Would You Buy $1 for 50 Cents From Mark Cuban? The Billionaire Explains the Power of Salesmanship

Businessman MARK CUBAN speaks at a small business roundtable for the Kamala Harris for President campaign in Phoenix, Arizona.
Gage Skidmore/ZUMA Press Wire / Shutterstock / Gage Skidmore/ZUMA Press Wire / Shutterstock

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Mark Cuban’s recent statement that “Democrats can’t sell worth s***” went viral due to its political implications, but it also underscores the billionaire’s broader philosophy. Having a great idea isn’t enough — you have to know how to sell it. While his comments sparked debate, the core message reflects a fundamental business truth: the ability to sell can make or break success.

If there’s one thing Mark Cuban knows inside and out, it’s the value of salesmanship. The entrepreneur and “Shark Tank” star may have made his fortune by investing as well as founding and selling tech companies, but he became famous by establishing himself as an expert. Through the power of self-branding and promotion, he’s positioned himself as the go-to guy to comment on business strategy, innovation, and even politics. 

He also knows how people fail at the fine art of salesmanship. Often, they get bogged down by their own anxieties or become overly reliant on consultants. To illustrate the point, Cuban offered a simple analogy: Imagine a team tasked with selling dollar bills for 50 cents. Should be a slam dunk, right? Not if they waste time and money overanalyzing and hiring 50 consultants to handle what should be a simple job. 

Whether you’re looking to sell a product, a company, or even your own services, you’ve got to be a good salesperson. How do you get started? Cuban has some ideas. 

Help People Instead of Convincing Them 

In an interview with Randall Kaplan, host of the podcast “In Search of Excellence,” Cuban described one of his first big sales ventures, started when he was 12 years old. The entrepreneurial preteen went door to door among his neighbors, selling garbage bags. As soon as those doors opened, Cuban began his pitch with a simple question: “Do you use garbage bags?” 

Of course, the answer was always yes, but young Cuban didn’t immediately launch into a pitch about his bags being the best. Instead of going for the hard sell, he explained how his bags would make potential clients’ lives easier and more efficient. He started the conversation by talking about how he could help them, which made them more receptive to him and more interested in what he had to offer. 

Kaplan described Cuban’s philosophy as one rooted in service: “The art of selling is not a ruthless effort to force customers to buy your product — it’s about helping them realize that they have an unmet need, and that you can be the one to meet it.” 

Always Be Selling 

While “always be selling” doesn’t have quite the same ring to it that the more famous slogan “always be closing” does, it’s a core part of Cuban’s approach to being a good salesperson. He once said, “I’m continuously looking for ways to improve all my companies, and I’m always selling. Always.” 

You never know who your next customer, investor or even business partner might be, so you should be excited to talk about what you can offer whenever the opportunity arises. Now, this doesn’t mean channeling Saul Goodman with smarminess — it means recognizing potential prospects and constantly thinking about how you can bring value to others.

Understand Your Value 

You already know how awesome your product or service is, and you’re working hard to help other people know it, too. Part of selling yourself or your business to potential customers means understanding how you’re a cut above the competition. That requires researching your peers and assessing their strengths and weaknesses against your own. Be prepared to explain why you’re better equipped to address a client’s needs. 

Cuban wants you to differentiate yourself from other people in your field by demonstrating what you can provide that your competitors simply can’t. “When you’ve got 10,000 people trying to do the same thing, why would you want to be number 10,001?” he said. 

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