113 episodes

Sometimes we get caught up in what feels like infinite loops when we try to figure things out. Markets go up and down, research is presented and then refuted, and we wind up right back where we started.

The goal of this podcast is to learn how we can reset our thinking on issues that leaves us with a better understanding as to why we think the way we think and how we might be able to change that, to avoid going in infinite loops and thoughts.

Hosts, Jim O’Shaughnessy and Jamie Catherwood, hope to offer you a fresh perspective on a variety of issues and look at them through a multi-faceted lens. Including history, philosophy, art, science, linguistics, and quantitative analysis. And help you become a better investor and also a more nuanced thinker.

Infinite Loops Jim O'Shaughnessy and Jamie Catherwood

    • Business
    • 4.7 • 19 Ratings

Sometimes we get caught up in what feels like infinite loops when we try to figure things out. Markets go up and down, research is presented and then refuted, and we wind up right back where we started.

The goal of this podcast is to learn how we can reset our thinking on issues that leaves us with a better understanding as to why we think the way we think and how we might be able to change that, to avoid going in infinite loops and thoughts.

Hosts, Jim O’Shaughnessy and Jamie Catherwood, hope to offer you a fresh perspective on a variety of issues and look at them through a multi-faceted lens. Including history, philosophy, art, science, linguistics, and quantitative analysis. And help you become a better investor and also a more nuanced thinker.

    Paul Millerd — The Pathless Path

    Paul Millerd — The Pathless Path

    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

    • 1 hr 17 min
    David Chilton — The Wealthy Barber

    David Chilton — The Wealthy Barber

    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

    • 1 hr 16 min
    Meb Faber — Two Quants Walk into a Bar

    Meb Faber — Two Quants Walk into a Bar

    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

    • 1 hr 13 min
    Trung Phan — On Smart Threads and Dumb Memes

    Trung Phan — On Smart Threads and Dumb Memes

    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

    • 1 hr 21 min
    Jimmy Soni — Make Things, and Be Playful

    Jimmy Soni — Make Things, and Be Playful

    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

    • 1 hr 19 min
    Peter Saddington — Love of Learning

    Peter Saddington — Love of Learning

    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

    • 1 hr 11 min

Customer Reviews

4.7 out of 5
19 Ratings

19 Ratings

Hauseofraf ,

Always makes me think

Love this podcast. Always provides a perspective I didn’t consider.

Does what it claims ,

Grace/Humility

Wisdom - From Concentrate.

DCarradona ,

High quality guests, some improvements possible

Jim is a smart man but I think he can learn from his son, Patrick, in the way that Patrick curates episodes and lets his guests set tempo in each episode. Additionally, Jim should make a larger effort to bring Jamie into the episodes earlier. I can recall historical episodes where Jamie randomly starts speaking 15-20 minutes into an episode and it can be somewhat surprising.

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