Longtime Keen on Retirement listeners and friends of the firm are probably familiar with The Big Hat.

Matt Wilson, our Chief Investment Officer and President, is the proud owner of an oversized Dow 100,000 cap that he wears on our show from time to time. And when folks visit our offices, such as during our annual Holiday Breakfast, they often spot Matt's hat in his office and have a bit of a chuckle about its pie-in-the-sky prediction. More than once, I've heard someone tell Matt, "Gosh, I'll never see that in my lifetime."

But ... is the Dow hitting 100,000 really all that far-fetched?

On our final show of 2025, we look to market history and current trends to give you a head start in your financial planning for 2026.

I also share some stories from my big Hollywood red carpet debut as part of the Keen Wealth Foundation's charitable mission.