Practice.
Assume the stocks you are manipulating are bid at 99.99, ask at 100.
3 - Your friend's first few sell orders at $0.01 or better are filled at about $99.99.
Your buy orders go unfilled.
4 - If your friend sold enough shares, the algorithms notice someone aggressively selling. They may undercut and sell at 99.99 or even 99.98.
The algorithms also place a few buy orders at 99.96-99.97.
5 - Your friend's trades (assuming he is placing multiple orders, and is selling a lot) execute and drive the price down to 99.96-99.97 or so.
6 - The algorithm's buy orders at 99.96-99.97, are filled by your friend's sell orders.
7 - Price back up to 99.99.
8 - Algorithms eventually sell the shares they bought at 99.96 at 99.99.
Sum total: the algorithms made a few pennies off your friend. Your DJIA short does pretty much whatever it would already have done.