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  • 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

  • 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

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  • 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

  • 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

    -

    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

    -

    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

  • 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

  • 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

  • Jack Raines is the fastest growing finance & money blogger on the planet right now. He created the Young Money blog (https://www.youngmoney.co/) just 15 months ago and has already amassed 30,000+ subscribers. He has already been offered book deals by world class publishers. Leverage ftw. 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 where we recorded this in person with Jack: https://youtu.be/F56YIktbMHY

    Jack's newsletter: https://youngmoney.co
    Jack's Twitter: https://twitter.com/Jack_Raines
    Jack's travel blog: https://www.backpackin.blog/


    00:00 Teaser
    01:24 Jack intro
    04:29 Jack's childhood
    07:49 Deported from Norway
    11:23 Vagabonding and European life
    21:00 Trading at 21 years old
    27:25 F U Money
    35:40 Stick men drawings
    36:58 6 types of wealth
    43:49 Crypto and Balaji
    58:00 Young Money monetisation
    1:03:18 Writing a book
    1:07:23 LinkedIn vs Twitter
    1:11:13 Distribution
    1:13:50 Pitching your work and meeting Morgan Housel
    1:17:25 How Jack writes
    1:22:20 Inspiring writers
    1:26:27 Book shaming and meaningful insults
    1:30:57 Opportunity cost of everything
    1:35:32 Value in MBAs
    1:40:35 Jack's favourite books
    1:41:47 Dating in US vs UK

    -

    Get in touch with us:

    YouTube: https://youtube.com/rationalvc
    Our website (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.

    #finance #money #blogger

  • Luke Burgis has co-created and led four Silicon Valley companies in wellness, consumer products, and technology. He is the author of the best selling book "Wanting: The Power of Mimetic Desire in Everyday Life", which breaks down the theories of French philosopher René Girard. Luke is currently Entrepreneur-in-Residence and Director of Programs at the Ciocca Center for Principled Entrepreneurship, where he also teaches business at The Catholic University of America.

    Girard's theories explain most human-related interactions, such as the virality of social media, the rise of Facebook, political beliefs, cancel culture and how the best investors pick the best companies. Luke deep dives into mimesis and his life's work with Iman and Cyrus on this latest Rational VC podcast.

    Luke's website: https://lukeburgis.com/
    Luke's Twitter: https://twitter.com/lukeburgis

    Timestamps:

    00:00 Intro
    01:37 Intro to Luke
    02:58 Working in bars
    05:30 Luke's background
    09:03 Shark tankification of worth
    12:13 Mimetic tips for founders
    14:52 Mimesis in venture capital
    17:17 Cultivating an interdisciplinary mind
    21:02 How to write well
    25:40 René Girard intro
    27:48 Mimesis
    31:04 Finding a spouse
    34:33 Idols
    38:20 Mediators and comedians
    41:10 Rituals
    48:56 Anti-mimesis
    52:54 Negative mimesis
    55:20 Mimesis in PR
    57:08 Deep silence
    1:00:51 Navigating without GPS
    1:04:24 How to reach Luke

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • In this Rational Musings episode, Iman and Cyrus discuss their views on whether setting up a fund or running a syndicate (SPV) makes the most sense. The guys also talk about angel investing, joining a fund and scouting deals as alternatives to running an SPV or fund.

    Submit questions for us to cover in podcast episodes: https://www.rationalvc.com/questions

    Materials referenced

    Samir Kaji tweet 1: https://twitter.com/Samirkaji/status/1522757321809485824

    Samir Kaji tweet 2: https://twitter.com/Samirkaji/status/1541979202953433088

    Ryan Hoover tweet thread: https://twitter.com/rrhoover/status/1473347361762066438?lang=en-GB

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos on all things tech investing and building. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, SPACs etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    YouTube: https://www.youtube.com/c/rationalvc

    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • Michael Safai is the Founding Partner of Dexterity Capital, an algorithmic high-frequency trading firm focused on cryptocurrencies. The lean team makes between $2 billion and $4 billion in trades per day. Michael is a seasoned operator in tech, with a multidisciplinary background with careers in tech and law, and an academic background in astrophysics and economics from UC Berkeley. Dexterity Capital are defining – and constantly redefining – algorithmic trading for all areas of the cryptocurrency world. They specialise in market neutral strategies. That means they thrive regardless of whether the bulls or bears are winning. With offices in Seattle, San Francisco, New York, and London they run their strategies 24/7 around the globe.


    You can also watch this episode on our YouTube channel.


    Dexterity's website: https://dexterity.capital/
    Michael's Twitter: https://twitter.com/michaelsafai/
    Michael's LinkedIn: https://www.linkedin.com/in/msafai/

    https://rationalvc.com

    Timestamps:

    00:00 Michael's background
    06:54 Dexterity Capital
    11:08 Price inefficiencies
    15:40 TradFi vs. DeFi
    17:52 Due diligence (Seed & DeFi)
    20:00 Is Crypto institutional money?
    23:50 Current market situation
    25:55 Maximalism vs. rationalism
    30:00 The web3 discussion
    32:42 Operating: how Michael runs his company
    40:00 Career advice trying to get into this space
    44:00 Mentors and lessons
    45:50 Resources to learn
    47:40 Wrap up

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • In this Rational Musings episode, Iman and Cyrus discuss antifragile principles of their favourite author - Mr Nassim Nicholas Taleb. The fellas dissect a Seeking Alpha article on managing an antifragile portfolio and also talk how to apply antifragile principles in daily life.

    Submit questions for us to cover in podcast episodes: https://www.rationalvc.com/questions

    Materials referenced

    Seeking Alpha article: https://seekingalpha.com/article/4454512-7-rules-for-an-antifragile-portfolio

    Taleb convexity article: https://www.edge.org/conversation/nassim_nicholas_taleb-understanding-is-a-poor-substitute-for-convexity-antifragility

    Danial Vassallo Twitter: https://twitter.com/dvassallo?s=20&t=oQi_Tf63eVgWkw04MJ144Q

    Naval on asymmetric opportunities: https://twitter.com/naval/status/1054984950192181248?lang=en-GB

    Bill Ackman Netflix shareholder letter: https://assets.pershingsquareholdings.com/2022/04/20184527/Letter-to-Shareholders-4.20.2022.pdf

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos on all things tech investing and building. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, SPACs etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    YouTube: https://www.youtube.com/c/rationalvc

    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • Eric Jorgenson is an author and the creator of "The Almanack of Naval Ravikant" book. He is also an Angel Investor and Entrepreneur. Eric recently launched his rolling fund on AngelList. He was on the founding team of Zaarly, and has been publishing online since 2014. His blog has educated and entertained over a million readers. The guys discuss everything from Building Wealth and Judgement, to Leverage, Naval, Balaji, Angel Investing, Web3, writing books, content creation, and much more.


    You can also watch this episode on youtube at:
    https://youtu.be/_LMoWRF-q3E

    Eric's website: https://ejorgenson.com
    Eric's Twitter: https://twitter.com/EricJorgenson
    Eric's rolling fund: https://rolling.fun
    Navalmanack free download: https://navalmanack.com

    https://rationalvc.com


    Timestamps:

    00:00 Teaser
    00:48 Intro chit chat
    03:12 Eric's roots
    04:56 Why Eric wrote the Navalmanack
    07:23 Babak Nivi and Venture Hacks
    11:28 Building wealth, judgement, and happiness
    13:52 Improving decision making
    17:33 Productise yourself
    25:53 Authenticity vs. views
    30:44 Leverage and social media
    34:24 High leverage side projects
    38:03 Leaving the conventional path
    43:33 Process of publishing a book
    53:02 Writing essays online
    58:26 Launching a rolling fund / investment thesis
    1:06:57 Angel Investing
    1:11:23 Crucial to be an operator before investing
    1:15:27 Mindset in private markets vs public markets
    1:17:33 Balaji Srinivasan's big ideas / balmanack
    1:24:05 The Web3 discussion
    1:35:39 Resources that have shaped Eric's world view
    1:37:57 Outro chit chat

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • On this Rational Musings, Iman and Cyrus discuss René Girard's mimetic theory and real life anti-mimetic principles. The guys dissect Luke Burgis' article on living a counter cultural life and why being anti-mimetic is important for becoming antifragile.

    Submit questions for us to cover in podcast episodes: https://www.rationalvc.com/questions

    Materials referenced

    Luke article: https://www.epsilontheory.com/25-anti-mimetic-tactics-for-living-a-counter-cultural-life/#

    Luke book "Wanting": https://lukeburgis.com/wanting/

    Epsilon Theory: https://www.epsilontheory.com/

    Taleb on religion: https://econjwatch.org/articles/religion-heuristics-and-intergenerational-risk-management

    Simon Sarris: https://simonsarris.substack.com/p/in-praise-of-the-gods?s=r

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos on all things tech investing and building. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, SPACs etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • Mac Conwell ("Mac the VC") is the Founder and Managing Partner of RareBreed Ventures. Mac is a former software engineer and a two-time founder. One of Mac's companies failed, the other went on to a successful exit. He then broke into the world of investing by working for the State of Maryland, before raising a fund of his own in a short amount of time. From homeless to VC, "hacker turned hustler", RareBreed has seen tremendous success in a short amount of time.

    You can also watch this episode on youtube at: https://youtu.be/yUZLzY-fyJU

    https://twitter.com/macconwell
    https://rarebreed.vc
    https://rationalvc.com

    00:00 Intros
    02:32 Psychology from homeless to VC
    07:58 How Mac got into VC
    13:14 Raising a fund off Twitter
    19:07 Overlooked & underserved founders
    23:35 Diligence / what Mac looks for
    30:41 Biases in Silicon Valley
    34:58 Mac's advice for Cyrus and Iman
    41:30 Mistakes to avoid after raising a fund
    43:15 Technical skills vs selling skills for founders
    46:30 Mac's mentors
    49:23 Mac's personal values & principles

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • Cyrus and Iman are back and they're in person! The Rational VC guys talk to the super impressive founders of Odin, Paddy and Mary. Odin is a platform and community democratising access to early stage investing. In this long-form discussion, Iman and Cyrus talk to the Odin founders about their backgrounds, childhoods, Odin's origin story, Odin's future, community building, the democratisation of access and education.

    https://joinodin.com/

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • Andrew is a seasoned founder (2 exits) and is now the founder of MicroAcquire, a startup acquisition marketplace that helps startups find buyers and get acquired. MicroAcquire has seen tremendous success in a short amount of time. Andrew explains his tough childhood and formative years that led to him becoming an entrepreneur, what it takes to become a success, building in public as a CEO, the company's future plans, and his thoughts on juggling family life with business.

    www.microacquire.com

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • On the latest Rational Musings, Iman and Cyrus discuss their favourite principles, spanning investing / business, life and learning. In this Lindy episode, they go deep and share their rational thinking on a list of 116 principles as outlined by Junto Investments.

    You can also watch this in video format on our youtube channel to see supporting material: https://youtu.be/CSKMJ_rZpt8

    Material referenced:

    Junto Principles: https://junto.investments/principles/

    Odin: https://joinodin.com/

    Iman video first principles: https://www.youtube.com/watch?v=pPv4DWkamM8&t=1s

    Cyrus essay on angel investing: https://www.rationalvc.com/articles/angel

    Iman essay on contrarianism: https://www.rationalvc.com/articles/contrarian

    Cyrus essay on financial minimalism: https://www.rationalvc.com/articles/minimalism

    Nassim Taleb barbell strategy: https://www.investopedia.com/articles/investing/013114/barbell-investment-strategy.asp

    Buffett's bet: https://www.investopedia.com/articles/investing/030916/buffetts-bet-hedge-funds-year-eight-brka-brkb.asp#:~:text=In%202008%2C%20Warren%20Buffett%20issued,Bloomberg%20op%2Ded%20in%20May.

    Naval and Nivi Spearhead: https://podcastnotes.org/spearhead-with-naval-ravikant-and-babak-nivi/spearhead-naval-ravikant-babak-nivi/

    Babe Ruth effect VC: https://a16z.com/2015/06/08/performance-data-and-the-babe-ruth-effect-in-venture-capital/

    Aaron Clarey Asshole Consulting: https://assholeconsulting.com/

    Jamie Dimon China: https://www.nytimes.com/2021/11/24/business/jamie-dimon-china.html

    Nassim Taleb Dimon tweet: https://twitter.com/nntaleb/status/1463863377860743173

    Chamath Stanford lecture: https://www.youtube.com/watch?v=FWAKL8G1lkg

    Cal Newport boredom article: https://www.calnewport.com/blog/2009/02/04/have-we-lost-our-tolerance-for-a-little-boredom/

    Ray Dalio principles: https://www.youtube.com/watch?v=B9XGUpQZY38

    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos on all things tech investing and building. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, SPACs etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.

  • Cyrus and Iman discuss their thoughts on authenticity in life, tech, and VC. They also discuss having purpose and performing deep work, whether elite university degrees are becoming a bad investment, applying the Wall Street DNA to Venture, and how Twitter activity influences VC funding outcomes.

    You can also watch this in video format on our youtube channel to see supporting material: https://youtu.be/2O7Ugp_kmDQ

    Materials referenced:

    James Lo post on authenticity: https://www.linkedin.com/posts/yfjame...

    Rob Henderson on university degrees:
    https://twitter.com/robkhenderson/sta...

    Sar Haribhakti on Tiger Global applying Wall Street DNA:
    https://twitter.com/sarthakgh/status/...

    Ethan Mollick on Twitter influencing funding:
    https://twitter.com/emollick/status/1...


    --

    Rational VC provides regular content on technology investing and technology building. We also write long-form memos on all things tech investing and building. You can sign up for these monthly memo newsletters on the website: https://www.rationalvc.com/

    We break everything down to first principles, to simplify the complex technology world. We aim to bring you content that is insightful, logical, and rational.

    We cover tech products and tech companies across the lifecycle, from pre-seed to seed, Series A to D+, to IPOs and beyond. We also cover all investing methods including Angel Investing, Venture Capital, Private Equity, Hedge Funds, Public Markets, SPACs etc.

    For more information on Cyrus, Iman and the channel, check out:
    https://www.rationalvc.com/

    https://www.linkedin.com/in/cyrusyari/
    https://www.linkedin.com/in/imanolya1/
    https://twitter.com/CyrusYari
    https://twitter.com/iman_olya

    Apple Podcasts: https://podcasts.apple.com/gb/podcast/rational-vc/id1537462327


    Your feedback and comments are very welcome. We hope you enjoy listening as we embark on a journey to understand this space; clearly, and rationally, of course.

    ---

    Disclaimer: The content and materials provided are solely for informational 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.