At 66 years old, Mark Cuban remains one of the most forward-thinking entrepreneurs in tech and finance. The billionaire who built his fortune through internet ventures like Broadcast.com in the 1990s is now doubling down on another technological revolution: artificial intelligence. Unlike many of his peers who dismiss new tech trends, Cuban has openly embraced AI as a cornerstone of his modern business strategy.
The Billionaire’s Practical AI Playbook
During a recent podcast appearance in June 2025, Mark Cuban revealed that he integrates AI tools into virtually every aspect of his professional and personal operations. For instance, he uses coding platforms like Replit to bridge skill gaps—while Cuban was once proficient in software development, years away from hands-on coding meant those abilities had atrophied. By leveraging AI, he rebuilt a pharmacy cost comparison tool that tracks price fluctuations across different vendors and automatically alerts him to changes, a critical asset for his healthcare company Cost Plus Drugs.
His video production workflow has also been transformed. Cuban now relies on AI-generated content for his Dallas Mavericks franchise and other business ventures, converting simple text prompts into finished video assets. Even his personal health management uses AI: he’s applied it to monitor medications and fitness routines while addressing specific health challenges.
Yet Cuban is cautious about AI’s current capabilities. He acknowledges that AI-generated outputs aren’t guaranteed to be 100% accurate and shouldn’t be blindly trusted. Still, he sees tremendous upside potential. His most audacious prediction: AI will enable someone—possibly working from a basement—to become the world’s first trillionaire by combining entrepreneurial creativity with AI’s computational power.
Why Average Investors Need AI, Not Just Tech Billionaires
The practical applications Cuban demonstrates aren’t exclusive to business moguls. Everyday investors can adopt similar AI strategies to make more sophisticated, data-driven financial decisions without necessarily being tech-savvy themselves.
However, a critical distinction exists between asking ChatGPT “which stocks should I buy?” and strategically deploying AI as a financial planning partner. According to Amy Chou, chief product officer and COO of Addition Wealth, the difference comes down to depth and context.
“Human advisors face a fundamental limitation: they can’t store and instantly recall every document, conversation, and nuance from your financial history. AI systems, by contrast, retain complete records of your goals, previous decisions, uploaded documents, and even the trade-offs you’ve contemplated,” Chou explains. This memory advantage becomes especially powerful when parsing complex financial documents—employee stock option grants, workplace benefits materials, tax scenarios—areas where most people get stuck.
The Collaboration Model: AI as Your Financial Co-Pilot
The most effective approach isn’t AI operating independently, nor is it replacing human advisors entirely. Instead, it’s a hybrid model where AI and human expertise work in tandem.
Chou emphasizes that feeding AI contextual information produces far better results than one-off queries. “Generic questions yield generic answers. When you provide specific details and precise questions, AI can break down complex financial choices into understandable components,” she notes. As investors gradually share more financial details with their AI tools, the systems become increasingly proactive—flagging upcoming deadlines, identifying growth opportunities, and suggesting actions tailored to your exact circumstances.
The real power emerges when AI handles the analytical heavy lifting while humans navigate subjective, emotionally-charged decisions. Deciding whether to sell your home carries financial implications, but it’s equally a lifestyle choice that benefits from human judgment.
“Investors should be comfortable using AI when it’s supported by human oversight, not when it operates in isolation,” Chou advises. The ideal framework includes AI recognizing its boundaries and recommending when a qualified human advisor should step in—particularly during major life transitions or complex financial situations. Better still: AI can transfer your complete financial context to the advisor, transforming a typical 30-minute advisory session into a highly customized, efficient consultation that benefits both parties.
The Bottom Line
Mark Cuban’s approach to AI—experimental, practical, and integrated—mirrors what savvy investors should adopt. AI isn’t a replacement for financial wisdom or professional guidance, but it’s an increasingly essential tool for anyone serious about building and protecting wealth. Whether you’re optimizing investments or managing health data, the principle remains the same: AI works best when it augments human capability rather than replacing it.
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From Coding to Wealth: How Mark Cuban Leverages AI to Stay Ahead in Business and Why Investors Should Follow Suit
At 66 years old, Mark Cuban remains one of the most forward-thinking entrepreneurs in tech and finance. The billionaire who built his fortune through internet ventures like Broadcast.com in the 1990s is now doubling down on another technological revolution: artificial intelligence. Unlike many of his peers who dismiss new tech trends, Cuban has openly embraced AI as a cornerstone of his modern business strategy.
The Billionaire’s Practical AI Playbook
During a recent podcast appearance in June 2025, Mark Cuban revealed that he integrates AI tools into virtually every aspect of his professional and personal operations. For instance, he uses coding platforms like Replit to bridge skill gaps—while Cuban was once proficient in software development, years away from hands-on coding meant those abilities had atrophied. By leveraging AI, he rebuilt a pharmacy cost comparison tool that tracks price fluctuations across different vendors and automatically alerts him to changes, a critical asset for his healthcare company Cost Plus Drugs.
His video production workflow has also been transformed. Cuban now relies on AI-generated content for his Dallas Mavericks franchise and other business ventures, converting simple text prompts into finished video assets. Even his personal health management uses AI: he’s applied it to monitor medications and fitness routines while addressing specific health challenges.
Yet Cuban is cautious about AI’s current capabilities. He acknowledges that AI-generated outputs aren’t guaranteed to be 100% accurate and shouldn’t be blindly trusted. Still, he sees tremendous upside potential. His most audacious prediction: AI will enable someone—possibly working from a basement—to become the world’s first trillionaire by combining entrepreneurial creativity with AI’s computational power.
Why Average Investors Need AI, Not Just Tech Billionaires
The practical applications Cuban demonstrates aren’t exclusive to business moguls. Everyday investors can adopt similar AI strategies to make more sophisticated, data-driven financial decisions without necessarily being tech-savvy themselves.
However, a critical distinction exists between asking ChatGPT “which stocks should I buy?” and strategically deploying AI as a financial planning partner. According to Amy Chou, chief product officer and COO of Addition Wealth, the difference comes down to depth and context.
“Human advisors face a fundamental limitation: they can’t store and instantly recall every document, conversation, and nuance from your financial history. AI systems, by contrast, retain complete records of your goals, previous decisions, uploaded documents, and even the trade-offs you’ve contemplated,” Chou explains. This memory advantage becomes especially powerful when parsing complex financial documents—employee stock option grants, workplace benefits materials, tax scenarios—areas where most people get stuck.
The Collaboration Model: AI as Your Financial Co-Pilot
The most effective approach isn’t AI operating independently, nor is it replacing human advisors entirely. Instead, it’s a hybrid model where AI and human expertise work in tandem.
Chou emphasizes that feeding AI contextual information produces far better results than one-off queries. “Generic questions yield generic answers. When you provide specific details and precise questions, AI can break down complex financial choices into understandable components,” she notes. As investors gradually share more financial details with their AI tools, the systems become increasingly proactive—flagging upcoming deadlines, identifying growth opportunities, and suggesting actions tailored to your exact circumstances.
The real power emerges when AI handles the analytical heavy lifting while humans navigate subjective, emotionally-charged decisions. Deciding whether to sell your home carries financial implications, but it’s equally a lifestyle choice that benefits from human judgment.
“Investors should be comfortable using AI when it’s supported by human oversight, not when it operates in isolation,” Chou advises. The ideal framework includes AI recognizing its boundaries and recommending when a qualified human advisor should step in—particularly during major life transitions or complex financial situations. Better still: AI can transfer your complete financial context to the advisor, transforming a typical 30-minute advisory session into a highly customized, efficient consultation that benefits both parties.
The Bottom Line
Mark Cuban’s approach to AI—experimental, practical, and integrated—mirrors what savvy investors should adopt. AI isn’t a replacement for financial wisdom or professional guidance, but it’s an increasingly essential tool for anyone serious about building and protecting wealth. Whether you’re optimizing investments or managing health data, the principle remains the same: AI works best when it augments human capability rather than replacing it.