A few years ago, Scott Painter had it made. He was wealthy, handsome, and smart, a TED and Davos guy who hung out with Elon Musk and Richard Branson. “Everything in my life had gone unbelievably well,” he says. “Just off-the-chart success.” Over two decades, he had started dozens of companies and raised more than $1 billion in venture funding before finally hitting upon his Really Big Idea in 2005: A company eventually called TrueCar would bring price transparency to the sneaky world of auto salesmanship and give consumers leverage by telling them exactly how much other people were paying for cars.
For car shoppers, it was nirvana: no more haggling, no more waiting for that gold-chained salesman to talk to his manager to “see what I kin do.” Instead, you just went to TrueCar.com, typed in your ZIP code and the make, model, and extras you wanted (don’t forget the fuzzy dice!), and printed out a voucher, redeemable at your local TrueCar dealer, with a guaranteed low price. It was free and easy. And dealers paid TrueCar only if the lead turned into a sale—$299 for new cars, $399 for used.