Facebook: Friends with Money

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Facebook has already raised loads of cash. In October, Microsoft invested $240 million in exchange for a 1.6% stake. Then in November and March, Hong Kong billionaire Li Ka-shing wrote two checks for a total of $120 million.

The company will no doubt use much of that financing on its overseas expansion and to broaden its employee base. Today it has 550 employees, but Facebook Chief Operating Officer Sheryl Sandberg says it will probably end the year with 700-800. Many of those workers are engineers who pull in high six-figure incomes.

Yu also says he is planning for a rainy day. "We're trying to put in place a mature capital structure for a growing company," says Yu. The executive has learned from past experience that it's always better to raise money when you don't need it. Yu became chief financial officer of NightFire Software in July, 2000, during a phase when many startups struggled to raise funds. "I tried to raise money during the bust," says Yu. "It was not fun. I will not let that happen to us."

TriplePoint's Biggest Deal

The TriplePoint lease has a degree of flexibility not offered by a traditional loan. For instance, Facebook can exchange or replace equipment during the term of the lease.

TriplePoint, started in July, 2005, by Labe, the former chief of venture leasing pioneer Comdisco Holding, has provided more than $500 million in leases and loans to more than 150 venture-backed companies, including YouTube and Slide.com. It works with startups backed by leading venture capital firms such as Kleiner Perkins Caufield & Byers, Mayfield Fund, and Sequoia Capital.

The deal with Facebook is TriplePoint's largest to date. Previously, it handled a number of transactions in the range of $30 million to $60 million. Recently, TriplePoint financed a $46 million deal with a green energy company backed by Kleiner Perkins that is in stealth mode, Labe says. "The business is on a nice upswing," he says. "The debt financing needs of these companies are increasing."

Ante is the computers department editor for BusinessWeek.