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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Episode description

Wade Myers grew up in the Badlands of western North Dakota in a Mennonite home with no electricity, no indoor plumbing, and no telephone. He was selling door to door at age nine. He went on to become an Army Ranger, served in the Gulf War, earned an MBA from Harvard Business School, and built a career as one of the most successful entrepreneurs and investors around.

In this episode of the Texas Titans podcast, Jason Wright and Wade talk about why he left corporate America, how a handshake deal with a mentor launched his career, what he looks for before writing a check, and how he ended up backing the faith-based hit I Can Only Imagine.

In this episode

• Growing up in the “land of extremes” and earning everything he wanted, including the store-bought clothes he paid for as a sixth-grade roofer’s assistant
• Why a Harvard study found entrepreneurs make less money than corporate executives but are far happier
• The investor lunch that tore apart Wade’s first pitch, and the mentor who backed him anyway on an 80/20 handshake deal
• Lessons from his first acquisitions: cash flow, losing the biggest customer in week two, and learning what HBS doesn’t teach
• Why Wade prefers to back serial entrepreneurs, and how the Dunning-Kruger “unconscious incompetence” stage trips up first-timers
• How founders respond to diligence, and why humility and teachability can make or break a deal
• The Ranger knife-fight lesson: go in knowing you will get cut
• Practical advice for aspiring entrepreneurs: cut fixed expenses, prepare your family, start on nights and weekends, and “go get one customer”
• Teaching kids gross margin with a whiteboard, a car-wash business, and a SaaS company
• Build vs. buy: seed-stage investing, bolt-on acquisitions, and public equities
• How backing the Erwin brothers led to Mom’s Night Out, Woodlawn, and I Can Only Imagine
• Wade’s daily routine: 4 a.m. prayer and planning, the gym at 5, and 10 to 15 Blinkist summaries a week

Notable quotes

• “Entrepreneurs are the only people who will work 90 hours a week to avoid working 40 hours a week for somebody else.” (Phil Burks, as quoted by Jason)
• “Go get one customer. Do that for me. Tell me what you learn. Now go get 10.” (Wade Myers)
• “Wisdom comes from experience, and experience comes from making mistakes.” (Wade Myers)

The Jason Wright Show — Jacob Baadsgaard: How to Become (and Hire) the Indispensable Marketer

On the day his new book The Indispensable Marketer launches, Jacob Baadsgaard joins Jason for something closer to a coaching session than an interview. Jacob is the founder and sole owner of Disruptive Advertising. Over 14 years the agency has served 2,000+ companies, managed more than $3 billion in ad spend, and generated a couple hundred million in revenue. Jacob explains why founders and their marketers so often end up pointing fingers at each other. He walks through the math every CEO owes their marketing team, and makes the case that AI is helping a lot of marketers do the wrong work faster. The conversation then gets personal: ambition as addiction, a lizard named Roger, and what happened when Jacob started treating his wife’s dreams the way she had always treated his.

In this episode:

• Why CEOs pick the winning ad headline only about 10% of the time, and what to do with your passion instead
• The 1-to-1-to-1 rule: one target customer, one message, one landing page
• “Green marketing numbers, red bank account”: the business math founders skip
• The 3% rule and the 7-stage customer journey, and why you should build it from the bottom up
• How Jacob nearly hired his seventh head of marketing, and how he and Chad turned it around instead
• Knowledge is commoditized. Experience is what makes your brand human.
• The difference between an addiction and a worthy goal

Chapters

• 00:00 Book launch day and a coaching-style conversation
• 01:13 Jacob’s origin: Omniture/Adobe analytics, then 14 years building Disruptive Advertising
• 04:34 Data vs. founder intuition: meet customers where they are
• 07:41 “It’s for everyone”: competition and the 1-to-1-to-1 rule
• 12:26 How to vet a marketer: business math, LTV, and setting the destination
• 18:12 Only 3% are ready to buy today: building the full funnel
• 22:40 Why he wrote The Indispensable Marketer (and the story of his sixth marketing leader)
• 28:00 AI slop, doing the wrong work faster, and why experience beats knowledge
• 32:50 The outlook: expensive debt, purpose-driven businesses, and “I’ll be happy when…”
• 36:40 Having enough, time with kids, and Roger the lizard
• 41:08 Jacob’s morning routine (and the hand pan)
• 44:46 Becoming your spouse’s biggest fan
• 50:56 Where to find Jacob and the book

Quotable

• “If you’re marketing to everyone, you’re marketing to no one.”
• “They’re doing the wrong work faster with AI.”
• “A worthy goal is something you’d sign up for even if the outcome wasn’t guaranteed.”

Connect with Jacob

• LinkedIn: Jacob Baadsgaard
• Agency: Disruptive Advertising — disruptiveadvertising.com
• Book: The Indispensable Marketer