There’s no one more perfectly situated between the tech media and the tech elites who loathe them.
Jason Calacanis built his reputation in Silicon Valley as a feisty tech reporter, waiting in line to ask Steve Jobs questions at the Code Conference. An extremely early investment in Uber suddenly made him one of the most famous angel investors in the world (thanks also to Calacanis’s self-promotional megaphone). Today, Calacanis co-hosts All-In, the second-most popular tech podcast and one of the most popular podcasts in the world. The show is a must-listen in Silicon Valley and the envy of many wannabe thought leaders.
We invited Calacanis on our much, much smaller tech podcast Dead Cat to interrogate what has made All-In so successful and where Silicon Valley’s roiling war with the media is headed. Calacanis, who is reportedly part of Elon Musk’s war room at Twitter, warned us that he absolutely would not talk about Musk’s Twitter. (We tried.)
This was a fun episode that we recorded right before Thanksgiving with co-host Tom Dotan and regular special guest Katie Benner. I’m going to publish a companion article with my reflections on the conversation shortly. Enjoy!