I Used Mark Cuban’s Side-Hustle Strategies and Now Make $2,800 Extra Every Month
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Laura Beck
Edited by
Levi Leidy
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Tim B. was six months into unemployment when he started binge-watching old “Shark Tank” episodes at 2 a.m. The 35-year-old Los Angeles writer had burned through his savings and needed income yesterday.
“I’d heard all the generic advice about hustling,” Tim said. “But Cuban actually breaks things down into steps you can follow. I figured I had nothing to lose. Besides, he’s my favorite Shark! How bad could this go!?”
Three months later, Tim’s bringing in $2,800 monthly from side work. Here’s how he applied Cuban’s specific strategies.
Strategy 1: Teaching AI to Businesses
Cuban gave his No. 1 recommendation in a 2024 CNBC interview. If he were starting over as a teenager, he’d learn artificial intelligence (AI) prompt writing, teach friends, then take that skill to companies.
“Then, I would go to businesses, particularly small- to medium-sized businesses that don’t understand AI yet,” Cuban said. “Doesn’t matter if I’m 16, I’d be teaching them as well.”
Tim spent two weeks teaching himself prompt engineering through free tutorials. He practiced until ChatGPT consistently delivered what he needed.
“My friend owns a landscaping company,” Tim said. “He’d heard of ChatGPT but had no idea how to actually use it for customer emails or social posts. I charged him $200 to build templates and walk him through it.”
That first client led to five more within a month. Each paid between $150 and $400 for consultation and setup. Monthly income from AI teaching: $1,400.
Strategy 2: Spotting Value Others Miss
As a teenager, Cuban made money finding price differences in collectibles. The concept was simple: Spot something undervalued, recognize its real worth and sell it for what it’s actually worth.
Tim applied this to his creative background. He started scanning Facebook Marketplace for furniture and home goods with awful photos and weak descriptions.
“I’d message sellers offering to reshoot their listings with better photos and rewrite the copy for $50,” Tim said. “Most items sold within days after that instead of sitting for weeks.”
This service pulls in $800 monthly from roughly four clients per week. Each listing takes under an hour.
“It’s not about the furniture,” Tim said. “It’s about seeing that gap between what something is and how it’s being presented. I think Cuban would be proud! Or at least I hope he’d be.”
Strategy 3: Services People Actually Need
Cuban’s advice for beginners focuses on offering services to people you already know. Not complicated products or tech platforms — just skills applied to solve immediate problems.
Tim realized his writing and editing abilities had market value outside traditional jobs. He reached out to his network offering to edit college essays, business proposals and resumes.
“I charged $75 per hour,” Tim said. “A strong edit can mean getting into a program or landing a contract. That’s worth way more than my hourly rate to them. Plus, as someone who has been out of ‘real’ work for a long time, it just made me feel useful, which I think is important!”
This third income stream adds $600 monthly for about eight hours of work total.
The Mindset That Actually Mattered
Cuban’s advice goes beyond tactics. When asked what separates successful side hustlers from failures, he answered: “They don’t give up.”
Tim almost quit after his first three pitches got rejected.
“Trust me, I wanted to stop immediately,” he admitted. “But if Cuban could handle selling garbage bags door-to-door as a kid, I could survive a few nos. I kept telling myself: Toughen up!”
Cuban also emphasized proof through payment. “When customers start sending you money, you know your side hustle has real market potential,” he said.
That first $200 payment changed Tim’s entire approach.
“Once money hit my account, I stopped doubting,” Tim said. “The concept worked. I just needed to scale it.”
Results From 3 Side Hustles
Tim’s three hustles now generate $2,800 monthly:
- AI business consulting: $1,400
- Marketplace listing improvements: $800
- Writing and editing: $600
None required upfront cash beyond his time. He works roughly 25 hours weekly across all three, leaving space for job hunting and personal projects.
“I thought side hustles meant destroying yourself with 80-hour weeks,” Tim said. “But no, not really. The point is work smarter, not harder. Well, do both.”
What Changed Beyond Money
The income matters, but Tim said Cuban’s framework rewired how he views opportunity.
“I stopped waiting for someone to hand me a job,” he said. “Now I look at every small business owner and think about what they’re struggling with and whether I can solve it. Every conversation becomes potential work.”
That shift came from studying Cuban’s trajectory. The billionaire started with tiny hustles as a kid and never stopped looking for angles.
Six months ago, Tim was unemployed and panicking. Today he’s generating nearly $3,000 monthly while still pursuing full-time opportunities. The skills he built make him more valuable as a candidate too.
“Whether I land a traditional job or grow these hustles bigger, I’m never relying on one income source again,” Tim said. “Cuban taught me diversification isn’t just for investments, it’s for income.”
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