No lack of discussion about MySpace buying PhotoBucket for $300-million ($250-million plus a $50-million earn-out) but one thing that struck me is whether the founders of Flickr, Caterina Fake and Stewart Butterfield, are having yet another round of sellers’ remorse given they sold their photo-sharing company to Yahoo for about $50-million in 2005. Of course, $50-million is nothing to sneeze at, particularly when you’re able to start, operate and sell a company without giving any equity to venture capitalists. Still, there’s an awful lot Fake and Butterfield could have done with an extra $200 very, large ones.

The PhotoBucket vs. Flickr situation does raise an interesting issue for successful entrepreneurs who find themselves the belle of the ball. When the suitors come calling, how do you know when it’s the right time to go home with someone? What kind of questions do you (and your board/advisors) have to ask before accepting a takeover offer? Selling is not only a financial decision but an emotional one. The idea of giving up your baby to someone else after you’ve put so blood, sweat and tear into it is difficult, if not agonizing – especially when there are lots of dollars on the table.

Look at Jonathan Abrams, who built Friendster into a red-hot social networking start-up long before everyone became obsessed with MySpace or Facebook. The story goes that Abrams turned down a $13-million offer from Google before Google did its IPO. If Abrams had accepted the deal, he would have had stock worth significantly more than the $13-million. Another good example is Facebook’s Mark Zuckerman, who has apparently turned a $1-billion offer from Yahoo. Why not take the money and retire to an island in the Caribbean? Maybe Zuckerman thinks Facebook is worth more – and judging by the recent surge in popularity, he may be might. Or maybe Zuckerman’s not ready to give up the most exciting start-up he’ll ever do.

This discussion reminds me of the Kenny Rogers song, “The Gambler”, which includes these lyrics.

You got to know when to hold em, know when to fold em,
Know when to walk away and know when to run.
You never count your money when youre sittin at the table.
Therell be time enough for countin when the dealins done.

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