re: How to make $300k arbitraging credit card points and then pay zero taxes on it

Amex caps the grocery store 6% cash back/rewards on grocery stores at $6,000.

If you go into the comments in the tweet there is a Reddit thread where someone spent 8-12 hours per week for a year maximizing bonuses and got $32k in various perks but only $6,257 in credit card bonuses along with ~$10k in points. So 400-600 hours a year to earn $42k in total points and perks.

This $300k is complete hogwash unless you’re talking about a decade+ of churning, and that’s also incredibly unlikely since most perks are for first time users.

ETA- I found the original tax case that the OP is referencing and it was during an uncapped promotion Amex was running in 2013 and 2014. Not gonna happen today unfortunately.

According to the tax court ruling, he also had to pay taxes on some of the money when he directly bought money orders and/or reloaded prepaid debit cards. I’m not sure how much was generated that way.