Tiger Woods and Vanessa Trump compare their distinct paths to wealth through investments and brands

Tiger Woods has turned his one outlet success into a broad business network under TGR Ventures, covering TGR Design’s high-profile courses, the TMRW Sports-run indoor golf league TGL, and the Sun Day Red apparel line launched with TaylorMade. His hospitality venture, The Woods Jupiter, combines dining and sports entertainment, while his investment portfolio features companies like Whoop, Hyperice, GOLF+, Future and Full Swing Golf.

In contrast, Vanessa Trump’s financial base is linked to a $1 million investment by her late father, Charles Haydon, in Rao’s Specialty Foods, which yielded a large payout when the company sold for $415 million. She also ran the La Poshett handbag line from 2010 to 2013 and owns upgraded real-estate assets in Jupiter, Florida, and a Manhattan apartment valued at around $3 million.