Jason Calacanis is the host of the All-In Podcast, This Week in Startups, co-founder of the Launch Accelerator, and the “3rd or 4th investor in uber”.

We go inside the origins of All-In, how they decide what to talk about each week, and if Jason thinks it helped swing the election.

We also talk lesson from starting 7 media companies over the past three decades, what he's learned from studying the world's best interviewers, joining Sequoia’s first scout program, his investing strategy at Launch, the story of being the “3rd or 4th investor in Uber", what people underestimate about Elon, and what it was like inside the Twitter buyout in 2022.

Thank you to Austin Petersmith for helping brainstorming topics for the conversation.

Thanks to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠

Timestamps:

(3:34) Interviewing lessons from Oprah, Charlie Rose

(6:48) How to ask good questions

(12:20) Jason’s favorite upcoming podcasters

(17:57) Starting 7 media companies

(22:50) How he'd start a new media company today

(27:56) In-person experiences, “Bang Bang” in Japan

(32:44) Vinyl bars, smartphones, mental health

(38:41) Origin of the All-In Podcast

(42:58) All-In’s influence on the 2024 Election

(46:58) Why All-In got so political

(52:35) Media lessons from Trump

(55:01) Joining Sequoia’s very first scout program

(57:55) Jason’s VC investing strategy

(1:03:55) How Launch competes with other accelerators

(1:08:46) Fundraising is a numbers game

(1:13:06) Investing in Uber and Robinhood Seed rounds

(1:18:31) Origin of “3rd or 4th investor in Uber” meme

(1:20:57) How Jason got the first Model S

(1:26:19) What people underestimate about Elon

(1:27:37) Inside the Twitter takeover

(1:31:44) Career advice for young people

(1:35:22) Jason’s experience taking GLP-1’s

(1:40:05) How All-in picks topics each week

Referenced

Howie: ⁠https://howie.com/⁠

All-In Podcast: ⁠https://allin.com/⁠

Bret Easton Ellis (Podcast): ⁠https://www.breteastonellis.com/podcast⁠

Red Scare (Podcast): ⁠https://en.wikipedia.org/wiki/Red_Scare_(podcast)⁠

Preet Berrara (Podcast): ⁠https://cafe.com/stay-tuned-podcast/⁠

Adam Friedland Show: ⁠https://www.youtube.com/c/TheAdamFriedlandShow⁠

The Insider (Movie): ⁠https://www.imdb.com/title/tt0140352/⁠

Launch: ⁠https://www.launch.co/⁠

Ro: ⁠https://ro.co/⁠

Follow Jason

Twitter: ⁠https://twitter.com/Jason⁠

LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis/⁠

Follow Turner

Twitter: ⁠https://twitter.com/TurnerNovak⁠

LinkedIn: ⁠https://www.linkedin.com/in/turnernovak⁠

Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it