Speaking & Interviews

How Do We help the next generation become more capable while strengthening family relationships?

We are living through the largest transfer of wealth in history. Trillions of dollars are moving from one generation to the next, while many families are quietly struggling with questions that money alone cannot solve.

How much should we help? When does support become dependence? How do we prepare our children for responsibility, stewardship, and decision making while keeping relationships strong?

I don’t approach these questions as a financial advisor or estate attorney. I approach them as a parent who found herself wrestling with the same challenges many families face. What emerged was a deeper conversation about inheritance, capability, family systems, and what it actually means to prepare the next generation well.

Ann Webb

The question Nobody is Asking

We have an entire industry dedicated to helping families transfer wealth. Financial advisors, attorneys, accountants, and estate planners all play an important role.

But many families eventually discover that the greatest challenges aren’t financial. They’re human. Communication. Responsibility. Decision making. Stewardship. The skills required to navigate opportunity well.1`

"We have an entire industry dedicated to preparing assets for heirs.

But who is preparing  heirs for assets?"

What I bring to the Conversation

I don’t speak as a financial advisor, attorney, or economist. I speak as a parent who found herself wrestling with the same questions many families face.

After selling our business, my husband Scott and I began asking questions about inheritance, responsibility, opportunity, and what it actually means to prepare the next generation well. What started as a family experiment eventually became a framework we now live inside every day.

The ideas I share come from real experience, real mistakes, and real conversations. Not theory. Not research. A family trying to build capability, stewardship, and stronger relationships at the same time.

Conversation themes

These are starting points for conversation. Each discussion is tailored to the audience and tends to be interactive and story-based.

Helping Without Hurting
How do we support the next generation without creating dependence? A conversation about generosity, capability, and the unintended consequences of financial help

Preparing Heirs for Assets
We have an entire industry dedicated to preparing assets for heirs. But who is preparing heirs for assets? A conversation about stewardship, responsibility, and readiness.

From Inheritance to Stewardship
What if inheritance isn’t the most important transfer happening? Exploring how families pass down values, decision making, communication, and responsibility.

The Family Experiment
The story of how our family went from asking “How much should we leave our kids?” to building structures that create opportunity, accountability, and growth while we’re still alive.

The New Rules of Generational Wealth
The largest wealth transfer in history is underway. What might families need beyond trusts, investments, and estate plans to navigate it successfully?

Great Fit For

• Financial advisor client events

• Family office and wealth education programs

• Estate planning and legacy focused audiences

• Entrepreneur and business owner communities

• Families navigating generational wealth conversations

• Podcasts and interview based discussions

What Hosts Can Expect

This isn’t a technical presentation about trusts, taxes, or investment strategies. It’s a conversation about the people side of wealth.

Hosts can expect:

• Real stories that audiences connect with

• Thought provoking questions that continue long after the event

• Practical examples from a family living this work in real time

• A perspective that challenges assumptions without creating judgment

• An engaging, conversational style that encourages participation

Let’s Connect

If you are hosting a podcast, event, or conversation and this topic resonates, I would love to be part of it.

Complete this form & let's start the conversation