Startup Lessons from History: Seneca

I’m a startup guy that likes to read about history, and think about stuff. This series is a tribute to what history can teach us about startups, and life itself. Here we turn to one of the great ancient thinkers, Seneca.

Other installments you can check out:

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

Seneca The Younger

Seneca

One of the more popular Stoic philosophers today, Seneca, was around in ancient Rome to witness the time and death of Christ. No, they weren’t bros or anything. Seneca himself was a popular writer in his day, and became quite rich despite his (supposed) philosophical detachment from the material world.

If you haven’t come across Stoic philosophy before, it’s what hipsters moved on to when zen wasn’t cool anymore. The basic premise is to not worry about what you can’t control, and live a life of meaning and purpose. Seems pretty legit.

In the end, Seneca was ordered by Emperor Nero to take his own life, upon suspicion of involvement in an attempted assassination. While this seems unthinkable today, this wasn’t uncommon unfortunately, and draws parallels to the tradition of harakiri in Japanese warrior culture. Still, sucks to be him.

In more recent years Seneca has become popularized by Tim Ferriss. Seneca wrote several books including plays, but his most accessible and famous product are his letters. Like your middle school pen pal, just with less doodles. The letters offer highly compressed and practical advice on all manner of worldly concerns.

Here we go…

“Lay hold of to-day’s task, and you will not need to depend so much upon to-morrow’s.”

…on the difficulty of starting something new. While certainly words to live by, these words are especially relevant to the foundational stages of any new undertaking. What’s stopping you from getting to your goal right now, as in today? Are your hurdles and dependencies mostly mental? Instead of waiting for circumstances, opportunities, and stars to align, what could you do right now? Finish the article of course, but then get to it!

“The primary indication, to my thinking, of a well-ordered mind is a man’s ability to remain in one place and linger in his own company.”

…on the value of being self motivated. This will come in handy for any entrepreneur. Even when you grow the company, most people will be hired for specific tasks. You’ll still largely be alone with your vision and the frustrations of how to get there. Not having to rely on the opinions of others is a great asset in the age of crowdsourcing.

“You must linger among a limited number of master thinkers, and digest their works, if you would derive ideas which shall win firm hold in your mind.”

…on the difference between learning and input. The age-old questions of generalist vs. specialist. The world now wants you to be a generalist. Know little bits and pieces of everything, fed by largely un-curated streams from social media. If you really want to KNOW something, you’re better off choosing your own topics and going deep.

The mind is a muscle, and can learn over time to digest quite a lot. Think Da Vinci, or even Elon Musk. They didn’t get there by reading twitter feeds.

“Cherish some man of high character, and keep him ever before your eyes, living as if he were watching you, and ordering all your actions as if he beheld them.”

…on measuring up to a higher standard. Mentors are overrated. Rather than settle for some locally accessible former mid-level executive who thinks themselves rather wise, aim higher. Obama. Einstein. Jobs? Seneca, even? If you study them and their works, you can use them as a point of reference. What would he/she say about this? Would they approve of this or not?

“No prizefighter can go with high spirits into the strife if he has never been beaten black and blue; the only contestant who can confidently enter the lists is the man who has seen his own blood, who has felt his teeth rattle beneath his opponent’s fist, who has been tripped and felt the full force of his adversary’s charge, who has been downed in body but not in spirit, one who, as often as he falls, rises again with greater defiance than ever.”

…on learning to live with failure. Using the appropriate analogy of gladiators of ancient Rome, you wanted to experience enough failure to know what it’s like in that moment, how to stay composed on the edge, so you wouldn’t fear it unnecessarily. Absolute failure, i.e. death, kind of ruins it. So avoid that. Same for startups. Don’t go out of your way to play with failure. It’s like fire. At a distance, it can create the right mood.

The Colossus of Nero in front of the Colosseum

“Even bad fortune is fickle. Perhaps it will come, perhaps not; in the meantime, it is not. So look forward to better things.”

…on planning to fail. If your plan is to learn from a series of spectacular failures, then you’ll probably fail. Spectacularly. Don’t confuse experimentation with failure. You can still validate your business, without needing to fail. There’s nothing to idolize about failure. Is it the end of the world? No. Is it something you need to live with? Yes. Success is still preferable. So plan for that, instead. Then roll with the punches as they come.

“The fool, with all his other faults, has this also, he is always getting ready to live.”

…on procrastination between 0 and 1. If there’s something you’re planning to do after X, if Y, when Z, just do it. Starting a company or creating a new product isn’t an event, or a sprint. It’s a process, or marathon. Get on the road, put yourself in the game. Do things, however small they are.

Run miniature experiments to inform big decisions later on. That could include talking to people about your idea(s), one of the most overlooked forms of validation. NOTE: NDA’s aren’t worth the paper they’re printed on, except as sweet paper airplanes.

“The mind must be exercised both day and night, for it is nourished by moderate labour. And this form of exercise need not be hampered by cold or hot weather, or even by old age.”

…on old dogs. If you’re not learning, you’re not only not improving, but actually regressing. Getting worse, not better. Your ideas and perspective will degrade. So make a habit of learning. No, Twitter doesn’t count. Read. Listen. Learn new tricks.

“Take my advice; call wisdom into consultation; she will advise you not to sit for ever at your ledger.”

…on crystal balls. While your fancy spreadsheet model will buy you street-cred with the junior analysts of your investors, creating “Excel money” rarely shows up in your bank account. Worry about your customers, and help them, the rest will truly follow.

“You should lay hold, once for all, upon a single norm to live by, and should regulate your whole life according to this norm.”

…on becoming Ned Flanders. When you’re flexing your creative muscles heavily, like say in starting a new business, you want to limit the amount of mundane decision making in your life. Eat the same food, take the same bus, don’t start new hobbies, new relationships, move to a new city, or anything particularly interesting. Make your life as boring as possible, and pour the sweet creative juice and energy where it counts: your business.

Emperor Nero singing while Rome is burning

“Are you surprised, as if it were a novelty, that after such long travel and so many changes of scene you have not been able to shake off the gloom and heaviness of your mind? You need a change of soul rather than a change of climate.”

…on the fault in seeking novel experiences. The great escape from your reality. Perhaps the real solution is to not to escape from your problems, but do small things, however minute, every day towards a solution. Anyway, back to Netflix.

“That which takes effect by chance is not an art.”

…on your growth-hacking strategy. This often gets applied in a broad sense to life. Don’t worry about stuff that isn’t in your control. Similarly, apply it to your business. Do not spend focus and effort on changing your environment and circumstances. You’ll only find excuses and explanations for your eventual failures.

“Work is not a good. Then what is a good? I say, the scorning of work. That is why I should rebuke men who toil to no purpose.”

…on “hustling” and “grinding” towards your next pivot. People already work a lot. Linear increases rarely produce exponential results. Like Einstein’s definition of insanity, you shouldn’t expect the results to magically change if your activities don’t change fundamentally.

Spend more time thinking about work. What exactly are you doing? Why are you doing it, really? What is the priority of this specific task in relation to other possible tasks? Is there some other task which might make your current task easy or even irrelevant? What about your team? Do your prior assumptions when deciding the current course still hold? Is there new information to consider?

This is especially relevant for early stage startups, where if you end up going too far down the path of “toil to no purpose”, you have to “pivot”. Constant re-evaluation of what you and your team are doing is essential.

“But when, on the other hand, a man is struggling towards honourable things, in proportion as he applies himself more and more, and allows himself less and less to be beaten or to halt, I shall recommend his conduct and shout my encouragement, saying: “By so much you are better! Rise, draw a fresh breath, and surmount that hill, if possible, at a single spurt!”

…on positive feedback loops. If your cause is meaningful, i.e. not just about your ego or wallet, every drop of sweat and tears you pour will create more momentum. Customers bring more investors bring more employees bring more product bring more media bring more customers. It will take a life all it’s own. Surmount that hill alone, then aim for the mountain with an army of supporters!

“For this reason I hold that there is nothing of eminence in all such men as these, who never create anything themselves, but always lurk in the shadow of others, playing the role of interpreters, never daring to put once into practice what they have been so long in learning.”

…on confusing knowledge and action. Great that you won the local pub quiz by explaining blockchain to drunken tourists. Yet the universe is unmoved. Learning for the sake of learning is a form of mental masturbation. Learn only what you intend to apply. Elon didn’t think propulsion physics would be fun. He intended to launch a big fucking rocket.

“Fortune attacks us as often as we attack Fortune. It is disgraceful, instead of proceeding ahead, to be carried along, and then suddenly, amid the whirlpool of events, to ask in a dazed way: “How did I get into this condition?”

…on life happening to you. This is a poisonous illusion you’ve allowed your mind to create, by letting initiative slip away. The chain of specific “I don’t have the energy to think about this right now” decisions you made got you here. At any point you could have chosen differently. You had every chance. You allowed the environment and circumstances to define you. Shame on you for wasting your human potential.

Entertainment for the masses

“Our stupidity may be clearly proved by the fact that we hold that “buying” refers only to the objects for which we pay cash, and we regard as free gifts the things for which we spend our very selves.”

…on free lunches. The Ayn Randian entrepreneur doesn’t do free proof-of-concepts, equity swaps, memorandoms of misunderstanding, or partnerships with other early stage startups. Invoice your customers. Pay your vendors. Keeping your equity, control, and I.P. means keeping your freedom. Part with your cash, not your freedom.

“We should toughen our minds, and remove them far from the allurements of pleasure. A single winter relaxed Hannibal’s fibre; his pampering in Campania took the vigour out of that hero who had triumphed over Alpine snows. He conquered with his weapons, but was conquered by his vices.”

…on the silk slippers of success. Never get comfortable in your success. You didn’t make it. Small businesses should not project quarterly revenues. Small datasets don’t support smooth probability distributions. 1 becomes 0. Past performance does not guarantee future results. Print that on your startup hoodie.

“The hand which turns from the plough to the sword never objects to toil; but your sleek and well-dressed dandy quails at the first cloud of dust.”

…on the net present value of your MBA as a founder. Life doesn’t give extra credits for color matching your chart legends.

“Would not anyone who is a man have his slumbers broken by a war-trumpet rather than by a chorus of serenaders?”

…on getting up to slay dragons. Your vision for incremental improvements in regulatory compliance is making the team yawn with excitement. Billy just dozed off in the back row. What is your plan to colonize Mars??

Take your original problem, then think two giant steps out into a bigger problem. What is the problem of your customer? What is the problem of your customer’s customer? Solve that instead. If you get even 10% of the way there, you’ll have not only solved your original problem along the way, but achieved 100% more.

Rally the troops, blow the war-trumpet, and roar! Freeeedoooooommmm!!!

“The place where one lives, however, can contribute little towards tranquillity; it is the mind which must make everything agreeable to itself.”

…on your designer label bean bags and selection of complimentary organic snacks. Do something worth a damn, and your team will sit on cardboard boxes with you, and eat ramen noodles at midnight hacking together your next release. With huge grins on their faces, and the echoes of high-fives reverberating from the walls of your windowless excuse for an office. Life isn’t about pleasure, but exercising your fundamental human potential. Make a difference. Make a dent.

“Great generals, when they see that their men are mutinous, check them by some sort of labour or keep them busy with small forays. The much occupied man has no time for wantonness, and it is an obvious commonplace that the evils of leisure can be shaken off by hard work.”

…on the joys of digging trenches. In any business, but especially startups, there is always too much to do. You’re a scrappy puppy fighting the big dogs, making do on leftover scraps. Stretching the limits of the possible by hacking and hustling. Oh, what you could do with real resources! When someone in your team asks you what they should be doing, walk to the nearest mirror and slap yourself in the face. Your men should be much occupied. You have failed your men.

“But the wise man is fortified against all inroads; he is alert; he will not retreat before the attack of poverty, or of sorrow, or of disgrace, or of pain. He will walk undaunted both against them and among them.”

…on buffers, backups and parachutes. You were a real player back in the corporate world. A regular silk tie samurai. Wake up, princess. There’s no customer support to take customer complaints. It’s your mobile number. There’s no HR handbook to manage employee induction. It’s you on the whiteboard. No finance department to make the numbers work. You have the cash or don’t. No pre-sales team webinars to explain the product roadmap. That’s you fighting with the Skype connection. No inside sales to drive Q3 demand. No procurement. No legal. Just you, and whatever motley crew you convinced to join your hopeless cause. Embrace the struggle, or just give up now.

“He really lives who is made use of by many; he really lives who makes use of himself. Those men, however, who creep into a hole and grow torpid are no better off in their homes than if they were in their tombs.”

…on making millions or dents. If you end up among the 1% of founders who somehow scramble past the first year, and years later struggle your way to an exit among the permille of those who started, congratulations. You’ve joined the ranks of at least 15 million other millionaires on Earth. The universe is unmoved by your achievement.

“The man who does something under orders is not unhappy; he is unhappy who does something against his will.”

…on maintaining your free will. There are fewer orders in startups than corporations, but it doesn’t mean you won’t have a boss. Investors are your boss. Do you want to give them the power to control your will, too? No? Then best focus on revenue more than hockey sticks, CAC/LTV, and unicorns.

The death of Seneca

“The gladiator may lower his weapon and test the pity of the people; but you will neither lower your weapon nor beg for life. You must die erect and unyielding.”

Lucius Annaeus Seneca
4 BC — 65 AD

Read the books

  1. Letters from a Stoic by Seneca
  2. Seneca Six Pack: Six Essential Texts by Seneca

Much more to come…

Be sure to follow me if you’d like to receive a notification when the next installment is added.

Thanks for reading,
Aki

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

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