Why Mark Cuban Says Now Is the Best Time to Start a Business (Especially If You're Broke)

“You only have to be right one time.” – Mark Cuban

In a wide-ranging interview with Emma Grede on Aspire, Mark Cuban peeled back the curtain on what it really takes to build a business that lasts — and why most people just aren’t cut out for it.

From selling garbage bags at age 12 to flipping a tech company for $5.7 billion, Cuban’s journey isn’t just about ambition — it’s about adaptation, relentless learning, and brutal honesty. For anyone stuck between wantrepreneur and entrepreneur, this is your wake-up call.

From Pittsburgh Grit to Startup Glory

Cuban didn’t inherit an empire — he hustled for it. Growing up in a working-class family in Pittsburgh, his father repaired car upholstery. His mom bounced between odd jobs.

“If you wanted something, you had to earn it,” Cuban recalled.

That mindset kicked in early. At 12, when he asked for basketball shoes, his dad's friend handed him a stack of garbage bags and told him to sell them door-to-door. That side hustle became Cuban’s first real taste of entrepreneurship.

“Once you learn how to sell and talk to people, you always have the ability to make money.”

The Power of Getting Fired (And Betting on Yourself)

By 24, Cuban had bounced between jobs, slept on the floor in a three-bedroom apartment with six roommates, and was just trying to make rent. When his boss fired him for closing a deal instead of opening the store, Cuban realized something crucial:

“I’ve got to control my own destiny.”

So he started MicroSolutions — a scrappy tech consulting company — and worked seven years straight without a vacation. His first exit came when he sold it to H&R Block. Then, with a few million dollars in hand, Cuban didn’t start a yacht club. He went back to work.

Broadcast.com: Betting Big Before the World Was Ready

Before Spotify. Before YouTube. Before live streaming was even a phrase, Cuban and business partner Todd Wagner launched AudioNet (later broadcast.com), the first company to stream radio and video online.

“If this works the way I think it will, this company is worth five billion dollars.”

Spoiler: it did. Broadcast.com IPO’d in 1998 and was acquired by Yahoo for $5.7 billion in 2000. Cuban protected his stock with a collar — a sophisticated financial hedge — and walked away a billionaire.

But don’t let the number distract you. The real lesson was Cuban’s obsessive, edge-of-insanity work ethic.

“I’d look up and 25 hours would’ve passed. I was coding nonstop, eating ribs and wiping my hands on towels. It was gross — but it worked.”

On Shark Tank and the Myth of Overnight Success

Cuban’s 15 seasons on Shark Tank weren’t about the glitz.

“People think you’re going to make money automatically. But most people don’t make it. It’s hard.”

He stayed on the show for the same reason he started selling: to show what was possible.

“You cannot be what you don’t see.”

His advice on the show was blunt, not because he didn’t care — but because he did. Founders walked in scared, hopeful, sometimes overconfident. Cuban gave them the truth, whether it came with a check or not.

The Founder’s Filter: Can Everyone Be an Entrepreneur?

“Can anyone be a founder?” Grede asked.

Cuban didn’t hesitate.

“Can they? Yes. Should they? No.”

He broke it down simply: if you crave structure, if you’re not ready to grind, if you think hiring someone will solve all your problems — entrepreneurship isn’t for you.

“You’ve got to be the bullet.”

Founders must sell. They must learn. They must obsess. Cuban’s barometer is brutally simple:

• Do you dream about your business?
• Do people actually buy what you’re selling?
• Are you willing to do the work yourself, even when it’s hard, messy, or terrifying?

No money? No excuse.

“If I had nothing right now, I’d be all about AI. Just like I taught myself to code, I’d teach myself this.”

Why Now Is the Best Time to Start — But Also the Most Competitive

Cuban believes 2024 is a once-in-a-generation opportunity for startup founders. Why? AI.

“Right now, there’s no better time to be a startup entrepreneur. You have an expert in your pocket.”

Cuban is obsessed with AI tools like ChatGPT and Gemini. He uses them to test business ideas, write plans, create mockups — and encourages every entrepreneur to do the same.

But here’s the twist: the barrier to entry is gone. That means more competition, not less.

“You might be broke. But now, you’ve got no excuse.”

Sales Cures All

Forget raising capital. Forget the perfect product. Cuban is clear:

“Sales cures all. No sales, no company. That’s it.”

People avoid sales because they fear rejection. Cuban doesn’t.

“Every no gets you closer to a yes.”

That mindset drove him when he sold magazines, built software, pitched investors — and it's what he still teaches to Shark Tank hopefuls today.

Legacy, Not Retirement

You’d think a billionaire would be content coasting. Not Cuban.

“I’m just getting started. Don’t let the wrinkles fool you.”

He’s not chasing more money. He’s chasing impact. And if you’re wondering what separates those who talk about starting from those who actually do?

It’s not intelligence.

It’s not funding.

It’s not luck.

It’s this: execution, obsession, and an unshakable willingness to figure it out.

TL;DR — Mark Cuban’s Rules for Entrepreneurs

• If you can’t sell it, it’s not a business.
• Learn AI like your livelihood depends on it — because it does.
• Don't chase structure. Chase problems worth solving.
• Do the work. No one’s coming to save you.
• Every no brings you closer to a yes.
• You only need to be right once.