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?