When World Wrestling Entertainment (WWE) prepared for its IPO in 1999, the company faced skepticism from Wall Street. The question was how to present WWE as a serious business opportunity — and two women became central to the strategy.

The first strategic decision was to make Linda McMahon, then WWE’s CEO, the face of the company to investors, rather than her husband, Chairman Vince McMahon, who was best known for his on-screen persona. Positioning Linda was a bold, counterintuitive move, but her command of the details, poised presence and clear leadership instantly elevated WWE’s credibility with analysts and institutional investors.

The second decision involved timing. WWE launched its IPO on the same day as the highly anticipated offering of Martha Stewart Living Omnimedia. This pairing worked brilliantly. The media, already committed to covering Martha Stewart’s debut, felt compelled to cover WWE’s IPO as well, drawing attention to Linda McMahon’s leadership and framing the company as a serious, credible business.

Fast forward to today, and that early strategic thinking is still paying off. WWE, now part of TKO Group Holdings, just struck a blockbuster deal with Netflix to stream Monday Night Raw. From skeptical investors to global entertainment dominance, WWE’s journey is proof that bold decisions and smart positioning win big.