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Portfolio Management puzzles, solved step by step

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  1. 004A portfolio has a 25% chance of a down year, and each year is independent of the others. What is the chance of at least one down year over ten years?Behavioural and decision trapsWarm upWealth managementRetirement and pensions

    Try it first

    Quick instinct: how likely is at least one down year in ten?

    Show the worked solution

    About 94%. The chance of avoiding a down year every single year is 0.75 multiplied by itself ten times, which is 5.6%. At least one down year is everything else: 1 minus 0.056, or 94.4%. Over a decade a falling year is close to certain, so a plan that treats one as a surprise is a plan built on the wrong base case.

    Why work through the chance of it never happening?

    Ask a commuter how likely they are to miss at least one train in a year of mornings, and the honest answer is: nearly certain, even if they miss one in a hundred. "At least one" questions have many routes to yes and a single route to no. Counting the one way it never happens and subtracting from 1 is always faster than counting every way it can happen. Here the only route to no down year is ten good years in a row, each with chance 0.75, so 5.6% of decades are clean and 94.4% are not.

    Chance of at least one down year, when each year has a 1 in 4 chance of falling50%100%25%144%258%368%476%582%687%790%892%994.4%1096%1197%12Years heldNo down year in ten:0.75 to the 10th = 5.6%
    With a one in four chance of a down year, the chance of at least one down year passes 50% by the third year and reaches 94.4% by the tenth, because the chance of dodging every one shrinks to 5.6%.
    The relationship
    P(at least one)=1−(1−p)n=1−0.7510≈0.944P(\text{at least one})=1-(1-p)^n=1-0.75^{10}\approx 0.944
    pthe chance of a down year, 25%
    nthe number of years, 10
    What it says in wordsThe chance of at least one down year is one minus the chance that every year is up.

    Why does a wealth desk ask a probability question like this?

    Because clients judge a portfolio year by year and plan over decades. A 25% chance in any one year sounds like a risk you might avoid; over ten years a down year is close to certain. The point of the number is to change the conversation from whether a down year comes to what the plan does when it does. Say the limitation as well: independence is an assumption. Real market years are not coin flips, and a regime of bad years clusters, which changes the count of down years without changing the lesson.

    Where candidates lose it

    The trap is adding: 25% times ten is 250%, which is obviously wrong, and candidates who spot that often retreat to 25%, which is just as wrong. The interviewer wants the complement said out loud.

    The quieter trap is getting 94% and stopping. On a wealth or pensions desk, the follow-up is what that means for a client, so have one sentence ready on setting expectations before the first bad year arrives.

    What the interviewer asks next

    • What is the chance of at least two down years in ten?
    • How many years before a down year is more likely than not?
    • If down years cluster, does the chance of at least one go up or down?
  2. 017A coin-flip bet wins Rs 1.5 lakh or loses Rs 1 lakh. Many people refuse to play it once. Why, and what is the chance of ending with an overall loss if you play it ten times?Behavioural and decision trapsHardWealth managementAsset management

    Try it first

    Over ten independent plays, how often does the total end in a loss?

    Show the worked solution

    People refuse because a loss hurts more than an equal gain pleases, but ten plays lose money only about 17% of the time. Each play is worth plus Rs 25,000 on average. Over ten plays, four wins and six losses break even, so only three or fewer wins lose: 176 of 1,024 sequences, 17.2%. Judging each bet alone makes a good repeated bet feel bad.

    Why does a bet with a positive expected value get refused?

    Ask someone whether they would bet their weekend on a coin flip to win a second weekend, and most say no, because losing the one they have feels worse than gaining a new one feels good. This is loss aversionThe tendency, documented by Kahneman and Tversky in prospect theory, to feel a loss more strongly than a gain of the same size.. If a loss feels twice as bad as an equal gain feels good, this bet's felt value is 0.5 x 1.5 minus 0.5 x 2 x 1, which is minus 0.25 lakh, so refusing it once is consistent with how the person feels, even though its expected value is plus Rs 25,000. The factor of two is an assumption for the arithmetic, not a measured constant.

    How do you get the chance of a loss over ten plays?

    Count wins. With k wins and 10 minus k losses the total is 1.5k minus (10 minus k), which is 2.5k minus 10 lakh. That is negative only when k is three or less. Because each win outweighs each loss, you can lose six flips out of ten and still break even, which is why pooling the bets makes a loss so much rarer than a single flip suggests. The number of ways to get 0, 1, 2 or 3 wins is 1 plus 10 plus 45 plus 120, which is 176, out of 1,024 equally likely sequences: 17.2%.

    Ten plays of a +1.5 / -1 lakh coin flip: how often the total ends in a loss0.1%-10.01.0%-7.54.4%-5.011.7%-2.520.5%024.6%+2.520.5%+5.011.7%+7.54.4%+10.01.0%+12.50.1%+15.0Total after ten plays, Rs lakhLoss, 3 wins or fewer: 17.2%Break even, 4 wins: 20.5%Ahead, 5 or more wins: 62.3%Average: +2.5 lakh10 plays x Rs 25,000
    Over ten plays the total ends in a loss only with three or fewer wins, a chance of 17.2%, breaks even at four wins with 20.5%, and ends ahead 62.3% of the time, with an average gain of Rs 2.5 lakh.
    The relationship
    P(loss)=∑k=03(10k)(12)10=1+10+45+1201024≈17.2%P(\text{loss})=\sum_{k=0}^{3}\binom{10}{k}\left(\tfrac12\right)^{10}=\frac{1+10+45+120}{1024}\approx 17.2\%
    kthe number of winning flips out of ten
    \binom{10}{k}the number of sequences with exactly k wins
    What it says in wordsAdd up the sequences with three or fewer wins and divide by all 1,024 possible sequences.

    What does this mean for how clients see a portfolio?

    A client who checks a portfolio every day sees each day as a separate bet and feels every loss. Looking at the same holdings less often pools the bets, and the pooled result loses far less often than any single period does. The economist Paul Samuelson told the story of a colleague who refused one such bet but would take a hundred; the lesson for a wealth desk is to frame decisions at the horizon the money actually has. State the limitation: pooling helps only when the bets are independent and the investor can survive the bad runs, and ten plays still lose 17% of the time.

    Where candidates lose it

    Candidates call refusing the single bet irrational and move on. The interviewer wants the mechanism, loss aversion, and then the arithmetic that shows why the same person might accept the bet repeated.

    On the numbers, the slip is setting the loss threshold at fewer than five wins, as if wins and losses were the same size. Write the total as 2.5k minus 10 before you count anything.

    What the interviewer asks next

    • How many plays until the chance of an overall loss falls below 5%?
    • What if the loss were Rs 1.4 lakh instead of Rs 1 lakh?
    • Why might a client rationally refuse even the ten-play version?
  3. 036Twenty fund managers have no skill at all: each has a 50% chance of beating the benchmark in any year, independently. What is the chance that at least one of them beats the benchmark five years running?Behavioural and decision trapsCoreFund selectionMulti-manager allocation

    Try it first

    Instinct first: how likely is at least one five-year streak among 20 unskilled managers?

    Show the worked solution

    About 47%, close to a coin toss. One manager beats the benchmark five years running with probability one half to the fifth, or 1 in 32. The chance that none of the 20 does it is 31/32 to the 20th power, about 53%. So the chance that at least one does is about 47%. In a crowd of unskilled managers, a five-year streak is almost as likely as not.

    Why is a five-year streak weak evidence of skill?

    Put 20 people in a room and ask each to call five coin tosses. Somebody calling all five correctly would look gifted, but with that many people, somebody usually does. The chance of a streak for one named person is small, but the chance that someone in a crowd produces one is large, and fund selection looks at the crowd. An investor who screens a category for managers with five straight winning years is sampling exactly the lucky tail of this distribution.

    Halve the crowd each year: a five-year streak survives more often than not20Start10Yr 15Yr 22.5Yr 31.25Yr 40.625Yr 5Expected managers still unbeaten25%50%75%100%02050100Number of managers with no skill20 managers: 47%100: 96%Chance at least one has a 5-year streak
    Twenty unskilled managers thin to an expected 0.625 unbeaten after five years, yet the chance that at least one of them completes the streak is 47%. With 100 managers it rises to 96%, so a streak in a large category says very little on its own.

    How do you compute at least one without adding up cases?

    Use the complement. The chance that at least one of many independent trials succeeds is one minus the chance that every trial fails. Each manager fails the streak with probability 31/32. All 20 fail with probability (31/32) to the 20th, which is about 0.53. One minus that is 0.47. The expected number of streaks is 20 over 32, or 0.625, which is a separate and also useful number: less than one streak on average, yet close to even odds of seeing at least one.

    The relationship
    P(at least one)=1−(1−0.55)20=1−(3132)20≈0.47P(\text{at least one}) = 1 - \left(1 - 0.5^{5}\right)^{20} = 1 - \left(\tfrac{31}{32}\right)^{20} \approx 0.47
    0.5^5one manager's chance of five straight wins, 1 in 32
    20the number of independent managers
    What it says in wordsFind the chance every manager misses the streak, then take it away from one.

    The limitation runs in two directions. Real managers are not independent, since many hold similar stocks, which makes streaks cluster and the calculation rougher. And some managers do have skill; the point is only that a streak on its own cannot tell the skilled from the lucky. That takes longer records, consistent process and a view on why the edge should persist.

    Where candidates lose it

    The common wrong answer is one in 32, about 3%, which answers the question for one named manager rather than for any of twenty. The next most common is adding 20 times 1/32 to get 62.5%, which counts the cases where two managers both succeed twice.

    Say the complement method aloud and give 47%. Then draw the lesson for manager selection in one sentence: a screen for long winning streaks mostly selects luck.

    What the interviewer asks next

    • How many unskilled managers would you need for a 90% chance of at least one ten-year streak?
    • If one manager in the group truly beats the benchmark 60% of the time, how likely is that manager to show a five-year streak?
    • How would you design a fund selection test that is not fooled by this effect?
  4. 049Fund rankings persist from one year to the next with a correlation of 0.2. A fund was in the top decile of its category last year. Where do you expect it to rank this year?Behavioural and decision trapsHardFund selectionPerformance analysis

    Try it first

    Where should you expect last year's top-decile fund to land this year?

    Show the worked solution

    Around the 64th percentile, still above average but most of the way back to the middle. On a normal scale, the top decile averages about 1.75 standard deviations above the median. With a correlation of 0.2, the expected position this year is a fifth of that, 0.35, which is about the 64th percentile. The quick linear version, 50 plus 0.2 x 45, gives the 59th.

    Why should a top-decile fund be expected to fall back?

    Think of a student who topped one exam. Part of that was knowing the subject and part was that the questions happened to suit them. Next time, the knowledge carries over and the luck does not. An extreme result is usually a mix of skill and a large dose of luck, and only the skill is expected to repeat, so the best forecast moves back towards the average by however much luck there was. A correlation of 0.2 says four fifths of last year's spread in rankings was the non-repeating kind.

    With persistence of 0.2, next year's expected rank hugs the middle00252550507575100100Percentile rank last yearExpected rank this yearperfect persistencepure luck: 50top decile: 96thTop-decile fundaverage z last year 1.75x 0.2 = 0.35about 64th pctexpected this year(shortcut: 59th)
    With a year-to-year correlation of 0.2, the expected rank this year is a flat curve close to the 50th percentile. A top-decile fund, averaging about the 96th percentile last year, is expected around the 64th this year, far below the diagonal that perfect persistence would give.

    How do you turn a rank correlation into an expected rank?

    Work on a normal-score scale, where the regression is a straight line through the middle. The expected score this year is the correlation times last year's score, so a correlation of 0.2 keeps one fifth of the distance from average. The top decile's average score is the normal density at its cut-off, 1.28, divided by 0.1, which is about 1.75. A fifth of that is 0.35, and the normal table turns it into the 64th percentile. If you skip the normal scale and pull the 95th percentile a fifth of the way from 50, you get about the 59th, a fair first answer.

    The relationship
    E[zt+1∣zt]=ρ ztzˉtop 10%=φ(1.28)0.10≈1.75Φ(0.2×1.75)≈0.64E[z_{t+1} \mid z_t] = \rho\, z_t \qquad \bar{z}_{top\,10\%} = \frac{\varphi(1.28)}{0.10} \approx 1.75 \qquad \Phi(0.2 \times 1.75) \approx 0.64
    \rhothe year-to-year correlation of rankings, 0.2
    z_tlast year's normal score
    \varphi, \Phithe standard normal density and cumulative probability
    What it says in wordsNext year's expected score keeps only the correlation's share of this year's distance from the middle.

    Then say what a fund selector does with it. Chasing last year's top decile buys mostly luck at a high price, often just as new money floods in. The answer is not to ignore performance but to weight longer records, look for a process that explains the result, and set expectations that even a genuinely good fund will usually rank well below where it did in its best year.

    Where candidates lose it

    The two extreme answers both lose the point. Expecting the fund to stay in the top decile ignores that a correlation of 0.2 is weak. Expecting it to fall below average overshoots: regression pulls results back towards the middle, not past it.

    Say one fifth of the distance, give the 64th percentile on the normal scale or the 59th with the quick version, and explain that the difference comes from how extreme the top decile really is. Then draw the selection lesson.

    What the interviewer asks next

    • What persistence correlation would keep a top-decile fund in the top quartile on average?
    • How does the answer change if you look at five-year rankings instead of one?
    • Why do flows into last year's best funds tend to make this problem worse?
  5. 062A household keeps Rs 5 lakh in a fixed deposit at 7% while carrying Rs 3 lakh of credit card debt at 36% a year. What does keeping both cost them each year, compared with using the deposit to clear the card?Behavioural and decision trapsCoreIndian wealth managementWealth management

    Try it first

    Roughly what does keeping both cost a year?

    Show the worked solution

    About Rs 87,000 a year, and more after tax on the deposit interest. The card costs 36% of Rs 3 lakh, Rs 1,08,000. Using Rs 3 lakh of the deposit to clear it gives up 7% on that money, Rs 21,000. The difference, Rs 87,000, is a certain loss every year the household keeps both, paid for the comfort of a bigger deposit balance.

    Why do people keep both?

    Because money gets labels. The deposit is the emergency fund or the daughter's education money, and touching it feels like failing; the card is day-to-day spending and feels temporary. A rupee is a rupee whatever label it carries, so money earning 7% while debt costs 36% is simply borrowing at 36% to lend at 7%. The habit has a name, mental accountingTreating money differently depending on which mental category it sits in, a term from the economist Richard Thaler., and it is one of the most common and costly patterns a wealth adviser meets.

    Interest a year, Rs: the labelled-safe money is quietly the expensive choiceKeep bothRs 5 lakh FD at 7%, Rs 3 lakh card at 36%+ Rs 35,000 earned- Rs 1,08,000 paidNet: Rs -73,000Pay the card offRs 2 lakh FD left at 7%, no card balance+ Rs 14,000 earnednothing paid on the cardNet: Rs 14,000Cost of keeping both, a year, before tax on the deposit interestRs 87,000
    Keeping both earns Rs 35,000 on the deposit and pays Rs 1,08,000 on the card, a net of minus Rs 73,000, while clearing the card leaves Rs 14,000 of interest and no card cost, so keeping both costs Rs 87,000 a year.

    How do you get the number right?

    Compare two whole choices. Keep both: the household earns Rs 35,000 and pays Rs 1,08,000, a net of minus Rs 73,000. Clear the card: it earns 7% on the remaining Rs 2 lakh, Rs 14,000, and pays nothing. The cost of a choice is the difference between the two outcomes, not the interest bill on its own. That difference is Rs 87,000, the same as 29 points of rate gap on Rs 3 lakh.

    The relationship
    cost=(36%−7%)×3 lakh=29%×3 lakh=87,000\text{cost} = (36\% - 7\%) \times 3\text{ lakh} = 29\% \times 3\text{ lakh} = 87,000
    36%the card's annual rate, an illustration; confirm the card's actual rate
    7%the deposit rate
    3 lakhthe money that could move from deposit to card
    What it says in wordsThe yearly cost is the gap between the two rates applied to the amount that could be moved.

    Tax widens the gap. Deposit interest is taxed at the household's slab while card interest is paid from income already taxed. At an illustrative 30% slab, confirm the current rates, the cost rises to about Rs 93,300. The honest limit is liquidity: a family with no buffer at all may need some cash on hand. Here the Rs 2 lakh left in the deposit is that buffer, so the case for keeping the debt is gone.

    Where candidates lose it

    The trap is answering Rs 73,000, the household's net interest bill, or Rs 1,08,000, the card interest alone. Neither is the cost of the choice. The cost is what changes between keeping both and clearing the card.

    The quieter miss is accepting the labels, treating the deposit as untouchable. The interviewer is watching whether you see through the label to the rate gap, and whether you can say it to a client without making them feel foolish.

    What the interviewer asks next

    • How much of the deposit would you keep as a buffer, and why?
    • How does the answer change if the deposit has a premature withdrawal penalty of 1%?
    • What other everyday decisions share this pattern of borrowing dear while lending cheap?
  6. 078You bought a stock at Rs 800. It now trades at Rs 500, and your updated estimate of fair value is Rs 450. Do you hold it until it gets back to Rs 800?Behavioural and decision trapsWarm upAsset managementWealth management

    Try it first

    Which numbers belong in the decision?

    Show the worked solution

    No. The Rs 800 you paid does not enter the decision; on your own numbers the stock is worth less than it trades for. Getting back to Rs 800 needs a 60% rise. Your own value of Rs 450 sits 10% below the Rs 500 price. Holding it is a fresh decision to own an overpriced stock.

    Why does the purchase price feel like it matters?

    Someone who paid Rs 2,000 for a concert ticket will go out in a storm with a fever rather than waste it, although the money is gone either way. The only question left is whether the evening is worth it now. Money already spent is sunk: it is the same whatever you do next, so it cannot help choose what to do next. The purchase price of a stock is exactly that kind of number.

    The purchase price is not on the decision; only today's two numbers are400450500550600650700750800850Rs 800: what you paidsunk, not a live inputPrice today Rs 500Your value Rs 450+60% needed just to get back: irrelevant to the choiceThe live gap: value is 10% below today's priceTest: would you buy this stock today at Rs 500 if you had never owned it? If not, holding it is the same bet.
    The Rs 800 purchase price sits outside the decision, and the 60% rise needed to reach it is irrelevant; the live comparison is today's price of Rs 500 against your updated value of Rs 450, which says the stock is overpriced.

    How do you say it so it sounds like judgement rather than a slogan?

    Turn the question round. If you had Rs 500 in cash today and no history with this stock, would you buy it at a price above your own value? If the answer is no, holding it is the same bet in disguise. The anchoringLeaning on a reference number, here the purchase price, when judging something that does not depend on it. pull comes from the Rs 800, and the disposition effect, holding losers to avoid booking the loss, is a well documented habit among professional managers as well as individuals.

    Then give the honest limits. Your Rs 450 is an estimate, so ask how confident you are and whether anything has changed that the price already reflects. A booked loss can also offset gains for tax, which is a reason to act, not to wait. Replacement matters too: the money should go to whatever has the best expected return per unit of risk, which may or may not be this stock.

    Where candidates lose it

    The trap is answering the question as asked, with a view on how long the stock might take to get back to Rs 800. That accepts the anchor, and the interviewer is testing whether you reject it.

    The opposite slip is a flat sell with no reasoning. Say the sunk cost point, give the would-I-buy-it-today test, then note that your Rs 450 value is an estimate that deserves a second look.

    What the interviewer asks next

    • Your value was Rs 900 instead of Rs 450. What changes?
    • Why do managers hold losers longer than winners, and how would you guard against it in your own process?
    • How would you explain this to a client who refuses to sell below cost?
  7. 091A trader bets on a fair coin, starting at Rs 1,000 and doubling the stake after every loss until a win, then starting again. The trader has Rs 63,000. What does each cycle win, how often does it wipe out, and what is the expected value?Behavioural and decision trapsCoreHedge fundsRisk management

    Try it first

    What is the expected value of one cycle?

    Show the worked solution

    Each cycle wins Rs 1,000 with probability 63 in 64 and loses Rs 63,000 with probability 1 in 64, so the expected value is exactly zero. The capital covers six stakes, Rs 1,000 up to Rs 32,000, so six straight losses, a 1 in 64 chance, wipe it out. Doubling down turns many small wins into one rare, large loss without creating any edge.

    Why does it feel like a sure thing?

    A driver who never buys insurance saves the premium every month and feels clever for years, until the one accident. Doubling after each loss produces a long run of small wins because the one outcome that loses, six tails in a row, is rare, but when it comes it is sixty three times the usual win. Short track records of such strategies look excellent, which is exactly the danger.

    Each loss doubles the next stake until the capital runs outLoss 1stake 1kLoss 2stake 2kLoss 3stake 4kLoss 4stake 8kLoss 5stake 16kLoss 6stake 32kRs 63,000 gone64k?No moneyfor 64kbars: stake on that tossline: total lost so farOne cycleWin Rs 1,000chance 63 in 64Lose Rs 63,000chance 1 in 64Expected value0Over 50 cycles, chanceof at least one wipe-out54%
    Six straight losses with doubling stakes of Rs 1,000 to Rs 32,000 use up the whole Rs 63,000, and the seventh stake cannot be placed; the cycle wins Rs 1,000 sixty three times in sixty four and loses Rs 63,000 once, for an expected value of zero.
    The relationship
    E=6364(1,000)−164(63,000)=984.4−984.4=0E = \tfrac{63}{64}(1{,}000) - \tfrac{1}{64}(63{,}000) = 984.4 - 984.4 = 0
    63/64chance of at least one head in six tosses
    1/64chance of six tails in a row
    What it says in wordsFrequent small wins and a rare large loss cancel exactly on a fair coin.

    What does this teach about judging a strategy?

    Run it 50 times and the chance of at least one wipe-out is about 54%, yet most individual traders running it for a few weeks will show a smooth profit. A win rate says nothing on its own; what matters is the size of the losses relative to the wins, and whether the worst case can end the game. Selling far out-of-the-money options has the same shape: steady premium income, and occasionally a loss that erases years of it.

    Say the limitation of the fix people suggest. More capital only pushes the wipe-out further out and makes it bigger: with infinite money and no stake limit the strategy would work, and nobody has either.

    Where candidates lose it

    The trap is being impressed by the 98.4% win rate. The interviewer is checking whether you weigh outcomes by size as well as frequency.

    The second loss is saying the strategy is negative in expectation. On a fair coin it is exactly zero; the harm is in the shape, a small chance of ruin, not in the average. Say both halves.

    What the interviewer asks next

    • The coin pays slightly less than even money. What happens to the expected value?
    • Where do you see this payoff shape in real portfolios?
    • How would you size risk so that no single loss can end the strategy?
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