Preparing the Next Generation Isn’t the Problem. Avoiding It Is.
A five-part series on raising stewards, not dependents.
Why we created this series
For many business owners, selling a company doesn’t just create liquidity; it creates a legacy. But what happens after the sale is often harder to navigate than the deal itself.
How do you support your children without creating dependency? How do you transition wealth without losing the values that built it? And how do you ensure the next generation is ready, before the moment arrives?
This series explores emotional, practical, and strategic aspects of family wealth stewardship. Based on real-world experience advising families through business transitions, each article is designed to spark conversations and offer a more thoughtful approach to long-term legacy planning.
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Explore the Series
Part One:
The Real Root of Entitlement Isn’t Wealth. It’s Silence.
Why silence, not wealth, creates entitlement
Most families worry about creating “entitled” heirs. But it’s not access to wealth that causes risk—it’s avoiding the hard conversations. In our opening piece, we explore why proactive preparation is the key to responsible legacy planning.
Part Two:
The Lottery Winner Effect
Why unprepared heirs fail and how to build financial muscle memory
Sudden wealth without preparation often leads to poor decisions and fractured trust. We explain why early exposure matters and how to build readiness like any other leadership skill.
Part Three:
Start Small, Stay Intentional
Practical ways to involve the next generation before the capital arrives
You don’t need to give your children control, but you do need to give them context. This article shares small, proven ways to prepare future stewards without handing over the keys.
Part Four:
Set Expectations and Deploy Capital With Purpose
Why timing, clarity, and structure matter more than the amount
When, how, and why you share wealth can shape how it’s used. This piece outlines how to align expectations, navigate complexity, and invest purposefully in the next generation.
Part Five:
Legacy Is a Choice
Why preparation is the most powerful inheritance
Legacy doesn’t happen by accident. In the final part of our series, we explore why real legacy is built through preparation, deliberate choices, shared values, and the leadership it takes to pass them on across generations.
The Complete Guide to Family Wealth Stewardship
How to Prepare Heirs for Family Wealth
A practical guide to multigenerational wealth planning: why most transitions fail, how to avoid entitlement, and what families can do to build financial readiness through structure, trust, and timing.
About the Author
Jason Merrithew is the founder of Peninsula Road, a boutique advisory firm that supports business owners and family enterprises during the sale of their companies and the following transition. Having helped many clients through exits and personally experienced one, Jason brings both insight and empathy to complex family conversations.
Why Peninsula Road
We help families think long-term, not just about money, but what matters.
Values before tactics
We start by understanding what you want to preserve: values, relationships, and purpose, then build the right strategy.
Built for entrepreneurs
We understand wealth created through business. We work with families who want to steward that success across generations.
Discreet and independent
Our advice is private, pragmatic, and grounded in experience: no product sales, no hidden agendas.
Experience that translates
We’ve helped business owners transition wealth, leadership, and responsibility with empathy and structure.
Ready to start the conversation?
At Peninsula Road, we help business owners and family enterprises prepare for more than a sale. If you’re navigating a significant transition or want to design a thoughtful plan for the next generation, we’d be happy to help.