Jonathan established Millennium Drilling, a contract drilling company and one of his many energy ventures. Seven years after he founded the company, Millennium had contracted to drill approximately two hundred gas and oil wells for contract values estimated at $250 million on behalf of nearly 30 investment partnerships.
Jonathan purchased the apartment buildings for which he served as leasing agent and cleverly converted the apartment buildings into student rentals. By the time the savvy businessman was twenty-seven, he had already acquired and was managing one hundred and forty-four apartments with no assistance of outside investors.