2026-01-08 23:00:21

Kevin O'Leary isn't mincing words. Just because you've built a successful empire doesn't mean you know how to handle your money. That's the hard truth he keeps hammering home.

The real problem? A lot of self-made millionaires and billionaires treat their investment portfolios like a casino. They're chasing quick wins, riding emotional highs and lows, making impulsive moves. All the discipline and strategy that got them to the top in business? Somehow it vanishes when they sit down to manage their wealth.

It's a classic pattern. Someone crushes it in their industry, scales their company to extraordinary heights—and then turns around and gambles with the fortune they've built. Different skill set entirely. Building a business takes grit, vision, calculated risk-taking over years. Managing an investment portfolio? That demands patience, diversification, and the ability to resist the temptation of get-rich-quick schemes.

The disconnect is real. Street-smart operators who negotiated billion-dollar deals suddenly think they can time the market like day traders. They can't. Most end up losing significant chunks of their wealth because they approach investing the same way they approached making their first million—with ego and impulse.

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BankruptWorker

· 13h ago

Haha, that's why those big players make money quickly and lose just as fast. Business acumen and financial management skills are really not the same thing.

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OnChainArchaeologist

· 01-09 22:16

Nah, really, people who are good at business just become stupid when it comes to trading cryptocurrencies. I've seen too many cases. --- The biggest bug for wealthy people is thinking that their ability to make money can be directly transplanted into investing. It's hilarious. --- So, why is it that people who manage to take their companies public start gambling as soon as they see money... I just can't understand this logic. --- Kevin is right, being shrewd in business quickly leads to downfall in the crypto world. It's not an isolated phenomenon. --- Building an empire is easy; maintaining wealth is the real skill. Most people get stuck right there. --- I've heard too many stories of entrepreneurs who succeeded in business but ended up questioning their lives after being wiped out by a market crash. --- Why do wealthy people always think about doubling their money quickly, even though they all understand compound interest? --- Street smartness is no different from a newbie in front of an exchange — it's just that straightforward.

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PuzzledScholar

· 01-08 23:30

Well said, making money and managing finances are truly two different things. Someone who can handle a trillion-dollar business can turn around and become a rookie; it's really funny.

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Ser_This_Is_A_Casino

· 01-08 23:29

Haha, really, making money and managing finances are completely two different things. O'Leary is right about that. Basically, it's overconfidence. Being good at business doesn't mean you're good at financial management; the difference is huge. The most pathetic thing about these people is... they can build an empire but can't control their own money. Each one thinks they can beat Wall Street by trading stocks, but in the end, they lose everything, including their underwear. Serves them right. Yeah, they just can't play this game but still insist on going all in. Are they brainless or what? I've seen too many people like this—making big gains and losing even bigger. It's hilarious. It's really just a lack of good advisors, but they're too self-righteous to listen. So, do you think these people deserve it? Overestimating their abilities and pretending to be cool outside their range.

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DecentralizedElder

· 01-08 23:28

Haha, this is just too ridiculous. Being able to make money doesn't mean you can keep it. This is so true. --- Exactly, a bunch of bosses treat their accounts like casinos, and end up losing everything. --- The key is that little bit of self-confidence... I’m the top in business, but I become a chive in the investment market. --- Doing business relies on guts and vision, financial management relies on discipline... they are really two different things. --- A billionaire ended up bankrupt because he couldn't change his gambler's mentality, it's just ironic. --- Watching O'Leary criticize this every day, I actually think he's quite clear-headed... but how many really listen? --- Built a business for ten years, lost everything in three months of investing... why do so many still fail to learn? --- Ego really can destroy a person, especially those who have experienced success.

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SchrodingerGas

· 01-08 23:21

That's correct. This is a typical case of skill transfer failure. Building a company and managing assets are entirely different strategic logics. The high gas users on the chain are the same; even after spending millions of ETH on DeFi, they still suffer huge losses because they treat trading as gambling and haven't understood the relationship between market efficiency and risk premium.

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zkProofGremlin

· 01-08 23:16

This hits the nail on the head. The set of skills for doing business falls apart when applied to investing; they are truly two different things. Making money depends on being ruthless, managing finances depends on being smart. These two are fundamentally not the same. The wild methods used in entrepreneurship are basically suicide when applied to investing. I've seen too many news stories of big players losing everything. Once your mindset changes, everything is gone. Once you have some money, you start thinking like a gambler. To put it simply, it's about not knowing your own capabilities. Being good at business doesn't mean you're good at investing.

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