By Jordan Kensington | Brand Weekly | Featured on The Business TV Show
In an expansive and thought-provoking conversation, Jordan Kensington sits down with billionaire entrepreneur and investor Mark Cuban — a figure who has continuously reshaped the boundaries of sports, healthcare, media, and technology. From founding tech companies to owning the Dallas Mavericks, Cuban’s insights go far beyond headlines. In this exclusive for Brand Weekly and The Business TV Show, Cuban reveals what drives his decisions, where he’s placing his biggest bets, and what entrepreneurs need to prepare for in the next decade.
Jordan Kensington:
Mark, people know the headlines — billionaire, Mavericks, Shark Tank. But let’s start with the lesser-known side. What gets you out of bed in 2025? What are you building now?
Mark Cuban:
I wake up every day thinking about how to reduce the friction people face in their daily lives. Right now, my biggest focus is Cost Plus Drugs. The healthcare industry is broken — intentionally opaque and fundamentally exploitative. We’re building something radically transparent. You go to Cost Plus Drugs, you see exactly what we paid for the drug, what we charge, and how much margin we take. That’s it. No middlemen, no hidden fees. If we can scale this, it changes the game for millions of people.
Jordan Kensington:
Let’s dive into that. You’re attacking Big Pharma’s pricing model directly. Why take on such an entrenched system?
Mark Cuban:
Because no one else would. The system thrives on complexity. And when you look at how many people have to choose between insulin and rent, something’s wrong. I wanted to create a business that’s capitalist in its mechanics but humanitarian in its outcome. We don’t take insurance — not because we’re anti-insurance, but because the insurance model adds cost and opacity. We’re bringing ecommerce-style simplicity to an industry that’s thrived on confusion.
Jordan Kensington:
You’ve also been vocal about AI, automation, and decentralised platforms. How do you see those intersecting with entrepreneurship in the next five years?
Mark Cuban:
AI is the electricity of the next 50 years — everything will plug into it. But here’s the thing: most people think AI will replace jobs. That’s the wrong question. AI will replace processes, and that will create opportunities to redefine jobs. The entrepreneurs who win will be the ones who understand how to use AI to free up human potential. As for decentralisation — blockchain, Web3 — we’re still in the infrastructure phase. But when it matures, it’s going to erode trust-based intermediaries in ways we’ve never seen.
Jordan Kensington:
Are you investing in that space directly?
Mark Cuban:
Absolutely. I’ve invested in multiple Web3 startups — some of them didn’t work out, but that’s part of the game. I’m particularly interested in smart contracts applied to real-world assets: real estate, event ticketing, even healthcare records. Once we can confidently verify identity and value without a third party, you’re going to see entire industries flatten out. That excites me.
Jordan Kensington:
On Shark Tank, you’ve backed scrappy founders, but you’re also building at scale. What makes a business, in your eyes, “worth the bet”?
Mark Cuban:
One word: obsession. I don’t invest in people who just “like” their idea. I invest in people who are obsessed — who know their customer better than the customer knows themselves. I can tell in five minutes if a founder has that fire. I’m also big on digital leverage — does this business scale with code? Can it scale without needing 10,000 new employees? If yes, I’m listening.
Jordan Kensington:
Let’s shift gears. You sold Broadcast.com in the dotcom era. You’ve seen Web1, Web2, and now Web3. What has really changed?
Mark Cuban:
Distribution is now free. That’s the biggest shift. When I was running Broadcast.com, we had to fight just to stream one event. Now, anyone with a phone and an idea has global reach. That’s incredibly powerful. But it also means the noise is louder than ever. The winners are the ones who create signal in the noise — through great product, smart branding, or by building trust faster than the competition.
Jordan Kensington:
How do you personally stay sharp? You’ve made it — why keep learning?
Mark Cuban:
Because the second you stop learning, you’re dead in this game. I read at least 3 hours a day — everything from AI research papers to business newsletters. I’m in the trenches because that’s where the action is. Success is a moving target, and if you’re not adapting, you’re regressing.
Jordan Kensington:
Last question — legacy. What do you want to be remembered for?
Mark Cuban:
That I helped more people than I took from. That I built things that made life a little better, a little fairer. Whether it’s sports, drugs, media, or tech — if I changed the game and inspired a few people to think bigger, I’m good with that.
Jordan Kensington:
Mark, thank you. Not just for your time — but for sharing truth that cuts deeper than the usual soundbites.
Mark Cuban:
Appreciate it, Jordan. Keep pushing the culture forward.
This interview is part of The Business TV Show series, syndicated by VooVix TV and published by Brand Weekly.
For more, visit www.voovixtv.com or www.nita.community
