Jamie Oliver — The Crusading Chef ($300M)

Oliver built a $300 million empire from his Naked Chef roots: cookbooks (8 of the 10 bestselling cookbooks in the UK are his), Jamie's Italian (once 45+ locations worldwide), kitchenware lines, and a magazine. Then Jamie's Italian collapsed into administration in 2019, closing 22 UK restaurants and costing 1,000 jobs — the biggest restaurant chain failure in British dining history. Oliver personally lost an estimated $13 million. He pivoted to YouTube (7 million subscribers), children's school food campaigns, and his Essex home cooking content. The empire crashed, but the brand survived. Not every chapter is profitable.