【Event】What Losing Money Taught Me？
When we lose money in the market, the instinctive reaction is often: “Maybe I’m just not good at this.”
But the truth is surprising — some of the most influential figures in history also suffered huge losses in the stock market. And for many of them, those failures became the start of something bigger.
Take Isaac Newton.
During the South Sea Bubble in 1720, London was swept up in speculation. Everyone was talking about the stock — even café waiters were bragging about “guaranteed profits.” Newton stayed cautious at first. But after watching friends make quick money, he jumped in and made £7,000 — a fortune for him at the time.
He could’ve walked away.But when others made even more, he went back and bought at the top.When the bubble burst, he lost roughly £20,000 — worth millions today.
That’s when he famously said:
“I can calculate the motions of the heavens, but not the madness of people.”
Karl Marx also tried investing — and failed badly.
Hoping to improve his family’s finances, he put money into the hottest stocks of his time: railroads. He lost once, twice, three times — eventually to the point where his family relied on friends just to get by.
Those painful experiences pushed him to study how markets really work. His questions — Why do booms happen? Why does speculation take over? Why do crises repeat? — later formed the foundation of Das Kapital. In a way, the market became his toughest teacher.
Even Winston Churchill wasn’t spared.
In 1929, while visiting New York, he heard stories of investors doubling their money overnight using leverage. Fired up, he went home and put all his savings — plus borrowed money — into the market.
Then the crash hit. His portfolio collapsed, and debt piled up.To stay afloat, he spent years writing articles and giving speeches. Yet that grueling period sharpened his thinking and strengthened his voice — skills that later helped him lead Britain through World War II.
After losing money, what did you learn?
Everyone’s takeaway is different.
Some learn to cut losses.
Some learn position sizing.
Some learn not to chase hype.
Some learn to admit what they don’t understand.
Some realize investing is ultimately a long-term game.
What about you?
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I learn that holding onto a sinking stock is like clinging to a leaky inflatable float in the ocean. Eventually you will sink.
Turns out "all in" is a poker move, not an investing strategy.
I chased hype once. It was like running after an ice cream truck only to realise it was selling kale.
The market taught me that pretending to understand biotech or crypto tokenomics is like nodding along a Shakespeare play. You clap at the wrong time.
Finally I realise that investing is less about sprinting & more about surviving the marathon. You need to keep jogging even if your shoelaces are untied.
The market is both a stern teacher and also a mischievous prankster. It humbles me yet rewards me too. The only way to graduate is to learn & be wiser the next time.
@TigerEvents @TigerStars @Tiger_SG @Tiger_comments @TigerClub
I also realized the importance of risk management. Position sizing, diversification, and setting boundaries for myself became non-negotiable. Losses hurt, but they also forced me to build a system that protects me from my own impulses — especially during hype-driven periods when everything looks like “easy money.”
Most importantly, I learned to be patient. Not every opportunity is meant for me, and not every dip is a buy. Investing is a long-term journey, and losses are just tuition fees along the way. Each one sharpened my thinking, strengthened my mindset, and helped me grow into a more mature investor.
@TigerEvents @TigerStars @Tiger_comments
2. Take profits early, at least take partial. Especially when you are over allocated, or overvalued assets. TP on them first.
3. Do equal allocation and don't get too confident. Buy only on red days for better entry.
I also learnt that never be greedy and hope for more profits because your profit will not stay and wait for you. Your winner might just easily become your loser.
- do not fight the trend, follow it. When the market is going down, for example don’t rely on puts, switch to calls
- capital preservation is more important than profit. When the choice is between these two, don’t get greedy be conservative.
- position sizing less is better than more. Smaller sizes reduce losses big sizes have a chance of big gains but equally big losses
- never over extend margin and leverage. You will go bust fast
- markets are fickle and random, you may think you have it figured but you will be right only 50% on average. More than that you are a soothsayer
- and finally accept losses as a part of the trade. You can’t win every trade and life to fight another day.
The stock market is here always and there will still be another day to make money.
Dont despair by the losses even big boys also make mistakes.