When "Sopranos" star James Gandolfini died in 2013, he left behind an estate worth $70 million. The musician Prince died in 2016, and earlier this year, the IRS valued his estate at over $160 million. Michael Jackson was worth $500 million when he died in 2009. Aretha Franklin's estate was worth as much as $80 million when she died in 2018.

And despite the ample resources available to each of these superstars, errors in estate planning basics prevented a smooth and orderly transfer of wealth to their intended heirs.

On today's show, we discuss how to prevent your own estate from getting tangled in red tape and bad blood.

Pop quiz: What do Black Tuesday 1929 and Black Monday 1987 have in common?

They both happened in October.

That's probably a big reason why October has a reputation for being the worst month for investing. But as we discuss on today's show, digging into the numbers and taking in the broader historical perspective reveals some more important lessons for investors who get spooked by volatility. We also bring that same long-term perspective to a couple questions our Keen Wealth clients have been asking recently.