Billionaire Cashback System: I Can't Go Broke!-Chapter 18: The NYC Way

The building said everything about itself without trying.

Ryan stood on the pavement outside it, hands in his coat pockets, and took it in — the kind of pre-war architecture that Manhattan did better than anywhere else, stone façade, high windows, a doorman who’d looked Ryan over once when he arrived and then returned to a carefully neutral expression.

The kind of building where the lobby probably had better furniture than most people’s apartments.

He looked around at the street, the wide clean pavements, the cars that seemed newer here, the particular quiet of a neighborhood that could afford to muffle its noise.

He came to Manhattan constantly and somehow rarely ended up in this part of it. Everything here had a price point that made it someone else’s part of the city.

He checked his phone. Sent the text.

’Outside.’

Then he waited, shifting his weight once, looking up at the building again. He’d spent twenty minutes that morning staring at his wardrobe — the new wardrobe, post-Mercer Street — and landed on dark baggy trousers, a fitted grey shirt, and the long charcoal coat over everything.

Casual but considered. He wasn’t going to overthink it more than that.

He’d thought about picking her up with a car, briefly.

A rental, something that matched the postcode he was currently standing in. He’d dismissed it almost immediately, the way you dismiss an idea that sounds reasonable for about four seconds before you remember who you are.

She’d bought him a drink because of a cheap shirt. Showing up in a rented Mercedes would be the most effective way to immediately become every other guy she’d ever met.

Besides. A car in New York on a weekday was a punishment, not a luxury.

They’d do it the city way.

He was mid-thought when the door opened.

He watched her come down the steps and felt his brain briefly lose the thread of whatever it had been doing.

He’d remembered her clearly from the gallery — the white dress, the effortless way she moved through a room. But memory had a way of softening things, smoothing them into something slightly less than the real version.

Standing in front of him now in dark straight-leg jeans, ankle boots, and a camel coat belted at the waist, hair down and slightly loose, she was the real version. His memory hadn’t done a good job.

She came down the last step and looked up at him — he had a couple of inches on her — with an expression that was somewhere between greeting and assessment.

"Hi," Ryan said.

"Hey." Her eyes moved over him once, unhurried. "You can actually dress well sometimes."

"I just threw something on."

"Mm." The corner of her mouth moved. "Sure you did."

Ryan turned toward the street and she fell into step beside him. He said, "I was thinking we take the subway. But if you’d rather I can grab a cab."

Zara glanced at him. "The subway."

The way she said it had a specific quality — it didn’t feel like refusal or even surprise, more like someone accessing a part of their life they hadn’t visited in a while and checking if it still existed.

"That’s fine," she said.

They started walking.

---

The Upper East Side on a Tuesday morning had its own specific energy — dog walkers, people carrying coffee like a structural requirement, the occasional tourist moving slightly too slowly and looking slightly too upward.

Ryan and Zara moved through it at a comfortable pace, walking with enough direction to feel purposeful without being so fast it killed the conversation.

"So," Zara said. "What do you actually do? You said you were working the room at the gallery, making connections. For what?"

"Software development," Ryan said. "I was at a company for three years, then I wasn’t. And now I’m starting my own."

"That’s the startup."

"That’s the startup."

She nodded slowly. "So the whole working the room thing was for the company. You needed the connections."

"Something like that." He glanced at her. "Also I enjoy insulting art to beautiful women. That part was personal."

She kept her eyes forward but he caught the small smile. "How’s the startup going?"

"Early days. I have a team. We’re figuring out what we’re building."

"You don’t know what you’re building yet?"

"We know the space. We’re stress-testing the direction." He paused. "It’s less chaotic than it sounds."

"It sounds extremely chaotic."

"It’s moderately chaotic," he conceded.

She laughed briefly, and it was the same laugh from the gallery — unguarded. He’d thought about that laugh a few times over the past two weeks without meaning to.

They walked a block in comfortable quiet, the city filling the space that conversation left.

Then Zara said, "You’re very critical of contemporary art."

Ryan glanced at her. "You’ve been thinking about that."

"I found it interesting." She pulled her coat slightly tighter as they turned a corner and caught the wind off the cross street. "Most people at those events either love everything or act like they do. You were the only person I heard actually say something negative."

"Negative and specific," Ryan said. "That’s different. Anyone can dislike something."

"Okay, so specifically — what’s your problem with it?"

Ryan thought about it for a moment.

"It’s the spark," he said. "Or the lack of it. You look at a lot of that work and it’s technically accomplished, sometimes genuinely impressive from a craft standpoint — but there’s nothing hungry in it. It’s comfortable art. And I don’t think comfort and great art really coexist."

Zara was quiet, listening.

"That’s not entirely fair though," she said. "You’re assuming struggle is a prerequisite for good work. Some people create well from a place of security."

"Some," Ryan said. "But not most. And I don’t think I’m being unfair, I think I’m being honest about how humans are wired." He side-stepped someone walking three dogs badly. "When you don’t have much choice but to be great — when the alternative to making something extraordinary is obscurity or poverty or just complete irrelevance — that pressure produces something you can’t manufacture any other way. You can feel it in the work."

"And when that pressure goes away?"

"Then complacency isn’t just a possibility," Ryan said. "It’s practically inevitable. Because the thing about people is — if you give them the option to not do their best, most of them won’t. Not out of laziness. Just because we’re built to conserve energy. Struggle is inefficient. The brain wants to stop struggling the moment it’s allowed to."

They reached a crosswalk and waited for the light.

"You see it with musicians," Ryan continued. "First album, the artist is twenty-three, broke, sleeping on someone’s couch, spending fourteen hours a day in a home studio missing meals to get one song right. That album is extraordinary. Decade later, they’ve got a house in Malibu and three Grammys and the new album is — fine. Professional. Technically better in every measurable way." He shook his head. "But it doesn’t do anything to you."

"Because they’re comfortable," Zara said.

"Because they’re comfortable. The hunger’s gone. And hunger is what made the first one matter."

The light changed. They crossed.

Zara walked a few steps in silence, and Ryan let it sit — he’d learned that about her from the gallery, she processed before she responded, which he’d found he liked. It meant when she said something back it was actually a response and not just a reaction.

"I think you’re mostly right," she said finally. "But I think you’re leaving something out."

"What’s that?"

"Some artists stay hungry because of something internal. Not circumstantial." She glanced at him. "The external pressure can be gone and the hunger stays because it was never about the circumstances in the first place. It was about who they are."

Ryan considered that. "Those are the rare ones."

"They are," she agreed. "But they exist."

"Yeah." He nodded slowly. "I’m trying to be one of those."

Zara looked at him sideways. Something in her expression shifted slightly, the way it had at the gallery bar — the door opening another inch.

She didn’t say anything to that. Just looked forward again at the street ahead.

The subway entrance appeared at the end of the block, the green globe lamp marking it from half a block away.

Ryan gestured toward it. "After you."

Zara looked at the entrance, then at him, then back at the entrance with the expression of someone accepting a reasonable challenge.

"You know," she said, starting toward it. "I genuinely cannot remember the last time I took the subway."

"It’ll come back to you," Ryan said. "Like riding a bike. Except louder and it smells worse."

She laughed going down the steps ahead of him, the sound of it swallowed by the warm underground air rising from below.

Ryan followed her down.