Scott Painter's Entrepreneurial Journey

A story about Scott Painter, a serial entrepreneur who repeatedly tried to revolutionize the auto industry online, including major successes and dramatic personal setbacks.

"Scott Painter started as a Spanish interrogator in the army. Then in the late 90s, he became VP of marketing at 1-800-CARSEARCH and 1-800-DENTIST. He created consulting companies helping businesses transition to ecommerce.

Then he started this crazy run in the car industry. He founded Cars Direct, going from 0 to $650 million in sales in year one. Later he became CEO and founder of TrueCar, which went public. At TrueCar, he was the largest individual shareholder and kept buying more stock because he believed in it so much. But they had an earnings miss, the stock dropped dramatically, and he got margin called. He had to borrow money from friends to pay off his margin call.

That same month, he resigned as CEO, got divorced, and his house literally burned down. The following week, he incorporated Fare.com, a new way to buy cars. Fare grew incredibly fast, raised hundreds of millions from Softbank, but eventually crashed.

Now he's back again with Autonomy, which just placed $400 million in orders for Teslas to create a new electric car rental service. He's placed $1 billion in purchase orders across different electric vehicle manufacturers.

He says he's tried 25 things in his career and only 3 have worked, but that's what entrepreneurship looks like - you need 3 to work out of 25 in a 20-year career to be successful."