A few days ago, on the back of a long conversation with Haresh Chawla that hammered home how rich I really am in a country called “India A" with a population of 180 million, I felt compelled to articulate the difficulty of being trustworthy. A partner at the private equity firm True North, Chawla ended our conversation by asking me to think over two questions:

Question #1: Imagine a world where everybody has at least $100 million to spend. What may that world look like?

Question #2: Given a choice between earning $100 million and being awarded the Pulitzer Prize, what would I want more?

The first question was something I hadn’t thought of. Some thinking and looking over literature later, I stumbled across a very interesting pointer from history on the community platform that is Quora. Turns out, if the same question were to be asked in the year 1287, it would read like this: “Imagine a world where everybody has at least $1 to spend. What would happen if everyone in the world was a dollar-aires?"

The crux of the question is that way back then, $1 was a fortune to amass. But by 1603, there were a lot many dollar-aires spread across the world and people wanted to be hundred-aires. As things stand in 2017, those numbers—once the utopias of extreme wealth—have eroded significantly and given way to millions and billions.

When looked at from that lens, the significance of Chawla’s second question started to fall into perspective. I knew what my instinct would say—that I want the Pulitzer Prize more than $100 million. But that raises a question: why?

Because when thought about, it isn’t easy to earn $100 million. To earn money is one thing. But to earn an exponentially large amount of it that exceeds the averages of everybody else around, you ought to be incredibly smart and an incredibly hard worker. And because its value erodes over time, you must keep getting smarter and working harder.

In much the same way, not everyone can win the Pulitzer either. While there are many around, those who earn it are not there because they are incredibly gifted at the craft, but because they work harder and smarter than everyone else who populates the domain they live in and operate out of.

But as a human, I have a choice. I can either focus on earning wealth or the Pulitzer. I cannot do both at once. Some like me may want the Pulitzer while others may want the $100 million. That is a function of choice. There are no moral absolutes on whether one choice is better than the other. On the contrary, there is a strand that binds both choices—both insist on some commitments.

What may those commitments be?

Again, some thought later, my mind wandered to a talk by an arrogant man who goes by the name of Nicholas Nassim Taleb. I must admit: it is easy to get tired of someone as overbearing as him. But that said, there is no taking away from that it is difficult to argue against what he stands for and believes in. May he have any pointers to what strands bind people of these kinds? Turns out there is.

He first articulated that you need some commitment and become anti-fragile—a theme to which he devoted a book. But to become anti-fragile, he says you first need skin in the game. That, incidentally, is the title of his next book and glimpses of what it may contain have been articulated by him in Antifragile, and in more recent times, in essays that exist in the public domain.

Like many people, I have read the book and his more recent essays with much interest and think the ideas in it compelling. But the real import of what he means by having skin in the game, getting to be anti-fragile, and how does it bind somebody who chooses to acquire wealth and somebody in pursuit of the Pulitzer, fell into place for me personally only the other day.

It was in an altogether different context and on the back of a conversation with an entrepreneur on what it takes to acquire customers in an Indian context. At the end of our conversation, I concluded the gentleman facing me was a fragile creature—he would never earn big money or earn a Pulitzer. He was destined for mediocrity. He was fragile and has no skin in the game. He was everything I don’t want to be.

But when we started out, I didn’t think that way about him. Instead, I thought I was facing a man who knows his bearings and imagined along what lines his answer may go. I imagined he may say it is far easier to acquire consumers for any entity than it was in the past and that he is thinking up ways to disrupt the future.

Embedded in my question was an assumption: the world we live in is changing at a pace unprecedented in human history. I could think of an example to bolster the assumption in my head. But I did not articulate that to him in as many words.

As recently as in 2004, to sequence the first human genome cost a few hundred million dollars. A decade later, by 2014, an entity called Illumina could sequence 18,000 genomes per year at $1,000 each and with far greater accuracy. But when the project started out, nobody thought high levels of precision at these kinds of prices may ever be possible.

Not just that. This was violating Moore’s Law—a hypothesis Gordon Moore, the founder of Intel, had originally stated—that the processing power of a micro-processor would double every 18 months. While Moore had revised his theory multiple times, he had gone on to predict it was close to saturation. But instead of saturating, technology had acquired a life of its own and growing at an exponentially faster pace than what he had imagined possible.

Back to my conversation with the entrepreneur. That is why his answer caught me off guard. “It may take at least a decade to acquire customers and retain them in the longer run," he suggested. “Particularly in the Indian context," he added for good measure.

And why may that be, I asked. Because customers, he said, are people. And people are fickle creatures. They need incentives, or nudges, if you will. The study of these “nudges" was the subject of Richard Thaler’s work on economics that got him the Nobel in economics this year.

But when we were having the conversation, the awards hadn’t been announced yet and I asked him to elaborate on what he means. His take was simple—and cold blooded as well: on the back of his experience in working on building the internet ecosystem, Indians respond to only one kind of incentive—a monetary one.

That is why, he said, everybody who operates in the space offers “cashbacks" to customers if they use the “wallets" their companies create. Very simply put, if my company wants to get you to start using my services, I create a digital wallet, which you load with money. To do that, I offer you an incentive. Most of them have figured by now that the only incentive that works are “cashbacks". No other freebie cuts ice.

What it means is, if you and I buy something worth Rs100 from a company using their digital wallet, the company may offer to put “cash back" (a discount, in other words). But unlike discounts in the offline world where the price is lower than then maximum retail price, whatever the discount may be is put back into your wallet. So it is entirely possible if you choose to buy something worth Rs100 and pay using a digital wallet created by the company, it may put back, say, Rs15 (or whatever else it thinks it can afford) back into you wallet. You can use that money to acquire other items from the company.

The stated intent is to get consumers comfortable with the idea of using digital wallets even as companies go about collecting data on people. But the problem with Indian customers is that they are bargain hunters. They look for entities that offer the most by way of “cashbacks". I don’t intend to get into more detail on the economics of it all.

Suffice to say that it was inevitable I ask: how long do you think before customers get used to you without your having to dole incentives like these? Like I said earlier, when without as much as blinking an eyelid he suggested at least a decade, it caught me off guard.

Because back of the envelope calculations suggest it is not feasible for any entity to offer “cashbacks" for as long as a decade. And I felt compelled to tell him that this sounds like a mugs game. It didn’t seem to bother him.

“It isn’t my money at stake here," he said. “As long as there are private equity funds and venture capitalists who want to buy into the great Indian middle class story, they’ll keep funding these discounts. If I think I cannot sustain it, I’ll sell the entity to somebody who has the muscle to run it for longer, I take what I get and get out. It’s as simple as that."

Is he right? Is he wrong? Is he a mercenary? How may I judge him?

Because even as he was saying it, it was evident that he wasn’t in here for the long haul. That is where Taleb’s Antifragile starts to offer some pointers and the entrepreneur now started to look like a wimp. Somebody with no skin-in-the-game. It is another matter altogether that I totally disagree with his assumption on how long will it take for Indians to change their behaviour. But if I go along those lines, I may digress a while.

So, while on the gentleman I was talking to, it was inevitable I look at him from the eyes of Taleb, who argues that one of the main primary traits of somebody who has a stake in the financial market is that they are ethical only when they incur a monetary risk as well in achieving a goal. In other words, they incur a risk.

That risk means, “Every captain goes down with every ship." In this case, the captain didn’t have any skin in the game. That it is somebody else’s money he was burning didn’t seem to bother this entrepreneur.

This is the what Taleb descrbes as a “situation in which the manager of a business is not the true owner. So, he follows a strategy that cosmetically seems to be sound, but in a hidden way benefits him and makes him anti-fragile at the expense (fragility) of the true owners or society. When he is right, he collects large benefits; when he is wrong, others pay the price. Typically, this problem leads to fragility, as it is easy to hide risks. It also affects politicians and academics. A major source of fragility."

But as I have always maintained and often quote, “The moral arc of the universe is long, and it inevitably bends towards justice." In that order of things, it is also inevitable that the true owners of the business, the ones who have put their skin in the game, will eventually reap the benefits. In my head, I’m willing to punt this clown is destined for mediocrity.

I can extrapolate this conversation into my domain as well. How many writers have the mental muscle in them to go after a theme and hammer away at it to the exclusion of everything else? What kind of skin in the game do they have to place when they go after what they believe in?

I tried to offer some pointers in this series early last year when a team of reporters went after the Catholic Church to expose one of its most darkly held secrets. It took a lot out of them. But, in the face of much bluster, the dignified silence exuded by their now-legendary editor Martin Baron kept the team going. He, to my mind, is anti-fragile. In thinking of what he may be like the other day, a line I read someplace came to mind: confidence is silent. Insecurity is loud.

It says much as well about the raucous times we live in now and the bluster television anchors greet viewers with every evening on prime time, driven as they are by trends on social media. Be that as it may, what may it take to be anti-fragile? On poring over the literature by Taleb, no straight answer is offered on what is to be done. But he does offer pointers on what is worth avoiding:

• Muscles without strength

• Friendship without trust

• Opinion without risk

• Change without aesthetics

• Age without values

• Food without nourishment

• Power without fairness

• Facts without rigour

• Degrees without erudition

• Militarism without fortitude

• Progress without civilization

• Complication without depth

• Fluency without content

• And, most of all, religion without tolerance.

If I were to step back for a moment and look at myself in the mirror and the society I am a part of, these strict notions have no place. Perhaps we can seek consolation in that we live in a society dominated by humans who, by their very nature, are fragile and afraid to put their skin in the game. It is inevitable then that they be condemned to mediocrity.

Charles Assisi is co-founder at Founding Fuel Publishing. His Twitter handle is @c_assisi

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