Mark Cuban was born a serial entrepreneur. At age 12, he sold trash bags door to door. By age 16, he had a business selling stamps. During college at Indiana University, he taught disco lessons at sorority houses and opened a popular bar before he turned 21. So how does an average kid growing up in Pittsburgh go on to become a self-made billionaire?

For some of us, it may be hard to imagine the person that we know today as Mark Cuban quit a job, was fired from another, had a business that closed down because somebody who worked there was on probation for prostitution, and slept on the floor of an apartment for many months after moving to Dallas. But it was these experiences that made Mark the businessman, investor, philanthropist, and billionaire that he is today. Mark’s journey is one of incredibly hard work, determination and perseverance, adapting to change, and learning from failure.

In this episode, Randall and Mark talk about challenges on Mark’s path to excellence, the role Mark played in the early days of the internet with MicroSolutions, the story behind AudioNet/ Broadcast.com, taking it public, selling it to Yahoo for $5.7 billion, and how he sold his stock in what is considered one of the most brilliant business decisions of all-time. Randall and Mark also discuss Mark’s latest company The Mark Cuban Cost-Plus Drug Company, and his very sage advice for young entrepreneurs.

Topics Include:
- How his college experience prepared him for success
- The lessons about sales Mark learned as a 12-year-old selling trash bags door to door
- Why you can learn just as much from the bad companies as the good ones
- The interview answer that got him a job with no experience
- Mark’s brief career as an actor and reading for Stephen Spielberg
- Why owning a sports team is unique from owning a business
- Mark’s powerful Shark Tank episode with Tania Speaks Organic Skincare
- The importance of preparation and learning from failure
- Mark’s thoughts on parenting
- How his work-life balance has changed over time
- Mark’s charitable work through the Mark Cuban Foundation and Fallen Patriots Fund
- And other topics…

Mark Cuban is a serial entrepreneur, investor, owner of the Dallas Mavericks, and a host of Shark Tank on NBC. Mark made his initial fortune through the sales of his startups MicroSolutions and Broadcast.com in the 1990s, and he was was ranked #177 on the 2020 Forbes 400 list of the wealthiest residents in the United States.

Mark is also the best-selling author of How to Win at the Sport of Business. Among many ventures, Cuban is also involved in the world of film and television and occasionally appears on popular television shows including Entourage, Dancing with the Stars, and The League.

Mark graduated from the Kelley School of Business at Indiana University with a degree in management. He lives with his wife and children in Dallas, Texas.

Coaching and Staying Connected:

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Robert Greene is a globally renowned author and thinker best known for his groundbreaking books on power, strategy, and human behavior, including the international bestsellers The 48 Laws of Power, The Art of Seduction, The 33 Strategies of War, and Mastery. But before becoming a literary icon, Robert struggled through decades of uncertainty—working over 50 different jobs, battling self-doubt, and feeling lost in his 30s. It wasn’t until age 37, after years of rejection and frustration, that his life changed with the release of The 48 Laws of Power, a book that would go on to sell millions of copies and influence everyone from CEOs to world leaders and hip-hop legends. In this episode, Robert opens up about the real pain behind his rise, the dangerous truths about power, and the deeply human experiences that shaped his work.

Timestamps:
00:00 – The Psychology of Seduction
11:45 – Overcoming Insecurity and Finding Real Confidence Through Action
19:40 – Modern Dating and Human Disconnection
32:00 – Finding Your Life's Task and Mastery
44:15 – Mentorship and Preparation
51:05 – Final Reflections: Leadership, Regret, and His Most Personal Life Lessons

Resources:
Robert's Instagram
Robert's Website
Sneak Peak of Robert's New Book, The Law of the Sublime

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Robert Greene is a globally renowned author and thinker best known for his groundbreaking books on power, strategy, and human behavior, including the international bestsellers The 48 Laws of Power, The Art of Seduction, The 33 Strategies of War, and Mastery. But before becoming a literary icon, Robert struggled through decades of uncertainty—working over 50 different jobs, battling self-doubt, and feeling lost in his 30s. It wasn’t until age 37, after years of rejection and frustration, that his life changed with the release of The 48 Laws of Power, a book that would go on to sell millions of copies and influence everyone from CEOs to world leaders and hip-hop legends. In this episode, Robert opens up about the real pain behind his rise, the dangerous truths about power, and the deeply human experiences that shaped his work.

Timestamps:
00:00 – Intro and Robert's Get Rich or Die Trying Moment
06:25 – 50 Jobs, Self-Doubt, and a Dream to Write
13:37 – Suicidal Thoughts and The Emotional Cost of Unfulfilled Potential
25:11 – How to Become Powerful and Master Relationships
35:54 – Why You Shouldn’t Follow All 48 Laws—and Who Actually Did
48:49 – Surreal Moments, Paparazzi, and the Prime Minister of Italy

Resources:
Robert's Instagram
Robert's Website
Sneak Peak of Robert's New Book, The Law of the Sublime

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn