# The Struggling Startup Quick Guide
This is a curated list of essays about startup life
**Table of Contents**
[[The Struggling Startup Quick Guide#Go All The Way|Go All The Way]]
[[The Struggling Startup Quick Guide#Guts and Moderation|Guts and Moderation]]
[[The Struggling Startup Quick Guide#Tame Your Ego|Tame Your Ego]]
[[The Struggling Startup Quick Guide#Learn to Tell a Story|Learn to Tell a Story]]
[[The Struggling Startup Quick Guide#"What's in the Box?"|"What's in the Box?"]]
[[The Struggling Startup Quick Guide#Iterate|Iterate]]
[[The Struggling Startup Quick Guide#Interoperate|Interoperate]]
[[The Struggling Startup Quick Guide#Shock Your Audience|Shock Your Audience]]
[[The Struggling Startup Quick Guide#Tango|Tango]]
[[The Struggling Startup Quick Guide#Choose Wisely Your Partners in Crime|Choose Wisely Your Partners in Crime]]
[[The Struggling Startup Quick Guide#Wins, Flops and Statistics|Wins, Flops and Statistics]]
[[The Struggling Startup Quick Guide#Take Proper Notes|Take Proper Notes]]
[[The Struggling Startup Quick Guide#Mind the Long Tails|Mind the Long Tails]]
[[The Struggling Startup Quick Guide#The Rich Get Richer|The Rich Get Richer]]
[[The Struggling Startup Quick Guide#Shit Happens|Shit Happens]]
# Intro
There are no saviors. Your startup will get out of the hole only through your and your team’s ingenuity, perseverance, and, fundamentally, cohesion. Or it won’t.
Then, you may say, why even bother to continue reading? Well, here, I speak from my own rabbit hole, so my experience, although different, may still help. I aim to provoke some thinking. That is all. Thinking is key, you’ll see. Perhaps the most important thing. There is no possible way out of the shit hole you are in without thinking. Thinking of the biggest picture you can think of, thinking about how to connect the loose dots. Unless you expect some _Deus ex Machina_, i.e., a miracle. If that happens, call the Vatican or an exorcist.
Instead of waiting for a miracle, maybe take a quick look at these articles below, you may find something. The clock is ticking, I can hear it, you can hear it. So I will keep it brief so we can go back to work and sell stuff. In the meantime, avoid the dilettantes who write from their offices at Ivy League business schools those nice-looking 700-page books about how to run a startup. They don’t know; they speak from comfort, which we lack. Avoid the troubled young millionaire with an existential crisis who writes about how he made millions and lost _everything_ being reckless, but is still awfully rich. Avoid the best-selling guru who puts his face on the cover of his book about leadership, hand in chin. Stay away from all that bullshit. Sounds good, doesn’t work. At least I am being honest here: I have no clue what I’m doing in my startup, but I’m trying. I’m in the arena. I have tried some things that worked, and some others which didn’t. I’ve learned a thing or two in the journey, which by the way is far from being over.
Every section in this note aims to be a sort of reminder. An earworm, playing in your brain at all times. Or a gadfly, buzzing. That’s what I aim for. To pick your brain. I hope you will end up hating me because you just cannot stop remembering the things I am telling you to mind in the incoming pages.
By the way, I am a technical guy. I have been doing software and systems for a long time. Things which can cause trouble if they don’t work. I currently wear a CTO hat in the startup I am in. Hence, the tone of the text revolves around a CTO-esque perspective: product design, complexity, decision-making, engineering. It does not dive deep (or at all) into fundraising, business models, or financials. I believe that good engineering begets money. Or, begets consistent money. Smoke and mirrors can get you by for a while, but not forever.
Last but not least, you are probably wondering how I got myself into this situation. Before being in this mess, I was a VP in a larger company. You know, a manager. I was comfortable. I was respected, I used to enjoy the cushy job. For a while. Until I felt an itch: I was building nothing: I was just talking, and talking, and talking. So I did what I tend to do in general: dynamite what I have painstakingly achieved with patience, time, and passion, and move on, pursuing an amorphous idea, seeking to get my hands in the dirt again. I have no sunk costs. Nor do you, I reckon. I believe we are in this game to bring order to the chaos. We love the chase, we are bored with the conquest. We are here to create things that work whenever we turn them on and keep on working, and working.
May the chaos eventually become order, or we will perish in the process. Off we go.
# Go All The Way
When I was maybe 5 years old, I was ready to leave behind the training wheels of my bike. I remember I was in La Lucila del Mar (~350km south of Buenos Aires) where me and my family would go for summer holidays. I vividly recall the thrill of thinking about riding the bike as older kids did, but I also do remember the frustration after falling and getting hurt while trying to do it, although I was trying quite carefully. Things were not working great, so my grandpa warned me: “you’re going too slow, you’ll keep on falling unless you gain more speed”. His advice sounded a bit strange to me, like, opposite to what I would’ve thought. As if my careful approach was actually part of the problem. So, given that I hadn’t achieved much in my own ways, I decided to give it a go so I went higher up the hill I was practicing on. I can't say it worked out the first time (and falling at higher speeds was not precisely amusing), but I could see that the higher velocity made things somehow better, so I felt it was worth risking more. It took me a few extra bruises until I figured it out; I still remember the joy when I finally nailed it.
Many things work in a similar way: they need an initial buildup to overcome a stalled or disaggregated state and sustain operation, which also comes with some risks attached. Airplanes would only generate enough lift to sustain flight provided enough thrust can ensure a proper speed. Think about how stars form in the sky. As the Galaxy is filled with clouds of gas (huge aggregations of cold hydrogen), gravity pulls dense regions into collapse, which the cloud resists until it is unable and begins to contract. As it collapses due to its self-gravity, it compresses the gas further, causing it to heat up. Eventually, most of the matter accumulates at the center, and the central sphere, now a protostar, continues to contract and heat. As its temperature rises, more and more of its hydrogen ionizes, that is, the atom loses its single electron. Free electrons scatter and absorb photons, so the more electrons that are liberated, the more opaque the protostar becomes. If photons cannot escape from the gas, their energy is trapped within the protostar, causing the temperature to rise even further. If the temperature within the core rises to a sufficient level, it ignites nuclear fusion which provides the pressure required to prevent further collapse. A new star is born. Notice all the things that must take place for a star to exist. Too many, right? Too unlikely? Not quite. As Freddie Mercury sings: look up to the skies and see. Billions of stars. The power of scale. Think about this when trying to get into a crowded market. There can always be a new star, but you must come up with something truly stellar.
The startup journey is like trying to leave the training wheels of the bike. Intuitively, one wants to play it safe, but at the same time you know the only way to make things ignite is to climb higher up the hill and let your body gain kinetic energy while keeping eyes wide open on the road ahead. And if you fall (and you will fall), you shake off the (star)dust and try again until you leave the place riding like a boss and shining like a star.
As Charles Bukowski wrote in _Factotum_ (1975):
_If you’re going to try, go all the way. Otherwise, don’t even start._
# Guts and Moderation
Nordic countries are admired around the world. According to a broad range of indicators, the Nordics rank at the top of international comparisons measuring, among other factors, happiness, gender parity, income distribution, human freedom, and press freedom. Other countries look up to the Nordic nations to find out the reasons for this. Without pretending to do any sociologically deep analysis here on the reasons why the Nordics do so well compared to others, at least everyday life in a Nordic country has given me a reasonably good perspective on how some Nordic cultural concepts are, perhaps not the sole explanation of all this, but surely great contributors.
One of those concepts is _sisu_. Sisu is a Finnish word that has no possible translation (as many other words in Finnish…). Sisu appears to be a combination of tenacity, courage, and guts; but it is more than that. Sisu is very embedded in the Finnish culture, and it has been a great collective driver during difficult times. A startup knows very well about difficult times, so _sisu_ is something that every entrepreneur or startup member should embrace. Things will go ugly quite often, things will fail, rejection will be frequent, ideas will be received with disbelief and disdain, and effort will seldom be proportionally rewarded. You know, fighting from a trench dug in the long tail. When all that is going on: sisu, and carry on. Next time your idea does not go through, gather some sisu and try again. Next time you get an email starting with “we regret to inform you...” or “we loved your idea, but unfortunately...”, sisu and don't let go.
If you believe in the shit you’re after, sisu: fight.
The other term you need to know is: _lagom_. Lagom is a Swedish and Norwegian term that means: "in its right measure", or "just the right amount". Lagom is about finding balance through moderation: take just enough of what you need in order to do well without going over the board. The Swedish proverb, “Lagom är bäst”, literally means, “The right amount is best” but is also translated as “Enough is as good as a feast”. There is virtue in moderation. Startups must be moderate. Think of lagom. Think about lagom when you design, when you write, when you talk about yourself, when you lead when you write.
Startup life is plagued with challenges and tough decisions. A blend of both _sisu_ and _lagom_ is a great Nordic potion to face the uncertainties and challenges you surely are facing and will face. The right amount is best. And fight.
# Tame Your Ego
There is a famous joke in South America that goes like this: “If you really want to make a profit, buy Argentinians for what they’re actually worth and sell them for what they believe they’re worth”. Another joke says: “The most efficient way to kill an Argentinian is to take them up to the top of their egos and push them”. This is reasonably unfair, as most of these over-generalizations are, yet funny. In Argentina, there is a belief that our reputation abroad has been somewhat dented by the behavior of a small group of objectively arrogant big-city dwellers. But here we are. As the phrase goes: it takes many good deeds to build a good reputation, and only one bad one to lose it.
What is ego anyway? This section is not about ego in the Freudian sense. Freud was fond of explaining the ego by way of analogy —our ego was the rider on a horse, with our unconscious drives representing the animal while the ego tried to direct them. Modern psychologists, on the other hand, use the word “egotist” to refer to someone dangerously focused on themselves and with disregard for anyone else. All these definitions are true enough but of little value outside a clinical setting. The ego we see most commonly goes by a more casual definition: an unhealthy belief in our own importance. Arrogance. Self-centered ambition. Ego is that intangible, strong self-assurance of our own prominence. A biased self-perception leads us to believe that things revolve around us, that we are better than, bigger than, wiser than. It’s the gap between the price we think we’re worth versus our actual market price.
Copernicus stated some centuries ago that nothing indicates we occupy a privileged spot in the Universe. His theory caused a few waves back in the day, mostly because it challenged theologically originated theories which stated that Earth was the central thing (ultimately anthropocentric theories). Copernicus's theory's most itchy takeaway was and still is: everybody chill, we are not that special.
And this is mainly because the Universe, at the largest scale, shows no hierarchy: basically it’s all quarks and fundamental forces. Gravity does not really give a damn if you are a composition of neutrons, protons and electrons, atoms, cells, tissues, organs. Gravity pulls all the particles you’re made of the same way it pulls the particles your dog is made of; gravity does not understand nor cares where you end and your dog begins, and the same applies for all other fundamental forces: a given point in the Universe holds no privilege compared to another point. Equality at its best.
But on this planet, and more specifically in Society and in organizations, we had the marvelous idea of inventing hierarchies, which are like small artificial planetary systems and such arrangements are fundamentally, bear with me here, non-Copernican: there are indeed privileged observers, who occupy very special places. Not two chairs picked randomly in an office may hold the same privileges. It will depend which chairs you pick. Companies form stars of sorts, and such stellar status can form stellar egos. In reality, we are *all* equipped with our egos, regardless of where we sit in the hierarchy. It is just that hierarchical systems empower and enable a small few to fully flex and feed their egos whereas it will forbid many others from even considering trying. Inequality at its best.
Richard Feynman said that the first principle is that you must not fool yourself and that you are the easiest person to fool. Our egos fool us by setting expectations that are disconnected from objective reality and create internal, individual agendas that collectively seldom add up. What might be best for the collective may (and frequently will) collide with my own personal assessment of how that affects or benefits me, and I might decide to choose whatever massages my ego instead of choosing what’s best for the greater good.
The relationship between ego, talent, confidence, and competence is a tricky one. Someone confident and highly talented can be mistaken as having a big ego, and vice versa. You may think that it could be “allowed” for someone to have a big ego because they have accomplished a lot, or because they know a lot.
Wrong.
On the contrary, true achievement begets humility. The more someone has genuinely accomplished, the further their ego shrinks. Mainly because true achievement implies that you have gone a long way learning, failing, trying, dealing with the elements, and, finally, succeeding. Going through all that should make you very aware of the complexities you have managed to overcome, the alliances you have had to form, and the odds you have managed to bend. If you still see a strong ego from someone theoretically considered an “achiever” or a guru, it might be an indication you’re actually in front of a lucky one who probably rode a stroke of luck or is just in a privileged spot. Or, maybe someone who just suffers some emotional impairment: the glorified difficult “genius”, who tends to lack the basic emotional skills to contribute to the collective with their talent in a healthy way. Inflated, bloated egos can be facades; false fronts built to hide behind, because of reasons. A scenography in a perpetual state of maintenance. This manifests in multiple ways: inability to take criticism, defensiveness, constant rank-pulling, and empire-building.
Ego can be a ballast. And I am not here for the mindfulness-esque “get rid of your ego” type of bullshit. You can’t get rid of it. It’s there, and will stay. Just be aware of it, for it is riding the horse most of the time. Think of Copernicus next time you feel you are a special snowflake. Your ego could be feeding from a privileged spot you’re currently occupying, which won’t last forever. The landing may not be gentle.
Ego pulls hard. It keeps organizations in pseudo-Brownian motion: a motion governed by the internal agenda of each member with an energy proportional to the gap between what they believe they’re worth, versus what they are actually worth.
Ego is the enemy of a struggling startup. Mind it. Put it in a cage.
# Learn to Tell a Story
There is a phrase (from either Oscar Wilde or George Orwell, it’s not clear) that goes: “if you cannot write well, you cannot think well”. Writing is a superpower. Having the ability to put words in a way that make sense is a strong indicator of a functioning brain. But this is a sort of loop. You also think well _because_ you write well. Writing allows you to see your thinking in words and sentences, and that reflection feeds back into the idea which originally spawned the words. When you write, and I am doing exactly this while writing this section, you come back to the paragraphs on and on, you check if the words represent what you thought, and if not, you remove things, add new things, adjust. You may spend hours thinking about removing or not a single word, or a comma. It happens, and it can be daunting. When writing, fiercely fight typos and bad grammar, not only because they look terrible but also because they give the message you don’t pay attention to details, nor you feel bothered to listen to what the autocorrect is surely spotting and warning you about.
If you are a CEO or a CTO, **your main job is to think**. Nothing is more important. You may work on business models, or product architecture; you may code every now and then, or go to a conference. That’s fine. But that’s not your core job. Those are auxiliary things triggered by your thinking. You are a thinker. As such, you must think about everything; where your organization is, where it’s supposed to go, what worked well, what did not. Who, what, when, how, why. This is your job. Strategy is a glorified synonym of thinking. But people can’t listen to what you are thinking. So, writing is your only way of conveying what it’s in the gray jelly you carry inside your skull. Write. Mind that this does not exactly mean publishing. You can write for yourself, or internally in your company. But get comfortable with words, phrases, and clarity.
Overarching writing and thinking, it’s storytelling. You can be the best writer, a superb thinker, and still lack the capacity of telling a story. Storytelling means connecting ideas in a way they follow a narrative which matches whatever it is that your organization is doing, but connecting them in an attractive way. Storytelling augments reality by sticking things together so they are more than the sum of the individual contribution of those bits.
Time is king. Everyone is busy. Here’s some news: nobody wants to read your deck. That’s a fact. So, you better come up with a great story. You need to capture attention, come what may. Attention is the real asset these days. So, better think of a solid story that will make them stop staring at their phones and feel they must look at the slides. Those slides must bring them on the edge of their chairs. Nice colors, logos and fonts help, sure. But the story is king. The story has to be quick, clear, compact, and it must be awesome. It must define what the damn problem is, how the whole thing started, and more importantly it has to show why you have chosen to die on that hill. Your deck is like the trailer of an action movie. Your startup is the movie.
But how do you do what? How do you tell a story? Well, just like Steven Pressfield says in _Nobody Wants to Read Your Shit_, like in movies. Build the tension, and then pay it all off. That’s how jokes are told: setup, progression, punch line. That’s how any story is told. Have you ever tried to seduce someone? The hook, the build, the payoff. Theater works in three acts, Shakespeare as well. Do you know something they don’t?
# "What's in the Box?"
There is a pizza place close to where I live, called “Parmesan”, run by a very affable bunch of young lads. Everytime I go to eat there, I can’t help feeling a bit jealous. Not because of their youth and majestic hairdos, but about how clear the product is for them. They make pizzas, that’s what they sell. Simple as that. Zero ambiguity. They define flavors, toppings, variants. They make people happy by selling warm flat tasty discs with cheese and stuff. Mind you: not everyone has the luxury of such clarity. It’s so clear that If you go to any pizza place and ask anyone working there what they sell, they will all say the same: we sell pizza, what a stupid question to ask, sir.
Now, think about someone randomly entering the office space you currently work at. Picture this hypothetical visitor picking up someone from the team and asking: what the hell it is this startup is selling? And then this mysterious visitor goes to the next guy in the team and asks the same question. What are the probabilities both answers exactly match? If the probability is close to zero, then there is no understanding whatsoever what the startup is selling. That’s the situation usually at very early stages: an amorphous idea does not automatically map to a product. Then, if the probability of matching answers is close to one, I bet you are selling pizza, or shoes. For tech startups, the probability of the answers matching in the “random office visitor test” floats happily in between 0 and 1. And the visitor has only picked two guys from the team, what if he picks 10? The probability decreases, just as it decreases when you flip multiple coins and expect them to land on heads or tails.
Here’s the thing. You must unambiguously find what your product is. You need to bring the probability of matching answers to a solid 1, just like in pizza places. You have to find your thing; the thing that you ship. There is nothing as clarifying and satisfying as knowing what the hell it is you are selling. Everything becomes clear, unambiguous, concrete. You can’t tell a story out of a nebulous idea. No one is after formless ideas. Abstractness doesn’t sell. Products sell. Form and function sell. Find it. Test candidate products. Create brochures, reach out to potential customers, collect feedback. Calibrate.
A silly exercise I used to do: think about a semi-truck full of boxes or crates with the logo of your company. The semi is about to depart to deliver your product to customers who ordered lots of them. Now ask yourself the same question Brad Pitt asked in the movie “Se7en”; try to imprint the same dramatic output if you can: _what’s in the box?_
# Iterate
Dwight Eisenhower famously said: “plans are useless, but planning is essential”. Another one goes: “no plan survives contact with reality”. Most plans you’ll set up in your startup will end up detouring badly, for reasons. Funding, market, whatever. Things will meander. It happens. Still, observe carefully the winding trail you leave behind, because it talks. Picture you are on thick snow, and think you get the chance to see from bird’s-eye view the path you’ve taken up to the point you are today. What do you see? You see a straight line? Of course not. You see circles. You surely see a zigzag resembling a drunk person’s sinuous walk. You see some trails being deeper than others: you revisit some places multiple times, whereas you barely go to some other places to never come back.
But only looking at your actual trail is not enough. Contrast how the path turned out to be versus what was initially planned for. You will not only have a good laugh every now and then (“geez, what the hell were we thinking?!”) but you will be able to extract information from the detours.
How to prevent frequent deviations? Easy. Guess less. Try more.
Shepherding the creative early phase of product design can be excruciating. The main hurdles lie mainly on constraining the problem space (which can be huge), defining baselines on top of continuously changing requirements, but also on gathering meaningful feedback. Product design can never be an open loop endeavor. It’s critical that you put your designs under critique often, seeking for early warnings.
Design critiques (colloquially called _crits_) are a great way of collecting such feedback. You must run _crits_, and you must run them frequently. But, what is a _crit_?
A _crit_ is a gathering where stakeholders (as in, anyone who will suffer if the product does not see the light of the day one way or another) meet to discuss how a design fits (or does not fit) in the grand scheme of things. With considerably less etiquette than formal reviews, during a crit designers “show and tell”, aiming to minimize the amount of guessing. But for design critiques to be meaningful, a set of clear technical performance measures must be agreed upon. Figures of merit are of paramount importance to gauge technical designs objectively, or for bench-marking competing alternatives. Designing complex technical products requires innumerable trade-offs, and performance measures (for example power, weight, volume, range, etc.) act as beacons designers can use to see in the fog of uncertainty. Without such measures, crits can go too subjective, not giving enough substance for designers to recalibrate. On the other hand, unilaterally created, artificial performance measures can lead to designers to fool themselves on what’s important vs what is not from a customer perspective. Mutual agreement on these is essential.
Design critiques have the ultimate goal of drenching all stakeholders with information they can use to adjust the course of a product design before it gets too heavy and costly to make a swerve.
# Interoperate
Picture a parallel Universe where any data produced by any product can be directly understood, processed and augmented by any other product or system that has complementary capabilities the former system does not have.
This hypothetical scenario belongs to an almost unthinkable Universe where all human-made products are not only capable of talking to each other but also capable of using the information they exchange, where interoperability and collaboration are always present, by design. A Universe that could be (or could have been) but it is not, and perhaps will never be. It appears, it is in our best interest to continue creating isolated products. Some forces that shape these artificial bubbles are:
- Protection, which comes in different flavors: data protection, intellectual-property protection, privacy protection, and access protection. Largely driven by competition and regulations. Note that this is not a synonym of encapsulation; we can have a properly encapsulated product capable of interoperating.
- Cost saving: as in, both financial and time costs. It appears cheaper and faster to do things without caring about what’s behind the door.
- Market dominance: the maker of product A does not feel very attracted to the idea of giving the chance to other commercial actors to interface with their product and make a profit; i.e, share the value chain.
- Consensus: if we want product A from entity X to talk to product B from entity Y, we have to get entities X and Y to sit down and discuss how to. Moreover, if we want other entities to be able to eventually join, we must open that conversation up. This is, in a nutshell, the standardization nightmare. Standardizing is a hard thing to do, and very human oriented. Too many standardization efforts become complex contests between corporate wills. Too many standards become a mess too quickly.
Not surprisingly, the lack of interoperability in the products we make is the result of our intrinsic self-interest. But, we don't even care about organizational boundaries when it comes to unleashing our selfish behavior. We also design and grow insular products and structures inside a single organization.
But hey, _c’est la vie_: we are selfish, we strive for our own benefit, and it will always be this way, right? Sure, all is good and great with that. Depending on where you are in the food chain.
Collaboration is the only real weapon small startups have against predatory behaviors, for example against aggressive actors and monopolies when you are a small fish in the pond. Group life is an evolutionary response to threats: the wildebeest that inhabit the open plains of East Africa live in massive herds because there is safety in numbers. As Terminator would say (90s kid here): “come with me if you want to live”. In fact, there is actually no conflict between collaboration and self-motivation. Herds can be opportunistic, transient and fickle, where clustering can revert to solitary life when the threat is removed.
We humans can afford to be individualistic largely thanks to our rich evolutionary history of collaboration; the collaboration of our ancestors but also collaboration of cells and genes in the organisms that evolve into our ancestors’ ancestors and ultimately in ourselves. I can’t help but find it quite ironic that the sole reason we can have the cognitive ability to decide to act self-interested is the result of billions of years of cooperation.
Our tendency to create isolated products is beyond shortsighted. As long as privacy and ethical integrity is ensured, a collaborative, interoperable product has more chances to succeed versus one moated by air gaps, secrecy and proprietary formats and interfaces. Disaster kicks in when insular products are forced to interoperate by means of ad hoc artifacts such as shady middleware and odd translators, creating the grounds for a “Chinese Whispers” game and sprinkling the whole thing with multiple points of failure.
Ancient explorers used to believe there were giant dragons lurking in unexplored areas. We have a historical tendency to assign malign, intimidating entities to the uncharted interstices between known boundaries. As you know, there were no dragons, and the fact we managed to overcome that fear made the modern, connected world we know today possible: it clearly paid off. Equivalently, there are no dragons between the products we create, and having them ready to interoperate will always outweigh the benefits of keeping them in a glass box.
Form alliances and partnerships. Make your products speak languages that can be understood by other products. Choose avenues which maximize interoperability. The time to exploit vendor lock-in and building moats comes later in your journey.
# Shock Your Audience
_"Do you wanna see the most beautiful thing I’ve ever filmed?"_
A soft Erik Satie-esque piano plays in the background along with some melodramatic strings, while a video of a plastic bag blowing in the wind back and forth is shown, and a man with watery eyes comments on how he struggles to take the beauty that stems from the world, which is figuratively represented by the erratic plastic bag. The scene belongs to the movie “American Beauty”, and I remember struggling to connect beauty with flying trash, but the scene seemed to hit many around me in the cinema; everyone was weeping. Maybe it was the abuse of minor chord progressions, the price of the popcorn, or maybe the scene was indeed beautiful for them. I’ll never know. But it kept me thinking for a while (for 22 years, the movie is from 1999): what is beauty for us, non-philosophers mortals?
Beauty is that gentle shock we feel when we observe or interact with something that strangely aligns with our tastes, ideas and visions, perhaps unexpectedly. It can be its elegance, compactness, enormity, or lightness. It can be its simplicity, its complexity; its symmetry or asymmetry. It can be the message that it gives, the thoughts it provokes, or the way it performs. Beauty is a private experience, as thoughts are, because beauty is a thought[3](#ref_3). A pleasant one.
In a risky venture into the minefield of clichés, I think anything can be, in fact, beautiful. The natural and the artificial. Also the overly quotidian: a text, a letter, a process, an email, a meeting, a presentation, an algorithm, a leadership style. Why not? They can resonate.
And you shall strive for such resonance in whatever you create. But, there is a caveat. You will never be sure you will be able to hit others’ strings. Therefore, you are left alone with the chances.
A plausible route to beauty is to create products that are honest, lean, concise and non-pretentious. Something that does the job, but leaves a mark.
# Tango
Juan D’Arienzo was born on December 14th 1900, at the heart of Congreso neighborhood, in the bustling Buenos Aires of the beginning of the 20th century. A violinist and a talented composer, he would eventually become a renowned tango orchestra leader, earning his nickname “El Rey del Compás” (The King of Beat). I would get to know and appreciate D’Arienzo’s music through my dad, who would also get it from his dad: that’s how tango (still) typically passes through generations in a family from Buenos Aires, just like your football team: by inheritance. My grandfather Alberto was a tango lover, and a prolific vinyl collector. Back in the 1940s, he would hang around with tango ensembles, making good friends with musicians. On a surge of homesickness, I started to search for material from D’Arienzo (which is unfortunately scarce), and managed to find some gems, notably this one:

And this performance of one of the most recognizable tangos ever: “La Cumparsita”:

If you watch these two videos closely, something interesting stands out. When you think about an orchestra director, you probably think about the guy in a tuxedo, standing on a platform located at a distance from the performers, brandishing a little stick to the solemn delight of a somewhat patrician audience. But this is different, because this is tango, and tango is not about solemnity nor forms, but about intensity and closeness. Juan D’Arienzo stands right next to the musicians, holding no stick but vigorously waving his hands to encourage them, guide them through the dry staccatos, without stopping for a second having a big smile on his face (check the hysterical laugh at 0:30 in the first video); he is totally into it, as the band is. Bit unorthodox from a music theory perspective? Perhaps. Makes you want to go grab a bandoneón? Absolutely. Juan gathers all the looks without tarnishing the band’s prominence. There is such chemistry going on there, you can literally hear the cohesion in the music. In the second video, at some point he even grabs a violin and joins the ride.
If you are trying to visualize or get to the core of what leadership is, search no more. No course or book will describe it better than this cinematic example; leading means precisely what you see there.
It means to encourage and uplift those who are on the line because, without them, there is no music. It means being joyful and close but not too close to break their flow. It means helping them give the best they can, while knowing at all times that it is their diverse skill sets combined that creates the richer sound: one person alone is just a tone whereas only a team can create chords; every team has a unique timbre. Moreover, a proper leader is always ready to roll up sleeves and, if needed, grab an instrument and play along, absorbing the scrutiny, rejecting the credit.
# Do Not Lose a Minute
I said some sections ago that your job as CEO or CTO is to think. I stand on that. But you also need to act. And quick. Otherwise, you are just paralyzed, you become some sort of philosopher (not that there’s anything wrong with that). Philosophers and tech startups don’t fully mix. No startup in the history of startups has survived out of pure abstract thinking. It’s not the idea, it’s the execution. Execution can be challenging. From an idea to a working thing, there are myriads of quirks and details which must be sorted out, which takes time. Learning takes time. Hiring takes time. Signing a contract takes time. So, think about this when you calculate runways and time-to-live. You may be fooling yourself, time left may be shorter than you think.
In his classic _The mythical man month_, Fred Brook states: “How does a project get to be a year late? One day at a time.” On the same note, Hofstadter’s Law states: “It always takes longer than you expect, even when you take into account Hofstadter’s Law”. An entire book could be written about how massively error-prone we are when we estimate the time stuff will take. Time estimation is deeply affected by multiple psychological factors: we are usually overoptimistic (we think it will take less than it will take) and reductionistic (we overlook dependencies that our task will need to progress). Most of us view the world as more benign than it really is, our own attributes as more favorable than they truly are, and the goals we adopt as more achievable than they are likely to be. We underestimate uncertainty by shrinking the range of possible uncertain states, by reducing the space of the unknown. The unexpected always pushes in a single direction: higher costs and a longer time to completion, never the other way around.
A way to reduce uncertainty in time estimation can be done by relying on heuristics and data; if you have done something similar in the past, you can use that experience as a calibration factor for your estimation on how long something else will or could take. Mind looking back at your trail, remember?
Time is a central part of what we do. Designing technical products is organized around projects, whose lifecycle takes time to painstakingly go through stages, from infancy to retirement. Duration of those stages is never fixed, but they seem to continuously stretch due to delays.
It is because of the highly collaborative and interdependent nature of what we do that delays are frequent. But delays are not indivisible units. Delays are the aggregation of small, tiny ones that are usually taken as acceptable or inoffensive, when they are not. Just like a million microseconds are needed to elapse to get a second in your watch, a million project micro-ticks are needed to elapse for one project tick to elapse. When a project is delayed, it is hard not to imagine that a series of major calamities must have taken place. Usually, however, the disaster is due to ants, not tornadoes. The day-by-day slippage is harder to recognize, harder to prevent, harder to make up. Yesterday a key person was unavailable, and a meeting could not be held. Today there’s an Internet issue, because of network maintenance. Tomorrow the latest software patches will not be deployed, because deployments are not allowed on some specific day of the week. Each one only postpones some activity by a half-day or a day, and the schedule slips, one day at a time. One second at a time, one microsecond at a time. Losing focus makes you waste precious amounts of time. Some random RFI came through? Some conference in some distant place by the sea? Choose wisely what you spend your time on. Be lean. Learn to say no. Learn to only do things because they are time objectively well spent.
# Choose Wisely Your Partners in Crime
Another longer section, because it deserves it.
Jim Collins has written extensively about the rise and fall of companies. In his _“How the Mighty Fall: And Why Some Companies Never Give In”_, he and his research team explain in great detail that companies tend to decline following five stages:
1. Hubris Born of Success: This stage kicks in when people become arrogant, regarding success virtually as an entitlement, and they lose sight of the true underlying factors that created success in the first place, ignoring that chance plays a role in many successful outcomes, and failing to acknowledge the role luck may have played in their success and thereby overestimating their own merit and capabilities.
2. Undisciplined Pursuit of More: The nefarious “more is more” stage. More scale, more growth, more acclaim, more hype, more of whatever those in power see as "success". The organization grows beyond its ability to fill its key seats with the right people, and it balloons staffed with the wrong people.
3. Denial of Risk and Peril: Internal warning signs begin to mount, yet external results remain strong enough to "explain away" disturbing data or to suggest that the difficulties are "temporary" or "cyclic" or "not that bad," and "nothing is fundamentally wrong."
4. Grasping for Salvation: The cumulative risks-gone-bad of Stage 3 assert themselves, throwing the enterprise into a sharp decline visible to all. Here’s when "saviors" and charismatic visionary leaders may appear, with bold but untested strategies, or a radical transformation, a dramatic cultural revolution, a hoped-for blockbuster product, a "game changing" acquisition, or any number of other silver-bullet solutions.
5. Capitulation to Irrelevance: The longer a company remains in Stage 4, repeatedly grasping for silver bullets, the more likely it will spiral downward. In Stage 5, accumulated setbacks and expensive false starts erode financial strength and individual spirit to such an extent that leaders abandon all hope of building a great future. The organization atrophies into utter insignificance; and in the most extreme cases, the enterprise simply dies outright.
The book dissects different case studies of resonant companies which went from great to near collapse in an almost unstoppable death march. But it also shows how, in some cases, companies recovered just in time. Company decline is, luckily, not an irreversible process.
Collins’ book mostly talks about public-traded, multi-billion, high-profile industry behemoths and puts a particular emphasis on CEOs and their mistakes, which is a somewhat easy thing to do if you have the benefit of hindsight, which is usually 20/20. But it falls short on shedding light on the real problem: the corporate governance flaws which gave CEOs enough freedom to make the mistakes they made, by spasmodically ousting executives and replacing them with charismatic charlatans, or by approving mergers which ended up being deadly ballasts.
After reading How the Mighty Fall, you may get the impression CEOs are the ones to blame. And you would be right, but that is only one side of the story. How does corporate governance prevent a powerful CEO from taking a company all the way from stage 1 to stage 5? The mechanism of choice to prevent such a pilgrimage into the abyss is an entity which tends to cleverly dodge the spotlight: the Board of Directors. What are the Boards of Directors and how did they appear?
Once upon a time, companies were mostly owned by families and individuals. But then we, as the inventive and restless bunch we are, had the marvelous idea of inventing what now is known as the modern corporation, by means of subdividing company ownership into small chunks (shares) which could be sold and traded by basically anyone. The concept picked up and soon people were investing in corporations with very little liability. This came with an uncomfortable side: companies started to be owned by thousands of people. And this made corporate governance a pain in the neck. Mostly because those owning stock felt entitled to have a say in the company decisions, and wanted to be informed. Meetings with shareholders became chaotic: everyone had questions, debates would go forever, decision-making became impossible. So everyone started to hate these meetings. The solution at the time? Meet all at once, but less frequently, like once per year. This approach had a downside: it made shareholders gossip extensively during the time in between the meetings. Rumors would spread without control. It again called for a solution, and the solution was: the Board. And it was pretty good for the problem it came to solve. With shareholders being able to choose board members they trusted, these board members could act for the best interest of those owning stock. And management loved it, because in a way, the Board acted as an abstraction and insulation layer between them and the needy, noisy shareholders. But, when it came to strategic thinking, problem solving and, more fundamentally, keeping wacko executives at bay, Boards were not as great.
And then, if this was not enough fun, another invention came along to make things more interesting: the tech startup.
The tech startup is a product of modern venture capital. And venture capital appeared in the 40s, following WWII and the need to develop military technology. Most of what it’s known about Silicon Valley is typically from the 70s onward, but its story comes from way before that time. It is a little known fact that Silicon Valley (before it was called that way) has military roots, where brilliant people were creating groundbreaking technology for defense. Some clever folks saw the value in these brilliant minds and their ability to develop complex products, and they started to inject capital. The capitalists (later called venture capitalists) started to fund the brilliant minds. They didn’t just buy stocks. They invested in growing the organizations from the ground up. The venture capitalists provided lots of cash at a very early stage. In return, they got a large stake and significant influence. It was a small and closed party. The people involved in tech startups could talk around the kitchen table.
So, we can see the difference here between the tech startup and the corporations which gave origin to the concept of the Board. A typical startup does not have a large number of investors. Investors do not have limited access to information. Investors are very close to management. But, more importantly, tech startups deal with complex technical challenges which require special knowledge. Think about one of the most famous tech startup disasters of the last decades, Theranos, and how each board member was highly accomplished and connected, yet none of them had any substantial scientific or health care industry experience to understand that they were being deceived by an eccentric, close to psychopathic yet charismatic executive who was leading the whole company to a stage 5 cliff by over-promising a product that was as appealing as technically unfeasible. Nobody talks much about the Board’s role in the Theranos disaster; but books and documentaries about CEO’s role have been released.
In short, the problem that the Board concept initially came to solve, does not apply for tech startups. The Board, understood in the classic way, is the wrong tool. The Law of the Instrument, also known as Maslow's hammer, is a cognitive bias that involves an over-reliance on a familiar tool. It basically says: when all you have is a hammer, everything looks like a nail. When the only governance system you know is the Board, every organization looks like the Dutch East India Company. You gotta love the irony here: startups brag so much about their innovative approaches, yet they go and choose such archaic methods for their own internal direction and control. The shoemaker’s children usually go barefoot.
Used in the old way, the Board is pointless: a group of loosely coupled individuals spread around the world who act more like diplomats, undersampling the many companies they look after by visiting every now and then. Usually rich guys with a distant hit (an exit, etc) they repeatedly brag about. Predominantly male and technically shallow, they walk around the office space, coffee in hand, asking irrelevant questions, wasting the time of those who are doing actual work, diving (at the most) PowerPoint-deep in what’s going on. You know, living the life, having nice dinners, bringing their relatives along, only to eventually fly away to never be seen again until half a year later when the cycle repeats.
Just as Collins’ finishes his book with “well-founded hope” on how companies can recover from almost rotting to death, I will try to finish this section with “well-founded hope” about the Board concept.
The Board system can work, but it must be refurbished. Avoid the office wandering snobs, and assemble a technocratic board with architects. A clique with expertise in areas that startups desperately need: product discovery, complex systems, competitive intelligence, finance, software architecture, strategy, conflict, and a solid grasp on the technology the company is dealing with. A tight and vitally diverse oracle of near-scientist system thinkers, extra-hard to bullshit, and addicted to creating lean, lightweight, healthy organizations. People who cultivate low profiles and simple lifestyles, who despise buzzwords, fads, and vapid metrics. Polymaths who can master more than one skill (to keep it small), who have a constant thirst to guide companies go from nothing to good, from good to great, and built to last. Hard to find? Yes, as gold is, which means that a large amount of rock and mud will have to be processed to find it.
# Wins, Flops and Statistics
Superb performances and flops have a lot in common. Both are deviations from an _a priori_ expected outcome. The former is great, the latter is a bummer. One skyrockets our confidence and ego, the other one makes us question why we are even trying. But, in time, outstanding performances tend to degrade, whereas duds tend to improve. Nothing is really consistently too good, nor too bad; things migrate to the average. What goes up must come down and what goes down must come up. Periods of above averages are followed by below averages. Everything regresses to the mean.
_“Regression to the mean is not a natural law. Merely a statistical tendency. And it may take a long time before it happens.”_ — Peter Bevelin
Think about darts with your friends. You throw once, you hit the wall. Your friend throws one, hits the very center. You sigh, she rejoices. You both try again. What are the chances the very same outcome will happen? Unlikely. Most likely you'll do better and your friend will do worse. Both of you are regressing to the mean, which indicates a good deal of luck is at play. If you played just once, you would have left thinking you suck, whereas the reality is that you may be as ok as any of your friends (assuming none of your friends is a professional dart player). The less times you play, the more the outcome is ruled by chance and not by skill. Doing engineering is quite like throwing darts. We define a set of targets (technical performance measures, time to market, some company goal, etc), and we aim our darts (our systems and processes) to hit the bullseye in the center. Thing is, we do not control all the variables needed to hit the center of the target; a good deal of chance is at play. What are the things we cannot control? Multiple, and at multiple levels. Components can fail prematurely, a key team member suddenly leaving, an investor pulling out, a big new player entering the market, a supplier going belly up, etc. Shit happens.
But many other things we do control. A thorough architecture design, a robust fault-handling approach, ample testing, healthy team environments, a constant gauge of the markets and competition. We have means at hand to reduce the impact of chance, but we can't nullify it. One way we can gain confidence (i.e. throwing more _darts_) is for example by prototyping and iterating. Prototypes help us gain great insight about performance and about component interaction that we cannot see with the parts in isolation. Prototypes can either fail or work. Considering regression to the mean, the fact our prototype has worked does not mean we can relax and go enjoy the fame (as in, send it to production). We might have been very lucky, it could've been a near-miss. Confusing near-misses as wins can be harmful, since we fool ourselves to believe our stuff is great and ready to be fielded when it could've been at the very edge of misery. The design could've been only marginally working thanks to a benign combination of factors. Next time things could be different.
In product design, making things work is not the real challenge; making things work in a consistent manner is the real deal, as external conditions vary, come what may. It may take many tries to achieve such consistency, to minimize the role of chance.
Markets are not different. Talking about playing darts.
Your startup, my startup, a restaurant, a shoe shiner. We all have something to offer. When we reach out to markets to offer whatever it is we offer, we face the big question: will anyone want to buy it? Or will a tumbleweed roll in front of our eyes?
We just don't know. We cannot know.
In all these cases, there are two sides: the offerer, and the offeree. If the offeree finds the offer plausible in some way, they engage: offerer and offeree relate in a transaction where what’s offered is, in some way, approved and offerees give something to the offerer in return. Depending on the case, we may seek to funnel multiple offerees into one single final engagement. For example, in dating, or jobs applications, we act towards selecting one and only one to engage with. Or, we may need to funnel many offerees into a few engagements (for example, investors in a round). Or, we may seek to broadcast our offers to the biggest audiences possible and try to engage with as many as reasonably possible (this applies for books, a tweet, or any consumer article). Whatever the thing offered may be, it is not what *finally* satisfies the offerees: someone buying a book does not want a book but wants insight, or a great story. As the famous example goes, “no one wants a drill, what they want is the hole”.
What makes an offeree engage? What is it to actually engage?
In a March 1966 interview, John Lennon argued that the public were more infatuated with the band than with Jesus, and that Christian faith was declining to the extent that it might be outlasted by rock music. His opinions drew no controversy when originally published in the London newspapers, but drew angry reactions from Christian communities when republished in the United States that July. Lennon's remarks were deemed blasphemous by some religious groups. Some radio stations started to refuse to play the Beatles' music. One radio station hired a tree-grinding machine and invited listeners to deliver their Beatles merchandise for destruction. Some others organized demonstrations with bonfires, drawing crowds of teenagers to publicly burn their Beatles records. Photos of teenagers eagerly participating in the bonfires were widely distributed, and the controversy received blanket media coverage through television reports. Brian Epstein, the well known manager of the group, was largely unperturbed. He famously said: "to burn Beatles records, they've got to buy them first”. Is this what engagement means?
In the movie _Small Time Crooks_, career criminal Ray (Woody Allen) and his cronies lease a closed pizzeria so they can dig a tunnel from the basement of the restaurant to a nearby bank, to rob it. Ray's wife Frenchy (Tracey Ullman) covers what they are doing by selling cookies in the restaurant. The robbery scheme soon proves to be a miserable failure, but selling cookies becomes a massive success and it makes them millionaires.
If you take these two examples, they speak of controversy and luck (granted, the last one is purely fictional). From this, you may think customer engagement and product/market fit come by being utterly provocative, or by just by chance while searching for something else. What these stories show, at the end of the day, is that engagement does not necessarily follow deterministic trajectories. We may want to confine our target audiences to rational, quantifiable facts. However, the offerees we aim to are often intuitive and emotional.
John Maynard Keynes coined the term “Animal Spirits” to represent such behavior. He described animal spirits as “a spontaneous urge to action rather than inaction, and not as the outcome of a weighted average of quantitative benefits multiplied by quantitative probabilities". Far from calculation, a high degree of emotionality may be involved when customers decide on what to engage in, or what to let pass. This means, engagement may not happen when it should (rationally) happen, or may happen when it was totally not supposed to happen. This is, among other reasons (such as price, performance, quality), why a priori great offers and products can fail miserably[10](#ref_10). Or why mediocre value propositions may pluck the right string and kick off.
That being said, and as wild as animal spirits may go, you should not conclude from this that everything depends on waves of irrational psychology or pure chance. I am merely reminding ourselves that human decisions affecting choice and the future, whether personal or political or economic, does not depend on strict mathematical expectation, since the basis for making such calculations does not exist; and that it is our innate urge to act which makes the wheels go round, our rational selves choosing between the alternatives as best we are able, calculating where we can, but often falling back for our motive on whim or sentiment or chance.
All this being said, our ideas, products and content must stand out in a sea of alternatives which are elbowing everyone else in order to be chosen. While acknowledging that choice may not always follow a deterministic path, still our offers must strive to be simple, clear, original, intuitive, understandable, accessible, honest, ethical and thoughtful.
The rest is up to the spirits.
# Take Proper Notes
Startups are, without a doubt, an overly complicated way of making money. Machinery, computers, people, processes, buildings, and a long et cetera. Why do they even exist? A marketing manager would say: to create great products people will love. Whatever. A bureaucrat who read a book or two would argue: for efficiency, to reduce cost of transactions. Yawn.
Sure, there are romantic or scientific takes on it. Fundamentally, startups and companies exist because there is no better way to reach market fitness than getting together to collectively learn how to do something. The experience curve nicely represents this relationship: The longer an activity is performed, the more experience about it accumulates, and the more performance improves, which compounds in time to be a competitive advantage when others are trying a similar thing. Known as “Wright’s Law”, it states that “we learn by doing” and that the cost of the things we produce decreases as a function of the cumulative number of things produced. It reads quite obviously, but tends to go underestimated.
Story time.
Years ago, when I was a young engineer full of dreams (and hair), I was working in a company which made, and still makes, LED digital billboards. We were struggling with expensive and long lead-time PCB (Printed Circuit Board) prototypes, so we wanted to try an in-house rapid PCB prototyping system. For this, we chose the known approach of using cheap copper sheets added with photosensitive dry film and exposing them to UV light to create the pattern of the PCB tracks to be etched by a ferric chloride solution. Actually, you want the PCB tracks to stay and all the rest to go away, so you expose the photosensitive film to the negative of the PCB design, usually printed on a transparency. So we went ahead and made this poor man’s PCB prototyping station, with a cutting area to tailor the big copper sheets to size, a UV exposing device (which looked like a crappy copying machine where you would put the copper plate to face the lights and close a lid), a bucket to soak the exposed PCB with the etchant, a cleaning and drying station and finally a drilling station. There were a lot of quirks around the process: cutting precision, time of exposure, time of etching, aligning top and bottom layers, the quality of the print of the negative PCB pattern in the transparent film, drilling precision, and a long, painful et cetera. When we started, it was awful; everything that could possibly go wrong went wrong. We couldn’t get anything decent, and we were using tons of materials; we were clearly winging it. At some point, the company owner came to check (we’d been enthusiastically pitching the idea to him for weeks); although he was not impressed, he said: “I hope you are taking proper notes”. It felt so stupidly obvious, yet such sound advice. We were not really collectively compiling our experiences but only keeping isolated notes here and there. So we decided to put good effort into capturing all outcomes in a unified place, compiling numbers, experiments, results. After a few days of more trial and error, we were capable of producing PCB prototypes with 208-pins fine-pitch QFP packages on both sides, with almost no scrap materials. Theodore Paul Wright was nodding in approval from a cloud. In time, we improved not only materials use and time but also the experience for whoever was operating the prototyping station: better lighting, better time keeping, better protection from chemicals, better cleaning. We eventually wrote a software tool (in VB6!) for guiding the occasional operator. Of course.
To be clear, I am not saying that the quality of our notes defined the outcome, but the fact we were getting better at it by doing AND the fact we organized our learnings in a more collaborative way did definitely change the game. It reduced the amount of time wasted trying things others had tried to no avail, and gave the possibility to better cross-check ideas and findings along the way. Try journaling for a month; as in, write all the relevant happenings in your organization and the projects around you. If it's a startup, you’ll have a good laugh when you read that journal a few months down the road: so many things change, so many ideas appear and disappear. What was the thing a few weeks back, it’s unholy now.
Companies are (or, should be at least) like fishing nets, capturing everything as they go, the wanted and the unwanted, the signal and the noise, and managing to “take proper notes” and sort out what is useful to keep versus what can be returned to the sea. Goes without saying, plenty of mistakes are made in the process, because mistakes must be made for they are the lighthouses which signal that it’s time to perhaps swerve away from current direction, possibly a collision course. The beauty of this is that competitors are also learning and getting better as you sleep: they will eventually figure things out just as you did. Time matters; you can’t take forever to learn. Even more beautiful is the fact that your competitors’ improvement will sooner than later affect you and force you to learn new things. As companies learn, peripheral things outside their core products or offerings improve as well: user experience, customer support, packaging, supply chain management, reliability.
Most of this sounds very obvious and could have been said by any random consultant out there. But here I am for something else: companies make great efforts to avoid showing to the outside their learning pains and that they have made (or are still making) mistakes. They put effort in making themselves look infallible and know-all, dressing everything as a win, whereas we all know the nuanced, objective reality is that some things must be indeed working awesome whereas other things must be at the “well, damn” stage. Granted, companies are opaque: we can’t see from outside what’s really happening. Sure, wanna make yourself look like you are the corporate equivalent of Mr Olympia? Go for it, as long as this silly posing is strictly done to external observers and not within office walls. Internally, learn by doing, learn fast, and take proper notes.
# Mind the Long Tails
There is a tendency to confuse the mathematical representation of a phenomenon as the ultimate explanation of such a phenomenon. This is: to believe that the way a process evolves lies in a set of equations describing the process, and not the physical or phenomenological properties at play. Like if waves, for instance, were actually produced by differential equations, instead of disturbances traveling through a medium. Obviously, waves existed before there was a single human brain roaming the Earth, even before there was a single living cell on this planet, let alone there were differential equations. Just like thinking that objects would not have ever moved had the apple not landed on Isaac Newton’s bean. A problem of our times: to believe that constructed models explain reality better than reality itself. Or, more specifically, to only observe the model and ignore the nuanced reality that the model represents. The map is right, hence it is the territory which must be wrong.
This happens for instance with the power law. Some take for granted that certain processes are somehow fatally bound to always follow a certain curve, as if math were an unkind dictator which controls all the outcomes while we are powerless spectators of equations converging who cannot do anything to change the upshot. Power law, in many cases, tends to be gamed as an elegant pseudo-scientific euphemism to legitimize elitism and discrimination where the powerful few rule the submissive lot. Many who talk a lot about it go as far as to imply that the power law seems to be almost an inescapable natural law. They use examples from earthquakes: biggest earthquakes cause more damage than 80% of all small earthquakes combined. Or they cite studies which observe that in a milk production farm, 20% of the cows will outperform the milk production of the remaining 80%. Or how the biggest cities hold a concentration of people bigger than all smaller towns combined. In short, they bend cherry-picked analogies to justify their snobby thinking.
Unsurprisingly, those who glorify the power law belong to the elites who benefit from propelling everyone to accept such “natural law”. As if we should just acquiesce to the inequalities given by higher principles which dictate that a small number of clustered actors will always take the calls while many, many others will only get the crumbs.
Thinking this way, my t-shirt daily pattern of use follows a power law: of all the t-shirts I own, I tend to use only 10%, 90% of the time. Why so? Because of my own stupidity, or laziness. They tend to form a pile in the drawer, and my lazy ass tends to more probably pick the ones on top, so I end up only scratching the surface of the stack and using those easier to reach. It’s not that I like them more, nor that they are better in any way. They just happen to be on top. I could just shrug and say: “it’s not me, it’s the power law! My hands are tied, it’s the evil math!” Bullshit. It’s me and my behavior. It is me and my own choices which lead to such a pattern. In probability terms, my frequently chosen t-shirts are part of the head of the distribution, whereas the forgotten ones are in the long tail. As you can see, math only depicts our behaviors and choices, and our behaviors are not defined by equations.
The investment world tends to work in this way. Or, to be fair, any discipline where choice among a various set of alternatives is involved. It is just like a t-shirt drawer. It will always be easier to choose whatever is sitting on top of the pile. Not because of pure laziness, but because we tend to grab what comes easier, what we know better. The fact your startup does not get funding, does not get to hire, or does not even get emails back does not necessarily mean you are shit. You might be at the bottom of the drawer, so you better do something to get up from there.
# The Rich Get Richer
I was a pretty good student in primary school, who used to have good grades. Then, grades consistently declined further ahead during High School and Uni (by then I had realized music, friendship and football were more important, and I regret nothing). While in Primary School, when I was maybe 11, I started to realize that the teachers had somehow flagged me as the "A-grade guy" and they had begun to evaluate me in what I felt was a bit of a laxer way. I had found mistakes in some exams of mine still graded "A"; A-grades were somehow coming in too easy. So I decided to test it. There was this one exam I purposely decided to add wrong answers here and there. Not everywhere though. I still got an A (or a 10, in the Argentinian scoring system). This gave me two insights:
1. It seemed I was not being critically evaluated anymore for what I really *knew* or studied. It looked like the fact I had passed exams before (my "track record" of sorts) was, somehow, influential. It seemed teachers were in some kind of "autopilot mode" with me, affecting their critical thinking. As much as I enjoyed getting As, there was something wrong about not feeling critically evaluated anymore. I was "open loop".
2. I quickly understood that just as I was flagged as the "A-boy", someone was flagged as the opposite. I quickly identified this person in my class. He was repeatedly failing at exams, despite (which I know first hand since he was a friend of mine) him trying hard to overcome this, to little or no avail. It seemed teachers were in "autopilot mode" with him as well.
What I was testing, without really knowing, was the Matthew Effect: the rich get richer, and the poor get poorer. It is a reinforcing loop: success boosts status, which attracts more success. Failure does the same, just in the opposite way. A key factor here is to define what success really means.
If we take a high grade (an A) as a cold measure of success, I was being successful. Now, if we consider true success is about proving proficiency in a topic while being thoroughly reviewed, I was failing miserably. Moreover, my friend was perhaps more successful than me, since he was building at least a good deal of adaptive skills and resilience to overcome difficulties and dealing with failure, which are good traits to have for life in general. "Successful" people tend to handle failure less elegantly, for they usually do not know how to react to it. Still, I can imagine my friend having a hard time telling his parents: "I am not failing my exams, I am just building resiliency for life".
The Matthew effect is all around. How many times have you read a shitty article from a multiple-times best-seller published in a renowned publication? You get the feeling they would get published even if they randomly hit the keyboard with a stick, and the likes would still count in the thousands (I'm feeling compelled not to share many examples here). How many other times some guru in your organization comes up with a ridiculous idea everybody applauds while you scratch your head thinking how that would've gone, had you proposed the same? The bar to gauge current output seems to be greatly affected by the past. If there is no perceived past (i.e. you are a nobody for some audience) the bar will be extremely stricter, to the point the work may be disregarded or simply ignored. As much as a reputation may indicate competence or prolificness, it does not guarantee current nor future effectiveness by itself. Thinking so can be even damaging (hail to those who don't buy the flashy credentials and put the stuff under the skeptical magnifier, no matter what). Along the same lines, being fresh in a domain must not equal automatic indifference; there are hidden gems all around out of the mainstream.
How many times have you seen a shitty startup with a shitty product getting tons of money in their Series B or C? Don’t entirely stress about that. First, because you have to mind your own business, and second, because those are most likely riding the wave from past hits, which does not mean they are currently keeping their promises.
# Shit Happens
Startups live and die. They come to life as easily as they step into the abyss and find eternal solace in the arms of nothingness. Sparklehorse wrote: Everything that’s made is made to decay. There is even some beauty in collapse, for it shows the intimate connection between creation and destruction, order and disorder, equilibrium and disequilibrium. Yearly, thousands of tourists gather in glaciers to witness massive amounts of ice hopelessly collapse into the sea. There is something fascinating about seeing orderly things going shapeless.
All that is believed to be eternal falls. Hegemonies fall. Empires fall: they rise to power, rule, decay, and implode into nothingness. Collapse is part of the life cycle of everything. Some social scientists claim that collapse is the single most important event of a civilization. As fascinating as it can be, it is a stage we don’t want to be part of, or get close to; we only want to observe it from a safe distance. Collapse is a point in a startup’s history where lessons are of highest value; mostly for the survival of whatever is coming next. Whoever survives a startup collapse increases the chances of survivability of the next one (if there will be a next one, and if lessons are learned).
As we do not seem to appreciate talking about our own demise, many prefer to avoid discussing collapse as a possibility and prefer to believe that the organization will magically live forever. But they do not live forever: organizations die. For reasons: bad products, bad teams, bad choices, bad advice, bad leadership, bad timing. Bad at discerning what’s bad.
Minding why and how organizations disintegrate is of vital importance to every member of a startup, for they are direct contributors to both its rise and fall. It’s a constant fight against entropy: complexity increases steadily, until it reaches levels that are unmanageable and damaging. But complexity creep is not the only factor. There are, also, catastrophic external events which can create the right conditions for a downfall (massive sudden economic downturns such as COVID-19, financial market cracks, funding pull-outs, end of runway, etc). In these cases, the capability to adapt to changes, both internal and external, will define survival. Adaptive organizations prevail. Weak, rigid, stubborn, deaf ones will go. Detachment from reality, ego fights, founder syndrome, management group-thinking and overconfidence contribute to the magic formula of disaster.
Big companies' collapses are loud, and leave behind great deals of information that scholars then, not without hindsight, analyze ad nauseam to explain what most (including them) could not see coming. But most startups die in silence. They collapse in a way they radiate little information about the whys, the hows, the whats. At the most, you get to read a tweet in sorrow from a distressed employee who got laid off, or an anodyne press release blaming the world for not understanding the idea.
Collapse is never atomic. Before the startup's last breath, there is a chain of smaller internal collapses linked together which snowball and create a chain reaction to the big crack. Work relationships collapse, teams collapse, departments collapse, product lines collapse. Just as a building collapses when the load bearing structural elements collapse, organizations do not collapse from the top down. The top does not bear any load. The load bearing elements in the organization are the lower elements in the hierarchy. The worker ants.