9 restaurants wealthy people eat at on weeknights that look completely unremarkable from the outside and that's exactly the point - Silicon Canals

"Last month, I found myself sitting in what looked like the world's most boring strip mall restaurant. Beige walls, no signage except for a tiny brass plaque, and a parking lot filled with understated luxury cars. I'd been invited by a source who'd built three successful companies before turning forty. As we ate perfectly prepared Dover sole at 7 PM on a Tuesday, surrounded by other quietly powerful diners, something clicked. This wasn't about exclusivity or showing off. This was about something else entirely."

"You know that Italian restaurant in the strip mall that your parents went to for anniversaries? The one with the faded awning and the same owner who greets everyone at the door? That's exactly where you'll find CEOs on Wednesday nights. These places offer something money can't buy anywhere else: anonymity paired with recognition. The owner knows to give them the corner table without asking. The waitstaff doesn't take photos."

Ultra-wealthy individuals often eat at unremarkable, familiar restaurants on weeknights to combine anonymity with quiet recognition. Longstanding suburban Italian places with familiar owners, unchanged menus, and discreet staff provide routine comfort and private spaces for CEOs. Reliable four-star hotel restaurants serve as practical venues where consultants and executives sketch deals after hours. These low-profile spots function as unofficial offices, confession booths, and sanctuaries away from public scrutiny. Consistent food, unobtrusive service, and predictable environments help powerful people relax or negotiate weighty decisions without fanfare. Weeknight dining habits therefore prioritize privacy, predictability, and trusted social rituals over exclusivity.

Read at Silicon Canals