Lose big or win small? Here’s my experience
Lose big or win small? Here’s my experience
All of us run our business with one target – to create financial wealth, leading to freedom. The more money you have, the more choices you have about how you want to lead your life. Eventually, you want to reach the place where work becomes an option. You do it because you want to, not because you have to.
I am addicted to my work, and I love it and creating wealth is a fun side effect, but keeping money is almost as hard as earning it.
Don’t get me wrong. I am not extravagant. I am not drawn to big brands and I wear my 8-year-old shirts with love. I don’t buy things on debt and the only product I change before it's worn down is my computer.
But you can lose money in many ways. Sometimes you can lose money because you are trying to grow it.
I have been listening to the famous investor, Peter Lynch’s book ‘Beating the Wall-Street’ this week and it reminded me of an important lesson that I learnt two years ago.
It’s better to collect small wins with lower downside, then wager big and lose big.

I learned this lesson by losing $12,000 dollars.
I bet big and lost bigger than I expected.
I took a little break and came back with a different strategy. One in which I am distributing risk and making defensive moves. It’s working wonderfully!
Defensive players always last longer. They are there when everyone else is washed out and gone home.
Have you heard of Michael Burry? He got famous for making millions of dollars in 2008 when he preempted the housing market crash.
Well, last year he lost big when he predicted a stock market crash that never materialized. He walked out of his calls with heavy losses. Will he try that again? I don’t think so.
This is the problem with betting big. You win big once, sometimes twice but then you end up making a bad call and losing everything you built.
This happens in business too, and yes, this also happened to me. In 2022 I invested a significant amount of time and resources in building a product in a new, untried niche.
I expected it to go big. Sadly, it didn’t find any takers. I could have created great new products in that much time or money for our market, but I didn’t.
Big bets don’t always materialize. Smaller bets may or may not pay big, but they keep you in the market longer.
It’s a good lesson to learn and I am keeping it close to my heart
And yet… I know I am going to try something bigger soon
That’s just the crazy risk-taking entrepreneur inside of me. Inside of you, inside of all the people who are reading this newsletter.
I know we’ll all do it again, but hopefully just enough that even if we fail, we’ll get up, dust ourselves off and start walking again.
Good luck!
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Cheers!
Your best friend in business
Cyril “Jeet”
Of Teknikforce
