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    Business

    Infinite Loops

    Every Thursday, join Jim O’Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world.

    Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, “Hmm that’s interesting!”

    Advertise
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    • Google Play
    • Spotify

    Latest Episodes:
    Ian Cassel — All Great Things Start Small (EP.113) Jul 07, 2022
    Show notes

    Ian Cassel is the founder of MicroCapClub, a community where hundreds of investors have discussions on US and Canadian microcap companies. They also help you become better investors with educational content covering investing strategies, intelligent fanatic CEOs, great investors, and more. Ian is also Founder and CIO at Intelligent Fanatics Capital Management, whose goal is to own the smallest, most illiquid, least institutionally owned, misunderstood businesses that are run by intelligent fanatics.

    • Ian's Twitter: https://twitter.com/iancassel
    • MicroCapClub: https://microcapclub.com/
    • Intelligent Fanatics Capital Management: https://if.capital/

    Show Notes:

    • Microcaps are boons for quants
    • How Ian fell in love with microcaps
    • Managing other people's money
    • Advantages and risks of microcap investing
    • Profitability, scarcity, and great stories
    • The top-down and bottom-up investment framework
    • Not being limited by minimum market caps
    • Being a hands-on investor
    • Turnovers in microcap portfolios
    • PE taking over microcap firms
    • Increasing the flywheel of serendipity
    • Preparing to be effortless
    • Not getting into arguments with people with made up minds
    • Being honest about your investment approach
    • The "mute" button hack
    • Identifying bad management
    • Importance of base rates
    • Educating about microcaps
    • Optimism beats pessimism
    • Do macroeconomic factors really matter?
    • What is chasing you?

    Books Mentioned:

    • The Psychology of Money, by Morgan Housel
    • The Tao Jones Averages, by Bennett Goodspeed

    Paul Millerd — The Pathless Path (EP.112) Jun 30, 2022
    Show notes

    After working at McKinsey and getting an MBA from MIT, Paul Millerd was succeeding well on a path that "made sense". However, things started changing when he had a health crisis, which ended up with him embarking on a pathless path. Since 2017, he's been tinkering with multiple side-hustles, writing newsletters, creating podcasts, traveling, and helping others join the pathless path.

    • Paul's Twitter: https://twitter.com/p_millerd
    • Paul's newsletter: https://boundless.substack.com/
    • 'The Pathless Path' book: https://think-boundless.com/the-pathless-path/

    Show Notes:

    • Having fun paying bills
    • Jumping off your fitness landscape
    • The first few years of being self-employed
    • Connecting with the subconscious self
    • Internet as an off-ramp
    • How to stir up curiosity
    • Lessons from DJing
    • The social construct of retirement
    • Internet economy requires showing up daily
    • Design for liking your life
    • Tinkering
    • Embracing laziness
    • Luxury of doing what you want
    • The shift from cynicism to optimism
    • Societal progress over the last decades
    • What's next for Paul?

    Books Mentioned:

    • The Pathless Path; by Paul Millerd
    • The Body Keeps The Score; by Bessel van der Kolk

    David Chilton — The Wealthy Barber (EP.111) Jun 23, 2022
    Show notes

    Dave Chilton is a Canadian author, investor, and a venture capitalist who has appeared on television in the Canadian version of Dragons' Den. In 1989, he released his book "The Wealthy Barber" which went on to sell an astonishing two million copies in Canada. You can follow Dave on Twitter at https://twitter.com/wealthy_barber and buy his book at https://www.amazon.com/THE-WEALTHY-BARBER/dp/B000SAI072 Show Notes:

    • How Dave met Jim
    • Signs of curiosity
    • "The Wealthy Barber" TV show
    • Twitter as a global intelligence network
    • Capital Camp and Rethinking Private Equity
    • Getting good at taking criticism
    • Dave's approach to writing "The Wealthy Barber"
    • The decline in business travel
    • Starting new businesses at 60
    • Helping out authors with book publishing
    • "The Chilton Method" web-series
    • Power laws in podcasting
    • Inviting Jim's kids to Infinite Loops
    • How to react if your passport gets pickpocketed
    • Living in the moment
    • Building a healthy relationship with your kids
    • The natural love for trivia
    • Collecting art
    • Anecdotal info in the world of big data
    • Still using a Blackberry

    Books Mentioned:

    • The Wealthy Barber; by Dave Chilton
    • What Works on Wall Street; by Jim O'Shaughnessy
    • Invest Like the Best; by Jim O'Shaughnessy
    • Psychology of Money; by Morgan Housel
    • The Immortality Key; by Brian Muraresku

    Meb Faber — Two Quants Walk into a Bar (EP.110) Jun 16, 2022
    Show notes

    Meb Faber is co-founder and the Chief Investment Officer of Cambria Investment Management, author of multiple books, and host of "The Meb Faber Show" podcast. You can follow Meb on Twitter at https://twitter.com/MebFaber and know more about him and his work at https://mebfaber.com/ Show Notes:

    • Replicating the Yale endowment
    • Why investors won't follow advice
    • Importance of writing down your investment plan
    • The challenges of buy and hold
    • Learning from your losses
    • Out of favor strategies
    • A dividend strategy without dividends
    • The branding issue with buybacks
    • Harsh book reviews
    • Investing in international markets
    • Are we in an expensive downtrend?
    • Stated vs. Actual preference
    • Not betting on merely sentiment
    • Robinhood with an educational spin

    Trung Phan — On Smart Threads and Dumb Memes (EP.109) Jun 09, 2022
    Show notes

    Trung T. Phan is a creator in the tech, business, and media space. His Twitter threads are full of knowledge and humor, and he also co-hosts the "Not Investment Advice" podcast. Follow Trung on Twitter at https://twitter.com/TrungTPhan and subscribe to his newsletter at https://trungtphan.com/subscribe/ Show Notes:

    • Trung's Vietnamese origins
    • Humor in your talent stack
    • Asymmetric returns of creating content online
    • The power of memes
    • Getting a CFA
    • Going back to writing movie scripts
    • Succeeding in the creator economy
    • How to acquire people's attention
    • Creating content on LinkedIn and Facebook
    • The importance of traveling
    • Donald Trump's popularity in SE Asia
    • History is not black or white
    • Steve Jobs with the Picasso
    • How a Microsoft guy catalyzed the iPad
    • Musk's space meeting with Bezos
    • Not letting complacency set in
    • Putting historical dates into perspective
    • Structuring speech to persuade
    • Jim not dissing Plato
    • Making Ted Lasso likable in 157 seconds
    • And MORE!

    Books Mentioned:

    • The Status Game; by Will Storr
    • The Beginning of Infinity; by David Deutsch
    • Virus of the Mind; by Richard Brodie
    • The Republic; Plato

    Jimmy Soni — Make Things, and Be Playful (EP.108) Jun 02, 2022
    Show notes

    Jimmy Soni is an author whose work focuses on people who create and build interesting things—whether theories, carousels, or companies. His books include "The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley", "A Mind at Play: How Claude Shannon Invented the Information Age", and more! You can follow Jimmy on Twitter at https://twitter.com/jimmyasoni and go through his work on https://jimmysoni.com/ Show Notes:

    • The joy of curiosity
    • How memes spread
    • The Great Reshuffle
    • How internet changed the publishing industry
    • Parallels between early days of PayPal and Bitcoin
    • Money as an information system
    • Appreciating the micro-level decisions
    • Three new things about Elon
    • The Elon Effect
    • How the PayPal founders brought the best out of people
    • The unknown names who were critical to PayPal
    • Claude Shannon's financial decisions
    • Wealth is a byproduct of the devotion to the craft

    Books Mentioned:

    • The Founders; by Jimmy Soni
    • A Mind at Play; by Jimmy Soni
    • Virus of the Mind; by Richard Brodie
    • The Sovereign Individual; by James Dale Davidson and Lord William Rees-Mogg
    • What Works on Wall Street; Jim O'Shaughnessy

    Peter Saddington — Love of Learning (EP.107) May 26, 2022
    Show notes

    Peter Saddington is a man of many talents. He's a software developer, founder, author, VC, and writes "The Agile VC" newsletter which covers Inside Startups, Venture Capital, and Life! You can connect with Peter on Twitter at https://twitter.com/agilepeter and subscribe to his newsletter at https://theagilevc.substack.com/ Show Notes:

    • Being exceptionally useful
    • Holding nothing close to the vest
    • Mastering the inner self
    • Peter's childhood
    • Financial future of our world
    • Antifragility of Bitcoin
    • Mining cryptocurrencies
    • Infinite Loop's NFT journey
    • The future of NFTs
    • How Peter got censored on YouTube
    • The rise of Substack
    • Jim's business ideas for the new world
    • The unfair advantage of a physical connection
    • Fixing your house before fixing the world
    • Most important skills to have for a young person
    • Manifestation is about taking action

    Ben Hunt — Preserving the Physical Metaverse (EP.106) May 19, 2022
    Show notes

    Ben Hunt is the creator and primary author of Epsilon Theory, and co-founder and CIO at Second Foundation Partners. Epsilon Theory is a newsletter that examines markets through the lenses of game theory and history. Over 100,000 professional investors and allocators across 180 countries read Epsilon Theory for its fresh perspective and novel insights into market dynamics. You can follow Ben on Twitter at https://twitter.com/EpsilonTheory and read Epsilon Theory here: https://www.epsilontheory.com/ Show Notes:

    • Neurolinguistic hard reset
    • Ben's days at Harvard
    • Why Klaus Schwab is a raccoon
    • Human beings are social animals
    • How language impacts and limits us
    • The cost of the Metaverse
    • How the nudging state is rewiring us
    • Does narrative follow price, or is it the inverse?
    • Traders respond to stories everyday
    • How technology can fight the nudging state.
    • NOAH: An ark of stories on the blockchain

    Books Mentioned:

    • The WEIRDest People in the World; by Joseph Henrich
    • How the Irish Saved Civilization; by Thomas Cahill

    Brian Feroldi — Spreading Financial Wellness (EP.105) May 16, 2022
    Show notes

    Brian Feroldi is the author of the book "Why Does The Stock Market Go Up?: Everything You Should Have Been Taught About Investing In School, But Weren't". His mission statement is "To Spread Financial Wellness", and he does exactly that in this episode of Infinite Loops! You can connect with Brian on Twitter at https://twitter.com/BrianFeroldi and get his book from Amazon at https://www.amazon.com/Why-Does-Stock-Market-Everything/dp/1735066168/ Show Notes:

    • Brian's first exposure to the stock market
    • The power of mission statements
    • Personal finances over investments
    • Paying off your mortgage early
    • Finding high-quality companies
    • (Business) Momentum investing
    • Brian's Investment Checklist
    • Importance of narratives in investments strategies
    • 99% of great investing is doing nothing
    • On being wrong, and learning from mistakes
    • DCA'ing into index funds
    • Capitalism is brutal
    • Knowing Tom Engle

    Books Mentioned:

    • Why Does The Stock Market Go Up?; by Brian Feroldi
    • The Tao Jones Averages; Bennett W. Goodspeed
    • How To Retire Rich; by Jim O'Shaughnessy
    • The Intelligent Investor; by Benjamin Graham
    • The Psychology of Money; Morgan Housel
    • Just Keep Buying; Nick Maggiulli

    Tracy Alloway — Understanding Financial Crises (EP.104) May 12, 2022
    Show notes

    Tracy Alloway is the co-host of the Odd Lots podcast and a managing editor at Bloomberg Markets. You can follow Tracy on Twitter at https://twitter.com/tracyalloway and listen to her podcast here: https://open.spotify.com/show/1te7oSFyRVekxMBJUSethH Show Notes:

    • Financial crisis hindsight
    • Being obsessed with risk and systemic stability
    • Historical parallels to the crisis of '08
    • Macro vs. micro bullshitting
    • Why people refuse to say "I don't know"
    • Victorian chicken bubble
    • Tales of forensic accounting
    • NFTs being used to launder money?
    • NFTs' path to success
    • Insights from collapse of previous civilizations
    • Understanding the Human OS
    • Fair Wages for Robots
    • Praise for Citi's Matt King and Credit Suisse's Zoltan Pozsar

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