Billionaire Cashback System: I Can't Go Broke!-Chapter 52: Teasing

He made a comment about the foundation’s new grant recipients that was designed to be funny at the recipients’ expense and landed with most of the table how people laugh because the speaker expects it.

Diana refilled her wine again.

Ryan watched this quietly. He ate the course in front of him and kept his expression interested and said nothing that invited Richard’s attention.

That lasted about four minutes.

"The mid-market play is interesting in theory," Richard was saying, to no one in particular and therefore to everyone, "but the challenge is that mid-market companies don’t have the IT budget to justify enterprise tooling. You end up in a gap — too complex for SMB pricing, too small for enterprise deal cycles." He reached for his own glass. "It’s a crowded graveyard."

The table was listening with polite engagement - people who didn’t know enough about the subject to agree or disagree and weren’t going to commit either way.

"Most of the products in that gap built themselves into it," Ryan said. "They started enterprise and tried to scale down. We’re going the other direction."

Richard looked at him. "Product-led."

"Yes."

"Free tier."

"Yes."

Richard made a sound that communicated he had heard this before and the people who’d said it previously were no longer in business. "The problem with product-led in the mid-market is the champion problem. You need someone inside the company to drive adoption upward. Mid-market doesn’t have the internal political structure to support that."

"That’s been the failure point for tools that require the champion to sell the product," Ryan said. "Bridge removes that. It integrates passively — maps how the team actually works before it touches anything. By the time leadership sees it, it’s already running."

"So you’re banking on it spreading organically."

"We’re building for it."

Richard nodded slowly, expression granting a point he didn’t fully grant. "And the team building this is — how large."

"Five, currently."

"Five." He said it the way you repeat a number you find small. "And Diana thinks this is worth nearly a million dollars." He said it pleasantly, a pleasantly that is performing pleasantness for the table while meaning something else, his eyes moving briefly to his wife.

Diana looked at her glass.

"Diana’s track record on early-stage calls is better than most firms twice her size," Ryan said.

"Her track record is excellent," Richard agreed. "I’m just noting the profile of this particular bet." He smiled. "I suppose that’s what makes markets. Disagreement."

He turned to the man on his right and began a different conversation, leaving Ryan holding the thread of the last one with nowhere to attach it.

Ryan looked at Diana.

She was looking at the centerpiece. The candle in it had burned down about an inch since they’d sat. She was on her third glass since Richard had arrived.

Ryan refilled his own glass and sat back.

---

At some point in the next thirty minutes — during a conversation about city development that Ryan participated in enough to remain present — he felt it.

A pressure against his knee.

Light, brief, and then gone.

He didn’t look over. Diana was watching the man across from her explain something about a waterfront development deal. Her expression was attentive, responsive, appropriate. She said something that made the man nod enthusiastically and continued the conversation.

Ryan held still.

He was almost certain he had imagined it.

Then it happened again.

Her leg against his, her thigh pressing into his knee with a quiet, steady pressure, and this time it didn’t move away immediately. It just stayed there, warm and intentional, her knee against his beneath the tablecloth, invisible to everyone including the two of them if they kept looking forward.

She didn’t look at him.

He didn’t look at her.

Richard was talking again — he had looped back into the conversation from the right, bringing a new subject and a new audience.

Ryan couldn’t immediately track what he was saying because the warmth of Diana’s leg against his knee had redirected a significant portion of his attention, but he kept his expression neutral and his posture unchanged and let the ambient sound of the room wash over him until Richard’s voice resolved into words.

"— and Ryan, actually, since you’re here —"

Ryan looked up.

"—we’re doing a round of golf Saturday morning. Ridgemont. Small group, usually just a few of us." Richard’s eyes had the light of a man enjoying the setup of something. "You should come."

"I’d be glad to," Ryan said.

Richard’s mouth curved. "Good. We tee off at eight, so it’s an early start. Do you play much?"

The question landed on the table. A couple of the other men in the conversation perked up slightly — one of them glanced at Ryan’s hands, or his suit, or something about him that indicated they were also interested in the answer.

"Not particularly," Ryan said.

Richard smiled. "I’ll have someone pair you up with a caddie, then. We can walk you through it." He said it to the man next to him, not to Ryan. "Always good to get fresh blood on the course. Assuming they can keep up." The man next to him laughed how people laugh at things that aren’t quite jokes until they’re said by the right person.

Diana’s leg pressed once more against his knee, and held there.

Ryan looked at Richard — the easy grin, the glass raised in a kind of ambient self-satisfaction, the entire posture of a man so settled in his position that he’d stopped checking whether people could see him from where he was standing.

"I’d love to," Ryan said. Warm, agreeable, without hesitation. 𝚏𝕣𝐞𝗲𝐰𝕖𝐛𝐧𝕠𝕧𝚎𝚕.𝐜𝚘𝗺

Richard nodded and moved the conversation on.

Ryan turned back to his plate.

He picked up his fork and cut into what was in front of him, and somewhere under the table Diana’s knee stayed exactly where it was, and Ryan chewed slowly and thought:

’Let’s see if you’re still this smug after I’ve fucked your wife.’

He took a sip of wine.

The dinner continued.