The Williams sisters have won a combined 30 Grand Slam singles titles. Venus accounts for seven, but former Williams coach Rick Macci recently argued that the elder sister would have had 15 to 20 more, had it not been for Serena.

Serena agreed, but what if we ran the same simulation for her? At the New York Times DealBook Summit, younger sis gave her thoughts.

"We had this rule that if we played against each other before the final, we had to win the title," she said. "I think Venus would have had a minimum of 15 Grand Slams if we didn't play. I would have had 30."

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The New York Times DealBook Summit featured Serena Williams and other luminaries in the business world.

The New York Times DealBook Summit featured Serena Williams and other luminaries in the business world.

Although many more Slam titles sound exciting to each sister on an individual basis, it was their unique rivalry that transcended tennis viewership around the turn of the century.

“Women sports isn’t having a moment, it’s always been there…we’ve always been great, you guys are just noticing,” Williams said. “Venus and I have been around forever and we've had the most viewers ever at the US Open, every single Grand Slam of any kind of female any women athlete ever, but it's also the fact that there's other amazing athletes that have been doing so well for so long.”

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In retirement, Serena’s harnessing everything she’s learned from tennis, from her toughest losses to the bravest victories, for a seat at the investor’s table—where she plans to use a non-traditional, “champion mindset” to change the world, one start-up at a time. As she said at DealBook, Serena Ventures is all about transcending her winning mentality from the tennis court into the investing industry, providing resources for early-stage founders that they would otherwise not have access to.

“We play to win” is the motto, and $111 million in inaugural funds are fueling the initiative to change the venture capital ecosystem from within.

“I never wanted to lose, but unfortunately, I think when you do lose, you learn some of the biggest lessons,” Serena said. “And every loss that I had, I needed 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, sucked.

“It was very difficult to watch go back and watch the footage of why I lost, but it also helped me though. Like with investing, if I do something wrong—if this didn't go well, why didn't it go well; what did we like about it, what can we learn from this—and so I’m bringing that tennis aspect across the board.”