Leadership, AI & Chasing Greatness with Rajeev Kapur | The Jason Wright Show

What does it mean to lead well when your whole team has access to the same AI? In this episode, Jason sits down with Rajeev Kapur, CEO of 1105 Media, former Dell executive, MIT-certified AI advisor, and bestselling author, to talk about leadership, entrepreneurship, and how leaders should set the playbook for using AI in their organizations.

Rajeev shares how a 100%-commission job at Gateway 2000 in South Dakota launched his career, how 12 years at Dell took him to Asia, and how he got through COVID with his G.R.E.A.T. leadership framework. He and Jason also cover the difference between a leader and a manager, what to do when a co-founder can't make the shift from employee to owner, and why he thinks human judgment will be the real competitive edge as AI becomes a commodity.

Rajeev had a 45-minute hard stop, so Part Two is coming, recorded in person in Laguna.

In this episode:

• Gateway 2000, Michael Dell, and betting on yourself
• The G.R.E.A.T. framework: Gratitude, Resilience, Empathy, Accountability, Transparency
• Why gratitude only works alongside the other four (the "turkey sandwich" principle)
• Walking one-on-ones, inspired by Steve Jobs
• Giving leaders "rope," and what to do when it backfires
• Leader vs. manager: "What can you do for me?" vs. "What can you do for the organization?"
• Handling a partner who can't leave the employee mindset behind
• Using AI as a virtual advisor: the "Mark Cuban on the morning commute" story
• The AI cheat code: "Interview me like you're Elon Musk"
• Replacing "artificial" with the three A's: Augmenting, Anticipating, and Adapting intelligence
• Why AI's biggest benefit is buying back time
• Intelligence as a commodity: human judgment and context as the edge

Rajeev's books:

• Chase Greatness: Enlightened Leadership for the Next Generation of Disruption (2021): https://www.amazon.com/dp/1642251895
• AI Made Simple: A Beginner's Guide to Generative Intelligence (3rd edition, 2025): https://www.amazon.com/dp/1962017125
• Prompting Made Simple: How to Use ChatGPT and Unlock the Power of AI (2025): https://www.amazon.com/dp/1962017060
• NEW: Intelligence as a Commodity: Human Judgment as a Competitive Advantage (with Jason Hunter, Wiley, December 2026). Available for pre-order: https://www.amazon.com/dp/1394468121
• Coming soon: Liberated By Limits: How Doing More With Less Unlocks Breakthrough (January 2027): https://www.amazon.com/dp/1969905131

Connect with Rajeev:

• LinkedIn: https://www.linkedin.com/in/rajeevkapur1/
• Website: rajeev.ai
• Instagram: @therajeevkapur

Mentioned in this episode:

• Cal Newport's Deep Questions podcast
• Good to Great, Jim Collins
• Blue Ocean Strategy, W. Chan Kim & Renée Mauborgne
• Time Rich
• YPO (Young Presidents' Organization)

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