Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The companies that tend to win in technology are the ones that are able to identify the inflection point on the S-curve early enough to make a big bet, but not so early that they run out of capital before the market develops. The penalty for being too early is often indistinguishable from being wrong.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The way I think about it is that the most dangerous time to own a technology business is when it's currently executing well but the next curve is about to start. Because what happens is all your best people, all your resources, all your management attention is focused on scaling and perfecting the current curve, and the new curve looks tiny and unimportant by comparison.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The other thing I'd say about AI is it has this strange property where the more you use it, the more you realize how transformative it's going to be. Most technologies, the more you use them, the more you understand their limitations. AI is almost the opposite — the more deeply you engage with it, the more you realize the ceiling is higher than you thought.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The great irony of technology investing is that the stocks that look the most expensive at the beginning of an S-curve are often the cheapest, and the stocks that look the cheapest at the end of an S-curve are often the most expensive.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The S-curve is a very well-known concept in technology investing, but what's less appreciated is that the most dangerous moment is often at the top of the S-curve, when a technology looks the most dominant and the most entrenched. That's precisely when the next S-curve is being born underneath it, and the incumbents are most blind to the threat.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The best tech investors understand that the S-curve is not just a description of what happened — it's a prediction tool. When you're early on the S-curve, the technology is improving faster than the market appreciates, and when you're late, the technology is maturing faster than the market appreciates.

SpaceX IPO Gigastream

SpaceX IPO Gigastream

Bill Gurley doesn't want a crazy pop on day one, doesn't want it to go up 100%. If we're in 10, 20, 30% range for something this big, that just feels like... Everything came together properly.

Pivot

Scott Galloway on SpaceX IPO: "The Game Is Rigged" | Pivot

You have what is in my opinion the greatest degree of manufactured scarcity ever in an IPO and this is about to be the greatest transfer of wealth from retail investors since crypto

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The biggest mistake investors make is that they think about technology adoption as linear, when in reality it follows an S-curve. The early part of the S-curve looks like nothing is happening, and then suddenly everything happens at once, and then it plateaus. Most investors are either too early and give up, or they extrapolate the steep part of the curve forever.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The exciting part of being in technology investing is that you have these waves of innovation that create extraordinary opportunities for value creation and also value destruction. And the companies that are able to ride multiple waves are extraordinary compounders over time, but it's actually quite rare.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The failure mode that I've seen in technology investing over my career is people who are trained on a particular way that technology markets work, and they can't break free of it. They have a very successful decade, typically, where they nail one cycle, and then the next cycle they try to map the old framework onto the new one, and that's where the mistakes get made.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The best investors in technology don't just understand the technology itself — they understand where they are on the S-curve. Most people anchor to the present and extrapolate linearly, but the whole game is recognizing when adoption is about to inflect and when it's about to plateau.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

The thing about activism is that there's a forcing function. You've done all this work. You own the stock. You think there's value. But the management may be destroying value or not realizing the value, and at some point you have to do something about it or you're just going to sit there and watch your investment go to zero.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The mistake most investors make is they think about technology investing as stock picking, when really it's about cycle recognition. If you can identify where you are on the S-curve of a technology's adoption, the individual stock selection becomes almost secondary to being in the right part of the cycle at the right time.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The mistake most investors make is they think about technology investing as a static exercise — you find a great company, you understand its competitive position, you underwrite the earnings, and you hold it. But technology is defined by change, and so you need to have a framework for thinking about how industries evolve over time.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The business of investing in technology is really the business of identifying where you are on the S-curve, because most of the money that's ever been made in technology investing has been made by people who correctly identified that they were in the early innings of a very long S-curve, and most of the money that's ever been lost has been by people who thought they were in the early innings when they were actually in the late innings.

Invest Like the Best with Patrick O'Shaughnessy

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

The other thing about platform transitions is that they reset competitive advantage. So the incumbents that have accumulated distribution and integration and switching costs — those advantages largely reset with platform transitions. That's what makes them so valuable for investors; new winners can emerge from what looks like chaos.

The Prof G Pod

The Right Way to Tax America | Office Hours

Why is the money that money makes more noble than the money that work makes? If there's any tax rate or a lower tax rate, it should be on people who actually show up and do the work to service us all as opposed to the people who sit behind a computer and trade their stocks on Robin Hood or hedge fund managers. And that might sound like class warfare, but it's not. It's Reagan. It's income is income.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

I think the biggest lesson I've learned is that the market is a discounting mechanism for the future, not the present. And what that means is that when things look the darkest, that's often when the best opportunities exist, and when things look the brightest, that's often when the risk is highest.

The Prof G Pod

Scott Galloway: Stop Demonizing Billionaires and Start Taxing them | Office Hours

AI's capex boom is the second largest share of use GDP in history. bigger than the railroads, second only to the I think the Louisiana purchase, and there's the build out of the electrical grid, the highway system, uh the Apollo program, although that wasn't very big, and then the internet and sort of the telco infrastructure.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

I think the most important lesson I've learned is that the ability to change your mind is probably one of the most important traits an investor can have. People confuse consistency and stubbornness, and they also are worried about how they look if they change their views.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

I've always thought of myself as a learning machine. The moment I think I know everything or I've seen everything or I've experienced everything, I become a worse investor. The best investors I know are voraciously curious and are always trying to update their models and their thinking.

The Prof G Pod

Scott Galloway: Stop Demonizing Billionaires and Start Taxing them | Office Hours

AI's capex boom is the second largest share of use GDP in history. bigger than the railroads, second only to the I think the Louisiana purchase... unlike past tech booms, Facebook, Instagram, Door Dash, it's fundamentally a supply side story about making chips, building data centers, and powering them. It's money creating demand for energy, not the reverse.

Compound Interest

Anthony Pompliano Thinks You're Smarter Than Your Financial Advisor

You can drastically outperform the advice coming from somebody whose job is to not get fired.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

I think there's a lot of conformity bias in investing and in life generally. If you look at most investment committees, most investment letters, most investment frameworks, they look the same. And I think that there's a reason for that — it's career protection. If you're wrong and you're wrong the way everyone else is wrong, then you're not singled out.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

What I find most interesting about Dan is how much his approach has evolved across thirty years. He came up as a credit and event-driven investor at Warburg Pincus and Jefferies, built Third Point, then layered in quality investing, thematic technology investing, and now a very large credit business that sits alongside the hedge fund.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

I think the most dangerous thing is to think that you've mastered the markets. The markets are going to teach you a lesson just when you get most confident. And so the most important thing is to maintain a kind of intellectual humility and a curiosity and to never stop learning.

The Prof G Pod

Should You Still Trust US Stocks? Scott Galloway's 20-Year Investing Playbook | Office Hours

If you were to bet exclusively on the US over the next 20 years, you're effectively betting on that the longest cycle in history just keeps going. There's been a recent reversal. In 2025, international equities gained 31% in dollar terms, outperforming US stocks by about um 15 percentage points, the biggest margin since 1993.

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

I think the most important thing in investing and in life is having the right temperament to deal with uncertainty and the unknown. Most people, when confronted with uncertainty or unknowing, they become fearful, and their decision-making is impaired. The best investors I know are actually energized by uncertainty because they see it as an opportunity.

Acquired

Vanguard: The communist capitalist who saved investors a trillion dollars (Audio)

I view Bogle as an undercover philanthropist. And at a trillion or even half a trillion dollars, that would make him the greatest philanthropist of all time.

The a16z Show

Why $1B Exits are Dead

today's AI companies are scaling faster than any previous generation of startups, and why the eventual outcomes may be significantly larger than most investors currently expect

Invest Like the Best with Patrick O'Shaughnessy

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

What I find most interesting about Dan is how much his approach has evolved across thirty years.

Invest Like the Best with Patrick O'Shaughnessy

Darren Farber on Iran, China, and the Rise of Neoprimes - [Invest Like the Best, EP.474]

We discuss why magazine depth matters for the American industrial base, lessons from Ukraine, and what the rise of neo-prime defense companies will require from Congress.

Throughline

Prediction markets are making a 150-year comeback | Throughline

And in several cases, there's evidence suggesting that the anonymous people who made these bets may have had insider information.

Acquired

Vanguard: The communist capitalist who saved investors a trillion dollars (Audio)

Jack Bogle and Vanguard are responsible for a trillion dollars of wealth transfer out of the pockets of Wall Street and the finance industry and into the pockets of individual investors in the form of fees that they didn't have to pay.

Compound Interest

Who Wants To Own Big Law?

Litigation finance is simply treating litigation claims as financial assets. You know, when you think about what litigation is, stepping back, it's just an effort for the most part to get money to move from one party to another.

Invest Like the Best with Patrick O'Shaughnessy

Paul Tudor Jones - Lessons From 50 Years in Markets - [Invest Like the Best, EP.469]

Trading is like a constant battle of risk management and patience, where he identifies the rare moments where he can take a truly big swing.

Prof G Pod

Scott Answers: Is AI Making Markets Crash-Proof? | Office Hours

If you think you're a stock picker, just keep in mind you're competing against an algorithm that looks at millions of points of data designed by a ton of PhDs making a lot of money all in a room who do nothing but try and pick up on signals. And you're watching CNBC or deciding because you see a long line outside of Chipotle that you're somehow informed on the markets.

Office Hours

Should You Still Be Trying to Own a Home? | Office Hours

Chasing home ownership for some sort of psychological benefit when it doesn't make any sense is not a great idea.

Prof G Conversations

Gary Stevenson: “Your Kids Will Be Poorer Than You” | Prof G Conversations

If you're Jeff Bezos, what is what's he worth? $300 million, $300 billion, right? Even if he makes 5% a year, right? Which he's going to make way more than that. Even if he makes 5% a year, he's making $15 billion a year, right? And it's just going to grow, right? It's going to grow unbelievably quickly.

Compound Interest

Wonder’s Marc Lore On Vibe-Coding Restaurants, Drone Delivery, & Becoming "The IPO Guy"

I've learned this lesson that anything fun, you know, in life, you usually lose money on until until sports.

The a16z Show

Crypto Fund 5: We Raised $2.2B. Here’s Why.

crypto has evolved from an ideological movement into a more pragmatic, product-focused ecosystem, shaped by real-world use cases and increasing regulatory clarity

Invest Like the Best with Patrick O'Shaughnessy

Paul Tudor Jones - Lessons From 50 Years in Markets - [Invest Like the Best, EP.469]

Trading is like boxing—you have to have a strong defense before you can think about offense, and most people want to be Mike Tyson before they can be Muhammad Ali.

TBPN

Mike Isaac (NYT) Joins, Earnings Review, Beautiful Data Centers, Coatue is Land Maxxing

Google search and other revenue was 6.4 billion. Yeah. Uh up 19% year-over-year. I mean two years ago there was the whole like Google search is dead thesis. Uh that has not been borne out at least this year.

Invest Like the Best with Patrick O'Shaughnessy

Paul Tudor Jones - Lessons From 50 Years in Markets - [Invest Like the Best, EP.469]

Trading is like boxing — you have to have your hands up, you have to be ready to move, and you have to understand that the moment you get hit, you need to get out of the ring and reassess.

Invest Like the Best with Patrick O'Shaughnessy

Paul Tudor Jones - Lessons From 50 Years in Markets - [Invest Like the Best, EP.469]

Trading is like boxing—you have to have a sustained ability to take a punch, and then know when to throw the big one.

Invest Like the Best with Patrick O'Shaughnessy

Alex Karnal - The Trillion-Dollar Health Revolution - [Invest Like the Best, EP.467]

most of the diseases that will claim most of our lives are already addressable with medicines that exist today

TBPN

SpaceX Financials, Chimpanzee Civil War, Self-Driving Safety, Ferrari

Investors who participate in the IPO will essentially be financing Musk's unproven AI ambitions in order to get a piece of uh high performing commercial space and telecom firm.

Prof G Markets

The Ceasefire Is Cracking — What Markets Are Missing | Prof G Markets

Earnings are holding up, but multiples were not. And to me that's really the story because you know if anything estimates have gone higher and you were getting you know the tech sector at the lowest multiple going back to 2022.