Beyond the Balance Sheet: Jessica McGawley on Preparing the Rising Gen

Let’s Talk Family Enterprise Podcast Episode #83

Host: Steve Legler
Guest: Jessica McGawley

Host Steve Legler is joined by Jessica McGawley, founder of Dallington, a boutique London firm supporting families with the developmental and relational sides of significant wealth. For the past decade, Jessica and her team have worked exclusively with teens and 20-somethings in enterprising families, a generation often left out of conversations that will shape their futures.

Drawing on her recent Financial Times article, Jessica explores why well-meaning wealth managers, lawyers and trustees can sometimes cross professional boundaries with younger family members, and why an advisor who has served the parents for decades may not be a neutral presence in a child’s life.

Jessica and Steve also discuss confidentiality and cultural expectations, preparing young people for public attitudes toward wealth, and how her Rising Gen program helps siblings and cousins explore the different paths their family enterprise might take and what each could mean for their relationships and responsibilities.

Jessica closes with a reading recommendation for parents and advisors, and a reminder that exceptional business leaders and wealth creators may need more support as parents than we sometimes assume.

Links
Atlantic publication, Russell Shaw https://www.theatlantic.com/newsletters/2026/08/how-raise-resilient-children/688449/

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