with friends. He had two friends who were riding with him and doing things and helping design churches, and they all tried to get the man in the circle and the square to be a church.

So when you think about someone that’s an inventor, we’ll get to science in a second, but the technology stuff, the invention stuff. He thought these up but didn’t make a lot. Sometimes he made them or tested them and things like that. What do you think the qualities of someone like that are? Is that someone who you would think of today the same thing?

Oh yeah. I think there are a lot of people, and unfortunately, because this is not one of Leonardo’s great trades, we know a lot of people who come up with great ideas, love perfecting and perfecting and perfecting the idea, but aren’t great at getting the product out the door. I mean, one of the lines that Steve Jobs, Steve Case, Addison apparently used was, vision without execution is hallucination.

There are times when you think of Leonardo and you think, “Hey, that’s a bit of a hallucination.” That perpetual motion machine or that particular type of man-powered flying machine, that is never actually going to be manufactured. On the other hand, as I said, he blurred the line in paintings. Blurring the line as he did in theater, but also in his inventions, between fantasy and reality, actually helped him envision things that 100 years later people would invent.

Right, people would invent later. So he was an apprentice, and then talk about what happened. He was making money ...

He was an apprentice, and as I said, he’s doing paintings. He’s a moderately good painter in Florence in his 20s, but things don’t get finished, like the Adoration of the Magi, St. Jerome in the Wilderness. St. Jerome in the Wilderness is a great example because he’s starting to be interested in anatomy, and you see the entire muscle structure, how it informs the drawings that are going to become St. Jerome in the Wilderness, but he goes back to it 30 years later to redo the neck muscles after he’s done some anatomy. He keeps this thing like for 30 years because he’s a perfectionist.

So at age 30, as I said, he writes this job application, he goes off to Milan trying to be an engineer for the Duke of Milan. In about 1482, when he’s 30 years old, he moves to Milan.

He writes this 11-paragraph ...

He writes this 11-paragraph thing. He moves to Milan. He becomes the engineer and painter, eventually, to the Duke of Milan.

How did he get that job? I know it sounds crazy.

Well, the job application letter didn’t fully help because for the next few years he was just sort of, as you’d say, a freelancer, a contract worker. He doesn’t get a full-time job with benefits.

Gig economy.

By 1490, he’s got a room and board and weekly stipend, living at the castle in Florence, but it takes him a while to get the job, and part of the time he’s actually doing plays and pageants, which is his gig. He’s also inventing certain types of weapons because Milan had a pretty good army, unlike Florence, and he’s starting to paint, especially he’s painting the mistresses of Ludovico, who is the Duke of Milan. So you have Cecilia, the other ... Lady with the Ermine, great portraits.

So why did these people back then ... Talk about the system then. People who are somewhat knowledgeable about Florence or the Medicis or something there. Why did the Duke of Milan have people like this?

This is a great question.

Because you couldn’t start your own company then, if you think about if you want to give a ... Why do people have people like this?

Well, that’s a great thing, like why does the Renaissance happen when it does in Italy? Give you 100 reasons, but the one you asked about is you have a rising middle class, like the Medici. The Medici have become bankers in Florence. And by the way, they become huge bankers because like a lot of people today, they’ve invented new forms, like venture capital and private equity. They’ve taken one of Leonardo’s friends, Luca Pacioli, the mathematician, idea of debit and credit bookkeeping; double entries for debit and credit, which if you’re a businessperson listening to this you get how important that is.

That’s a pretty important invention. It happens right then. So the Medici become huge bankers, along with three or four other bankers. They’re all building their wonderful homes and palazzos, they have to show because they’re rising middle class and not aristocracy that they have as much taste and devotion and class as they do money, so they have a lot of madonnas painted for them by rising artists. The Medici become great patrons of the arts, and once again the Duke of Milan, Ludovico Sforza, his father was like a bad mercenary soldier, ends up taking over Milan. He’s not a hereditary aristocracy.

They want to bring smart people in.

Both because they want to embellish their court, they want to ... And many other reasons, and show their worthiness, they create around them courts that have everything from playwrights and poets, to mathematicians and architects and scientists and anatomists.

And engineers.

And engineers. They do it partly for the joy of it, but up until then you didn’t have wealthy patrons trying to prove that they had taste and class.

Was there use to it? So he’s hired as an engineer to do things, or lots of things?

He’s called the engineer and painter, he’s both. I’m not sure Leonardo, just like Steve Jobs, would make that big of a distinction between design and art.

So what did he do from a day to day? What was his job?

A lot of the evenings he helped put on pageants and plays or readings. They staged debates, one of which Leonardo debates that painting is a higher art form than poetry, for example, but they also do plays and pageants that involve big mechanisms and ingenious devices. But during the daytime too, he had paintings that he had to execute, such as most importantly The Last Supper, which he’s doing in the 1490s for the Duke of Milan, at a refectory or dining hall of a monastery, that the duke loved to patronize.

So Leonardo, I mean by this time he’s famous. People are there to watch, to be an audience while he paints. We have descriptions of him. He kind of blows in with his wonderful purple cloaks and tunics and stuff, and will stand in front of the painting for half an hour and then just do two brush strokes, and then disappear. He’d sort of say, “You have to let your ideas marinate,” and so he was a somewhat, he would paint during the day.

So he became famous during this time? He had been famous?

He’s definitely famous, especially by the time he pulled off The Last Supper in the 1490s, and he’s done quite a few portraits for the Duke of Milan. He had been semi-famous in Florence but a little bit more famous for not finishing the Adoration of the Magi than for painting the Adoration of the Magi.

All right, we’re here with Walter Isaacson, he’s written a new book about Leonardo da Vinci. It’s his latest book. Walter’s written a string of them, people that you might have heard of; Steve Jobs, Albert Einstein, and Ben Franklin, and Henry Kissinger, which is very different from that group. When we get back we’re going to talk about what Leonardo says about innovation and where innovation is going. We’re here on Recode Decode.

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We’re here on Recode Decode, and our guest is Walter Isaacson, who I’ve known for a very long time, he’s a great writer, and his latest book ... He’s a reporter, writer and a thought leader, I would say.

Oh, well ...

Oh you are, you have the Aspen Institute, you guys ...

A thought follower.

No, you guys have a lot of big thoughts up there in the mountains. His latest book is on Leonardo da Vinci, and his impact on other innovators and moving things forward. We talked about the middle of his life where he started to get some fame and traction. What was his impact then and now? Let’s talk about that. How did his life end and how did he conduct, he just continued to do the same thing he did his whole life, or was there a difference?

He continues to balance engineering with art. Now, his art indeed surpasses everything anybody has ever done in art, and for that matter in engineering.

Right, I was going to ask, is there any engineering thing that he did?

No. He does a lot of engineering ideas, some of them come to fruition, as I say a century later or two centuries later.

Helicopter.

Exactly.

What else, what other things? People know about the helicopter.

Well, his ability to divert rivers and to show how water flows.

Why did he want to divert a ...

Well, you know, I think just as a little kid. I don’t know if you remember, I remember growing up in New Orleans, a little kid, and you find little streams and rivers in the bayou and you’re diverting it.

I never did that, Walter.

But from the very beginning of his life, the first sketch we have is a landscape drawing. The very last sketches are these swirls of the deluge, and him sitting there looking how water flows against obstacles and forms swirls afterwards. Hey, we all get interested, we all geek out on something, and that was Leonardo’s great fame.

So it leads, as I said, to scientific discoveries that are very significant. Like his dissections invent, among other things, the visual display of information. In other words, he dissects a lot of bodies, and layer after layer he shows the muscles and then the nerves and then the heart, and he does it in layers.

So he uses his painting skills.

Yeah. So the combination of that painting and drawing skills and his anatomy and science skills. So for example, there’s an aortic valve, and people thought that it’s when the blood pushes up from the heart chamber into the valve, past the valve, the pressure then closes the valve. Leonardo said, “No, that wouldn’t work, it would crumble, because I know how water works, flowing fluids work.”

He shows that when you go from a large ventricle to a smaller thing, there’s a swirl, because of the way, just like if you put a pipe into a bowl, it would swirl. It’s that swirl that because of the centrifugal force, opens up the membrane that then becomes the valve. Those are like, whoa, amazing inventions that just about 15 years ago they finally, totally proved with magnetic imaging and other ways to look at, actual, it happen.

So Leonardo designed, for example, for the Duke of Milan and then for Francis I, the king of France, who is his last patron. He goes to Amboise in France. He designs ideal cities, because he understands that the greatest scourge they have back then is the plague. It keeps decimating cities. He realizes bad sanitation is underlying the plague.

So he invents a type, or designs a type of city, in which below the surface there’s sewer drainage lines, that the water flows through to a lower surface with sewage and drainage, which also has deliveries and horses that they need to be cleaned up after, etc. The top layer is where the people walk and live.

Which is what we have today.

Yeah, it’s what we have today. Now, they never fully built it, either ...

But he thought about it.

But he thought about it and he drew it, and had they built it they would have stopped another 100 years of the plague, probably. The other thing he does, that I love, is mathematics. There’s a lot of mathematical things that kind of work, kind of don’t, but he tries something that’s impossible. Every now and then you have to try something that’s impossible to figure out why it’s impossible and to push yourself.

That’s the age-old problem of squaring the circle, which means taking a circle of a certain area and trying to make a square of the exact same area using only a protractor and ruler, for reasons that your listeners know, most of your listeners know, that’s impossible because pi is a wildly irrational number and so it can’t actually be done that way.

But Leonardo tries hundreds of ways to do it, even when he’s young, he’s drawing and you get to Vitruvian Man, there’s the guy in the circle and the square with the same area, tries to be, because the circle extends higher than the square so the navel can be at the center of the circle and the genitals are right in the center of the square.

But here’s what I was going to get to. His last notebook page that we know, because you asked about his life. He ends his life in France under the patronage of Francis I, and we have a page in which he’s thinking about a variety of things, but in the margin he’s doing four more drawings that show a right triangle, changing the length of the legs, triangles inside shaded, trying to do that transformation of shapes till the very end. The last line, it dribbles off, it says, “Here’s another way of looking at it.” Then it pauses, says, “But the soup is getting cold.”

You imagine, there he is, upstairs in the little manor house that he gets with his whole entourage and students and everybody’s waiting downstairs. His cook is named Materine, we know about her, when he dies he leaves her a cloak and some other things. You just imagine him there, even though he’s old, even though he’s dying, even though there’s people waiting downstairs, still trying to square the circle.

That’s great.

But the soup is getting cold.

How could he do ... We’re going to finish up talking a little bit how he would do today and where innovation is, because you’ve written that innovation’s been a big theme throughout your career. How would he do today? What would he think of the internet?

Well, there’s a couple of things I would think about. One is, as I said, he was born when Gutenberg ...

Right, so he loved technology.

So he loved to drill down and teach himself. He would love the fact that just like he could use books to teach himself everything from math to anatomy to Vitruvius’s design of churches and experience, and mix books with experience. He would just think that the internet is even greater than Gutenberg’s invention, because anybody anywhere can find out almost anything about everything, and then share their knowledge with anyone. This, to Leonardo, would be heaven.

I think a downside would be, in his notebooks you see at times he’s distracted, or he gets totally obsessed sometimes, like 42 attempts to square the circle all on one page, and just page after page of geeking out on squaring the circle. He had these mood swings and depressions where he’s doing storms and stuff.

In our day and age, he probably would have been diagnosed with 42 different types of ADHD and obsessive compulsive and depression and manic and I don’t like applying labels like that, and they may have put him on some pharmaceutical regimen to cure them all and we may not have had the Mona Lisa.

Right, right, that’s true. So what do you think his impact on innovation is? Because you said a lot of people were very interested in him. Where do we get innovation? Is that just born or just people are like that?

I think you can be as a kid curious, and especially if you’re like Leonardo, you say, “Let me just explore things,” because you have a natural curiosity. But here’s a point I want to make, and it’s one of the themes of the book. Partly it’s a natural curiosity, but it’s also something you can cultivate. You can will yourself to be more curious. When I look at the list of things he asked each day, like how does light form luster on a shiny leaf, why do people yawn, what does the tongue of a woodpecker look like? Who wakes up one morning and wants to know about a tongue of a woodpecker?

Right, I don’t know.

But Leonardo did. And throughout his life, it’s kind of an interesting topic. Each of us, in our daily lives, can pause for a moment. I’m sitting in a room, it’s a podcast room, and I’m touching the things that deaden the sound, and they’re pyramids, and the light’s hitting the pyramid, they’re quite beautiful, but I also wonder, okay, that pyramid design of the foam, why does that deaden sound a little bit better than a flat design would? You think about it for a moment, you can figure it out.

But having worked on Leonardo for so long, I try, I’m never going to be Leonardo, but I try to just see the most ordinary things in life and pause for an extra 10 seconds to say, “Why?” And be curious.

So are you worried about innovation now, or do you think this just always happens, innovation just happens in cycles, or where do you think we are?

I think we went through a period when you and I were coming of age, and when Silicon Valley had the combination of the microchip, the internet and the personal computer. Then eventually the iPhone, and then mobile. All of that comes together to create innovation that’s completely transformative. I don’t think we’re in a phase like that right now. Most of the innovation is on things like social media or whatever, which is fine, but it doesn’t change the world the way having apps on an iPhone allows Ubers and Airbnbs and everything else.

Although some might argue that the social media’s become weaponized.

Oh I think social media is deeply, deeply influential. Don’t get me wrong. I just think that it’s not like Gutenberg’s printing press, necessarily, in terms of being a platform upon which a whole set of intellectual property is ...

No, but we do get to yell at each other a lot, and get angry.

Yeah, and there’s, yeah. That’s a downside.

There’s not greatness in Twitter, let’s just say.

Well, I mean this will be for another podcast, but the type of social media we invented enshrines anonymity, which I think hurts the civility of it, and anonymity is very important, we have to keep it, but we also ought to have places, like Leonardo or Steve Jobs and others had, that are common ground, where you actually know the people you’re talking to. So, to me, I think we need civil places as well as anonymous places, but that’s for a different podcast.

But when we get ... Does genius just happen, like it’s born, or ...? You’ve been writing about geniuses, really.

When I wrote about Einstein, I said, “Okay, some people are just born.” They’re touched by lightning, and they have a mental processing power that will allow them to figure out tensor calculus and how it can be used to describe the curvature of space and time. You think, “No, I can’t pause each day and look at the sound acoustical tiles and be like Einstein.”

That’s why I liked writing about Leonardo. His first biographer, who was a contemporary of Vasari, another painter, said he was touched by lightning with superhuman powers. No, he actually ... Well, I mean he was touched with great talent in painting, but his ability to will himself to ask questions and be curious each day, the ability to push himself, to observe more carefully, go down to the moats around the castle and look at the dragonflies, full-wing dragonflies, to see if the wings alternate or whether they go in unison. You don’t have to be a genius to do it. You just have to have the will to be observant.

All of us can have the will to be more observant, can indulge fantasy and not knock it out of our children and ourselves the way we sometimes do, can indulge curiosity, even about not just useful curiosity, not just I need to know exactly how this new microchip will do a pascal code better or not, but curiosity for curiosity’s sake, like the tongue of the woodpecker.

It’s really interesting, because one of my sons is very inventive, like he’s got rooms and rooms of inventions.

This does not surprise me.

Well, I know, but I think he’s just born with it. I literally do, because the things he comes up with, I think about it a lot because I think, how did he get this way? Because my other son’s great and he’s really fun, but it’s not the same thing.

Well, we’re all born differently, and we all indulge that.

I know, but it’s a certain level of invention. He’s literally always ...

And you and Megan are going to be particularly good in not destroying that in him and not knocking it out of him.

No, not at all, but I do think it was genetic. I just do, I think he just has like ...

You will have experts on this show much better at knowing the mix and combination of heritage and breeding.

When I was thinking of Leonardo, like even I was looking at the notebooks, I’m like, he has a notebook like that. He just writes things down. He makes some of them, he doesn’t make some of them. I just wonder how, if it’s possible.

But don’t sell him short. It wasn’t just that he was blessed with it, it’s he is curious and indulges it and pushes himself and allows himself. So if we kind of say it’s all genetic ...

Genius, just genius.

Yeah, if genius is all genetic, then we’re not going to say, “Let me pause and look at the way the light’s hitting those leaves.”

Let’s end on that, because we’re facing some really big issues in this country, besides the horrible political environment, which will pass as they always do.

That’s about storms, they pass.

They pass. So what do you imagine are the lessons of Leonardo? Because it really is the very best of humanity, that kind of thinking, like this kind of thinking. So give me the end on, the lessons that we have to think about going forward, because we’re dealing with robotics, AI, automation, artificial intelligence, self-driving cars. There’s a lot of big challenges for our society. All of which are inventive, but ...

I actually end this book in a way I haven’t ended my other books, which is just come right out and say, “Here’s the 25 lessons.”

I know, that’s why I was asking.

Because in some ways it’s a culmination of having learned from Ben Franklin and Einstein and Steve Jobs and Ada Lovelace and the innovators, and this is somewhat of a culminating book. I don’t think I’m going to write about another big, innovative inventive genius again. So I say, “Okay, here are the lessons,” and some I mentioned, which is stay curious, take notes, be observant.

But I think one of the huge lessons of everybody I’ve learned about is to combine the humanities with engineering, to combine art with science. Nowadays we silo things, there’s going to be a point where even your inventive kid is going to be told, “Okay, drill down in engineering or math or whatever, specialize.” No. Learning coding is important and learning engineering is important, but someday machines will code pretty well and help us. But what will be the Ada Lovelace moment, because she was the one who wrote about this in 1830, was the combination of human creativity and machine processing power, having an inventiveness that will exceed what machines alone can do, or what humans alone can do.

It’s interesting. Some of the things, the jobs, the future, the only ones that will exist will be ones which have humanity or creativity also involved in them. Then the rest are just digital.

But “also” is an important word, which is you have to interweave an ability to be creative and a sense of the humanities, with a sense of engineering. You can’t be a humanist and cede that to the engineers. That’s what Vitruvian Man, that’s our poster for that, which is be like Leonardo, there he is, standing there, spread eagle, in the world, in the cosmos, trying to figure out how we fit in, combining creativity with scientific anatomy, and that humanism is what’s going to help us when we get artificial intelligence, when we face the moral issue that algorithms might get out of our control.

They are out of our control.

Right. And it’s those with a feel for both the humanities, history, art, music, and the patterns of nature, how they ripple from the rivers that we see as a kid, to our heart valve, to the equations we do to describe the curvature of space and time. All of these patterns, if we have a feel for it, and a feel for the humanities, which is about, at its core, why change happens, why some people resist it, and some people cause it. Humanities, at its core, is what is creativity, how do you achieve it? Leonardo, the lessons in the last chapter of the book are all about the need for that combinations of creativity.

Right. The thing is, the reason he is also known is for the movies and for the movie and the books by whatchamacallit. Did that bother you? The popularity of the popular books with Tom Hanks, “The Da Vinci Code.”

Oh, “The Da Vinci Code.” No. I love anything that makes ... I thought you were talking about Leonardo DiCaprio, who is doing the biographical movie, or at least bought the rights to it.

So this is to make this?

Yeah, he acquired the rights to make my biography into a movie. “The Da Vinci Code,” of Dan Brown, it’s a wonderful work of fiction. Sometimes he pushes it and says, “Oh no, it’s all true.” No, John in The Last Supper is actually John, it’s not Mary Magdalene. We know that. But, what he does and what Tom Hanks does, what all these people do, is combine imagination and fantasy with reality, and we can scoff at that or we can admire and learn from it. I think Leonardo would have us ...

Right, although people do think that’s Mary Magdalene now, you know that? Because of that movie.

Okay, let me just tell people, fake news is sometimes wrong, novels are sometimes fiction, and The Last Supper, trust me, John leans on Jesus’s breast, and in the painting he’s starting to lean the other way. Leonardo has created a narrative painting in which “one of you shall betray me” is emanating from Jesus, each one is reacting as they would in a theater, it’s not a still scene, it’s a dramatic, emotional, narrative scene, and that’s John, it’s not Mary Magdalene.

That’s just all it is? Oh Walter, you’re making ... It was so exciting when it was Mary Magdalene. What’s your next book? Last question.

I think I’m going to do a book about New Orleans and maybe about Storyville in the 1890s, maybe about Lulu White, who was an octoroon, who opened a sporting house and hired Jelly Roll Morton to be the piano player, and Louis Armstrong.

Oh, so totally different.

But also it’s about race, because that was before the color line was drawn, because it was right during that decade that somebody who was a neighbor, named Homer Plessy, boards a train and we get Plessy v. Ferguson, which is so destructive, because it allows the drawing of a color line legally. Those type of things interest me. But it’s not going to be another genius innovator book. Leonardo da Vinci and the last chapter of it culminates.

Culminates. And you’re leaving the Aspen Institute?

Well, I’m going to move down, I’m going to be a teacher of history, I’m going to teach at Tulane. My first course, which I hope you’ll come lecture at, is called History of the Digital Revolution, from Ada to Zuckerberg, and your listeners don’t need to explain what Ada to Zuckerberg means.

Are you running for mayor of New Orleans?

No, the mayor’s race is actually the week after next.

Well, there’s lots of mayor’s races in the future.

Well yeah, I mean four, eight years from now. I haven’t, I don’t know what I’m doing then. There are two wonderful women running for mayor of New Orleans this time around.

Good. All right, well, Walter Isaacson, as usual you are also a very curious person. I’m excited to read your next book.

What do you mean by that?

It’s a compliment.

Thank you.

Anyway, thanks for coming.

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