Given that you're not satisfied with the Donor Lottery and want to gamble against "non-philanthropic funds," then you probably want to pool your money with all other gambling philanthropists before making a single large bet.
A single large bet prevents your winnings from averaging out against other philanthropists' losings (resulting in a worst outcome than just using the Donor Lottery).
If there are many gambling philanthropists, you can't go to the casino, because they probably don't have enough money to multiply all your funds by 1000x. You have to make some kind of extreme bet on the stock market.
If you want to ensure that you win the bet in at least one branch of the multiverse (haha), then you might roll a quantum dice and let it decide which stock you bet on (or against).
Two options I came up with:
I think occassionally some lotteries are positive or neutral-ish EV, when the jackpots are really big (like >$1billion)? Not sure. You have to check the taxes and the payment schedules etc.
I mean, if there were ANY widely-available, repeatable, +ev bets, they'd pretty quickly get dried up by just a few players who can spell "Kelly".
There are LOTS of negative EV bets available, if you think the distribution of 0.005% chance of $1000000 and 99.995% of $0 is better than a straight $1000.
Suppose that I have some budget set aside for philanthropic funding, say $1,000, but I think there are a big returns to scale, so that it would be >1,000x better if I had $1,000,000.[1]
What are my best options for some bets I can make to get some chance of turning that $1,000 into $1,000,000?
I imagine the bets are generally better the more positive their EV is (which in practice means the less negative the EV is), the easier they are to find (like if they're standardised), and the better their tax treatment is, especially if you repeat them multiple times (maybe they can be done by DAFs).
NB: I don't believe this