MoreA Yahoo logo is seen on top of the building where they have offices in New York City, U.S., July 25, 2016.
The tough days of the dot-com bust were a distant memory, and Yahoo Inc, flush with lucrative advertising deals from the world's biggest brands, was enjoying its run as one of the top dogs in the world's hottest industry.
"It was all over the map," recalled Brad Garlinghouse, then a Yahoo senior vice president and now COO of payment settlement start-up Ripple Labs.
Some of the missed opportunities are obvious: a failed bid to buy Facebook Inc for $1 billion in 2006.
Just as damaging as the missed deals, though, was a company culture that ultimately became too bureaucratic and too focused on traditional brand advertising to prosper in a fast-moving tech business, according to some of the former Yahoo managers Reuters spoke with.
Yahoo today has more than 1 billion users and has focused on mobile under chief executive Marissa Mayer, who told Reuters in an interview Monday that she still saw a "path to growth" for Yahoo, which the Verizon merger accelerated.