Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick, Investing in 100+ Startups per Year with Jason Calacanis
The Peel with Turner Novak
Turner Novak
4.6 • 11 Ratings
🗓️ 18 December 2025
⏱️ 103 minutes
🧾️ Download transcript
Summary
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
Transcript
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| 0:00.0 | Welcome to the Peel. I'm your host, Turner Novak, founder of Banana Capital. |
| 0:07.0 | Today's guest is Jason Calcanus. Jason is known for being the host of the All-On podcast. |
| 0:12.0 | We go inside the origins of the show, how they decide what to talk about each week, and if Jason thinks it helped swing the election. |
| 0:18.0 | We also talk Jason's early days, lessons from starting seven media companies over three |
| 0:22.2 | decades, why he studies the best interviewers, joining Sequoia's first Skelp program, his |
| 0:27.1 | investing strategy and launch in Founder University, the story of being the third or fourth investor |
| 0:32.4 | in Uber, and I say out the quotes if you're not watching the video, what people underestimate |
| 0:37.2 | about Elon and what it was like inside the Twitter buyout in 2022. |
| 0:41.9 | A quick thank you to our friend Austin Peter Smith at Howie for helping brainstorm topics for Jason. |
| 0:46.7 | A reminder, I publish two episodes of The Peel every week exploring the world's greatest startup stories just like this one. |
| 0:52.8 | Check with the backadlog of over 100 episodes and tune to next week for Marcelo Libre, co-founder of |
| 0:59.1 | Global Payroll and H.R.juggernaut remote.com. Now let's talk to Jason after a quick word |
| 1:04.9 | from Numerle. This episode is brought to you by Numeril. Numeril is the fastest, easiest way to stay compliant with U.S. sales tax and global VAT. |
| 1:13.9 | It's easy to set up and they automatically handle all registrations, ongoing filings, |
| 1:18.7 | and their API provides sales tax rates wherever you need them with all the integrations you need. |
| 1:23.7 | Numeril supports over 2,000 customers in both the U.S. and globally, |
| 1:27.2 | and they pride themselves on White Glove, high-touch customer service. Plus, they guarantee their work, and they'll cover the difference if they mess anything up. They're fresh off of fundraise, closing a $35 million Series B from Mayfield, which they're going to reinvest into building an even better product. If you want to put your sales tax on autopilot, check out Numeril at their new domain, |
| 1:46.0 | numeral.com. |
| 1:48.0 | That's N-U-M-E-R-A-L.com, |
| 1:51.0 | for the end-to-end platform for sales tax |
| 1:54.0 | and VAT compliance. |
| 1:58.0 | Jason, welcome to the show. |
... |
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