He barely has 5 BTC(at current value)left invested in CLOAK anyway. I thought about putting 1 BTC into CLOAK just for fun earlier, but liquidity is so low that that would double the price, even when spread accross bittrex and cryptsy (who share more than 99% of total CLOAK trading volume according to coinmarketcap.com). Investing 1.5 BTC would triple the price. Yea, I'm not gonna do that.

That goes both ways btw. Slippage is so bad, I doubt cashmen(why mEn by the way? how many are you exactly?) would get much more than 3.5 BTC back if he sold all his CLOAK at once.

But I guess it's a rather profitable investment if it gets you exclusive access to a coin's source code. Maybe he already made a deal with bob and sold it (or at least the parts that actually work)?