Invest Like the Best with Patrick O'Shaughnessy

Michael Moritz - Lessons From 40 Years of Investing and Writing - [Invest Like the Best, EP.491]

The venture capital business is one of the few endeavors where you can be wrong the vast majority of the time and still be considered successful. The reason is that the gains from the rare, extraordinary winner so thoroughly dwarf the losses from all the failures combined that the overall outcome can be spectacular.

Acquired

The Home Depot: The best-performing stock in the S&P 500 since IPO (Audio)

Home Depot went public in 1981, one year after Apple Computer. And astonishingly, if you put $1,000 into Home Depot and Apple and their IPOs and you held them all today, your investment in Home Depot would beat your investment in Apple. And if you reinvested the dividends that it paid out, it has compounded at nearly 25% per year for 45 years.

TED

Who Controls Your City’s Money? | Trinity Tran | TED

Money ultimately decides what gets built. Money decides what survives. Money decides what future becomes possible. So change where money goes and who controls it -- then you change what becomes possible.

Founders

#431 How Henry Singleton Worked

"Henry Singleton has the best operating and capital deployment record in American business. If one took the hundred top business school graduates and made a composite of their triumphs, their record would not be as good as Singleton's."

Invest Like the Best with Patrick O'Shaughnessy

Sarah Guo - What the 250 People Building AI Believe - [Invest Like the Best, EP.489]

At the center is Sarah's conviction that no single company will own the future of AI, and what that means for founders, investors, and anyone allocating their time and resources in a world moving this fast.

The a16z Show

Gavin Baker: Why AI Demand Is Outrunning Compute Supply

David explores whether the bigger near-term risk is not overbuilding, but failing to build enough.

Founders

#431 How Henry Singleton Worked

Henry Singleton has the best operating and capital deployment record in American business. If one took the hundred top business school graduates and made a composite of their triumphs, their record would not be as good as Singleton's.

Invest Like the Best with Patrick O'Shaughnessy

Neil Movva - Making AI 10x Cheaper - [Invest Like the Best, EP.488]

the premium the frontier labs charge for being three to six months ahead may not last

Invest Like the Best with Patrick O'Shaughnessy

Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486]

The best hardware companies look a lot like software companies in the way they think about software and the customer relationship, and the best software companies are starting to look a lot more like hardware companies in the sense that the physical world matters and the intersection of the two is where a lot of the most interesting things are happening.

Invest Like the Best with Patrick O'Shaughnessy

Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486]

The best companies we've invested in, the founders had a point of view about the world that was different from consensus, and they were right. And the hardest part of venture is that you can have a non-consensus view and be wrong, or you can have a consensus view and be right, but only the non-consensus and right leads to the outlier returns.

Invest Like the Best with Patrick O'Shaughnessy

Neil Movva - Making AI 10x Cheaper - [Invest Like the Best, EP.488]

The cost of running AI models has dropped roughly 10x per year for the past several years, which is faster than Moore's Law ever moved. If that rate continues, the things that are economically impossible to automate with AI today become possible very quickly.

Invest Like the Best with Patrick O'Shaughnessy

Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487]

The interesting thing about AI is that the returns are so uncertain. You could imagine a world where AI is transformative and these investments are the best ever made, or you could imagine a world where the returns never come and it's the biggest misallocation of capital in history.

The a16z Show

Martin Casado on Where the Value Is Going in AI

Martin believes this may be the biggest unlock of wealth he's seen since the 1990s.

Invest Like the Best with Patrick O'Shaughnessy

Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487]

why he thinks it would be dangerous for the United States to win the AI race outright, what container shipping and the railroads of the 1870s tell us about the buildout, and why the binding constraint on all of this may be capital rather than compute.

The Prof G Pod

“SpaceX Is a $10 Stock” | Office Hours

Musk will go down as the greatest engineer of our time, but as a financial engineer. He convinced the SEC and Trump and NASDAQ to include him in the 100, which no IPO has ever been included before, meaning trillions of dollars of funds are mandated to put whatever percentage of a weighted index that SpaceX represents, that amount of their capital into SpaceX shares. No company right out of the gates has enjoyed that incremental demand.

Book of the Day

'Cloudthief' and 'Dead but Dreaming of Electric Sheep' are novels that center tech

The most valuable thing in the world is no longer money, you know, or jewels, or artwork. It's data. And all of this data lives in these Fort Knoxes that no one really talked about called data centers.

Diet TBPN

North Korea’s Secret US Workforce, Canceling the SaaSpocalypse, MSL’s Latest Exits | Diet TBPN

There were a lot of companies that were getting thrown in the SAS bucket as just like a pure pile of code. You could vibe code it. Uh and while that thesis might play out over a few years, it's it was a little bit too soon. it seemed a little bit too aggressive

The Prof G Pod

Scott Galloway: Why I Moved to Europe | Office Hours

When you're in your income earning years, I find the US is still the best place. People in the US start from a position of yes. How do we how do we make money together? How do we do stuff together? And Europe is the best place to spend it.

Diet TBPN

Nvidia’s $500B Compute Deal, Paramount Threatens CA Exit, Musk’s Shortcut to $1T Payday | Diet TBPN

AI tokens are profitable incredibly profitable. When you have something profitable, everybody wants to make more of it. Great demand, great profitability. The conditions are exactly right for the work that we're doing right now.

Invest Like the Best with Patrick O'Shaughnessy

Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486]

What makes him special is his ability to use that history to make sense of today.

Invest Like the Best with Patrick O'Shaughnessy

Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486]

The best hardware companies are ones where the software is so differentiated that the hardware almost doesn't matter, but you need the hardware to run the software. And the worst hardware companies are ones where the hardware is the product, and they're trying to figure out the software later.

The Week

The Week: How Leverage Broke the AI Trade

The fraud cycle follows the financial cycle with a lag. And the longer the financial cycle goes on, the more amount of fraud is ultimately uncovered on the down cycle. The harshest prosecutor and the staunchest defense attorney of a company is its stock price. Nobody goes after frauds at all-time highs.

Invest Like the Best with Patrick O'Shaughnessy

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

The bears say inference is a commodity and that we'll see severe margin compression. I think that's probably right in aggregate, but I think that also misses what happened in the cloud. Amazon and Microsoft and Google do sell compute as a commodity, but they make enormous profits doing so, because commodities at massive scale with high fixed costs and low variable costs can be very, very profitable businesses.

Invest Like the Best with Patrick O'Shaughnessy

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

The most underappreciated thing about AI is that it's deflationary. Every single time in history when something has caused the kind of growth in demand that AI is causing, it has been because it is deflationary — because it lowers the cost of doing something that people want to do.

The Week

The Week: How Leverage Broke the AI Trade

The fraud cycle follows the financial cycle with a lag. And the longer the financial cycle goes on, the more amount of fraud is ultimately uncovered on the down cycle. So, I've already dubbed this the golden age of fraud. And I suspect that when we're on the down part of this cycle, the bodies will float to the surface as they always do.

Invest Like the Best with Patrick O'Shaughnessy

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

The street is now generally assuming that hyperscalers are going to spend somewhere between $300-325 billion in capex in 2025. And these are numbers that were literally unimaginable 2 years ago. The question is what is the ROI on that spend and what is the right mental model for thinking about it.

Invest Like the Best with Patrick O'Shaughnessy

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

The most dangerous words in investing might be 'this time is different,' but the second most dangerous might be 'this time is the same.' Almost every major technology transition has seen people underestimate the ultimate scale of the winning technology while simultaneously overestimating the near-term pace of adoption and monetization.

Invest Like the Best with Patrick O'Shaughnessy

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

The most important thing I would say is that I think AI is the most important technology in human history, bar none. More important than the printing press, more important than electricity, more important than the internet. The reason I say that is it's the first technology that can potentially augment or replace human cognitive labor at scale.

The Prof G Pod

Scott Galloway: Health Insurance Is a Scam | Office Hours

The way to wealth isn't making a lot of money. It's making more than you spend. My father died a near millionaire and he never made more than or you know he was making $48,000 a year but he spent 46 or 45 and he was investing and saving money even when he died.

Invest Like the Best with Patrick O'Shaughnessy

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

The most important thing about AI is that it's deflationary for everything except compute and energy. This is very counterintuitive because people assume that a massive new technology wave is going to be inflationary. But AI is fundamentally deflationary for almost everything except the things needed to build and run AI.

Invest Like the Best with Patrick O'Shaughnessy

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

The history of technology tells us that the companies that win in a new technology paradigm are often not the companies that won in the previous technology paradigm. And I think that's a really important thing to keep in mind when you're thinking about AI.

The Prof G Pod

Should You Sell Your Stocks Right Now? | Office Hours

One of the greatest wealth hacks in history is the ability to buy equities and let them compound tax deferred. And then if you want to do the trick of billionaires, if you need cash to fund your lifestyle, maybe you borrow against those stocks, not more than say 20 30 40% at max to fund your lifestyle

TBPN

Martin Shkreli Breaks Down the Collapse of Situational Awareness

The smart guys get in early, start buying, see the prices go up, buy some more. And then less smart guys take note and say, I want to do that. I want to be up 400% this year, too. And then but by the weakest hands are buying at the top. So they're also the first to sell. The first to panic. And it just creates this like, you know, every bubble's sort of the same. You have this euphoria, this peak, and then, you know, everyone sort of panics at once.

Pivot

Kara Swisher Calls It Now: the Paramount Merger Won’t Go Through | Pivot

Investors understand something executives often don't, and that is winning in court can still mean losing economically.

TBPN

Leopold is Back! Big Tech Earnings, Beautiful Debt, Defense Tech Deep Dive

But our fund must always be structured such that we can take a loss and fight another day.

Diet TBPN

Leopold Stays in the Game, Big Tech Earnings, OpenAI Slashes GPT-5.6 Prices | Diet TBPN

When AI stocks draw down dramatically while AI technical business fundamentals are improving, you should expect our fund to be down a lot. We embrace volatility, but it should never jeopardize the fund.

The Week

The Week: The Hidden Debt Behind the AI Boom

When you're hiding a bigger number than what you're reporting, that's not accounting, it's concealment. And Meta's off-balance debt is $420 billion, which is 3x what they report. That's not a rounding error, that's a second company hiding liabilities inside of the first company.

TBPN

Martin Shkreli Breaks Down the Collapse of Situational Awareness

The 80 or 90% of the assets shareholders don't change hands. It's that 5% of the margin that's deciding the price. And if that 5% is in the state where they're they're levered up 3x or 4x as we heard uh SALP is uh was a 4x levered fund, which is that's a lot of leverage. You know, a 25% draw down takes you out of business.

Diet TBPN

The Collapse of Situational Awareness, Ferrari Luce Stays on Track for 2026 | Diet TBPN

When leverage is involved, things just move so so so fast, right? You remember with FTX, there's kind of some rumblings, a couple couple posts from SPF saying like we're fine, it's all good, and then it was over. And then the same thing with SVB, like couple rumblings, maybe like a a couple weeks, a week beforehand, few posts here and there, and then it just moves so so fast, right? quite a bit different than traditional venture world where when a company's dying it dies over two, three years often sometimes more.

The Prof G Pod

The Simple Math That Tells You When You're Rich Enough | Office Hours

The whole point of wealth at the end of the day is somebody has to spend it on something. Whether it's you, your kids, you give it away to like a philanthropic organization to spend. And having like a scarcity mindset where you're constantly worried about not having enough even when you objectively have enough is just depriving yourself of things you could spend money on to enjoy.

Invest Like the Best with Patrick O'Shaughnessy

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

The US is entering a period where natural gas demand is set to explode — driven by AI data centers, LNG export terminals, and industrial reshoring — but the pipeline infrastructure to move that gas simply hasn't been built. The bottleneck isn't the gas itself; it's the ability to get it from where it's produced to where it's needed.

Pivot

Andrew Tate and Brother Charged with New Sex Crimes. "It's Epstein in Real Time" | Pivot

Trump came in and said you guys are amateurs. I'm going to make millions not thousands... she had access to material non-public information but she didn't start a wire service selling her inside information right to others.

Invest Like the Best with Patrick O'Shaughnessy

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

The U.S. is facing a situation where natural gas has become the critical bottleneck for economic growth — not oil, not renewables, but gas. The buildout of data centers, the reshoring of manufacturing, and the electrification of everything are all converging on the same fuel at the same time, and the infrastructure to deliver it simply isn't there yet.

Invest Like the Best with Patrick O'Shaughnessy

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

The US is going to be consuming a lot more natural gas going forward, and the infrastructure to deliver that gas is going to be a bottleneck. You're going to need more pipelines, more LNG export terminals, more storage. The question is whether the capital investment can keep up with the demand growth.

Invest Like the Best with Patrick O'Shaughnessy

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

The United States is in the middle of an energy transformation, and natural gas sits at the center of it. The same fuel that was supposed to be a bridge to renewables is now being called upon to power the AI revolution, sustain manufacturing reshoring, and keep the lights on as coal retires faster than alternatives can replace it.

Invest Like the Best with Patrick O'Shaughnessy

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

The United States is on the verge of a natural gas shortage so severe that it could undermine the AI boom, strain the electric grid, and trigger the kind of energy crisis that Americans haven't experienced in decades.

Invest Like the Best with Patrick O'Shaughnessy

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

The issue is that the natural gas pipeline system wasn't built for what we're now asking it to do. You've got LNG export facilities pulling massive volumes to the Gulf Coast, data centers and AI infrastructure demanding firm power in places that never needed it before, and a renewables buildout that paradoxically increases gas demand by requiring backup generation for when the wind doesn't blow and the sun doesn't shine.

Invest Like the Best with Patrick O'Shaughnessy

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

Starting in 2028, AI data centers and LNG exports will need more gas than the country can produce and deliver. By his math, the US could exhaust its working natural gas storage by 2030. In his words, the upside risk to prices becomes unbounded and convex.

Pivot

Andrew Tate and Brother Charged with New Sex Crimes. "It's Epstein in Real Time" | Pivot

When you have this much money wagered on matches, they're no longer it's no longer a gambling story. It's a capital market story.