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Mark Cuban Says AI Will Mint the Next ‘Trillionaire in the Basement’

Mark Cuban Says AI Will Mint the Next ‘Trillionaire in the Basement’

Mark Cuban thinks the world’s next Elon Musk won’t be a product of some big tech company, but a scrappy entrepreneur perhaps assisted by a team of AI agents. “There’s no better time to be an entrepreneur than right now,” he told The a16z Show. “There will be the trillionaire in the basement.”

The opening exists, he says, because most companies are slow to adopt AI and their leaders don’t understand it. Until the C-suite gets it, Cuban says, those organizations will struggle.

To show how exposed big brands are, he sat down with the head of a consumer food company and asked ChatGPT to create a competitor to its best-selling cookie. About three minutes later, the exec was swearing.

Still, Cuban says AI can’t do it alone. It’s book smart but not street smart, so it needs a human entrepreneur guiding it.

Mark Cuban thinks the world’s next Elon Musk won’t be a product of some big tech company, but a scrappy entrepreneur perhaps assisted by a team of AI agents. “There’s no better time to be an entrepreneur than right now,” he told The a16z Show. “There will be the trillionaire in the basement.”

The opening exists, he says, because most companies are slow to adopt AI and their leaders don’t understand it. Until the C-suite gets it, Cuban says, those organizations will struggle.

To show how exposed big brands are, he sat down with the head of a consumer food company and asked ChatGPT to create a competitor to its best-selling cookie. About three minutes later, the exec was swearing.

Still, Cuban says AI can’t do it alone. It’s book smart but not street smart, so it needs a human entrepreneur guiding it.

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Opinions expressed by Entrepreneur contributors are their own.

For the past two years, entrepreneurs have been duct-taping together AI automations — Zapier here, prompts there — hoping nothing breaks at 2 AM.

But the AI landscape is shifting from automation to autonomy.

Instead of tools that need constant prompting, a new generation of AI agents can research, analyze, write, code and execute projects on their own — often running in the background while you sleep.

In this video, I break down 7 AI agents that solo entrepreneurs are using to replace entire departments.

Some function like digital project managers running multiple AI models at once.
Some operate inside your own files with full context. And one can literally build and deploy working software from a simple description.

What you’ll discover:

  • The AI system that can run multi-step business projects for hours without supervision.

  • A private AI assistant that analyzes hundreds of files and builds reports instantly.

  • The autonomous agent that keeps working even after you close your laptop.

  • The AI engineer that can build real software without hiring a developer.

  • A research brain trained entirely on your own documents and knowledge.

  • The AI browser that finds hidden leads, trends and opportunities online.

  • And the tool that turns your workflows into systems AI agents can run automatically.

Inside, I’ll also show you the exact prompts you can screenshot and deploy in your own business.

Because the real shift in AI isn’t just better tools. It’s entrepreneurs learning how to deploy AI workers instead of AI assistants.

The tools will keep getting smarter.

The real question is whether the people using them will.

The AI Success Kit is available to download for free, along with a chapter from my new book, The Wolf is at The Door.

For the past two years, entrepreneurs have been duct-taping together AI automations — Zapier here, prompts there — hoping nothing breaks at 2 AM.

But the AI landscape is shifting from automation to autonomy.

Instead of tools that need constant prompting, a new generation of AI agents can research, analyze, write, code and execute projects on their own — often running in the background while you sleep.

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Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

  • Identify the one problem your buyers care about most. Ask what prompted them to start looking for a solution, what problem they were most eager to solve and why solving it became a priority.
  • Ask what happened before they adopted your solution. How long did they spend on the problem? What mistakes occurred? What opportunities did they miss? What happened when they delayed fixing it?
  • Ask customers to walk you through how they handled the problem before finding your solution and what changed afterward. Then build your messaging around those specific improvements.
  • Interview customers about the concerns they had before purchasing. Ask what nearly stopped them, what reassured them and what information would have made their decision easier.

Your homepage has one of the most important jobs in marketing: convincing the right visitors that your solution is worth exploring.

Yet many companies struggle to turn website traffic into demos, trials or purchases. They invest in SEO, advertising and content to attract visitors, only to watch most of them leave without taking action.

Having spent more than a decade helping B2B companies improve their messaging as a product marketing executive and consultant, I’ve learned that the problem often starts with a misunderstanding of what buyers need to hear before they’re willing to take the next step.

Companies often explain their products from their own perspective. They highlight what they’ve built, everything their product can do and the benefits they assume customers care about. It often results in messaging like “The AI-native GTM platform powering Precision GTM at scale.”

But buyers have their own priorities, frustrations and concerns. If your homepage doesn’t address those, even a great product can struggle to convert.

Here are four common messaging mistakes and how to fix them.

1. You haven’t identified the one problem your buyers care about most

Many companies want their homepage to communicate everything their product can do. They try to capture multiple use cases, features and benefits in a single headline, hoping to appeal to as many potential customers as possible.

The result is often vague messaging that promises to “streamline operations,” “boost productivity,” “help your business grow,” or vague slogans like “We’ll take care of your accounting so you can focus on your business.”

These statements may have some truth, but they’re unlikely to resonate with someone facing a specific, urgent problem. When you try to communicate everything, you risk saying nothing compelling enough to make a buyer act.

Consider a project management platform for marketing agencies. Its homepage might promise to “streamline projects and improve team productivity” or some version of that. But customer interviews could reveal that agency owners are particularly frustrated by missed deadlines that damage client relationships.

Now the company has a more specific message to lead with: “Deliver every client project on time, without constantly chasing your team for updates.”

That message is more likely to capture the attention of an agency owner who’s tired of apologizing to clients for late work. It connects with a problem they’re experiencing and have a reason to solve.

In my customer research work, I often find that what companies think customers value most differs from what actually motivates them to look for a solution.

To find your strongest message, interview recent customers or prospects. Ask what prompted them to start looking for a solution, what problem they were most eager to solve and why solving it became a priority.

Look for the single problem or desired outcome that most consistently motivates your ideal customers to act. Lead with that message on your homepage. You can use the rest of the page to communicate everything else your product offers.

2. You haven’t shown buyers what they’re losing by doing nothing

Your biggest competitor isn’t always another company. Often, it’s the way your prospective customers already do things.

They might recognize the problem your product solves but have learned to live with it. Unless the cost of continuing becomes clear, they have little reason to make a change.

Imagine a software product that automates invoicing for agencies. Its homepage might say, “Automate invoicing and save time.” That’s a reasonable benefit, but it doesn’t fully communicate why the problem deserves attention.

Now consider the agency owner’s existing workflow. Project managers finish work, someone manually checks billable hours, invoices are created at the end of the month, and the finance team follows up on unpaid balances.

The consequences might include delayed invoices, missed billable work, slower payments and unnecessary administrative costs. These are much more compelling reasons to change.

Instead of simply promising automation, the homepage could explain how manual billing creates revenue leakage and cash flow problems.

To make the status quo feel costly, make its consequences visible.

Ask customers what happened before they adopted your solution. How much time did they spend on the problem? What mistakes occurred? What opportunities did they miss? What happened when they delayed fixing it?

Use their answers to communicate the business and emotional impact of the problem. Wherever possible, include real numbers, concrete examples and real-life anecdotes.

3. You’re highlighting the wrong benefits or making your solution hard to imagine

Even when visitors recognize the problem, they still need to understand how your solution will improve their situation.

Many homepages fall short here because they emphasize generic benefits or product capabilities without explaining how the product fits into the buyer’s actual workflow.

For example, an AI-powered customer support platform might highlight advanced language models, intelligent routing and automated workflows. But customer research might reveal that support managers primarily want to reduce the number of repetitive tickets their agents handle without compromising customer satisfaction.

They want to know which questions AI can resolve, when a human agent takes over and how the platform will connect with their existing help desk. The homepage should answer those deeper questions or help the reader easily find that guidance elsewhere on the website.

Rather than simply stating that the product “improves support efficiency,” it could walk visitors through a familiar scenario: A customer asks about an order, AI retrieves the relevant information, and the issue gets resolved without an agent getting involved.

A simple workflow illustration can make the value immediately understandable.

I’ve found that understanding a customer’s existing process is one of the most useful parts of customer interviews. It reveals not only which benefits matter but also which details buyers need to see before they can imagine using a product.

Ask customers to walk you through how they handled the problem before finding your solution and what changed afterward. Then build your messaging around those specific improvements.

4. You haven’t done enough to reduce the perceived risk of buying

Even when buyers see the value, they might hesitate because they’re uncertain about what happens next.

Will the product work for their business? Will implementation be difficult? Will their team actually use it? Can they trust your company to deliver? These concerns can prevent otherwise interested visitors from converting.

I frequently see websites use customer logos and testimonials as their main form of reassurance. Those elements help, but they don’t necessarily answer the specific questions making buyers hesitate.

A small business considering a new accounting platform, for example, might be far more concerned about migrating its financial data than whether the software has won an industry award.

Showing how migration works, explaining the support available and featuring a customer who successfully made the switch could do more to increase conversions.

The most effective reassurance addresses the risks your buyers actually perceive.

Interview customers about the concerns they had before purchasing. Ask what nearly stopped them, what reassured them and what information would have made their decision easier.

Use those insights to select the right customer stories, product demonstrations, guarantees, implementation details and FAQs for your homepage.

Your customers can tell you what your homepage is missing

Improving homepage conversions doesn’t always require a complete redesign, more persuasive copywriting or another round of A/B testing. Sometimes, the most valuable starting point is a handful of conversations with recent buyers.

Ask what problem made them look for a solution, why they couldn’t continue with their existing approach, what convinced them your product was right and what almost prevented them from buying.

Their answers can help you build a homepage that speaks to a real priority, makes the cost of inaction clear, demonstrates relevant value and gives visitors the confidence to take the next step.

That’s a much stronger foundation for conversion than guessing which headline or call to action might perform better.

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