Of course he will. He certainly can afford it with the...

Of course he will. He certainly can afford it with the compensation he's been on. Well over $1.4m in the money for doing nothing but converting his options. However I dare say by the time he converts them the share price should be quite lower to reflect a fair market cap. Still will be massively in the money though.

That's a fair decent chunk of shares to hit the register too. When he sells to cash in for his retirement fund and/or at minimum sell ~4m shares to cover the $365,000 hopefully shareholders don't panic sell with him which generally tends to happen when insiders sell a large portion. I've seen even the most seasoned cheerleader with pompoms and all sentiment change over insiders selling under $50k for taxation purposes - this may have a much greater effect than that.