Billionaire Cashback System: I Can't Go Broke!-Chapter 49: The Lockridge Dinner

The venue was a converted building in the Upper East Side that had been a bank in a previous life and still carried the architecture of that — high ceilings, stone columns, the grandeur of a space built to communicate permanence.

Someone had dressed it for the evening with long tables, candlelight, and floral arrangements that cost more individually than Ryan’s first month of rent.

He arrived at seven, which was the time on the invitation, and immediately established that arriving at the time on the invitation meant arriving before most people who actually belonged here.

The early crowd was staff and photographers and a handful of guests who, like Ryan, had taken the time literally.

He checked his coat, took a glass from a passing tray, and looked at the room.

Black tie meant something different depending on your tax bracket. At the lower end it meant a suit you’d bought for the occasion and shoes that were slightly too new.

At the upper end it meant things that had been made specifically for your body by people whose names you knew. The room was running heavily toward the upper end — the particular ease of people wearing expensive clothes they’d worn before, the absence of anyone tugging at a collar or checking a reflection.

Ryan looked down at his own suit.

Charcoal, well-cut, Zara-approved by proxy of the shopping trip. He looked fine.

He knew he looked fine. He stood with his drink and watched the room fill and had his mind drift to the IRS interview in eight days and the investment paperwork that was two signatures away from being final and the date with Zara on Sunday, and let the evening arrive around him at its own pace.

Diana found him at 7:24.

He heard her before he saw her — not her voice, just the shift in the room’s attention that followed her when she moved through a space. He turned.

The dress was dark green, fitted through the body, a cut that didn’t need decoration because the structure did everything. Her hair was down, which he hadn’t seen before, and it changed her face slightly — less boardroom, same authority.

She moved through her own event with ease of a person who had organized it and could therefore ignore it.

She reached him and looked him over once.

"You’re here," she said.

"You invited me."

"People don’t always come to things they’re invited to." She took a glass from a passing tray. "You look appropriate."

"High praise."

"It is, actually." She turned slightly, orienting them both toward the room. "I want to introduce you to a few people before dinner. Finance first — there’s a man named Carver who sits on three boards that would be relevant to you in eighteen months. I want him to know your face before you need to ask him for anything."

"Efficient," Ryan said.

"That’s the point of these evenings." She started moving and Ryan fell into step beside her. "How is the documentation coming."

"Two signatures away."

"Good. My attorney will have the final version to yours by end of week." She navigated them around a cluster of people near the bar. "The IRS interview — you’re prepared."

"As prepared as I can be."

"You’ll be fine. The paperwork is clean. Answer the questions you’re asked, don’t answer questions you weren’t asked, and don’t try to be charming." She glanced at him. "Save that for rooms where it’s an asset."

Ryan looked at her. "Is this not one of those rooms?"

"This is a room where competence is the asset." She stopped. "Carver."

Carver was a compact man in his sixties with the handshake of someone who had been told handshakes mattered and had taken that seriously his entire adult life.

Ryan matched it.

They talked for six minutes — Diana providing context, Ryan providing enough to be interesting without oversharing, Carver asking two questions that were smarter than his appearance suggested and getting answers that appeared to satisfy him.

After Carver there was a woman named Beth who ran a media foundation and who asked Ryan three questions about the product with focused curiosity, like a person who had experienced the problem personally. He answered them properly.

She gave him a card.

There was a senator whose name Ryan recognized and whose handshake was practiced in a different way than Carver’s — warm, held slightly too long, the grip indicating interaction was also a transaction. Ryan smiled and said the right amount of nothing.

They were moving toward the dining area when Diana stopped.

"My husband," she said.

The man walking toward them was somewhere in his late forties, possibly early fifties, a building showing he was athletic once and maintained enough of it to remember.

His tuxedo was correct. His expression depicting he attended enough of his wife’s professional events to have developed opinions about them.

"Richard," Diana said. "This is Ryan Russo. He’s the founder I mentioned — Rebuild Tech."

Richard Lockridge looked at Ryan with an assessment that was less evaluative than it was dismissive — like completing a formality.

"The startup," Richard said.

"That’s right," Ryan said.

"Diana mentioned." He took a drink from his own glass. "What stage are you at."

"Early. We’re building toward an MVP in the next ten weeks."

"So pre-revenue."

"Correct."

"And Diana’s putting money into that." He said it to Ryan but it was directed sideways, toward Diana, a remark that wasn’t a question.

"Richard has strong opinions about early stage investment," Diana said, with even delivery. She had said a version of this sentence many times.

"I have opinions about risk," Richard said. "Most startups fail. The statistics aren’t subtle about it."

"Most do," Ryan agreed. "The ones that don’t tend to change industries."

Richard looked at him. "That’s a thing founders say."

"It’s also a thing that’s historically accurate."

A beat.

Richard smiled with his mouth. "Well. Good luck with it." He put a hand briefly on Diana’s shoulder — proprietary, barely conscious. "I’ll find the table."

He moved away.

Ryan watched him go.

"He’s protective of the firm’s capital," Diana said.

"Is that what that was."

Diana looked at him with something close to amusement. "Come. Dinner."