View from Washington: Why Jason Calacanis could be Mark Zuckerberg’s nemesis

“You have no idea what you’re doing when it comes to privacy. You have a lack of leadership when it comes to privacy. And you have a glib and reckless approach to people’s privacy. You are a brilliant engineer who is creating a level of mistrust with his users that is unprecedented and obnoxious.”

Jason Calacanis, ‘Open message to Mark Zuckerberg’, YouTube, December 2009.

Back in Blighty, chances are that entrepreneur Jason Calacanis is an unfamiliar name. In the US, he is a high-profile angel investor (backing Uber in its early days) and a frequent media presence across blogs, podcasts, interviews and conferences. A former general manager of Netscape, he sold his Weblogs venture to AOL for an estimated $25m at the height of the noughties’ dot.com frenzy and published two of the market’s leading journals.

He is also a long-standing critic of Facebook chairman and CEO Mark Zuckerberg. See above – and check the date.

Seizing on the latest wave of controversy surrounding Zuck and his ‘platform’, Calacanis yesterday (April 24) launched the ‘Openbook Challenge’. It is a competition from which Calacanis intends to select seven potential alternatives to Facebook. He will give each $100,000 in seed funding in exchange for 6 per cent of the winners’ equity. The deadline is June 15.

Just how much of a chance will these companies have? Calacanis himself acknowledges that success will be hard to achieve. In an interview with The Guardian – the newspaper to which Zuckerberg will not talk – he cited the “unprecedented moat” Facebook has filled with data both from its own operations and by either acquiring (Instagram, WhatsApp) or copying (Snapchat) competitors.

However, Calacanis’s blog also reiterates his faith in the disruptive evolution of the web economy.

“All community and social products on the internet have had their era, from AOL to MySpace, and typically they’re not shut down by the government — they’re slowly replaced by better products,” he writes. “So, let’s start the process of replacing Facebook.”

It is an interesting idea, and you can read more about what Calacanis sees as the fundamental tenets of a functional social network on his blog (the main points are at the bottom here also). But I’d argue the Openbook Challenge is not in and of itself what makes him potentially Zuckerberg’s nemesis.

Not just in his Facebook criticisms but throughout his public statements, Calacanis has consistently stressed that successful companies and founders share one key attribute, “the ability to execute”. It doesn’t matter so much that one pitch has a better idea than another; the one that deserves investment is that which best shows how it will make its idea happen.

That “ability to execute” is Facebook’s and, personally, Zuckerberg’s Achilles’ heel. For privacy, the company has repeatedly overpromised and underdelivered. The same can be said for its approach to rogue content and online bullying.

By launching the Openbook Challenge and by reiterating the importance of execution as his overwhelming criterion for choosing its winners, Calacanis will put Facebook’s executive shortcomings back in the spotlight. As noted earlier, the entrepreneur has built himself a large bully pulpit from which to proffer his observations and disperse his wealth.

Moreover, he is no longer alone in thinking that Facebook’s management is falling short and that the company's problems are having a knock-on effect across high technology.

Respected British commentator Felix Salmon made the case for Zuckerberg’s resignation earlier this month in Wired. Then, there were the recent and very public putdowns Zuckerberg received from Apple CEO Tim Cook and Tesla & Space X CEO Elon Musk (the latter even shutting down his companies’ Facebook pages). As you might suspect, those point to a wider Silicon Valley frustration with Zuckerberg and his team. This now goes far beyond the commentariat and a few 'outliers'.

Zuckerberg’s appearances before US politicians were more savvy than many had expected – he probably has done enough to draw Capitol Hill’s sting for the time being. But as Calacanis’s move shows, it may be the friendly fire he should now worry about. Particularly when more of it is coming from those we can credit with some idea of how a big tech company should – and should not – be run.

Jason Calacanis’ five attributes for a social network that serves society

1. Respect and protect consumer’s privacy.
2. Respect and protect our democracy from bad actors.
3. Respect and protect the truth, by stopping the spread of misinformation.
4. Not try and manipulate people by making them addicted to the service.
5. Protect freedom of speech, while curbing abuse (not easy!)