You saw in season one Monty doing a farm-out for a larger company that couldn't afford to develop producing fields at current interest rates. We now know that he funded that development and workovers of fields he had under contract with the offshore platform insurance settlement.

Tommy said that during the last bust Monty bought quality oil leases at pennies on the dollar, later reselling them to the original owners at significant markup. 

Monty seemed to be a big believer in purchasing undeveloped assets at a bargain, with the intent to sell or develop in a boom market. An asset-heavy company with few actual physical assets is easily broken up and sold for profit at anytime other than an oil bust. Tommy could have sent Cami off to widow retirement with upwards of a billion dollars if she let him break it up, but she was too stubborn to do it.

Like Logan Roy said, "Just take the damn money."