Steve Ballmer was an underrated CEO

Funny story. I used to see Steve almost every weekday for a couple of years.

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

First, I love this story. I'm on your side. For me personally, the most charming detail is that he paid in cash. I guess it was a while ago! Your story makes me think of the scene from the film "Casino" when the mafia guys spit into the "free" sandwiches that they give to the police. (Ref: https://www.youtube.com/watch?v=XPufB6oaJFE)

It is weird to me that a guy like that even bothers to pick up his own daily black iced tea. Once you are making a few million dollars per year (and you have a net worth > 1B USD), I would assume that everything would be brought to you. Literally, have an assistant who does all of this stuff and brings it to your office. The most highly paid people that I have ever observed up close were in non-stop meetings all day long -- talkin' money! They had no time to buy their own daily coffee or lunch. There was an assistant who would bring everything to their office. That said, maybe he did it to "feel normal". For any human being, having a net worth > 1B USD must really screw with your world view.