Billionaire entrepreneur Mark Cuban has a clear piece of guidance for his two children currently navigating the job market: choose small companies over giant corporations.
And according to him, this recommendation doesn’t just benefit his kids—it’s a powerful strategy for any Gen Z job seeker entering today’s AI-driven work environment.
Cuban’s rationale is straightforward: your skills—and especially your AI skills—matter far more in smaller organizations.
In huge corporations, even if you’re a fresh graduate proficient in the latest AI tools, your expertise can feel “somewhat extraneous,” he told CNBC Make It. Large firms already possess well-established IT departments with experienced engineers who know these tools as well as—if not better than—new employees.
Smaller organizations, however, function very differently.
They “don’t have that depth,” Cuban explained.
“[Small-to-medium-sized companies] are typically entrepreneurially driven and don’t have the flexibility to have people research things,” he added. “Bringing a new graduate on to work on agentic AI projects is inexpensive for them and can get them immediate results.”
This insight from Cuban—whose net worth stands at roughly $6 billion—comes at a moment when Gen Z job applicants are facing unprecedented challenges. AI has automated many traditional entry-level responsibilities, such as data entry, summarization, and routine administrative work. But Cuban argues that these same shifts create new opportunities within smaller enterprises, where AI expertise is rapidly becoming a competitive weapon rather than a replaceable skill.
What Makes Gen Z Candidates Stand Out Today
Among small businesses that are embracing AI, Gen Z is leading the adoption curve.
A survey by CNBC | SurveyMonkey reveals:
- 37% of small business owners currently use AI tools
- 71% plan to increase their AI investment
Cuban told Fortune that the differentiating factor for young applicants at small companies is their capacity to create simple, functional AI agents that automate the tedious tasks no one has time to complete because “manual labor is too expensive.”
“Every company has stuff that doesn’t get done because it would require someone to sit with a spreadsheet for hours. Or to count things. Or to edit. Or to check receipts for accuracy.” Cuban said. “These things can be done with agents and save small companies cash and improve productivity and competitiveness.”
According to him, it only takes “a basic understanding of programming and how AI models create agents” to start making an immediate impact.
Cuban Gives the Same Advice to His Own Kids
The Shark Tank star is raising three children, two of whom are currently studying at Vanderbilt University and UCLA. He consistently encourages them not only to study AI but to understand how these skills can be applied inside real companies.
As he previously said on The Dumbest Guy in the Room podcast:
“Like I tell every young kid, there’s going to be two types of companies in this country: There’s going to be those who are great at AI and those who used to be in business.”
AI Is Boosting Productivity at Big Companies—While Small Firms Struggle
Cuban’s advice also reflects the growing AI divide between large corporations and smaller firms.
Since OpenAI released the first version of ChatGPT in 2022, major enterprises have experienced massive productivity boosts, allowing them to optimize workflows and in many cases reduce headcount. Meanwhile, small-cap companies are witnessing the opposite: a drop in real revenue per employee.
A recent comparison of major indices illustrates the widening gap:
- The S&P 500 has risen 74% since ChatGPT’s launch
- The Russell 2000—representing small-cap businesses—has climbed only 39%
In addition, a World Economic Forum survey from early 2025 found that 40% of companies expect to reduce jobs in areas where AI can take over routine task automation.
For Cuban, this imbalance only emphasizes why Gen Z individuals with AI abilities can become invaluable assets at smaller organizations struggling to keep up.
Stumora Insight: Why This Matters for Today’s Young Professionals
This message from Cuban isn’t just career advice—it’s a blueprint for thriving in a future where AI will decide winners and losers in the job market.
- Small companies give you real responsibilities faster
- Your AI knowledge creates instant value
- You build practical, hands-on experience—not just theoretical learning
- You become part of the growth engine instead of a tiny piece of a giant corporate machine
In the evolving landscape of technology, automation, and competitive business ecosystems, Cuban’s direction highlights one central truth: Gen Z workers who understand AI—and know how to apply it—will shape the next generation of impactful businesses.