38. Kathy Ireland - $500m

Supermodels aren't always credited for having the greatest level of intelligence. Kathy Ireland makes a fallacy of that idea. Her business acumen is every bit as sharp as her looks, and she has stacks of cash as evidence. In fact, she's so smart she outwitted a major retailer.

Having spent a lot of time modeling other people's clothes, she started designing them in 1993 and struck a deal with Kmart. The clothes flew off the shelves, and Kmart was soon ordering a whole range bearing Ireland's name. Realizing that her name had just as much value as the clothes, Ireland founded 'Kathy Ireland Worldwide' (now there's a choice of brand name that shows ambition) and started dealing with retail outlets herself, breaking the Kmart link and pushing to get her goods in as many stores as possible, worldwide. Branching out into supplying home goods as well as fashion items, the company now generates over $1.5bn in sales annually.

NEXT


Copyright © 2026 CultureHook