Business Owner Tales from the Trenches

Hosted by Cannon Carr

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Apr 2026

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Join Cannon Carr, former business owner and Partner at EP Wealth Advisors, as he has conversations with entrepreneurs on lessons learned from the trenches. Cannon and his guests talk about sustaining business success, while appreciating financial independence along the way. Do you want to learn more about the 3Rs, a wealth strategy for entrepreneurs? Visit cannon-carr.com to find more information as well as resources to help you on your entrepreneurial journey.

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April 10, 2026Episode 4127 min

The Balance Every Owner Faces: Performance, Culture, and Wealth with Caroline Wilbert

Caroline shares her path from 10 years as a business reporter to co-founding The Wilbert Group with her then-husband, then buying him out after their divorce and becoming the day-to-day leader. She explains how the agency expanded from traditional media relations into digital storytelling across LinkedIn, Instagram, podcasts, blogs, websites, and influencers, creating a dedicated digital team. Caroline describes balancing a hard-driving culture with wellness and grace, defining success as great client work, team growth, and long-term profitability. She discusses building financial discipline with advisors, using profit sharing to build wealth, developing homegrown leadership, and now focusing on key clients, new business, family time, and writing. 00:00 Introduction 00:26 Meet Caroline Wilbert 02:01 From Journalist to Founder 02:54 Buying Out and Leading 05:17 PR Industry Shifts 06:51 Building a Digital Team 08:30 Adapting to AI Waves 09:23 Values and Culture 12:23 Choosing the Right Clients 13:48 Finding a Client Voice 16:08 Defining Success Metrics 18:19 Profitability and Wealth 20:16 Financial Advisors and Systems 22:08 Homegrown Leadership Team 24:01 Founder Advice and Discipline 25:57 Next Chapter Ahead FOR MORE INFORMATION: 📱 Contact Me: ⁠https://cannon-carr.com/contact⁠ 📕 My 3Rs Framework: ⁠https://cannon-carr.com/the-3rs/ ⁠ 🌐 Website: ⁠https://cannon-carr.com/⁠ 🛠️ Resources: ⁠https://cannon-carr.com/resources/⁠ 🎙️ Podcast: ⁠https://cannon-carr.com/episodes/ ⁠ FOLLOW US ON SOCIAL: LinkedIn: ⁠ / cannon-carr ⁠Facebook: ⁠ / epwealthadvisors ⁠ YouTube: @cannon-carr EP WEALTH ADVISORS: EP Wealth Advisors, LLC ("EP Wealth") is a leading independent registered investment adviser ("RIA") on a mission to provide clients with honest and objective advice through personalized financial planning, customized investment portfolios, and integrated tax and estate planning. Visit epwealth.com to find out more. 🎙️ Podcast Production by Spoken Podcasts: ⁠⁠https://spokenpodcasts.com⁠

March 5, 202638 min

Listening to the Market: Bryan Clayton's Path from Start-Up to Scale

Brian recounts starting a lawn-mowing business in high school, learning leadership through hiring and realizing he was ultimately in the sales business, then scaling to about $10M in revenue, 150 employees, and selling the company after two years of preparing it for acquisition. After a brief, unfulfilling attempt at retirement, he founded GreenPal, a DoorDash-like platform for lawn care, naively expecting it to be easy and spending two years learning to code and run a tech business. He explains bootstrapping with about $150,000 among co-founders, keeping personal burn low, reinvesting early revenue into developer hours, and avoiding outside funding to stay customer-focused. Growth was slow in one city until product issues were fixed ("nail it, then scale it"), eventually expanding nationwide to about 300,000 users, while emphasizing feedback-driven leadership, celebrating small wins, obsession with details, and dedicating weekly time to personal development. 00:00 Welcome and Brian's Story 00:17 From Mower to Sales Engine 02:17 Getting Out of the Truck 03:42 Deciding to Sell the Business 05:03 Starting GreenPal After Exit 07:39 Finding Mentors on YouTube 11:04 Personal Burn Rate and Risk 14:22 Bootstrapping and Customer-Driven Builds 16:40 Nail It Then Scale It 20:39 Leadership and Culture as You Grow 25:30 Delegation and Feedback Loops 27:00 Stubbornness Grit and Small Wins 31:11 Obsession vs Flexibility 34:32 Work on Yourself and Closing For More Information: 📱 Contact Me: ⁠https://cannon-carr.com/contact/⁠ 📕 My 3Rs Framework: ⁠https://cannon-carr.com/the-3rs/⁠ 🌐 Website: ⁠https://cannon-carr.com/⁠ 🛠️ Resources: ⁠https://cannon-carr.com/resources/⁠ 🎙️ Podcast: ⁠https://cannon-carr.com/episodes/⁠ ---------------------------------- FOLLOW ON SOCIAL LinkedIn: ⁠ / cannon-carr ⁠Facebook: ⁠ / epwealthadvisors ⁠ YouTube: @cannon-carr ---------------------------------- EP WEALTH ADVISORS EP Wealth Advisors, LLC ("EP Wealth") is a leading independent registered investment adviser ("RIA") on a mission to provide clients with honest and objective advice through personalized financial planning, customized investment portfolios, and integrated tax and estate planning. Visit epwealth.com to find out more.

January 20, 202641 min

Beyond Revenue: The Entrepreneur's Journey to Freedom and Purpose

Cannon Carr hosts an inspiring conversation with Shaun Enders, CEO of Transition Staffing Group— a firm specializing in finance, accounting, and tech roles. Shaun delves into his twenty-year journey from corporate recruiting to creating his own recruiting firm rooted in mentorship and growth. More than just business metrics, Shaun emphasizes the importance of personal fulfillment, clarity of purpose, and financial independence. Highlighting his 'Freedom Fund' mindset, Shaun talks about his personal experiences, including the impactful lessons learned from his grandparents' financial struggles and his intentional move towards entrepreneurship. The discussion also covers Shaun's strategies for scaling his business, letting go to let others grow, and his philanthropic efforts, such as the Enders Foundation scholarship fund. Packed with valuable insights on creating a purposeful business while ensuring personal financial security, this episode is a must-listen for aspiring and seasoned entrepreneurs alike. 00:00 Introduction and Welcome 00:28 Meet Sean Enders: CEO and Mentor 01:51 Sean's Entrepreneurial Journey 06:08 Lessons from Family: Financial Planning 10:16 Defining Success and Financial Independence 14:59 The Freedom Fund Concept 17:19 Balancing Business and Personal Wealth 22:24 Riding Out Financial Storms 23:38 The Fluidity of Financial Planning 25:27 Advice for Aspiring Entrepreneurs 26:12 Scaling a Service Business 29:27 Delegation and Growth 31:07 Future Vision for Transition Staffing Group 33:45 Final Thoughts and Contact Information 35:46 Reflections and Key Takeaways Resources Mentioned My 3Rs Framework for business owners: ⁠https://cannon-carr.com/the-3rs/⁠ Website: ⁠https://cannon-carr.com/⁠ Tools & resources for entrepreneurs: ⁠https://cannon-carr.com/resources/⁠ More episodes of Business Owner Tales from the Trenches: ⁠https://cannon-carr.com/episodes/⁠ If you're a business owner who wants to build a company that creates impact and long-term wealth, hit Subscribe, give this video a like, and share it with another entrepreneur who loves coffee and purpose-driven business. When you're ready to take the next step, download the 3Rs Framework and start applying these ideas to your own business today. Resources 📕 My 3Rs Framework: ⁠https://cannon-carr.com/the-3rs/⁠⁠ ⁠ 🌐 Website: ⁠https://cannon-carr.com/⁠⁠ ⁠ 🛠️ Resources: ⁠https://cannon-carr.com/resources/⁠⁠ ⁠ 🎙️ Podcast: ⁠https://cannon-carr.com/episodes/⁠⁠ ⁠ ---------------------------------- FOLLOW ON SOCIAL LinkedIn: / cannon-carr Facebook: / epwealthadvisors YouTube: @cannon-carr ---------------------------------- EP WEALTH ADVISORS EP Wealth Advisors, LLC ("EP Wealth") is a leading independent registered investment adviser ("RIA") on a mission to provide clients with honest and objective advice through personalized financial planning, customized investment portfolios, and integrated tax and estate planning. Visit epwealth.com to find out more.

December 16, 202550 min

Thrive Through Service: Randy Hain's Approach to Leadership and Coaching

Unlocking Leadership Success: A Conversation with Randy About Coaching and Building Effective Teams In this episode, Randy joins the show to discuss his extensive experience in leadership and team development. After a 25-year career in corporate America, including senior executive roles and co-owning a national executive search firm, Randy transitioned to entrepreneurship. He founded Serium Partners and The Leadership Foundry to focus on executive coaching and leadership development for Fortune 5000 companies and global teams. Randy shares his journey, emphasizing the importance of defining personal and professional success, building trust with team members, and leading with generosity. He discusses how he balances giving away intellectual capital while maintaining business profitability, integrating personal lives with professional goals, and the power of candid conversations and feedback in fostering a healthy work culture. Tune in to learn actionable insights on sustaining long-term leadership success and keeping teams motivated. 00:00 Introduction and Welcome 00:09 Randy's Journey from Corporate to Coaching 01:25 Starting the Coaching Business 03:10 Validating the Coaching Business Idea 04:03 Defining Success in Leadership 04:44 The Importance of Listening and Curiosity 05:37 Overcoming Obstacles to Success 06:26 The Role of Discomfort in Growth 06:51 Using Assessments and Feedback 08:31 The Integrated Approach to Coaching 09:59 Balancing Personal and Professional Life 11:40 The Power of a Clear Mission Statement 18:32 Building Trust and Relationships in Teams 21:18 Maintaining a Healthy Culture with Candor 22:35 Constructive Feedback Techniques 23:16 Encouraging Candor in Leadership 25:06 Short-Term vs. Long-Term Leadership Strategies 27:02 The Importance of Coaching-Oriented Leadership 28:01 Effective One-on-One Check-Ins 32:21 Onboarding and Building Relationships 33:57 The Power of Generosity in Business 40:42 Conclusion and Ways to Connect Resources Mentioned My 3Rs Framework for business owners: https://cannon-carr.com/the-3rs/ Website: https://cannon-carr.com/ Tools & resources for entrepreneurs: https://cannon-carr.com/resources/ More episodes of Business Owner Tales from the Trenches: https://cannon-carr.com/episodes/ If you're a business owner who wants to build a company that creates impact and long-term wealth, hit Subscribe, give this video a like, and share it with another entrepreneur who loves coffee and purpose-driven business. When you're ready to take the next step, download the 3Rs Framework and start applying these ideas to your own business today. Resources 📕 My 3Rs Framework: https://cannon-carr.com/the-3rs/ 🌐 Website: https://cannon-carr.com/ 🛠️ Resources: https://cannon-carr.com/resources/ 🎙️ Podcast: https://cannon-carr.com/episodes/ ---------------------------------- FOLLOW ON SOCIAL LinkedIn: / cannon-carr Facebook: / epwealthadvisors YouTube: @cannon-carr ---------------------------------- EP WEALTH ADVISORS EP Wealth Advisors, LLC ("EP Wealth") is a leading independent registered investment adviser ("RIA") on a mission to provide clients with honest and objective advice through personalized financial planning, customized investment portfolios, and integrated tax and estate planning. Visit epwealth.com to find out more.

November 18, 2025Episode 3937 min

Blending Profit and Purpose: A Coffee Entrepreneur's Tale

In this episode, David Paparelli discusses his entrepreneurial journey, focusing on the founding and growth of his coffee business, M-Cultivo. From his early inclination toward entrepreneurship, through various mentorships, to his unique approach to starting and scaling his company, David shares valuable insights. He explains how he identified a gap in the specialty coffee sector and used a mix of technology and customer engagement to fill it. David talks about the challenges of bootstrapping a tech-driven business, the importance of staying close to the customer, and how to balance purpose with profitability. He also delves into his funding strategies, his vision for scaling the business, and his long-term goals, emphasizing the impact-driven mission at the heart of his company. 00:00 Introduction and Early Entrepreneurial Spirit 01:25 Mentors and Early Career Influences 02:30 Founding M-Cultivo: Inspiration and Initial Steps 05:42 Navigating Challenges and Building the Business 13:55 Funding and Financial Strategies 17:50 The Psychology of Bootstrapping 18:06 Plans to Scale the Business 20:36 Building a Strong Leadership Team 21:27 Balancing Equity and Debt 25:17 Monetizing the Business 29:55 Advice for Budding Entrepreneurs 33:25 Final Thoughts and Contact Information Resources 📕 My 3Rs Framework: https://cannon-carr.com/the-3rs/ 🌐 Website: https://cannon-carr.com/ 🛠️ Resources: https://cannon-carr.com/resources/ 🎙️ Podcast: https://cannon-carr.com/episodes/ ---------------------------------- FOLLOW ON SOCIAL LinkedIn: / cannon-carr Facebook: / epwealthadvisors YouTube: @cannon-carr ---------------------------------- EP WEALTH ADVISORS EP Wealth Advisors, LLC ("EP Wealth") is a leading independent registered investment adviser ("RIA") on a mission to provide clients with honest and objective advice through personalized financial planning, customized investment portfolios, and integrated tax and estate planning. Visit epwealth.com to find out more.

October 21, 202527 min

The 95% Rule: Building a Culture of Accountability with Todd Stanton

💡 Episode Summary What if 5% of your employees are creating 95% of your problems? This week, Cannon and Claudia sit down with Todd Stanton, founder of Stanton Law and author of The 95% Rule: 29 Employment Law Axioms for Owners, Execs, and HR. While the title suggests employment law, this conversation goes much deeper — into the heart of leadership, ownership, and building a culture of accountability. Todd explains how a victim mentality in both leaders and employees erodes company health — and how reclaiming agency and responsibility leads to a high-performing, self-led team. He discusses the mindset shift from lawyer to entrepreneur, why "failure to fire" is leadership malpractice, and how running a law firm like a business can set a model for every professional service leader. 🔑 Key Takeaways 5% cause 95% of your problems. Recognize and address the small percentage of employees that drain time and culture. Ownership starts at the top. If problems persist, management allowed them to exist. Run your firm like a business. Lawyers — and all service professionals — thrive when they embrace leadership and accountability. Clarity saves time. The 29 axioms in Todd's book serve as heuristics for better, faster decision-making. Victim mentality kills progress. Both leaders and employees must reject entitlement and embrace agency. Build a business that outlives you. True success is creating sustainable and fulfilling lives for both employees and clients. Engage legal counsel early. Don't wait until a crisis to involve your attorney — use them proactively as a strategic partner. Leadership is letting go. The founder's job is to empower, not control; to make themselves increasingly unnecessary. 👤 Guest Bio Todd Stanton is the founder and principal of Stanton Law LLC, a forward-thinking employment law firm based in Atlanta. With 17 attorneys and a mission to create sustainable and fulfilling professional lives, Todd has built a firm that operates like a business, not a bureaucracy. He's also the bestselling author of The 95% Rule: 29 Employment Law Axioms for Owners, Execs, and HR, a practical and insightful guide for leaders who want to cultivate high-performing teams and avoid costly HR mistakes. 📘 Learn more at stantonlawllc.com Resources 📕 My 3Rs Framework: https://cannon-carr.com/the-3rs/ 🌐 Website: https://cannon-carr.com/ 🛠️ Resources: https://cannon-carr.com/resources/ 🎙️ Podcast: https://cannon-carr.com/episodes/ ---------------------------------- FOLLOW ON SOCIAL LinkedIn: / cannon-carr Facebook: / epwealthadvisors YouTube: @cannon-carr ---------------------------------- EP WEALTH ADVISORS EP Wealth Advisors, LLC ("EP Wealth") is a leading independent registered investment adviser ("RIA") on a mission to provide clients with honest and objective advice through personalized financial planning, customized investment portfolios, and integrated tax and estate planning. Visit epwealth.com to find out more.

October 1, 2025Episode 3727 min

Reflections on a Successful Business Sale: Insights from Cannon

What does it really take to sell a business without regret? In this anniversary conversation, Cannon Carr shares his experience of leading his firm through a major transition—what went as expected, what surprises hit hardest, and how preparation years in advance made all the difference. From the importance of clean books and solid processes, to setting non-negotiables, to navigating the emotional toll of the deal, Cannon gives a candid look behind the curtain of mergers and acquisitions. He also unpacks his Three R's Framework—Reward, Reinvest, and Repurpose—and why values are just as important as valuation. Whether you're a business owner considering your own exit or simply curious about how big deals come together, this episode delivers insight, vulnerability, and practical takeaways you won't hear anywhere else. What You'll Learn in This Episode: Why two-thirds of business sales end in regret—and how to avoid that outcome. The foundational work every owner should do 2–3 years before a sale. The role of non-negotiables in deal negotiations. The emotional toll of selling—and how to stay grounded through it. Why shared values with a buyer are just as important as valuation. The importance of diversified wealth before a transaction. How Cannon's Three R's framework shaped his decisions. The personal and family impact of going through a business sale. How Vistage peer groups, EOS, and trusted advisors played into the process. Final advice Cannon gives to business owners considering a future exit. Resources & Links Mentioned: Cannon Carr's website & resources: cannon-carr.com EP Wealth Advisors: epwealth.com Vistage: vistage.com

September 2, 2025Episode 3333 min

The Power of Clarity and Health in Entrepreneurship

In this episode, hosts Cannon and Claudia discuss the importance of health as a competitive advantage for business owners with guest Justin Roethingshofer, founder of Own It Coaching. Justin shares his transformation journey, driven by his experiences in the NHL and his personal health challenges. He offers insights into his high-performance health consultancy, which focuses on individualized health optimization for business leaders. Listeners are encouraged to consider key questions about their purpose, energy use, and risk management to ensure peak performance in their business endeavors. The conversation also explores the challenges of entrepreneurship, the value of clarity and process, and the importance of maintaining health to drive sustained business success. 00:00 Introduction: Health as a Competitive Advantage 00:35 Meet Justin Roethingshofer: Founder of Own Eight Coaching 02:20 Justin's Journey: From NHL to Health Consultancy 07:07 The Philosophy Behind Own Eight Coaching 13:41 Building the Business: Challenges and Breakthroughs 17:27 The Turning Point: Divine Intervention and the Own IT Manifesto 22:41 First Steps: Hiring and Scaling the Business 24:47 Delegating to Focus on Passion 26:05 Learning from Mistakes and Focusing on Client Experience 27:12 The Importance of Marketing and Personal Sacrifices 27:55 Celebrating Milestones and Telling Client Stories 28:51 Funding the Startup and Reinvesting Profits 29:31 Commitment to Excellence and Client Experience 31:45 Future Vision and Expanding Health Houses 34:28 Personalized Health and Preventative Care 36:29 The Concept of Age and Biological Health 38:27 Final Thoughts and Contact Information 39:11 Studio Wrap-Up and Key Takeaways

June 19, 2025Episode 3231 min

Growing 10X: Building a Business That Feels Small at Scale

How do you grow a business 10X—without losing the personal touch that made it special in the first place? In this episode of Business Owner Tales from the Trenches, EP Wealth Co-Founder Brian Parker unpacks the art of scaling with intention. Brian shares the real-life challenges of growing a boutique firm into a national powerhouse—while preserving the human element, internal culture, and client intimacy. Whether you're a startup founder, seasoned executive, or aspiring entrepreneur, this is a masterclass in leadership, growth strategy, and sustainable scaling. ➡️ Learn how to: Build systems without creating bureaucracy Retain your team's "small company" mindset Scale services while staying client-focused Navigate rapid growth without breaking your brand Tune in for actionable insight, candid stories, and lessons from the trenches of 10X growth. https://www.cannon-carr.com

July 23, 202450 min

Ep 32: Navigating Transitions and Why Your Story Matters with Michelle Prince

Changing careers can be a scary and often necessary move as your needs, interests, goals, and skills transform over time. In this episode, you're going to hear about how you can succeed as an entrepreneur in your SECOND career. You will also hear about how to differentiate yourself from other people while building trust at the same time. You can find show notes, resources and more at: https://bit.ly/3VZclq6