There's always a positive story. But people hardly ever share their thousands of negative stories. Borrowing to invest is a big risk and in this guy's situation would just be for greed. He's paid of his mortgage, any more would just be extra, but of course takes quite a risk. From my experience it feels a lot better to miss out on more (essentially not needed) profit than to see your life savings or (god forbid) a debt going down the gurgler because your investment guess was wrong. It's not an easy game for people these days in light of short sales, bots and algorithms. Getting a profit is great but I still think take it and definitely don't go into debt for the hope of more... not when it's just about greed -IMO of course.