I first met Mark Cuban on a red carpet for a movie premiere I was covering as a young entertainment host. At the time, Mark was already a recognizable figure — not just for selling Broadcast.com to Yahoo during the dot-com boom, but as one of the faces of that entire era of internet-fueled wealth. He even made a cameo on “The Simpsons.”
Fast forward to 2011: I had just launched “What’s Trending,” one of the first live digital shows covering internet culture, and CBS News picked it up. We hosted guests like Snoop Dogg, Common, Lilly Singh, and Bill Nye the Science Guy. Naturally, I had to ask Mark to join us, too — by then, he was gaining even more mainstream fame through “Shark Tank” and I was starting to see him as a potential mentor.
In all the years I’ve known Mark, he’s never given me a dollar — and yet his support, guidance, and friendship have been worth so much more.
Mark Cuban gave me a reality check that helped me keep my business going
He liked what my team and I were building with “What’s Trending,” and appreciated the entrepreneurial spirit behind it. But it was a few months later, during a major career crisis, that Mark truly stepped into the role of mentor.
In a single weekend, CBS News suddenly dropped the show. My cofounder and I were devastated, and I reached out to Mark. Was there anything he could do to help?
By chance, he was flying into Los Angeles to film “Shark Tank” and told us to meet him at the SLS Hotel. I showed up in all black, puffy-eyed from crying. I was hoping for a lifeline. Instead, Mark gave me tough love.
I had to negotiate with a Shark
He offered us a deal: He would air “What’s Trending” on HDNet, the TV network he owned at the time. But there was a catch: no money upfront, exclusive rights to him, and a revenue share model on advertising.
In an instant, I had to snap out of my grief and start negotiating with a real Shark.
I didn’t think it was a good deal and felt he shouldn’t get exclusive rights if he wasn’t giving us upfront cash. Looking back, I realize I probably should’ve taken it — we would’ve figured the rest out along the way.
I sat there, unsure, my brain spinning, and that’s when Mark looked me square in the eye and asked: “Are you passionate about what you’re doing?” I said yes, without hesitation, and he convinced me that if I truly cared, I could find the $50,000 to keep my show going.
That conversation forced me to see myself as a startup founder
I realized that if I was going to ask someone else to invest in me, I needed to be willing to invest in my own vision first.
Since then, Mark has offered many more moments of tough love — each one a precursor to some of my biggest career breakthroughs. When I got in early on Musical.ly before it became TikTok, I poured a lot of time and energy into it and had a real vision, but I was ahead of the curve. The money wasn’t there yet.
Mark pushed me to know my worth and ask to be paid because I deserved it. That mindset shift led me to consulting work and has helped me negotiate with a lot more clarity as a creator.
I’ve learned some of my best business lessons from Mark
1. Always be selling.
No matter what you’re doing — building a company, launching a project, pitching an idea — you’re always selling yourself, your vision, and your value.
That doesn’t mean everything has to be transactional, but be aware and open to opportunities because they’re literally everywhere.
2. There are two kinds of companies: those that are great at AI and everyone else.
When it comes to emerging tech, it’s all about following where the money and attention are going and identifying clear gaps in the space.
Right now, and likely for the future, that’s AI. During a recent recording of my podcast, “The AI Download,” Mark was a guest and reminded me how important it is to create content in this space now — to connect with the right players, to learn by doing, and to test the tools firsthand.
This approach has helped me grow as a thought leader, led to brand deals, and even opened up an opportunity to lead growth and marketing for INSEAD AI Venture Lab, an 8-week global AI training program.
3. Sweat equity is the best equity.
I’ve mostly bootstrapped my company, growing it through relationships, creativity, and reinvention rather than outside funding.
Building with sweat equity forced me to get scrappy, stay lean, and focus on what truly matters. It made me and the company more resilient, and along the way, it revealed who was genuinely committed.
4. Run your business to be profitable.
Profitable companies don’t go out of business. It sounds simple, but in the world of flashy startup rounds and burn rates, it’s a powerful reminder.
My own business has definitely had its ups and downs with this.
Running a business without focusing on profitability isn’t sustainable. It drains your energy, gives you headaches, and takes time and resources away from ideas that could actually grow. It becomes less of a business and more of an expensive hobby.
Not focusing on profitability also forces you to constantly raise money and put your vision in the hands of investors, which can mean giving up control.
5. Kindness is a secret weapon.
Mark is literally the nicest billionaire I know — not that I have a huge roster of billionaires on speed dial.
He may not respond to every single email, but he’s known for being surprisingly responsive, even to cold emails from strangers. I’ve always been struck by how quickly he replies. It’s not always a yes; sometimes it’s a quick “not interested.” But the fact that he takes the time to respond at all says a lot.
If someone like him can be that timely and direct without relying on layers of gatekeepers, it challenges me to do the same. It reminds me that respect and efficiency go hand in hand, no matter how busy you are.
Shira Lazar is an Emmy-nominated host, producer, and entrepreneur. She’s the founder/CEO of the media brand “What’s Trending” and cofounder of CreatorCare, a mental health support system for creators.
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