Newsletter No. 10 – March 15th, 2024
Written by a human. 

"We cannot change anything until we accept it. Condemnation does not liberate, it oppresses."

I had the privilege of attending a dinner with Jerry Colonna this week. 

For those not familiar with Jerry, he is a pioneering venture capitalist who has become a coach for Fortune 500 CEOs, technology titans, and celebrities around the world. His first book, Reboot, was a powerful influence on my work advising families.

One of the questions Jerry asks is: “How have I been complicit in creating the conditions I say I don’t want”.

The following day after dinner, I facilitated a roundtable discussion with family members from some of the largest and most influential family offices in America.

My topic of discussion was how these family members were creating psychological safety in their families (if they had it at all). For most, this safety didn’t exist. It was sad to hear that so many, despite their family’s extraordinary wealth, were missing the safety to share their hopes, dreams, and perspectives.

Channeling my inner Jerry, I next asked the roundtable participants how they have been complicit in creating the conditions they say they didn’t want.

This simple question changed the energy of the discussion. 

You could see each and every participant stop and begin to reflect on their role and more importantly, what they could potentially do about it.

Being family in a family enterprise can be hard. However, we all have agency over how we’re going to deal with the challenges. Whether we are going to perpetuate the conditions we say we don’t want or be the change that will drive more change.

So, now I want to ask you.

How have you been complicit in creating less-than-ideal relationships with your spouse, partner, kids, siblings, and parents? What action do you need to take to change the conditions to those you do want?

Take just 15 minutes to answer those questions. Write them down and share them with your family. I think you’ll be amazed with the results.

– Josh Gentine

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