Learn from history's Greatest Minds — and find Timeless ideas you can apply to business and life. Every episode we explore a Lindy book: We strive to become polymaths like our investing and business icons, pulling the Big Ideas from a wide range of disciplines. For the curious-minded seeking Worldly Wisdom. Join 3,000+ others by subscribing @ rationalvc.com to get free access to essays and exclusive content.

For the video version of this episode click here.

A rare episode where we invited guests to join us, in this case due to the book being a unique format and also wrapping up our entire 5-episode Incerto Series. We discussed the application of the Incerto teachings in the real world, with two of the biggest Incerto practitioners we know.

Timestamps:

(00:00) Intro

(08:57) Our Favourite Aphorisms

(16:04) Special Guests Join & Their Intros

(17:59) Dangers of Monthly Salary

(24:25) Golden Handcuffs, Legacy vs. Lifestyle

(28:00) Our DNA as Hunter-Gatherers

(31:50) Learn Sales Before Technical Skills

(36:00) Practice Before Theory

(37:04) Conventional Education

(43:00) Convexity, Agency, & Mediocristan

(57:21) More Aphorisms

(1:00:19) Ergodicity, Rationality & Survival

(1:08:32) Venture Capital & Startups

(1:23:53) Asymmetry of Information, & Honour

(1:29:20) Bureaucracy

(1:34:05) Fat Tony

(1:43:11) Small Bets

(2:09:51) Via Negativa & Making Money Online

(2:18:19) Gathering Vs. Elicitation Mindset

(2:21:52) Incerto Practice in the Real World

(2:31:06) Closing Thoughts

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Our website (all essays and podcasts): rationalvc.com
Our investment fund: rational.fund
Cyrus' Twitter: x.com/CyrusYari
Iman's Twitter: x.com/iman_olya

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Guests:

Daniel Vassallo's Twitter: x.com/dvassallo
Seb Lees' Twitter: x.com/sebs_tweets
Daniel's company: smallbets.com
Seb's Podcast & Community: fattonys.net

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Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s).

#Timeless #wisdom #knowledge #books #polymaths

Learn from history's Greatest Minds — and find Timeless ideas you can apply to business and life. Every episode we explore a Lindy book: We strive to become polymaths like our investing and business icons, pulling the Big Ideas from a wide range of disciplines to help us become better investors and operators. For the curious-minded seeking Worldly Wisdom. Join 3,000+ others by subscribing @ rationalvc.com to get free access to essays and exclusive content.

For the video version of this episode click here.

Timestamps:

(00:00) Intro

(08:16) Core Concepts

(12:10) Important Prologue One

(29:10) Important Prologue Two

(45:04) Prologue Three

(49:42) A First Look at Agency

(1:05:00) Ethics Problems in Scaling

(1:09:00) The Minority Rule

(1:29:40) Employment & FU Money, Freedom

(1:47:26) Status, Manners & Competence

(1:49:55) On Taking Risks

(1:55:35) The Intellectual Yet Idiot

(2:04:17) The Lindy Effect Recap

(2:09:10) Deeper Into Agency

(2:11:58) The Illusion of Business Plans

(2:15:00) Charlie Munger, Show Rather Than Be

(2:17:15) Financial Minimalism, Mimesis

(2:24:22) Virtues & Advice for Young People

(2:26:37) The Interventionistas

(2:28:36) Religion, Belief, & SITG

(2:31:10) Most Important, Book 8: Risk & Rationality

(2:51:05) Epilogue

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Our website (all essays and podcasts): rationalvc.com
Our investment fund: rational.fund
Cyrus' Twitter: x.com/CyrusYari
Iman's Twitter: x.com/iman_olya

—

Referenced Material:

Cyrus on "Financial Minimalism", Viral Essay:
https://www.rationalvc.com/articles/minimalism

Also listen to the prior three podcast episodes - each covered the other books of Taleb's Incerto Series.

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Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s).

#Timeless #wisdom #knowledge #books #polymaths

Learn from history's Greatest Minds — and find Timeless ideas you can apply to business and life. Every episode we explore a Lindy book: We strive to become polymaths like our investing and business icons, pulling the Big Ideas from a wide range of disciplines to help us become better investors and operators. For the curious-minded seeking Worldly Wisdom. Join 3,000+ others by subscribing @ rationalvc.com to get free access to essays and exclusive content.

For the video version of this episode click here.

Timestamps:

(00:00) Intro

(11:39) Antifragile definition

(19:13) Introduction to the core concepts

(22:04) Hormesis, naïve interventionism, iatrogenics

(33:55) Peter Kaufmann and Charlie Munger

(35:57) Modernity, Switzerland, political systems

(55:21) Concavity vs Convexity and Black Swans

(1:07:30) FU Money and wealth

(1:13:12) Optionality and wealth

(1:21:47) Barbell strategy

(1:43:02) Rational Flaneur

(1:47:23) The Lindy Effect

(2:01:22) Raising antifragile kids

(2:12:19) Green Lumbar fallacy

(2:23:53) Signal vs Noise

(2:29:00) Via Negativa

(2:51:07) Ethics of Antifragility and Skin in the Game

(2:57:36) Deep dives and quotes

(3:35:32) Closing thoughts

—

Our website (all essays and podcasts): rationalvc.com
Our investment fund: rational.fund
Cyrus' Twitter: x.com/CyrusYari
Iman's Twitter: x.com/iman_olya

—

Links mentioned in the episode:

Cyrus referenced Tweets:
https://x.com/CyrusYari/status/1792279103862681603
https://x.com/CyrusYari/status/1757715505819906419
https://x.com/CyrusYari/status/1679174178195353600

Peter Kauffman Rational VC episode:
https://www.youtube.com/watch?v=kMiOFC07X8M&t=8s

The Black Swan episode:
https://youtu.be/HVGJQ25Cr2k?si=8b2DPBPX80Pgbgag

Vizi Andrei:
https://twitter.com/viziandrei

Daniel Vassallo:
https://twitter.com/dvassallo

Cyrus essay on Angel Investing (incl. Barbell Investing):
https://www.rationalvc.com/articles/angel

WhosAria Bars of Wisdom newsletter:
https://www.barsofwisdom.com

Fat Tony's Community:
https://fattonys.net/

—

Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s).

#Timeless #wisdom #knowledge #books #polymaths

Learn from history's Greatest Minds — and find Timeless ideas you can apply to business and life. Every podcast episode we explore a Lindy book: We strive to become polymaths like our investing and business icons, pulling the Big Ideas from a wide range of disciplines to help us become better investors and operators. For the curious-minded seeking Worldly Wisdom. Join 3,000+ curious minds and avid readers by subscribing @ rationalvc.com to get free access to essays and exclusive content.

For the video version of this episode click here.

Timestamps:

(00:00) Intro / chit-chat

(09:26) Structure of the show

(10:36) What is a Black Swan?

(19:34) Human blindness to Black Swans

(01:02:45) Mediocristan vs Extremistan

(01:30:45) Bell Curve / Gaussian fraud

(01:37:18) Why the Midwit meme is wrong

(01:47:27) Leveraging Black Swans

(01:58:34) Chapter overviews

(02:19:16) Chapter 19 deep dive

(02:27:58) Favourite quotes / our lives

(02:37:09) Fat Tony

(02:43:33) 10 Principles for Black Swan robustness

(02:48:54) Amor Fati

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Our website (all essays and podcasts): rationalvc.com
Our investment fund: rational.fund
Cyrus' Twitter: x.com/CyrusYari
Iman's Twitter: x.com/iman_olya

—

Links mentioned in the episode below:

Iman Tweet on daily routines of creatives:
https://twitter.com/iman_olya/status/1764721995743121415

Table 1 - Extremistan vs Mediocristan:
https://capitalideasonline.com/wordpress/mediocristan-vs-extremistan/

Vizi Andrei:
https://twitter.com/viziandrei

Cyrus being interviewed on the Brick by Brick podcast:
https://open.spotify.com/episode/54RvagfMSIWNtVwAe2193a?si=1cb28db259814326

Cyrus essay on Angel Investing (incl. Barbell Investing):
https://www.rationalvc.com/articles/angel

Cyrus essay on Tech Markets are Irrational:
https://www.rationalvc.com/articles/irrational

Jack Raines FU Money ZeroHedge essay:
https://www.youngmoney.co/p/fck-money

WhosAria Bars of Wisdom newsletter:
https://www.barsofwisdom.com

Fat Tony's Community:
https://fattonys.net/

—

Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s).

#Timeless #wisdom #knowledge #books #polymaths

Learn from history's Greatest Minds — and find Timeless ideas you can apply to business and life. Every episode we explore a Lindy book: We strive to become polymaths like our investing and business icons, pulling the Big Ideas from a wide range of disciplines to help us become better investors and operators. For the curious-minded seeking Worldly Wisdom. Join 3,000+ others by subscribing @ rationalvc.com to get free access to essays and exclusive content.

For the video version of this episode click here.

Timestamps:

(00:00) Intro / chit-chat

(20:11) Randomness & Luck

(24:46) Monte Carlo Simulation

(31:09) Ergodicity

(31:39) Hindsight Bias

(38:00) Survivorship Bias

(39:50) Asymmetric Bets / John & Nero

(49:53) Skewness & Asymmetry

(57:19) Pascal's Wager

(1:00:53) Induction & Chaos Theory

(1:03:22) Chapter 11

(1:08:45) System-1 vs System-2 Thinking

(1:10:03) Satisficing

(1:20:08) Normative vs Positive Thinking

(1:25:52) Signal vs Noise

(1:28:20) Heuristics

(1:33:45) Final Part of Book (Part 3's Importance)

(1:44:41) Favourite Quotes / Our Lives

(2:06:11) Final Thoughts

—

Our website (all essays and podcasts): rationalvc.com
Our investment fund: rational.fund
Cyrus' Twitter: x.com/CyrusYari
Iman's Twitter: x.com/iman_olya

—

Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s).

#Lindy #knowledge #books

** Apologies for the audio quality, it's been a while! New audio set-up. The audio will be significantly better from the next episode. In this transitionary episode we discuss our pivot, after 49 episodes our podcast is continuing, albeit in a much different direction, and rebranding. From the next episode (ep. 50 it will be in the new format and all changes will be reflected then). We discuss all the changes (and our view on the podcasting space) in this short transitionary episode.

Video version of episode: https://www.youtube.com/watch?v=x2L49pYXx8g 

"the rational letter" - For free you can join 3,000+ seasoned investors, founders, scientists, engineers, and erudites read the same email summary of our learnings from a Lindy book and use the ideas in their work and life. Curated and emailed once a month. Nothing else. Sign up for it here: https://rationalvc.com

 
Our investment fund: https://rational.fund 
Cyrus' Twitter: https://twitter.com/CyrusYari 
Iman's Twitter: https://twitter.com/iman_olya 

00:00 Intro Banter
04:18 Explaining the Pivot / Rebrand, Plus Views on Podcasting Space
26:07 Outro

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Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s).

#podcast #knowledge #books

Jim O'Shaughnessy is one of the greatest thinkers of our time. A curious mind, Wall Street legend, Venture Capitalist (OSV.llc), best-selling author, previously founder of OSAM (sold to Franklin Templeton), podcaster (infinite loops), father, grandfather, and the list goes on. We discussed numerous topics. Check the timestamps below for topics and enjoy the audio, or you can watch the video over on our YouTube channel: https://youtu.be/W-t1v-u-iAg 

Jim's Twitter: https://twitter.com/jposhaughnessy  O'Shaughnessy Ventures: https://www.osv.llc 
Jim's Podcast: https://open.spotify.com/show/7yAAsaj77q3jQLbX8NAQ7J?si=950606434743485f 

00:00 Teaser
01:05 Intro
03:30 The Great Reshuffle / investment in Odin
11:01 O'Shaughnessy Ventures
19:53 What Jim looks for in startups
26:21 Autonomy and accountability in portfolio companies
33:37 Psychological biases & improving decision-making
40:20 Meme culture and human nature
53:07 Wealth creation
1:04:25 What's driving Jim?
1:08:47 Message from Jim

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Get in touch with us:

Our website (all essays and podcasts): https://rationalvc.com 
Our investment fund: https://rational.fund 
Cyrus' Twitter: https://twitter.com/CyrusYari 
Iman's Twitter: https://twitter.com/iman_olya 

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Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s). No copyright infringement intended.

#venturecapital #investing #startup

Jonny is the CEO and Co-Founder of Sprout: an investment platform curating access to Venture Capital deals for private investors. We discussed numerous topics. Check the timestamps below for topics and enjoy the audio, or you can watch the video over on our YouTube channel:
https://youtu.be/wXWu552WyVE

Jonny's LinkedIn: https://www.linkedin.com/in/jonathan-blausten-b5178141/?originalSubdomain=uk
Jonny's personal Twitter: https://twitter.com/JBlausten
Jonny's GunnerPunner Twitter: https://twitter.com/gunnerpunner
Sprout website: https://www.viasprout.com/

00:00 Teaser
01:18 Intros
04:19 Jonny's background
05:50 Jonny's early startups
12:32 Jonny's parents & real estate
16:02 Corporate life is charlatanism?
33:26 Sprout intro
36:39 Sprout in depth - the problem of access to the best deals
44:33 Sprout's vision and competition
48:37 UK vs US investors
52:06 Sprout community & education
57:42 VC fund access for retail investors
1:03:13 Sprout's 10 T's (assessing VC funds)
1:10:13 Why do VC funds fail and biases
1:17:19 Sprout's monetisation 
1:20:52 Future for Sprout
1:25:25 Why is VC hard?
1:28:50 VCs are charlatans?
1:33:50 VC fund skillset diversification
1:45:24 Future of VC & solo GPs
1:54:35 Content creation & side hustles
2:06:48 Jonny's values & principles 
2:15:22 Ending thoughts

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Get in touch with us:

Our website (all essays and podcasts): https://rationalvc.com 
Our investment fund: https://rational.fund 
Cyrus' Twitter: https://twitter.com/CyrusYari 
Iman's Twitter: https://twitter.com/iman_olya 

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Disclaimer: The materials provided are solely for informational or entertainment purposes and do not constitute investment or legal advice. All opinions expressed by hosts and guests are solely their own opinions and do not reflect the opinion of their employer(s). No copyright infringement intended.

#sprout #JonnyBlausten #VentureCapital