Placing a Bet On Someone

BusinessInsider, the sometimes good reporting site which has become more dominated by cheesy sales pitches, still has some good in-depth reporting once in a while.

Two of their more "veteran" (if one can use that term on such a young site) reporters did an in-depth piece on the history of Twitter, or how it got from there to here. To their credit, the reporters resist the urge to idolize or simplify the process of a successful startup. They explore the trials, travails, uncertainty, and, in their own word, "chaos" that prevailed throughout many important periods in Twitter's history.

One of the pivotal moments was the firing of Evan Williams and his pushing for then-COO Dick Costolo to take over. The Board had considered Costolo, but was reluctant. He was "old" by Silicon Valley standards and had never run a company larger than one third of Twitter's size - and Twitter was growing very rapidly. In the end, the Board took the plunge, and Costolo succeeded, bringing Twitter all the way to its imminent IPO of 15 November 2013.

It is ironic that the Board was averse to hiring someone without sufficient paper experience, despite demonstrated skill and talent. The Board of a risky startup was acting in a highly conservative manner, hiring as if it were an executive at GE or JPMC, not Twitter.

Most people look at the risk of doing something; it is in their nature to ask, "what if I fail?" Entrepreneurs balance the risk of not doing something; they are far more concerned that they are passing up an opportunity hat will not recur.

Given that the Board of Twitter was composed of investors and founders of a venture that by definition had only gotten that far by employees, founders and investors saying, "what if we don't join," it is ironic that they asked, "what if Costolo cannot handle it? He has never done it before!"

It is not so surprising, then, that Williams, the entrepreneur, was the one who could balance the risks and push for the talented but less experienced choice. "What if we don't take him?"