What Venus Said About Losing
The moment that stayed with me from Boomi World 2026 had nothing to do with product roadmaps.
Steve Lucas, Boomi’s CEO, was on stage with Venus Williams, and he asked her whether she really worries about losing. She said yes. Absolutely. And then she said something I’ve been turning over in my mind since: a win glazes things over. Even a barely-squeaked-through win still comes with that elation, and elation doesn’t make you look at yourself. A loss does. It makes you sit down and ask: am I being honest? Am I doing things the right way?
I’ve attended enough of these keynote conversations to know when someone’s giving the audience what they came for and when someone’s actually saying something true. This was the second kind.
She talked about her father driving her and Serena to practice in a Volkswagen Bug, playing audio cassette tapes about foreclosures. She was six, seven, eight years old. She still doesn’t know how to do a foreclosure, she said, laughing. But it gave her something harder to name: a way of thinking. The idea that you work it out yourself. That you don’t wait for someone to hand you the answer or tell you that you deserve a lucky break. You earn it, or you don’t.
There was a stretch of the conversation about health that the room went quieter for. Venus talked about Sjögren’s syndrome and about adenomyosis, a condition where endometrial tissue grows outside the uterus, and described it as this large mass that shed at least once a month. She said there were two occasions during her career when tennis’s anti-doping agency contacted her, not to say she’d tested positive for something, but because her blood counts looked so bad they weren’t sure she was alive. She talked about all of it without self-pity, which is a much harder thing to do than it sounds.
Steve Lucas shared that he’s been a Type 1 diabetic for thirty years, managing daily with a pump and a sensor. He said watching someone like Venus be openly vocal about invisible battles made it easier for people who feel alone in theirs.
I think about that, working in technology, where we spend so much time talking about systems and optimization and very little time acknowledging that the people running those systems are carrying things nobody put on the agenda slide.
Venus said something else I keep returning to. About winning. She said learning through winning is probably harder than learning through losing, because once you find what works, you protect it. You stop risking. You stay comfortable. And comfort is the end of winning at any real level. You have to keep letting go of the thing that got you there.
She’s back on the tour after two years off, recently married, and by her own account still figuring it out. Which is maybe the point. Seven Grand Slams, four Olympic medals, a fashion label, a wellness company, decades of advocacy for equal pay that started when she was sixteen years old, and she’s still standing at the baseline asking herself the same question anyone starting over asks: do I still want to go through this?
She said the will has to be organic. You can’t manufacture it. But you can ask yourself what you would do if you weren’t afraid, and then do that.
I thought about that on the flight home.
