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Today’s show:

Some pitches sound just like ads… and it’s a huge red flag for investors.

On our latest edition of TWiST Tokyo, Jason welcomes legendary angel investor (and long-time friend of the pod) Thomas McInerney. His list of investments reads like a Who’s Who of the tech elite, including Notion, SpaceX, Uber, OpenAI, Anthropic, and Perplexity….

At Founder University x Tokyo, they discuss how the angel investing landscape has shifted, why it’s so important for founders to stay humble, the reasons that investors need to stay not just optimistic but aggressively so, and what angels can add to companies beyond just writing checks.

Plus we revisit some classic TWiST clips featuring Thomas from over 10 years ago AND take a look at three of our favorite pitches from our Japanese founders.

Timestamps:

(00:00) FLASHBACK: Clips from Tom’s classic TWiST appearances

(02:54) Why Jason and Tom love hanging and building in Tokyo.

(05:30) How has the angel investing landscape changed over the last decade plus?

(09:38) “Being an investor is a commodity… You have to provide more than just money.”

(12:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(13:34) How Thomas evaluates very early stage startups

(14:56) Why Thomas invested in nuclear tech when it was hugely unpopular

(17:31) Why it’s so important for new founders to be both humble and smart

(18:50) The relevance and accuracy of Marc Andreessen’s “Idea Maze” metaphor

(20:40) Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit http://deel.com/twist to learn more.

(21:41) How Elon Musk brings oversized, visionary ideas to life

(26:11) Why founders using buzzwords is a huge red flag

(27:13) The little “poker tells” Thomas and Jason look for in a founder

(28:26) “If there’s any doubt, there’s no doubt.”

(30:47) LinkedIn Jobs - post your job for free at http://linkedIn.com/twist then promote it to get access to LinkedIn Jobs’ new AI assistant.

(32:04) PRO TIP: Don’t run out of money!

(38:10) The importance of being an aggressive optimist for investors

(43:27) The human brain cannot comprehend 1000x growth

(45:33) PITCH #1: Sakenomist is the cross-border commerce platform, starting with sake exporters (Hiroshi Takeuchi)

(51:47) PITCH #2: HomiiWorld, the IRL social app which helps you meet new people anywhere in the world

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

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Thank you to our partners:

(12:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

(20:40) Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit http://deel.com/twist to learn more.

(30:47) LinkedIn Jobs - post your job for free at http://linkedIn.com/twist then promote it to get access to LinkedIn Jobs’ new AI assistant.

Great TWIST interviews:

Will Guidara

https://youtu.be/pvJa2pzuXWQ

Eoghan McCabe

https://youtu.be/9dHN4YFkgv4

Steve Huffman

https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424

Brian Chesky

https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112

Bob Moesta

https://youtu.be/y2UMzSqX94Q

Episode 2168: The Richie Allen Show Tuesday January 6th 2026

The Richie Allen Show

Reflections on evil and resistance

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