Interesting question! I’ve stopped talking business or gambling full stop after to many beers – it’s great to get to know someone, but if often ends in regret. Business in pre-drinks, then if they want a few more after that I try and change the subject.
I remember when I first started building websites at around 16 I thought I’d come across a goldmine in Google Adsense, building sites and then just clicking on the ads regularly and building up a small fortune. Of course I got banned for life pretty quickly.
Also when getting the RCM business cards I thought I ordered 2000 of them all with the wrong phone number on them. I’d given it to the designer as an example and planned to change it later but totally forgot.
Nothing THAT embarrassing, but I have time left!