Categories
AI Apple Google

The Library You Already Own

Sharon Park in the morning is not a dramatic place. There’s a duck pond, a stand of oaks that go gold too briefly in November, and a loop I’ve walked enough times that my legs know it better than my eyes do. It is, in other words, exactly the kind of place where a person starts talking to himself. Not out loud. In the productive, low-grade way โ€” turning a sentence over, arguing with an idea from the day before, checking a thought against something you believe about yourself.

I think in five years I’ll be doing that walk with something else along. Not a search engine. Not another chatbot trained to know a little about everything and a lot about nothing in particular. Something closer to a second set of eyes on my own life โ€” a reasoning engine, lean and mostly private, that has actually read the things I’ve written and doesn’t need me to explain who I am before it’s useful.

Here’s the distinction that matters, and it took me longer than it should have to see it clearly. The AI industry has spent years in an arms race over how much of the world a model can hold โ€” more facts, more languages, more of the internet compressed into weights. That race will keep going, and somebody else can have it. What I want is smaller and stranger: a model that knows comparatively little about the world and quite a lot about me. My core values document. The portfolio spreadsheets. Fifteen years of blog posts. The half-finished notes for the I-280 project, sitting in a folder, waiting for someone โ€” or something โ€” to ask the right question about them.

I spent a career in payments infrastructure, which means I spent a career thinking about a very specific kind of trust: the kind where a stranger’s system has to make a judgment call, in milliseconds, about whether to say yes. Fraud models don’t work because they know everything about commerce. They work because they know an enormous amount about one account, one pattern, one person’s ordinary Tuesday โ€” enough to notice when Tuesday stops being ordinary. That’s the architecture I keep picturing, aimed inward instead of outward. Not a system trying to know the world. A system trying to know me, well enough to notice when I’m drifting from what I said I cared about.

I can already feel the shape of the mornings this would change. Right now, when I sit down to look at RMD requirements against the tax picture, I’m doing the translation myself โ€” pulling numbers into a story I can actually feel the weight of. A reasoning engine grounded in my real holdings wouldn’t just run the scenario. It would know that I don’t want the scenario dressed up as a spreadsheet; I want it dressed up as a conversation, unhurried, the kind you’d have over lunch with someone who already knows the whole situation. And on the mornings when I sit down to write, instead of staring at a blinking cursor and a blank page that has no idea I exist, I’d be handing a draft to something that has actually read my last two hundred posts and knows the difference between the sentence I’d write and the sentence I’d cut.

None of this is especially exotic technology. Apple and Google are already building toward it โ€” Neural Engines fast enough to do real reasoning on-device, retrieval systems that can reach into your own files instead of the entire internet, fine-tuning that’s getting cheap enough to personalize rather than merely customize. The more interesting story here isn’t privacy, though privacy is real. It’s architectural: what happens when the expensive, impressive part of the system โ€” the part that knows everything โ€” becomes optional, and the cheap, personal part โ€” the part that knows you โ€” becomes the whole point.

What I don’t yet know is what this will cost me. A tool that reasons this well about my own life is also a tool I could lean on instead of doing the leaning myself, and there’s a version of this future where the walk around Sharon Park stops being mine and starts being a conversation with something that finishes my sentences a little too well. I’d want some way of knowing, plainly, what it’s drawing from and what it’s guessing at โ€” less a nutrition label than a kind of honesty I could check against, the way you’d check a fraud model’s confidence score before you trusted it with a yes.

But most mornings, I think I’d take the trade. Not because I want to think less. Because for thirty years I’ve been collecting the raw material โ€” the notebooks, the portfolios, the half-built essays โ€” and it would be something, finally, to walk beside a mind that had actually done the reading.

Categories
Business Storytelling

The Closed Laptop

The conference rooms all look the same after a while. Same long table. Same chairs that cost more than they should. Same window with the same view of the same parking lot baking in the same California sun. You stop seeing them. You develop a kind of practiced receptivity, a professional openness that is also, if you are honest, a professional distance. You have heard the story before. You know where you are in the presentation without looking at the slide number.

Until the day someone sits down across from you and closes their laptop and says: can I just tell you our story?


Fred Wilson, the venture capitalist at Union Square Ventures, has spent forty years learning to tell the difference between founders who can build and founders who can make you believe. The skill he overweights now, heโ€™ll tell you plainly, isnโ€™t technical. Itโ€™s selling. Recruiting, fundraising, convincing customers, inspiring teams. โ€œActually being able to write code,โ€ he said recently, โ€œis probably not a big deal anymore.โ€ What matters is whether you can cross the distance between your vision and someone elseโ€™s imagination and deposit something true and alive on the other side.

Most founders never figure this out. They build the deck instead. They pull the projector cable from the drawer โ€” there is always a drawer, there is always a cable โ€” and the room fills with blue light and bullet points and the comfortable geometry of a prepared presentation, and what never happens is the thing that needed to happen.

But there was this one morning.


He came in with his cofounder in the flat gray light that Silicon Valley gets in February, when the rain has stopped but the sky hasnโ€™t decided what it wants to be. They were early. He set his bag down and sat directly across from me โ€” not at the presenterโ€™s angle, not with one eye already calculating the distance to the screen โ€” directly across, the way you sit with someone you already know, or intend to. Neither of them reached for the cable in the drawer.

He looked at me with the particular steadiness of a person who has decided not to manage the moment.

Can I just tell you our story?

I want to be honest about what happened next, which is that I felt something shift before he said another word. Not a decision exactly. More like the precondition for a decision, the ground tilting slightly in a direction I hadnโ€™t chosen. I was, in some way I couldnโ€™t have defended rationally at the time, already with him. And I knew it, and I knew it was not an entirely reasonable response to a man who had been in the room for less than a minute, and I felt it anyway.

The laptop stayed closed for the next twenty minutes. No transitions. No bullet points. No hockey stick arcing toward a number reverse-engineered from a desired outcome. Just his voice and what he believed and the quality of attention you give a person when there is nothing else in the room to look at.

The deck came later. It was beautiful. By then it didnโ€™t need to be anything except true.


Storytelling is not a skill in the way that financial modeling is a skill. It is older than that by such a margin that the comparison almost doesnโ€™t make sense. What we are really talking about is the oldest technology human beings possess โ€” a person in a room, a voice, an image made of nothing but words and the willingness to believe in them. It was doing its work around fires forty thousand years before the first conference room was built, and it has never once required a projector.

What the great storytellers understand, and what the best founders understand in the same unspoken way, is that a story is not a transfer of information. It is a transfer of inner states. When it works โ€” when it really works โ€” something that existed inside one person gets reconstructed inside another, and the listener emerges changed. Not persuaded. Not informed. Changed. These are different experiences, and only one of them makes a person willing to bet their career on something that doesnโ€™t exist yet.

The deck puts glass between the teller and that possibility. The founder stands at the edge of the blue light pointing at things, and the room evaluates the things, and what never happens is the transfer. Everyone files out having formed opinions about the slides rather than beliefs about the person. Opinions and beliefs are not the same.

Wilson understands this even if he wouldnโ€™t use these words. When he says the skill is selling, what he means underneath the selling is: can this person walk into a room and make other people inhabit their vision? Not convince them. Inhabit. The difference is the difference between reading about a place and being there. One of them changes how you act. The other one you forget on the drive home.


The projector cable is still in the drawer. Someone will pull it out next week, and the room will fill with blue light, and another founder will stand at the edge of it pointing at things, hoping that the right font and the right graph will do the work that only a human being, exposed and without props, can actually do.

It wonโ€™t. It never does.

The CEO who closed his laptop had been carrying a story he believed in, and he knew the story was the thing, not the packaging around it. He understood that the oldest container is also the most powerful one. His own voice. A room. Someone willing to listen.

I was ready to work with him before he said another word.

Categories
AI Business IBM Management

Making It Up As We Went Along

There was a building along Route 270 in Gaithersburg, Maryland where people kept secrets for a living. Not the cloak and dagger kind. The corporate kind, which in its own way requires just as much discipline. The IBM Washington Systems Center occupied a two-story modern building that looked, from the outside, like any other outpost of late twentieth century American business. Inside it was something else. It was where IBM sent its hardest problems, and where the largest IBM customers in the world โ€” the ones whose names you would recognize immediately โ€” sent their most urgent ones back.

I worked there as a manager. But before I was a manager there, I was a hire. And before I was a hire, I was like every other IBM professional on the outside of a particular line โ€” a line I didnโ€™t fully understand until I crossed it.


At IBM there was a protocol so embedded in the culture it had almost ceased to be a rule and become something closer to a religious observance. New products were not discussed until they were announced. Not hinted at. Not alluded to. Not whispered about with a favored customer over lunch. The announcement came in the form of something called a Blue Letter โ€” a formal communication from senior leadership that functioned as the official moment a product entered the world. Before the Blue Letter, the product did not exist in any conversation you were permitted to have. After it, you could talk about nothing else.

Violation was not a career setback. It was a firing offense. Full stop.

That clarity had a kind of elegance to it. You didnโ€™t have to calibrate how much you could say or navigate gray areas. The line was absolute. And because it was absolute, and because everyone knew the consequence of crossing it, the culture enforced itself. You didnโ€™t need surveillance. You needed people to understand the stakes, and they did.


What I didnโ€™t understand, from the outside, was what that line was doing to my imagination.

When you canโ€™t see the roadmap โ€” when the strategy and the unannounced products and the long arc of where the company is going are all behind a wall you have no access to โ€” you donโ€™t experience that as absence. You experience it as depth. The things you donโ€™t know feel like they must be there for a reason. The gaps in the announced picture feel like the gaps in a great iceberg โ€” whatโ€™s visible is impressive, but whatโ€™s below the surface must be more impressive still.

I had faith in IBMโ€™s strategic intelligence the way you have faith in things you canโ€™t fully see. And faith, uncontradicted by evidence, tends toward beauty. The hidden roadmap wasnโ€™t just unknown โ€” it was, in my imagination, a thing of coherence and intention and vision. It had to be. The alternative was too unsettling to consider.

Then I got hired into the Washington Systems Center and crossed the line.


There was no single moment of disillusionment. No specific product that shattered the dream, no strategy document that read like a disappointment. It was more like a gradual adjustment of the eyes โ€” the way they adapt when you move from bright sunlight into a room lit quite differently than you expected. The room isnโ€™t dark. Itโ€™s just not what you anticipated. And once your eyes adjust you can see perfectly well, but you can never quite recover the image you had of the room before you entered it.

The reality on the inside was messier than the dream on the outside. More improvised. More human. We were, in ways I hadnโ€™t anticipated, almost making it up as we went along. Not carelessly โ€” the people at WSC were extraordinary, the work was serious, the commitment was real. But the beautiful coherent roadmap I had constructed in my imagination from the outside bore only a partial resemblance to the actual thing. Strategy, it turned out, looked different up close. Less like architecture. More like weather.

I absorbed this alone. Nobody sat me down and named what I was experiencing. Nobody had the conversation with me that I would later learn to have with others. I found my way through it by degrees, the way you find your way through most things that donโ€™t come with instructions.

What came out the other side wasnโ€™t cynicism. It was something more useful โ€” a clearer eye, a more grounded relationship to the institution I was part of. The faith hadnโ€™t been wrong exactly. It had just been innocent. And innocence, once lost, canโ€™t be recovered. But what replaces it, if youโ€™re lucky, is something steadier.


Years later I was the manager. And I was hiring IBMers โ€” good ones, experienced ones, people who had spent serious careers on the other side of the blue line. They knew the products cold. They knew the customers. They knew how to work. What they didnโ€™t know, couldnโ€™t know, was what waited for them on the inside of the wall they were about to cross.

I knew it. Because I had been them.

There is a particular expression that crosses a personโ€™s face when the actual roadmap becomes visible for the first time. It isnโ€™t dramatic. It doesnโ€™t announce itself. Itโ€™s more like a subtle recalibration โ€” a slight stillness, a momentary adjustment behind the eyes. The person in front of you is doing quiet interior work, reconciling what they imagined with what theyโ€™re now seeing. The gap between those two things is doing something to them, and theyโ€™re not sure yet what to do with it.

I learned to watch for that expression. And when I saw it I knew what was coming if I didnโ€™t get ahead of it.


The danger wasnโ€™t disappointment. Disappointment is temporary, and smart people move through it. The danger was what disappointment hardens into when it isnโ€™t named and worked through โ€” a corrosive cynicism that poisons not just the person carrying it but everyone around them. A talented IBMer who had invested a career in faith, discovered the faith was misplaced, and decided the whole enterprise was therefore hollow โ€” that person could do real damage to a team. I had seen it happen, or the early stages of it, which was enough.

So I developed what I came to think of as the god is dead conversation.

The name came from Nietzsche, though the application was strictly practical. What Nietzsche meant โ€” or one of the things he meant โ€” was that when the organizing faith of a civilization collapses, the collapse doesnโ€™t leave nothing. It leaves a vacancy that has to be filled with something else, something built rather than inherited. The god is dead conversation was about helping someone through that vacancy quickly, before they filled it with the wrong thing.

It wasnโ€™t a long conversation. It didnโ€™t need to be. What it needed to be was honest, and direct, and delivered before the cynicism had time to set.

I would tell them what I saw happening. I would tell them it was normal, expected, that everyone who crossed this particular line felt some version of it. I would tell them the dream theyโ€™d carried on the outside wasnโ€™t foolish โ€” it was a reasonable response to incomplete information, and the information had been incomplete by design, and the design had served real purposes. None of that made them naive. It made them human.

And then I would tell them what Iโ€™d learned on my own, without anyone to guide me through it. That the messiness on the inside wasnโ€™t a failure of IBMโ€™s intelligence or intention. It was just what strategy actually looks like when youโ€™re close enough to see the seams. Every institution looks more coherent from the outside than it does from the inside. Thatโ€™s not a scandal. Thatโ€™s organizational life.


The conversations were tricky. There was real care required. You were asking someone to grieve something โ€” the beautiful imagined roadmap, the faith in a hidden coherence โ€” without tipping them into bitterness about what replaced it. You were trying to accelerate a process that, left alone, might drag on for months and quietly corrode their effectiveness. And you were doing it while also being their manager, which meant you needed them functional and engaged on the other side of the conversation, not just unburdened.

What I had going for me was credibility. I wasnโ€™t delivering a message from outside the experience. I had made the same crossing. I knew the specific texture of what they were feeling because I had felt it myself โ€” the diffuse quality of it, the absence of a single dramatic moment, the gradual adjustment of the eyes. When I told them I understood what was happening to them, I actually did. I think they could tell.

Trial and error had taught me the shape of it. What didnโ€™t work I had found out the hard way, at some cost, early on. What I arrived at had been load tested by real people in real situations. It wasnโ€™t a framework from a leadership seminar. It was something I owned completely, which meant I could adapt it in the moment rather than execute a script.


Most of them came through it well. Better than well, actually.

What I hadnโ€™t fully anticipated โ€” though in retrospect it makes complete sense โ€” was what replaced the faith once it was gone. It wasnโ€™t the steadier, clearer-eyed pragmatism I had found my way to alone. It was something more potent than that. Something that surprised me the first time I saw it and then became one of the things I quietly counted on.

They came out the other side feeling superior.

Not arrogant. Not dismissive of colleagues still on the outside. But quietly, privately elevated โ€” because they were now keepers of the secrets they had once only believed in. The blue line that had shaped their entire professional identity, that had defined the boundary of what they could know and say and imagine, was now behind them. They were on the inside. They had access. They had been trusted with the actual roadmap, the real strategy, the unannounced products that the rest of the world was still constructing faith-based pictures of.

The believer had become the keeper. And keeping, it turned out, was a more powerful identity than believing. The believer is passive โ€” sustained by what they imagine. The keeper is active, responsible, trusted. They carry something real rather than something projected.

It solved my practical problem neatly, though that wasnโ€™t why it moved me. What moved me was watching people find their footing on the other side of a genuine loss and discover that the ground there was solid โ€” different from what theyโ€™d imagined, but solid. They hadnโ€™t just survived the crossing. Theyโ€™d been changed by it in a way that made them more valuable, more grounded, more fully present to the actual work.

Which was, I suppose, what the god is dead conversation had been for all along.


I think about that blue line often these days.

We are living through a moment when artificial intelligence is advancing faster than most people can track, and the organizations building it โ€” the labs, the research teams, the companies placing enormous bets on where this technology is going โ€” have their own version of the wall. Not identical to IBMโ€™s. The competitive and legal architecture is different. The culture is different. But the basic structure is the same: there is what has been announced, and there is everything else, and most people are working entirely from the announced side.

Which means most people are doing what I did before I crossed the line at WSC. They are filling the gaps with faith. And faith, uncontradicted by evidence, tends toward beauty.


The unrevealed AI roadmap looks, from the outside, like a thing of coherence and intention. The capabilities that havenโ€™t been announced yet must be more impressive than the ones that have. The strategy must be more considered than whatโ€™s visible. The gaps in the public picture feel like depth rather than uncertainty โ€” like the part of the iceberg below the surface, which must be vast because the part above is already remarkable.

I am not saying this faith is wrong. I held the same faith about IBM and it wasnโ€™t wrong exactly โ€” it was innocent. The people constructing faith-based pictures of where AI is going are doing a reasonable thing with incomplete information. The information is incomplete partly by design, for reasons that make competitive and strategic sense, just as IBMโ€™s secrecy made sense. None of that makes the faith naive.

But Iโ€™ve been inside enough walls to know what the inside tends to look like. And I think itโ€™s worth saying, clearly and without cynicism, that the reality is probably messier than the dream. More improvised. More uncertain. More human. The people building these systems are extraordinary โ€” the work is serious, the commitment is real โ€” but they are also, in ways that might surprise you, almost making it up as they go along. Not carelessly. But without the complete map that the outside imagines must exist somewhere, fully drawn, waiting to be revealed.

Strategy, up close, looks less like architecture and more like weather.


This isnโ€™t a counsel of despair. Itโ€™s almost the opposite.

The IBMers who crossed the line and survived the god is dead conversation didnโ€™t end up with less than they started with. They ended up with more โ€” a clearer eye, a more grounded relationship to the institution, a more useful kind of engagement with the actual work. The faith they lost was the innocent kind. What replaced it was steadier and more durable.

I suspect something similar is available to anyone willing to look at the AI moment with clear eyes. Not the disappointed cynicism of someone who expected a beautiful coherent roadmap and found a human institution instead. Not the breathless faith of someone still on the outside of the wall, filling gaps with generous assumptions. Something in between โ€” harder to sustain, more honest, ultimately more useful.

The technology is real. The progress is real. The stakes are real. None of that requires the roadmap to be a thing of beauty. It just requires it to be worked on seriously by people who understand what they donโ€™t yet know โ€” which, from everything I can observe, it is.


What I couldnโ€™t give those IBMers, and what nobody can give you, is the experience of crossing the line yourself. The god is dead conversation only works because the crossing has already happened โ€” because the person sitting across from you has already seen the actual roadmap and is already processing the gap between what they imagined and what they found. You canโ€™t have the conversation in advance. The disillusionment has to be real before it can be worked through.

Most of us will never cross the line into the AI labs. Weโ€™ll stay on the outside of the wall, working from the announced picture, filling the gaps as best we can. Thatโ€™s not a failure โ€” itโ€™s just the condition most of us are in, the same condition those IBMers were in for their entire careers before I hired them.

But knowing the wall exists, and knowing what walls do to imagination, seems like it ought to change something about how we hold our faith. Not abandon it. Just hold it a little more lightly. Stay curious about the seams. Remain open to the possibility that the most important thing about the unrevealed roadmap isnโ€™t whatโ€™s in it โ€” but what weโ€™ve projected onto it.

The blue line is still there. Most of us are still on the outside of it.

And the hidden roadmap still looks, from here, like a thing of beauty.

Categories
Friends Gratitude Kindness Living

The One Thing Money Doesnโ€™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 friendโ€™s apartment and the specific grace of someone who didnโ€™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 โ€” thirty years of it, billions of dollars of it โ€” 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 Oโ€™Shaughnessy asked him about it near the end of a long conversation. The kindest thing anyone has ever done for you โ€” itโ€™s the question Oโ€™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 โ€” before adding that the moment you start treating it as an investment, youโ€™ve already lost the thread.

Then he quoted Palmer Luckey.

The one thing money doesnโ€™t buy you is friends that believed in you when you had nothing.

Luckey built Oculus in his parentsโ€™ 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 Carterโ€™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 couldnโ€™t see. These moments are nearly invisible when they happen. They only become legible later, once the room turns out to matter โ€” 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 AI: Large Language Models

The Texture of Autonomy

There is a distinct texture to working with a truly capable person. It is a feeling of relief, specific and profound.

When you hand a project to a junior employee who “gets it,” the mental load doesn’t just decrease; it vanishes. You don’t have to map the territory for them. You don’t have to pre-visualize every stumble or correct every navigational error. You simply point to the destination, and they find their way.

I was thinking about this feelingโ€”this specific brand of professional trustโ€”when I read a recent observation from two partners at Sequoia regarding the current state of Artificial Intelligence:

“Generally intelligent people can work autonomously for hours at a time, making and fixing their mistakes and figuring out what to do next without being told. Generally intelligent agents can do the same thing. This is new.”

The phrase that sticks with me is “without being told.”

For the last forty years, our relationship with computers has been strictly transactional. The computer waits. We command. It executes. Even the most sophisticated algorithms have essentially been waiting for us to hit “Enter.” They are tools, no different in spirit than a very fast abacus or a hyper-efficient typewriter.

But we are crossing a threshold where the software stops waiting.

The definition of intelligence in a workspace isn’t just raw processing power; it is the ability to recover from failure without supervision. It is the capacity to run into a wall, realize you have hit a wall, back up, and look for a doorโ€”all while the manager is asleep or working on something else.

When Sequoia notes that “this is new,” they aren’t talking about a feature update. They are talking about a shift in the ontology of our tools. We are moving from an era of leverage (tools that make us faster) to an era of agency (tools that act on our behalf).

This changes the psychological contract between human and machine. If an agent can “figure out what to do next,” we are no longer operators; we are managers. And as anyone who has transitioned from individual contributor to management knows, that is a fundamentally different skill set. It requires clearer intent, better goal-setting, and the ability to trust a process you cannot entirely see.

We are about to find out what it feels like to have a digital colleague that doesn’t just listen, but actually thinks about the next step.

Categories
AI Leadership

The Power of Two

I recently watched and thoroughly enjoyed Harry Stebbings’ interview with OpenAI’s Sam Altman (CEO) and Brad Lightcap (COO). In addition to gaining new insights into OpenAI’s evolution, their conversation covered a wide range of topics regarding the future of AI and its implications for society and new ventures.

One of the most fascinating aspects was the dynamic between Altman and Lightcap — hearing them discuss their respective strengths, weaknesses, and how those translate into their roles at OpenAI. It’s uncommon to witness a dual interview like this, with two colleagues who have clearly worked together for years and have complete confidence and trust in each other’s judgment and insights.

Throughout my involvement with various small companies, I wish I could have experienced such a powerful duo! In my experience, it’s not uncommon for the CEO to dominate the senior management team’s dynamics. While this sometimes works well, I’ve also seen it lead to reduced performance or frustration among senior managers due to the CEO’s actions.

Altman and Lightcap (and OpenAI by extension) appear to have a much more synergistic working relationship — effectively amounting to a co-equal division of responsibilities. I highly recommend watching this conversation for anyone involved in a startup aiming to scale quickly and effectively! Congratulations to Harry Stebbings for his hosting this excellent conversation with two key individuals leading the evolution of AI!