Chris Sacca invested $25,000 in Twitter before its rise. Why he later said, ‘love the service, hate the stock’

Chris Sacca invested $25000 in Twitter in 2006, when the social media platform was still an early stage service called Twttr. Before the company went public in 2013, Sacca expanded his investment by acquiring privately held shares from former employees and other investors, building a position that made his group Twitter’s largest outside investor, as per a report.

Sacca’s early investment became one of the defining deals of his career as a venture capitalist. But his relationship with Twitter changed after its public listing. By March 2017, he said he no longer owned the company’s stock, even though he continued to like the service.

Chris Sacca invested $25000 in Twitter in 2006

Sacca’s investment began when Evan Williams, who had previously launched the podcasting startup Odeo, decided to develop a microblogging service called Twttr in 2006. Williams asked Sacca whether he wanted to invest.


Sacca wrote a $25,000 check and became an investor, adviser and supporter of the service. He was interested in its potential for revenue and data and regularly encouraged the team as the platform gained attention, as per a Forbes report.

Williams later said Sacca’s enthusiasm helped the team believe in its product. When early celebrity users, including Shaquille O’Neal, attracted attention with their tweets, Sacca sent the team short messages celebrating the platform’s growing reach.

Sacca expanded his Twitter stake before the 2013 IPO

In late 2009, Sacca decided to increase his investment by buying privately held Twitter shares from former employees and other investors. He created four funds to acquire the shares and build a larger position before the company entered the public market.

The effort expanded after Williams approached Sacca about selling $400 million worth of his Twitter shares. Sacca worked with investor Suhail Rizvi to secure commitments of up to $1 billion within 30 days. They spent the following 18 months buying shares from former employees and other investors.

The purchases continued until Twitter’s ownership records closed in May 2013, shortly before its initial public offering. When the extent of the holdings became known, Sacca’s group had accumulated the company’s largest outside-investor position.

$5 billion in returns from Sacca’s Twitter investments

A 2015 Forbes profile estimated Sacca’s personal wealth at $1.2 billion and reported that his various Twitter investments had returned $5 billion to investors.

The $5 billion figure referred to returns across his Twitter deals, not necessarily Sacca’s personal profit. The profile also reported that the value of his first Twitter fund, Lowercase Industry, had increased by about 1,500%.

Sacca’s investment strategy involved backing companies early and building relationships with their founders. His Twitter investment followed that approach, beginning with a relatively small check and expanding through the purchase of privately held shares before the company’s IPO.

Chris Sacca later sold his Twitter shares

By March 2017, Sacca’s view of Twitter as an investment had changed. Responding to questions from his Twitter followers, he said he had not owned the company’s shares for a couple of years and had lost hope when Twitter did not bring back co-founder Evan Williams.

Sacca wrote in a post, “Love the service, hate the stock.”

He later clarified that his fund sold most of its Twitter shares after Jack Dorsey returned as CEO in 2015. Sacca said he personally sold his stake in fall 2016. At the time of the CNBC report, Twitter’s share price had fallen nearly 7% over the previous 12 months.

Sacca called Twitter’s bot problem embarrassing

Sacca also criticized Twitter’s handling of automated accounts, commonly known as bots, describing the problem as embarrassing. He argued that removing bots could hurt the company’s reported user numbers in the short term but would benefit the platform over time.

Research from the University of Southern California and Indiana University cited by a CNBC report estimated that up to 15% of Twitter accounts could be bots. Twitter had reported 319 million monthly active users in 2017, so the estimate could translate to nearly 48 million bot accounts.

Sacca told CNBC in 2017 that, “I would love to see them in a partnership or an acquisition position with a company, just so they would get a little more product vision, maybe freedom to experiment and take some risk, because we just haven’t seen that out of this team.”