Homer Knew More About Startup Leadership Than Most CEOs

When people ask me what to read about leadership, they are usually expecting management books. And there are some good ones out there; I like The HP Way, for instance. But that’s not where I start: First, I tell them to go read the Iliad, which I find deeply moving. This week is a good time to explain why: Christopher Nolan’s The Odyssey opens in theaters on Friday, and for the next month everyone will be talking about Homer.

The Odyssey is a magnificent study of a single leader — resourceful, unkillable, talking and lying his way home past every obstacle the gods can arrange. It’s the sequel. Homer’s real study on leadership, the one with the whole cast, is the Iliad.

Read it as a founding story and the poem snaps into focus. Capital has been committed, a fleet assembled, a team taken aboard, an impossible decade-long project undertaken. Troy is the incumbent: old, rich, walled, deep in allies, and with no intention of handing Helen — another king’s stolen wife — back to a crowd of upstarts. To do so, regardless of the rights and wrongs of the case, would be a status degradation for a rich, mighty city. The Greek coalition is the challenger — new, improvised, held together by nothing but the prospect of glory and loot, some old oaths, and the force of a few personalities. Its leaders are a set of high-performing/high-ego archetypes you will recognize from your own life. For me, the Iliad isn’t a relic. It’s one of the best books on startup leadership that I know.

I was a CEO for the first time when I was 19. I can’t say I did a great job. But to the extent that I didn’t fail utterly, my having read and thought about the Iliad deserves no small measure of credit.

The Iliad opens with a fight between cofounders. Agamemnon, the coalition’s commander, publicly claws back the prize of honor — a captive woman named Briseis — belonging to Achilles, the most critical man in the Greek army. Achilles walks. And he takes his team with him. He sits in his tent with his small, fanatically loyal team of utterly effective Myrmidons, and sulks. The rest of the army is driven back to their ships, until the Trojans manage to light the first hull on fire.

Everyone in the startup world has seen this story: The aggrieved, brilliant, seemingly irrational technical cofounder who must be handled with kid gloves.

Homer wrote it first.

The leaders of the poem are the leadership archetypes of a startup, and I’ve met every one of them. If you’re leading a startup, think about which model you inhabit — I’ve personally inhabited a few different ones at different times. If you can consciously switch between archetypes at need, that’s a superpower. Not many people can do that. Fewer still can be several at once — it takes every one of these skills to take a city or build an organization. Learning to recognize the archetypes on your own team is the first step in knitting them together, so that they do as a team what none of them could do apart.

Achilles is the specialist technical founder. Singularly competent, and what he wants is credit — not money, not power. Glory. In Book 9, with the war turning against the Greeks and Trojan watchfires burning within sight of the ships, Agamemnon offers him a compensation package without precedent — gold, horses, seven cities, a royal marriage — to come back and fight. Achilles turns it down flat, because money is fungible and honor is not: “Cattle and sheep are to be had for harrying... but when his life has once left him it can neither be bought nor harried back again.” He knows his own trade and his value precisely: “If I stay here and fight, I shall not return alive but my name will live for ever: whereas if I go home my name will die, but it will be long ere death shall take me.” Homer even audits the trade: years later, in the underworld, Odysseus meets Achilles’s ghost, and the specialist recants — “I would rather be a paid servant in a poor man’s house and be above ground than king of kings among the dead.”

The prize Agamemnon is offering is compensation; what it denominates for Achilles is recognition. Once the recognition is violated, no package can buy it back — accepting payment would concede that the insult was priceable. Beneath the refusal is the oldest grievance of every under-compensated top performer, the flat reward curve: “He that fights fares no better than he that does not; coward and hero are held in equal honour.” Except that for Achilles, the currency that matters is honor, not money or power.

Achilles is irreplaceable: Ordinary people do extraordinary things merely because Achilles is there to inspire them. In Book 16 his lieutenant Patroclus puts on his armor, and the mere sign of Achilles routs the Trojan army. The rest of the Greeks believe that they cannot be defeated if he’s fighting: It’s a self-fulfilling belief. The genius specialist’s aura of brilliance is a company asset, and losing him is existential. Even if his individual skills can be replaced, he cannot be.

Agamemnon brings the resources — and doesn’t know what to do with them. He raised the coalition: over a thousand ships, dozens of proud kings under one banner, his own hundred ships the largest single contingent — assembling that is a real and rare skill, and the expedition exists because he could do it. He’s a brilliant fundraiser and marshaller of resources — he’s the outward-facing founder, who talks to the VCs and the customers, but can’t run the organization and doesn’t know how to delegate. His authority rests on his fundraising skills and his investable resources. Even Nestor, mediating the quarrel with Achilles, can offer no better argument than headcount: “You are strong, and have a goddess for your mother; but Agamemnon is stronger than you, for he has more people under him.”

But the poem is a catalogue of what he cannot do with what he raised. In Book 2 Agamemnon tests the army’s morale by announcing, falsely, that the war is lost and everyone should sail home — expecting them to demand to stay. They stampede for the ships instead, and it takes Odysseus, going man to man through the panic, to turn them around. Twice, in earnest, Agamemnon proposes to cut and run — “let us all do as I say and sail back to our own country, for we shall not take Troy” — and twice his own subordinates talk him out of it. He is the personification of power without competence, insecure about the gap, and that insecurity is the poem’s original sin: humiliating his essential man over a status token. And when he finally makes amends in Book 19, he cannot quite bring himself to apologize: “it was not I that did it: Zeus, and Fate, and Erinys that walks in darkness struck me mad.” The gods did it. Every apology you have ever heard from this founder is a version of that apology. Homer himself rejected the alibi: the first speech of the Odyssey is Zeus complaining that men “lay blame upon us gods for what is after all nothing but their own folly.”

I have sat across the table from more than one Agamemnon: a founder whose genuine superpower is assembling resources — capital, headcount, logos on a slide — and whose company goes nowhere because he cannot accept that others on the team want and deserve a share of the glory. A great founder knows that, regardless of titles and reporting structure and equity on the cap table, being the founder means that you get credit for the success of the team. Such founders are surprisingly rare.

Odysseus is the innovator, the strategist, and the dealmaker. Respected, courageous, and utterly loyal — his cunning is always deployed for the organization in the Iliad, never for himself. But his motives are illegible to plainer men, and it costs him. In Book 3, the Trojan elder Antenor — who had hosted Odysseus once on a prewar embassy — recalls that “one might have taken him for a mere churl or simpleton; but when he raised his voice, and the words came driving from his deep chest like winter snow before the wind, then there was none to touch him.” When the embassy goes to Achilles in Book 9, Odysseus recites Agamemnon’s enormous offer nearly verbatim — and quietly deletes the closing demand: “Moreover I am older and more royal than himself. Therefore, let him now obey me.” That quiet edit tells you a lot about the man. He solves problems one-on-one, by appeal to whatever the other man values most. And Achilles answers him, to his face: “Him do I hate even as the gates of Hades who says one thing while he hides another in his heart.”

Nobody doubts the dealmaker’s loyalty. His words are his weapon; he can swing a sword or shoot an arrow — he’s a great warrior — but he won’t use an arrow when a sentence will do. He sees deeply into the soul of whoever sits across from him. He listens more than he talks. And when he talks, he says only what needs to be said. But the technical leaders like Achilles don’t much like a man whose chosen weapons are words. They prefer simpler solutions.

And the words are only half of him. Odysseus is the coalition’s strategist — the man with the ideas, large and small, and the will to carry them through. You have already seen him work: the Book 2 stampede would have been catastrophic but for his intervention. In the same assembly, when Thersites — a ranker with a gift for grievance, “a monger of sedition” — keeps agitating to abandon the project, Odysseus puts him down on the spot, in front of everyone: “Check your glib tongue, Thersites... Chide not with princes when you have none to back you.” He understands that mutiny spreads, and he does not let it go unanswered. In Book 10, when Diomedes needs a partner for the night reconnaissance and is told to take his pick, he picks Odysseus: “If he were to go with me we should pass safely through fire itself, for he is quick to see and understand.” They take a Trojan scout alive, and it is Odysseus who runs the interrogation, drawing out of the man the whole Trojan order of battle — where each contingent sleeps, and where a newly arrived king lies exposed at the edge of the camp. The king is Rhesus the Thracian: before dawn, Diomedes kills him and the twelve best of his companions in their sleep, while Odysseus drives the king’s famous horses back to the Greek lines. In Book 19, with Achilles finally returned and howling to attack at once, it is Odysseus who insists the army eat first — “No man can do battle the livelong day... if he is without food” — because rage is not a logistics plan.

Athena tells him to his face — in the Odyssey, back on Ithaca — why she loves him best among men: “you are the most accomplished counsellor and orator among all mankind, while I for diplomacy and subtlety have no equal among the gods.” And when ten years of force fail, the war is won by his idea: the wooden horse. Homer keeps it offstage — we hear of it in the Odyssey — but the stratagem is his: Epeius built it, and it was Odysseus who sat inside commanding the ambush, deciding when the door would open. He finds a way. The misuse of this man is to treat him as a messenger or an ambassador, when he should be shaping the strategy. In the Iliad, Odysseus is my favorite character.

Nestor is the elder statesman. He is on his last campaign, and he knows it: “I too would gladly be the man I was when I slew mighty Ereuthalion... I was then young, and now I am old; still I can go with my knights and give them that counsel which old men have a right to give.” He wants only to be useful. Homer introduces him with the words falling from his lips “sweeter than honey,” having ruled over three generations of men. And his experience is real: the poem has him citing the Lapith wars, the cattle wars against Elis, single combat by the river Celadon. A deep pattern library — drawn from raids, border skirmishes, and duels, a different genre of war from a decade-long coalition siege. So he arrays the chariots the old way, because “this is how the men of old took towns and strongholds.” The elder’s experience is simultaneously the asset and the trap; he is fighting the last war, and his last war is not this one. It was Nestor’s idea to send Patroclus out in Achilles’s armor. Companies fail by ignoring their Nestor; they also fail by obeying him. In a world that changes quickly, beware of advice that worked 20 years ago, or 2 years ago, but that’s no longer relevant because circumstances have changed.

Diomedes is the A-player. When Achilles withdraws, Diomedes fills the vacuum without being asked — in Book 5, with Athena’s favor on him, he wounds two gods in a single day: Aphrodite, in the wrist, as she carries her own son off the battlefield, and then Ares, the war god himself, who roars “as loudly as nine or ten thousand men” and quits the field for Olympus. He volunteers for the night raid nobody wants. He speaks truth upward, in public, with his name attached. When Agamemnon proposes giving up the war and sailing home, Diomedes answers him in front of the whole assembly: “The son of scheming Cronus endowed you by halves only. He gave you honour as the chief ruler over us, but valour, which is the highest both right and might he did not give you.” Then, having said that to the leader’s face in open council, he commits publicly to the mission: “Nay though these too should turn homeward with their ships, Sthenelus and myself will still fight on till we reach the goal of Ilion.” No sulking, no faction, no price extracted for staying. He knows that someone needs to insist on continuing to fight when the commander loses his nerve. He is the iron in the organization. Every company lives and dies by retaining these leaders. They may not have a fancy title, but they make the place work. They’re the guys who show up to the CEO’s office with an existential problem that they’ve discovered, and a solution in hand that they started on six months ago, quietly, without mentioning it to anyone, just in case it was needed. And they don’t demand anything other than the respect of their peers and their team, a share of the glory and the upside, and a chance to do first-rate work. At a startup, people like this are worth their weight in gold.

Patroclus is the glue. He is the man everyone in the camp loves, the one who tends the wounded and weeps for other people’s losses. And when the crisis peaks, he is promoted into the founder’s armor — literally: “Let me moreover wear your armour; the Trojans may thus mistake me for you and quit the field.” It works, briefly, because the market can’t tell the difference at a distance. Then he presses past the ships toward the walls of Troy — the founder’s mission, not the deputy’s — and it kills him. The costume is not the capability. He just cannot do what Achilles could do. Companies do this to their best lieutenants constantly, and the lieutenants, out of love and honor and ambition, volunteer for it. Founders are, generally speaking, not replaceable. Patroclus doesn’t come back. When Briseis — the same captive woman the Book 1 quarrel was about — sees the body, she flings herself on it: “You were always kind to me and I shall never cease to grieve for you.”

Ajax is the workhorse. No divine patron, no day of wounding gods, no speeches sweeter than honey. He holds the wall, holds the ships, covers the retreats. When there’s work to do, there he is. In the Book 9 embassy, after Odysseus’s diplomacy fails, it is Ajax’s blunt soldier’s arithmetic that lands: “if a man’s brother or son has been slain he will accept a fine by way of amends... but as for you, Achilles, the gods have put a wicked unforgiving spirit in your heart, and this, all about one single girl.” Achilles’s reply: “you have spoken much to my liking.” Even Achilles respects him. And the workhorse’s creed, delivered as a prayer when the battlefield goes dark: “if you will that we perish, let us fall at any rate by daylight.” The misuse of the workhorse is invisibility: nobody notices him until the wall he was holding gives way.

The archetypes do not respect the battle lines; you will meet these men on both sides of the table.

Paris is the native prince. A prince of the incumbent — beautiful, charming, superbly connected, unreliable, hedonistic and self-centered — and the whole war is the bill for something he wanted and took: the wife of the man who was hosting him. Hector reads him exactly: “evil-hearted Paris, fair to see, but woman-mad, and false of tongue.” Even Helen concurs: “would, at any rate, that I had been wife to a better man—to one who could smart under dishonour... This fellow was never yet to be depended upon, nor never will be, and he will surely reap what he has sown.” Shamed into a duel with the husband he wronged, he loses — and Aphrodite “snatched him up in a moment... hid him under a cloud of darkness, and conveyed him to his own bedchamber.” That is the archetype: when things get hard, he is somewhere else, and the rules never quite apply to him, because the consequences never arrive, except when they are truly dire. From anything short of that, he is insulated. When Antenor proposes in the Trojan council to return Helen and end the war, Paris’s answer is that of a man who bears none of the cost: “I will not give up the woman; but the wealth that I brought home with her from Argos I will restore, and will add yet further of my own.” He will write a check; he keeps the prize; other men do the dying. Note the parallel to Agamemnon’s misunderstanding of Achilles.

Silicon Valley prizes this archetype as a founder, and for a rational reason: he is already rich, so he will never take the early exit — only the thousand-fold outcome interests him, and that is the outcome that makes a winning venture fund. The founder who turns $10M into $100M has done well for himself and his team, but the VCs regard it as a failure. For them to win, because 9 out of 10 of their companies fail, they need the tenth one to do 100 or 1,000x. The same math is his failure mode. A man who loses nothing when the company dies rarely finds the grit for the years when things get tough. On the other hand, when someone with these resources turns out to be tough and effective, the things they can do are astounding. Because they don’t have to worry about the downside cases. Great VCs, by the way, have come around to the idea that when a founder starts to deliver on generating the first 10x in value, they offer them a chance to get liquid on a few million dollars of shares in a secondary sale. This allows someone who wasn’t rich when the company started to swing for the fences in a way that is economically rational.

Hector is the burned-out founder. He is the best man Troy has, and he no longer believes in his own cause: “Well do I know that the day will surely come when mighty Ilion shall be destroyed with Priam and Priam’s people.” He is fighting his brother Paris’s war, in defense of acts he holds in contempt. I’ve watched founders arrive at this place — the market shifted, the board deadlocked, the premise broke, a competitor moved too fast, the outcome they wanted is no longer on the table — and they can’t stop, because they feel that they owe it to the investors, to the team that joined for the mission, to the customers and to the vendors.

Homer names the mechanism, and it isn’t exhaustion: It is the honor trap — aidōs, shame before the community. In Hector’s world the currency of leadership is standing before the community, and his deliberation outside the walls in Book 22 is all about reputation: “I dare not look Trojan men and Trojan women in the face, lest a worse man should say, ‘Hector has ruined us by his self-confidence.’” He has kept the army in the field against good advice, and now facing Achilles is easier than facing the people who trusted him. That’s the trap in its pure form: it feels like duty and functions like paralysis. In the same breath as his confession of unbelief, he tells his wife why he fights on: “with what face should I look upon the Trojans, men or women, if I shirked battle like a coward?” And as he walks back out the gate, Homer’s narrator files the verdict early: “so they mourned Hector in his own house though he was yet alive.”

Once a founder or an executive arrives at this point, the necessary thing is brutally difficult: admitting that he is done with the project in its current form. That can mean handing it to someone who still believes, and helping that person succeed. Or gathering the data that lets him honestly rebuild his own belief. It can mean rebooting the company to do something different, or renegotiating his relationship with the board and the cofounders. But something fundamental has to change. The worst available choice is to keep playing it out — playing it out is for big incumbents, who have brand power, social momentum, and who win by default. A startup has to be on the attack, and a burned-out leader won’t attack effectively. Better to walk away and leave it in other hands than to pretend to do the job.

The Iliad is the oldest surviving study of a talent-dense organization under existential stress — its only serious rival is the court of King David in the books of Samuel, written at about the same time — and the failure modes of organizations built around exceptional people have been the same for twenty-seven centuries. When you can name the archetype sitting across the table, you gain some real insight into what he’s going to be good at, what he’s going to do, and what will motivate him.

Homer gives you the patterns. Whether and how you act on them in time is up to you.

One thing you might notice: Nobody on the above list is a very effective CEO. That deserves some thought. Effective CEOs are very rare, because they need to partake of multiple archetypes, and they need to be able to work effectively with even more. Or they need to design their project and their organization so that they only need a subset of the archetypes on their team.

Homer makes the point himself, through Polydamas, the adviser Hector will not hear: “There is no persuading you to take advice. Because heaven has so richly endowed you with the arts of war, you think that you must therefore excel others in counsel; but you cannot thus claim preeminence in all things.”

The obvious objection is Odysseus. Strategist, dealmaker, the man who ends the war — why isn’t he the CEO? Homer answers in the Catalogue of Ships: Agamemnon brought a hundred ships to Troy; Odysseus brought twelve. The title follows the capital, not necessarily the capability. But the twelve ships aren’t an accident. Odysseus didn’t want in on this war. When the fleet sailed, the seer Halitherses prophesied the downside case: that Odysseus would come home “after going through much hardship and losing all his men... in the twentieth year.” The later tradition — Homer never mentions it — goes further: when the recruiters came to Ithaca, Odysseus feigned madness, yoking an ox and a horse to a plough and sowing his fields with salt, and was exposed only when Palamedes set the infant Telemachus in front of the plough and Odysseus swerved.

And the oath that pulled the Greek kings into the war in the first place? The same tradition says that mechanism was, ironically, Odysseus’s own invention: a strategy offered to Helen’s father years earlier to prevent a fight among the spurned kings over Helen’s hand. With the oath of Tyndareus, all of Helen’s suitors swore to defend the winner’s marriage. Odysseus proposed it to Tyndareus in exchange for help winning Penelope, whom he wanted instead of Helen.

So the coalition’s legal architecture was his own invention, and it’s what trapped him. The strategist was caught by his own liability-pooling mechanism when an outsider who had never sworn — Paris — appeared and took Helen away to Troy. Incidentally, another key character who never swore this oath was Achilles, who was a child at the time: He violates no oath by sulking in his tent.

Odysseus was dragged into this war by a novel governance structure he had designed himself, and an unanticipated, unlikely set of circumstances. He doesn’t want to be involved, but honor demands…

Then he executed for twenty years without complaint. That completes the archetype, and it answers the question: the people most capable of running the venture are often exactly the ones who know enough to not want to be CEO. Sometimes the strategist who told you the downsides and the problems, took the smallest position at the table, and then committed all the way to the end, is the one you want on your side.

Every startup is, in the end, a study in the priorities and values of the founders. You see the reflection of the founder’s souls in who they surround themselves with, and how the organization acts. The greatest privilege of being a startup founder, in my mind, is that it’s one of the only activities in human experience where you get to pick anyone in the world to join your team, if you can persuade them to do so. What people do with that privilege is always fascinating to watch.

Startups aren’t wars. The stakes are lower. When we screw up a startup, we get to shut it down and start again, with some lessons learned. We don’t even end up in debtors’ prison, or sold into slavery to pay off the debts. That’s a real innovation. The downside is capped at zero. But the human dynamics aren’t new.

Homer never saw a startup; nothing in one would have surprised him.

A coda: Tennyson wrote of Odysseus grown old in Ithaca, the dealmaker and innovator who cannot stop being what he is. The last name in the poem is Achilles: even at the end, the dealmaker knows that the most precious thing in the world is true, uncompromising excellence.

Ulysses

By Alfred, Lord Tennyson

It little profits that an idle king,

By this still hearth, among these barren crags,

Match'd with an aged wife, I mete and dole

Unequal laws unto a savage race,

That hoard, and sleep, and feed, and know not me.

I cannot rest from travel: I will drink

Life to the lees: All times I have enjoy'd

Greatly, have suffer'd greatly, both with those

That loved me, and alone, on shore, and when

Thro' scudding drifts the rainy Hyades

Vext the dim sea: I am become a name;

For always roaming with a hungry heart

Much have I seen and known; cities of men

And manners, climates, councils, governments,

Myself not least, but honour'd of them all;

And drunk delight of battle with my peers,

Far on the ringing plains of windy Troy.

I am a part of all that I have met;

Yet all experience is an arch wherethro'

Gleams that untravell'd world whose margin fades

For ever and forever when I move.

How dull it is to pause, to make an end,

To rust unburnish'd, not to shine in use!

As tho' to breathe were life! Life piled on life

Were all too little, and of one to me

Little remains: but every hour is saved

From that eternal silence, something more,

A bringer of new things; and vile it were

For some three suns to store and hoard myself,

And this gray spirit yearning in desire

To follow knowledge like a sinking star,

Beyond the utmost bound of human thought.

This is my son, mine own Telemachus,

To whom I leave the sceptre and the isle,—

Well-loved of me, discerning to fulfil

This labour, by slow prudence to make mild

A rugged people, and thro' soft degrees

Subdue them to the useful and the good.

Most blameless is he, centred in the sphere

Of common duties, decent not to fail

In offices of tenderness, and pay

Meet adoration to my household gods,

When I am gone. He works his work, I mine.

There lies the port; the vessel puffs her sail:

There gloom the dark, broad seas. My mariners,

Souls that have toil'd, and wrought, and thought with me—

That ever with a frolic welcome took

The thunder and the sunshine, and opposed

Free hearts, free foreheads—you and I are old;

Old age hath yet his honour and his toil;

Death closes all: but something ere the end,

Some work of noble note, may yet be done,

Not unbecoming men that strove with Gods.

The lights begin to twinkle from the rocks:

The long day wanes: the slow moon climbs: the deep

Moans round with many voices. Come, my friends,

'T is not too late to seek a newer world.

Push off, and sitting well in order smite

The sounding furrows; for my purpose holds

To sail beyond the sunset, and the baths

Of all the western stars, until I die.

It may be that the gulfs will wash us down:

It may be we shall touch the Happy Isles,

And see the great Achilles, whom we knew.

Tho' much is taken, much abides; and tho'

We are not now that strength which in old days

Moved earth and heaven, that which we are, we are;

One equal temper of heroic hearts,

Made weak by time and fate, but strong in will

To strive, to seek, to find, and not to yield.

The Homer quotations are from Samuel Butler’s prose translations (the Iliad, 1898; the Odyssey, 1900), with his Latin names restored to their Greek forms in the quoted passages (Zeus for Jove, Cronus for Saturn, Ilion for Ilius, Hades for hell). Ulysses is courtesy of the Poetry Foundation (https://www.poetryfoundation.org/poems/45392/ulysses).

My thanks to Leonard Hochberg, Jon Margolick, and Matt Russell for comments on earlier drafts, and to Anthropic’s Claude (Fable 5), which served as research assistant — finding and checking every Homer quotation against Butler’s text and red-teaming the argument. It’s an amazing time to be alive and to have such tools at hand. I’d also like to particularly thank Jon for encouraging me to write this up — I’ve been talking about my five original archetypes of startup leadership - Achilles, Agamemnon, Nestor, Odysseus and Hector - for years, but his excitement about the idea prompted me to sit down and really think about this.