I’m still profoundly grateful to @halfkelly for telling my story with such skill and care.
Risk of Ruin has long been one of my favorite podcasts and getting to be a guest on it was a privilege.
He had $87 in cash, and the rest of his liquid net worth was in...lottery tickets?
AKA an obvious sucker's bet.
But this game had an overlooked wrinkle.
So over months he bought millions of tickets.
Then he spent his free time thinking about how to buy even more.
It seems “know your customer” might mean very different things depending on which department is asking.
Imagine having this level of data and moral flexibility and still massively underperforming the S&P 500 on a risk-adjusted basis.
TIMES INVESTIGATION
How DraftKings Uses A.I. to Target the Gamblers Likeliest to Lose
Data science helps determine who receives betting incentives, but the company has resisted using similar technology to protect gamblers at risk of addiction.
nytimes.com/2026/09/19/busin… via @NYTimes
Mr. Doppy retweeted
I called Nevada Gaming over a year ago to inquire about the legality of casinos resetting slots that have progressive elements to them. My complaint specifically pointed to machines that had an accumulating equity feature that was not displayed in dollars and cents.
I’m going to start a long thread on how I optimized Chase rewards on my organic spend. I was simply trying to maximize the value of my points via merchant coding, an efficient portfolio of cards, adjacent rewards programs, & portals. To be clear, this is my logic, not my advice.
That wraps up the numbered portion (1–6). I’ll keep adding to the thread as things occur to me, just without numbering them from here.
Here is my manual spending summary from a few years ago with various valuation methods:
xitter.cf/mrdoppy/status/1089254…
Not a fan on the the new year end summary, I calculated the return on my credit card setup by hand. Lots of valuation choices, but I’m 5.50% to 13% back on every $1 spent in 2018, excluding referrals, no MS... just optimization. 🤓
