Stop Stepping in Stupid

Hosted by Shawn Shepheard

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May 2026

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About the show

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 – but also help you think and execute differently. Because what got you here won’t get you to the next level.

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28 recent

May 15, 2026Episode 2837 min

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

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've ever felt like you had to prove yourself by doing everything alone, this one's for you.

May 13, 2026Episode 2739 min

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

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 one foot on the gas and one foot on the brake this one is for you.

April 20, 2026Episode 261 hr 14 min

Stop Stepping in Stupid - Audiobook

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 discover:Why working harder isn't working anymoreHow to eliminate low-value activities that drain your energyThe three things all peak performers do differentlyA simple system for making better decisions under pressureHow to build momentum that creates sustainable growthThis isn't theory-it's transformation. Because you can't afford to keep stepping in stupid.

December 2, 2025Episode 2523 min

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

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/

October 16, 2025Episode 2429 min

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

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.

August 8, 2025Episode 2325 min

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

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 business more.Suvimedia.com

June 17, 2025Episode 2234 min

Meaningful Partnerships in Business with Charlie Durham

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

February 20, 2025Episode 2036 min

Playing Full Out: How Lester McLean Built Two Dream Careers

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/@lomcleanhttps://www.facebook.com/lester.mclean.33

January 30, 2025Episode 1930 min

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

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/

January 9, 2025Episode 1830 min

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

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.