Big question, and lots of interesting solutions. I’ve been out of the news loop the past couple of days, but this eBay/Skype story was hard to miss. Without rehashing the mainstream headlines, it’s clearly on the table now that eBay has given up trying to create synergies with Skype, so the focus now is on making the best of things as distinct entities.

The preferred route for eBay would be to keep Skype and recoup their investment via an IPO sometime next year. That would certainly bring an end to things with both parties leaving on a high note. Of course this hinges heavily on the state of capital markets, and the optimist would say that by next year we’ll be so fed up with the recession, investors will happily jump into anything resembling a good news story. Skype IS a good news story, and no doubt Wall Street would play this up as the IPO that kick starts tech stocks back to life. If so, Skype could ride this wave a while by validating this space for investors and giving us all a reason to believe that tech stocks can make us wealthy again.

And what do I mean by “this space” anyway? To me, this is where things get interesting. Most people associate Skype with VoIP and PC telephony, and we all know how poorly that “space” has done for investors lately. Don’t forget Vonage got first mover advantage by going public ahead of Skype, and contrary to great expectations, their IPO set VoIP back a very long way with investors. I like Skype’s prospects a lot more than Vonage, so for those looking for a second chance at the VoIP space, a Skype IPO would be ideal.

However, I see Skype being much more than a VoIP play. I won’t deny that’s important, but to me Skype is really a Web 2.0 story. Their revenues are built almost entirely around VoIP, but there’s so much more potential if/when they can monetize their community of over 400 million users—video, mobile apps, social networking, file sharing, business users, etc. Of course that’s a big IF, but think about what that would mean for all those Web 2.0 companies out there with huge communities but no real business models—Myspace, Facebook, Twitter, Flickr, etc. If Skype can show the way, then I could see their IPO being much bigger, not just financially, but providing some validity to invest in all these other stories, which then makes Web 2.0 the next BIG THING.

I’m guessing that’s why Niklas and Janus want to buy Skype back. It has to be a good sign when the founders want back in, and they certainly aren’t hurting for cash. Joost was their follow up to Skype, and it really hasn’t done much—but probably could with Skype back in the picture. Talk about interesting possibilities. Of course, there’s another big twist here—Joltid—which appears to be the core technology Skype was built upon. It’s a mystery to me why this didn’t come with the Skype acquisition—and I’m guessing the Skype folks felt it was too important, and maybe that’s turning out to be true now. So, a lot depends on how this plays out, and who will end up with lawful control. I’d have to say all bets are off until this is resolved. If Joltid ends up with eBay, Skype may not be as attractive to the founders, and vice versa should it go the other way.

And then there’s the scenario of Skype being acquired by one of the usual suspects—Google, Microsoft, Yahoo. There’s a storyline around all these, but for my money, I’ve long felt Apple would be the best fit, or possibly a Web-savvy company like Adobe. I got to share that view with the BBC yesterday, which was nice, but we’ll need a longer conversation to take this further. Back to work…