AI isn’t just another tool — it’s a multiplier. But most business owners are missing the mark completely.

Jeff MacPherson is a three-time tech founder, the creator of the first Instagram DM chatbot (yes, the one that handled nearly a billion messages), and now the co-founder of XnGen AI. He helps businesses turn their internal IP into scalable AI systems that drive real profit.

In this episode, Jeff shares how business owners can stop chasing shiny tools and start building real leverage — even if they have no clue where to begin with AI.

We talk about:
🔹 Why AI is an intern, not a savior
🔹 The DNA framework: Data, Nurture, Automation
🔹 How to build your own internal “AI Cloud”
🔹 The mistake of plugging AI into broken systems
🔹 How to train AI to onboard your next hire
🔹 Where most founders get stuck (and how to break free)

Whether you’re curious, cautious, or already experimenting, this is the conversation to help you build smarter and buy back your time.

Quotes from the Episode:
💬 "AI is an intern, not a magic bullet."
💬 "Build your own AI cloud — not someone else’s tool."
💬 "Freedom isn’t working less. It’s working on what matters."
💬 "Most businesses don’t have an AI problem. They have a friction problem."
💬 "You can’t train AI without training your team first."

Actionable Takeaways:
✅ Start with your internal knowledge: SOPs, values, mission, strategy
✅ Centralize it in a simple tool like Airtable or build your AI cloud
✅ Train AI on real business data, not prompts off the internet
✅ Assign someone to own AI on your leadership team
✅ Focus on one workflow. Get results. Then scale.

Resources from this episode:
→Connect with Jeff: https://www.linkedin.com/in/jeffmacai/
→ Learn about XnGen AI: https://www.xngen.ai/
→ Matt Farmer AI: https://www.instagram.com/mattfarmerai

Like what you heard?
Subscribe wherever you get your podcasts and leave a review. It helps more business owners build freedom-first companies.

🎧 If this episode made you rethink how to use AI in your business, subscribe, share, and leave a review. For more conversations on purpose, people, and building companies that last, visit www.jeanmoncrieff.com.

In this episode of The Freedom Experience, I sit down with Bill Mills — CEO of Executive Group, award-winning author of Breakthrough: The Power of Conscious Conversation, and creator of The Leadership Process™.

Bill brings decades of hands-on experience working with CEOs, leadership teams, and peer groups to help business owners build organizations that are indispensable to their customers — and no longer dependent on them to run.

In this conversation, we go beyond theory. Bill shares real stories and simple tools that leaders can use to close the execution gap, drive focus, and build margin-strong businesses that scale without burning people out.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

🔹 Closing the Execution Gap
Why 78% execution is a red flag, not a win — and how to use a century-old force field exercise to remove friction, drive alignment, and finish strong.

🔹 Becoming Indispensable
The question that stops CEOs in their tracks: “Who would cry at your funeral?” Bill unpacks what it takes to become a strategic partner to your customers — and earn 70%+ margins doing it.

🔹 Letting Go of Control
Delegating isn’t the goal — sharing control is. Bill explains how to shift managers from bottlenecks to catalysts and build a culture of ownership across the team.

🔹 Focus Over Complexity
Why chasing every shiny object kills momentum, and how one CEO went from $20M to $200M by going all-in on a single customer problem.

🔹 Freedom and Leadership
Bill shares what freedom means to him — and how real freedom shows up when you stop doing it all yourself and start sharing ownership with your team.

Quotes from the Episode:

💬 "If 80% of your priorities get done, the 20% you missed probably held all the value."
💬 "When your business disappears and the customer doesn’t blink, that’s a problem."
💬 "Freedom is when you own the business — it doesn’t own you."
💬 "You don’t have an execution problem. You have a friction problem."
💬 "You can’t chase two rabbits. Focus is the difference-maker."

Links & Resources Mentioned:

🌍 Executive Group: https://executivegroup.com
📘 Breakthrough: The Power of Conscious Conversation
🎓 Tom Foster on Role Complexity & Leadership
📊 Gallup Research on Manager Effectiveness
📈 The 10x CEO Study (via Inc. Magazine)

Actionable Takeaways:

✅ Diagnose the Gap: Use a force field analysis to identify what’s driving results — and what’s holding your team back.
✅ Stop Being Replaceable: Build a business your customers can’t imagine living without.
✅ Share the Wheel: Real power-sharing builds trust and drives scale.
✅ Build Around One Problem: Nail the one thing you solve better than anyone else — and scale from there.
✅ Rethink Execution: It’s not about doing more. It’s about doing the right things — all the way through.

🎧 If this episode made you think differently about leadership, growth, or freedom — subscribe, share, and leave a review.
For more conversations on purpose, people, and building businesses that last, visit www.jeanmoncrieff.com.

In this episode of The Freedom Experience, I sit down with Elizabeth Glasbrenner — CEO of Smiley Technologies, a family-owned business providing core banking software to community banks and financial institutions.

Elizabeth’s story is one of courage, clarity, and people-first leadership. After co-founding the business in 2002 with her brother Vance and father Walter, she stepped into the CEO role in 2016 — not just to scale the company, but to rebuild trust, reshape the culture, and guide the business through a period of rapid growth.

In this conversation, Elizabeth opens up about what it took to make that transition. From navigating imposter syndrome to balancing extreme personal challenges — including her husband’s Everest expedition and her daughter’s life-threatening health issues — she shares what it really looks like to lead with empathy and authenticity, even when the stakes are high.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

🔹 The Leadership Shift
Why the leader who starts the business isn’t always the one to scale it — and how Elizabeth found her own leadership voice.

🔹 Building Trust from the Inside Out
How Elizabeth rebuilt trust in the organization after stepping into her brother’s shoes — and why listening was her first strategy.

🔹 Leading Through Personal Crisis
Balancing high-stakes leadership with an intense family situation — and the strength that came from showing up fully in both.

🔹 Quiet Strength
Why vulnerability, empathy, and consistency became her edge — and how that reshaped the culture at Smiley Technologies.

🔹 Freedom and Leadership
What freedom means when you're responsible for others — and how Elizabeth learned to lead in a way that aligned with her values.

Quotes from the Episode:

💬 "You don’t need to know all the answers. You need to ask the right questions."
💬 "Trust is everything. Without it, nothing moves."
💬 "I thought I had to prove myself. What I really needed to do was show up as myself."
💬 "Listening was the most powerful thing I did as a new CEO."
💬 "Freedom is finding calm in the chaos."

Links & Resources Mentioned:

🌍 Smiley Technologies: https://www.smileytechnologies.com
📲 Connect with Elizabeth: https://www.linkedin.com/in/elizabeth-glasbrenner/

📚 Books Mentioned
– The Speed of Trust by Stephen M.R. Covey
– Dare to Lead by Brené Brown
– Quiet by Susan Cain

Actionable Takeaways:

✅ Step Into the Role: You don’t need to be the same kind of leader as your predecessor — just the one your business needs next.
✅ Lead with Empathy: Listening is often more powerful than directing.
✅ Rebuild from Trust: Sustainable growth starts inside the team.
✅ Embrace Your Season: Life and business don’t happen in separate lanes — lead with full presence.
✅ Redefine Success: It's not about doing more — it's about doing what matters most.

🎧 If this episode made you think differently about leadership, growth, or freedom — subscribe, share, and leave a review.
For more conversations on purpose, people, and building businesses that last, visit www.jeanmoncrieff.com.

In this episode of The Freedom Experience, I sit down with Kelly O’Finnell—President of EFS ESOP Consultants, author of The ESOP Coach, and one of the leading voices in employee ownership and business succession planning.

With over four decades in the field, Kelly has helped countless business owners transition their companies into ESOPs (Employee Stock Ownership Plans), creating incredible wealth and preserving company culture. In our conversation, we explore how ESOPs aren’t just an exit strategy—but a powerful tool to build legacy, drive alignment, and close the wealth gap for employees. Kelly shares real-world stories, including one about a mailroom employee who walked away with over $4 million, and lays out why ESOPs are increasingly relevant in today’s world of aging business owners and cultural misalignment with third-party buyers.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

🔹 The Power of ESOPs
ESOPs aren’t just retirement plans—they're a wealth creation vehicle that protects employees, sustains culture, and offers business owners full value without sacrificing legacy.

🔹 Succession Without Selling Your Soul
Kelly explains how ESOPs serve as an internal transition strategy that allows owners to stay involved while rewarding the people who built the business with them.

🔹 Tax Benefits & Financial Strategy
We break down the two major tax advantages of ESOPs, including how 100% ESOP-owned S-Corps can operate tax-free.

🔹 Creating Cultural Alignment
Why culture is one of the most vulnerable parts of a traditional sale—and how ESOPs ensure continuity and employee engagement for the long haul.

🔹 Keys to Successful Implementation
From employee education to communication plans and feasibility studies, Kelly shares what it really takes to make an ESOP thrive.

💬 "ESOPs can change lives."
💬 "It's a way to exit without selling your soul."
💬 "An ESOP can close the wealth gap."
💬 "You can't be Gordon Gekko just focused on yourself."
💬 "You have a fiduciary obligation to run this business."
💬 "You can operate your business without tax consequences."
💬 "Cultural alignment is crucial to ESOP success."
💬 "When employees become owners, everything changes."

🌍 Kelly’s Website: https://www.efsconsultants.com
📚 Book: The ESOP Coach – Available on Amazon
🔗 Connect with Kelly on LinkedIn: https://www.linkedin.com/in/kellyofinnell/

✅ Think Legacy: ESOPs give you a way to exit while preserving the identity and values of your company.
✅ Explore Your Options: Selling to private equity isn’t your only path—consider internal transitions.
✅ Invest in Education: ESOP success depends on consistent employee communication and engagement.
✅ Plan Ahead: Start with a feasibility study to see if your company is the right fit.
✅ Shift Your Mindset: From owner to steward—align your leadership with a new generation of employee-owners.

🎧 If this episode inspired you, subscribe, share, and leave a review.
For more insights on leadership, succession, and building a legacy of freedom, visit www.jeanmoncrieff.com.

In this episode of The Freedom Experience, I sit down with Amy Courter—former national commander and CEO of the Civil Air Patrol, where she led 61,000 volunteers as a two-star Major General. Amy's leadership journey is nothing short of extraordinary, from the Pentagon to tech startups, from taking a company public to coaching leadership teams as an EOS Implementer.

We explore why vision is a leader’s most important compass, the power of vulnerability-based trust, and how healthy conflict builds strong, resilient teams. Amy shares how her parents shaped her entrepreneurial spirit, what it means to lead with values, and why your front-line employees' micro-decisions reveal the real culture of your business.

If you’re leading a team, navigating a career transition, or building a values-driven business—this episode is packed with lessons you won’t want to miss.

🎥 Watch this conversation on YouTube. And don’t forget to SUBSCRIBE!

🔹 Leading with Vision & Values
Amy reveals why vision isn’t optional—it’s essential. If leaders can’t clearly define and live the vision, neither will their teams.

🔹 Vulnerability-Based Trust & Healthy Conflict
Learn how high-performing teams create space for tough conversations and why trust is the foundation for real accountability.

🔹 From Corporate to Entrepreneurial Leadership
Amy shares how growing up with entrepreneurial parents influenced her career—from massive corporations to agile coaching today.

🔹 Micro-Decisions & Organizational Culture
The decisions made by frontliners—often unconsciously—reflect whether your company truly lives its core values.

🔹 Intentionality & Saying “No”
In a world of endless opportunity, Amy explains why “No” is a whole sentence—and a critical one for staying focused and free.

💬 "Vision is important—and if I don't believe in it, I walk away."
💬 "We need to have healthy conflict."
💬 "Team health really is an important part of leadership."
💬 "Freedom for me is that ability to make choices."
💬 "Storytelling is how we bring the vision to life."
💬 "No is a whole sentence."

🔗 Connect with Amy Courter on LinkedIn: linkedin.com/in/amycourter
📘 Book Mentioned: Shine by Gino Wickman & Rob Dube
📘 Book Mentioned: The Five Dysfunctions of a Team by Patrick Lencioni
📘 Book Mentioned: The 6 Types of Working Genius by Patrick Lencioni

✅ Lead with Vision – Set and share a compelling direction for your team.
✅ Build Vulnerability-Based Trust – Foster open, honest conversations without fear.
✅ Pressure Test Your Core Values – Do your decisions match your words?
✅ Watch the Micro-Decisions – Culture is shaped by how everyday choices get made.
✅ Say “No” More Often – Protect your time, energy, and freedom by staying focused.
✅ Keep Climbing – Success isn’t the end—there’s always another mountain ahead.

🎧 Enjoyed this episode? Subscribe, share, and leave a review to help us bring more real conversations and actionable leadership insight your way.

For more resources and expert interviews, visit www.jeanmoncrieff.com.

In this episode of The Freedom Experience, I sit down with Joel Trammell—Chairman and Founder of CEO-S, author of The CEO Tightrope and The Chief Executive Operating System, and a seasoned entrepreneur who has spent over three decades in the CEO seat.

Joel shares hard-earned wisdom from scaling startups to leading a billion-dollar public company. We dive into the unique mindset shifts that CEOs must make as their companies grow—from wearing every hat in a 20-person startup to leading a functional executive team in a 150+ person organization. Joel introduces his Triangle of Tension framework, explains how CEOs can unlock clarity and communication, and explores why emotional intelligence and self-awareness are vital in the pursuit of personal and entrepreneurial freedom.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

🔹 The Triangle of Tension
Joel breaks down the constant balancing act CEOs must perform between customers, employees, and shareholders—and why ignoring any one of them can lead to failure.

🔹 Scaling the CEO Role
From 1 to 150 employees, the CEO job transforms radically. Joel outlines the three key growth phases and what founders must do to avoid becoming the bottleneck in their business.

🔹 Clarity and Communication
Joel emphasizes why clarity in roles, KPIs, and communication is the true superpower of a successful CEO. We also explore how a CEO User Manual can help build stronger leadership teams.

🔹 Understanding Personality Types
You can’t lead everyone the same way. Joel shares how tools like DiSC and CliftonStrengths help leaders tailor communication and improve team dynamics.

🔹 Emotional Intelligence & Self-Awareness
Leadership isn’t just about strategy. Joel explains why mastering your inner game is critical to thriving in the CEO seat—and why entrepreneurship is as much a path to freedom as it is a challenge in resilience.

Quotes from the Episode:

💬 "CEOs are actually weird."
💬 "The organization ran like crap."
💬 "The job is totally different."
💬 "What do I do Monday morning?"
💬 "It's a constant balancing act."
💬 "Don't read between the lines."
💬 "Communication is what the audience hears—not just what you say."
💬 "You have to functionalize."
💬 "There is a solution."

Links & Resources Mentioned:

🌍 Joel’s Website: https://www.theceooperatingsystem.com
📚 Books: The Chief Executive Operating System | The CEO Tightrope
🔗 Connect with Joel on LinkedIn: https://www.linkedin.com/in/joeltrammell/

Actionable Takeaways:

✅ Embrace the Transition: Understand how your role evolves from startup leader to enterprise CEO.
✅ Clarify Roles & KPIs: Create clear metrics and responsibilities for your executive team.
✅ Balance the Triangle: Stay strategic in managing stakeholder tension.
✅ Communicate with Intention: Tailor your leadership style to different personality types.
✅ Prioritize Personal Growth: Emotional intelligence and self-awareness are foundational to success.

🎧 If this episode resonated with you, subscribe, share, and leave a review.
For more insights on leadership, growth, and reclaiming your freedom, visit www.jeanmoncrieff.com.