Tag: investing

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Friends Gratitude Kindness Living

The One Thing Money Doesn’t Buy

Somewhere there is a couch that launched a hedge fund.

It belonged to a man named Carter, and for the better part of a year it was where Dan Loeb slept while he figured out what came next. No office. No fund. No Third Point. Just a friend’s apartment and the specific grace of someone who didn’t need you to have already become something before they let you in the door.

When Loeb finally landed at Jefferies, Carter gave him a few hundred thousand dollars to manage. That became a million. The million became seed capital. Third Point was built on top of it — thirty years of it, billions of dollars of it — and all of it traces back, in some straight unbroken line, to a couch and a person who said yes before the evidence was in.

Patrick O’Shaughnessy asked him about it near the end of a long conversation. The kindest thing anyone has ever done for you — it’s the question O’Shaughnessy always asks, and it always cuts through. Loeb had just finished making a case for kindness as a serious value, not a soft one. Something that belongs at the top of the hierarchy, he said, next to honesty and intelligence. The mechanism that unlocks empathy. He noted, almost reluctantly, that it also compounds in business — before adding that the moment you start treating it as an investment, you’ve already lost the thread.

Then he quoted Palmer Luckey.

The one thing money doesn’t buy you is friends that believed in you when you had nothing.

Luckey built Oculus in his parents’ garage. Sold it for two billion. Founded Anduril. He has spent his adult life proving that if you are relentless and strange and right, you can make almost anything happen with money. And what he noticed, somewhere in all of that, is where money stops. Not at luxury. Not at access. It stops at loyalty that predates your success. You cannot purchase the memory of Carter’s couch. You cannot acquire, at any price, the specific knowledge that someone held you when you were nothing yet.

I have been thinking about the people in my own life who did some version of this. Not always with money. A call made on your behalf before you knew you needed it. A door held open to a room you couldn’t see. These moments are nearly invisible when they happen. They only become legible later, once the room turns out to matter — once you can look back and trace the line.

The line is always shorter than you think. And it always ends at a person.

Categories
AI

The Coach Who Wouldn’t Change

In 1975, a twenty-four-year-old Kodak engineer named Steve Sasson built the first digital camera. It was the size of a toaster, captured a black-and-white image at 0.01 megapixels, and took twenty-three seconds to record a single photograph to a cassette tape. Sasson showed it to his managers. Their response, as he later recalled, was essentially: that’s cute, but don’t tell anyone about it.

Kodak was not a stupid company. It was a dominant one. At its peak it held 90 percent of the American film market and 85 percent of camera sales. Film was not just a product line — it was the entire economic architecture of the company. Processing fees, paper, chemicals, the retail relationships built around the assumption that photographs needed to be developed. Digital threatened all of it simultaneously. So Kodak did what dominant companies do when confronted with a threat they can’t absorb into the existing model: they managed it. They ran studies. They filed patents. They made incremental moves. They protected the thing that was working rather than building the thing that would work next.

Kodak filed for bankruptcy in 2012. The digital camera had been sitting in their own archives for thirty-seven years.

Nokia’s version of the same story has a different texture. Where Kodak’s failure was about protecting a margin, Nokia’s was about identity. Through the 1990s and into the early 2000s, Nokia was mobile phones — not a major player, but the category itself. At its peak it held over 40 percent of the global handset market. The company had navigated a remarkable transformation earlier in its history, shedding paper mills and rubber boots to become a pure technology company. It knew how to change. It had done it before.

What it couldn’t do was change from a hardware company into a software one. When the iPhone arrived in 2007, Nokia’s internal assessments were, by most accounts, accurate. They understood the threat. They had touchscreen prototypes in development. What they couldn’t manage was the cultural distance between building phones that were superb physical objects — durable, reliable, made to exacting standards — and building phones that were primarily platforms for software that other people would write. The excellence that had made Nokia great was manufacturing excellence. The game was becoming something else, and manufacturing excellence was not only insufficient for the new game; it was actively in the way, because it oriented every decision toward the object rather than the experience.

Nokia’s market share collapsed from over 40 percent in 2007 to under 5 percent by 2013.

Andy Grove, who built Intel into the dominant force in semiconductors, called it plainly: only the paranoid survive. He meant it as a prescription. His successors treated it as a trophy.

Both stories have the clean shape of settled history. We know how they end. The verdict is in, the lesson is available, and it’s easy to read them now as cautionary tales about obvious mistakes made by people who should have known better.

This is the wrong way to read them.

Kodak and Nokia didn’t fail because they were blind. They failed because they were standing on a fulcrum — a moment when the old game and the new game were both plausibly real — and they chose the wrong side. At the time, that choice was not obviously wrong. Film was still enormously profitable. Nokia’s hardware was genuinely superior. The rational case for staying the course was real, and the people making it were not fools.

The reason the Kodak story is still told fifty years later is not that the mistake was obvious. It’s that it wasn’t — and they made it anyway.

Which brings us to now. Because there is a fulcrum in front of the enterprise software industry, and nobody knows yet which way it tips.

The companies in question — Salesforce, ServiceNow, and most of the SaaS category built over the last twenty years — were constructed on a simple and powerful premise: that businesses would pay recurring subscription fees for software that managed their customer relationships, their workflows, their data. The premise was correct. It produced some of the most durable businesses in the history of technology.

The threat AI poses to this model is not subtle. If an AI agent can handle a customer service interaction, manage a workflow, or synthesize a CRM record without a human touching licensed software to do it, then the per-seat subscription model — the economic engine underneath all of it — starts to look like film processing in 2003. Theoretically intact. Quietly at risk.

The responses of these companies have been instructive, and they’ve diverged.

Here is the honest position: we don’t know yet. The fulcrum is still in motion.

It’s possible that Salesforce’s Agentforce is the Kodak digital camera — the real thing, built by the right company, that gets buried under the weight of protecting what already works. It’s possible that the SaaS model is more durable than the threat suggests, that enterprises will pay for trusted platforms regardless of the underlying labor model, and that the companies racing hardest to cannibalize their own revenue streams are making a different kind of mistake. It’s possible that ServiceNow’s consistency is discipline, or that it’s the Nokia instinct to keep building the best version of the thing that used to win.

What the Kodak and Nokia stories actually teach — not the simplified version, but the harder one — is that the mistake is never visible in the moment it’s made. It only becomes visible later, when the fulcrum has tipped and the choice that was once defensible has become permanent.

The coach who wins five championships holds the philosophy and rotates the players. The coach who wins one holds the players and calls it philosophy.

The enterprise software companies standing at this moment have a version of the same decision. The ones who make it correctly will, in twenty years, be the ones we cite as examples of adaptation. The ones who don’t will be the ones we cite as examples of something else.

We just don’t know yet which is which. That’s not a comfortable place to stand. It is, however, exactly where we are.

Categories
AI Business

The Topography of a Face

I found myself staring at the physical geometry of a conversation the other day—not the words, but the topography of the faces delivering them.

Elad Gil recently shared a fascinating experiment during a conversation with Tim Ferriss. He’s been uploading photos of startup founders into AI models and asking the machines to predict if they’d be successful, purely based on their “micro-features.”

“Because if you think about it, we do this all the time when we meet people, right? We quickly try to create an assessment of that person, their personality, and what they’re like. There are all these micro-features—like, do you have crow’s feet by your eyes, which suggests that your smiles are genuine? […] So, I have this whole set of prompts that I’ve been messing around with, just for fun, around: ‘Can you extrapolate a person’s personality based off of a few images?'”

He notes the model breaks down the crow’s feet and the furrowed brows, extrapolating a personality from a static frame. It’s a parlor trick, perhaps. But it works because it holds a mirror to our oldest, most unexamined instinct.

We are all amateur phrenologists of the human face. We sit across a table, measure the crinkle of an eye or the tightness of a jaw, and we build a rapid, invisible architecture of trust or suspicion. Over decades of investing and making career choices, I’ve often leaned heavily on this silent language. I’ve backed founders because their intensity felt genuine, and I’ve passed on others because something in their posture felt misaligned.

But if I am brutally honest, that intuition has sometimes been a mask for my own blind spots. I’ve held on to failing investments for far too long because I trusted a reassuring smile. We like to think our gut instinct is a sophisticated instrument. Often, it is just a pattern-matching engine running on deeply flawed historical data.

Now, we are handing that very human habit over to a machine. We prompt the AI to become a “cold reader,” and it obliges, predicting who will be the quiet observer and who will deliver the dry wit.

The unsettling part isn’t that the machine might get it wrong. The unsettling part is that it might get it exactly right—by mimicking the very same rapid, superficial judgments we make every day, just at a terrifying scale.

We are teaching silicon to read the human code. The future will belong to those who realize the code was always written in our own biases.

Categories
Aging Financial Planning Living Taxes

Borrowing from Tomorrow: The Paradox of the Modern 401(k)

A retirement account is, at its core, a financial time machine. It is a profound act of optimism and delayed gratification, a quiet promise made by our present selves to ensure the security of our future selves.

We lock away a portion of our labor today, trusting that time and compounding interest will nurture it into a safety net for tomorrow.

But what happens when tomorrow’s safety net becomes today’s desperate lifeline?

According to a recent piece by Anne Tergesen in the Wall Street Journal, reviewing Vanguard’s “How America Saves 2026” report, we are currently living through a profound financial paradox. On one hand, the machinery of wealth building is working better than ever. The average 401(k) balance rose 13% in 2025 to a record $167,970. Thanks to automatic enrollment—which now encompasses 61% of plans—more people are participating and escalating their contributions than at any point in history.

Yet, hidden beneath these soaring averages is a quiet, parallel crisis.

In 2025, a record 6% of workers in Vanguard-administered plans took a hardship withdrawal. This is roughly double the pre-pandemic average. We are witnessing the stark reality of a “K-shaped” economy in real-time: a broad swath of the population is riding the upward arm of the “K” into financial security, while a growing minority is sliding down the bottom arm, facing acute financial stress.

The most telling, and perhaps the most heartbreaking, statistic in the report is the median withdrawal amount: just $1,900.

These are not individuals cashing out their life savings to fund frivolous luxuries. A $1,900 hardship withdrawal—subject to income taxes and a brutal 10% early-withdrawal penalty for those under 59½—is an act of absolute necessity. It is the exact cost of avoiding an eviction notice. It is the price of keeping the lights on, of covering a sudden medical expense, or of preventing a cascade of debt from pulling a family under. It is the cost of survival.

Recent policy changes have fundamentally altered the psychology and accessibility of the 401(k). The removal of the requirement to take a loan first, combined with new exemptions for domestic abuse victims, disaster relief, and penalty-free emergency withdrawals, has transformed the traditional retirement lockbox into a de facto checking account for emergencies.

From a purely mathematical standpoint, raiding a retirement account is a tragedy of lost potential. It interrupts the magic of compound growth and cannibalizes the future to feed the present. But from a human standpoint, it is difficult to judge. How can we ask someone to prioritize their 65-year-old self when their 35-year-old self is facing foreclosure?

David Stinnett of Vanguard offers a vital, empathetic reframe of this data. Because of automatic enrollment, he notes, “People are saving more, remaining invested, and being automatically rebalanced in a professional way.” This systemic forced-savings mechanism has created a financial cushion for millions of people who previously had none. Yes, it is heartbreaking that they are forced to use it. But the silver lining is that the money is actually there to be used.

This trend forces us to ask deep, philosophical questions about the modern American economy. If our total savings look so strong on paper, yet so many must still routinely puncture their life rafts just to stay afloat, what does that say about the cost of living, housing, and healthcare?

A 401(k) was designed to be a bridge to a peaceful retirement. Today, for an increasing number of Americans, it is the only bridge across the turbulent waters of the present. As we celebrate record-high balances, we must not look away from the $1,900 lifelines being thrown out every day.

The future is only guaranteed for those who can afford to survive the present.

Categories
Investing Living

The Lonely Quadrant: Why the Crowd Never Outperforms

There is a profound comfort in the consensus. When we agree with the crowd, we are protected by a shared canopy of logic. If we are wrong, we are wrong together. The sting of failure is diluted by the sheer number of people who made the exact same miscalculation. We can shrug our shoulders, look at our peers, and say, “Who could have known?”

But this comfort comes at a steep price: mediocrity.

Years ago, the legendary investor Howard Marks crystallized a framework that has haunted my thinking ever since. He mapped out the relationship between predictions and outcomes, arriving at a blunt, inescapable truth about generating extraordinary results. To make really good money—or to achieve outsized success in almost any competitive endeavor—you cannot simply be right. You have to be right when everyone else is wrong.

“You can’t do the same things others do and expect to outperform.”

Marks’ logic is beautifully ruthless. If your prediction aligns with the consensus and you are right, the rewards are merely average. The market, or the world, has already anticipated and priced in that outcome. There is no edge in seeing what everyone else sees. If your consensus prediction is wrong, you lose, but you lose alongside the herd.

The danger, and the opportunity, lies in the contrarian view.

If you are non-consensus and wrong, you look like a fool. You bear the entirety of the failure alone, stripped of the insulation of the crowd. This is the quadrant of public mockery, isolated defeat, and bruised egos. It is the fear of this quadrant that keeps most people safely tucked inside the consensus.

But the magic—the life-changing returns, the paradigm-shifting innovations, the profound personal breakthroughs—lives exclusively in the final quadrant: being non-consensus and right.

This isn’t just an investing principle; it’s a philosophy for navigating life. We are biologically wired to seek the safety of the herd. To step outside of it requires not just immense intellectual conviction, but a formidable emotional threshold. You have to be willing to sit with the discomfort of being misunderstood, sometimes for years. You have to endure the sympathetic smiles of peers who think you’ve lost the plot.

Creating truly great art, building a lasting company, or making an exceptional investment demands a willingness to be lonely in your convictions. It requires looking at the exact same data as everyone else and seeing a completely different narrative.

However, a vital caveat remains: being different isn’t enough. There are plenty of contrarians who are simply wrong, confusing blind rebellion with profound insight. The goal isn’t to be a contrarian for the sake of being difficult or edgy. The goal is to perceive a truth the crowd has missed.

It is a quiet, solitary bet against the world’s prevailing wisdom. And when the world finally catches up to where you have been standing all along, the reward is entirely yours.

Categories
AI

The Student, The Teacher, and the Delightful Absurdity of It All

Howard Marks is one of the sharpest financial minds alive. The man has been thinking clearly about markets for fifty years, has written memos that get passed around Wall Street like sacred texts, and has outlasted more market cycles than most of us have had hot dinners. So when Howard Marks decides he needs to get educated about artificial intelligence to write a follow-up to his December memo, he does what any serious intellectual would do: he asks Claude.

And then Claude — the AI — teaches him about Claude.

I’ve been sitting with this for a few days and I’m still not entirely sure whether it’s profound or just very, very funny. Maybe both. Probably both.

Continue reading “The Student, The Teacher, and the Delightful Absurdity of It All”
Categories
AI

A Distinction Without a Difference

We have long found comfort in a specific boundary: machines calculate, humans create. We think of computers as vast, unfeeling filing cabinets made of silicon—useful for retrieval, but entirely incapable of revelation. But what happens when the cabinet begins to read its own files, connects the disparate threads, and hands you a synthesized philosophy of the world? What happens when it speaks to you not as a database, but as a peer?

Howard Marks, the legendary co-founder of Oaktree Capital and author of deeply revered investment memos, recently stood at this very threshold. In his newest piece, “AI Hurtles Ahead,” Marks recounts an experience that left him in a state of “awe.” He tasked Anthropic’s Claude with building a curriculum to explain the recent, breakneck advancements in artificial intelligence. Instead of regurgitating a dry, encyclopedic summary, the AI delivered a personalized narrative. It utilized Marks’s own historical frameworks—his famous pendulum of investor psychology, his observations on interest rates—and wove them into its explanations. It argued logically, anticipated counterpoints, and displayed an eerie sense of judgment.

Marks leans into the philosophical crux of this moment. He asks the question that keeps knowledge workers awake at night: Can AI actually think? Can it break genuinely new ground, or is it just remixing existing data? Skeptics often dismiss AI as a brilliant mimic—a “statistical recombination” engine that serves as a highly talented cover band, but never the original composer.

Yet, when presented with this skepticism, the AI offered a rejoinder to Marks that is as profound as it is humbling. It pointed out that everything Marks knows about investing came from someone else. He learned the margin of safety from Benjamin Graham, quality from Warren Buffett, and mental models from Charlie Munger.

“The raw material came from others. The synthesis was yours,” the AI noted, challenging the barrier between biological learning and machine training. “The question isn’t where the inputs came from. The question is whether the system—human or artificial—can combine them in ways that are genuinely novel and useful.”

This exchange strikes at the very core of the human ego. For centuries, we have fiercely guarded the concepts of “creativity” and “intuition” as uniquely, immutably ours. But if thinking is merely the absorption of prior inputs applied thoughtfully to novel situations, then our monopoly on cognition may be coming to an end.

Marks highlights that we are no longer dealing with simple assistance tools (Level 2 AI); we have crossed the Rubicon into the era of autonomous agents (Level 3). He cites the sobering reality of the current tech landscape, where the newest models are literally being used to debug and write the code for their own subsequent versions. The machine is building the machine. It is no longer just saving us execution time—it is replacing thinking time. As Matt Shumer aptly described the sensation, it’s not like a light switch flipping on; it’s the sudden realization that the water has been rising silently, and is now at your chest.

We can endlessly debate the semantics of consciousness. We can argue whether a neural network “truly” understands the weight of the words it generates, or if it is merely predicting the next token in a sequence with mathematical precision. But as Marks so astutely points out, this might be a distinction without a difference.

The economic and societal reality is that the work is being done. As we hurtle forward into this new era, the most pressing question isn’t whether machines can truly think like humans. The question is: who will we become, and what new frontiers will we choose to explore, now that the heavy lifting of cognition is no longer ours alone to bear?

Categories
AI Business

The Moat Drains

There is an old metaphor in investing — the “moat.” Warren Buffett popularized it: the idea that the best businesses are castles surrounded by deep, wide moats that keep competitors at bay.

For the past two decades, enterprise software companies built some of the most impressive moats in the history of capitalism. Sticky customers. Multi-year contracts. Switching costs so high that even dissatisfied clients stayed put. The moat wasn’t just deep — it was filled with concrete.

This morning, JP Morgan’s equity research team quietly suggested the concrete may be cracking. See also this recent Substack post by Jordi Visser.

In a note lowering price targets across their software coverage, the bank cited a striking phrase: “the exponential pace of AI proliferation raises doubts about competitive moats and the defensibility of software companies.”

They’re not alone in thinking this. But there’s something significant about seeing it written in the careful, hedged language of a major Wall Street research report.

When the analysts who model ten-year discounted cash flows start abandoning that framework — replacing it with simpler one- and two-year profitability multiples — it’s a signal worth decoding.

The shift in valuation methodology is itself the story. DCF analysis — the gold standard of software valuation for a generation — requires confidence in a company’s earnings trajectory over many years.

JP Morgan is saying, plainly, that they no longer have that confidence. The window of visibility has collapsed. When you can’t see more than a year or two out, you stop pretending you can.

“Investors are less comfortable underwriting defensive growth over multi-year periods.”

What’s driving this?

The suspicion — increasingly well-founded — that AI is not just a feature to be added to existing software products, but a force that restructures the value chain entirely.

If an AI agent can perform the function that previously required a $50,000-per-year SaaS subscription, the moat doesn’t just shrink. It evaporates. The castle becomes a historical curiosity.

Vertical software stocks — the specialized platforms serving specific industries like healthcare, construction, or legal — currently trade at 10 to 25 times EBITDA, according to the note. The S&P 500 as a whole trades at 15 times. The message embedded in those numbers is sobering: many of these once-premium businesses are being re-rated toward commodity valuations, and some may not have found their floor yet.

JP Morgan’s preferred companies in this environment are those with upside to 2026 revenue estimates and those they view as “defensive to AI proliferation.” That second phrase is the one I find myself turning over. It implies a new taxonomy is forming in the market — not growth vs. value, not cyclical vs. defensive, but AI-vulnerable vs. AI-resistant. That’s a categorization that didn’t meaningfully exist three years ago.

The moat metaphor may need an update. In the age of AI, the question is no longer how wide the moat is. It’s whether the castle itself still needs to exist.

Questions to Consider

  1. The Moat Inventory: If you were a software CEO this morning, which parts of your product would you genuinely consider defensible against AI substitution — and which would you privately admit are vulnerable?
  2. The Valuation Signal: When Wall Street abandons long-term DCF models in favor of near-term multiples, is that a temporary adjustment to uncertainty — or a permanent reset in how software businesses will be valued going forward?
  3. The New Taxonomy: JP Morgan implicitly divides the software world into AI-vulnerable and AI-resistant. What characteristics do you think actually define that divide — and can a company move from one category to the other?
  4. The Buffett Test: Buffett’s moat metaphor was built for a world of slow-moving competitive forces. Is the concept still useful in an era of exponential technology change, or do we need a new mental model entirely?
  5. The Timing Question: Is this re-rating of software companies a rational early response to a real structural shift — or is Wall Street, as it often does, overcorrecting in the short term for a change that will take much longer to fully materialize?
Categories
AI AI: Large Language Models Investing

From Ink to Insight

There is a distinct friction that exists between the analog world and the digital one. For years, analog notebooks have been the graveyard of good intentions—lists of books to read, article ideas to write, and companies to investigate, all trapped in the amber of my barely legible handwriting.

I recently found myself looking at one of these lists: a scrawl of company names I had jotted down while reading an article discussing possible companies for investment in 2026. Usually, this is where the work begins—taking my handwritten notes, typing them out one by one, searching for tickers, opening tabs, etc. It is low-value administrative work that often kills any spark of curiosity before it can turn into useful analysis.

“The barrier to entry for deep research drops to the time it takes to snap a photo.”

On a whim, I snapped a photo and uploaded it to Gemini 3 Pro. “Transcribe this,” I asked. “Give me the tickers.”

I expected errors. My handwriting is, to put it mildly, not easy to read (even for me!).

Instead, the AI didn’t just perform Optical Character Recognition (OCR); it performed contextual recognition. It understood that the scribble resembling “Apl” in a list of businesses was likely Apple, and returned $AAPL. It deciphered the intent behind the ink.

But the real shift happened when I asked Gemini to pivot immediately into research. Within seconds, I went from a static piece of paper to a dynamic analysis of P/E ratios, recent news, and market sentiment. The friction was gone.

This experience wasn’t just about productivity; it was about the fluidity of thought. We are moving toward a reality where the interface between the physical world and digital intelligence is becoming permeable. When the barrier to entry for deep research drops to the time it takes to snap a photo, our curiosity is no longer limited by our patience for data entry. We are free to simply think.

Categories
Financial Planning Investing

The Mistake of Balance

We are culturally conditioned to hedge. We are taught the virtues of a balanced portfolio, a balanced diet, and a balanced life. We spread our chips across the table—a little bit of energy here, a little bit of time there—hoping that if we just cover enough bases, the aggregate sum of our efforts will amount to a meaningful existence. We find comfort in the average because it protects us from the zero.

But nature, and certainly the mechanics of outsized success, rarely operates on a bell curve. It operates on a Power Law.

Sam Altman, reflecting on the errors of intuition in investing, noted that his second biggest mistake was failing to internalize this mathematical reality. He said:

“The power law means that your single best investment will be worth more to you in return than the rest of your investments put together. Your second best will be better than three through infinity put together. This is like a deeply true thing that most investors find, and this is so counterintuitive that it means almost everyone invests the wrong way.”

The math is brutal in its clarity. It suggests that the drop-off from our primary point of leverage to everything else is not a gentle slope; it is a cliff.

When we apply this to capital, it makes sense. One Google or one Stripe returns the fund. But this is a “deeply true thing” that transcends venture capital. It applies to our attention, our relationships, and our creative output.

Consider the “investments” of your daily energy. Most of us spend our days in the “three through infinity” zone. We answer emails, we manage low-leverage maintenance tasks, we entertain lukewarm acquaintanceships. We busy ourselves with the long tail of distribution because the long tail is where safety lives. It feels productive to check fifty small boxes.

However, if Altman’s observation holds true for life as it does for equity, then that single, terrifyingly important project—the one you are likely procrastinating on because it feels too big—is worth more than the rest of your to-do list combined.

The “counterintuitive” pain point Altman mentions is that to align with the Power Law, you have to be willing to look irresponsible to the outside observer. You have to neglect the “three through infinity.” You have to let small fires burn so that you can pour all your fuel onto the one flame that actually matters.

We invest the wrong way because we are afraid of the volatility of focus. We dilute our potential because we are terrified that if we bet on the “single best,” and it fails, we are left with nothing. But the inverse is the quiet tragedy of the modern age: we succeed at a thousand things that don’t matter, missing the one thing that would have outweighed them all.