

How important is failure in life? Different people, different answers! But for Serena Williams, it is one of her greatest sources of life lessons. Instead of dwelling on her failures, she transformed each failure into fuel for her return, emerging stronger every time. Now, in a candid conversation, she reveals how those very failures shaped her legendary tennis career and her rise as a successful entrepreneur. Curious to learn how she transformed her losses into her triumphs as the great?
Williams has often highlighted how her losses during her professional career helped shape her personality and how she applied those lessons to build her entrepreneurial personality through Serena Ventures. A 23-time Grand Slam winner, Williams has not been idle since retiring in the 2022 US Open third round after losing to Ajla Tomljanovic. Post-retirement, the Olympic gold medalist shared with Vogue her desire to “evolve towards other things that were important to her.” Recently, the WTA legend shed light on how her successful tennis career contributed to her indomitable spirit, helping her establish herself as a businesswoman.
During a session at the DealBook Summit with host Andrew Ross Sorkin, Williams delved deeper into how she tackled her losses and how the mindset she developed from defeat made her a successful athlete. “I never wanted to lose. But unfortunately, I think when you do lose, you learn some of your biggest lessons. And I kind of—every loss that I had—I kind of needed that to actually become Serena Williams, or I would have never been this person had I not taken some of those really, really hard falls and some losses that, quite frankly, s****d,” said Williams. Her words echoed the greatest lesson she learned from failure, survival. Williams not only survived but also showcased a spirit that inspired the next generation of athletes.
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“I am a moper,” Serena declared proudly, highlighting that it’s not a crime to feel bad about defeats. However, she further explained, “I definitely mope for a little bit, but then I do something about it. And I would say if I lose, I’m watching the film. And that was very hard and very difficult to watch—to go back and watch the footage of why I lost. But it also helped me, though, because it was like, A., I never wanted to watch that footage again. And B., you have to see why you didn’t win. Like with investing, if I do something wrong—and I tell my team all the time—if this didn’t go well, why didn’t it go well? What did we do about it? What can we learn from this? So, bringing that tennis aspect across the board.” Williams helped her followers understand that she was never truly separated from tennis. Even post-retirement, she applied her tennis lessons to build a thriving business empire, including her beauty initiative with WYN Beauty.
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Interestingly, becoming an entrepreneur was always Serena Williams‘ Plan B while she was still playing tennis. In a TikTok video, she explained how she planned an alternative career for post-retirement and proudly invested in 85 companies.
Serena Williams revealed how she has been an active investor parallel to her tennis career
In March this year, Williams sat with her TikTok followers to reveal how she has been an investor while being an established tennis player. “So I invest in a lot of companies, early companies, so think early stage, where companies have just started. And, I’ve always done this, I’ve actually been investing for over 14 years,” Williams revealed surprising her supporters how she has planned her life so well. She continued, “Just been an entrepreneur, while I was playing tennis, it’s super important for me to make a plan B while I was doing my plan A. Sounds weird, like a plan B. But it was fun, it was really important for me to do that, said Williams. “So, in my personal portfolio, I have invested in over 85 companies, maybe? Also, 14 are unicorn and a few decacorns,” she added. Williams’ confessions highlighted how successful her business portfolio has been. Not only did she work hard for her athletic career but she put equal efforts in her entrepreneurship.
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Serena Willims’ indomitable spirit and resilience became an inspiration to women athletes, mothers, and all the women out there who aspire to be successful and independent. Williams showcases that with hard work and the right intentions, it is never impossible to live your dreams. What do you think about it?
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