You learn in this business: It you want a friend, get a dog.

Host: The night had long settled over the city, wrapping its buildings in a thin, glassy silence. The skyscrapers stood like tired gods, their windows glowing with the artificial heartbeat of men who refused to sleep.

In one of those towers, a single office still burned with light. The clock read 11:47 PM.

The rain dripped steadily down the wide glass pane, slicing the reflection of two people in half — Jack, standing by the window, his grey suit rumpled, tie loosened, and Jeeny, sitting across a sleek mahogany desk, papers spread before her like a battlefield.

The air was heavy with the scent of coffee, tension, and the faint metallic whisper of regret.

Jeeny: without looking up “You know what Carl Icahn once said? ‘You learn in this business: If you want a friend, get a dog.’”

Jack: dryly “Yeah. And he made billions proving it.”

Host: Jack’s voice carried that familiar edge — part sarcasm, part fatigue. The city’s glow painted his face in pale gold, his expression unreadable, carved out of years of fighting, winning, and losing.

Jeeny: “You say that like it’s something to be proud of.”

Jack: “It is. Friendship is a liability in this world, Jeeny. The minute you start confusing people with partners, you lose leverage.”

Jeeny: leans back “And what’s left when all the leverage is gone? You stand on top of the mountain, alone, wondering why the wind sounds like your own voice echoing back.”

Jack: “That’s the price of being right.”

Jeeny: “No, Jack. That’s the cost of being empty.”

Host: The light from the desk lamp flickered, catching the silver of Jeeny’s pen as she twirled it between her fingers — slow, deliberate, a rhythm of thought.

Jeeny: “You think Icahn meant that quote literally? He wasn’t praising loneliness. He was warning about it.”

Jack: “He was being honest. Business isn’t therapy, Jeeny. You don’t come here to make friends. You come here to survive.”

Jeeny: “But survive for what? To prove you can?”

Jack: smirks “To win.”

Jeeny: “And what’s winning if you lose your humanity getting there?”

Host: Her words hung between them, sharp and soft all at once. Outside, a flash of lightning broke through the clouds, washing the glass with white for an instant — a strobe of clarity neither could ignore.

Jack: “You think kindness gets you anywhere in this business? I’ve seen people get destroyed because they trusted the wrong smile. Deals collapse, partners vanish, loyalty evaporates the second someone sees a bigger margin. You learn fast — or you bleed slow.”

Jeeny: “Then maybe you’ve spent too long mistaking cynicism for wisdom.”

Jack: “And maybe you’ve spent too long mistaking hope for strategy.”

Host: The rain grew heavier, drumming against the glass like an impatient metronome. Jeeny stood, crossing to the window beside him. Their reflections merged in the pane — one silhouette hardened by experience, the other softened by empathy.

Jeeny: “You know who else said something like that? Gordon Gekko, in Wall Street. And that film wasn’t supposed to be a manual.”

Jack: chuckles lowly “Maybe not. But it became one anyway.”

Jeeny: “Yeah, for people who confuse greed with intelligence.”

Jack: “Greed’s just a word people use when they can’t keep up.”

Host: She turned to him sharply. Her eyes — deep, tired, but still burning — met his.

Jeeny: “No, Jack. Greed’s what happens when the soul forgets how to measure anything but gain. You think Icahn never had friends? He did. But he knew they weren’t tools. That’s what makes the quote ironic — not cruel.”

Jack: “You’re giving him too much credit.”

Jeeny: “And you’re giving up too easily.”

Host: The clock ticked, loud now in the silence, each second sounding like a deal closing, another bridge burning.

Jack: quietly “You ever been betrayed, Jeeny? Not in theory — in the real way. The kind that guts you? Because I have. The kind that teaches you that trust is just a setup for disappointment.”

Jeeny: “Yes.”

Jack: turns “Really?”

Jeeny: “Of course. But I didn’t let it turn me into the thing I hated.”

Host: The air in the room seemed to thicken. Jack’s hand tightened around his glass of whiskey, his knuckles white against the amber light.

Jeeny: “You think you’re protecting yourself by staying cold, but all you’re doing is freezing from the inside out. And one day, you’ll look around and realize you’ve built a fortress with no doors.”

Jack: “That’s fine. I prefer the quiet.”

Jeeny: “No, you don’t. You mistake the silence for peace because you’ve forgotten what real connection feels like.”

Host: He didn’t answer. His jawline tightened, his eyes locked on the city below — a thousand lives flickering like data points.

Jeeny: “Tell me something. When’s the last time you called someone just to talk? Not for advice. Not for business. Just... to hear their voice.”

Jack: long pause “Does the pizza guy count?”

Jeeny: smiles sadly “You’re impossible.”

Jack: “No, just realistic.”

Jeeny: “You’re scared.”

Host: That landed. The room fell still, except for the sound of rain, whispering against the glass like a quiet accusation.

Jack: “Scared of what?”

Jeeny: “Of being needed. Because the moment someone needs you, you’re no longer in control.”

Jack: low, almost to himself “Control’s all that’s left when trust runs out.”

Host: Jeeny stepped closer, the lamplight catching her face — calm, patient, but with that flicker of defiance she never lost.

Jeeny: “Then maybe control isn’t strength. Maybe it’s armor for people who forgot how to heal.”

Jack: laughs softly “You talk like the world runs on feelings. It doesn’t.”

Jeeny: “No. It runs on people. And people feel, whether you like it or not.”

Host: He turned to her fully now, and for a moment the veneer cracked. Beneath the sarcasm was something raw — exhaustion, maybe, or loneliness that had finally grown too loud to ignore.

Jack: “You really believe you can survive in this business and keep your heart intact?”

Jeeny: “No. But you can survive without losing your soul.”

Host: She reached for her bag, sliding her papers inside, her voice soft now.

Jeeny: “You don’t need to befriend everyone, Jack. But you could stop confusing friendship with weakness.”

Jack: “And you could stop confusing success with virtue.”

Jeeny: “Fair.” pauses “But tell me something — when this is all over, when the deals are done and the screens go dark... who’s left in your corner?”

Jack: after a long silence “Maybe that’s why I like dogs.”

Jeeny: smiles faintly “Then maybe you should get one.”

Host: Her heels clicked softly as she headed for the door. Jack watched her go — the light catching her reflection in the glass, slowly fading as she disappeared into the hall.

He turned back toward the window, the rain still falling, the city alive and merciless.

For a moment, his hand drifted to his phone — to a contact he hadn’t called in years. He hesitated, then set it down again.

The clock struck midnight.

Host: And in that fragile stillness, between ambition and loneliness, between empire and emptiness, Jack understood the quiet truth of Icahn’s warning —

That in the business of power, trust is expensive, loyalty rare, and friendship a risk few can afford.

Yet somewhere deep beneath the armor, a small, honest thought flickered —

Maybe the real victory isn’t in standing alone.
Maybe it’s in remembering who you’d still want beside you when the deals stop and the city sleeps.

The rain eased. The lights dimmed. And in the glass, Jack’s reflection stared back —
a man who had everything but company,
and the faintest echo of a smile that said,
Maybe tomorrow, I’ll call.