Twitter's IPO CEO Was A Comedian

Oct.31.13 | About: Twitter, Inc. (TWTR)

Who is Dick Costolo?

Twitter (NYSE:TWTR) is getting ready to launch an IPO and spearheading this effort is CEO, Dick Costolo, who is planning on doing some media tours to highlight the offering. This is expected to be the largest IPO in history and will be kicked off by a multiple city road show with prospective investors in the affluent city of Boston.

A Joker's Persona

As a chief executive, Costolo is best known for two things: his fascination with one-liners, delivered through frequent tweets and during interviews with the press; and his dry wit and flippancy, a legacy from his former career as a stand-up comedian.

While his witticisms are disarming, charming, and frivolous, as well as occasionally acerbic, Costolo is anything but a fool. It's only a role he plays with considerable finesse with his knack for banter, which is often highlighted in press coverage. He's somewhat like the court jester in medieval kingdoms celebrated in Shakespearean literature--someone who entertains the king and the court with slapstick humor but actually has a keen understanding of what's going on. Similarly, behind Costolo's witticisms is an astute mind, someone who thoroughly analyzes every move he makes, much like a chess master, before making it.

An example of his analytic prowess is this current initiative to grow Twitter's value. Since he owns 1.6% of Twitter, it is estimated by industry analysts that after the IPO he will be worth hundreds of millions of dollars.

Another example of his shrewdness is his track record at Twitter. He became CEO in 2010, and at that time Twitter was valued in the millions. Now, his next move with the IPO is to sell 70 to 80 million shares at $17 to $20 to the public, which will place the company at a value of $10.9 billion.

A Tough Cookie: Surviving Twitter's Mood Swings

A new book by New York Times journalist Nick Bilton "Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal," reveals yet another side to Costolo. The book will be released on November 5th, but some of its content has been revealed in interviews with leading publications like USA Today.

Like the mild-mannered reporter, Clark Kent, who is really a man of steel, Costello, too, is much more resilient and steel-like than he appears to be. The following story reveals this other side of him that is not often covered in press reports.

Back in 2010, Twitters co-founder Jack Dorsey was unhappy with the performance of Evan Williams, the CEO at the time. Consequently, he convened a board meeting to find a new candidate. Bill Campbell, a board adviser, suggested that Costello, the COO at the time, should be fired as this would make it much easier to find a new CEO candidate. According to this story, which Twitter denies to this day, Campbell walked into Costolo's office and proceeded to unceremoniously fire him. However, once Costolo realized that it was not a prank, he did not meekly capitulate and settle for a handsome severance pay, something that a high percentage of high level executives in his position would have done, but challenged this dismissal. As history proves, not only did he keep his job, he then ran the company that had wanted to get rid of him.


Although Costolo appears to be fond of banter and making off-hand comments to stir up controversy, he is a very perceptive man, and although he appears to be a mild-mannered person, his own career history has showed that he is capable of making the tough decisions even when the company he is working for turns against him. In many ways, then, he appears to be other than the way he presents himself to the general public. It's not that he intends to deceive; he is just a man with more to him than the eye can see and the flurry of press reports reveal.

In the final analysis, he is the right man for the job. In the current IPO hullabaloo, he is acting according to character: after carefully studying the mistakes made by Facebook (NASDAQ:FB) before its famous IPO, he promises that Twitter will do it right. This is good news for those investing in his insights

Disclosure: I have no positions in any stocks mentioned, and no plans to initiate any positions within the next 72 hours. I wrote this article myself, and it expresses my own opinions. I am not receiving compensation for it (other than from Seeking Alpha). I have no business relationship with any company whose stock is mentioned in this article.