If Mark Cuban Were a Gen Zer Today, Here’s How He’d Crush It (Even While Sleeping)

magine Mark Cuban—serial entrepreneur, Shark Tank legend, and billionaire—starting fresh as a Gen Z kid in 2025. No fortune, no fame, just a laptop, an internet connection, and a relentless drive to figure shit out.

What would he do to get ahead of the game?

Spoiler: he’d be all over AI, hustling smarter than anyone else, and probably still failing at selling powdered milk (true story). Here’s how Cuban would play it if he were 16, 18, or 21 today—and how you can, too.

Step 1: Obsess Over AI, 24/7 (Yes, Even While Sleeping)

If Cuban were a Gen Zer, he’d be living AI. “I’d spend every waking minute learning about it,” he says, “and even when I’m sleeping, I’m listening to podcasts talking about AI.”

Picture this: he’s got AirPods in, drifting off to episodes about ChatGPT, Perplexity, or Anthropic’s Claude, soaking up knowledge like a sponge.

Why? Because AI is the ultimate equalizer—it’s gone from “$5,000 for a clunky PC” back in the day to “a laptop and Wi-Fi can start anything” now. Today, AI is your mentor, your assistant, your sales team, all rolled into one.

Takeaway for you: Dive in. Follow AI hacks on TikTok and Instagram until your feed’s nothing but tech gold. Listen to podcasts like The AI Breakdown or Lex Fridman—even on loop while you crash. Knowledge is power, and AI’s changing so fast you can’t afford to blink.

Step 2: Fail Fast, Fail Often (But Learn From the Powdered Milk Fiasco)

Cuban’s first hustle after college? Selling powdered milk. “It doesn’t taste quite as good as milk, but it’s cheaper,” he thought. Spoiler: nobody bought it. “It was stupid,” he admits, “but I had to learn it was stupid.”

The lesson? Failure’s fine—nobody remembers your flops. “You only gotta be right one time,” he says, “and then everybody calls you a genius.”

For Gen Z Mark, this means trying dumb ideas—like pitching AI-generated sock puppets on Etsy—and bombing spectacularly. But each flop teaches you something. Maybe the sock puppets suck, but the AI video tool you used sparks a better idea.

Takeaway for you: Don’t be afraid of stupid ideas. Test them, crash, and pivot. Just don’t pitch Cuban powdered milk 2.0—he’s over it.

Step 3: Leverage AI Tools to Amplify Everything

Here’s where Cuban’s Gen Z hustle gets wild. He’d be all over tools like NotebookLM, which turns PDFs into podcasts. “You can take any text—onboarding manuals, sales pitches, whatever—and it spits out a podcast,” he marvels.

Imagine him feeding a Shark Tank pitch into it, sending it to investors as a slick audio file. Or walking into small businesses, demoing how they can turn their car lot inventory into a podcast for $25 a pop. “It’s insane,” he says, “and it’s right there.”

AI doesn’t just stop at podcasts. It writes emails, makes sales calls, spiders data—leaving you to focus on the big picture: product-market fit, creativity, the stuff machines can’t dream up. “AI amplifies whatever skills you have,” Cuban says.

Creative? It won’t write a killer story for you, but it’ll crank out drafts so you can polish the gold.

Takeaway for you: Play with tools like NotebookLM, ChatGPT, or Gemini. Demo them to local businesses—charge for it. Use AI to cut the grunt work and double down on what you’re good at.

Step 4: Hustle While Everyone Else Sleeps

Cuban’s blunt: “99.99999% of people aren’t going to do shit.” They’ll wait for someone to hand them a playbook.

Not Gen Z Mark. He’d be the kid hitting every store on Main Street, showing off AI demos, making $25 an hour while others scroll X. “Those who put in the time are going to crush it,” he says. AI’s the rocket fuel, but you’ve gotta light the match.

Takeaway for you: Don’t wait. Start small—sell an AI service, build a side hustle, anything. The tools are there; the edge goes to whoever uses them first.

Step 5: Think Like Gen Z (Because You Are)

Cuban gets it: Gen Z doesn’t read manuals—they listen to podcasts, watch YouTube, scroll TikTok. “You have to understand how your stakeholders consume info,” he says.

If he were 21, he’d meet people where they’re at—turning boring docs into audio, videos, or bite-sized content. It’s not just about building a business; it’s about hacking attention.

Takeaway for you: Know your audience. If they’re on TikTok, make TikToks. If they’re podcast nerds, feed NotebookLM your pitch. Speak their language, and they’ll listen.

The Bottom Line: AI + Grit = Unstoppable

If Mark Cuban were a Gen Zer, he’d pair relentless curiosity with AI’s insane potential. He’d fail, learn, and fail again—then hit it big. “Whatever intelligence you have, AI can clean out the noise so you can focus,” he says.

It won’t replace your creativity or hustle, but it’ll amplify them. And in a world where 70 million Gen Zers are chasing the entrepreneurial dream, that edge matters.

So, channel your inner Cuban. Learn AI like your life depends on it (it kinda does). Embrace the stupid ideas. And hustle while everyone else is sleeping—because when you’re right just once, they’ll all call you a genius.