My Biggest Money Mistake: Knowing the Winners and Owning None

My Biggest Money Mistake: I Knew Google, Amazon & Facebook Would Win — and Owned None of It

Key Takeaways

Greg's biggest money mistake wasn't in business — it was using Google, Facebook and Amazon to make money without ever owning a share of them.
He acted as an operator (using the platforms) instead of an owner (holding equity in clear industry winners).
Amazon rose about 318,000% from its 1997 IPO — $10,000 then would be roughly $31 million now.
The same dot-com-style cycle is repeating in AI right now — a second chance to think like an owner, not just an operator.
Educational only — the lesson is the mindset, not a stock tip.

What was Greg Cassar's biggest money mistake?

Greg's biggest money mistake was using the era's winning tech platforms to make money without ever owning a piece of them. He was advertising on Google within months of launch, was on Facebook within two months, and did more than $10 million in sales on Amazon — yet he never bought and held the stock of any of them. He was an operator, not an owner.

Why isn't knowing the winner enough?

Spotting the winner is only half the equation. Greg used those platforms brilliantly to grow businesses — and they all worked — but he never asked the owner's question: can I own part of this business, hold the stock, and ride it long term if it's a clear industry winner? Recognising the trend without acting on it left the biggest gains on the table.

How big was the miss?

Amazon rose roughly 318,000% from its 1997 IPO to today — meaning $10,000 invested at the IPO would be worth around $31 million now. It was the biggest of the three, but the pattern was the same across all of them.

Is the same opportunity happening again?

Yes. Greg's point is that the same dot-com-style cycle is now playing out in AI. The takeaway isn't which stock to buy — it's the shift from operator to owner: as the next platform wave plays out, think about owning the winners, not just using them. Then check whether you're actually on track to compound your money over the years ahead.

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Read the full transcript

This is my biggest money mistake — and it has nothing to do with business. Chances are you've probably made the same mistake, and the exact same cycle is happening all over again, so it's really worth learning from.

I knew Google was a winner. I was advertising on that platform within one to three months of when it came out. I knew Facebook was a winner — I was advertising on it within two months of it coming out. I knew Amazon was a winner; I did more than $10 million worth of sales on Amazon. But was I smart enough to buy any of the stocks and hold them long term? No — unfortunately not.

But the exact same cycle, like the dot-com boom, is happening right now in the AI space. Effectively, I was being an operator rather than an owner. I was using those amazing technology platforms to make money — which was great, and all of them worked — but I wasn't really thinking about it like an owner: Can I own part of that business? Can I own the stock? Can I ride it long term if it's a clear industry winner?

Amazon went up 318,000% from IPO to now. That means $10,000 invested back in 1997 would be worth $31 million now. Crazy — and it's the biggest out of all of them.

Did you make the same mistake as me? Are you going to learn from it — or are you on track now to really compound your money as this AI tech boom happens?

On businessinvestfreedom.com I've put a quick retirement calculator. You put in some info — what you're trying to achieve — and answer a couple of questions. It takes about two minutes, and it'll show you a graph of whether or not you're on track to retire. And if not, it'll give you some free resources on what you can do about it. Check that out. Have a great day.

Disclaimer: This content is general education only and does not constitute financial advice, tax advice, or investment advice. Past returns (such as Amazon's historical performance) are not indicative of future results. You should consider seeking advice from a licensed financial adviser before making any financial decisions.