My afternoon with Andre
A wide-ranging conversation on tennis culture, Wimbledon, Laver Cup, and the mindsets that shaped Andre Agassi's career.
This past weekend, I had the immense pleasure of interviewing Andre Agassi, a career highlight if ever there was one. A few months ago, Boss reached out to me about hosting a panel over Wimbledon finals weekend at Soho Farmhouse, an idyllic outpost of the members club in the Cotswolds. At the time, it wasn’t clear who I’d be interviewing and when they threw out Andre’s name my honest reaction was, fat chance! Surely he’d be too busy with commentating duties and building out Agassi Intelligence to chat with little old me.
Then, last Monday, the Boss team told me that it would indeed be Andre joining me on stage—or, really, a grassy field dubbed the Lazy Lawn. As you may have read in my last piece, I’d been having a rough go in London and was feeling trapped. Boss was paying me to host this event and I follow through on my commitments, so I couldn’t simply catch an early flight home and cut the “fortnight” short. But just as my enthusiasm for the tennis ecosystem was hitting an all-time low, this news hit me like a shot of espresso, waking me up from my jaded slumber and sending me into a mix of panic and excitement.
I’ve worked with Agassi’s team before and they’ve been early supporters of Hard Court, even giving me the exclusive on a deep dive into the racquet sports platform they’re building that involves AI models trained using the insights of both Agassi and Darren Cahill. But I’d never spoken to the man himself and, despite ample footage showing him to be a great interview, I was nervous about our chemistry and how he’d field some fashion-heavy questions (it was a Boss event, after all, and the stated goal was discussing tennis fashion and culture).
As with many things in life, all the fretting was for nothing. Andre immediately put me at ease, answering each question with a heavy dose of wisdom and humor, and happily trailing off into much more profound territory than some of the questions warranted. It was such a joyful ride that I wanted to share it in full with you, rather than editing it down to choice quotes. I’ve only edited it a bit for clarity, so it’s supersized but, I promise, worthwhile.
The first half focuses on Andre’s impact on tennis culture and style, as well as his rebellious streak, before we move into his role coaching Team World at Laver Cup, his long relationship with Taylor Fritz, how he feels about some of today’s athletes’ potentially distracting extracurriculars, and the tennis traditions he’d love to see change. Throughout the conversation, Andre looks back on his own experiences on tour in remarkable detail, reflecting on them with his trademark candor. If you’ve been considering signing up for a paid subscription, you won’t regret doing so today.
PS. For those who’d prefer to listen, I’ve included a rough recording of the talk—the audio fluctuates a bit, especially with audience questions at the end, but Andre is very clear and does a great job of reiterating any hard-to-hear questions. Please remember this was a live talk and not staged in any way, shape, or form as a podcast—when and if I cross into that medium, it will be significantly more polished. Enjoy!
