I think that's the difficulty of being rational and prudent. A few lucky people will get lucky through chance alone. It doesn't mean the process was a good idea

I think that's the difficulty of being rational and prudent. A few lucky people will get lucky through chance alone. It doesn't mean the process was a good idea and the same is true of the reverse: you can have a great plan but sometimes chances get stacked against you. I loved the book "Fooled by Randomness". Well worth a read if you haven't. Your advice to your friend was sound. There's nothing to regret.