Tag: SaaS

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Aging AI Business Living

The Being Phase

There is a metric making the rounds in technology investing circles that is, on its face, about market share and revenue concentration. Alex Sacerdote of Whale Rock Capital calls it the New Rule of 40 for AI. The formula is simple: take the percentage of a company’s sales derived from AI, add its percentage market share in that AI category, and if the sum reaches 40, you have a winner. Celestica, a company most people have never heard of, scores extraordinarily well. It owns somewhere between half and sixty percent of the cloud Ethernet white-box switch market. NVIDIA doesn’t need a formula. It simply is what it is.

Sacerdote designed the metric to cut through a specific kind of noise — the companies claiming AI exposure they don’t actually have, the giants whose AI revenue hovers at one or two percent of their base while their press releases suggest otherwise. The framework is a detector. It finds the companies that have stopped becoming AI infrastructure and started simply being it.

I found myself less interested in the companies than in that distinction.

I spent years at Visa watching a network that had long since crossed that threshold. By the time I arrived, Visa wasn’t becoming the global payments infrastructure. It was the global payments infrastructure. The work was real — fraud detection, modeling, the daily labor of keeping something enormous running — but the existential question had been settled before I got there. The network existed. Merchants accepted it because cardholders carried it. Cardholders carried it because merchants accepted it. That loop had been closing for decades. We were custodians of a fait accompli.

There’s a particular feeling to working inside something that has already won. It’s not complacency exactly. The problems are genuine and the stakes are high. But the uncertainty has a different quality — it’s operational uncertainty, not existential uncertainty. You’re not asking whether the thing will survive. You’re asking how to run it well.

I didn’t have language for that distinction then. Sacerdote’s metric gives me some. The companies that score highest on his New Rule of 40 have resolved their existential question. They’re not fighting for position. They’re administering a position already held.

The question that has followed me out of that career, and out of several decades of watching technology cycles turn, is simpler and more personal than any investment framework.

When did I cross that line myself?

I have been writing at sjl.us since 2001. That’s not a boast — it’s a data point. Twenty-five years of thinking out loud, of ideas arriving rather than being argued, of the specific memory as structural anchor. The blog is not becoming anything. It is what it is: a record of a mind moving through time, accumulated into something that has its own weight and shape.

The book on payments systems exists. The career at Visa exists. The photographs exist. The train journeys exist. The years in Dayton exist, and the years on the Peninsula, and the particular way the light falls on the California coast at Pescadero in the late afternoon — when the fog is still offshore and the hills are improbably green and everything goes briefly, completely quiet, as if the world is deciding whether to continue.

These are not things I am building toward. They are things I am.

Sacerdote would say I have high market share in a specific category. The category is small — one person, one particular configuration of experience and attention and accumulated knowing — but the share is essentially total. There is no competitor for the position of having lived this particular life. The moat is absolute. The switching costs are infinite.

I used to find that thought melancholy. The narrowing as loss. The aperture closing on what remains.

I’m not sure I find it melancholy anymore.

The L-Curve, Sacerdote says, is a long flatline followed by a vertical explosion. The tinkering phase, then the moment of lift. He means it as a description of demand curves for technology infrastructure. But I recognize the shape from somewhere closer. The long middle of a life, building and becoming, and then the morning you wake up and realize the building is substantially done. What remains is the being.

That’s not an ending. It’s a different kind of beginning.

Sacerdote’s metric will eventually stop working. All frameworks do. The AI infrastructure cycle will mature, the L-Curves will flatten, and some new measure will emerge to find the next thing that is just beginning to become what it will be. That’s the nature of markets. The detector has to change as the signal changes.

But there’s a complication worth naming. Analysts at Citadel Securities published a note recently observing that even the most powerful technologies must pass through the prosaic discipline of cost curves, capacity constraints, and marginal returns. Token bills are arriving unexpectedly. Compute is scarce. The vision of AI as ubiquitous, frictionless, and immediate is colliding with physical reality. Their conclusion: asset prices will periodically be forced to reconcile ambition with physical constraint.

That’s not a refutation of Sacerdote. It’s a reminder that feeling like you’ve arrived and having actually arrived are different things. The being phase has to be load-tested. The position has to hold under pressure.

I think about the fiber optics Corning is laying into the massive data center clusters — ultra-thin, bendable, carrying more light than anything that came before. The cable doesn’t know it’s infrastructure. It just carries what it’s given, at the speed it’s capable of, across whatever distance is required. It doesn’t matter what the cable believes about itself. What matters is whether the light actually moves.

That seems right to me. You become what you are over a long time, largely without noticing. And then one day someone builds a metric that accidentally describes your life, and you recognize yourself in it, and you think: yes. That’s the shape of it. High concentration. High share. A moat that deepened while you were looking elsewhere.

But the moat still has to hold.

The being phase, it turns out, is not the end of something. It’s the proof that something was built. And the daily question — for companies, for infrastructure, for a person in his late seventies still writing, still paying attention — is whether what was built is actually load-bearing.

You don’t get to stop finding out.

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 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?