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 just have them get some and start getting comfortable with having a wallet somewhere? 
 he's more like here's a shit load of money and I want bitcoin. 
 well that IS rather awkward if you've got their fiat...

buy ⅓ of their stack now and sit on the rest 
 oh, no. I'm not and don't intend to be in the middle. We were just talking and he probably got "it". 

It's more about me being uncomfortable with the ATH enter. I'm afraid he could do something stupid like sell it when the price dips... 
 Just tell them to DCA 
 And what's the reasonable DCA strategy here?

Let's say you have $1m.

(AFAIK, statistically it's better to go all in). 
 But if you go all in you wont have the conviction to hold it to 300k 
 When I was in stonks, I DCAd but at some point I sopped and just went all in for an asset I liked.

My gains were much higher ... 
 Sorry I tossed a number without context, they need to hold against a 70% draw down 
 exactly. I believe he would.

Still it doesn't make me any more comfortable.

Orange pilling at 15k, that was much easier ... 
 Tell them it’s their money and to grow some balls and do whatever the fuck they want because you’re not their babysitter. 
 I'm the one who's uncomfortable :)

I need a pair too I guess 😂