Category: Storytelling

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, he’ll tell you plainly, isn’t technical. It’s selling. Recruiting, fundraising, convincing customers, inspiring teams. “Actually being able to write code,” he said recently, “is probably not a big deal anymore.” What matters is whether you can cross the distance between your vision and someone else’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 — there is always a drawer, there is always a cable — 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 hasn’t decided what it wants to be. They were early. He set his bag down and sat directly across from me — not at the presenter’s angle, not with one eye already calculating the distance to the screen — 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 hadn’t chosen. I was, in some way I couldn’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 didn’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 doesn’t make sense. What we are really talking about is the oldest technology human beings possess — 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 — when it really works — 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 doesn’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 wouldn’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 won’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
Storytelling Writing

The Craft in the Work: A Reading Guide to Ten Storytellers

There’s a kind of reading that’s really a form of listening — not to what a writer is saying but to how they’re solving a problem. Every great piece of nonfiction is an argument about structure, and most writers never explain it aloud. The argument is in the choices: where the piece starts, when it digresses, what it leaves out, how it ends. You can enjoy the work without seeing any of this. But once you start seeing it, you can’t stop — and eventually, some of it becomes yours.

This guide is for both kinds of reading. Each writer here is worth your time as a reader. Each one also has something specific and stealable for anyone who writes. I’ve tried to name both.

The ten: John McPhee, Robert Caro, John Jeremiah Sullivan, Michael Lewis, Joan Didion, David Grann, Sam Anderson, Susan Orlean, Tom Junod, and Wright Thompson. Different registers, different obsessions, different methods. What they share is a commitment to making difficult things feel inevitable — and the discipline to make that look effortless.

They fall into three loose clusters, which might help you find your entry point. Structure builders — McPhee, Caro, Grann — write pieces that feel inevitable because the architecture is invisible but load-bearing. Emotional access — Orlean, Junod, Thompson — get you inside feeling before you know you’re there. Voice and form — Didion, Sullivan, Lewis, Anderson — the sentence, the digression, the explanatory seduction, the essay as genuine inquiry. The clusters overlap, and the best writers in each group are doing all three things at once. But if you’re trying to solve a specific problem in your own writing, the clusters tell you where to look first.

Continue reading “The Craft in the Work: A Reading Guide to Ten Storytellers”
Categories
Storytelling Writing

The Nerve of the Opening Line

For years I wrote first paragraphs that explained what I was about to say, which is a little like a joke that begins by describing how funny it is.

Susan Orlean has a better idea. In her book Joyride, she writes that a lede doesn’t need to preview the story or summarize what the rest of the piece will be about. What’s important is that it captivates readers and holds them fast to the page so they keep reading.

The conventional wisdom about ledes is that they exist to tell readers what they’re about to read. The billboard theory of the opening. Here is what this story is. Here is why it matters. Here is what you’ll find if you continue. The lede as table of contents, compressed.

Orlean is saying something stranger and more honest: the lede’s job is not to inform. It’s to hold the reader.

There’s a distinction there worth sitting with.

Informing a reader is a transaction — you transfer content, they receive it. Holding a reader is something else entirely. It’s closer to what a magician does in the first thirty seconds of a performance, or what a stranger does when they say something at a party that makes you turn and face them fully. You haven’t learned anything yet. You’ve just been made to stay.

The ledes that have held me longest tend to have almost nothing to do with the stories they open.

Joan Didion begins “The White Album” with a single sentence — “We tell ourselves stories in order to live” — that takes the entire essay to even partially fulfill.

Gay Talese opens his Frank Sinatra profile not with Sinatra’s voice or his legend but with a man going silent: “Frank Sinatra, holding a glass of bourbon in one hand and a cigarette in the other, stood in a dark corner of the bar between two attractive but fading blondes who sat waiting for him to say something. But he said nothing.”

Tracy Kidder opens The Soul of a New Machine not with computers but with a boat in a storm, Tom West awake for four straight nights while everyone else is seasick, the rest of the crew left wondering what on earth this man does for a living.

None of these ledes summarize. All of them hold.

What they share, I think, is a quality of disturbance. They’ve moved the ground slightly underfoot. Something is tilted.

Didion’s first sentence argues that we tell ourselves stories in order to live, and you feel the vertigo in it immediately — wait, is that true? Is that a good thing or a desperate thing?

Talese gives you a man diminished by illness and silence, and everything that follows is measured against that diminishment.

Kidder’s boat goes somewhere that prose about minicomputers wouldn’t, and by the time you’ve crossed that dark water with West, you’re already a different kind of reader than you were on page one.

I think about this when I try to write.

I grew up reading ledes the billboard way — I thought the first paragraph was a promise about what the reader would receive. And sometimes I still write them that way, which is to say I write them first and delete them later, because they’re stage fright disguised as generosity. Here is what I’m about to tell you really means please don’t leave before I find my footing.

The Orlean formulation — captivate, hold, keep reading — shifts the pressure off the writer’s anxiety and onto the reader’s experience. The question is no longer what do I need to tell them? The question is what will make them unable to leave?

That’s a harder question. It requires knowing something about what people can’t resist. Strangeness. Motion. A body in trouble. A door left open. The suggestion that someone knows something you don’t.

The best ledes I’ve ever written didn’t come first. They came after I’d already written the whole piece and finally understood what it was actually about — which turned out not to be the thing I thought it was about at the start. You can’t write the sentence that makes someone stay until you know what you’re asking them to stay for.

The lede isn’t a promise. It’s a wager. You’re betting that the reader will follow disturbance into the dark — and the only way to make that bet is to trust the disturbance yourself first. Most of us don’t. Most of us write the billboard because we’re afraid that if we don’t explain what’s coming, the reader will leave.

But the reader doesn’t leave because they’re confused. They leave because nothing reached out and held them.

The explanation never does that. The strangeness might.

Categories
Authors Storytelling Writing

The Architecture of Resonance

There’s a particular kind of madness that strikes writers late at night, or in the stagnant hours of mid-afternoon, when you find yourself staring at a single sentence for twenty minutes.

You’re weighing a semicolon against an em dash. You’re wondering if “murmur” is too soft or if “whisper” is too cliché. All of this while knowing, with complete certainty, that no reader will ever stop to appreciate this specific choice. They’ll just read the sentence and move on.

So why do we do it?

In Draft No. 4, John McPhee — the legendary literary journalist who spent decades at The New Yorker — shares a principle he still writes on the blackboard at Princeton. It’s actually a quote from Cary Grant: “A Thousand Details Add Up to One Impression.” The implication, McPhee explains, is that almost no individual detail is essential, while the details as a whole are absolutely essential.

I find this idea endlessly useful. And a little reassuring.

Think about walking into a beautifully designed home. You don’t notice the precise angle of the crown molding or the specific undertones of the paint. You don’t walk in and say, “Ah yes, Alabaster White.” You just feel warmth, or elegance, or comfort. The impression is singular — but it’s entirely built from a thousand invisible decisions someone made before you arrived.

Writing works the same way. The rhythm of your sentences, the specificity of your verbs, the way a paragraph ends — these are the details. Individually, they’re expendable. Swap “murmur” for “whisper” and the piece survives. Delete the semicolon and the world keeps turning.

But collectively, they are the piece.

Start compromising — reach for the easy cliché, let a clunky transition slide, settle for vague where you could be specific — and the foundation slowly rots. The reader won’t be able to name the moment they lost interest. They’ll just close the tab. The impression shifts from resonant to flat, without anyone quite knowing why.

Writing, then, is an act of quiet faith. It asks you to labor over things no one will applaud. Nobody claps for an em dash. But the work isn’t really for applause — it’s out of respect for the whole.

We curate a thousand invisible things so the reader can feel one visible truth.

So the next time you’re agonizing over a single word at midnight, remember: you’re not just picking a word. You’re placing a tile in a mosaic. Cary Grant understood it. McPhee put it on a blackboard. You might as well make it count.