David’s Articles

David has been writing and publishing since 2006.  

This post was written and published prior to September 2023 when David and his prior firm, Family Capital Strategy, merged with Greycourt.  Views expressed reflected David’s personal views at the time and do not necessarily reflect the views of Greycourt.  Posts and information may be out of date and should not be relied upon for investment advice.

5 Questions Wealth Creators Should Consider To Avoid Entitled Kids

Sep 16, 2022 | Family Wealth

Spend any time with a wealth creator and it will not be long before you hear about the next generation.  Almost unanimously, the very real concern expressed is that somehow the new wealth of the family will screw up future generations.  While, I have written about entitlement before (see The Challenge and Complexity of Entitlement), it feels important to consider entitlement specifically from the lens of G1.  

When you ask a G1 (Founder / Entrepreneur or other form of wealth creator) what they are focused on now, it is this dynamic that looms large.   

For many of these wildly successful, masters of the universe, these next gen considerations are driven largely by concern, worry, and dare I say it, fear.  Maybe that is the right response, in the face of an unknown future that can feel nebulous and amorphous, fear may be the correct reaction.  But when we teach our kids to swim, a physical environment not all that dissimilar to the mental one described above, we do not teach them to be afraid of the water, but instead to respect it.  That feels like the correct path here.

So, with that, here are 5 critical questions for G1’s to consider regarding next gens.

First – where in the course of building your business did fear lead you to make the optimal decision?

This is a rhetorical question, of course.  While there may have been circumstances when your back was against the wall as you built your company, it is safe to assume that feeling a ‘gun to the head’ leads to hasty and irrational decisions.  The best decisions we make are done with a considered view regarding the opportunity ahead.  As you look to bring next gens into the family wealth, rather than being driven by concern, can you flip the narrative to consider the opportunities for the next gen and how best to preserve those, knowing of course, that there will be needed risk management for any decisions made.

Second – how have you developed your best talent in the past?

No doubt within the business you had A+ employees that were instrumental in achieving success.  How did you support their own development and encourage their personal careers?  Was it training courses?  Access to leadership opportunities?  If you were able to provide those opportunities to relative strangers, how much more so, should you be able to for those that you know the best, namely your children.   

Third – What are you doing to protect yourself from entitlement?

Most core values and behaviors within a family are caught, not taught.   If you are concerned about your children becoming entitled, start first by going within yourself.  How are you managing your own relationship with wealth?  Do your children see how you behave with wealth?  Do they understand how you make decisions regarding major purchases?  Do you berate the wait staff?  

Fourth – Have you earned the right to express concern about your child’s development?

For many business builders, the primary ‘child’ in their life has been the business.  Long hours, nights, and weekends were invested to make the business successful. For some founders, that meant that the core work of child-rearing and support was left to a spouse or perhaps a household employee.   If you have been underinvesting in the lives of your next gens, do not be surprised if they are not particularly interested in your sudden interest in how they are coming along as people.  

Instead, as the saying goes, seek to understand before being understood.  Building a relationship over time, may give you greater insight into their character.  From that, you will see whether your children are ready to steward the responsibilities of wealth now or how they might need additional development?

Fifth – Where have your own actions contradicted your best intentions?

I heard a story years ago about a child who had graduated and moved to New York for the first job.  Determined to be independent, the child found a small apartment that they shared with friends.  The child’s parents came to visit, and rather than being impressed by the resourcefulness of their child, they were embarrassed by the accommodations as being ‘unbecoming the family’s good name.’  And so, they procured and provided a residence for the child.  Yet within several years, the child was struggling to move forward in life and the parents were not sure why.

Helicopter parenting, snowplow parentings, or simply ego-driven parenting can cause actions that undermine the very values and skills you are trying to teach in future generations.  Consider carefully where you might be the roadblock to the young person developing into their best and highest self. 

No one wants to willingly screw up their children or grandchildren.  It can feel every more intimidating because no one knows exactly why wealth seems to cause some next gens to fly off the rails, while others develop without issue.  Of course, there are no guarantees as to success, but behaving reactively, hastily, or without full consideration cuts you off at the knees before you have even begun to do the hard work.  Hopefully these questions can shed a bit of light on some of the other dynamics at play as you work to grow your family.


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Nashville, TN