In June 2024, Roger Federer (my favourite tennis player) gave the first commencement address of his life at Dartmouth College, and he chose to open it with a question for the graduating class.
He told them he had played 1,526 singles matches over his career and won almost 80% of them, and then he asked what percentage of individual points they thought he had won across all those matches. The crowd guessed high, somewhere around 70%, and someone called out 65%.
The actual answer was 54%, which means Federer lost 46 out of every 100 points he ever played but still finished his career with 20 Grand Slams and 103 titles.
Source: Roger Federer, Dartmouth College commencement address, June 2024
It’s not just Federer, but the rest of the sport’s greats also sit in a startlingly narrow band on this measure.
His point wasn’t just about tennis. It was something that can be applied to a lot of other disciplines including investing and trading. Even the best investors get many decisions wrong and that too after extensive research. A successful intraday trader punches multiple trades every day and I’m sure that their win rates would be at best 7/10.
What’s important to internalise is that when you attempt many things, you will fail a lot but you should stop treating each individual loss as a verdict on you.
Your portfolio behaves in almost exactly the same way, because your returns don’t come from a headcount of correct calls, they come from a small number of positions doing a very large amount of the lifting.
Even Rakesh Jhunjhunwala Got Plenty Wrong
We remember the Big Bull for Titan, which he bought in 2002-03 at around ₹40 and which is around ₹4,700 right now (a staggering 100x+ return). But what almost nobody talks about is everything else he owned, because he held over 30 listed stocks at various points and a fair number of them turned out to be duds.
Sources: Business Today (Titan, Mandhana), Business Standard (A2Z), PrimeInvestor (concentration), BeMoneyAware
He was fairly relaxed about the whole thing, and in one interview he said that his failures were far less known than his successes and that he wasn’t as smart as people made him out to be.
The Mistake The Rest of Us Make Instead
Peter Lynch has the best line for what most investors do, “Selling your winners and holding your losers is like cutting the flowers and watering the weeds.”
Warren Buffett liked that line so much that he picked up the phone and called Lynch to ask permission to quote it in a shareholder letter.
Let’s take an example of portfolio over five years. Take two investors holding the same ten stocks with the same entry prices, where the only thing separating them is what they choose to do once something has run up.
Both of them were right exactly 60% of the time, and their results were drastic.
Looking at this another way and again in a tennis context, Investor A won a lot of non-important points while Investor B won the most match-defining points. The single position that ran to +300% did more for Investor B than the other nine combined, which is the whole game in one line.
Where The Same Maths Turns Brutal
A trader takes far more decisions than an investor does and gets feedback on them far faster, which means this same asymmetry compounds much harder in whichever direction it happens to be pointing.
SEBI’s FY25 study on equity derivatives found that about 91% of individual traders made a net loss. But it’s not that 91% of traders are getting their direction wrong, because plenty of them maybe right but what actually sinks them is the shape of their wins and losses, with profits taken quickly and losses held on to indefinitely.
Consider two traders over 100 trades each.
Trader A is right twice as often as Trader B and still goes home poorer, which is the entire argument compressed into one table.
Michael Mauboussin, a famous investor and author, says the same thing rather more plainly in his book More Than You Know, where he writes that in any probabilistic exercise the frequency of correctness does not matter and it is the magnitude of correctness that matters. He calls it the Babe Ruth effect, after a baseball batter who got out constantly but is still remembered as one of the greatest hitters the game has produced.
What This Could Mean For You
All of this is easy to say while looking backwards. Cut the losers, let the winners run, and the maths takes care of itself.
In real time you have no such labels. What you have is a position down 30% and no way of knowing whether it is a Mandhana or a Titan going through one of its bad years. Titan fell sharply in 2008 and spent long stretches going nowhere before that, and Jhunjhunwala had no way of knowing in 2003 which one he was holding. He also sat on Mandhana for years, which turned out to be a loser that he let run.
A falling price tells you what the market currently thinks, it doesn’t tell you whether you are wrong. And vice-versa.
So the useful question isn’t how to pick the winners in advance, because nobody can. It’s how to set things up so that being wrong doesn’t ruin you. A few things that could potentially help:
- Plan your exit before entering:
Defining your exit strategy (importantly your stop loss) while being calm, typically before you enter the trade. It helps you avoid emotional negotiation when a trade moves against you. The stop loss defines your average loss, which is critical to profitability. - Write down what would break the thesis, not a price target:
Share prices are volatile and just a dip in the price can’t be your sell signal. You sell when the fundamental reason you invested in the asset no longer holds true. - Risk only a small, defined slice on each position:
Decide upfront how much a single trade or holding is allowed to lose, and size it to that limit (say for eg. 5% of your portfolio per investment). When no single loss can hurt much, you can be wrong often and still be fine, which is how you lose battles without losing the war.
None of this means being right doesn’t help. It does, and it’s worth working at. It’s just that a loser can only take 100% from you, while a winner has no limit, so how often you’re right matters less than how much you make when you are.
To Sum It Up
You are going to take a very large number of decisions over your investing and trading lives and you will get a lot of them wrong, which isn’t a sign that something has gone wrong, it’s simply the job.
Federer lost 46% of every point he ever played, and Jhunjhunwala lost most of what he put into Mandhana and DHFL and many others, but they still won big.
What both of them managed to do was keep the losses small enough to survive so that the wins had room to matter, which is really just another way of saying that you can lose plenty of battles as long as you protect your capital and win the war.
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Vijay
CEO – InCred Money
P.S. I share my thoughts on Investing and the Economy regularly. You can follow me here.
