Armstrong Puts Another $10 Million In AOL; Huffington Takes Stock

Tim Armstrong, already the largest individual shareholder in AOL (NYSE: AOL) as well as chairman and CEO, nearly doubled his stake in the company following the deal to acquire the Huffington Post. Armstrong believes in having skin in the game — and, as it turns out, so does Arianna Huffington. She told paidContent she will take 25 percent of her payment for HuffPo in AOL stock.

Huffington wouldn’t confirm the amount she is making from the sale, citing the startup’s private status. AOL is paying $315 million for HuffPo, $300 million in cash and $15 million in stock. “I think I’m going to do better than those taking all cash,” Huffington told me. “I’m a complete believer in what we’re going to do so it feels really good.” She added, “I think it’s great to have skin in the game.”

She would not confirm reports that her share of the sale was less than $20 million but her investment in AOL is likely to be in the millions. How much should be clearer when the acquisition is complete since she likely will have to file with the SEC as an insider. Huffington will be president and editor-in-chief of AOL’s Huffington Post Media Group.

It’s a risk. The stock closed at $24.14 Jan. 14, dropped to $23.52 after earnings failed to deliver, took a sharpish slide to $20.59 after the deal went public and started to inch up around the time Armstrong bought his latest lot. It closed at $21.83 Monday.

Armstrong spent just over $10 million last Friday to pick up 477,000 shares at $20.96, according to an SEC filing. That brought his direct holdings to 876,511 shares, worth about $19.1 million at the market’s close. Armstrong also has an indirect interest in 194,857 shares held by his investment group Polar Capital Group, and 514,300 through a family trust. He spent more than $11 million last May in his last major shopping spree.

Armstrong has spoken often about how important it is for him to have an investment. “I wouldn’t do anything with other people’s money that I wouldn’t do on my own,” he told me after AOL’s Feb. 2 earnings call. Four days later, he signed the papers to buy HuffPo.