With a legacy of 73 titles and 23 Grand Slams, Serena Williams is arguably the greatest of all time. Although her days as a professional tennis player have ended, the bar for achievement keeps rising for this GOAT. Whether it’s juggling parental duties or expanding her beauty brand, Serena is consistently making headlines.

Speaking of headlines, the top fashion magazine Vogue recently collaborated with Serena’s brand WYN Beauty. On Tuesday, the brand announced this exciting partnership and celebrated with a luncheon. They took to Instagram to share pictures from the event, captioning it: “There are few things more inspiring than a table full of women who are making moves 🏆💪. Another WYNNING highlight this weekend was the VOGUE 100 x WYN BEAUTY luncheon hosted by our favorite boss lady @serenawilliams!” Serena herself chimed in with a comment, saying, “Such a great day!”

When Serena launched WYN Beauty in April, she had a clear vision: to create makeup that captures the essence of traditional cosmetics while being perfect for an active lifestyle. As she told Vogue earlier, “I wanted something that could keep up with me and make women feel amazing all day long, whether they’re at the tennis court, the office, or the playground.”

Well, talking about being active, Serena is quite active even after retirement, but in a different way. She explained, “But now, as a mother and entrepreneur, I’m up early, in bed late, on Zoom calls all morning, playing with my kids all afternoon. Active has a whole new meaning!” Serena described her life as an athlete as simple—a repetitive cycle of “train, sleep, train”—compared to the dynamic lifestyle of motherhood and business.

Reaching her current position took immense dedication and hard work from Serena, but she recently admitted to having made blunders along the way as well—especially with her venture capital firm, Serena Ventures.

Williams opens up about her first bad venture deal

In a chat with Andrew Ross Sorkin for the New York Times Events on December 6, Serena Williams reflected on her post-tennis career. She now boasts a net worth of $340 million as of May 2024. This financial success stems from her sharp business instincts and ventures like Serena Ventures, the venture capital firm she co-founded with Alison Rapaport Stilman. When asked about her best and worst investments, Serena couldn’t pinpoint a single standout, stating, “We have so many that we’re so proud of. We have a unicorn in our fund already. Our fund is only a couple of years old.”

Serena Ventures is notable for its commitment to diversity, with an impressive 79% of its portfolio comprising founders from underrepresented backgrounds—54% women, 47% Black, and 11% Latino. Founded in 2014, the firm aims to address significant gaps in venture capital funding for these groups. However, Serena also shared a lesson she learned from what she considers her “worst investment” experience during the firm’s early days.

“The worst is probably my very first investment. I started investing over 15 years ago now, and I invested in this one deal because this guy was doing it and this celebrity was doing it,” Serena admitted. Influenced by fellow stars, she made choices she wouldn’t make today and didn’t even know what “due diligence” meant back then.

Now, as she shines in her new ventures—like enjoying lunch with top fashion magazines for her beauty brand—one can’t help but wonder if there’s anything Serena can’t do. Her journey from being a tennis champion to business mogul is nothing short of inspiring. What are your thoughts on her incredible transformation?