Startup Lessons from History: Napoleon

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 ambition personified, in Napoleon the Great.

Previous 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.


Say what you may about the man, but he’s right up there with the most ambitious people to ever live and breathe on this Earth. There’s him, Julius Caesar, and maybe Alexander the Great.

Should we in fact refer to him as Napoleon the Great? Some argue yes, given that his aims were certainly more noble than Alexander’s. The reason there’s a counterargument is mostly due to the fact that after he took control of the French Revolution and it’s aims for liberty, he kind of kept all of it. To himself. Liberty and such.

You could also totally see Napoleon in today’s world, running a unicorn or tech giant with his iron fist inside a velvet glove. Few opponents in history could resist his combination of panache and wit as sharp as an imperial rapier.

Napoleon nearly conquered the world, twice, but came up short both times. What was taken away from him was the singular focus and meaning of his life, pure and unlimited ambition. In the end, imprisoned for life without hope of further conquest or achievement, he passed away quietly at the age of 51.

Here we go…

“Impossible is a word to be found only in the dictionary of fools.”

…on your crazy/stupid startup ideas. Are they only crazy/stupid, because you think other people would think so? Are they only crazy/stupid, because they seem outrageously ambitions given your experience and skill set?

What small experiments could you perform to validate these assumptions?

#1: Pitch the idea to 10 people you know from diverse backgrounds? Are they potential clients or not? Are you looking for YES/NO or perhaps a “but…”?

#2: What research could you do to judge the actual feasibility of it? If there’s a gap in skills, could you talk to someone with that skillset to get an opinion?

If the experiments are positive, what’s the next step you can take? Market research? Learning new skills online? Even building a mockup or prototype?

“The fool has one great advantage over a man of sense — he is always satisfied with himself.”

…on hunger. You meet few respected, accomplished people that are genuinely pleased with where they are. They should’ve done more. There’s so much left to do, we’ve just started. All the things we could do if we just had more resources. How much further we could take our vision if we hit the next few milestones. Eternal dissatisfaction is the food of the founder’s soul.

“Glory is fleeting, but obscurity is forever.”

…on the probability distribution of your success. It’s low, but non-zero if you’re on the curve. So start, and get on the curve, at least. Luck can only happen to those that participate in the game.

“Nothing is more difficult, and therefore more precious, than to be able to decide.”

…on failing fast. The early decisions in any startup are exponentially harder than anything you’ll face later on. What’s the name going to be? How will it reflect the companies vision? What is the vision? Is this a problem worth solving? Is there a bigger problem, that would tie better with this awesome logo I’ve just sketched on a napkin?

The challenge lies in an unlimited decision space. On Day 1, you can literally do anything. It’s hard to decide on a something. Once you make your first 5 decisions, all other decisions are now limited within the decision space of those 5 previous decisions. Instead of infinite possibilities, you just need to decide between 10 or 100 alternative scenarios. It starts to fit inside your brain. At some point, the decisions become so narrow that you can actually model them on a spreadsheet, and calculate the right answer.

“A soldier will fight long and hard for a bit of colored ribbon.”

…on strike prices and cliffs. No matter how you artfully craft your ESOP, it should never be the reason why people stay. There should be a story, a narrative that keeps them thinking about your business. Not because they are well compensated for it, but because they want to. On top of that, think about recognition. When people go out of their way, how do you incentivize that? Often the best place to start isn’t with the Benjamins, but by saying it. You did a good thing. Thank you. Your work is really important. Hey everyone, this was a really good thing for him/her to do.

“It is not that addresses at the opening of a battle make the soldiers brave. The old veterans scarcely hear them, and recruits forget them at the first boom of the cannon. Their usefulness lies in their effect on the course of the campaign, in neutralizing rumors and false reports, in maintaining a good spirit in the camp, and in furnishing matter for camp-fire talk. The printed order of the day should fulfill these different ends.”

…on the big moments. When the team disperse back to the water cooler after your well-prepared and rousing speech, is when culture happens. Talk less, but more often. The rest, as they say, is history.

“Always carry champagne! In victory You deserve it & in defeat You need it!”

…on learning both ways. Embrace your inner stoic, and celebrate wins and losses with equal dispassion. The only thing you can do by going crazy in victory and defeat is either passing the wrong values to your team, or losing your team. The fight is every day, not the big moments.

“Never ascribe to malice that which is adequately explained by incompetence.”

…on the value of NDA’s and MoU’s. As little as you as the founder know about where your business is going, how can you expect 3rd parties to predict your future? You will laugh at the plans and assumptions you made last year. That partnership was never going to fly. Our roadmap was heading 180 degrees in the wrong direction. So don’t sign speculative agreements, period. If you have no choice, make damned sure the NDA is mutual without any I.P. or penalty clauses, i.e. totally meaningless and unenforceable.

“Only give them history books. Men should read nothing else.”

…on perspective. News gives you useful information hidden in an infinite sea of noise. History, both near and far, gives you the edited version of news as a completed narrative. You can use such narratives to inspire chapters of your own story.

“Never interrupt your enemy when he is making a mistake.”

…on stealth mode. The trouble with not telling anyone anything about what you’re doing, is that you limit valuable feedback from the market. Stealth mode is the best thing that could happen to your competitors, allowing you to make an endless series of mistakes, and likely dying into obsolescence before your imaginary launch window.

“Imagination rules the world.”

…on storytelling. Yoav Harari would say that’s all we have. The whole world we know and everything in it is an invented narrative to get ever growing masses of humans to collaborate as participants in those stories. Money. Government. Nations.

So what is your story, that will bring together your team? Will your story capture an audience of customers? Of media, of investors? Get your story right, and the world will follow you.

“Ability is nothing without opportunity.”

…on product/market fit. It’s great if you can solve a problem, but if nobody yet has that problem, then what’s the point? Unless you’re Elon, the rest of the world still operates in a short-term fiscal economy. Investors like blue ocean strategies, where you create a new market or even monopoly. But let’s face it, selling pizza on Mars isn’t gonna break even anytime soon. There’s a difference between a blue ocean and wishful thinking.

“A leader is a dealer in hope.”

…on hockey sticks and happy endings. One of the bigger burdens to carry as a founder is that the real truth is rarely known to anyone but you. The narrative you create to support your growth manifests itself in different forms to your team, your investors, the media, your family, and your friends. They all expect a bright future, filled with hope of awesomeness and achievement. Your job is to manage all those expectations at a level that is sustainable. Too high? The house of cards gets wobbly. Too low? Nobody cares. That’s the story behind the story.

“Victory belongs to the most persevering.”

…on battles versus wars. Did you really lose, if you lost your first pitch competition? Your 10th? Did you really win if you won a free pilot trial? It’s all a matter of perspective and timelines.

Do you care about winning the battle, or winning the war? There is no such strategy as winning every battle, unfortunately. Even for Napoleon, certainly not for you. So pick your battles.

“He who fears being conquered is sure of defeat.”

…on asymmetric risk. Take no risk, there can be no reward. Free markets will take that decision away from you, so don’t worry about it. Instead, look for risk where the reward is asymmetrically high. Risk 1 to gain 5. Never risk 5 to gain 5.

One easy source of asymmetric risk is your time. That could be a definition for the beloved “hustle”. Risking all 48 hours of your own weekend is acceptable. Even risk the 2,496 hours of all your weekends in a year. Risking paying rent is not acceptable.

“Courage isn’t having the strength to go on — it is going on when you don’t have strength.”

…on burning the midnight oil. If you haven’t been there yet, you might as well bookmark the local 24/7 pizza delivery now. Whether your first demo, or your next release, startup tech will always exist on the sharp edge between acceptable and embarrassing. If you’re never hitting the rocks, you’re probably playing it safe, and competitors will catch up. Even Zuck used to break things back when he was still cool.

“The reason most people fail instead of succeed is they trade what they want most for what they want at the moment.”

…on instant gratification. This is a dangerous habit to feed in the world of startups. Investors will push you like a slave in the galleys until you’ve delivered their 3x liquidity preference.

“The greatest danger occurs at the moment of victory.”

…on setting expectations. While spinning your growth story, it’s all too easy to talk up your metrics, your pipeline, your big deal that’s about to close. The trouble starts when you build a glass tower on top of thin ice. You could keep the narrative alive by explaining a bump, but if you spin the thread for too long you risk having no solid ground to land on.

“China is a sleeping giant. Let her sleep, for when she wakes she will move the world.”

…on picking your wars. Not only Napoleon on the money here, but in retrospect, he should probably have applied that same logic to Russia, too.

While everyone likes to see a hockey stick growth curve, you will have an obligation to win the wars you pick. As a startup, you can lose battles, but not wars. If you’re really out there to make a difference, you should play the long game. There is no benefit to almost making it big for your customers, despite the best wishes and intentions of your board. There’s a difference between calculated risk and straight up betting the house.

“Circumstances-what are circumstances? I make circumstances.”

…on that one lucky break. Your job is to put yourself, and your company, into a position for luck to happen. The more you engage with your ecosystem, the more lottery tickets you are granted. Every event, every press release, every pitch, is a ticket. How many tickets until luck becomes more than 50% probable? 1,000? 10,000? It’s a finite number. So start getting lucky!

“It’s the unconquerable soul of man, and not the nature of the weapon he uses, that ensures victory.”

…on your best-in-class CRM and accounting software suite. Zero deals will be generated by your CRM. Zero cashflow will be generated by your automated forecast reports. Don’t spend any time or effort on tools, even free tools. That’s how corporations waste all their focus, time, and money. By managing “Excel money” and forgetting about the real world and customers. The results will come from you, nowhere else. Stop creating excuses for your team to take comfort in.

“To understand the man you have to know what was happening in the world when he was twenty.”

…on building a team. While your Bon Jovi vinyl collection might’ve been hot stuff back when you were hot stuff, you may find your millennial colleagues tagging you in #lol memes. You’ll have to learn to relate on their terms.

“From triumph to downfall there is but one step. I have noted that, in the most momentous occasions, mere nothings have always decided the outcome of the greatest events.”

…on the difference. You’ll have ample opportunity to give yourself a break here and there. Whenever facing that seemingly innocent gimme, ask yourself if it’s worth losing over. Just do it. Just in case.

“He who cannot look over a battlefield with a dry eye, causes the death of many men uselessly.”

…on breaking eggs. You’ll have to fire people. Customers will send you nasty emails on Sunday evening. Media will misquote you. Think of it this way. Everyone likes the omelette station at the hotel buffet. Be that guy.

“There is no place in a fanatic’s head for reason to enter.”

…on the fine line between admirable persistence and plain stupidity. Peter Thiel likes idiosyncratic, stubborn founders. Steve Jobs would say to hire smart people that tell you what to do, instead. There’s a golden middle there, somewhere, of the type of character you need as a founder, and what type of people you need to surround yourself with. A dictator with an army of yes men is probably a bad idea, unless your business model relies on staging a coup.

“To PRINCE MURAT, I cannot find words to express to you my displeasure.”

…on constructive feedback. Corporations may have room for shouting, since venting frustration is the only way to maintain your sanity as a cog in a giant wheel within the cubicle matrix. In a small startup team, you’re all sharing the same reality. You can’t blame the muppets in pre-sales or accounting. Every failure is a team failure, and every failure stops with the founders. If you enjoy shouting matches so much, take up a useful hobby like street fighting instead.

“The laws that govern circumstances are abolished by new circumstances”

…on the value of your 62 page business plan, with stylized section headers. It’s worth it’s weight as paper airplanes the moment you tap the last keystroke. Then again, your could replicate all four terminals at Heathrow International with 62 pages, if you forgot to go 2-sided. That would be pretty sweet.

“The men who have changed the universe have never gotten there by working on leaders, but rather by moving the masses. Working on leaders is the method of intrigue and only leads to secondary results. Working on the masses, however, is the stroke of genius that changes the face of the world.”

…on B2B2C. If there’s no “C” at the end of your go-to-market strategy, are you thinking big enough? Is this something you would do, if you weren’t paid a dime to do it? Not that your corporate tax accounting platform isn’t cool, just that the universe is unmoved. You probably are, too.

“To have ultimate victory, you must be ruthless.”

…on the price you’re willing to pay to win. I’m pretty sure it was cool to be Napoleon, but it probably sucked to be around him. Let’s face it, Napoleon didn’t win in the end. In fact, he lost everything. Twice. Maybe if you toned down that last 10%, you might live to tell the tale, and have a loyal team around listening.

”You cannot stop me; I spend thirty thousand men a month.”

…on burn rates. This is really ABC of the startup disruptor. There’s few things in life that couldn’t be improved upon with a hungry dev team and throwaway marketing spend.

For more Napoleon, check it this amazing four part documentary by PBS:

“Sirs, if it were not for that one red spot I would have conquered the world!!”

Napoleon Bonaparte

Read the books:

Much more to come…

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Thanks for reading,