TAO TE JIM
Jim O'Shaughnessy's Approach to the Meta Problem of Humanity.
Very occasionally, people come into my life who have an outsized impact on my view of the world. Some are obvious (my husband, my son), others probably don't even know I exist. Today I want to write about the latter.
Jim is the equivalent of the Medici1 family on steroids, powerlifting the The Personal Agency Renaissance. If I had to choose just one person to follow for life-altering, well curated ideas, it would be fund manager, systems thinker and multidisciplinary renaissance man - Jim O'Shaughnessy.
What has his life’s work and content done for me?
A convincing approving nudge to really keep thinking outside of the box. A regular push to level up my game and not succumb to mediocrity. His guests are a reminder that you don’t need to be ‘rich’ to live a life you really love. I feel that's missing a lot, especially in finance/corporate land. You rarely encounter someone who knows they have ‘enough’ and act like it.
After years of following Jim, my general worldview has flipped from leaning towards “Black Mirror” outcomes to a healthy enthusiasm about the direction and future of humanity. Great book recommendations and people he interviews have helped with this. It is akin to a regular infusion of curiosity across various domains.
I think I have figured out Jim’s secret sauce.
He has deciphered the core principle, the meta-truth, behind most of our world's problems (and solutions):
Reality is created first in the minds of people and then it manifests as the world we experience. Everything else is a derivative flowing from this. Of course, nothing gets done unless you take action, but the absolute first thing is the ability to See, Imagine and Think differently.
However, our way of perceiving and believing, our ‘Human OS’ as Jim calls it, is full of bugs.
Despite selling his Asset Management firm for billions and never having to work again, he is tirelessly making sure that our Human OS and opportunities are up to speed with The great reshuffle2 - a period of exponential change where all old traditional models are collapsing and our Human OS is being pushed to update.
As the Medici did during the Renaissance, Jim does through O'Shaughnessy Ventures. He is the financier and patron of many creatives, start-ups and tinkerers in various non-zero sum fields. The fund focuses on 4 specific areas: Infinite Adventures, Infinite Films, Infinite Media, and the O'Shaughnessy Fellowships program.
OSV Ventures invests and influences businesses building the future. Examples are Stability AI and Synthesis School, where my 8 year old son enjoys exploring lessons with his AI tutor.
Infinite Films is creating White Mirror scenarios so we stop worrying about everything going to hell. OSV also started a book publishing company. To paraphrase Jim: ‘Talent and genius are equally distributed. Old gate keepers have a habit of blocking access. We can identify them and we can fund them.’
In his podcast and newsletter, Jim champions books and writers that have the potential to free a person from stale ideas and various unexamined anxieties. The quality content delves into consciousness, biases, science, AI, futurism, art, science, finance and education.
Jim on Human OS
Nostalgia is basically bullshit. We hallucinate a lot of our past. Because humans have a strong need for illusion of control, minds overwrite and update our memories to make it consistent with what we think now. I found his thinker and prover parable especially interesting when considering deeply held beliefs.
‘Desire for certainty is a big bug in human OS. Premature certainty is a massive mistake. You are almost always wrong initially. Only the madman is certain.’
Jim says everyone wants progress but no one wants to change, but we need to be aware that progress always comes with problems but they become better problems. If you can't evolve yourself, the change that's happening in society still can't be stopped. Hence his obsession (and mine) with Human OS - the underlying driver of everything impacting the world.
“The only certainty is movement and change. Stasis is death.” - Jim is often seen quoting from Tao Te Ching3
Cognitive biases are similar to a cognitive mirage - you don’t stop seeing it. You don't stop walking towards it. Learn to write things down on paper for clarity of thoughts. Jim has 40+ years of journals which he will convert to machine readable format.
“We need the discipline of Sparta around our Athenian delusions....develop a process you don't emotionally overwrite.4”
He learned the usefulness of Pre-meditation from his grandfather: You write down by hand - I want X, all the ways your life might change if you get X, but then you state the negatives of getting X. Do the same for the option where you don’t get X. You write the positives and negatives to tame any excess bias.
“You have to be Lao Tsu AND Confucius, always walking on a razor edge. All emotion or all reason is suboptimal. If you over optimize to either side it's not great.”
The edge he continuously uses in investing is the fact that Human nature doesn’t change. Here is a thread on how to arbitrage it in investing. Jim also published several great books for investors that are worth exploring.
‘It seems that the one thing that doesn't change is people's reaction to short-term conditions and their axiomatic ability to perpetuate them far into the future.’
Jim on parenting:
“We want to raise great adults, which precludes a lot of traps young parents fall into, for example saying ‘Because I am the parent and you are the child’ or ‘My house my rules’, nothing that would make them believe you are right and they are wrong.' If a child has compelling arguments, take them seriously. Make them understand they have agency. We encourage them to question and challenge us. I do not live vicariously through my children. Don't get your children to be mini versions of you.”
Key inspiration for me:
The idea that doing what makes you jump out of bed in the morning is important and can be combined with managing money. The endless give, even after you have made it financially, is a place where there is no space for mid life crisis, depression, loneliness or other plagues.
I have found in my own life the principles and wisdom of Tao Te Ching as generally true and helpful with the ultimate optimal way of being, living and yes, parenting. Hence the name of the blog - Wu Wei, the principle of effortless action, the ultimate mastery of ‘flow’. Jim confirmed that I am not alone and crazy in this area.
How to access
The Podcast Infinite Loops has proven to be valuable for developing an ever more nuanced mindset. Featuring a variety of guests, themes, and disciplines, it spans from heavy hitters like Cliff Asness to “ordinary” people who are doing something extraordinary.
OSV Ventures Newsletter is excellent.
Jim’s twitter
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When Write of Passage's last assignment required a curation piece on an online persona worth knowing, I cringed. As a trader, I am allergic to displays of excess praise - I know how easy it is to tip the emotional balance out of equanimity. Nevertheless, it is great to venture out of the comfort zone sometimes. As the course is coming to an end, I am super grateful for the conversations with and feedback from , , ,, , ,, , .
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Florentine dynasty who were influential patrons during the Renaissance. Provided crucial support to a diverse array of intellectuals and artists. https://themedicifamily.com/
A breakdown of the Great Reshuffle https://twitter.com/InfiniteL88ps/status/1538137705288462339
Written 2000 years ago, the book is a foundational text of Taoism, based upon a concept of the Tao, or Way, as the universal power through which all life flows. https://en.wikipedia.org/wiki/Tao_Te_Ching
I have not been following Jim O'Shaughnessy, Anna. Now I'm inspired to do so.
I enjoy your work and the depth you bring to it immensely. This is the start of a new friendship.
I’m tuning into Infinite Loops now, Anna. Thank you for this thoughtful recommendation. I love the idea of seeking possibility instead of being mired down by the doomsday. And I love what you wrote about nostalgia being a series of hallucinations. So true.