Why read biographies? If you want stories of people and interesting characters, fiction is better. If you want general, big truths, then you're probably better off reading the many non-fiction books that are about abstract truths and far-ranging concepts rather than the particulars of a single person's life.

Consider, for a moment, designing an algorithm for a problem. The classic way to do this is to think hard about the problem, and then write down a specific series of steps that take you from inputs to (hopefully the correct) outputs. In contrast, the machine learning method is to use statistical methods on a long list of examples to make a model that (hopefully) approximates the mapping between inputs and outputs.

Reading explicit abstract arguments is like the first method. Like explicit algorithm design, it comes with some nice properties – it's very clear exactly how it generalises and when it's applicable – to the point where it's easy to scoff at the less explicit methods: "it's just a black box that our pile of statistics spits out" / "it's just anecdotes about someone's life".

However, much like machine learning methods can extract subtle lessons from a long list of examples, I think there is implicit knowledge contained in the long list of detail about someone's life that you find in a biography (at least if you read about people who did interesting things in their life – but then again, if there's a biography of someone ...). Once you've read the details of how CRISPR was invented, Apple jump-started, or compromises reached at the1787 American Constitutional Convention, I think your model of how science, business, and politics work in the real world is improved in many subtle ways.

(Note that this argument also applies to reading history.)

And of course, since biographies deal strongly with character, there is an element of the novel-like thrill of watching things happen to people.

Walter Isaacson's biographies

I've read four of Walter Isaacson's biographies. Their subjects are Albert Einstein, Jennifer Doudna, Steve Jobs, and Benjamin Franklin.

The Einstein one I read years ago, and don't remember much detail about. It did earn a 6 out of 7 on my books spreadsheet though.

The Jennifer Doudna biography is the weakest. The main reason is that we don't get too much insight into Doudna herself or the way she carried out her scientific work, leaving Isaacson to spend many pages on other things: overviews of other players in the development of the gene-editing tool CRISPR that are more journalistic than biographical, and descriptions of the biology that are limited by Isaacson's lack of biological expertise (at least when compared to the best popular biology writing, like Richard Dawkins' in The Selfish Gene). Hand-wringing over James Watson's controversies takes up an alarming amount of space that is only partly justified by Watson's role as a childhood inspiration for Doudna. There's also a long section about the struggles behind the allocation of the CRISPR Nobel Prize (awarded in 2020) that is clearly balanced and thoroughly researched, but simply less interesting to me than similar segments in the Jobs or Franklin biographies, where the stakes are the fate of companies or nations, rather than who gets a shiny medal.

My guess is that these faults stem mainly from the more limited material Isaacson had access to. Albert Einstein and Benjamin Franklin are both among the most researched individuals in history. To the extent that Steve Jobs is behind, the interviews Isaacson personally conducted seem to have plugged the gap.

Doudna is still an inspiring person. She also has the enviable advantage of not being dead, and therefore may yet do even more and become the subject of further biographies. If you're interested in biotech, including the business side, or scientific careers that may one day win Nobel Prizes, the biography may well be worth reading.

Steve Jobs

A god-like experimenter who wants to figure out what traits make tech entrepreneurs succeed may proceed something like this: create a bunch of people with extreme strengths in some areas and extreme weaknesses in others, release them into the world to start companies, and see which extreme strengths can balance out which extreme weaknesses. Such an experiment might well create Steve Jobs.

Take one weakness: Jobs's emotional volatility and, for lack of a better word, general nastiness in some circumstances, including things from extremely harsh criticism of employees' work to horrible table manners at restaurants. This isn't unique to Jobs either: look at the Wikipedia pages for Bill Gates and Jeff Bezos, and you'll find that they brighten their subordinates' work days with such productive witticisms as "that's the stupidest thing I've ever heard" and "why are you ruining my life?" respectively.

Does this show that behaviour up to and including verbal abuse is a forgivable flaw, or even beneficial, in tech CEOs?

First, though verbal abuse is neither productive nor right, a culture of vigorous debate is a distinct thing with incredible benefits, and the idea that it serves only to hurt and marginalise is not just a misguided generalisation but sometimes diametrically wrong. The best example is Daniel Ellsberg recounting an anecdote from his early times at RAND Corporation in The Doomsday Machine (an unrelated book; my review here):

Rather than showing irritation or ignoring my comment [that he made at the first meeting], Herman Kahn, brilliant and enormously fat, sitting directly across the table from me, looked at me soberly and said, "You're absolutely wrong."

A warm glow spread through my body. This was the way my undergraduate fellows on the editorial board of the Harvard Crimson (mostly Jewish, like Herman and me) had spoken to each other; I hadn't experienced anything like it for six years. At King's College, Cambridge, or in the Society of Fellows, arguments didn't remotely take this gloves-off, take-no-prisoners form. I thought, "I've found a home."

Steve Jobs admittedly goes overboard with this. For example, people who worked with him had to learn that "this is shit" meant "that's interesting, could you elaborate and make the case for your idea further?". This is not just unnecessarily rude, but also unclear communication. The general impression that Isaacson gives is also not that Jobs was combative as a thought-out strategy, but rather that this was just his style of interaction.

I suspect that the famous combativeness of many tech CEOs is not itself a useful trait, but instead adjacent to several other traits that are, in particular disagreeableness (in the sense of willing to disagree with others and not feel pressure to conform) and perhaps also caring deeply about the product.

Consider another extreme Jobs trait: strange diets, and (in his youth), a belief that he didn't need to shower because of his dieting. This went so far that of the people Isaacson interviews about Jobs's youth, including those who hadn't seen him for decades, almost every one mentions something like "yeah, he stank". Yet while some leap to defend and (worse yet) emulate Jobs's verbal nastiness, presumably on grounds of its correlation with his success, far fewer do the same for his dieting and showering habits. (What conformists!)

I think the more general lesson is that Jobs was extreme in a lot of ways, including in the strength of his opinions and beliefs, and in not having a filter between them and his actions. He gets into eastern mysticism and goes off to India to become a monk. He gets into dieting and starts eating only fruit rather than just reading lifestyle magazines and half-heartedly trying diets for a week like most people might. He gets it into his head that the corner of a Mac isn't rounded enough and declares that in no uncertain terms.

So is that the key then: have firm convictions? We've gone from a maladaptive cliché to a trite one – and still not a very helpful one. Steve Jobs, with his "reality distortion field", may have been an expert at persuading people, but even he can't persuade reality to be another way. Even slightly wrong convictions tend to have nasty collisions with reality.

(It's worth noting that rather than being a stickler for one position or solution, Jobs tended to yo-yo back and forth between extremes, only slowly converging on a decision – something that often confused others at Apple until they learned to use a rolling average of his recent positions.)

The critical part, of course, was that Steve Jobs was right about a lot of things, despite several serious missteps (especially in regards to making over-expensive computers that no one wants to pay for). I think Jobs's success provides evidence that even in aesthetic matters, success has a surprisingly strong component of being actually right. And Jobs, who was all-around very bright despite not being a master of the technical side, seems to have mastered this.

Of course, the story of Jobs's success – which came in spite of his emotional volatility, and tendency to wish away problems rather than facing them – does not entirely fit the idea that success comes in large part from having well-calibrated beliefs about the world and going about achieving them in reasonable and rational ways.

I think there are three things worth keeping in mind.

First, it may well be that most successful people are successful "at random" (i.e. without having a rational strategy for achieving what they want to achieve), but that the probability of achieving your goals given that you have well-calibrated beliefs and a rational reality-accommodating plan is still very much higher than the probability of achieving them given any other strategy. That is, if $S$ is the event of being very successful (by some definition), $R$ the event that you follow a rational strategy and maintain well-calibrated beliefs and generally practice thought patterns that won't get you downvoted on LessWrong, $\neg R$ the complement of that event, $P(\neg R|S)$ can be high (i.e. most successful people became successful in not particularly smart ways), while $P(S|R)$ can be much higher than $P(S|\neg R)$ (following a rational strategy still gives you by far the best chances of success).

Second, Jobs's life illustrates the principle that you only have to be very right a small number of times – just like in general most of the return, especially in anything risky, comes from a small number of bets. He failed at managing, even when working under another CEO who had been brought in specifically to babysit him, to the extent that he was kicked out of his own company. He failed to build successful hardware after founding NeXT. However, he was really right about product design, and that was enough.

Third, though he did get away with ignoring many uncomfortable truths by simply willing them away, eventually reality hit back. He delayed dealing with the cancer threat when he was first told of it, and he trusted alternative treatments. The combination may well have killed him.

Benjamin Franklin

Benjamin Franklin was a newspaper publisher, writer, postmaster, ambassador, political leader, and scientist. He invented the lightning rod and realised that electric charge came in both a positive and negative form (and gave those names to them, as temporary ones until "[English] philosophers give us better").

He was one of the first or most influential pioneers of many other things as well; to take a random example, he thought up the idea of matched funding for a charitable project (and was quite proud of it too: "I do not remember any of my political maneuvers the success of which gave me at the time more pleasure, or that in after thinking about it I more easily excused myself for having made use of cunning").

More generally, he clearly enjoyed numbers and detail:

[...H]e loved immersing himself in minutiae and trivia in a manner so obsessive that it might today be described as geeky. He was meticulous in describing every technical detail of his inventions, be it the library arm, stove, or lightning rod. In his essays, ranging from his arguments against hereditary honors to his discussions of trade, he provided reams of detailed calculations and historical footnotes. Even in his most humorous parodies, such as his proposal for the study of farts, the cleverness was enhanced by his inclusion of mock-serious facts, trivia, calculations, and learned precedents

Do-gooders with time machines could do worse than giving him access to a spreadsheet program.

One of the best descriptions of Franklin's personality comes from Isaacson's comparison of him with John Adams (when they were both in Paris, late in Franklin's life):

Adams was unbending and outspoken and argumentative, Franklin charming and taciturn and flirtatious. Adams was rigid in his personal morality and lifestyle, Franklin famously playful. Adams learned French by poring over grammar books and memorizing a collection of funeral orations; Franklin (who cared little about the grammar) learned the language by lounging on the pillows of his female friends and writing them amusing little tales. Adams felt comfortable confronting people, whereas Franklin preferred to seduce them, and the same was true of the way they dealt with nations.

One striking things when reading about 18th century events is the informality and nepotism. For example, to become postmaster of the colonies, Franklin spent significant money on having a friend lobby on his behalf in London, and upon obtaining the position gave out cushy jobs to his son, brothers, brother's stepson, sister's son, and two of his wife's relatives.

Not only that, but the border between truth and fiction was also hazy in the press. Articles could be, without any differentiating label, either factual, obviously satirical, satirical in a way that takes a clever reader to spot, or outright hoaxes. Likewise Franklin often wrote and published letters to his own newspaper under pseudonyms, with various levels of disguise ranging from clearly transparent to purposefully anonymous (this, however, was normal, as it was often seen as unworthy of gentlemen to write such letters under their own names).

In other ways, the 18th century, and 18th century Franklin in particular, were surprisingly modern and liberal. Franklin took a very reasonable and liberal stance on the freedom of press:

“It is unreasonable to imagine that printers approve of everything they print. It is likewise unreasonable what some assert, That printers ought not to print anything but what they approve; since […] an end would thereby be put to free writing, and the world would afterwards have nothing to read but what happened to be the opinions of printers.”

He still exercised judgement over what he printed. When deciding whether to print something that violated his principles for money, he (reportedly) went through a process that many modern newspaper editors and Facebook engineers could well take to heart:

To determine whether I should publish it or not, I went home in the evening, purchased a twopenny loaf at the baker’s, and with the water from the pump made my supper; I then wrapped myself up in my great-coat, and laid down on the floor and slept till morning, when, on another loaf and a mug of water, I made my breakfast. From this regimen I feel no inconvenience whatever. Finding I can live in this manner, I have formed a determination never to prostitute my press to the purposes of corruption and abuse of this kind for the sake of gaining a more comfortable subsistence.

The 18th century offers some perspective about hostile politics too. After describing an extremely personal and angry election campaign (which Franklin lost), Isaacson writes:

Modern election campaigns are often criticized for being negative, and today’s press is slammed for being scurrilous. But the most brutal of modern attack ads pale in comparison to the barrage of pamphlets in the 1764 [Pennsylvania] Assembly election. Pennsylvania survived them, as did Franklin, and American democracy learned that it could thrive in an atmosphere of unrestrained, even intemperate, free expression. As the election of 1764 showed, American democracy was built on a foundation of unbridled free speech. In the centuries since then, the nations that have thrived have been those, like America, that are most comfortable with the cacophony, and even occasional messiness, that comes from robust discourse.

Isaacson points out that Franklin's popularity has come and gone, and explains this by making him the symbol of one side of a cultural and political dichotomy: tolerance and compromise rather than dogmatism and crusading, pragmatism rather than romanticism, social mobility rather than class and hierarchy, and secular material success over religious salvation. Thus, while immensely popular in the latter part of his life and after his death, once the Romantic Era got underway, he became seen as shallow, thrifty, and lacking in passion. For example, Franklin appears in Herman Melville's novel Israel Potter, a work that sounds like the most confusing Harry Potter fan-fiction of all time, as a precursor to today's shallow self-help gurus.

A perfect example of the type of cunning that made some people call him shallow comes from his time as a frontier commander. To get soldiers to attend worship services, he had the chaplain give out the daily rum rations right after the service. "Never were prayers more generally and punctually attended", Franklin proudly wrote.

Or: at the signing of the Declaration of Independence, John Hancock solemnly declared "There must be no pulling different ways; we must all hang together". Franklin reportedly responded, with a wit but not solemnity worthy of the historic occasion: "Yes, we must, indeed, all hang together, or most assuredly we shall all hang separately".

This oscillation between romantically-minded eras finding him shallow and business-minded eras finding him the godfather of all self-help gurus and thrifty entrepreneurs has continued to this day. It is true that his aphorism collections, as documented in his famous Poor Richard's Almanac, are more clever than insightful; that he was no moral philosopher; and that his virtue-cultivating efforts were often patchy. However, they are part of a crucial process: the separation of morality from theology during the Enlightenment, which "Franklin was [the] avatar" of. Franklin's foundational personal maxim, which he often repeated, is perhaps the single sentence that pre-modern religious countries most need to hear: “The most acceptable service to God is doing good to man".

The romanticists' criticisms are based on truths. Though sociable, founding and participating in many societies, his personal relationships tended to be intellectual but distant. Interestingly, despite his vast achievements, Franklin does not show signs of a deep unyielding inner ambition; he seems to have been driven by vague instincts to be useful, a sense of pride (which he tried to dull throughout his life), curiosity, and a delight in tinkering, planning, and organising. To his sister in 1771 he wrote "[...] I am much disposed to like the world as I find it, and to doubt my own judgment as to what would mend it" – a remarkable sentiment from the pen of someone who, not many years later, would be playing a key role in a revolution. And though even past the age of 75 he achieved a few minor things, like being instrumental in securing France's alliance to America, signing the peace treaty between the US and Britain, shaping the US Constitution, and being the head of Pennsylvania's government, he happily wiled away many of his latter days playing cards with only the occasional twinge of guilt. He specifically justified this in part based on a belief in the afterlife: "You know the soul is immortal; why then should you be such a niggard of a little time, when you have a whole eternity before you?"

However, even these traits seem to have made him exactly what America needed. He was a skilled diplomat in France partly because of his easy-going nature and lack of naked ambition. At the Constitutional Convention of 1787, he often hosted the (much younger) other leading revolutionaries at his house to talk about things in a less formal setting and soften their stances, and generally advocated tolerance and compromise. Isaacson cleverly summarises:

Compromisers may not make great heroes, but they do make democracies.

Perhaps the best known summary of Franklin's life is Turgot's epigram that "he snatched lightning from the sky and the sceptre from tyrants". Franklin himself had a go at this: he wrote an autobiography – then a rare form of book – and also proposed a cheeky epitaph for himself, including an exhortation to wait for a "new and more elegant edition [of him], revised and corrected by the Author".

He didn't just summarise himself, though. He also unwittingly wrote perhaps the pithiest summary of the spirit of the entire Enlightenment project, and consequently of the driving spirit of human progress since then. It was in a letter Franklin wrote to his wife, after narrowly escaping a shipwreck on the English coast in 1757:

Were I a Roman Catholic, perhaps I should on this occasion vow to build a chapel to some saint; but as I am not, if I were to vow at all, it should be to build a lighthouse.