Avoiding Entitlement and Fostering Growth: Jim Sheils’ Blueprint for Entrepreneurial Families

May 21, 2025

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How would you approach building generosity and responsibility in a family with new wealth?

We welcome Jim Sheils.

Jim is the co-owner of Southern Impression Homes, founder of 18 Summers, and author of the Wall Street Journal bestseller “The Family Board Meeting.” He’s made it his life’s mission to help entrepreneurs blend their passion for business with a thriving, intentional family life.

Drawing from personal experience—like lending a kidney to his own father and designing a curriculum for his children—Jim offers candid insights into creating lasting connections at home, even while building success at work.

In this episode, Jim shares how his entrepreneurial spirit emerged early, why traditional education left him questioning the system, and how the wisdom of his grandfathers shaped his approach to business and life. He opens up about the challenges of generational wealth, raising grounded and grateful kids, and his practical strategies for maximizing those precious “18 summers” with your children.

If you’re an entrepreneur searching for more than just business success—and want to ensure your family thrives alongside your ventures—this conversation is a must-listen. Tune in for inspiration, actionable advice, and Jim’s timeless reminder: true wealth is measured in moments, not just money.

Empowering Moments

04:33 Purpose of Traditional Schooling?

08:10 Higher Education: Is It Necessary?

11:55 "Personal Development Awakening"

16:06 "Persistence in Challenging Conditions"

17:01 "Early Lessons in Overcoming Rejection"

22:39 College Majors: Choose Wisely

24:34 Balancing Family and Business

28:14 Building Generational Wealth Solutions

32:48 Entrepreneurial Guilt and Family Dynamics

33:48 Entrepreneurship vs. Family: A Dilemma

39:31 Parental Challenges: Entrepreneur's Burden

40:13 "Teens: Support Your Parents?"

46:01 "A Positive Haunting: Real Estate"

47:49 Busy Parent's Life Reflections

51:19 "Expanding Influence While Staying Balanced"

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Here are 3 key takeaways from our conversation with Jim:

Questioning the Status Quo Can Spark Innovation: Jim was an “entrepreneur against the grain” from a young age, always asking why—and that curiosity eventually led him to build creative businesses and challenge traditional education for his own kids.
Family Board Meetings Matter: Jim’s “18 Summers” concept is a wake-up call—a reminder that 85% of quality time with our children happens before they turn 18. He shares practical strategies for entrepreneurs to intentionally create rhythms and boundaries, ensuring that family isn’t sidelined by business.
Wealth is More Than Finances: Jim emphasizes having “the money talk” with your kids by their mid-teens, setting clear values and limits to prevent entitlement and empower responsible future generations. His transparent approach to family wealth and legacy is something every entrepreneur can benefit from.

Running a business doesn’t have to run your life.

Without a business partner who holds you accountable, it’s easy to be so busy ‘doing’ business that you don’t have the right strategy to grow your business.

Stop letting your business run you. At Harper & Co CPA Plus, we know that you want to be empowered to build the lifestyle you envision. In order to do that you need a clear path to follow for success

Our clients enjoy a proactive partnership with us. Schedule a consultation with us today.

Download our free guide - Entrepreneurial Success Formula: How to Avoid Managing Your Business From Your Bank Account.

Glenn Harper, CPA, is the Owner and Managing Partner of Harper & Company CPAs Plus, a top 10 Managing Partner in the country (Accounting Today's 2022 MP Elite). His firm won the 2021 Luca Award for Firm of the Year.

An entrepreneur and speaker, Glenn transformed his firm into an advisory-focused practice, doubling revenue and profit in two years. He teaches entrepreneurs to build financial and operational excellence, speaks nationwide to CPA firm owners about running their businesses like entrepreneurs, and consults with firms across the country. Glenn enjoys golfing, fishing, hiking, cooking, and spending time with his family.

Julie Smith, MBA, is a serial entrepreneur in the public accounting space. She is the Founder of EmpowerCPA™, Founder of PureTax, LLC, COO for Harper & Company CPAs Plus, and Co-host of the Empowering Entrepreneurs podcast.

Named CPA.com's 2021 Innovative Practitioner of Year, Julie led Harper & Company's transition to an advisory-focused firm, doubling revenue and profit in two years. She now empowers other CPA firm owners nationwide through consulting and speaking, teaching them how to run their businesses like entrepreneurs. Julie lives in Columbus, OH with her family and enjoys travel, coaching basketball, sporting events, and the occasional shopping spree.

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