How to win the lottery or have an IPO-ing startup

How do you win when your chances are one in a million? Here are the best approaches to follow and hope for the best:

Strategy 1: play the same numbers over and over again

This is the all time favorite. Of course, it’s a golden shiny example of gambler’s fallacy: it seems to them that each time you loose, the odds to win increase — because the universe balances itself. The universe does balance itself, no doubt, but no balance in your pocket will appear.

In the startup world this strategy is seen in a few places. One is on those really technical startups: technical founders, technical co-founders, technical everything. These people are problem solvers: they like to see something solved. But in order to achieve a solution a new attempt must be made after each failure, and the same thing is being rebuilt all over. You’ll see this with people that develop “personal” projects that are ten years old and they still debug and refactor.

Another situation is with success stories: Steve Jobs made it several times in a row. He first solved the personal computer problem by making them easy to use and friendly, then solved the online music problem by making it easy to use and friendly, then solved the mobile phone problem by making it easy to use and friendly and then he solved the tablet problem by … you get the point.

When you play the same numbers over and over again, you have no better chance to win. However, if the conditions are always the same as they were when the winning numbers were drawn the odds increase considerably. In the Jobs example, those markets, the people in them and the dominating mindsets were very, very similar. Just as deep and blue the PC world was before the Macintosh showed up, such a compact and flat disc the music industry was before iTunes showed up, so the odds for another similar winning shot were really high.

Strategy 2: trying to guess the numbers by thinking really, really hard before choosing them.

This somehow makes the player believe that there is any kind of intellectual asset that he or she can invoke to intuit the numbers. See, intuition is the correct hunch. A hunch is an emotional gut feeling but intuition is not, as wrongly assumed, a gut feeling, but a complete intellectually proven hunch.

In lottery intuition rarely works. Even if your gut is telling you the numbers, you still have the same odds of winning. Nothing you can do about it. But some people like it this way: look at @Ev and his relentless tweaking of this very site. It’s like if he thinks really, really hard about it, then its a sure win. Maybe it will be, be but the odds are the same.

You’ll find in this group many visionaries who have their own capital. You’ll find projects that aim high in perception class like Medium, high in complexity order such as all the myriad of enterprises Elon Musk is into, high in potential like the defeat of death which Larry Page discusses about. The odds are the same.

Strategy 3: lottery as a profession

These people know everything that can be known about the lottery: who won, how many times each number popped up in recent history, the exact pot at every winnable category — you name it. But even more important, they know The Schemes. They scheme day in and day out on how to maximize the winnings and they play really large sums of money with particular number and scheme combinations — the idea is that even if the jackpot is not won they can make a good exit from winning many smaller prizes.

I tend to equate these with VC and Investments Funds and the advising they do for startups. It is all the business knowledge they provide that makes the startup either an IPO or a great sale, but not both. They have mathematical models to describe the potential evolution of a startup, of a market, of individual customers — whatever. Still, while there surely is a living to be made out of this knowledge, they can only slightly decrease the odds of being the big winner.

That is why i like this lottery metaphor: even big shots can’t really have a significant head start as the odds are so small. In the lottery where i play to win, most often there are 15 million number combinations. A person that spends 100 times my expenditure, only buys a mere 90 combinations of those 15 million, so my one and their 90 are about the same compared to 15 million. Mathematically they are not the same, but subjectively its a great feeling of equality.

Strategy 4: asking friends for numbers. And everyone else.

This bunch is definitely the most vocal. From Monday to Sunday they relentlessly try to crowdsource their winning combination. Then, of course, they are confronted with the dilemma of splitting the hypothetical winnings: i played the ticket but he and she told me the — random — winning numbers, so how much do I keep? A problem obviously about ethics that has no mathematical solution, yet they still try to find one.

In the startup world these are the accelerator born businesses or the hackathons generating working products. Of course the odds are the same, no matter who announced loudly the numbers and who jotted them down. But it does feel that the community actively participated. This group of entrepreneurs are the ones that top the Reddit startup threads with questions, those to seek business answers on Quora or those dying to have their dry testing page featured on Product Hunt. You never know if the traction is because of the chance the community gave away, another lottery, or because its actually a great and possibly disruptive product.

Strategy 5: random numbers from a bowl

They had a dream that they won the lottery and now they are waiting in line to pay the price, but didn’t really have the time to come up with some numbers. They mix and mix those bowls that all respectable lottery outlets have and invest a lot of confidence in serendipity. Basically they multiply the randomness of the drawing process with another randomness of the initial drawing process. But never mind, their odds are the same too.

Amusing as it may be, i look at this group and see the horde of idea generating “business” types, the types which are constantly looking for the mythical technical co-founder. It’s always as if having a rock star implementing your genius idea will be “bullseye” in the target of millions. Its not, but they feel like it is. And boy just like the lottery bunch they stir and stir the magic bowl of technical people until the perfect match is, of course, randomly drawn.

Strategy 6: use the force Luke, aka the superstitious group

Oh, yes they play on birthdays, Mondays, the 13th of every summer month, have the lucky stone rub against the lottery ticket, all in all make a whole spiritual project out of it. This group firmly believes that a certain external thing determines the outcome of the draw, something else rather than Heisenberg’s probabilities or the orderly chaos in the universe.

As anti-fragile as this approach may be these people don’t live in Mediocristan, nor in Extremistan. They live in Digitalstan. Their universe is made of highly coupled parts and they all (these parts) have an on and an off state. Push the right switches and you will get the desired outcome.

In the world of Valleystan (or the startup world) you’ll find that there are data driven entrepreneurs who solidly believe that storage and analysis of data is the rope that pulls the IPO in sight. Of course, neither they believe black swans exist, nor that, on average, data shows what everyone else already knew. Well with all the effort, the odds are still the same.

Strategy of strategies: have fun, play once, win

In the country where i currently live the past ten or so jackpots have constantly been won by people who spent one euro in a random day, just for fun. Not all the winners went public but those who did were so oblivious to the other strategies that i couldn’t help but be amazed: no persistence, no data, no schemes, no advice, no superior approaches … nothing.

Just the sheer fun of indulging in the fantasy of huge marginal utility.

This is easy: the Zuckerbergs of the world, the Gates’ of the planet, all those who played once and won the jackpot: from Yo and WhatsApp to the now ancient story of the million dollar homepage.

But they too have had the same odds that you do.

Indeed I like this lottery metaphor so much better than poker or roulette. It is a simple translation for many of the principles that guide the entrepreneur in the modern adventure called startup: minimum viable product, fail early — fail often, do one thing well and others.

If building a successful startup would be like poker then could anyone please tell me: what is the winning hand? No four aces guaranteed the millionaire exit. You may have a royal flush of experts, developers, funds and opportunity and still be lost to history.

Full house? Four of a kind? Probably no casino games work as a metaphor for startup success for one very simple reason:

there is no rule that states you win.

On a secondary note, to me winning the lottery is a visceral experience to be desired. I play because i want to win. Obviously, the money are gonna be awesome too, but the rush of having the jackpot splash in your face at some random Tuesday, well that is something really unique that costs me 1 euro to try and buy: that’s a fair price so I play to win. However this article is not about my lottery indulgence.

Skipping those who don’t play because they don’t trust the system, they don’t think they deserve it or who want to play but keep forgetting, we see that sometimes a lottery ticket has more chances to bring you a nice life than an attempt at some IPO, but aside from the lovely experience of sudden luck it lacks the life and adventure the startup journey will provide, and don’t we all know its the journey that’s important not the destination?

Letter to the struggling creator of anything

Open letter to the struggling creator of anything

Dear creative human,

You are always busy. New ideas, new work, new output every hour after hour. At the end of the day it’s all meant to push you, bit by bit, closer to the place you want to be in. May the place be called “The top of the (collective) mind”.

When you do get in the “top of mind”, with a badge of “known” or “established”, you receive the magic rainbow of: authority, creative freedom, influence and respect — personally handed to you by Roy G. Biv. Let me introduce this place as “The Promised Land”.

Between you and “The Promised Land’s” endless supply of daily joy, the universe has placed a horde of folks which will do anything they can to fight you and your calling. We’ll call these folks “The gatekeepers”.

The place where you are now, nobody cares and nobody will ever care what that place is. In all honesty, I am convinced some people have already answered many fundamental questions and have solved truly profound problems, but we’ll never know they did it — because, like you, they are in this huge, hot, empty and sandy land I’ll call “The desert of anonymous”.

As you hike along “the dunes of unnoticed material” and walk along endless piles made from grains of existential purpose, shattered smoothly by the senseless passage of time, the brief fifteen seconds of fame are the cherished water to wet your lips with — just enough to keep carrying on.

From time to time, there might be an “Oasis of opportunity” hovering above the ground like an unreal vision — some stupid joke Faith keeps repeating and laughing at, all by itself. You’ll enter it, filled with hope. However, while refreshing, the oasis of opportunity is still just a closed circle of friends making some “Promised land” in the middle the same huge “Desert of the anonymous”. Sometimes, even worse, you’ll enter it just to find it shatter when your better judgement gets a hold of you, a fata morgana of creative recognition.

Nevertheless the true wanderer, the berber skilled on surviving anonymity conditions lives with the ordeal. Some have a map, some start out the journey really, really early and some follow the right footsteps “leaning in” the right direction.

Struggling with your hike effort and thirst for audience you will be often spotted by the all seeing eye of the peers. This, just like the one in the famous Mordor in The Story, sees everything and only likes his army of minions. The all seeing eye of the peers is what will always keep innovation at the gates because if, by any chance, you are breaking taboos, shattering established foundations or challenging long held beliefs — you will be scorched. The flaming eye of peers shall spot you and burn you as many times as needed until you either conform or give up.

This is the main foe to fight in the Desert of anonymous and the best strategy is, like in The Story with The Hobbits, to move low profile and decisively act only when the army of minions attacks some other group at war. Being distracted, the all seeing eye of the peers might not spot you just enough to ensure safe passage trough the Desert of anonymous right to the walls of The Promised Land.

Once you’re close be warned: handling all the ancient creatures guarding the walls, lands and gates of The Promised Land means an even greater challenge than crawling all alone and miserable trough the Desert of anonymous. Yet all the truly brave creatives will muster up the guts and force, because they’ve beaten the desert, survived it and at least they got near The Promised Land, having now a chance to go trough what we think of as:

“The Promised Land defense system”

1. The moat of critics

Every wondering soul who didn’t get in, who got tired of trying, who got a really bad fall from the wall, ended up in the moat around The Promised Land. This is the moat of critics.

They are being thrown slices of old bread from the towers of The Promised Land and drink the muddy waters in the moat. They can’t get out because only the Desert of anonymous can be their home since in The Promised Land everyone knows them from the moat.

The technique to pass this first defense is to very carefully bridge the moat: once you fall in no one can pull you out — until you are too old to matter anyway. These folks will shake your bridge and they will throw their mud at you. Simply make sure to walk on determination and hang on inspiration and the swing from the moat’s edge to the Wall Of Publicity will be clear, pure flight. If you get dirty, jump back and clean up because the moat of critics has the stickiest of mud; you don’t want to be stuck to the Wall Of Publicity while the journalists fire their bows at you.

2. The Wall Of Publicity and the towers of journalists

The Promised Land’s towers are filled with journalists aiming at you bows of inconclusive reviews, armed with arrows made of mean phrases and with burning tips of ignorance, all while you strive to climb the Wall Of Publicity, a living wall, made taller and taller by every human who manages to climb over it. Give up fast enough if you’re shot! Just jump back and try another wall.

Walls Of Publicity are usually climbed faster with “controversy” at your belt. Also, a shield made of the highly reflective “sensational!” will blind the towers’ archers by the very sun of the hot Desert of anonymous. If you’re missing “controversy” and “sensational”, then you can always try to catch one of the grown leafy Trends — there are many of them, swinging freely on the badly maintained Wall Of Publicity.

3. The Gate of curators, BDFLs and promised land xenophobe residents

Curators are the noble class and land owners of The Promised Land. They own by right of birth some portion of The Promised Land.

You need their permission to cross their land. Those who own the outskirts of The Promised Land are the most fierce in their terms for the permission, since every wall jumper ends up in their backyard begging for a visa.

Once you’ve jumped the Wall Of Publicity the way around curators is to walk the public roads. Considering the curator’s terms, spending the night under a street spotlight is usually far better than spending the day on a privately owned part of The Promised Land.

Benevolent dictators for life (BDFLs) are traders who take stuff from the “Oases of opportunity”, and bring the stuff in The promised land.

Remember them, the “Oases of opportunity”?

Sometimes these oases produce some uniquely fine idea, or even a superfine concept, which either the opportunists or the brave take to The Promised Land’s fortification. If what they bring is of value to the residents of The Promised Land, they live to become BDFLs on the trade route of creativity that they have founded. The problem with these is the dictatorship part: you do it because they say you have to do it; they do it because they know the route, they have the contacts and the influence.

You might want to stay away from these smugglers of creativity and try to make it on your own. Otherwise, be prepared for some years of mental slavery before you’re finally given your part in the bargain.

Your next problem: some of the The Promised Land’s residents are xenophobic. They are those who suddenly learned that whomever lived longer inside the The Promised Land, clearly must be better beings than those beggars from the sands of the Desert of anonymous. Unfortunately they own the third Gate.

Some of these xenophobes are born inside The Promised Land and some, just a few, a tiny faction, really are better, better than anyone other than themselves: they are the geniuses, the ultra productive, the prolific creative machines, the singers of the word of God — or something of sorts — those who did not have to struggle one day to learn anything and yet they’re simply outstanding. What the xenophobe residents will do is mock your normality and call it mediocrity, blissfully ignorant at the side of your creation that is special and unique, made better by each hour you’ve spent working hardly on it.

To avoid being held at The Gate, disguise. Walk confident, make a friend who lives on the other side, talk to people who come out and who go in — a clear strategy:

learn the culture, move like an insider and speak the subculture.

If you’re acing all these, no one will ever ask a thing. Not who you are, nor where you’re coming from and all the gates will open like you said “Sesame!”.

Once you have entered trough The Gate, well, that’s it! Bravely step in and rejoice! You have found The Promised Land and Roy. G. Biv. awaits you to hand over your very own special rainbow. Huzzah! Yay! Hooray! Oh, and once you’re in, dear creative human, please do write me a letter and ask a dove to deliver it to me. The dove will find me — they all do.

Now that I’ve made enemies of about each type of people guarding The Promised Land, by revealing their wicked ways and doubtful days, and since I despise the Desert of anonymous so badly, I think I may strive for the remainder of my days to find that spring of creative youth which I know it to be somewhere at the edge of understanding. Send the dove there before I reach the spot.

The doves always find it first.