How much did you invest?
How much has he invested?
How much has the other investor invested?
(You may not know the answers to some of these questions)
Do you know why he has not given you shares in the business?
What arrangements are there for you to get your money back with any profit?
There is no reason for you not to have the shares. Of course, he may simply not have got round to doing the paperwork and issuing the certificates and sending return to companies house but that’s not going to take days.
The paperwork you need other share certificates and confirmation of the change of shareholder companies house.
I don’t accept what he says about other things needing to be paid for. You give him the money, he gives you the shares, if he wants to then lend the money to the radio station, he is at liberty to do so and the radio station can pay him back whenever.
In the short term, it’s probably going to take longer to do a deed of trust whereby he holds the shares on trust for you albeit that they are in his name, than it is to simply sell some of his shares to you. I would want that document as a minimum.
Can I clarify anything further for you?
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