Steve Ballmer was an underrated CEO

I can't speak to his business skills, but I can attest that he never once offered a tip for his daily black iced tea. We'd even have it ready for him before he showed up so he never had to wait! He would pay with cash, and I'd hand him his change and drink, and that was that.

It's funny to me now: one of the richest men in the world and he never once offered a tip.

Frugality aside, he was always very polite and warm so I can't be mad. Makes for a good ice breaker story.

Edit: holy moly, this is a sensitive subject. Please remember this was from a time before tipflation. Tipping meant you left your change behind once in a while only if you felt the desire to show appreciation. It wasn't an obligation. Yes, I still do think it's a funny story. Roast me for being entitled lol

We learned his schedule, we made sure to make his drink so it would be ready on time while also handling the hundreds of other orders in the morning rush. This is something we tried to do for every regular customer with a fixed order.

I'd argue that this sort of thing is well within the bounds of what was 'tippable' service back then.

But to be clear, tips weren't expected then like they are now. It was an infrequent thing. If you dropped your ~15¢ change into the jar once or twice a month, you were a generous tipper.

We served Steve for many years and he was definitely an outlier. He wasn't the only other customer that never tipped. But he was the only one that was famously rich, which is what made it so amusing to us.