You can only really do that if you have hundreds of millions and can negotiate with a major bank to get it done. Most companies don't trade options until after the lockup, and even if they did, you are restricted from doing so by the contract.

You also have to put up a huge amount of capital upfront to purchase the options. For Mark Cuban, this could be done on credit to the bank, but likely not possible for a single digit millionaire.

It was only during a unique period of irrational exuberance that banks were open to underwriting options for such new and untested equities.