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How a Breakup Led to an Online Marketplace for Used Engagement Rings After getting dumped, one entrepreneur founded I Do Now I Don't, an e-commerce site that turns heartbreak into cold hard cash.

By Michelle Juergen

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Coming home to find your fiancée's diamond engagement ring abandoned on the table doesn't seem like a situation with many upsides. But for Josh Opperman, the end of a romantic relationship left him engaged with something far shinier.

In an effort to move on, the former market researcher decided to sell the ring, expecting to recoup a fair portion of the $10,000 he'd spent.

Instead, retailers offered him, at most, 35 percent of its value. In 2007 a frustrated Opperman founded I Do Now I Don't, an online marketplace for "pre-loved" engagement rings.