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Walter Isaacson
Biographer; Leonard Lauder Professor of American History and Values, Tulane University

Walter Isaacson on Why Elon Musk Thinks Empathy is Vanity

📅 Jul 01, 2026 The Context Window with David Deming 47 MIN 31929 VIEWS 151 SEGMENTS · 2 SPEAKERS
Walter Isaacson went from a kid in New Orleans who didn't yet know writing was a job to authoring the definitive biographies of Steve Jobs, Elon Musk, Albert Einstein, and Benjamin Franklin. In this conversation with Harvard Dean David Deming, the acclaimed biographer argues that the most innovative people are often difficult, with a more complicated relationship to empathy than the word suggests; that "We hold these truths to be self-evident" is not a factual description of America, but a promise the country has spent 250 years trying to keep; and that artificial intelligence will revolutioni...

Questions asked in this interview

12
  1. 1:26So did you always know that you wanted to be a writer?
  2. 2:34Did you know then you wanted to be a biographer?
  3. 6:46And then if I were writing a biography of you, Walter Isaacson, what would be the self-flattery that I would have to pierce through?
  4. 10:21And so I'm curious, what strategies do you use or habits of mind to try to make sure that you're looking at somebody's life objectively, and how do you know when maybe you're close to the line?
  5. 12:34How many of the geniuses you profiled would've been admitted to a place like Harvard based on their traditional credentials, and what does that say about our admissions process?
  6. 17:26And so my question for you is what is something today that we all know is wrong that we lack the moral courage to fight against actively, that people privately say is wrong but don't have the courage to stand up to it?
  7. 24:20What did the founders mean by pursuit of happiness?
  8. 24:46So why does Jefferson change it from the pursuit of property or the holding of property to the pursuit of happiness?
  9. 28:59Do you think we're focused too much on that and not enough on liberty, let's say?
  10. 33:25Why do you tell them that, and how do they use AI?
  11. 34:55What are the best uses of AI to learn how to write, to learn how to do what Walter Isaacson does?
  12. 43:45What was Harvard's role in the country's founding?
David Deming 0:00 ↗
Steve Jobs, Elon Musk were both jerks. At Harvard, you have a technical term that begins with an A to describe those type of people.
Hi, everyone. Welcome to The Context Window. My guest today is journalist and famed biographer, Walter Isaacson. He's a Harvard alum who's written biographies of Benjamin Franklin, Albert Einstein, and more recently, Steve Jobs, Jennifer Doudna, and Elon Musk. I ask him, how many of these geniuses would have been admitted to Harvard today? I think you'll be interested in his answer.
His new book, The Greatest Sentence Ever Written, is also a biography, not of a person, but of a document, the Declaration of Independence, and more specifically, its famous second sentence. It's an incredibly timely book as we approach the 250th birthday of the United States of America.
Walter and I talk about why, "We hold these truths," is the greatest sentence ever written, where the founders fell short in living up to their own words, and his status report on this grand experiment of a nation founded on a set of ideals, how it's going, where it's headed, and what he's most worried about.
He also explains why he makes all his students use AI in the classroom, and how education and journalism can adapt to the changes to come. This was a really special episode, and I hope you enjoy it as much as I did. Email me at [email protected], and enjoy the show.
Walter Isaacson, thank you so much for joining me today.
Walter Isaacson 1:24 ↗
Hey, it's a real honor.
David Deming 1:26 ↗
So you came to Harvard in 1970, is that right? And you were a history and literature concentrator. You wrote for the Lampoon, and you were president of the Signet Society, which is a literary society. So did you always know that you wanted to be a writer?
Walter Isaacson 1:40 ↗
No, no. In fact, I didn't know you could be a writer. I met a mentor of mine, Walker Percy. In fact, if you look over that shoulder, that's an old picture of me and Walker Percy, the novelist, whose daughter I knew quite well.
He lived across Lake Pontchartrain from New Orleans. We'd go, you know, fishing and hunting at the Bogue Falaya, the bayou where they lived. And I kept saying, "What's your dad do?" And she said, "Well, he's a writer." And I knew you could be an engineer like my dad or a fisherman or a doctor. I didn't know.
And so I sat at the knee of Walker Percy, and he explained to me that there were two types of people who came out of Louisiana, preachers and storytellers. He said, "For heaven's sake, be a storyteller. This world's got far too many preachers." And so I ended up being mesmerized by the magic of storytelling.
David Deming 2:34 ↗
And I imagine that love grew when you were at Harvard because of all the experiences you had. Did you know then you wanted to be a biographer?
Walter Isaacson 2:40 ↗
No, but I'll tell you a story that I just ran into Doris Kearns Goodwin two days ago, and we joke about it. She says I embellish it a bit, but there's a kernel of truth to it. She taught a course at Harvard when she was Doris Kearns, American Presidency. I took it, and she was not a tenured professor.
She was filling in for Dick Neustadt, and she finished her dissertation and published it, and it was called Lyndon Johnson and the American Dream. It was basically biographical, and the Harvard Government Department denied her tenure.
She didn't get tenure because what she had done was biographical, and in the academy back then, they looked down on biography as being a distortion of history, sort of the great man theory of history. And after Doris got denied tenure for having written a biography as her thesis, people in the academy moved away from doing biographies.
You can talk to Drew Gilpin Faust about that, because she had done one, but then does The Civil War Dead. And it left the field of biography a little bit open to us non-academics, David McCullough, Doris Kearns Goodwin eventually, Robert Caro, and then a later generation of Jon Meacham and myself. And so for a long time, biography was out of favor at university.
David Deming 4:11 ↗
Well, I guess that was to your benefit, and we do make some mistakes here at Harvard once in a while. You were the biographer of Steve Jobs and Elon Musk, two of the great geniuses of our time, and you got to decide how history would remember them, which is quite a responsibility. So how did that change you, that process of embedding with them and knowing that you were gonna write about people who were important in history, and that the way you interpreted them and their lives was gonna be written about in the history books? How did it change you?
Walter Isaacson 4:41 ↗
Well, one of the things it did was that, as we said, biography was out of favor. And Henry Kissinger once said that when he was at Harvard, he was taught that history was made by great forces. And then he said, "But when I see it up close, I see the difference people make."
And so by being able to just spend time at the side of Steve Jobs for two years, day after day, night after night, I could see how his fingerprints touched the surface of history and put out ripples. Likewise with Elon Musk.
Now, we biographers know that we distort history a little. We make it seem like a guy or a gal goes into a garage or a garret and a light bulb moment happens, and in real life, we know creativity's a collaborative effort. Innovation is a team sport. And so I've written some books, like The Innovators was one of them, about teams that really create innovation.
But seeing Steve Jobs up close, and frankly, Elon Musk, I realized two things. Humans can really make a difference. I mean, SpaceX doesn't happen, the iPhone doesn't happen, if you don't have a Steve Jobs or an Elon Musk. Secondly, you realize people are complex.
These people, Steve Jobs, Elon Musk, were both jerks. At Harvard you have a technical term that begins with an A to describe those type of people, and I have to do it when I teach my students at Tulane or when I learned it at Harvard, remember that people are complex, history's complex, that Shakespeare teaches us that even our heroes like Henry V, he kills all the French prisoners.
They have dark sides, and even our villains like Iago or Shylock have a backstory. So I try to understand that people are complex, and I try to do what Dr. Percy told me, which is, "Let me tell you a story." I don't try to preach about these people.
David Deming 6:46 ↗
I would imagine that one of the important talents with being a great biographer is piercing through the self-flattery, the flattering story that people wanna tell about themselves to understand the real truth. So what is the self-flattery involved in the biographies of some of the men that you've written about recently, Musk and Jobs and others? And then if I were writing a biography of you, Walter Isaacson, what would be the self-flattery that I would have to pierce through?
Walter Isaacson 7:10 ↗
Yeah, on my own case, I realized there were certain things I don't do particularly well. I used to think I had a good trait, which we call empathy, and I used to think, "Okay, Steve Jobs didn't have that. He didn't really give a hoot about it." And Musk, boy, he almost had the opposite of the empathy gene, you know, real bully types.
One of the things that Musk said to me is like, "Okay, you take a great pride in the fact that you care about other people," because I'd be asking him, "How can you treat people this way?" He said, "But sometimes empathy is just vanity. You care too much whether people like you."
Now, as a dean at Harvard, you know that that can be difficult if you try to make everybody happy. And he said correctly that I was not very good at running CNN because I was just trying to make everybody love me, and I screwed up running the network.
So in some ways, I think at a certain stage in life, you become a little bit more aware of your strengths and weaknesses. I don't think I was ever a truly great manager or executive, even though I had to run big organizations, and I try to keep that in mind when I write about other people.
David Deming 8:27 ↗
One interesting thing about what you just said about empathy is that sometimes to be a great leader, you need to have empathy, but be willing to overcome it in order to get something done, to be a jerk, as you say. So do you think that Steve Jobs and Elon Musk have empathy and can just overcome it, or they don't have it in the first place?
Walter Isaacson 8:43 ↗
Yeah, I think that's a really good question. Let me process it. But what I would say is it's different, the two of them. Steve Jobs had really good emotional receptors. He had a high EQ, an ability to understand what made somebody tick, a real feel for human emotions, which is why he invented things like the iPod and the iPhone that connected technology to human emotions.
He was somebody, though, who understood that he sometimes had to overcome, to ignore his empathy, his ability to know that he was causing people pain. He said, "I can't afford to have B players on my team." And you know, he was very good at knowing how people feel. He could towel snap you emotionally and make you happy, make you sad, whatever.
Elon Musk, on the other hand, his brother once said, Kimbal, his brother once said, "I'm the one who got the empathy gene." Elon Musk is almost not of this planet born, in the sense that he seems like a cyborg. He seems like somebody who thinks of himself as an avatar in a video game, or he's playing a shoot-up game or Polytopia, where empathy is not your friend.
And I don't think that he truly understands or deeply feels other people's human emotions, which means he's really great at engineering, but when he takes over a company like Twitter, which involves human emotions, he's not as good at that as he is at designing the Raptor engine.
David Deming 10:21 ↗
And you embedded with these folks for two-plus years, which is a great way to get texture, and maybe this was obvious to you from the beginning, his lack of empathy. But you know, you learn so much about somebody's life that way. But it also threatens compromising your objectivity, and I'm sure you know that. And so I'm curious, what strategies do you use or habits of mind to try to make sure that you're looking at somebody's life objectively, and how do you know when maybe you're close to the line?
Walter Isaacson 10:44 ↗
Well, sometimes you like a person a whole lot, and that happened when I wrote about Jennifer Doudna, for example, who did the gene-editing technology called CRISPR, and the book is about her race with some people you know, which is, you know, sort of the Harvard/MIT crowd, Feng Zhang and others who were, David Liu, who were also doing it there.
And perhaps my book shades a little bit more towards favoring her role. Everybody loves an underdog. Although I'll say the Nobel Prize committee ended up on that side as well. But maybe that's just because I really, really liked her.
Now, in the case of Elon Musk, I spent a lot of time embedded with him. I had an Airstream trailer in Boca Chica, Texas, right in his driveway almost, where I spent morning, noon, and night with him. But there was not a big emotional connection that I had with him. It wasn't like I woke up every morning saying, "I really like him." I felt objective. I felt like a reporter. I felt like I could just tell the story. And I wasn't trying to please him.
You gotta keep in mind it's all about the reader. It's not about the subject.
David Deming 12:03 ↗
Yeah, so actually when the subject is a little bit of a jerk, it makes it easier to be objective.
Walter Isaacson 12:06 ↗
It definitely does, and you'd see him do things, and you'd say, "Okay, this is not my pal." And you draw some line somewhere. I'd go out to dinner when he was with his then-girlfriend Grimes or Siobhan or whoever, and you'd be with his group and talk. But if they were gonna go out and party, and it was just a pure party, that's, you know, I'd say, "All right, I'm not a social friend. I'm there with my notebook making notes."
David Deming 12:34 ↗
Yeah, that makes sense. It's interesting because of the geniuses that you've profiled, several of them didn't score well on traditional academic credentials. But I guess my question is a lot of these folks are, you know, definitely highly accomplished, are the kinds of people that a place like Harvard would've wanted to claim credit for after the fact, but do you think they would've been admitted? How many of the geniuses you profiled would've been admitted to a place like Harvard based on their traditional credentials, and what does that say about our admissions process?
Walter Isaacson 13:00 ↗
Well, I love the fact that Albert Einstein twice got rejected at the Zurich Polytech. I've always wanted to ask Bill Fitzsimmons to figure out who was that admissions director of the Zurich Polytech that turns down Einstein. He finally goes there.
And likewise, as you say, the people I write about were geniuses, but they were not necessarily conventionally smart. Bill Gates, who did get into Harvard, had a mental processing power and conventional smarts that far outstripped that of Steve Jobs.
But Steve Jobs in some ways may have been more of the genius because as he would say, he could think different. He was the crazy one, the misfit, the rebel, the one who thought out of the box. And I think that ability to be quirky and think out of the box, it even was true of Einstein.
He may not have been as conventionally smart, let's say, as Henri Poincaré, who's also trying to do relativity theory, but Einstein makes that mental leap that maybe time is relative and speed of light's always constant. You know, Peter Galison at Harvard writes about this so well. What was that mental leap?
And so I love Harvard particularly, having mentioned Bill Fitzsimmons, because it's not simply looking for whose conventional SAT scores are the highest. Somebody like an admissions director or vice president like Bill Fitzsimmons looks for the different sparks. You know, who's gonna be the Yo-Yo Ma, who, you know, I happened to go to school with. And it's not simply about conventional measures of IQ or processing power.
David Deming 14:55 ↗
So Walter, I wanna ask you about your most recent book, The Greatest Sentence Ever Written, which is, you claim, "We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among those are Life, Liberty and the pursuit of Happiness." Why is that the greatest sentence ever written?
Walter Isaacson 15:11 ↗
It becomes a forcing mechanism for a new type of nation on Earth. Up until then, most nations were either ruled because of the divine right of kings or the sword of conquerors, but the notion that, as Lincoln said, you could have a nation conceived in liberty and dedicated to the proposition that under the social contract of that nation, there was an equality of rights, that created a new form of government.
But obviously, when they wrote it, it was not true about the nation they had just formed. All were not equal rights. You had one-fifth of the people in the colonies were enslaved. You had women who didn't have the right to vote.
But as I say, it becomes not a description of America, but a mission statement, an aspiration statement that forces, becomes a forcing mechanism. When Lincoln said that about a nation conceived in liberty, it was four score and seven years after they wrote it, and it wasn't just that he was making a speech at Gettysburg. He was consecrating a cemetery in which 7,058 young people were buried because they had tried to make that sentence more true.
Likewise, the Seneca Falls Declaration giving rights to women, they invoke the sentence. Likewise, Martin Luther King invokes the sentence. Lyndon Johnson invokes it when he signs the Civil Rights Act. So I think it's a great sentence, not because it was correct, but because it pushed us to be more perfect, more correct.
David Deming 16:47 ↗
Right, it was the antecedent for a lot of changes that happened later because of the ideals it espoused. So I wanna ask you in this country and in this world.
Yeah, so I wanna ask about that contradiction you mentioned. So as you said, I think it was many of the founders enslaved people, I think 43 of the 56 signers enslaved people. And what I found interesting about your book, and I knew this before, but you really made it very clear, was that many of them actually deplored slavery in their private writing, but of course, enslaved people themselves and publicly didn't fight against it. So at some level they knew it was wrong, but they lacked moral courage, as all of us do.
Walter Isaacson 17:25 ↗
Absolutely.
David Deming 17:26 ↗
And so my question for you is what is something today that we all know is wrong that we lack the moral courage to fight against actively, that people privately say is wrong but don't have the courage to stand up to it?
Walter Isaacson 17:36 ↗
You know, Drew Faust, whose history I totally admire, we used to talk about when I was on Overseers and she was president of Harvard, that question, which is people, you know, at the time were saying, "Let's rename this hall. Let's take Lowell's name off of Lowell House. Let's whatever it may be." And certainly at other places, you know, there was much more of that.
And she said, "All of that is fine, but let's make sure we ask ourselves the question, 50 years from now, 100 years from now, if my name is on a room or my portrait is in a hallway at Harvard, what are they gonna say we did wrong and we got totally wrong, and that maybe it was so bad they should take our picture down?"
Now, obviously, if we knew what it was, we would be a lot better. But we should ask ourselves, all right, burning fossil fuels, will that end up being something that becomes so appalling that people will be judged for it? Eating meat. And let me say, you know, I'm not a vegetarian. I especially like fish, but also all meats.
And here's the tricky one for you, and maybe we don't wanna go too much into it: abortion. 50 years from now, people are gonna say, "Oh my God, you denied a woman's right to abortion? Take the picture down." Or maybe 50, 100 years from now, there'll be people say, "That was, you know, morally wrong. We should take people's pictures down."
I know how I feel on a woman's right to choose, but I don't know if, you know, I think we should all have some humility to think maybe we're getting things wrong today, and understand, I keep quoting Shakespeare, but he said, "Even the best are molded out of faults." We all have our faults.
David Deming 19:36 ↗
You know, and to your point, I think we're surely getting things wrong today, but we don't know. The question is, you know, the founders, and that's what's really striking about it, they knew. At some level, they knew. And so do you think there's something that people talk about in private circles now, in private writings, that we all feel is wrong, but we don't have the courage to stand up for it now? You know, is there something that stands out in your mind? You mentioned fossil fuels and eating meat. I think those are two good candidates. Anything else?
Walter Isaacson 20:01 ↗
I think the issue of race, and this is where you started with your question, for 250 years has been a narrative for this country, and we also don't talk about it too much. We have trouble talking about it in public.
I love living in New Orleans because I grew up in a racially integrated neighborhood. So many of my friends I grew up with and people I know now, my social circle is racially mixed. But I don't see that in other cities. Even when I go to Boston, I go to New York, whatever, still very segregated, and people talk differently about that.
I would think that it would be useful. This doesn't mean I'm picking on the sin we got right or wrong or whether DEI was an outrage or the greatest thing ever. I mean that we probably should learn to talk about race with people of different views and different backgrounds and different races a little bit better than we do, especially, as I may say, you know, up in some cities.
And what I try to do in my life with my friends in New Orleans is, like, if there's something about race we gotta talk about, let's talk about it.
David Deming 21:27 ↗
That's interesting. The book opens with a hinge point about the key beginning of the sentence, which is, we hold these truths to be self-evident, and you talk about that change from sacred to self-evident. So explain why that's important and who authored the change.
Walter Isaacson 21:42 ↗
Yeah, that was a Benjamin Franklin change. Thomas Jefferson writes the first draft of the sentence. That first draft is in the fly leaf of my book, where you see Jefferson's, "We hold these truths to be sacred." And you see the printer's pen of Ben Franklin with backslashes and writing in self-evident.
And Ben Franklin had been, I thought, well, that doesn't sound like Ben Franklin. He doesn't use highfalutin words. He would just use the word obvious. But no, he had spent time with David Hume, the greatest philosopher of the time, in Scotland in 1775, and Hume had come up with the notion of what we call Hume's Fork, of two types of truths, one based on evidence, like London's bigger than Philadelphia, and to know a truth based on evidence, you had to go find the facts.
Count, have, know the number of people in both cities. Then there's another truth which is an analytic truth, a self-evident truth, a truth by definition, is a simple way to say it, which is like all bachelors are unmarried. To know if that's true, you don't need to go surveying bachelors and saying, "Do you got a wife?" No. You know all bachelors are unmarried.
The reason that's important is it's not empirically true that all people are equal. Some are taller, some are shorter, some are smarter, some are better at sports, some are better at whatever it may be. But it is self-evidently true that they're equal under the social contract that the Declaration is trying to say, which is we all come out of a state of nature.
And that's where the sentence begins, we hold. Just like the Constitution begins with the word we, that's John Locke's social contract theory. And so it is a truth based on logic and definition alone that if we are forming this contract, we all have equal rights under that contract.
David Deming 23:36 ↗
So Ben Franklin was good at that, because that whole narrative that we're talking about with race and slavery and everything else, his life is an example of the narrative.
Walter Isaacson 23:48 ↗
He had had two enslaved people working in his print shop when he was young, but he realizes at a certain point it's abhorrent. And he becomes an abolitionist, writing great papers on, and even the president of the Society for the Abolition of Slavery when he was in his 80s, which back then was considered old.
And so you see his evolution, and I think we sometimes have to remember that people don't get it right, but you judge them on their moral evolution.
David Deming 24:20 ↗
What did the founders mean by pursuit of happiness?
Walter Isaacson 24:22 ↗
You know, every single document up until then talks about life, liberty, and property. That's the way John Locke has it in the Second Treatise. That's the way the Continental Congress in 1774 did a declaration of certain rights. That's the way the Virginia Declaration of Rights in June of 1776, written by George Mason, Jefferson's close friend.

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APA

Isaacson, W. (2026, July 1). Walter Isaacson on Why Elon Musk Thinks Empathy is Vanity [Interview transcript]. The Context Window with David Deming. CEOInterviews.AI. https://ceointerviews.ai/interview/3079825/

MLA

Walter Isaacson. "Walter Isaacson on Why Elon Musk Thinks Empathy is Vanity." The Context Window with David Deming, 1 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3079825/.

BibTeX
@misc{isaacson2026_3079825,
  author       = {Walter Isaacson},
  title        = {Walter Isaacson on Why Elon Musk Thinks Empathy is Vanity},
  howpublished = {Interview transcript, The Context Window with David Deming. CEOInterviews.AI},
  year         = {2026},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/3079825/},
  note         = {Speaker-attributed transcript with timestamps}
}