Andy Beshear Podcast – BONUS: Mark Cuban and Coach Cal (Dec 25, 2025)

Episode Overview

In this special holiday bonus episode, Andy Beshear revisits two standout interviews: business titan and NBA owner Mark Cuban, and legendary basketball coach John Calipari (now of the Arkansas Razorbacks). The episode explores themes of entrepreneurship, transparency in healthcare, the impact of politics on daily life, leadership, resilience, and serving the community—offering unscripted, candid insights into the real lives and values behind fame and accomplishment.

Mark Cuban Interview

Timestamps: [02:01] – [30:18]

Mark Cuban’s Entrepreneurial Beginnings

• Cuban shares stories which reveal his drive from a young age:
  • At age 9-10, he was hustling with baseball cards and later sold garbage bags door-to-door.
  • Learned selling was about discovering and delivering value:
    • “If you can be a kid selling door to door, you can sell anything.” (03:48)
  • Mentored by his hardworking parents—dad was an auto upholsterer, mom did odd jobs—which instilled in him a desire to control his own destiny.

Shark Tank and the American Dream

• Sees himself in many of the Shark Tank entrepreneurs:
  • “Every entrepreneur goes through a phase where it’s ‘I don’t know if I’m going to make it. I don’t know if I made the right choice.’ …So I can always relate to them.” (04:22)
• Cuban’s approach differs from typical billionaires:
  • Serial founder and seller, rather than clinging to one business for life.
  • Motivated by freedom and impact rather than longevity:
    • “I never looked at them [companies] and thought, ‘this is the company I’m going to run for life.’ …If I can sell it, I’m going to sell it.” (06:21)

Innovating for the Future: Technology and AI

• Credits relentless learning as the root of his success:
  • Believes in “everything is a remix” (reference to Steve Jobs).
  • Positions himself at the intersection of new technologies and existing needs.
• AI as the most disruptive technology:
  • “AI is going to change how we live our lives. …There’s not a whole lot of things that AI won’t touch.” (08:43)
• Philanthropy focuses on democratizing access to the future:
  • Mark Cuban Foundation’s AI Bootcamps teach underprivileged high schoolers about AI.
    • “If we can get some kids excited about it now, when they’re 16, 17, 18, they’re going to be the ones that teach us how to use it when they’re 28, 29, 30.” (10:35)
  • Global Teaching Project brings AP-level courses to schools that previously lacked them.

Disrupting Healthcare: Cost Plus Drugs

• Cuban explains the genesis and mission of Cost Plus Drugs, created to bring transparency to prescription drug pricing.
  • The model: publish the actual cost of drugs + a flat 15% markup.
    • “I’m a big believer that the missing component in healthcare …is trust. To engender trust… trust equals transparency divided by self-interest.” (12:18)
    • The company has already served millions since its 2022 launch.
  • Critiques the existing system:
    • “The pharmacy business should be really, really easy. …In reality…it’s such a big industry, all these middlemen have stepped into the industry and kind of created hundreds of arbitrages to squeeze money from patients.” (13:44)
    • Pharmacy Benefit Managers (PBMs) are the true price-setters—often to the detriment of patients and transparency.

Politics, Leadership, and Small Towns

• Cuban decries the Democratic Party’s reliance on consultants and over-tested messaging:
  • “[Politicians] never let Kamala Harris just be Kamala Harris… they always over tested everything. …I’m just not a big believer in that.” (16:12)
  • Advocates for direct connection with “the customer” (i.e., voters)—listening to small-town experiences.
• Warns of the impact of tariffs, federal budget cuts (“Doge cuts”), and the closure of rural institutions.
  • “All these things that seem like little things, they’re adding up.” (20:09)
• On Republican vs. Democratic messaging:
  • “Democrats look at something and they extrapolate out and say, this is the way it’s going to be…Republicans say this is the way it is and this is the pain you’re feeling. …I think the Democrats need to get a better handle on doing that.” (18:25)

Understanding Trump Supporters

• Cuban acknowledges and seeks to understand the enduring support for Trump, pointing out that on core issues (“the border,” deportations, anti-DEI policies), Trump has met supporter expectations—even where methods are harmful.
  • “Shouldn’t I give him the benefit of the doubt on tariffs and inflation? And you can understand why they believe that’s the case.” (24:33)

The Plight of Small Businesses

• Cuban is deeply critical of the lack of attention to small business:
  • “There are 33 million companies in this country. 30 million of them are small business or solo entrepreneurs… They are not in a position to absorb tariffs like [Trump] may believe.” (28:47)
  • Calls for creation of Small Business Councils to give true voice to entrepreneurs’ struggles.

Notable Quotes:

• “If you can be a kid selling door to door, you can sell anything.” – Mark Cuban [03:48]
• “I just love learning it. …Now with AI, this is easily the most disruptive technology we’ve ever seen. And it’s not even close.” [08:38]
• “Trust equals transparency divided by self interest.” [12:18]
• “The pharmacy business should be really, really easy… all these middlemen have stepped into to the industry and kind of created hundreds of arbitrages to squeeze money from patients.” [13:44]
• “The American dream is built by small business entrepreneurs.” [28:57]

John Calipari ("Coach Cal") Interview

Timestamps: [30:18] – [50:27]

Blue-Collar Roots and Early Lessons

• Raised in a working-class “pay it forward” family in Pittsburgh; both parents worked service jobs.
  • “We never had everything, but never went without. …What you learn: You don’t work, you don’t eat. You better work.” (31:42)
  • Community emphasized hard work, sharing, and taking care of neighbors.
• Recalls a world where everyone’s door was open and “wherever you were, you ate.”

Origins of a Coaching Career

• Inspired by local teachers and Italian-American coaches he looked up to as a child.
  • “I started at a young age knowing what I wanted to do…we were gym rats, and it wasn’t just me, it was our whole team.” (33:51)
• Tells of his first break: driving to Kansas to work camp; got invited as a volunteer assistant coach.
  • Lived frugally, worked camp kitchens, and never got into coaching for money—“It’s about loving the profession, loving the players, loving to see them grow.” (36:46)
  • Met his wife at the university—a humorous, self-deprecating story about who pursued whom.

Failures, Learning, and Leadership

• Reflects on struggles early at UMass (“gave up 100 points 14 times…worst defensive team in the country”) and seeking advice to simplify defense and focus on fundamentals.
  • “If you don’t fail, if you don’t take a spill or two… it’s hard to not worry about result, worry about your team getting better, worry about the process…” (41:10)
• Champions the “winning and learning” mentality—emphasizes process, not just results.
  • “I want to see when things go bad, what kind of leader is that coach? …Do you blame or do you take responsibility?” (41:41)
• Parallels made to Beshear’s own leadership through disasters:
  • “Well, what do we do? Jump under the covers? Do we blame? Or do we just go out, let’s get something done?” (42:16)
• Both recall aiding disaster victims quietly (“gave cash out, probably weren’t supposed to. Can I get arrested for that?” – 44:56)

Leading with Compassion and Community Involvement

• Calipari strives to be more than “just the basketball coach”—wants to drive service, empathy, and resilience.
  • “It carries weight in those states. You’ve done things that no one knows… And you’re a politician… you’re not really a politician, Governor.” (43:59)
• Highlights the impact of leading by example for young athletes:
  • “The best sermon is one without words.” (47:13)
• Tells how his team’s charitable acts arose from the players’ own initiative, not his.

On Trust and Player Development

• Trust is foundational: “You under-promise and over-deliver. …The biggest compliment is when former players send their sons for me. That’s the ultimate: I trust him.” (49:22)
• “If you embellish, if you say whatever you have to get them to come and you can’t follow through, how do you have trust?”

Notable Quotes:

• “We never had everything, but never went without. …You don’t work, you don’t eat.” – John Calipari [31:42]
• “If you don’t fail… it’s hard to not worry about result, worry about your team getting better, worry about the process…” [41:10]
• "[After disasters] …we gave cash out, probably weren’t supposed to. Can I get arrested for that? …I think I can pardon you." – John Calipari & Andy Beshear [44:56]
• “The best sermon is one without words.” [47:13]
• “You under-promise and over-deliver…the biggest compliment… is when former players send their sons for me. That’s the ultimate: I trust him.” [49:22]

Memorable Moments & Highlights

• Mark Cuban’s playfulness: “If I got offered [teaching sorority line dancing] today, I’d quit everything else and take that job.” [05:25]
• Coach Cal’s community ethos: Growing up, his mother would re-wrap his Christmas presents to give to guests in need.
• Leadership Under Pressure: Both Cuban and Calipari offer concrete stories of resilience, taking responsibility, and being present with those most affected by hard times—not just talking, but acting.
• Off-the-cuff jokes: Calipari jokingly requests a pardon for giving out cash to disaster victims; Beshear (“I think I can pardon you”) provides the punchline.
• Coaching moments: Calipari reflects on learning from adversity, coaching for the love of the craft, and maintaining humility even at the top of his game.

Key Segment Index

| Segment | Timestamp | |----------------------------------------|--------------------| | Andy Beshear intro & overview | [00:38] – [02:01] | | Mark Cuban interview | [02:01] – [30:18] | | John Calipari interview | [30:18] – [50:27] | | Highlight: Collaboration/Philanthropy | [44:00] – [47:40] | | Trust, player development (Calipari) | [49:22] | | Inspiring leadership stories (All) | Throughout |

Episode Tone and Style

• Welcoming, candid, and unscripted. Andy Beshear steers conversations with empathy, wit, and curiosity.
• Both guests display humility and humor, grounded in their life experiences and commitment to service.
• The episode balances inspiration and realism, offering both behind-the-scenes stories and hard truths about leadership, business, and politics.

For listeners:
This episode packs practical wisdom, candid behind-the-scenes stories, and a reminder that leadership—whether in sports, business, or politics—is ultimately about serving people, building trust, and not being afraid to get your hands dirty.