8. Jason Calacanis

Category of Candidate: Bloggers and Podcasters

Speculation about Calacanis taking a role at Twitter began shortly after Musk first tendered an offer to purchase the company in the spring. At the time, Calacanis was vaguely involved with the behind-the-scenes efforts to pull together investors who’d throw money into the Twitter deal. Since then, he’s become one of Musk’s most vocal sycophants but the idea of Calacanis being named CEO largely originates with Calacanis himself.

Court documents detailing Musk’s text messages related to the deal were revealed in September and showed Calacanis embarrassingly begging Musk for a chance to run it all. “Put me in the game coach,” he wrote. “Twitter CEO is my dream job.” The Tesla founder has generally seemed cold to this suggestion and on multiple occasions admonished Calacanis for getting too big for his britches.

Calacanis is mostly known for founding Weblogs Inc., an early blogging startup that he sold to AOL in 2005. He was able to take that money and do some angel investing but these days he’s mostly known as the co-host of the All-In Podcast.

I don’t know how successful Calacanis’s investments are but he came up during the times in Silicon Valley when you could offload a company for millions long before anyone figured out what it was really worth. Little is left of the Weblogs Inc. empire today. He doesn’t have much of a record as a businessman.

Take it from me, I just don’t see Musk putting an overrated blogger in charge.