Afford Anything · Friday, October 23, 2026
Discussing self-made business founders, the podcast highlighted Dick Portillo, who used a thousand dollars cobbled together from the Marines and his brother to start a hot dog stand out of a shack without running water, eventually scaling it into a business sold for $1 billion.
“there's one of my favorite stories in the book is about Dick Portillo, who grew up in the projects and ended up selling a hot dog business for a billion dollars. out of Chicago, he initially had no money. And he went to the Marines, he got like $1,000 cobbled together, with a little money from his brother and started this shack that had no running water”