Serena Williams faces insecurities just like the rest of us.
In a conversation with her sister, Venus Williams, the 23-time Grand Slam champion, shared that she wasn't confident in her playing ability.
"I sucked. I was bad. I didn’t have it," Serena told Venus on their podcast Stockton Street. "I only hit lobs. Remember, I only hit lobs. I was terrible. I mean, even when I first turned pro, I was really bad. Not that I didn’t, but I just thought I wasn’t that good. I thought I could outlast people because I was small at the time. I thought I could outlast them and just be out there. And yeah, I never really thought about it."
Their father, Richard Williams, who was their coach growing up, told the sisters to pick a major tournament they could win, and that would be their goal. Venus chose Wimbledon, and Serena also wanted that one as well, but ended up choosing the US Open.
We are back in New York, diving into the meaning of fun amidst life's challenges-navigating bad dates, partying with your sister (and roommate) and exploring our complex relationship with practice. @Venuseswilliams pic.twitter.com/14SfAMk6Mw
— Serena Williams (@serenawilliams) October 1, 2025
"Then, when dad told us to pick a tournament to win so we could focus on the goal, you picked Wimbledon too. And then he said I needed to pick something different. So I picked the US Open, but I didn’t really think I would make it," Serena admitted.
Despite not wanting to originally focus on the US Open as a goal instructed by her father, Serena went on to win the 1999 US Open for her first Grand Slam win. As for Venus, she ended up winning her first Wimbledon match in 2000 when she defeated Lindsay Davenport.
Their first wins were just the beginning of their monumental careers. Serena would go on to win 22 more Grand Slam titles, and Venus would win Wimbledon again the following year in 2001, as well as three more championships in 2005, 2007, and 2008. Serena also had success at Wimbledon, winning seven championships in her career (2002, 2003, 2009, 2010, 2012, 2015, and 2016). Venus also found success at the US Open, winning back-to-back in 2000 and 2001.
When did Serena Williams and Venus Williams start their podcast?
The tennis pros announced their podcast last month, which is named after the street they grew up on. The sisters shared their reasoning behind starting the podcast is to share more with one another.
"As close as we are, we had to keep so many things distant because of our jobs,” Serena told the publication. "As much as she’s my sister, she’s also my opponent, and you can’t be as open as you want to be. So this a real opportunity to do something that we’ve been trying to do, and also just a discovery thing as well.”
Stockton Street airs Wednesdays on X.
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