rational vc

Cyrus Yari and Iman Olya
rational vc

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. rationalvc.com “In my whole life, I have known no wise people who didn’t read all the time — none, zero. [...] I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than they were when they got up, and boy does that help, particularly when you have a long run ahead of you.” — Charlie Munger

  1. #054 - The Bed of Procrustes: Nassim Taleb (Incerto Series)

    SEP 12

    #054 - The Bed of Procrustes: Nassim Taleb (Incerto Series)

    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 — 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 — 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 — 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

    2h 33m
  2. #053 - Skin in the Game: Nassim Taleb (Incerto Series)

    JUL 25

    #053 - Skin in the Game: Nassim Taleb (Incerto Series)

    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 — 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. — 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

    2h 59m
  3. #052 - Antifragile: Nassim Taleb (Incerto Series)

    JUN 13

    #052 - Antifragile: Nassim Taleb (Incerto Series)

    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

    3h 43m
  4. #051 - The Black Swan: Nassim Taleb (Incerto Series)

    APR 4

    #051 - The Black Swan: Nassim Taleb (Incerto Series)

    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 — 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

    3 hr
  5. #050 - Fooled by Randomness: Nassim Taleb (Incerto Series)

    JAN 8

    #050 - Fooled by Randomness: Nassim Taleb (Incerto Series)

    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

    2h 11m
  6. #048 - Jim O'Shaughnessy (OSV.LLC): Becoming a More Nuanced Thinker

    05/24/2023

    #048 - Jim O'Shaughnessy (OSV.LLC): Becoming a More Nuanced Thinker

    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 - 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  - 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

    1h 11m
  7. #047 - Jonny Blausten: Sprout CEO, democratising venture capital, from consulting to running startups, content creation and future of VC

    05/03/2023

    #047 - Jonny Blausten: Sprout CEO, democratising venture capital, from consulting to running startups, content creation and future of VC

    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 - 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  - 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

    2h 21m

Ratings & Reviews

5
out of 5
3 Ratings

About

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. rationalvc.com “In my whole life, I have known no wise people who didn’t read all the time — none, zero. [...] I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than they were when they got up, and boy does that help, particularly when you have a long run ahead of you.” — Charlie Munger

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