113 episodes
Infinite Loops Jim O'Shaughnessy and Jamie Catherwood
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- Business
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4.7 • 19 Ratings
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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.
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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 -
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 -
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 -
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 -
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 -
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
Customer Reviews
Always makes me think
Love this podcast. Always provides a perspective I didn’t consider.
Grace/Humility
Wisdom - From Concentrate.
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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