Let your kids fail (and I didn’t fail enough as a kid)

I recently came across this story on Medium and thought I’d continue this topic, albeit from a different angle.

I have four kids and my two oldest sons — nineteen and seventeen — have been through quite a few intense situations in recent years.

The other day one of them lost over $1,000 doing sports betting which is not even legal in some states in the US. When I say “lost”, I mean that he actually made money (hundreds of dollars) from his bet but the transfer to his account from whatever app he used is nowhere to be seen, despite his multiple outreaches to customer service. The funds he was using for betting were his own hard-earned money — he gives tennis lessons and gets paid. He’s worked many hours in recent months.

I knew that he was doing this betting thing. For one thing, he was using my credentials, as he’s not old enough to do it. Also, like I said, he was risking his own money. I don’t know much about the sports betting industry but I heard that it’s unregulated, meaning that if you can’t collect your money, you don’t have any power over the betting company. I warned my son about it but didn’t try to dissuade him.

Now the money is lost. This exchange is from a couple of days ago: