Ben isn't running a charity. If he thinks this strategy will help increase the user base, he could be right. The only problem is that if that strategy works, he'll be losing money on almost every transaction. (ACH transfers are cheap, but they're not free.) Dwolla also has pretty limited fraud detection at this point, and no bonds in most states to serve as nominal protection (see http://www.facecash.com/legal/brown.html). So at some point the price will need to rise again.
If the strategy does not work, then this will just hasten the company's demise. There's a remote chance it could help catalyze an acquisition, but that's really remote.
I then thought for a minute that perhaps this was a step toward operating legally in states like Pennsylvania (see http://www.thinkcomputer.com/corporate/whitepapers/heldhosta...), which waives its money transmission regulations only if you do not charge a fee (a la Venmo), but since you'd have to pay a fee at $10.01, that doesn't make sense.
So honestly I'm not sure I get what's going on here.