The Stacking Benjamins Show · Friday, October 2, 2026
OG strongly advises against relying on guaranteed income streams in retirement, calling it a 'fool's errand' and a 'giant waste of time.' He argues that the primary risk in retirement is not a lack of guarantees but money failing to outpace inflation, which can happen with overly conservative, flat-rate income plans.
“Guaranteed income is... It's like my good friend Tommy Boy said, if you want me to take a dump in a box and mark it guaranteed, I can do it. I got time. But all you're getting is a guaranteed piece of crap.”
“The reality is that the... It's funnier if I don't laugh, but you guys are laughing so it makes me giggle. Listen, the number one risk to people in retirement is not guarantees. It's the fact that their money doesn't outpace inflation.”
“So if all you have is... a guaranteed tips ladder i mean there's some inflation protection there allegedly but but if you've got you know a bond ladder or god forbid a stupid annuity it's like This stream of income is going to be flat as your costs blow past it and double over a quarter century.”