Stop Stepping in Stupid

PODCAST · business

Stop Stepping in Stupid

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.

  1. 28

    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.

  2. 27

    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.

  3. 26

    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/

  4. 25

    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.

  5. 24

    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

  6. 23

    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

  7. 22

    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

  8. 21

    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/

  9. 20

    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.

  10. 19

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

    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.

  11. 18

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

    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.

  12. 17

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

    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

  13. 16

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

    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.

  14. 15

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

    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.

  15. 14

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

    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.

  16. 13

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

    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.comLinkedIn: https://www.linkedin.com/in/maryanncroce/Facebook: https://www.facebook.com/SmallBizVantageInstagram: https://www.instagram.com/smallbizvantage/Youtube: https://www.youtube.com/@smallbizvantage7426

  17. 12

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

    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.

  18. 11

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

    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

  19. 10

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

    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.

  20. 9

    Finding Opportunity in Unlikely Places with Sandy Weir

    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.

  21. 8

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

    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

  22. 7

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

    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

  23. 6

    Creating Lasting & Measurable Change with Joel Bennett

    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.

  24. 5

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

    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

  25. 4

    Building Two Businesses That Create Memorable Moments with Michael Kaloutas

    In this episode, Michael Kaloutas shares the one book that his brother gave him that changed his mindset and life.Michael shares how he built two successful businesses, Seal A Deck and Rednose Holiday Lights, and the biggest challenges he has faced, and how he overcame them.

  26. 3

    From Cutting Lawns To Leading A Company With A 10 Year Streak Of Growth | Kevin Cassidy

    In this episode, Shawn talks with Kevin Cassidy the founder of Cassidy Paving in Haverhill, MA. Kevin shares how he got into the paving business and his key learnings in creating a growing company.linkedin.com/in/kevin-cassidy-7b83299b cassidypaving.com

  27. 2

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ABOUT THIS 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.

HOSTED BY

Shawn Shepheard

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