In April, Mark Zuckerberg's Facebook agreed a deal to buy instagram, the new hot property on the social media block, in a deal worth at the time around $1 billion.
However, Facebook announced that Instagram would only receive $300 million in cash and the rest of the figure would be made up of around 23 million shares in Facebook once the deal closed.
Facebook shares at the time, which was before the company floated on the US stock market, were valued by the parties at around $30.
Instagram looked to have scored a great deal when Facebook shares started trading in mid-May at $38, as this meant that the deal value increased to around $1.2bn.
But that turned sour after Facebook saw a dramatic slide in its stock price to around $20, as investors became concerned over the firm's long-term revenue prospects.
This meant that the Instagram acquisition is now valued at around $735m and the company's founders Kevin Systrom and Mike Krieger are out of pocket by the tune of around $300m - on paper at least.
The New York Times notes that Instagram came unstuck in the way it negotiated the deal, as the firm did not agree a fixed value for the stock at the time of the acquisition.
Rather than demanding a fixed dollar value for the shares, the company instead opted for a fixed number of shares, meaning its owners took the risk of a decline in Facebook's value in order to benefit from increase, which to be fair was initially expected.
Facebook recently secured regulatory approval for the Instagram deal from British authorities, but is still awaiting approval from US regulators.
Recent reports have implied that Facebook is trying to speed up the review in order to close the transaction. This is particularly because it must pay Instagram $200m if the deal hits the regulatory buffers.