A stupid idea, but could work

He's not allowed to tell anyone, but who enforces this? He could 'secretly' tell his friend, then that friend could paint some crappy 'art painting', then schlap a 29.5 million price tag on it, he could buy that 'art painting', then sell it in the market for 'whatever people think it's worth', which would probably be pennies, so that's one easy way to do it.

People aren't honest, so there would've been about 30 million different sneaky ways of doing it very quickly and easily. It's NOT HARD to spend money quickly without gaining any assets!

So many junkies have done it, so many women that inherited a lot of money did it, so many lottery winners became broke very fast... it's not brain surgery, any fool can lose a lot of money quickly. Even those stipulations don't really mean much, they just make it barely more inconvenient - still super easy.