Think like Mark Cuban
This guy knows how to win where others fail
When you hear the name Mark Cuban, what comes to mind?
For me, it’s Shark Tank, a show that dominated culture for much of its run. It’s a Dallas Mavericks, the pro-basketball team that rose to become a force in the NBA during the 23 years that Mark owned them. It’s a certain swagger that comes with being a billionaire.
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But when I sat down with him recently, what struck me most wasn’t the bravado. Mark brings a settled clarity to conversation. Its this sticky combination of confidence, history and character.
I’m trying something new this week. I’m going throw out a few of the quotes that made this episode sticky. Let me know if you like this….
On risk: “If I knew my stuff, if I was prepared, it wasn’t a risk. The risk comes from lack of knowledge, lack of preparation.”
On decision-making: “It’s just dealing with probability. What’s the upside versus the downside? And if I can’t deal with the downside, you don’t do it.”
On trust: “Trust equals your transparency divided by your self-interest.”
On confidence: “If they haven’t outworked you, if they haven’t out-prepared you, then you have every reason to be confident.”
If I could, I’d attempt to encapsulate this mindset and apply it to my own work. This week’s episode is my attempt to do so. You can find it right here:
🤓 Worth it…
Why Millions Pay for AI Companions and the Hidden Mental Health Costs by Eva Crouse (Worth)
“Over 650 million people have developed an attachment to Xiaoice, one of the first AI companions, launched by Microsoft Asia in 2014. That’s more than twice Spotify’s subscriber base—and just one of hundreds of companion apps now available on the global market.”
Let’s start calling our working conditions what they actually are: indentured servitude. by Meg Sheding (Strategic Pivotry) “We are trapped in working conditions where we aren’t just overworked - we’re economically and psychologically trapped in a system designed to extract maximum value while offering minimal real security.”
🤓 Double Worth it…
A new AI startup called Friend (you can guess what it is by the name and you’re not wrong) has reportedly dropped more than a $1 million on an ad that is plastered across NYC’s subways. It’s so awful-effective that people brought it up at a dinner party I attended this past weekend.
The 21 year-old founder, Avi Schiffmann, told AdWeek: “I know people in New York hate AI, and things like AI companionship and wearables, probably more than anywhere else in the country.” I wonder if we New Yorkers really hate AI, or if we hate badly designed technology attempting to replicate and replace human relationships rather than augmenting them?
What’s this newsletter about again?
I’ve spent 20+ years covering tech from the inside for BusinessWeek, Fortune, and Wired. My mission is to close the gap between the people building the future—and those of us living it.





Love the encapsulating quotes! 🫶