Startup Lessons from History: Homer’s Iliad

I’m a startup guy that likes to read about history, and spend a lot of time thinking about… well, stuff. This ongoing series is an exploration and tribute to what history can teach us about startups, and life itself.

Homer is a man of mystery, mostly because records don’t go back to around 3,000 years ago when he was around. Sure, if you were a king or something, but poets not so much. He’s like the Shakespeare of his time. Was it one man, or was it just a style? We’ll probably never know.

Future sources, ranging from fact to historical fiction, may include famous generals, philosophers, statesmen, and a whole bunch of Romans.

These posts are long and rich. So enjoy it like a fine whisky. Pour yourself a glass. Don’t just drink to consume. Take a few sips, consider the flavors. Take your time. Revisit. Share with a friend. Maybe don’t finish the whole bottle at once. Bookmark this and come back to it later. It ages well.


The main epic poems attributed to Homer are Iliad and Odyssey. Today we focus on the first, which tells a very manly tale of ancient heroics. Mingling of mortals and gods in the conquest of Troy. Legend has it that Alexander The Great slept with a copy of the Iliad under his pillow, and that he chose the landing point of his Eastern conquests to trace the footsteps of the mythic hero Achilles. Good enough for us peasants, then.

Homer and his Guide, by William-Adolphe Bouguereau, 1874 (Wikimedia Commons)

“In very truth ye hold assembly like silly boys that have no care for deeds of war.”

“Let each man sharpen well his spear and bestow well his shield, and let him well give his fleet-footed steeds their meal, and look well to his chariot on every side and take thought for battle, that all day long we may contend in hateful war.”

“Then were heard the voice of groaning and the voice of triumph together of the slayers and the slain, and the earth streamed with blood.”

Focus on the process, chase perfection as that is always in your control. The result usually isn’t. If you listen to top athletes, they most enjoy talking about the process. The grind. The little details. That’s how performers become legends, because focusing on process is how you create longevity. Tom Brady isn’t always the best quarterback in any given year, he’s happy to settle for the best ever.

“Neither rage thou thus, I pray thee, in the forefront of battle, lest perchance thou lose thy life.”

Statistically speaking that would be a lie, but everyone is willing to believe. The team. Investors. Partners. Everyone wants to be part of a great story. So you have to maintain the image. We will win. We are winning. We’ve never not won. All mistakes were just valuable lessons in disguise. The future is ever brighter.

It can be a lot to carry. Daily meditation helps. Exercise too.

“Speak to me no word of flight, for I ween that thou shalt not at all persuade me; not in my blood is it to fight a skulking fight or cower down; my force is steadfast still.”

Then again, you don’t HAVE TO shoot for the stars. You can choose to take your time, and manage your cash burn conservatively. Hire one developer that you finance with your day job, rather than hire 10, quit your job, raise money and suddenly have a hard runway until you run out and die in a ball of cash fire. Don’t buy into the hype. Do your own thing the way you feel right. Nobody else gets to say shit to you, cause they ain’t doing it for you!

“Old sir, in no false wise hast thou accused my folly. Fool was I, I myself deny it not.”

So you become callous towards advice. Especially if you find any success. It almost becomes a badge of honor to have achieved something despite every critic. Doing it for the haters. But you would truly be a fool not to heed qualified advice, when it is rarely available. People you trust. People you respect. People who can call you on your BS, and tell you how it is.

Hold on to those people, as they will become priceless when the haters turn into yes men. Haters are healthy because they keep you sharp, yes men are deadly because they make you soft.

A Reading from Homer, by Lawrence Alma-Tadema, 1885 (Wikimedia Commons)

“And seven women will I give, skilled in excellent handiwork, Lesbians whom I chose me from the spoils the day that he himself took stablished Lesbos.”

“But Agamemnon son of Atreus, shepherd of the host, sweet Sleep held not, so many things he debated in his mind.”

I’ll be the first to fall into the romance of seeing Elon crashing at the Tesla factory for a few hours before fighting the next fire. But look at Elon. Does it look easy? Does it look like something any human could, or should do?

Even if you do take the time, it may not be that easy. When you finally rest, the demons come out. The little voices that are concerned about your cashflows. About the quality of your next release. About growth curves leveling off, god forbid. So you have to get out of your head. I recommend a combination of exercise, breathing practice, and meditation. Take control of your mind to make most of your waking hours.

“No man that met him could have held him back when once he leaped within the gates: none but the gods, and his eyes shone with fire.”

“Therefore the kings were going together, leaning on their spears, to look on the war and fray, and the heart of each was sore within his breast.”

“With our backs against the sea, and far off from our own land. Therefore is safety in battle, and not in slackening from the fight.”

Startups are different. You’re the dirty dozen raiding the Eagle’s Nest. Impossible odds. Every individual critical to the task. Each personality contributing to define a team culture. We succeed together or die together. Danger around every corner. The hours fade away as you pour your energy into the struggle. With a wide smile on your face.

A Manuscript of Homer’s Iliad from the 11th century (Wikimedia Commons)

“Thou doest on thee the divine armour of a peerless man before whom the rest have terror.”

“And he threw bronze that weareth not into the fire, and tin and precious gold and silver, and next he set on an anvil-stand a great anvil, and took in his hand a sturdy hammer, and in the other he took the tongs.”

Personally, I’ve found the combination of daily exercise, breathing practice, and meditation to further increase my capacity for effort and suffering. To take on bigger challenges, with thicker armor.

“Now Morning saffron-robed arose from the streams of Ocean to bring light to gods and men.”

Prepare yourself in those early hours. Wake early. Run. Lift. Shower, cold. Meditate. Feast. Approach each day with reverence. It’s not about showing up. It’s about showing out.

“Not lightly do the glorious gifts of gods yield to force of mortal men.”

To truly do something new is hard. Super hard. Elon hard. Don’t get it twisted — starting any company is hard. Keeping it alive is a constant struggle. So why make your life harder by trying to transform or even create new industry? Unless you have the ability to fund 10 years of R&D just do something incremental, like us mere mortals.

If you’ve already done that, and actually do have 100 milli in the bank, then fuck it, do it. Change the world. Because you can.

“Only when I cry to thee with my voice, then hold the unwearying fire.”

So take your breaks when you can, even when you don’t need them. It’s like putting money in the bank of your mental and physical capacity. Eat healthy. Sleep. Work out. Build capacity. If you don’t need it now, it’ll save your ass later. Save the heroics for when it counts, silent suffering is just foolish.

Lekythos funerary vase (detail) depicting Achilles dragging Hector’s body by chariot, 6th century BCE (Wikimedia Commons)

“Fool, not even yet hast thou learnt how far better than thou I claim to be, that thus thou matchest thy might with mine.”

“A young man all beseemeth, even to be slain in war, to be torn by the sharp bronze and lie on the field; though he be dead yet is all honourable to him, whate’er be seen: but when dogs defile the hoary head and hoary beard of an old man slain, this is the most piteous thing that cometh upon hapless men.”

Supposedly, late career founders are too comfortable, and have too much to lose. Then again it’s more likely you’ll be financially independent to spend a year with no income and not sweat it. Screw your sabbatical to learn languages and travel. Learn Python and hack together an app instead.

“Thereby they ran, he flying, he pursuing. Valiant was the flier but far mightier he who fleetly pursued him.”

“Now my fate hath found me. At least let me not die without a struggle or ingloriously, but in some great deed of arms whereof men yet to be born shall hear.”

“Thou knowest how a young man’s transgressions come about, for his mind is hastier and his counsel shallow.”

“Now all other gods and warriors lords of chariots slumbered all night, by soft sleep overcome.”

The Triumph of Achilles, by Franz von Matsch, 1895 (Wikimedia Commons)

“There is a time for many words, and there is also a time for sleep.”

7th century B.C. (Greece)

Is there a favorite quote here? Which historical figure would make a great episode?

Thinks about the future a lot. Founder of two startups. Lives in Singapore.