Jim O'Shaughnessy

Quotes are word for word from the source.

• Human machine collaboration

  “I'm a huge believer in the centaur model, human plus machine making for the best.”

  Our noteJim describes his preference for using AI as an augmentation of human intelligence.

• Kindness Versus Niceness

  “I endeavor and try to be kind. I'm not particularly nice, though.”

  Our noteJim reflects on his personal values regarding how he treats others.

• Overcoming obstacles

  “overcoming obstacles is how you get better at a craft. I mean, it's part of our ancient DNA, I think, see problem, try to figure out, and then you continue to try to figure out”

  Our noteJim discusses how facing and solving problems is essential for improving one's skills.

• Short term trap

  “if you bring hyperbolic discounting to everything, you're fucked because essentially your world is what you're seeing right now and only today.”

  Our noteJim warns against the dangers of extreme short-termism in business and life.

• The power of AI

  “if you understand the leverage inherent in... This is Promethean fire.”

  Our noteJim compares the transformative power of AI to the discovery of fire.

• Perception vs Fact

  “I think often people confuse their opinions that are generated from their perceptions as facts. I luckily do not suffer that delusion. So this is just my, or think I don't suffer, maybe I do.”

  Our noteJim discusses how people mistake their subjective perceptions for objective reality.

• Faith in youth

  “I, like you have great faith in young people. I think that the classic older generation dumping on the younger generation, there's a joke about when they finally translated the first Sumerian Cuneiform.”

  Our noteJim expresses his optimism about the younger generation despite common criticisms from older people.

• Generational envy

  “I often think that that's more envy than anything else because as we get on in years, we're like, "Oh, they're so young." And so then we go, "Well..." We invent excuses for why they're horrible”

  Our noteJim reflects on why older generations tend to criticize younger ones unfairly.

• Dangers of appearance

  “Yeah, that is one of the great dangers, I think.”

  Our noteJim agrees that evil often looks regular or boring rather than bombastic.

• Reflective feedback tools

  “Rose, bud, thorn is interesting because we didn't have that when I was a kid. My grandchildren absolutely love that.”

  Our noteJim discusses a feedback method used by his grandchildren to share their daily experiences.

• Digital Native Efficiency

  “I have a lot of young people who are team members here at O'Shaughnessy Ventures, and one of the things that I absolutely find fascinating is they can do things in five minutes on an iPhone that an old me would be going, ah.”

  Our noteJim observes the natural proficiency of younger generations with modern technology.

• Education and creativity

  “Yeah. Yeah. It sometimes seems like our school system was designed to crush creativity.”

  Our noteJim was discussing how traditional schooling often eliminates a child's natural curiosity.

• Mastering AI prompts

  “the ability to ask good and better questions, to structure them better is going to be a big part, I think, of getting the most out of AI.”

  Our noteJim discusses how the quality of input determines the quality of AI output.

• Iterative questioning

  “You use a Socratic method of iteration to get closer and closer to what they're really looking for.”

  Our noteJim observes the effectiveness of using follow-up questions to refine a search for information.

• Skills over knowledge

  “They care what they can do and what they can do tends to demonstrate what they've learned.”

  Our noteJim discusses why practical ability is more important than theoretical knowledge in hiring.

• Raw honesty in writing

  “Your training in journalism is pretty obvious here. But the thing that I want to ask you about first is the raw honesty that you write in this book really kind of took me back.”

  Our noteJim is praising Danielle Crittenden's memoir about grief for its unflinching and honest approach.

• Real resilience

  “most of the shit you read from the happiness purveyors and the TED talkers and that's it's bullshit. But there is a way to survive this, right?”

  Our noteJim criticizes superficial advice on happiness while acknowledging the possibility of surviving deep grief.

• Initiative origins

  “So let's start out with the background on what was the environment that led everyone at Lux to decide, you know what? We should launch a Riskgaming initiative.”

  Our noteJim is asking about the catalyst for starting a new strategic project.

• Short term thinking

  “one of the things that continued to surprise me was the number of people, really, really smart people, who were just hyperbolic discounting. And everything was like, yeah, no, I can't make that decision for five years from now.”

  Our noteJim discusses the prevalence of short-termism among intelligent investors and executives.

• AI integration

  “every one of our workflows at O'Shaughnessy Ventures has an AI component built into it.”

  Our noteJim describes how his venture firm has fully integrated AI into their daily operations.

• Steelmanning arguments

  “essentially one of the best use cases that we've found internally is just for steelmanning our own arguments.”

  Our noteJim discusses using AI to build the strongest possible version of an argument to test it.

• Evidence based trust

  “I would trust the doctor who said, "I think that this is your condition. Here are the 10 years of double-blind tests on this specific medication that I'm recommending for you. What do you think?”

  Our noteJim explains why he prefers empirical models over gut feelings in investment and medicine.

• Action over perfection

  “if you want to have a perfect record, you won't have a record at all because you won't have made any mistakes and therefore, you will have done nothing.”

  Our noteJim warns against the paralysis caused by the fear of making mistakes.

• Intellectual humility

  “I always believe that I'm generally wrong most of the time. And so it helps to interact with people who are actually using, in our case, Canvas”

  Our noteJim shares his mindset regarding product development and user interaction.

• Role Models

  “I think both of you are incredible north stars for others to follow similar paths.”

  Our noteJim reflects on the inspiring nature of the two social entrepreneurs' journeys.

• Dangers of standardization

  “And you know what's interesting is it's a kiss of death everywhere. It's not just in academia, in school, in business, it's literally everywhere.”

  Our noteJim comments on how rigid standardization leads to failure in various fields.

• Escaping the Rut

  “In Britain, they had been making guns and machines and all that for hundreds of years, and they had fallen into the rut. It isn't done that way here.”

  Our noteJim compares the rigid traditions of British industry to the flexible innovation of early America.

• Protecting your attention

  “Without that filter, you squander your attention, to your point. And so I guess my question to follow would be, I have an answer for your complaint. I read transcripts of podcasts that I'm interested in.”

  Our noteJim suggests reading transcripts as a more intentional way to consume information than passive listening.

• Market as puzzle

  “I loved the stock market, because it seemed to me to be this ultimate puzzle and kind of the Olympics of business.”

  Our noteJim describes his early fascination with the stock market as a competitive intellectual challenge.

• Intellectual humility

  “I think that most of the things those people 500 years ago, the smartest most switched on humans on the planet, most of what they believed was absolutely wrong.”

  Our noteJim reflects on how even the most brilliant minds in history held beliefs that were eventually proven wrong.