By Erin Mendell
IT’S ALWAYS THE INVESTMENTS that you don’t make that stick out. And so it was for Maynard Webb, the board chairman of Yahoo and former eBay executive.
He’s made millions from his successful tech investments, but he still regrets not investing more in Salesforce.com, a software start-up that began in 1999. Webb was on the company board (whose members could sell shares six months after the IPO) and saw potential when the stock market crashed in 2008 and Salesforce’s shares fell below $6. He figured investors had overreacted because the company was already the industry leader. To him, it was an “investment homerun.”
He was right, and Salesforce has since surged in value and undergone a four-for-one stock split, with shares topping $55 in 2014. The only problem: Webb heeded the advice from his risk-wary financial advisers and invested just half the amount that he had initially planned. They argued—wrongly—that he might lose big by putting too much of his money in one asset. “Financial folks are geared to protect your downside,” says Webb. But he learned his lesson: “Sometimes, the things that will make you the most require more risk than most people would be willing to take.”