2017: A Learner’s Journey

New Books

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  1. Titan – Ron Chernow – Superb insight into the life and thinking of the original “richest man of the world” and one of the “robber barons”. Close view of the American life in the second half of 19th century and early 20th century. Easy read but offers a lot to ponder regarding pursuit of wealth, regarding questions on legal/regulatory compliance, and regarding the link between wealth, religiosity and philanthropy.
  2. Anatomy of the bear- Russel Napier – Detailed analysis of the macro economic environment around the four key bear markets of 20th century and the rebounds that followed. Serious stuff with rigorous macroeconomic analysis. Good historical reminder of life and markets during long term troughs – and peaks. Good reference material.
  3. Rain in the Mountains – Ruskin Bond – Classic Ruskin Bond that stirs up smell of the Himalayas and makes time stop for a while. Easy read.
  4. Behave – Robert Sapolsky – Excellent treatise on human behaviour drawing on neuroscience and psychology. Serious stuff with dense subject matter. Difficult and slow read in the early parts where the author has delineated the fundamentals of neuroscience. An eye opener and great value add for people who want to dig deeper into the science of human behaviour.
  5. Predictably Irrational – Dan Ariely – Lessons on our interactions with our environment, on ways to enhance our thinking process and thus improve our decision-making process in daily life and in investing. For those with interest in behavioural finance this book can be a logical extension to books by Kahneman, Thaler, Shiller, Howard Marks, James Montier etc. Easy/moderate read but must spend time to think through the questions raised.
  6. The Dhandho Investor – Mohnish Pabrai – Common sense based investment framework from the perspective of business owners. Quite simple though not easy to implement. But then investing is not supposed to be easy even if it can be made  simple. Easy/moderate read but worth spending time to absorb the ideas.
  7. Essays in Persuasion – John Maynard Keynes – Lessons in macro economy based on real life global environment in the first half of 20th century by one of the most recognized names in economics. Some elegant perspectives on macroeconomic events in an eventful period. Serious stuff but worth every minute spent. Best read in phases, instead of going for it cover-to-cover.
  8. The Introvert entrepreneur – Beth Buelow – Ten steps introverts can take to utilize their natural gifts and overcome their challenges to start a business. Can be taken as an extension of Susan Cain’s “Quiet: The power of introverts in a world that can’t stop talking”. Easy read.
  9. Talk like Ted – Carmine Gallo – Good highlighting – based on views of top psychologists, communicators and neuroscientists – of keys to deliver TED -like presentations that are engaging, persuasive and memorable. Easy read.
  10. Bull! A History of the boom and bust, 1982-2004Maggie Mahar – A fascinating history of one of the most potent bull markets in history. Highly informative and a must read for investors who seek lessons (“To Do’s “and “Not to Do’s “) from history. Easy read with a gripping narrative.
  11. A history of world in 100 objects – Neil MacGregor – Reading this is like visiting a rich museum with the curator – that too a deeply knowledgeable one. Nice way to tell history by linking it directly to archaeology and geography with focus more on trying to recreate the environment around processes and events, and less on events themselves. Easy read.
  12. Creating shareholder value – Alfred Rappaport – A different – dovetailing discounted cash flow method of valuation, with evaluation of management and company strategies- and rigorous framework for fundamental style of investment. Serious stuff requiring intense focus and comfort with numbers. Prior understanding of some basic concepts of finance will help. Good reference material.

Re-read Books


  1. Man’s search for meaning – Viktor Frankl – Reading this book can be a life changing event. Frankl, a famous psychiatrist who had to suffer the horrors of a Nazi concentration camp, emphasizes in this book the importance of finding meaning in all forms of existence even the most brutal and miserable ones. After his rescue from the camp he founded logo-therapy which went on to become an important method of psychotherapy. The milieu of the book – Nazi concentration camps – is understandably dark. Still, instead of being depressing the book is like a sublime lesson in optimism as the author continues to look for the meaning in his life. Easy/moderate read.
  2. Catch 22 – Joesph Heller – Not for nothing is this considered by many as one of the best works of fiction in the 20th century. Dark humor and satire of a different kind at its best in the backdrop of world war II. Easy/moderate read but only after one moves up the curve in the first 30-40 pages to synch up properly with the author and the characters.
  3. One up on wall street – Peter Lynch – Should be in the list of ten all-time best books on fundamental, bottom – up investing. There are important takeaways every time one reads this book.  Seemingly easy read but key is not to rush through or else not difficult to miss key ideas.
  4. Aunts aren’t gentlemen – PG Wodehouse – Perhaps written for people who love day dreaming. Typical Wodehouse that takes the reader to a carefree and happy world where one finds it difficult to hate even the villains. The joke is always on the English aristocracy but is never vicious. Like other Wodehouse novels here too there is a tinge of sadness on noticing that one is on the last page and as one gets transported back into the real world. Effortless read.
  5. Memories of Malgudi – RK Narayan – Real life nostalgia associated with RK Narayan. There are five novels in this collection – Dark Room, English teacher (semi autobiographic in nature), world of Nagraj (his last novel), waiting for the Mahatma, , and The guide. – Effortless read
  6. Raag Darbari – Shrilal Shukla – Timeless Hindi classic that refuses to fade into irrelevance even 50 years after it was first published. Every quirk, every instance of deceit and corruption, and even the extreme inequality and poverty- that the author has so beautifully depicted with an amazingly apt satirical style is in every sense applicable to the contemporary Indian society. Effortless read.
  7. Irrational exuberance – Robert Shiller – Exceptional analysis of cultural, structural and psychological factors behind formation of speculative market bubbles and, depressing troughs. Moderate read. Good reference material.
  8. Against the Gods – Peter Bernstein – This is an all-round, detailed look at risk – in life and investments. It is a historical narrative which draws upon developments in physics, mathematics, statistics, medicine, psychology, finance and economics to place the concept of risk in the right context. Indeed, it leaves the reader with further curiosity. Serious stuff but written in an entertaining style.
  9. Empires of the word – Nicholas Ostler – History of the word cannot be different from the history of the world. This history of languages is a mesmerizing journey into the world’s history taking various languages and their speakers as the medium.




The Actively Lazy Style; Of Life, and Of Investments


Blaise Pascal, the famous French physicist of the 17th century, had once said “All of humanity’s problems stem from man’s inability to sit quietly in a room alone.”

Understandably it is not easy to extol the virtues of laziness, or even of selective inaction. However, if laziness is resorted to consciously, with full control over oneself, in many situations it can work wonders towards attainment of goals and achievement of happiness. It can be of immense value for people in fields as wide ranging as sports, investments, science, archaeology , human relations, medicine and business management. Being comfortable with status quo, with environment, and with oneself can at times be crucial for flow of creative juices, for revitalization of thought process, for avoiding disasters, and for action later with renewed vigor and enhanced focus.

Why float like a butterfly; Just rope- a- dope, and sting like a bee

In one of the most eagerly awaited boxing matches in history – the “Rumble in the Jungle” in 1974 in Zaire, the bone-crunching power of the undefeated reigning champion George Foreman was pitted against the timeless agility, stamina and technique of former champion Muhammad Ali. The fight delivered one of the biggest upsets in boxing history as Ali went on to knock out Foreman. Ali’s win was attributed mainly to his makeshift strategy dubbed as “rope-a-dope”.

Ali was a nimble fighter with great footwork and stamina, and had a knack of scoring points with his lightning fast punches and jabs. However he realized early in this fight that his famed ability to “float like a butterfly, and sting like a bee” would come a cropper due to Foreman’s diagonal movements blocking his “floating space”. Ali instead came up with an improvised strategy –to lean against the ropes effectively luring Foreman to have a go at him. In all these rope-a-dope acts Foreman helped himself to a barrage of 20-30 punches over bursts of 15-20 seconds attempting to blast Ali out of the ring.

Spectators thought after seeing the first such instance that Ali was finished and it was a matter of minutes if not seconds before he was floored. However Ali was mindfully playing a patient game – deciding to do nothing except for closing the access to his face and head, thus avoiding any meaningful damage and inviting Foreman for the elusive kill. In doing so Foreman boxed himself out of the fight – he was sapped of energy and eventually knocked out in the eighth round.

The ant behavior on our part

So why are we unable to sit quietly without disturbing our limbs or vocal chords? Craving for action or to be seen doing something, bubbling energy, attempt to be in control, and the perception that doing more means getting more and that one will look smarter by doing so often push people towards perennial action mode. In many professions, we are expected to have an opinion on everything and cannot be seen as saying “I don’t know”.

Lack of skin in the game can transform into incentive-caused bias

There are instances where there is a misalignment of interests and outcome for the actor is different from outcome for the person experiencing the end results. Such incentive caused bias is often seen in investment management industry if fund manager’s compensation has low correlation with the investor’s portfolio returns.

Feedback loops not closed

In a situation where we have not done enough work to understand a problem, it is quite likely that we may yield to peer pressure, or may follow system 1 (the fast, associative, spur of the moment, intuitive and emotional part) of the brain to be spurred into action even if it’s not required.

Actively lazy in investments and life

Doing nothing – when market has leapt, or it has tanked, or a favorite stock in the portfolio has collapsed, or a stock has jumped quite fast though is still at less than price objective – is not easy even if often preferable. Selling too early, getting into a bad investment, excess portfolio concentration, high cost of doing business are some of the undesirable outcomes of high adrenaline activity in the field of investments.

Less number of decisions means less chances of wrong decisions This sounds counter-intuitive but the amount of discipline this can instill in an investor, and hence the benefit it can have for the portfolio, is amazing. Ace investor Warren Buffet goes to the extent of saying that investors should assume that they have only 20 stocks to buy during their life time and make their investment decisions accordingly.

Don’t try to jump over seven-foot bars; Look for one-foot bars that can be stepped over – With a lazy (actively, though) style an investor is able to steer clear of a stock, or some strategy that is out of her circle of competence. Actively lazy investors are comfortably able to avoid unnecessary bravado and temptation to stray into unchartered territories.

In Indian mythology Lord Krishna is also known as “Ranchhor” or “one who deserted the battle field”. Jarasandh, the powerful but evil king of Magadh, being hell bent on obliterating Krishna and his Yadav clan had once invaded Mathura. Mindful of the possibility of certain destruction of the city if there were to be a war, Krishna decided to lead the Yadav’s away from the battlefield to the faraway Dwarka where eventually the erstwhile dwellers of Mathura prospered after setting up virtually a new city. Thus, there are some situations where instead of grabbing a problem by its horns, a better solution can be found via a less active and seemingly even an inglorious route – possibly aided by an outside view, or by inversion. Or better still, not every battle in life is worth fighting.

Busy-bee investing is injurious to wealth – As investors we may face a situation where a stock we hold has fallen by 20-30% for some reason and there is an extreme urge to sell. Very often the reason for this decline is temporary in nature with low long-run relevance. Here, while the analysis should obviously be thorough it is important to be actively lazy in responding to the behavioral demons (that make us hyperactive and induce us to go for the elusive stock bottom).

Pulling out the flowers? – If a stock spurts by 50% then a high adrenaline strategy will call for selling the stock even if it, as per earlier high-conviction analysis, is set to grow by another 5x. This mistake is committed repeatedly due to investor’s inability to take a break from watching the stock prices continuously.

Stop chasing stocks; instead, buy when market offers them – If good stock buying opportunities are not there it is better to keep the powder dry and wait for opportunities to emerge rather than buying at any price.

The world would have been a very different (in fact, much worse) place had Adolf Hitler stuck to his original plan of pummeling all the western European powers into full submission before invading the Soviet Union.

WWII had been going very well for Germany in mid-1941. Entire continental western Europe was under its occupation. Britain, with its geographical advantage of being an island, had unleashed fierce resistance but it seemed like a matter of time before it would be down on its knees. USSR would not intervene as it was overawed by Germany’s might and also due to its non- aggression pact with Germany, and USA was largely out of the picture.

Amid a stalemate with Britain, Hitler somehow concluded that time was ripe to roll-out the next leg of his plan to conquer the world. He decided to attack USSR despite being advised against doing so by his best military minds, and being fully aware that USSR with its limitless depth, seemingly unending steppes and long, harsh winters had for centuries been the proverbial graveyard for invaders.

Haste to reach for the goals quickly in defiance of existing environment drove Hitler towards this fatal mistake. The ferocious resistance, followed by aggressive counterattack, by USSR’s red army led to the downfall of Hitler and his Nazi dreams.

Play to win, not to the galleries – Whether in investment or in some other walk of life, most of us fall prey to this fallacy where-in we work more to convince others – or even ourselves- that we are putting our best effort. Many fund managers churn their portfolio rapidly due to this behavioral bias.

Goalkeepers in soccer often succumb to this behavioral vice. In football penalty kicks often decide the fate of a match. Here speed of the ball after the kick is so high that the goal keeper can’t stop the ball if he waits for the penalty taker’s foot to hit the ball before making his leap. Instead he tries to read the body language and mind of the penalty taker to guess the direction of the kick – to his left, to his right, or at him as he stands in the middle – and makes his jump accordingly. As per a study of penalty kicks (source – Little Book of Behavioral Investing, by James Montier) roughly one third each of the kicks go to the left, right and centre. Further, the goal keepers leapt to the left or right on 94% of the kicks. Thus only in 6% of the shots the goalkeepers were standing in the middle – without jumping-even though 33% of the shots came at that position. Indeed the temptation to act overrides the commonsensical understanding that even if he rightly guesses the direction of the kick the goalkeeper does not stand more than 40-50% chance of stopping the shot in his left or right. On the other hand, if he were to keep standing at his position he would be able to stop 80-90% of the shots that came his way.

So, how to follow actively lazy style in investment

The key is to be aware of our predilection towards action. It is important not to confuse activity and results.

  • Reduce external stimulation of the mind – Cut off news, do not consume information with low shelf life, avoid newspapers and TV.
  • Practice and exercise – Read, analyze, discuss and gather evidence so that there is enough confidence to be lazy.
  • Recognize that most things are random, and generally have false causality – Then effort for control looks futile and refraining from high adrenaline action seems the better approach.


Escape from Freedom; The Glenn McGrath Model of Investment

Escape from Freedom; The Glenn McGrath Model of Investment

In his widely-acclaimed book “Escape from Freedom” (published in 1941) the German philosopher Eric Fromm extolled the virtues of reducing our own options – something that goes against the tenets of basic economics and even militates against common sense. He argued that lack of freedom represented by social or biological determinism made life easier. In this case with limited number of options, life has a well-defined structure with less requirement for decision making, low chances of confusion, enhanced commitment, and even lesser possibility of regret in hindsight.

Burning the Boats

Life in the ancient era was hinged largely on the above framework. There was this incident where a Chinese general called Xiang Ji set his army’s ships on fire on the night preceding an important battle with a formidable enemy – the Qin armies. As his troops watched the boats go up in flames they  realized that their rations also had been burnt down with the ships. From there-on they had only two options left – fighting their way out through the enemy ranks, or perishing in this self-imposed pursuit of glory. Armed with clear focus and absolved of fear, Xiang Ji’s heavily outnumbered army emerged victorious after a protracted set of battles defying heavy odds.

Even in the current era there are many instances where lesser number of options makes life less complicated and improves the average happiness levels. The tenacity and vigor that comes from shutting all doors save one can often lead to unexpectedly positive results.

More Options Better Than Less Options?

However in real world a rational human being (the “econ” in economics parlance) always prefers more options than less. A student is likely to be happier if she has admission offers from the three Indian Institutes of Management (IIM) at Ahmedabad, Bangalore and Kolkata than she is when she has just one offer – only from IIM Ahmedabad, even if the latter is considered to be much better than the other two IIM’s. Here the student gets more satisfaction if she has admission offers from Bangalore and Kolkata also since it adds to her self-esteem even though the latter offers are redundant in the face of the offer from Ahmedabad.

A football club manager wants to have 8-9 defenders in his squad of 25, even if he knows that 2-3 of them will never be used, even if he is convinced that the latter 2-3 defenders are not good enough to be in the first team, even if he knows that other 6-7 defenders are capable to carry through the season assuming the normal injury rates and form reversals. This is a case of over designing which eventually curtails the manager’s ability to rotate strikers as the season progresses. The manager, with his economically rational approach, gets more satisfaction in the knowledge that he has 4-5 additional back-up defenders versus the back up strength of 2-3 players that he may actually need.

Another example – an investment manager feels constrained if all his fund schemes are based on the same investment style. Most investment managers enjoy using discretion especially the one that comes with being in a position to apply various models and styles of money making. In this case the larger number of options add to the feeling of excitement, level of active involvement and sense of being in control which often act as emotional drivers for higher level of satisfaction.

However over-designing, or keeping all options open till end may not necessarily lead to the most desired outcomes.

Same line, same length, same height, same speed – ball after ball, over after over, spell after spell

Cricket lovers fortunate enough to have witnessed the great Australian test cricket teams of the nineties in action, would recall whom does the above description refer to. Glenn McGrath, arguably amongst the best fast bowlers of all times, will always be remembered for his persistent accuracy which led to his spectacular feats on record books and to his domination of the game in the nineties. He rarely tried variation, novelty or deception in his deliveries nor was he a speed merchant. McGrath used to surprise- even the best players of fast bowling- with his irritatingly repetitive but exceptionally accurate bowling spells. Most of his deliveries would be a couple of inches outside the off stump, would be of good length and at a pace of around 130-135 kmph.

McGrath had deliberately curtailed his armory and instead focused on perfecting one kind of delivery. He sent down similar deliveries over long spells and waited for batsmen to commit a mistake. This enabled him to curb his own mistakes as a bowler (as evidenced in his top class bowling averages and economy rates) as well as in reducing the need to make too many split second decisions (regarding what type of ball to deliver) before releasing the ball form his hand. Cutting down on options is what differentiated him – and fetched him spectacular success and provided elegance as a fast bowler – versus some other top class fast bowlers of his generation.

Where do investors stand

Admit it – when the friendly wealth manager suggests instruments like derivatives, commodities, cash equities, real estate, arbitrage fund etc doesn’t it feel like that the best way to go about it is to distribute the corpus amongst all these asset classes and instruments? Similarly, the freedom and the mandate to invest in any geography, in any asset class, and in any portfolio proportion is amongst the most alluring factors for a professional fund manager. Indeed, there are many fund managers who manage more than one fund schemes based on meaningfully different investment styles.

Consistently Strong Returns -Over Long Term- Demand Consistency in Style too

History is replete with examples that suggest that sticking to one style offers better success rates for investors. Warren Buffet (quality, margin of safety, buy and hold) and Charlie Munger (quality, buy and hold), Phil Fisher (quality, buy and hold), Ben Graham ( margin of safety), John Templeton ( contrarian), Peter Lynch (quality, bottom up), George Soros ( global macro, arbitrage), Howard Marks( margin of safety, arbitrage), Jim Simons ( quantitative strategies), Ray Dalio ( Arbitrage) etc are some legendary investors who have led the investment world with consistency and scale of their performances over long periods.

While they have different styles and philosophies for investment, one factor that separates these names from the “also rans” is that they stick to their styles, philosophies and principles with extreme diligence. Even as their styles have evolved over time they have never spread themselves thin by chasing too many ways of money making. Keeping down the number of fundamental options in terms of styles and philosophies at a minimal level has helped many of these super investors reduce the number of decisions they take thus shrinking the odds of mistakes, stay within their circle of competence, avoid procrastination, and remain focused.

There are Always Exceptions, But Not Many

Of course, Phil Fisher’s saying that “There are exceptions to every rule; though not many” is apt here too. There are some investors who have delivered good returns even with a medley of investment styles in action. However, such investors are much less in number as compared to the prophets of consistency named above.

Alignment of Philosophies of Life and Investments

Perhaps among the most important drivers of an investors’ performance over long term is if her investment style is aligned with her philosophy and perspectives on life in general. If one has done enough introspection then one will be clear on one’s basic value system, principles and philosophy of life. There can-not be a multitude of value systems and philosophies that a person can hold and follow in life. Accordingly, the investment style too must have some core, non-negotiable factors which are aligned with the person’s perspectives on life, and which if practiced with diligence over time can fetch healthy rewards. It is very important for an investor not to try to be someone who she is not.

Lessons From a Crash

It was the year 1987 AD. Berlin wall still stood tall in all its sadistic glory. Developed world was using computers of 386 vintage as a force multiplier in many fields. Back in India a new car called Maruti had recently been launched to challenge the duopoly of Ambassador and Premier Padmini.This was also the period when a certain Diego Maradona was setting football grounds on fire with his brilliant individual skills.
For the US stock markets,1987 was turning out to be another spectacular year. By August the benchmark Dow Jones Industrial Average (DJIA) index had registered about 40% gains for the year. In fact the five year bull run since 1982 had catapulted the DJIA 3 x.US economy too was dashing ahead having registered five straight years of expansion.
The tragic developments that were to follow – particular in October – would leave more than a hole on market psyche. Many large financial institutions received a big jolt, some smaller ones faded into oblivion, a large number of investors lost sizeable amounts in the markets, and many a promising career was cut short after this event, dubbed as the black Monday.
Unfortunately the financial world moved on post the 1987 crash without taking the lessons properly. Not surprisingly some avoidable though extreme disruptions, with some similarity to that of 1987, have been hitting the markets with remarkable regularity. Lessons from 1987 could have cushioned the impact of events like ASEAN crisis (1997), the LTCM disaster (1997), Tech boom and bust (1997-2002) and global financial crisis (2007-2009) – if not prevented them altogether. For the 1987 disaster the culprit was the same, eternal one – unfettered greed that throws caution to the winds. However this was the first time when the folly of greed was riding the dragon of derivative instruments. The latter inflicted the main damage once lust for easy money had blindsided market participants.

The Learnings First

Why did the markets fall precipitously on 19th October, 1987 ? To say gravity, won’t be an oversimplification.The markets had risen too high too fast and hence they were ripe for a rout.
The lessons for market participants (especially equity investors), financial institutions and regulators were quite clear if one analyses the events of that fateful period of October’87 –
1. If some profit seems too good to be true then chances are quite high it is so. It is important for investors to steadfastly refuse invitations for free lunches in markets.
2. At any point in time, inability to justify a course correction for markets in future does not guarantee continued momentum, or even status quo. For example, if market frenzy takes a stock to price/earning multiple of 45x – say, substantially ahead of historical and peer group valuations – then the stock is best avoided even if one cannot pinpoint even a single reason for potential correction.
3. Even simple looking derivatives should be handled with care. People with less than perfect, understanding of and, experience in these instruments should treat derivatives as nothing but weapons of mass destruction
4. There is another and deeper issue with derivatives. Superficially the outcomes and methods look as simple as they seem compelling. Thus slowly people get sucked into the cauldron lured in by specter of easy profits. After some time the application of a particular derivative instrument becomes so widespread that contagion risks grow exponentially and uncontrollably. Now one seemingly innocuous mistake by an untrained hand is what it takes to bring down the entire edifice. Even people who understand and are experienced in these instruments find themselves helpless once the genie has been set free.
5. Quantitative models, even if they are mathematically rigorous and practically simple, are unable to capture emotions and hence can become irrelevant precisely when they are needed the most.
6. A quantitative strategy based on assumptions on correlation – among certain assets – derived from intricate data from past can often fall flat on its face when markets turn irrational. These correlations can in no time swing from a sizeable negative value to a meaningful positive one. An asset supposed to hedge another one may end up doubling the exposure in reality thus piling in the misery.

Anatomy of a stock market crash

On Monday, October 19th, 1987, DJIA nosedived by 22% – the biggest ever single day fall. The index remained extremely volatile for the week though it closed the week above Monday’s closing.

The solid trailing performance over preceding five years had layered a lot of froth over the markets and was also converting investors into reckless risk takers. On October 14th, and 16th the index had fallen by 4% each. Interestingly, news flow leading into the disaster was not too conspicuous even in hindsight. Some examples –
* Surprisingly high trade deficit
* 30 year bond yield rose above 10 percent level for the first time in two years
* US treasury secretary warned that the US might stop providing support for the dollar
* Legislation was coming up in the congress to tax greenmail

However, a chart showing an eerie similarity between 1987 and 1929 crash had been doing the rounds since early 1987 which had prompted some prescient (and/or lucky) traders to go short on the market.


For the majority though the developments came as an avalanche from which some took a long time to recover.

The Mindset and The Protagonists

While psychological seeds for this disaster were sowed by widespread greed for easy money, by poor memory of market trends prior to 1982, and by an uncontrollable urge not to be left behind peers, there were three sets of protagonists in the mayhem around the black Monday. The three protagonists had one thing in common – they all were based on sophisticated strategies that seemed simple, elegant and practical. The three protagonists were –
1.       Risk arbitrageurs: Risk arbitrage (arb) desks at various financial institutions were thriving on betting on who would take over whom in the takeover boom of those days.The weapons for takeovers were high yield bonds which provided capital for a raider to make a run on the target company.
2.       Portfolio insurance buyers: Portfolio insurance is effectively a dynamic hedging strategy designed to prevent a stock portfolio dipping below a predetermined floor. As the portfolio value rises hedges are reduced. Hedge is increased as portfolio value declines and as that latter slips below the floor the portfolio is fully hedged. Thus the instrument looked like a remarkably simple way to enjoy best of both the worlds – participate in the upside if portfolio is moving up and limit your downside if the markets are tripping. The strategy was based on the now famous Black-Scholes equation for option pricing.
3. Cash – future arbitrageurs

The snowball …..

On October 14th, the Street realized that there was a bill in the congress that intended to tax greenmail. This would dim the prospects for many takeover in the works. As a result risk arb firms started a broad liquidation which in turn weakened the markets.
The drop in the market was felt by portfolio insurance hedgers who were forced into their own programmed selling which continued through 16th October, Friday.

…..Gathers Momentum….

Over the weekend – after running their models on Friday closing prices – many more portfolio insurers got ready to make adjustments to their positions to increase their hedges by liquidating stocks. It still seemed business as usual at portfolio insurance desks as models appeared to be in control and nothing had gone beyond the script.
However mutual fund clients of these portfolio insurers were panicking and giving sell orders. Redemptions on Friday and on weekend meant that a commensurate amount of their equity positions had to be sold.
On Monday, 19th October even before the markets opened portfolio insurers had sold S&P futures worth 500 m, about 30% of public volumes. Futures prices dropped precipitously – and stock markets had not even opened.
Now, as the chasm grew between cash and future prices, cash- futures arb teams waded in to gain from this widening gap. With market yet to open on Monday – 19th October, cash price was being assumed at Friday closing and as futures had dipped pre-market there was a seemingly big opportunity for cash – future arbs. However risk of gap down opening of stock markets that had somehow been overlooked, was to play out soon- and, painfully.
Here in futures market the cash – futures arb traders were the other side of portfolio insurance hedgers .These traders in turn were depending on stock market for their other side of the trade. Effectively the cash-futures arb traders were taking the market impact from the futures and transmitting it back to individual stocks on NYSE. In this normal link up between cash and futures markets the weak link was the difference between the time frames to transact in the stock markets, and in future markets. The latter was much more quicker. Further, liquidity in cash market was much lesser than in futures market. This proved to be calamitous that day for traders who had been lured in by the siren song of cash versus futures arbitrage.

…..Finally turning into an avalanche

Finally when the cash market opened it was at a breath taking discount to Friday closing. Due to this gap down opening of stocks, sell orders started building up and potential buyers, even the long term players, panicked effectively closing a liquidity tap that could have provided succor to markets. Thus stock prices started falling sharply prompting portfolio insurers to throw more sell orders into the futures markets. Dipping futures, in turn, pulled down the stock prices too.
The cascade in stock prices wreaked havoc on cash – futures arbitrage traders ( gap down opening of stocks turned their arbitrage opportunity on its head), who started limping to the sidelines thus depriving the markets of another source of liquidity. Meanwhile the portfolio insurers continued their selling spree even as liquidity was drying up. The result was that the DJIA saw the worst ever single day decline of 22%.

Shrug off  – the post script

The disaster with its genesis in unbridled greed, herd mentality, inability to raise even basic questions, and unrestricted application of derivative instruments by untrained hands – should not have come as a surprise. What was remarkable was the resilience post the disaster. The index retraced the losses in less than 18 months in a sense paving the way for the next disaster in mid -nineties.