From what I understand, any third party sponsorships (or income) arranged directly by the player (manager) without the involvement of the club does not get included in the cap. However any income the club has any direct involvement in must be included in the cap. So in your example Dexter, I would think that as the club contracted the company directly and knowing the player was an owner/shareholder/whatever, then I think it would have to come under the cap. Used to be that the club got players "second jobs" with sponsor companies as a way to complement their football income - in most cases the players in question probably couldn't have even found their way to said company's premises to perform their "second job"; but they had an employment contract with them and officially got a paycheck from that company. This has very much been cracked down on now - hence why Smith's work with News Ltd came under such scrutiny as they are part owners of the club. Some club also used to "employ" players' wives/girlfriends - again they rarely actually did any work for the club, but the paycheck was in the partner's name - again this is now much more cracked down on.