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Twitter's CEO transition has been 'sloppy and confusing,' says investor

Chris Sacca contends investors have been forced to "read the tea leaves" about Twitter's direction.

Twitter investor Chris Sacca is talking about Twitter again -- this time criticizing how the microblogging site is handling CEO Dick Costolo's departure from the company.

Longtime Twitter investor Chris Sacca said the microblogging site is giving mixed messages about its CEO transition. Noah Berger/Bloomberg via Getty Images

Twitter's announcement last week that Costolo will step down July 1 to be replaced by co-founder Jack Dorsey as interim CEO was "sloppy and confusing," he said.

"Investors were left trying to interpret seemingly conflicting accounts and trying to read the tea leaves about where the company was going," Sacca wrote in a blog post Thursday, entitled "What Twitter Says, and What Investors Hear. "Along the way, specific statements about Twitter's future crushed investor hopes and turned what could have been a very positive event for the company into a debilitating mess."

Sacca is among Twitter's earliest and biggest investors.

Sacca's latest salvo comes two weeks after he wrote an 8,500-word blog -- a blueprint of sorts -- that laid out ways the microblogging site could improve. "It needs to place more bets with potentially oversized payoffs," he wrote at the time. "It needs to question aspects of Twitter it has taken for granted. It needs to operate with smaller teams that require less permission to make change happen."

Twitter has had a difficult time satisfying Wall Street since going public in 2013. Analysts say the company has failed to build out new products and lure more users. Sacca said he wrote his latest post after scores of questions and conversations with analysts and reporters. That led him to conclude there's a major disconnect in "what Twitter is saying, what investors are hearing, and what Twitter thinks it is saying."

Costolo and Dorsey's comments that Twitter will not be changing its strategy and direction were "not well-received" by investors, Sacca wrote, saying shareholders "assumed the leadership team was in denial about reality."

Still, Sacca did have a few nice things to say. He called Project Lightning, which puts photos and videos of talked-about events front and center on the site "a bold rethinking of the entire product." Twitter announced Project Lightning on Thursday.

Sacca also continued his praise of Costolo, yet admitted Wall Street considers Twitter management to be "tone-deaf" to their questions. He believes Twitter needs to do a better job talking to investors.

"Let's see if they can get better showing us how all of their moves fit into a cohesive strategy and how Twitter's best days are ahead," he said. "Thoughtful communications will unlock so much value at Twitter and in the price of the company's stock.

"My money says they will get it right."