AMERICA'S MOST MANIPULATIVE BILLIONAIRE

The inside story of how Bob Brockman, the secretive billionaire who allegedly masterminded America’s biggest tax-evasion scheme, used “Darth Vader” contracts to overcharge auto dealers and finance Robert F. Smith’s private equity empire.

- CHRIS HELMAN

EVER SINCE FORD MOTOR COMPANY BEGAN SELLING ITS MODEL T IN 1908, FEW PIECES OF TECHNOLOGY HAVE BEEN AS IMPORTANT TO CAR DEALER PROFIT MARGINS AS THE DOCUPAD.

The 45-by-29-inch flat screen sits atop a salesman’s desk, giving him the ability to quickly coax customers through what would normally be mountains of paperwork. By enabling car buyers to check boxes with a stylus and sign contracts on the interactive screen, the DocuPad takes the friction out of a car salesman’s stock in trade—the upsell.

In a 2019 court deposition, the secretive Robert Brockman, 79, whose enterprise software company, Reynolds and Reynolds, sells DocuPad, offered a rare peek into the microeconomics of car sales. Brockman said the DocuPad enabled finance managers to upsell by at least $200 per transaction in a business where margins on every car sold or leased are typically razor-thin. “You recover the initial cost of DocuPad very, very quickly,” Brockman said, alluding to the $10,000 startup fee, plus an ongoing $1,000 monthly license. “And then, from that point on, it is a massive generator of profits.”

Naturally, a dealer can get the DocuPad only if he’s also a licensee of one of Brockman’s integrated dealer management systems—digital platforms for everything from parts inventory and service scheduling to the machines that secure the thousands of keys at an average dealership. When you have thousands of captive dealers locked into multiyear contracts, those fees turn into $1 billion, with annual income estimated to be $300 million. And Brockman controls 98% of it through an offshore trust, a stake worth at least $3 billion.