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The housing market lottery.

Happy Monday, my friends. Welcome to another week of Apex Money. My name is J.D. Roth, and I’ll be your host for the next few days.

Actually, I’ll be your host in abstentia. I’m prepping this week’s installments on Memorial Day — before I fly out for my arctic cruise. Today, if all has gone according to plan, I should be Tromsø, Norway, where I’m scheduled to switch from the first cruise to the second. (I’m doing back to back cruises on the same boat — 23 days on the Norwegian Star.)

In a way, travel is a gamble. Things go wrong. Part of being a good traveler is learning to go with the flow when things happen. Speaking of which, all three of today’s stories are about gambling…

The last gamble of Tokyo Joe. [Chicago magazine] — “From his perch on Solano’s North Side, running Rush Street nightclubs like Faces and Bourbon Street, Ken Eto served as the Chicago Outfit’s most adept minority relations specialist — a gambling czar of the highest caliber, able to extract millions of dollars over the years from Chicago’s Puerto Rican, Black, and Chinese American communities.”

“I placed my first wager when I was ten. I’ve gambled more than $1 million since.” [Maclean’s] — “I loved the waiting that came with gambling: those final, dramatic moments of uncertainty, when a last-minute field goal or three-point shot could alter the result of the game. The feeling of anticipation— that’s where I got the high. And when I had several bets going on at once, it felt like my brain was on fire, the ultimate stimulation.”

The housing market lottery. [A Wealth of Common Sense] — “Financial success comes from some combination of hard work, discipline, patience and luck. That last piece is usually the biggest wild card…The 2010s and 2020s for the housing markets will lead to similar good or bad luck depending on your timing.”

Okay. That’s it for today. I’ll be back tomorrow with more great stuff. See you then!