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Edward Lando Headshot

Meeting Jack Dorsey

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Last week, 20 Penn undergraduates traveled to Silicon Valley to tour large tech companies and meet founders. This is my impression of a meeting with Jack Dorsey.

We walk past the Square logo that glows on the white wall to the reception where the pretty receptionist is waiting for us and the good music plays. The space sucks you in and there's a center of the world feel.

Behind a glass wall the entrance continues. A long stretch of carpet and emptiness marked only by two distant couches that sit like stones in a Japanese rock garden.

Once we're in and step forward, we see the rest of the floor and it goes on forever long and wide. We're in downtown San Francisco, where a lot of nothingness is the most precious thing.

All this negative space reminds of Twitter and Square and everything Jack. We go past empty work desks with double Apple displays, past soundproof and cushioned square booths and glass cabins, all the way to a coffee bar that's here to power the squadrons and where everything costs a dollar, a dollar that you'll pay with Square so you're always testing the product and its new features.

Everything is light wood and light grey and dark grey (we're asked to stay on the light grey carpet), softly lit, relaxing and enlivening. Not corporate, just elegant.

"I just feel like doing all my work here," someone says in the group.

Our guide slows down and stops. She's thinking.

"So, we've got a few more minutes. We could continue the tour, or we could go up to the ninth floor now... Yes, let's go up now. I don't want to be late for Jack." Neither do we.

We walk back through the glass, past the receptionist who smiles us through, and all compress into the elevator, pressing unwary employees against the walls, and we go up.

There are strong, standing security guards when the doors open. We ignore the sensory catcalls of the buzzy cafeteria. We're all hungry, even more now, but we're told breakfast is after Jack.

We walk to an airy conference room that's behind one long sheet of glass. Inside, we all sit down like the board members we aren't, looking at each other, looking at the almost 180-degree view of the city.

Our guide tells us Jack will be a few minutes. Those of us facing away from the door contort enough to glance every few seconds, expecting something. We're all dreamy from the lack of sleep.

Finally, "Look who's coming!"

We all look and there is Jack, on the other side of the glass, sailing in our direction, looking at us looking at him, eyes that stay fastened as he moves.

We're scrambling for no reason, pulling up our sleeves and then pulling them down, taking pen in hand and then realizing we don't need a pen yet, turning to a neighbor to whisper onomatopoeias more than words.

Then, the door is pulled away and Jack comes through the wall, toward us in our silence and his.

He sets down his coffee and French water and looks around a little: "Hi."

We don't answer. We look at him. His eyes are lagoons.

He smiles as much as Jack Dorsey smiles, when others would go pink in front of such inquisitive silence.

"I just came to say hi. Do you have anything to say?"

A few laughs, shoulders drop, lungs exhale in quiet and questions are gently pushed forward. We've pretty much agreed on those beforehand because we don't have much time.

Jack answers with few words that everyone writes down faster than needed. I've read he likes the sea, and Hemingway, and Neruda, and the Golden Gate, and sailing, and all of these show themselves in how he is, his tone.

I feel reluctant to speak, to intervene. Instead I listen and look at his plain dark cashmere sweater, his clean jeans, even his smooth leather shoes. Everything feels worth studying.

We want to know about his habits. We want to be more like him. He keeps afternoons free to take walks and look at people and how they go about living. He goes to the same restaurants every week. He keeps separate note pages for everyone he meets to keep track of the conversation and one of these is about him, one has a list of do's and don'ts.

"Do: drink lots of water, run, stand up straight

Don't: be late, drink liquor on weekdays"

There are others.

He would rather show people success than speak it. He thinks entrepreneurs should ask themselves what canvas they want to paint on. He wants to move the fastest in the largest market. He likes to think of deeper versus broader, and prefers deep over broad but likes to reconcile them, talks about Carl Sagan and having the entire universe in a grain of sand, how by going deeper into something we see the breadth of the universe.

Our guide has to tell him he has another meeting. He's forgotten about the time. We crowd around him for a picture, but looking back at it now I see we've left a reverential margin around him. Time is running dry and we ask him for a few more drops of ideas, anything from his brain. We ask him for book recommendations. He likes The Old Man and the Sea, he says. I know that. I mention The Master and Margarita, which I also know he likes and he looks at me and says: "That's a great book."

I think of the story Jack tells of the very beginning, when he saw the great Ev Williams in a coffee shop, and how he was too shy to talk to him and how he instead just looked him up and applied for a job.

I don't think that's what will happen here, but in that moment I also feel a desire to keep quiet.

There's a little space to say something more as we're posing and unposing for the camera but I don't. I'd love to know him, obviously. He seems so filled with unusual emotion and pathos and secrets and when you meet him you'll also want to go sail with him around the world.

But to know him better is to learn that he's a person. And even though Jack told us himself that he doesn't approve of putting public figures on a pedestal, it's hard to avoid doing that with him, and that's good, because no other 15 minutes have ever motivated me like these. I didn't learn much at all, a few life hacks at most, but I'm filled with an impression, and I want to hold on to it.