I like entrepreneurial people; I like people who take risks.

Host: The tennis court was empty now — floodlights casting pale halos over the white lines, the net swaying gently in the evening breeze. The air smelled of rain and ambition — metallic, charged, full of ghosts. Beyond the fence, the city hummed, the sound of cars and courage mingling in the dark.

Jack stood near the baseline, hands in his pockets, his gray eyes tracking the court’s geometry like it was a map of life — full of rules, boundaries, and the occasional lucky shot. Jeeny sat on the bench, her legs crossed, hair loose, watching him with a kind of quiet affection that only long conversations could build. A single yellow tennis ball rolled to her feet, stopping with the stillness of a thought about to become a question.

Jeeny: (picking up the ball) “Billie Jean King once said, ‘I like entrepreneurial people; I like people who take risks.’”

Jack: (smirking) “Of course she did. You can’t change the game if you’re too afraid to lose the set.”

Jeeny: “Exactly. She wasn’t talking just about business. She meant life — the courage to step into uncertainty and make it yours.”

Host: The wind rose, rustling through the chain-link fence, a metallic whisper of motion. Somewhere distant, thunder grumbled, as if the gods themselves were warming up for a match of their own.

Jack: “Risk. The word everyone romanticizes until it ruins them.”

Jeeny: (grinning) “Or saves them.”

Jack: “Funny how both outcomes look identical at the start. You jump, and you don’t know if you’re going to fly or break.”

Jeeny: “That’s what she meant, Jack. Risk isn’t about knowing you’ll succeed. It’s about refusing to stay static.”

Jack: (turning toward her) “Easy for legends to say. She had talent. She could afford to risk it. The rest of us? We have bills.”

Jeeny: “Talent isn’t insurance. She took the biggest risk of all — being visible in a world that told her not to be. Women weren’t supposed to challenge men on or off the court. But she did — with a racket and a revolution.”

Host: The lights flickered, the court bathed now in uneven brilliance. The sound of the city below rose, like applause carried by wind. Jack walked to the net, resting his hands on it, his expression a mix of skepticism and admiration.

Jack: “So you think risk is virtue?”

Jeeny: “No. Risk is truth. You find out who you are when you step off the line.”

Jack: (quietly) “And when you lose?”

Jeeny: “Then you learn. The losses refine the courage. Every failure tightens your aim.”

Host: The rain began, light at first, dotting the surface of the court with dark freckles. The droplets sparkled under the lights, each one a tiny moment of bravery falling from the sky.

Jack: “You know, risk-takers are the ones who burn out first. The world loves them until they fall. Then it pretends not to know them.”

Jeeny: (softly) “Maybe. But they exist fully for as long as they burn. That’s more than most can say.”

Jack: “You sound like you admire madness.”

Jeeny: “No. I admire conviction. There’s a difference.”

Host: The rain intensified, drumming on the bleachers, running down the painted lines like rivers on a map. Jack stood still, letting it soak him. Jeeny remained seated, face lifted toward the sky, eyes closed, the water sliding down her cheeks like tears she didn’t own.

Jack: (after a long silence) “You ever take a risk that scared you?”

Jeeny: “Every time I tell the truth.”

Jack: “That’s not the same.”

Jeeny: (opening her eyes) “It’s exactly the same. Vulnerability is the purest form of risk. You offer the world your unguarded self, and you pray it doesn’t crush it.”

Jack: “And if it does?”

Jeeny: “Then you rebuild. That’s the entrepreneurial spirit she was talking about — not starting companies, but starting again.”

Host: The thunder cracked, rolling across the sky like applause from the unseen audience of fate. The world smelled of wet earth and adrenaline.

Jack: “So risk is the currency of the soul.”

Jeeny: “Yes. And fear is the tax.”

Jack: (half-smiling) “You and your metaphors.”

Jeeny: “Because metaphors are how we measure courage. No one remembers the people who never gambled their comfort.”

Jack: “You think Billie Jean knew she’d win when she played Bobby Riggs?”

Jeeny: “No. But she knew she had to play. That’s the difference between ambition and purpose. Ambition wants to win. Purpose needs to try.”

Host: The rain softened, leaving the court gleaming under the floodlights — wet, beautiful, and waiting. Jack picked up a tennis racket from the bench, spinning it absently in his hand.

Jack: “You know, sometimes I think fear’s the only honest emotion left. Everything else is pretending.”

Jeeny: (standing now, stepping closer) “Maybe. But courage isn’t pretending you’re not afraid. It’s acting while your hands still shake.”

Jack: “And if they never stop shaking?”

Jeeny: (smiling) “Then it means you’re still alive.”

Host: A silence stretched, rich and cinematic. The world slowed, the city’s glow flickering through the rain like heartbeats in fog.

Jack: “So what’s the real message then? From her quote?”

Jeeny: “That life rewards the ones who show up on their own terms. That to live safely is to live silently — and silence is its own defeat.”

Jack: “You sound like someone ready to risk everything.”

Jeeny: “I already have. That’s why I’m still here.”

Host: The camera of the soul pulled back, revealing the two figures — drenched but unbroken — standing in the glow of artificial light and real conviction. The court beneath them shone like glass, the lines between victory and defeat blurred by rain.

And as the night deepened, Billie Jean King’s words echoed, not just as praise for boldness, but as a manifesto for living:

That risk is not recklessness,
but recognition —
that life, like the game,
is played between courage and caution.

That the true entrepreneur
is not the one who profits,
but the one who dares.

That the world moves forward
because some souls
refuse to wait for permission.

And that every time we step to the line —
whether in business, love, or faith —
we gamble not with loss,
but with the chance
to become.

Host: The rain fell slower now, soft and rhythmic. Jack looked up, eyes half-closed, smiling faintly.

Jeeny watched him, her own smile mirroring his, the kind that said, without words —

To risk is to live. To live is to win.