In my career in real estate, I’ve been involved with a number of property renovations. A true structural remodel isn’t just about applying a fresh coat of paint or updating the surface aesthetics. The real value is created when you go behind the drywall: upgrading the underlying plumbing,
…
At least six months ago, Heather saw something on Instagram that she knew would get my attention. Andy Roddick was going to host an immersive tennis experience. I was immediately intrigued.
There were two reasons. First, I’ve always thought Andy was an incredibly bright and cerebral person.
…
There is a distinct magic in stepping out of a world-class venue and into a global transit hub, reflecting on the sheer physical ambition it takes to make both exist in a world-class city. Sitting in the grandstands at the U.S. Open in Flushing Meadows and then heading home through John F.
…
There is an unmistakable, humbling weight to a match where, as it unfolds, you realize your opponent is simply better than you in every conceivable phase of the game.
It wasn’t just that I was losing points; it was the realization of total mastery across the board.
…
Remembering Who You Are
Reflections on Mick Jagger, Norman Lear, Tennis, and the Hidden Importance of Memory
The other night we hosted a live ball session at The TenniSphere with a group that included a lot of younger players. At one point I put on some Rolling Stones music and found myself doing a little arithmetic in my head.
…
I was watching the new Rafael Nadal documentary on Netflix when something his Uncle Toni said stopped me:
That line followed me onto the court.
Because despite all the matches I’ve played, despite knowing—intellectually—that it’s “just a match,” I still felt the familiar surge: the tightening chest,
…
Last week, my reflections were guided by Charlie Munger’s favorite mental model: inversion.
Rather than asking how to design a good life, the question was simpler and sterner: What does a bad life look like—and how might we avoid it?
…
I recently won my first doubles tennis tournament in a few years. This was the most satisfying because we won four matches on three surfaces, with one of the battles being quite challenging, requiring a come-from-behind victory.
It took longer than I expected—and probably longer than I wanted—but in retrospect,
…
Barcelona, the zoo, clay courts, and the art of living awake
We were in Barcelona—intentionally and accidentally at the same time.
Heather and I arrived after spending the prior week at the Rolex Monte‑Carlo Open,
…
Sometimes the Place Trumps the Play
On Trade‑Offs, Tennis, and the Economics of Time
Thomas Sowell famously defined economics not as money, markets, or math, but as the allocation of scarce resources that have alternative uses.
…
