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

Every podcast episode we explore a Lindy book, and find ideas you can use in business and life. Join 3,000+ curious minds and avid readers @ rationalvc.com to get free access to essays and exclusive content. For the video version of 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

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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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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

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 

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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 
Parsa's Twitter: https://twitter.com/pzrsaa 
Parsa's website: https://parsam.io 
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.

#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

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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

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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.

#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

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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.

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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.

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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.