Tasty Catering's Cultural Revolution and Entrepreneurial Spirit

In this episode of The Freedom Experience® Podcast, I sit down with Tom Walter, Founder, CEO, and Chief Culture Officer at Tasty Catering. Tom is a true serial entrepreneur, having grown Tasty Catering from its humble beginnings as a Chicago hot dog stand into one of the top four catering companies in Chicago, with group revenues surpassing $85 million.

Tom's story is one of transformation, driven by a deep belief in the power of relationships, culture, and people. In this conversation, we dive into the cultural revolution that took place at Tasty Catering in 2005, when two young employees challenged Tom’s leadership style. Their call for change was the catalyst for a complete turnaround, resulting in a more people-centered, values-driven company that continues to thrive.

Tom shares how hitting rock bottom, both personally and professionally, forced him to rethink how he led the business. With a renewed focus on fostering an entrepreneurial spirit within the team, Tasty Catering went from $2-3 million in revenue to $85 million today.

The driving force?

Tom's emphasis on understanding people’s skills, creating a values-based culture, and removing workplace "disruptors" that prevent employees from performing at their best.

One of the standout concepts we discuss is the idea of "entangled employees"—people who are deeply woven into the fabric of the company and who think and act like owners. Tom shares how empowering his team to take responsibility for their own areas of work and decision-making has led to innovation and incredible growth, especially during challenging times like COVID-19.

Key Takeaways:

• The Power of Culture: Building a company culture based on core values can transform both the business and the people within it. Tom’s 2005 cultural revolution was the turning point for Tasty Catering.
• Discretionary Effort: The average employee only gives 4% of their 60,000 daily thoughts to their employer. By removing disruptors and fostering a positive, values-driven workplace, Tom has helped his employees unlock their full potential.
• Circle of Discipline: Tom shares how freedom within a framework allows employees to take ownership of their roles, empowering them to innovate and drive the business forward.
• Entangled Employees: Beyond engagement, entangled employees are those who care deeply about the company's success and contribute extra discretionary effort. During COVID-19, Tom felt like he had 60 CEOs in the room, all working together to find solutions.

Resources:

• Connect with Tom Walter on LinkedIn
• Explore Tasty Catering and learn about its unique culture
• Read more about Tom's leadership philosophy in It's My Company Too!

This episode is a must-listen for any entrepreneur or business leader looking to transform their company culture and foster an environment where employees thrive and contribute at their highest potential.

Books:

1. "Good to Great" by Jim Collins – This book is central to the cultural change that took place at Tasty Catering, with the team using its principles to shape core values and drive growth.
2. "The 8 Steps of Change" by John Kotter – Though Tom initially didn’t know about Kotter’s framework, the change process at Tasty Catering followed Kotter's 8-step model of transformation.
3. "It's My Company Too!" – Co-authored by Tom Walter, this book explores what makes small companies great, with a focus on employee engagement and culture.
4. "Creating a Culture of Accountability" (Gravitas Impact Monograph) – Though not mentioned directly, this is related to the principles Tom discussed about accountability and leadership.
5. "The Great Game of Business" by Jack Stack – Tasty Catering uses the financial transparency and open-book management principles from this book to involve all employees in the company’s success.
6. "The Big Hairy Audacious Goal (BHAG)" from Good to Great – This concept was part of the culture-building at Tasty Catering, shaping its long-term vision.

Thought Leaders:

1. Jim Collins – Author of Good to Great, Collins’ work on core values and the BHAG (Big Hairy Audacious Goal) concept significantly influenced the cultural shift at Tasty Catering.
2. John Kotter – His 8-step process for leading change was mirrored in Tasty Catering's transformation, even though Tom wasn’t initially aware of it.
3. Edgar Schein – A renowned thought leader in organizational culture, Schein’s "pyramid model for culture" deeply influenced how Tasty Catering embedded values into the company.
4. Immanuel Kant – Tom references Kant’s philosophy of freedom within discipline, which shaped Tasty Catering’s "Circle of Discipline" approach to employee empowerment.
5. Ari Weinzweig – Co-founder of Zingerman's Deli and a fellow Small Giants leader, Tom mentions that Weinzweig personally teaches his company's culture courses, inspiring Tom’s approach at Tasty Catering.
6. Bo Burlingham – Author of Small Giants, Bo’s work on great companies that prioritize values over size also influences Tom’s business approach.
7. Sue Funkhouser – An organizational development specialist who spoke at a Small Giants gathering, Sue provided insights into the impact of culture on discretionary effort and employee engagement.

These books and thought leaders play a significant role in shaping Tom Walter's leadership philosophy and the culture at Tasty Catering.

Empowering Entrepreneurs with Financial Wisdom

In this episode of The Freedom Experience, I sit down with Mackey McNeill, a trailblazing entrepreneur and financial expert, to explore the challenges faced by business owners and the critical role of financial planning in business success. Mackey shares her unique journey of building a successful business, the importance of intention in achieving business goals, and how fear can drive poor decision-making for entrepreneurs.

As the founder of Mackey Advisors, a CFO firm for fast-growing businesses and those striving for intentional growth, Mackey brings more than just numbers to the table—she brings heart, purpose, and decades of experience helping business owners thrive.

A CPA, PFS, and the award-winning author of The Prosperity Playbook and The Intersection of Joy and Money, Mackey has guided thousands of entrepreneurs through the ups and downs of building a successful business. Her insights have appeared in INC Magazine, The Wall Street Journal, The New York Times, and Money, to name a few.

Mackey Advisors isn’t just another financial firm. It was one of the first certified B Corps in its region, a four-time Real Leaders Impact Award winner, and even earned a place on the INC 5000 in 2022. In 2023, they added the INC Power Partners award to their accolades—a testament to their commitment to helping businesses grow with intention.

When she's not helping others find prosperity, Mackey is living hers—spending time at her permaculture homestead, RedSunflower Farm, where she loves to cook straight from her garden, wander the woods, and cherish moments with her grandchildren.

In this episode:

Mackey introduces her innovative framework that empowers entrepreneurs to make data-driven decisions through integration and strategic planning. She also emphasizes the importance of building a team capable of running a business independently. She shares how this allowed her to step away from daily operations and focus on long-term growth. The conversation touches on leadership, succession planning, and maintaining core values in scaling a business.

Key Takeaways:

• Intention and financial planning are critical for business success.
• Fear-driven decisions often lead to poor outcomes.
• Integration of financial data with strategic planning helps entrepreneurs make informed decisions.
• Building a team that operates independently fosters sustainable growth.
• Transparent communication and education around financials build stronger teams and better results.

Connect with Mackey:

• LinkedIn: Mackey McNeill
• Website: Mackey Advisors

Culture as Strategy: How Purpose and Values Drove a 22x Valuation

Paul Spiegelman is the co-founder of the Small Giants community, a peer group of purpose-driven business leaders. As the former chief culture officer of Stericycle and co-founder/former CEO of Beryl Health, Paul has pioneered approaches to building culture-first organizations. His journey from founding a medical alert business in the mid-1980s to selling Beryl Health for 22x EBITDA demonstrates how purpose-driven leadership can create exceptional business value while prioritizing people.

In this episode of The Freedom Experience, Paul and I explore the connection between purpose, culture, and business success. We discuss how putting employees first creates sustainable growth, the challenges of maintaining culture through transitions, and the personal journey of finding purpose after a successful exit. If you're interested in building a business that makes a difference while delivering exceptional results, this conversation is for you.

Watch the Episode on YouTube. And SUBSCRIBE!

Key Takeaways:

• The Circle of Growth: Paul explains his proven model where focusing on employees first drives customer loyalty, which generates profit that can be reinvested in people.
• Culture as Competitive Advantage: Learn how Beryl Health commanded 20-30% premium pricing while achieving 5-6x higher profitability than competitors by prioritizing culture.
• Navigating Transitions: Paul shares insights on protecting company culture through growth and acquisition, including his decision to reject private equity offers.
• Finding Purpose: We discuss the ongoing search for purpose, managing mental health as a leader, and maintaining fulfillment after a successful exit.
• Next Generation Leadership: Valuable advice for emerging leaders on building relationships, staying patient with career development, and seeking mentorship.

Resources and Links:

• Connect with Paul Spiegelman on LinkedIn
• Join the Small Giants Community at www.smallgiants.org
• Contact Paul directly at paul@smallgiants.org
• Books by Paul Spiegelman:
  • Small Giants
  • Why is Everyone Smiling?
  • Patients Come Second
• Mentioned in this episode:
  • Beryl Health
  • Stericycle
  • Small Giants Community Leadership Academy

Breaking Growth Barriers Through Market Focus

Art Saxby is the founder and CEO of Chief Outsiders, a company revolutionizing how mid-sized businesses access executive talent through fractional leadership. From his early days as a "born nomad" to leadership roles at Frito-Lay, Kellogg's, and Coca-Cola, Art has mastered the art of thriving in new situations. At age 50, driven by necessity during the 2009 recession, he founded Chief Outsiders, which now boasts over 130 battle-tested marketing and sales executives helping companies reignite growth.

In this dynamic episode of The Freedom Experience, Art shares his proven "Growth Gears" methodology and reveals why even the best-run companies sometimes struggle to grow. Whether you're plateauing, seeking new market opportunities, or preparing for the economic upswing predicted for 2025, this conversation offers invaluable insights for business leaders ready to accelerate growth.

Watch the Episode on YouTube. And SUBSCRIBE!

Key Takeaways:

• The Three Growth Gears: Art breaks down the essential components of sustainable growth - Insights, Strategy, and Execution - and why they must work in harmony
• Market-Based Leadership: Learn why looking outward at market dynamics is crucial for breaking through growth plateaus
• Culture as Strategy: Discover how purpose-driven culture can be strategically designed to deliver business results
• Future-Ready Leadership: Understanding how AI, flexible work arrangements, and economic cycles are reshaping business opportunities
• Resource Optimization: Why the future belongs to companies that can flexibly access world-class talent rather than trying to own every resource

Resources and Links:

• Connect with Art Saxby on LinkedIn
• Visit Chief Outsiders at chiefoutsiders.com
• Books Mentioned:
  • Growth Gears by Art Saxby and Pete Hayes
  • Stop Random Acts of Marketing by Karen Hayward
  • Good to Great by Jim Collins
• Organizations Referenced:
  • Vistage
  • C12
  • ITR Economics

Want to prepare your business for the growth opportunities ahead? Don't miss Art's practical insights on building market-driven organizations that can quickly adapt and scale.

The Hidden Truth About Purpose at Work

The Hidden Truth About Purpose at Work with Zach Mercurio

In this powerful conversation with Zach Mercurio, we explore why purpose isn't just about having a mission statement - it's about creating environments where people truly feel they matter. Zach shares insights from his research and upcoming book about how leaders can build cultures of significance in their organizations.

🔑 KEY TAKEAWAYS:

• Purpose exists in every role - it's about connecting work to human impact
• Creating purpose statements is only 1% of the work - implementation is key
• Leaders need specific skills to help people see their significance
• The future of work is moving toward a relationship economy
• Less than 1% of people receive formal education in listening skills
• Psychological safety, meaningfulness, and availability are key predictors of engagement
• Digital communication is eroding our human connection skills

⚡ KEY MOMENTS:

[03:28] Zach shares the poem that changed his perspective on purpose [05:27] Why your job isn't your purpose [12:54] How embedded purpose serves as a storyline for organizations [17:03] The NASA story - how to show people their work matters [20:30] Rethinking job descriptions through a purpose lens [26:01] The two fundamental truths about employee engagement [36:08] How the Industrial Revolution disconnected us from purpose [46:09] Why purpose statements alone aren't enough

💡 POWERFUL QUOTES:

"Your purpose is not out there waiting to be found. It's right where you are waiting to be acknowledged and seen."

"It's impossible for something to matter to someone who doesn't first believe that they matter."

"When you have an embedded purpose, it serves as that storyline. But when you don't have that purpose, you get a lot of wasted energy and a lot of confusion."

📚 ABOUT ZACH: Zach Mercurio, PhD, is a researcher, author, and speaker specializing in purposeful leadership and positive organizational psychology. He works with organizations worldwide, including:

• Delta Airlines
• J.P. Morgan Chase
• Marriott International
• The Government of Canada
• The National Park Service

As a Research and Teaching Fellow at Colorado State University's Center for Meaning and Purpose and one of Simon Sinek's Optimist Instructors, Zach brings both academic rigor and practical application to his work.

🔮 WHAT'S NEXT: Pre-order Zach's new book "The Power of Mattering: How Leaders Can Create a Culture of Significance" (Coming May 2025)

🔗 CONNECT WITH ZACH:

Website: https://www.zachmercurio.com/
LinkedIn: https://www.linkedin.com/in/zachmercurio/

📚 RESOURCES MENTIONED:

• "The Invisible Leader" by Zach Mercurio
• "Everything Else in the World" poem by Stephen Dunn
• "Song of Significance" by Seth Godin

🎧 LISTEN ON: iTunes, Spotify

Finding Your True Self

Rob Dube's entrepreneurial path revealed a powerful truth: sustainable success starts from within. After building imageOne into a Forbes Small Giant, he discovered meditation and mindfulness weren't just personal practices - they transformed his leadership. Today, through the 10 Disciplines, his books "Shine" and "donothing," and his leadership retreats, Rob helps driven entrepreneurs find that elusive balance between remarkable business results and inner peace. His approach shows how slowing down, through practices like meditation and ten-year thinking, actually accelerates meaningful success.

In our conversation, we explore the complexities of leadership, the journey to finding one's true self, and the importance of long-term thinking in entrepreneurship. We discuss the fears that leaders often face, the impact of societal expectations, and the significance of embracing the messy path of personal and professional growth.

Watch this conversation on YouTube. And SUBSCRIBE!

🔑 KEY TAKEAWAYS:

• Your true self is unshaped by societal expectations and professional roles
• Ten-year thinking helps slow down time and make better decisions
• Every business goes through predictable cycles over 10 years
• Being still is essential for connecting with your true self
• Understanding your "100%" is crucial for sustainable leadership
• Making decisions from love rather than fear transforms leadership
• What appears as "messy" is actually a beautiful process of growth

⚡ KEY MOMENTS:

00:00  Navigating Leadership Fears
03:02  The Journey of Entrepreneurial Freedom
06:00  Understanding the True Self
08:54  The Impact of Societal Expectations
11:47  The Weight of Secrets in Leadership
15:06  10-Year Thinking: A Long-Term Perspective
17:47  Embracing the Messy Path
21:12  Finding Clarity in the Present Moment
24:02  Lessons from Entrepreneurial Journeys
31:18  Defining Company Values and Culture
36:04  Navigating Leadership Transitions
38:59  Shifting Perspectives on Business Ownership
42:17  The Importance of Being Still
51:16  Letting Go of Identity and Embracing Change

💡 POWERFUL QUOTES:

"We oftentimes don't want people, especially in leadership roles, to recognize that we're actually afraid right now..."

"In a ten-year cycle, you're going to have two great years, six really decent years, and two years that could literally put you out of business."

"We're all unique, but one thing we all need is to be still. We have to let our minds and our bodies settle. We have to let our souls, our true self, catch up."

📚 ABOUT ROB:

Rob Dube is an author, speaker, and entrepreneur whose company imageOne has been recognized as:

• One of Forbes' 25 Top Small Giants in America
• An Inc. Magazine Best Place to Work
• The #1 Top Workplace in Michigan

He's the author of "Do Nothing" and co-author of "Shine" with Gino Wickman, focusing on helping entrepreneurs find true freedom through inner work.

🔮 WHAT'S NEXT:

Explore Rob's 10 Disciplines program and group coaching opportunities

🔗 CONNECT WITH ROB:

• Rob's website
• LinkedIn

📚 RESOURCES MENTIONED:

• "Shine: How Looking Inward is the Key to Unlocking True Entrepreneurial Freedom" by Rob Dube and Gino Wickman
• "Do Nothing" by Rob Dube
• The 10 Disciplines Program
• True Self Assessment
• Small Giants Community

🎧 LISTEN ON: iTunes, Spotify

Bridging the Gap: Employee Ownership and Purpose-Driven Leadership

In this episode of The Freedom Experience, I sit down with Eric Rieger, Founder and CEO of WEBIT Services, to discuss his inspiring journey from making t-shirts to building a purpose-driven, employee-owned tech business. Eric opens up about the challenges of entrepreneurship, the lessons learned from early failures, and his commitment to addressing systemic issues like income inequality through innovative business practices.

Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

1. The Entrepreneurial Journey:

   Eric reflects on his unconventional path to becoming a business owner, starting with his father’s bold advice to "use your credit card and go for it." He shares how resilience, resourcefulness, and a people-first approach helped him navigate early struggles and create lasting success.

2. Employee Ownership and Income Inequality:

   Discover how Eric’s decision to transition WEBIT Services to employee ownership aligns with his mission to tackle income inequality. He dives into the challenges of implementing an ESOP, why purpose-driven leadership is essential, and how businesses can balance profit with social impact.

3. The Importance of Visionary Leadership:

   Eric explains the delicate balance between having big dreams and building systems that align your team around them. He shares how frameworks like EOS and open-book finance have helped him focus his visionary style while empowering his team to thrive.

4. Mental Health and Self-Awareness:

   Vulnerability is strength. Eric shares his personal journey of transformation, including the importance of therapy in addressing trauma, maintaining self-awareness, and building a sustainable leadership style.

Quotes from the Episode:

• “Freedom is being your authentic self and having the resources to take care of your basic needs. Once you have that, you can pursue love, belonging, and purpose.”

• “Private equity is about making money make more money. Employee ownership is about helping people.”

• “If you don’t know your values, someone will buy them. And that’s not a price I’m willing to pay.”

Links & Resources Mentioned:

• Learn more about WEBIT Services: webitservices.com

• Book recommendation: The Great Game of Business by Jack Stack

• Learn about the Entrepreneurial Operating System (EOS): eosworldwide.com

• More on Employee Ownership: nceo.org

Actionable Takeaways:

• Reflect on your personal values and how they align with your business.

• Explore frameworks like Metronomics, EOS, or Great Game of Business to enhance team alignment and transparency.

• If you're a business owner or leader, consider how therapy or coaching can support your personal and professional growth.

How Evergreen Companies Leave a Lasting Imprint

n this episode of The Freedom Experience, I sit down with Bo Burlingham, celebrated author of Small Giants, The Great Game of Business, and Finish Big, to discuss what it really takes to build a business that lasts. Bo has spent decades observing and writing about businesses that prioritize greatness over growth. In our conversation, we explore the principles of Evergreen companies, the importance of mojo, and why businesses with a clear purpose stand the test of time.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

🔹 The Principles of Evergreen Companies
Bo breaks down the seven core principles that define Evergreen companies—from Purpose to Perseverance—and explains why these timeless qualities contribute to long-term success.

🔹 Mojo: The Magnetic Force of Great Businesses
Discover the concept of mojo and how it creates a magnetic pull that draws in employees, customers, and partners who genuinely care about the business.

🔹 The Purpose Behind Profit
Why great companies view profit as a byproduct of serving their customers exceptionally well, rather than the ultimate goal.

🔹 Long-Term Thinking in a Short-Term World
Bo shares why Evergreen businesses adopt a long-term perspective, resisting the pressures of short-term gains and focusing instead on enduring impact.

🔹 Ownership Structures That Build Legacy
We explore how family-owned and employee-owned businesses preserve their core values across generations, ensuring that the company's legacy lives on.

Quotes from the Episode:

💬 “Growth for growth's sake isn't the answer. Great companies know what matters most and stick to it.”
💬 “Mojo is like charisma for a business—it makes people want to be part of your story.”
💬 “Evergreen businesses aren’t afraid to go against the grain. They prioritize people and purpose over short-term profits.”

Links & Resources Mentioned: 🌍 Small Giants Community: https://smallgiants.org
📚 Another Way: Building Companies That Last (Book): https://a.co/d/c0kvE4Z
🔗 Connect with Bo Burlingham on LinkedIn: https://www.linkedin.com/in/bo-burlingham

Actionable Takeaways:

✅ Identify the core purpose that drives your business beyond profit.
✅ Evaluate your business through the lens of the seven Evergreen principles.
✅ Foster a sense of ownership and purpose across your team to build long-term resilience.

Why Business Owners Should Rethink Ownership

In this episode of The Freedom Experience, I sit down with John Abrams, founder of South Mountain Company and a pioneer in employee ownership. John transitioned his company into a worker cooperative in the 1980s—long before employee ownership became a mainstream conversation. Now, with his upcoming book, From Founder to Future: A Business Roadmap to Impact, Longevity, and Employee Ownership, he’s on a mission to help more business owners build companies that endure.

We explore what it really takes to transition a business from founder-led to employee-owned, the risks of private equity takeovers, and why sharing ownership creates stronger, more resilient companies.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

🔹 The Shift to Employee Ownership
John shares his journey of converting South Mountain Company into a worker cooperative and the unexpected benefits it brought—not just for employees but for the company’s long-term success.

🔹 Protecting Your Business from Private Equity Takeovers
Many business owners assume selling to private equity is their only option, but John explains how alternative ownership models like ESOPs, worker co-ops, and employee ownership trusts can preserve a company’s mission.

🔹 The Five Transitions to a CommonWealth Company
John introduces the concept of CommonWealth Companies and the five critical transitions—Ownership, Leadership, Mission, Governance, and Impact—that can help a business thrive beyond the founder.

🔹 Aligning Business with a Bigger Purpose
John discusses how business owners can shift their mindset from chasing short-term growth to creating an enduring company that serves employees, customers, and the community.

🔹 The Future of Employee Ownership
With millions of baby boomer business owners retiring, we talk about why employee ownership is gaining traction and how it can reshape the economy by reducing wealth inequality.

Quotes from the Episode:

💬 “The mentality of ‘they’ll have to drag me out of here feet first’ is a path to disaster. These transitions take planning.”
💬 “When employees have a stake in the business, they think and act like owners—and that changes everything.”
💬 “Selling to the wrong buyer can leave founders with fat wallets and broken hearts. Employee ownership offers another way.”

Links & Resources Mentioned:

🌍 John’s Website: https://abramsangell.com
📚 From Founder to Future (Book): https://bit.ly/3C6vyQt
🔗 Connect with John on LinkedIn: https://www.linkedin.com/in/john-abrams-3bb94683/
🌍 Project Equity (Employee Ownership Resource): https://project-equity.org/

Actionable Takeaways:

✅ Start planning your business transition before you're ready to retire—separate ownership transition from leadership transition.
✅ Explore alternative ownership models (worker co-ops, ESOPs, EOTs) to see what best aligns with your values and long-term goals.
✅ Think beyond short-term profit—companies that prioritize purpose and shared ownership tend to thrive in the long run.

Building a Thriving Business by Filtering Decisions Through Purpose

Matt’s journey started in 2004 as a summer intern. Today, he leads an 80-person civil engineering firm ranked among the Top 5 Best Firms to Work For in the nation—not by accident, but through a deliberate approach to leadership, decision-making, and ownership.

We dive into the unique decision-making filter that guides every major move at Choice One, their employee ownership model, and how they’ve built a company that grows for opportunity—not just for the sake of growth. Matt shares how Choice One’s flat structure, intentional hiring, and commitment to culture have created a business that isn’t just successful but one that employees are proud to be part of.

If you’ve ever wondered how to create a thriving business without chasing growth for growth’s sake, this episode is for you.

🎥 Watch this conversation on YouTube. And SUBSCRIBE!

Key Themes:

🔹 Decision-Making That Aligns with Purpose
Matt shares how Choice One runs every major decision through a structured filter—ensuring alignment with their core purpose, vision, and values before taking action.

🔹 The Difference Between Growth for Opportunity vs. Growth for Growth’s Sake
Matt explains why blindly chasing revenue targets is a trap, and how Choice One has built a strategy around opportunity-driven growth instead.

🔹 An Ownership Model That Engages Employees
Instead of a traditional ESOP, Choice One developed a custom ownership structure that gives employees a real stake in the company—without diluting leadership clarity.

🔹 Clarity, Culture, and Long-Term Thinking
From monthly all-hands meetings to a 10-year vision, Matt discusses how transparency and intentional strategy drive sustained success.

🔹 Building a Business That Lasts for Generations
Choice One isn’t looking for an exit—it’s building an evergreen company that will outlast its current leadership while staying true to its core values.

Quotes from the Episode:

💬 "We don’t grow just because we feel like we have to. We grow because an opportunity aligns with our purpose."
💬 "Ownership shouldn’t be something you’re handed—it should be something you choose to invest in."
💬 "The best leadership isn’t about pulling people toward your vision, but guiding a group toward a shared vision."
💬 "Success isn’t about revenue goals—it’s about building a business people love working for."

Links & Resources Mentioned:

🌍 Choice One Engineering: https://choiceoneengineering.com/
🔗 Connect with Matt Hoying on LinkedIn: https://www.linkedin.com/in/matthoying/

Actionable Takeaways:

✅ Run decisions through a filter—define your purpose, vision, and values to guide growth.
✅ Be intentional about hiring—culture-fit matters more than speed when building a team.
✅ Design ownership structures that align with your business—don’t assume ESOPs are the only option.
✅ Plan for the long term—think in 10-year cycles, not just quarterly results.
✅ Create a business that serves people—employees, customers, and the community.

🎧 If this episode resonated with you, subscribe, share, and leave a review.

From $30M to $350M: The Growth Formula

In this episode of The Freedom Experience, I sit down with Josh Leatherman, Chief Marketing Officer at Service Express, who has played a pivotal role in scaling the company from $30 million to over $350 million in revenue.

Josh shares how he built a high-performing marketing team, why revenue operations is the "Switzerland" between sales and marketing, and how experimentation, accountability, and specialization drive scalable business growth.

We explore his R&D mindset—"Rip Off & Duplicate", the importance of aligning marketing and sales, and why marketers must be insatiable learners to stay ahead. If you're struggling with marketing ROI or trying to build a predictable revenue engine, this episode is packed with actionable insights to help you.

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

Key Themes

🔹 The Power of "Rip Off & Duplicate" (R&D)
Josh explains why you don’t need to reinvent the wheel — instead, learn from industry leaders, implement what works, and focus on one channel at a time to drive revenue.

🔹 Revenue Operations: The Bridge Between Sales & Marketing – Josh shares why RevOps serves as a neutral, objective team that ensures alignment between sales and marketing, eliminating friction and creating a data-driven system for scaling revenue.

🔹 Accountability at Every Stage of the Funnel - Marketing and sales must own their roles — every lead, every account, and every stage of the funnel should have clear accountability to ensure conversion.

🔹 The Ideal Team Player: Humble, Hungry, Smart – Josh reveals how he builds high-performance teams by hiring curious, adaptable, and driven people who thrive in a fast-moving environment.

🔹 Mastering One Marketing Channel Before Expanding – Instead of spreading your budget thin, get exceptionally good at one channel (SEO, intent marketing, paid search, etc.), optimize it for ROI, then scale.

🔹 Identifying & Hiring Natural Learners - Josh discusses why hiring naturally curious and self-driven marketers leads to long-term success, and shares how he identifies high-potential talent in interviews.

Quotes from the Episode

💬 "Rip off and duplicate—someone else has already figured it out."
💬 "Revenue operations is the Switzerland between sales and marketing."
💬 "Fail fast, learn faster, and scale what works."
💬 "Marketers must be insatiably curious."
💬 "If you don’t know what good looks like, how can you hold others accountable?"

Links & Resources Mentioned

🌍 Service Express Website: https://www.serviceexpress.com
🔗 Connect with Josh on LinkedIn: https://www.linkedin.com/in/joshleatherman

Actionable Takeaways

✅ Adopt an R&D Mindset – Learn from industry leaders instead of reinventing strategies.
✅ Leverage Revenue Operations – Use RevOps to align sales and marketing for predictable growth.
✅ Master One Channel First – Specialize before expanding into multiple marketing platforms.
✅ Encourage Small Experiments – Fail fast, learn fast, and scale proven marketing efforts.
✅ Hire for Curiosity – Seek out marketers who are lifelong learners and adaptable.

🎧 Enjoyed this episode? Subscribe, share, and leave a review to help us bring more top-tier insights to you.

How Vision, Values, and Courage Create Real Leadership

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.

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Key Themes

🔹 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.

Quotes from the Episode

💬 "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."

Links & Resources Mentioned

🔗 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

Actionable Takeaways

✅ 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.

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Why Vulnerability Is a Superpower in Leadership

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.

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Thieves of Purpose: What’s Really Holding You Back

Purpose isn’t a destination — it’s how you show up. And most leaders are looking for it in all the wrong places.

Davin Salvagno is a bestselling author, speaker, and executive coach known for helping leaders reconnect with why they started — and who they’re becoming. He’s the co-founder of The Purpose Summit and author of Thieves of Purpose: Overcoming the 12 Mindsets Robbing You of Your Potential, a powerful guide to identifying what’s stealing your motivation.

In this episode, Davin shares how leaders can rediscover purpose in both life and business — and why reconnecting with your “why” starts with your “who.”

We talk about:
🔹 Why purpose is plural and momentary, not one big life goal
🔹 The difference between purpose and motivation
🔹 Why comparison, envy, and distraction rob us of fulfillment
🔹 How to reframe purpose to match the needs around you
🔹 What CEOs can do to reignite purpose in their teams
🔹 Why doubling down on purpose is the smartest move in a crisis

Whether you’re feeling stuck, scaling your company, or leading through uncertainty, this conversation is a reminder that purpose isn’t something to find — it’s something to live.

Quotes from the Episode:
💬 "Your purpose didn’t disappear. You just lost your why."
💬 "Purpose is who you are. Your why is what gets you moving."
💬 "Comparison invites envy. Gratitude brings you back to joy."
💬 "Ask your people why they chose to work for you — the answers will reignite everything."
💬 "Purpose is simple to pursue, but hard to sustain."

Actionable Takeaways:
✅ Stop chasing job titles — focus on your gifts and the needs around you
✅ Reflect on who inspired you to start (that’s your who)
✅ Replace comparison with gratitude to recover lost motivation
✅ Reconnect your team with why they joined, not just what they do
✅ In a crisis, lead with purpose, not fear

Resources from this episode:
→ Connect with Davin: https://www.linkedin.com/in/salvagno/
→ Get the book Thieves of Purpose: https://www.amazon.com/Thieves-Purpose-Overcoming-Mindsets-Potential/
→ Learn more about The Purpose Summit: https://www.thepurposesummit.com

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Building a Company You Actually Want to Work For

Freedom isn’t just about money — it’s about how you build the place you spend half your life. Most founders miss what true ownership can unlock until they’re already stuck.

Carl Erickson started Atomic Object after a failed startup imploded. He turned it into one of the most admired software consultancies out there by making employees owners from day one. Over twenty years, Carl pushed extreme programming, radical pairing, and direct ownership, building a company designed to last a century.

In this episode, Carl breaks down how Extreme Programming rewired their culture, why he rejected ESOPs for a more direct model, and how “Give a Shit” and “Own It” became more than just slogans — they transformed employees into real owners.

We talk about:
🔹 Why extreme programming transformed more than just software quality
🔹 How pairing goes beyond developers — even Atomic’s co-CEOs are a pair
🔹 The hidden cost of ignoring culture in fast-growing companies
🔹 How Carl created a direct employee ownership plan that builds wealth for non-founders
🔹 Why hiring for cultural fit is essential — and how Atomic avoided “cowboys” and prima donnas
🔹 What it takes to protect a 100-year vision in the face of outside offers
🔹 How freedom after exit means choosing how you spend your days with purpose

Whether you’re building a consultancy, scaling a startup, or planning your own exit, this conversation is a masterclass in creating a culture and ownership structure that outlasts you.

Quotes from the Episode:
💬 "Extreme programming isn’t just coding faster — it’s building trust, quality, and culture."
💬 "Give a shit. Own it. Those are the two most important things we look for in people."
💬 "Companies become reflections of their founders — for better or worse."
💬 "Freedom is flexibility: the ability to do what you care about, without worrying about money."

Actionable Takeaways:
✅ Don’t wait to codify your values — they’re already there in how your team behaves
✅ Consider direct ownership plans if you want employees to truly act like owners
✅ Focus on strategic principles like “Great, Not Big” instead of arbitrary growth targets
✅ Build your company’s culture intentionally — it’s easier than fixing it later
✅ Remember: growth should be a byproduct of excellence, not the goal itself

Resources from this episode:
→ Connect with Carl: https://www.linkedin.com/in/carl-erickson
→ Learn about Atomic Object: https://atomicobject.com
→ Carl’s blog “Great Not Big”: https://greatnotbig.com

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