Renowned investor Mark Cuban, whose net worth is estimated at $6 billion, has outlined several side-hustle strategies he has used personally, along with new approaches he believes would be effective for young people growing up in the age of artificial intelligence. One of his followers, Tim B., put that advice into practice after hearing Cuban’s comments in an interview with GoBankingRates—and the results were substantial.
At age 35, Tim, a Los Angeles–based writer, had been unemployed for six months when he began watching old episodes of Shark Tank late at night. Cuban’s guidance stood out to him as far more actionable than the generic “work harder” advice he had encountered elsewhere.
This comes at a time when, according to an October Omnisend survey, about 31 percent of American adults earn income from a side hustle, collectively generating billions of dollars each month. The trend reflects ongoing economic headwinds, rising consumer prices, and a softer job market.
By following Cuban’s playbook, Tim now earns roughly $2,800 per month from 25 hours of side work—while still maintaining enough flexibility to pursue full-time opportunities and personal projects.
Provide AI Services to Businesses
Cuban told CNBC that if he were 16 today, he would master AI prompting and monetize it. He said he would begin by teaching classmates how to use AI tools for schoolwork, then expand to serving businesses—particularly small and midsize companies that have yet to adopt AI effectively.
Tim applied this strategy immediately. He reached out to a friend who owned a landscaping business and discovered the owner had heard of ChatGPT but didn’t know how to leverage it for customer communication or social media. Tim charged $200 to build templates and train him on basic use.
Within a month, he had added five more clients, earning a total of $1,400 from his AI-related services.
Identify Undervalued Assets and Resell
Another of Cuban’s recommendations is one he has practiced himself: finding undervalued items and reselling them at market-appropriate prices.
Tim scanned Facebook Marketplace for long-listed items and offered sellers a $50 service to rewrite their descriptions and upload better photos. Most refreshed listings sold within days.
“It’s not about the furniture,” Tim said. “It’s about spotting the gap between what something is and how it’s being presented.”
This strategy earns him about $800 each month from four clients, with each listing taking under an hour to complete.
Market the Skills You Already Have
Cuban also encourages people to use their existing strengths to solve others’ problems. For Tim, this meant offering writing and editing services—particularly for college essays, résumés, and business proposals.
He charges $75 per hour and earns approximately $600 each month from eight hours of work.
Tim’s experience not only validates Cuban’s advice but also aligns with Cuban’s broader view of what differentiates successful side hustlers.
“They don’t give up,” Tim said.