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Kevin O’Leary says most “successful” entrepreneurs are still one bad day away from broke.
On The Iced Coffee Hour he laid it out straight: the real milestone isn’t a big net worth on paper. It’s $5 million liquid in T-bills. That’s the number where your family is safe no matter what happens. Everything else is just theater.
He argues you should grind hard for that first $5M in pure cash, stay disciplined, and only then start playing with stocks and other assets. Most people never get there, they look rich but can’t actually raise serious cash when shit hits the fan.
As a guy building, this one hit different. The idea that true freedom comes from boring, safe liquidity instead of flashy assets feels brutally honest.
We chase “rich” vibes while ignoring real security. Liquidity isn’t sexy, but it’s the actual superpower when markets crash or opportunities appear.
This conversation genuinely recalibrated how I think about money goals.
What’s the net worth number that would actually make you feel “I’ve made it” — and why?
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