The original grant of those $1.85 options was 2007-06-08 (200,000) and exercised 11,000 at $1.85 with 39,000 expiring leaving a balance of 150,000. So you can see he has had an active account since 2007.  

 

Previous balance 150,000 ( $1.85 options) 2010-01-13

2010-01-27 Direct Ownership 50 - Grant of options +300,000 (0..23 )

2012-11-05 Direct Ownership 50 - Grant of options +375,000 (0.1000 ) Balance 825,000