A lot can happen in the last 5 seconds of a Zoom call, when those who are less quick to the draw scramble for the “leave” button. On this Wednesday afternoon, it’s Matt and Josie fighting for the trigger. Behind their apologetic smiles lie gritted teeth. They have investors to update. They have emails in their inboxes. So why is it taking so long for their cursors to venture to the bottom right corner of their screens? They’ve already said their goodbyes. The AI has taken all the notes down. What are they afraid will happen when they …

Click.

Their rounds go off in the same instant, if we are to keep the duel metaphor going. They’re both dead -- metaphorically.

In reality, their clicks take them out of the Wild Northeast. Far away are the nicotine pouches and unruly E-bikes of corporate New York. Yes, they’re embarking on a path that’s actually untrodden, for real this time. They’ve entered Ventureland.

“What’s Ventureland?” they ask, staring blankly at the sign. “Does it have to do with venture capital?”

Yes and no. In some ways, it’s a reference to the substack about a certain VC’s visits to America’s lesser-appreciated tech hubs. But in many other ways, it’s a new world, where things that seem familiar – and ideas that feel overused – are entirely reimagined.

At first it appears that the sign confronting them is on an island. They’d like to turn back, go back where they came from. Josie hasn’t checked her calendar in a little while, but she’s pretty sure she has another Zoom scheduled for 6 with her legal counsel. Some strange force takes a hold of her, though, making it impossible for her to move backward, or even to turn her neck toward whatever’s behind her. Matt experiences the same strange sensation.

“I have a Zoom scheduled for 6, I’m pretty sure,” Josie says.

“I think to get back we have to go forward.”

“You mean try to get on the island? I feel like we’ve been to “Ventureland” before. I know a lot about Venture.”

“Are you not saying exactly the same thing as me?”

They scrutinize their surroundings and come to realize that, rather than an island, Ventureland could be better described as a fortress. And the water, which churns ferociously at their feet and stings their ankles with its steam, is a moat.

They call out for assistance, but there’s no drawbridge. Turning his head as far to the left as his neck will allow, Matt notices a tree, and begins walking towards it. Josie yells out at him to stop. She’s done some inspection, and evidently there are no sharks in the water. Surely they can swim this short distance.

Wobbling awkwardly on one foot, she takes off her On Cloud. Just as she puts her toe in, to at least test the waters, she is met with agonizing pain. Her teeth bite an exceptionally cold scoop of ice cream with full force. Her fingernails scrape against rough pavement. She’s left something on the stove. She’s set her alarm for PM instead of AM.

Her mind goes on and on until she finally musters up the sense to remove her foot from the water. Something was deeply wrong, she concludes. But this makes her all the more determined to get across.

Josie turns to Matt, who is looking up to the top of the tree, eyes squinting in the sun. She walks towards him, and as he moves to the side to make space for her, his arm bumps against something. He looks down, and suddenly it’s already in his hand. It’s the low hanging fruit.

“Should we try it?” he asks her.
“You mean eat it?”
“Yeah, I don’t know.”
“This all just feels too easy.”
“I don’t know, we’ve got to do something, start somewhere. And I’m hungry.”
“Okay, but you go first.”

It’s a cluster of grape-like berries. He pops a couple in his mouth. As he chews, slowly, he begins to notice a strange sensation in his upper back. 

“You’re sprouting wings!” Josie screams. He is, in fact. And he’s developing a strange glow about him. She walks to the tree and grabs her own bunch…

…Stay tuned for “Scaling Ventureland Part II” to find out what happens next (Hint: they’ve become something that rhymes with “wangel sequesters”)