You provide Mark Cuban with a cell phone, $500, and drop him in the middle of nowhere, and he’d be on top again in no time. That is not a motivational poster; that is literally his plan.
During a recent interview with Wired, billionaire entrepreneur was asked what he would do if he were beginning his fortune anew. The question invigorated him.
“That’s the best question I’ve ever been asked in the course of my entire adult life,”
Cuban replied with a smile. And then he gave his answer, fast and forceful: get a sales job. Any sales job.
“I’m really, really, really good at sales. If I’ve got my last $500, and I’ve got nothing but a phone, I’m gonna get that job and I’m gonna know more about that business than anybody on earth.”
Sounds like a straightforward flex? Maybe. However, this is from the individual who sold his first business for $6 million and his second for an eye-popping $5.7 billion. It wasn’t luck. It was a sale.

Gage Skidmore from Peoria, AZ, United States of America, CC BY-SA 2.0, via Wikimedia CommonsRestoring the Empire From the Ground Up
Cuban’s return to theory shines and is unforgiving. He’d get a sales job first. Then, for three months, he’d drive his commissions to their absolute limits and build a portfolio of success.
Having established himself as the top closer, he’d present himself to his boss with an ultimatum.
“Three months in, when I’ve proved that I’m the best salesman this company has ever had, I’m going to sit in my boss’s office and I’m going to say: ‘You’re going to pay me this amount to keep me, or I’m going to go out and start my own company selling this stuff.'”
That is: define your value, then build on that.
Career experts agree. The Mullings Group CEO, Joe Mullings, a career coach, once told CNBC that the best time to ask for a raise is when you have proof to back up your request.
“Bring your achievements, what would be lost to the organization if you left, and what it would cost to replace you,” Mullings suggested.
Cuban’s strategy is not just hustling for a paycheck. It’s using evidence of performance as a stepping stone to control, power, and eventually, ownership.
Why Sales Skills Are the Ultimate Power Tool
Most people think about sales as some sort of special art reserved for cold callers and commission junkies. Cuban doesn’t. “Everything always comes back to sales,” he told Wired.
It’s not just about discovering someone to put their name on the dotted line. It’s timing, communication, empathy, and convincing. It’s convincing a hiring manager that you’re the one for the job, or convincing your team to gamble on your wild idea.
Cuban’s catchphrase: Sales is life. And he has been living it since he was a kid.
From Garbage Bags to Billions
By age 12, Cuban was selling trash bags door-to-door in Pittsburgh. He had the golden rule mastered early: don’t waste people’s time. His presentation? Just 14 seconds.
“Hi, my name’s Mark. You need some garbage bags? I can give you a fair price, and when you need garbage bags again, you just call me and I’ll toss ’em in the back of my wagon and bring ’em straight to your door,” he told GQ.
Flash ahead a couple of decades, and the same impulses helped Cuban launch MicroSolutions, a computer consulting firm, which he later sold to CompuServe for $6 million. That was followed by Broadcast.com, an audio streaming site, which Yahoo acquired for $5.7 billion.
Both exits had one thing in common: Cuban knew how to sell.
Helping Over Hustling
There is a twist to Cuban’s sales gospel, though. He doesn’t believe in manipulation. “Selling is not persuading,” he said in an interview on TikTok. “It’s assisting.”
That’s motivational fluff, but it’s what is at the heart of how he operates. Find out what people really need. Then be the person to get it done.
“When you understand what people want and need, you’re in a position to help them,” he said. “You then do good things, make deals, and that’s the way you build companies.” The key is to become indispensable.
Practice Like a Pro
Cuban isn’t all flash and bravado. He’s obsessed with getting repetitions in. His own strong work ethic was partly inspired by basketball legend Dirk Nowitzki.
In an interview with CNBC, Cuban described how he admired Nowitzki’s relentless practice schedule and applied the same principle to business.
“Dirk never stopped practicing. Dirk never stopped working on his shot. What that instilled in me is that knowing how to do something is not enough. You have to continue doing it until you absolutely can’t do it incorrectly.”
For Cuban, sales mastery is not a one-time achievement. It’s a skill set that adds up over a lifetime.
The Cuban Playbook: Sell, Scale, Repeat
So, what can we learn from this for the rest of us?
- Learn to sell – Whether you’re selling garbage bags, computer software, or your own personal brand, being able to communicate value is a superpower.
- Monitor your wins – Cuban doesn’t simply work hard; he measures results. You should as well.
- Capitalise on success – Once you have proved that you can deliver, use it to negotiate more favorable terms or establish on your own.
- Be of assistance, not aggressive – Find out what individuals need and guide them toward it. That is true selling.
- Outwork everybody – Show up, learn the business, and work the hours that other people won’t.
The good news? You don’t even need to be a billionaire to begin any of this. Cuban asserts that selling is something that anyone can learn. Indeed, he believes it’s the best investment you’ll ever make.
“It doesn’t matter where you begin,” he told me. “If you can sell, you can create something. And if you can create something, you can change everything.”
So the next time you grumble when you hear the word “sales,” just remember the following: it is not just a career. It can be your ticket to freedom.
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