81. Legacy, Leadership & Letting Go: Jeni Hott on Mindset, AI, and Meaningful Entrepreneurship

In this deeply inspiring and wide-ranging episode, Dwayne sits down with digital pioneer and serial entrepreneur Jeni Hott. What starts as a casual catch-up unfolds into a powerful conversation about life transitions, emotional intelligence, mindset mastery, and the future of business. Jeni shares her spontaneous decision to uproot her life, her son’s incredible generosity, and the legacy we leave behind—not just in business, but in how we live. They also dive into leadership identity shifts, how to handle negativity in business, and why embracing AI is not optional but essential.

Whether you're a new entrepreneur or a seasoned leader navigating uncertainty, this episode is packed with wisdom, heart, and actionable insight.

Timestamps:

00:00 – Opening remarks and the chaos of moving

02:00 – Jeni’s health scare and the wake-up call from the universe

04:00 – Giving everything away: a touching story of legacy and generosity

06:30 – Joy in everyday moments and the theme of intentional kindness

09:00 – Why business is always about relationships

10:30 – Introducing Jeni: Her trailblazing blogging success and career highlights

12:00 – From nursing to naturopathic doctorate to entrepreneurship

13:30 – The underestimated power of mindset in business

15:00 – Scarcity vs abundance: where business owners get stuck

17:00 – The identity shift from entrepreneur to leader

21:30 – What defines a true leader and how to grow into it

24:00 – Releasing limiting beliefs: The Sedona Method & Hale Dwoskin

28:00 – Observing vs suppressing emotion in entrepreneurship

30:00 – Waking Up app by Sam Harris & third-party mindfulness tools

32:00 – Business mindset vs strategy: finding balance

33:30 – Entering the AI Era: Why business owners must adapt

36:00 – Breaking down AI in simple terms (ChatGPT, GPTs, LLMs)

42:00 – Creating your own company-specific GPT (custom AI tools)

48:00 – Instructional designers & the future of team training

53:00 – How to simplify your operations with AI + training systems

56:00 – Hiring a VA and the stages of team evolution

1:01:00 – Keeping it lean: How Jeni ran a 7-figure business with minimal staff

Notable Quotes:

“Legacy is when you pass on that mission, that purpose, and that generosity. That’s what life is really about.”

“If it doesn’t feel good, it’s probably not true. Most of your limiting beliefs are just your brain trying to keep you comfortable.”

“Every entrepreneur hits that point where they must decide: will I be the bottleneck or the breakthrough?”

“AI isn’t replacing you—it’s extending your potential.”

“You don’t need a massive team to be massively successful. You need systems that work.”

Valuable Resources & Takeaways: 

Mindset Tools:

• The Sedona Method (Hale Dwoskin)
• Waking Up app (Sam Harris)
• "Do the Work" App (Marie Hayes)

AI & Business Tools:

• ChatGPT & Custom GPTs
• Instructional Design Support: Kate Nash
• OBM & VA Hiring: MaryRose Speed’s VA Academy
• Online Business Structure: Time Rich Program by Jeni Hott

Connect with Dwayne Kerrigan

Linked In: https://www.linkedin.com/in/dwayne-kerrigan-998113281/

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