Outspoken, smart, controversial, driven and, ultimately, extremely successful - Jason Calacanis has been a fixture in the startup and digital worlds for over two decades.
The creator of the LAUNCH conference, Inside newsletter platform and This Week In Startups (TWiSt) podcast, Calacanis is perhaps best known as angel investor in new businesses.
His biggest punt in travel, mostly famously, came with his backing of the nascent ride-hailing service Uber in 2007.
In the annual "Breaking Brad" session at The Phocuswright Conference, Calacanis joined Altimeter Capital CEO and founder Brad Gerstner for a frank and fast-paced discussion, covering subjects ranging from the industry and government responses to the pandemic to startup investing and what to watch out for as the sector and society recover.
Inevitably, Calacanis has a bunch of stories to tell about the tight-knit world of fellow investors who have hit the big time - but not without hiccups along the way, in the case of SpaceX and Tesla supremo Elon Musk.
Gerstner's previous guests included Bill Gurley (Benchmark Capital) and Chamath Palihapitiya (Social Capital and Virgin Galactic).
Check the full interview with Calacanis below...
Breaking Brad Episode 3 - Brad Gerstner & Jason Calacanis - The Phocuswright Conference Online 2020