Jesse Livermore

I just inherited $5 million from my grandfather. I'm 35, make a good salary, and don't need this money to live. It's pure opportunity capital. My financial advisor wants me to put it in a diversified portfolio—index funds, bonds, some real estate. "Slow and steady," he says. "In 30 years, this could be $30 million. Don't gamble with your grandfather's legacy." But I've been studying markets for years. I see opportunities he doesn't. Tech is transforming entire industries. There are companies I believe in deeply. I could concentrate my bets and potentially 10x this money in a decade—or lose a significant portion. My grandfather built his wealth by taking calculated risks on specific businesses he understood. He didn't diversify; he concentrated. My advisor says that's survivorship bias—for every grandfather who succeeded, ten lost everything. I don't need to preserve this money. I could afford to lose half of it and still be fine. But is that permission to speculate, or is it precisely the thinking that destroys wealth? — The Windfall Inheritance in Greenwich

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