Cuban and Calipari: Transparency, Listening, and Tangible Action

Key Quotes

"I was hustling as long as I can remember. I sold garbage bags door to door. I went my dad and his buddies were playing poker one day and I went in there to pick up a donut or something and, you know, and I'd known all his friends. I was like, 'Dad, I need some new basketball shoes.' He looks at my feet, he goes, 'Those shoes look like they work really well. When you have a job, you can buy whatever shoes you want.' I'm like, 'Dad, I'm 12, I'm not gonna get a job.' And one of his buddies, who had to be drunk, you know, spoke up and said, 'Hey, I've got a job for you. I've got all these boxes of garbage bags and you can sell them in the neighborhood.'"

Mark Cuban explains that his entrepreneurial drive began at a very young age, evidenced by his early ventures selling garbage bags door-to-door. This experience taught him the fundamental principle of finding value for customers, which he believes is crucial for any business success. Cuban highlights how this early exposure to sales and customer interaction built his confidence.

"For me, my goal always was to retire by the age of 35. You know, my dad did a post office run, cars, my mom did odd jobs, and they just had to grind it out. Gone at 7 AM, back at 6 PM. Eat dinner, watch some TV, go to sleep every single day. And my dad would take me where he worked and, you know, he'd have me sweeping and shoveling and doing whatever, not because he wanted to prepare me for that job, but because he wanted me to see that this was not a job that he wanted me to have."

Mark Cuban articulates his early motivation to achieve financial independence and control his own time, stemming from observing his parents' demanding work lives. Cuban's desire to retire by 35 was a direct response to his parents' daily grind. This ambition fueled his approach to building and selling companies rather than running a single one for life.

"You know, Steve Jobs said it best and it's always stuck with me that technology is a remix, or he said everything is a remix. And basically, what he meant was if you can create a base of understanding of the of technology and just continuously be learning, you'll see ideas that pop up that maybe be disruptive, but really are just an extension of taking new technologies and adding them to what's already in place."

Mark Cuban references Steve Jobs' concept of "everything is a remix" to explain his approach to technological innovation. Cuban believes that understanding foundational technology and committing to continuous learning allows one to identify disruptive ideas. These ideas, he explains, are often extensions of existing technologies combined in new ways.

"Along those same lines, Dr. Alex Oshmyansky and I created a company called Cost Plus Drugs, and what makes us different is that when you go to our website, costplusdrugs.com, and you put in the name of the medication that you want, we'll bring up information about it, but we'll also show you our actual cost. If it costs us $2, we'll show you it costs us $2. If it costs us $20, whatever it may be. Then we'll show you our actual markup, and those two things really make us different. We only mark up the price of the medications, um, only 15%."

Mark Cuban describes the core innovation of his company, Cost Plus Drugs, which is radical transparency in pharmaceutical pricing. Cuban explains that the company displays both the actual cost of medications and their own markup, which is a fixed 15%. This approach, he argues, is designed to build trust with consumers by clearly showing the pricing structure.

"The pharmacy business should be really, really easy. You go to the doctor, and if you needed some some help, the doctor prescribes a medication, and the only question is how much does it cost and how do you pay for it? In reality, though, what's happened is it's such a big industry, all these middlemen have stepped into to the industry and kind of created hundreds of arbitrations to squeeze money from patients. They're called pharmacy benefit managers."

Mark Cuban criticizes the current pharmaceutical industry's complexity, stating that the process of obtaining medication should be straightforward. Cuban identifies Pharmacy Benefit Managers (PBMs) as "middlemen" who introduce complexity and extract money from patients. He argues that these PBMs, rather than manufacturers, dictate drug prices and negotiate rebates.

"We were a pay it forward family. Never had everything, but never went without. Everyone in our community was the same. The families, blue collar workers in some form or fashion. My dad was in the mill for a while, and then he ended up going to, being a baggage handler for, at the time, Allegheny Airlines. Mom worked in the high school cafeteria, she sold ice cream."

Coach John Calipari reflects on his upbringing in a blue-collar family in Pittsburgh, emphasizing a culture of mutual support and hard work. Calipari describes his parents' jobs and the community's shared values, where "pay it forward" was a guiding principle. This background, he suggests, instilled in him the importance of effort and not expecting shortcuts.

"My first year at UMass, we gave up 100 points, I think 14 times. We were the worst defensive team in the league. By my first year, I called Rick Barnes, who's a good friend, and I said, 'Rick, what do I do?' He asked, 'What, um, what would you say?' 'I don't know if we'll jump dots, what would you tell me?' 'You demand, what do you work on? What are your defensive principles?' So I tried to give him like 20 things, too many, too many. 'Give me four.' And from that point, ball pressure, gaps, don't give them lanes, get around the post, and get off on the weak side. And to this day, that's basically the premise of our defense."

Coach John Calipari recounts a pivotal moment early in his coaching career at UMass where he sought advice from Rick Barnes after a defensively poor season. Calipari explains that Barnes' advice to focus on four core defensive principles--ball pressure, gaps, no lanes, and weak-side help--became the foundation of his defensive strategy. This experience taught Calipari the value of simplification and focused execution in coaching.

"Leadership in these jobs is how do I help? How do I move? How do I influence? What do I do that this state or city or university needs from me? The students, Ellen and I did something for the students in education, knowing the loans that those kids have, which was incredible. We talked to the school, the dean of the school of education, to say, 'How can we help?'"