rational vc

Hosted by Cyrus Yari and Iman Olya

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Jan 2025

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January 1, 20252 hr 52 min

#055 - Poor Charlie's Almanack: The Essential Wit and Wisdom of Charles T. Munger

Learn from history's Greatest Minds — and find Timeless ideas you can apply to business and life. Every podcast episode we explore a Timeless 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 thousands of readers by subscribing @ rationalvc.com to get free access to essays and exclusive content. For the video version of this episode click here. Free digital version of Poor Charlie's Almanack: stripe.press/poor-charlies-almanack Timestamps: (00:00) Intro chit chat (11:26) Foreword (16:20) Introduction by Kaufman (21:00) Munger's childhood and family (31:48) Munger and Buffett meet (34:45) Munger's kids tales (37:59) Munger's discipline (51:34) Mental models (1:01:39) Investing checklist (1:07:30) Eleven Talks intro (1:09:16) Talk One (1:17:12) Social proof (1:24:45) Circle of competence (1:35:00) Talk Two Advice (1:38:55) Talk Three (1:40:50) Ideology (1:42:42) Talk Three Q&A (1:49:00) Talk Four - Coca Cola Case (2:01:45) Talk Nine - Economics (2:05:20) Talk Ten - Perseverance (2:13:21) Talk Eleven Intro (2:16:09) Important: 25 Biases and Tendencies (2:49:06) Outro — Our website (all essays and podcasts): rationalvc.com Our investment fund: rational.fund Our Discord: discord.gg/JZbqu3Cjjn Cyrus' Twitter: twitter.com/CyrusYari Iman's Twitter: 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). #Timeless #wisdom #knowledge #books #polymaths

September 12, 20242 hr 33 min

#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

July 25, 20242 hr 58 min

#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

June 13, 20243 hr 42 min

#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

April 4, 20243 hr 0 min

#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

January 8, 20242 hr 11 min

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

August 29, 202326 min

#049 - The Podcast Is Pivoting And Rebranding!

** 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 - 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

May 24, 20231 hr 10 min

#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

May 3, 20232 hr 21 min

#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

March 22, 20231 hr 8 min

#046 - Ben Awad: Becoming the Internet's Most Impactful Programmer

Ben Awad is a YouTuber, software engineer, and the founder of VoidPet.com. He has 500k YouTube subscribers, 800k TikTok followers, and is known for his legendary coding tutorials and humorous and authentic videos. 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/BKhV-kPavnk Ben's YouTube: https://www.youtube.com/@bawad Ben's TikTok: https://www.tiktok.com/@benawad Ben's Twitter: https://twitter.com/benawad Ben's startup: https://voidpet.com/ Ben's GitHub: https://github.com/benawad Ben's Discord: https://discord.gg/benawad Ben's programmer outfit: https://youtube.com/shorts/-P418Qerexs?feature=share 00:00 Teaser 00:40 Intro (Guest & Co-host) 03:40 Ben's first line of code 06:00 Turning down FAANG and Leetcode 11:33 Layoffs / Finding jobs 13:15 Skin in the game 13:58 Interviews are broken 16:44 Advice to technical content creators 22:05 Being authentic online 27:57 Coding on Twitch vs YouTube 30:10 Why you should create on TikTok 33:25 Hating Android development / Loving React 36:00 Tech stack 38:18 GitHub Copilot 39:35 Tech stack again 40:39 Deno 42:30 The AI discussion 44:10 VoidPet (Ben's startup) 49:40 Rejected by YC / fundraise vs bootstrap 56:29 Career advice to newbies 1:00:09 Ben's drip 1:01:42 Saffron App 1:04:29 Ben's mentors 1:06:25 Wrap up - 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 Parsa's Twitter: https://twitter.com/pzrsaa Parsa's website: https://parsam.io 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. #benawad #coding #programmer