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“Stock lockup” is a term remembered with horror by many entrepreneurs who weren’t allowed to sell their dot com shares before the bubble burst. Bo Peabody founded Tripod, which was sold to Lycos for $58 million in stock. The terms of the sale forced him to hold onto his stock for two years -- while its value happened to increase ten-fold. He also happened to sell his shares just two months before the bubble burst. This lesson in luck was not lost on Bo, who wrote a book titled Lucky or Smart? However, his luck didn’t come out of nowhere. In our interview, he describes the years he spent developing his business even before the Internet was commercially available. He’s now helping entrepreneurs build businesses in parts of the country where venture capitalists typically don’t tread through his venture firm named Village Ventures.

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