Shawn Shepheard

Stop Stepping in Stupid

Business EN ↓ 28 episodes

I’m Shawn Shepheard. I coach and consult family-owned businesses to get them to the next level – without working 24/7.Join me on a podcast journey where we explore the moments someone stepped in stupid. These are real conversations, talking about the voices in our heads, the decisions we really made, and the struggles we all have but don’t hear talked about enough away from the coffee shop or the bar. So we’re bringing conversations like that onto the show, even talking about the stuff outside our businesses which of course influence us in our work. These conversations will help you feel seen...

Author

Shawn Shepheard

Category

Business

Podcast website

shawnshepheard.com

Latest episode

May 15, 2026

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Episodes

You Are a Hero as a Team: Casey Van Sant on Why Winning Alone Isn't Winning 15.05.2026

Casey Van Sant has built his career on taking leaps of faith, from competitive shotgun shooting to running preconstruction at a third-generation family business. In this episode, he gets honest about the trap of trying to do it all yourself, why admitting you need help is actually a power move, and how Hutcherson Construction went from $8M to nearly $30M without losing what made them great. If you...

Every Choice Has an Invoice: Daryl Avery Williams on Building a Marketing Agency With Grit and Zero Debt 13.05.2026

Daryl Avery Williams bootstrapped every dollar, never rolled a credit card bill, and grew from zero to 18 team members without taking on a single loan. In this episode she shares what it really looks like to build a marketing agency from scratch in the construction and trades industry and the Busta Rhymes quote that changed how she makes every major decision. If you have ever felt like you were on...

Stop Stepping in Stupid - Audiobook 20.04.2026

You've built a successful business but now you're stuck. The days are getting longer, not shorter. You're working harder but seeing fewer results. Most business advice isn't designed for family-owned businesses like yours. Performance coach Shawn Shepheard shares lessons from twenty-six years of working with business owners across North America. Through real stories and proven frameworks, you'll d...

Reid Hutcherson: Integrity Over Profit in a Third-Generation Construction Company 02.12.2025

What happens when you put integrity over profit? Reid Hutcherson of Hutcherson Construction explains how his grandfather's values still guide the company today, why they treat subcontractors as partners (not vendors), and how being fair to everyone—even when it costs more—has built a 45-year reputation that keeps clients coming back. https://www.hutchersonconstruction.com/

That's So High School with Dr. Julie Gowthorpe: Dealing with Disruptive Personalities at Work 16.10.2025

Is there one person in your company that everyone knows their name - including your family at home? Dr. Julie Gowthorpe joins Shawn to discuss the real cost of tolerating disruptive personalities and why avoiding these challenging conversations is costing you more than you think. Learn the practical tools to address toxic behavior before it destroys your team culture.

Stop Stepping in Stupid: Suvi Gets the Inside Story on Shawn's Game-Changing Pocketbook 08.08.2025

Video producer Suvi Siu sits down with Shawn Shepheard to get the real story behind his new book "Stop Stepping in Stupid." Shawn reveals why he made it small enough to literally fit in your jeans and shares stories of family business owners who transformed their lives using these strategies. This interview covers everything from the "beer test" for coaches to why doing less actually grows your bu...

Meaningful Partnerships in Business with Charlie Durham 17.06.2025

Charlie Durham from McSweeney Painting shares how he transformed from a paint salesman to a business leader by embracing the power of genuine partnerships. In this conversation, Charlie reveals why he calls clients "partners" instead of customers and how building meaningful relationships has become the foundation of their business success. 🔗 Linkedin 🔗 mcsweeneycommercial.com

Playing Full Out: How Lester McLean Built Two Dream Careers 20.02.2025

Meet Lester McLean, who spent 28 years at TSN while building a successful music career at night. Learn how this hockey-playing musician turned his Christmas cards into songs, his passion into performances, and his dreams into reality by having the courage to take action before feeling ready. https://lestermclean.com/ https://www.instagram.com/lestermcleanmusic/ https://www.youtube.com/@lomclean ht...

Building Bridges: Jay Culbert on Community, Collaboration, and Career Paths 30.01.2025

In this enlightening episode of Stop Stepping in Stupid, Shawn dives deep with Jay Culbert, exploring his early influences, the pivotal career choices he made, and the birth of Facility Rockstars . Discover how Jay leverages community and collaboration to enhance the world of facility management. https://www.kaloutas.com/ https://www.linkedin.com/in/jay-culbert-2675998/

From Loafers to Leadership: Dan D'Ambrosio’s Journey at Cassidy Paving 09.01.2025

In this revealing episode, Dan D'Ambrosio shares his unexpected journey into the paving industry and the lessons learned from taking on projects that tested the limits of Cassidy Paving’s expertise. Learn how they refined their project selection to enhance profitability and client satisfaction.

The Path Less Taken: Lessons from Restauranteur and Author Nicole Ponseca 14.11.2024

Nicole Ponseca left San Diego for New York with just $75 and no set plan. In this episode, she shares her remarkable journey, from working odd jobs to launching two groundbreaking Filipino restaurants, all while redefining what it means to bet on yourself in the face of the unknown.

Embracing the Challenges: How Jillian Burns Turned Adversity into a New Business 31.10.2024

Jillian Burns shares her inspiring journey of overcoming financial betrayal, rebuilding her business, and launching Influential Encounters—a community for women in male-dominated industries. Hear how she turned adversity into an opportunity for growth and empowerment.

Unlocking Growth: 6 Strategies from Shawn's New Book "Stop Stepping in Stupid" 17.10.2024

Get an exclusive look into Shawn Shepheard's upcoming book, Stop Stepping in Stupid. In this episode, Shawn shares six powerful strategies to start doing that will help you grow your business and reclaim your time. shawnshepheard.com

Stop Stepping in Stupid: 5 Must-Read Chapters from Shawn's New Book 03.10.2024

In this special episode, Shawn gives a sneak peek into his upcoming book Stop Stepping in Stupid, sharing five key things you should stop doing immediately to grow your business. Learn how these lessons can take your business to the next level.

The Power of Values in Business: A Conversation with Glenn Keeping 19.09.2024

In this episode, Shawn sits down with Glenn Keeping, a seasoned pharmacist turned leadership coach. They discuss the importance of aligning your work with your values, overcoming burnout, and the transformative power of coaching for professionals feeling stuck in their careers.

Keeping Cool Under Pressure: Greg Kimmerly’s Referee Lessons for Business Leaders 05.09.2024

What does it take to thrive when every move is under the microscope? Former NHL referee Greg Kimmerly shares his experiences from the ice and how they translate into coaching small business leaders today.

Three-Day Weekends: Balancing Entrepreneurship and Life with Maryann Croce 18.07.2024

Join Shawn as he dives into a heartfelt conversation with Maryann Croce, a seasoned entrepreneur in the automotive industry. They explore her journey from childhood influences to founding a successful family business, offering insights into overcoming challenges and finding balance in work and life. Website: SmallBizVantage.com LinkedIn: https://www.linkedin.com/in/maryanncroce/ Facebook:  https:/...

The Walk-On Mindset: Lessons from UConn Basketball to Business Success with Vaughn Butler 04.07.2024

Vaughn Butler, Founder of Scholar Painting LLC, shares his journey from a small Connecticut town to running a multi-state restoration company. Discover how his UConn basketball walk-on experience shaped his business philosophy and approach to challenges.

From Humble Beginnings to 500% Growth with Patrick Coburn Jr. 20.06.2024

Join us as Patrick Coburn Jr. shares his journey from a working-class upbringing to leading a thriving family business. Patrick discusses the importance of communication, making tough decisions, and the value of focusing on personal and professional growth. amconcorp.com

From Sports to Business: Path to Effective Leadership with Mark Bloodworth 06.06.2024

In this episode of "Stop Stepping in Stupid," Shawn interviews Mark Bloodworth, the mind behind Lifeblood Performance. Mark shares his journey from sports to founding Lifeblood Performance, emphasizing the importance of asking more and telling less. Tune in to learn practical strategies for transforming teams and leading with authenticity.

Finding Opportunity in Unlikely Places with Sandy Weir 23.05.2024

In this episode, Sandy Weir recounts how she used her MBA skills to start Smooth Wax Bar, despite knowing nothing about the beauty industry. This episode provides valuable lessons on resilience, trust, and continuous learning.

Building Blocks of Leadership: Lessons from the Construction Industry with Michael Maloney 09.05.2024

In this episode, Shawn talks with Michael Maloney, Apprenticeship Director at Gould Construction Institute. They discuss Michael's journey from working in various industries to his current role in training the next generation of construction professionals.  Tune in for an engaging discussion on career paths, entrepreneurship, and the value of lifelong learning. Website: www.gwgci.org

Always Make Your Future Bigger Than Your Past - The Power of Life Long Learning with Shawn Shepheard 25.04.2024

In this episode, Shawn shares his journey of lifetime of learning and adapting. Find out what he considered to be the best business school for him and much more. shawnshepheard.com

Creating Lasting & Measurable Change with Joel Bennett 11.04.2024

In this episode Shawn talks with Joel Bennett founder of Veel Hoeden Consulting in Pella, Iowa. Joel has a long track record of working with blue-collar businesses to help them create lasting change that matters.

From Delivering Newspapers On Rollerskates To Becoming A CEO with Kayla Nassar 28.03.2024

In this episode Shawn talks with the CEO of AmConCorp in Peabody MA. Kayla shares her story of working in the family business and some of the challenges her and her brother have faced along the way. To learn more about Kayla please follow her on LinkedIn ( linkedin.com/in/kayla-nassar-71b460107 ) and visit the company site at www.amconcorp.com

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