One of the more interesting parts of the eBay-Skype mega-deal are the investors who hit the jackpot. Everyone knows about Draper Jurvetson Fisher's role given Tim Draper's willingness to talk about the company and his quasi-serious comment at the AlwaysOn conference that Skype was seeking a $1-billion offer. But what about the other investors who managed, for the most part, to stay behind the scenes. Om Malik had a nice post on Danny Rimer, a one-time analyst at Hambrect & Quist, who went on to form Index Ventures with his three brothers and three other partners. Silicon Beat talks about Howard Hartenbaum, a partner with Draper Richards, who along with Bill Draper invested $250K in Skype in 2002 for a 5% stake. (An interesting story on how Hartenbaum stumbled upon Skype can be found here.) The other VCs include Bessemer Venture Partners and Mangrove Capital Partners. There's also speculation Rupert Murdoch also invested in Skype through a private investment firm set up several years ago focused on the digital economy. Some people suggest this is why News Corp. came out of nowhere as a potential buyer for Skype - a move that spawned the idea it was worth $3-billion.
What I'm perhaps most curious about is how much of Skype was handed over to the VCs when the company raised $18.8-million in March 2004? We now know Skype had revenue of $6-million last year, so when the investment was made, the company likely had little or no sales. So what's $18.8-million worth to a company looking to roll out premium based services - a 10% stake, 20%, 30%? Private Equity Weekly reports that Dave Cowan, a general partner with Bessemer, suggested on blog that his firm will see a 150x ROI (I checked out his blog but didn't see the ROI reference so it might have taken take it down). If you take $18.8-million and multiple it by 150, you get $2.8-billion, which would put the VC's  stake at 69%. That strikes me as a big stake but $18.8 million is a lot of money for a company with an unestablished business model. If the VCs received 10% of Skype, they made a 23 times return on their investment ($410-million for $18.8-million); at 20%, it's 46x; at 30%, it's 69x.
Update: Junto Boyz has more insight behind the investment scenes, while Private Equity Weekly has a take on Tim Draper's success, which also includes an investment in Baidu. By the way, I just got around to reading Robert Cringely's take on why eBay made the deal. As usual, he does a nice job poking and prodding the issue before concluding: "I still think is likely to be a mistake in the long run".