Mark Cuban: The Next Market Crash Is Where The Real Money Is Made!

Mark, you keep putting yourself back in school when a new wave arrives—crypto, AI, whatever it is. You treat business like a competitive sport: stop improving, and somebody younger, faster, and hungrier runs past you.

That’s exactly it. In tech or media, some kid somewhere can kick your ass. I’d rather be the one kicking ass. I grew up regular, blue-collar, but I had that piss and vinegar to compete and turn an idea into something real.

My dad did upholstery on cars, lost an eye in an accident, and kept grinding. He could make friends anywhere. He told me I wasn’t stuck in the world I arrived in, that today is as young as I’ll ever be, and he backed every little hustle.

I wanted to play baseball until I realized I wasn’t good enough. At nine or ten, I repacked baseball cards with a guaranteed Pirates player and sold them at a markup. At twelve, after I wanted basketball shoes, Dad told me to get a job, so I sold garbage bags door to door. If you can knock on doors and hear no, you can handle a lot.

Sales isn’t tricking somebody into a bad decision. It’s knowing your product, figuring out what they need, and showing how it helps. Rejection gets you nearer to yes, and objections teach you to think on your feet. Once you can sell, you can always earn a living.

Don’t start with, ‘I want to be an entrepreneur, what idea should I pick?’ That’s ridiculous. Get genuinely good at something—selling, coding, drawing, tinkering—and see whether it can become a business. When I started MicroSolutions, I was broke, fired, living with five other guys, sleeping wherever I could. Surviving one month, then three, then six was progress. We stayed profitable; sales without profit aren’t the whole damn point.

I bought the Mavericks because I loved basketball and thought it would be fun. I wanted to turn a terrible franchise into a winner. Winning the championship was incredible, but weirdly anticlimactic—I’d watched too many games flip at the end to relax. What got me was taking the trophy around the city and seeing people light up. That shared joy was bigger than my own celebration.

If you feel stuck, don’t wait for the ideal job. Get a job and become excellent at it. Know where you suck, ask people around you, and build a record that makes a manager sorry to lose you. When I was fired from a software store, I decided I wasn’t built to be somebody’s employee. I took computers home or stayed overnight reading manuals until I had an edge.

AI is bigger than every previous technology wave combined for productivity and access to knowledge. With a phone or library computer, you can ask almost anything. But you still have to read the response, improve your questions, and apply it. I use agents constantly: at Cost Plus Drugs, they flag lawsuits and bids involving healthcare conglomerates and help draft open-records requests. Tedious work I never had time to hire and manage for now gets done.

But AI isn’t smart. It predicts outputs from patterns, gives varying answers, lacks built-in ethics, and doesn’t grasp real-world consequences. Smart means identifying the problem, finding inputs, and combining them to solve it. AI can spit out a business plan, but I still have to decide what’s bullshit, what works, and how to sell it.

I worry more about people misunderstanding AI than AI taking over. Social algorithms feed kids get-rich-quick garbage while nobody sees the boring preparation behind a win. If somebody is selling you a great stock-market edge or easy dropshipping scheme, ask why they aren’t just doing it themselves. Do the work before expecting the reward.

Markets are bubbly, though not like the old dot-com crash. Prices swing on tiny news, and I don’t know who the AI winners will be. I’d keep some cash, be patient, and understand great companies can get crushed before recovering. The bigger concern is debt powering data centers. AI needs to do more with less energy, not just pile on GPUs and power.

I was the fat kid who wanted attention and wanted to prove people wrong. Success was less about fame than escaping being broke and controlling my time. Money removes stresses, but it doesn’t repair who you are. I used to yell at MicroSolutions until Todd Wagner told me people were scared of me. He was right. I got farther—and felt better—when I stopped being a dick.

I’m fast-moving and awful with details, so I need partners who complement me. Culture matters too. With the Mavs, we built to win: development help, better travel, nutrition, and tools. Talent without team culture won’t get it done. My family is the better part of me. I regret missing little things with my kids, which is why I sold the Mavs and left Shark Tank. Birthdays and time with them mattered more. My favorite word is still ‘Dad.’

Not everyone should become an entrepreneur. You don’t get more control; customers, employees, and problems own your time. You need something you’re driven to accomplish and the willingness to prepare and fight through the mess. These days, I’m putting that energy into Cost Plus Drugs: cutting healthcare costs and breaking the grip of the biggest players.

You’ve made the case that preparation, skill, family, and being decent matter more than the flashy version of success. I came in admiring the business story, but I’m leaving struck that you can be hugely successful and still show up optimistic, purposeful, and human. Mark, thank you.

Thank you, Steven. I really enjoyed it.