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.


Since we don’t know much about the man, we must focus on his works. Without a doubt, these are some of the greatest literary works ever created. It’s incredible to read them today, even as translations given most of us don’t read ancient Greek. There’s a great level of craftsmanship that must have gone into creating such long-form poetry. Really, it does remind you of Shakespeare. Given so little remains of literary or even oral works before his time, you can genuinely claim that Homer has influenced every western story written since. Nothing like this came before, so the uncanny familiarity with even modern works tells a tale of enduring influence.

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.”

…on bringing an intensity. You don’t want your company to feel like a soft handshake. You want that athlete grip mood. Set the example. Get fired up about mundane things. Sit up in the chair. Lean into the conversation. Look people in the eyes. Don’t even blink. Bring an energy into phone conferences. Speak up. Set the pace. Never mumble. Never slouch into the office. Head up. Address the troops confidently. Come in the office ready to karate kick your competition. Desire deeds of war. Raise the war trumpets.

“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.”

…on providing the right tools. I cannot tell you how many times in my career I’ve started a job with an empty desk. No laptop. Then it comes in, someone else’s used and beat up two-generation old rust bucket. Atrocious. Do not hire expensive people and give them mediocre tools. Would you give Lebron your used sneakers? Give everyone a new laptop, for heaven’s sake. A beautiful fresh Macbook isn’t just a beautifully crafted piece of engineering, it’s a value statement for how you value your new employee. Best for the best.

“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.”

…on winning and losing. It’s the same. You see both sides. Nobody just wins. Big or small, they come in waves. If you let the wins get to you, the L’s will hurt too. You do your best and enjoy the process, not the outcome. Be stoic to the result, do not chase the wins.

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.”

…on keeping your cool. One of the big no-no’s of the founder is to show cracks in the system. The startup growth story is a beautiful thing, but in truth the ice is thin and smoke and mirrors are needed. There is a shared illusion maintained by the founders, spinning a story that everything will work out in the end.

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.”

…on the bitter end. Through my two startups, and observing many another, I’ve come to the conclusion that the only true law of startups is not to run out of money. The rest is debatable. It’s hardly surprising that the best unicorn stories involve lots of intrigue filling up Wired magazine spreads, because the great filter of cashflows washes away all stories short of spectacular.

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.”

…on taking advice. When you tell people you have a startup, it’s like some kind of universal permission to give you advice. Somehow it’s implied you have no idea what you’re getting into, you’re in over your head, whether the person dispensing has any relevant experience or 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.”

…okay I just left that in gratuitously, because lesbians. #sorrynotsorry

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

…on the value of a good night’s sleep. Science is increasingly showing how deeply sleep affects our life in the present, how we perform, and how we age. There are a few stupid ideals that persist in startup lore, and one of them is that work is more important than sleep.

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.”

…on knowing great enthusiasms. When exactly should your eyes shine with fire? When addressing your team with bad news. The absolute refusal to give up must emanate from your soul, and radiate like a furnace from your eyes. When listening to customers complain. How much you really DO care must permeate the ether of your Wednesday night conference call. When the platform is down, midnight is near, and the team is out of energy and ideas. You must bring in the huddle like a band of brothers about to rush into the trenches together, every man facing the ultimate sacrifice to get the job done. Because the job matters.

“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.”

…on seeing your team suffer. Clients will shout. Servers will crash. Bugs will refuse to die. Tempers will flare. You may find yourself standing there in empathy, without any solution but to order pizza. It can be painful not having absolute control of your business at that moment, and being at the mercy of others. But later, you realize your team will suffer much to keep the company alive. They choose to fight for you. That will heal the sore and fill your heart with love.

“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.”

…on the intoxication of danger. Let’s admit, the worst part of corporate tedium isn’t the perks or incremental pay grades. It’s just boring. Everything just seems of little consequence. The wheel can run without a few cogs. The war doesn’t need the man. It is designed that way.

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.”

…on invincibility. Elon is the quintessential invincible hero founder, the real-life Iron Man. If the’s a 10 on the scale, the question is how far are you willing to go? The higher on the scale, the higher the ambition. You can’t change the world at 5, or run a coffee shop at 3. It’s a personal question, and it depends on how badly you want to win. Is it about money, or something bigger? Remember Elon already had $200 million before he started Tesla or SpaceX. Not everyone is ready to carry that heavy armor.

“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.”

…on building your armor. If you weren’t born invincible, there are things you can do to level up. You can pay to remove menial tasks from your life, in the form of a personal assistant at work, and get nannies and cleaners to sort out your home. This frees up mental capacity to spend on bigger things.

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.”

…on winning the morning. You’ll find some great recipes online for how to build up to a winning combination of high spirits and sound body, ready to tackle a days worth of startup chaos. The common element is that of time. Only corporate fools scamper out of bed with a coffee into their first meeting.

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.”

…on solving the big problems. Let’s face it, despite all the marketing there are almost no companies that truly innovate anything. Even new ideas are highly incremental and timing-dependent, and most companies have no new ideas.

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.”

…on burning out. The entrepreneur’s ethos is all about not complaining, about doing the hard things, about unyielding stubbornness in the face of rejection and failure. So you become blind to the limit. It’s still there somewhere.

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.”

…on rubbing elbows with the competition. I’m the last person to recommend networking, but it does pay to know the competitive field. Having a casual relationship with your enemy founders is helpful to humanize them. They’re not boogeymen, or better or worse than you are. They’re on their own journey. Understanding their background and motivations will let you navigate the waters when it gets crowded. Never yield an inch though. You must retain your mental edge and superiority, just don’t say it out loud. You know it, that’s enough.

“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.”

…on the right time to start. Is it a young man’s game? Why? Having seen many types, young and old, it seems the real right time is when you can. The stereotype is that you have less risk and more ideas when young. That’s true for some, not at all for others. Some will perceive tremendous risk in loss of career or education opportunities. Some feel they need to learn before they apply. It’s true if you feel that way. Nobody can know but you.

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.”

…on maintaining underdog mentality. Peter Thiel wants monopolies, and unicorns are meant to swim in blue oceans. But nobody starts that way. Everyone starts as the scrappy underdog. Poor. Hungry. Desperate. It’s easier to rally the team around a common enemy. Big pharma. Big banks. Big bad wolf. The Empire. Embrace being the rebel scum. When you do make it big, you will miss the days when it was all a big dream.

“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.”

…on living on the edge. There seems to be a certain gravity with growth, that attracts bigger and bigger disasters. Asteroids coming in left and right, of increasing size. The black hole keeps getting bigger and pulling you in harder. There’s always a sense that you’re one fuck up away from totally imploding in a spectacular supernova. The stakes double each time, and you have to keep the game going. You have to learn to embrace it. Wear it like a memento mori. Joke about it. Worrying about it is simply not useful. Laugh in the face of death.

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

…on age mix. Often you see Silicon Valley darlings boast about how young their team is. Youth is a symbol of creativity and energy, and a low cost base. Diversity should be about more than race. You do want a mix of experiences. It’s not just age. Some are early bloomers in terms of maturity. Diversity of all kinds brings diversity of ideas, opinions, and solutions. That’s what you really want.

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

…on celebrating the big wins. Never let a win go unnoticed, or simply swiped away. Big or small. There will come times when you desperately need a win of any kind. So build winning capital early, often, at any and every opportunity. It builds a winning vibe, and when it gets tough you want to start from a high level of winning with capacity to make a few painful withdrawals.

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.