Categories
Business Startups Venture Capital

Great Open-Field Runners

The plane was somewhere over Nebraska. Dick Kramlich sat across from me. We were on the same board then, and the rides together had become their own kind of conversation. He talked 1:1 the way certain men do when the clock has stopped mattering: without hurry, without the need to impress.

I asked him the question that had been riding with me for a while. After decades of sitting with founders, after watching tens of companies rise or disappear, what was the difference? What separated the ones that made it from the ones that simply ran out of road?

He didn’t answer right away. He looked out the window for a moment, then back.

They had done a study once, he said โ€” a hard look at outcomes, not opinions. What it found stuck with him ever after: the companies that survived were almost never the ones that had stuck to the plan. Success required the pivot. Not once, but again and again, until the company that arrived was almost unrecognizable from the one that had set out.

Then he gave the image that has stayed with me longer than any spreadsheet or term sheet.

He looked for great open-field runners.

Not the ones who could only run between the tackles, powering straight ahead into the line. The ones who could see daylight where it did not yet exist, who could plant a foot and cut, who understood that the shortest path is rarely the one that gets you home. Zig and zag. Feel the defense shift and refuse to be trapped by the original play call. Keep the ball moving toward the only thing that matters: the space that opens when you stop insisting the field must look the way you imagined it on the whiteboard.

I have carried that sentence for years. Great open-field runners.

It never felt elegant inside the room.

Kramlich had seen enough to know that the founders who could do this were rare. The ones who lasted treated the plan the way a great running back treats the designed play: as a starting point, not a contract with the universe. They trusted the daylight more than the diagram.

I think about him sometimes when the ground shifts under something I thought was settled โ€” when a strategy that once felt inevitable begins to feel like a trap, when the clean line on the page starts to look like a cage.

Dick is gone now. The rides are over. But the image remains, clean and sharp as the day he offered it at thirty thousand feet: a runner in open space, eyes up, cutting toward the light that only appears after you abandon the path you thought you were supposed to take.

Categories
AI Startups

A New Reason to Launch

โ€œBefore you launch, the speed you can build is now mainly limited by your imagination in what you tell AI. After you launch, the AI can watch your users and make improvements on its own.โ€
โ€” Jared Friedman, Y Combinator

Jared Friedman watches hundreds of founders a year navigate the gap between idea and launched product. He notices patterns the rest of us miss. And what heโ€™s describing above is not an incremental improvement in how software gets built. It is a change in the nature of the advantage.

This is a different kind of liberation than founders have known before.

The old liberation was launch early and the market corrects your wrong assumptions. Humbling, but useful. You were still the one doing the correcting, late at night, rewriting the onboarding flow based on what the data told you.

The new liberation heโ€™s describing is something closer to multiplication. You launch, and now there are effectively more of you. The AI is watching session replays youโ€™ll never have time to watch. Itโ€™s noticing the drop-off after step three that youโ€™d have caught in month four. Itโ€™s holding the pattern of a thousand user paths simultaneously and asking what they mean. Your imagination seeded the thing. Reality is now feeding it.

That observation redraws the map cleanly. Pre-launch and post-launch used to differ in degree โ€” you knew more after than before. Now they differ in kind. Pre-launch you are the sensing organ. Post-launch youโ€™ve grown new ones.

The founders who feel this most viscerally, I suspect, are the ones building alone or in pairs โ€” the people for whom every previous era of building had a hard ceiling imposed by human hours. They could only read so many support tickets. They could only run so many experiments. The ceiling is lifting and the feeling is of a room getting larger.

The core advice hasnโ€™t changed. Paul Graham was saying โ€œlaunch earlyโ€ twenty years ago and it was true then. Whatโ€™s changed is the reason underneath it โ€” the mechanism that makes it true now is nothing like the one he had in mind.

The advice is twenty years old. There is a new reason and it is brand new. Most people havenโ€™t noticed the swap yet. But they will.

That window does not stay open long.

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

The Topography of a Face

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

Elad Gil recently shared a fascinating experiment during a conversation with Tim Ferriss. Heโ€™s been uploading photos of startup founders into AI models and asking the machines to predict if theyโ€™d be successful, purely based on their โ€œmicro-features.โ€

“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-featuresโ€”like, do you have crow’s feet by your eyes, which suggests that your smiles are genuine? [โ€ฆ] 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. Itโ€™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, Iโ€™ve often leaned heavily on this silent language. Iโ€™ve backed founders because their intensity felt genuine, and Iโ€™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. Iโ€™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 โ€œcold reader,โ€ 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 rightโ€”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.