Here's a question most people never ask: What will your family look like in 2125?
Not just your assets. Your family. The people who will carry your name, your values, your stories—or won't. The relationships that will hold strong or fracture. The opportunities your decisions today will create or foreclose a century from now.
Most estate planning treats legacy as a transaction—Who Gets What? Divide the assets, sign the documents, done. Estate attorney Derek Jensen questions that approach and discovered that families who thrive across generations think completely differently. They're not planning for a moment of transfer. They're architecting systems that strengthen over time.
Through candid conversations with wealth advisors, financial philosophers, and families who've cracked this code, Derek explores the real work of multi-generational thinking. Not just trusts and tax strategies, though those matter, but the conversations, values, and practices that keep families unified and thriving long after you're gone.
Whether you're building wealth from scratch, inheriting, helping aging parents navigate their decisions, or preparing the next generation for what's coming—you're part of a chain that extends far beyond your lifetime.
This show is about understanding that responsibility and embracing that possibility. Because the best estate plans aren't documents. They're living systems that grow stronger with each generation.
In this Season One finale, estate attorney Derek Jensen goes solo to break down Washington State's changing tax landscape and why most families remain dangerously unprotected despite the new laws. On July 1st, Washington's top estate tax rate drops from 35% to 20%. That sounds like good news. But the exemption is also pulling back, the gap between Washington's $3M threshold and the federal $15M exemption hasn't changed, and an estimated 100,000–150,000 Washington households are still caught i...
21 May 2026
Never Say “This Will Be An Easy Trust” with Allison Ferris
Derek sits down with Allison Ferris, Chief Fiduciary Officer at Northwest Trustee and Management Services, to discuss what happens after a trust is established. Allison shares lessons from more than 18 years in fiduciary work, including why she never says, “This will be an easy trust.” They discuss family cabins, unexpected assets, beneficiary emotions, co-trusteeship during incapacity, and why clear, flexible drafting matters so much when a plan may need to work decades from now. This episod...
7 May 2026
The People Behind the Plan with Derek Jensen
Estate planning is more than trusts and documents. It's about people, values, and the future. In this episode, Derek shares the unexpected lessons from a career of guiding families through wealth transitions. What makes a good trustee? When should you talk to your beneficiaries? And what happens when the plan looks perfect on paper but the people aren't ready? Derek explores the real responsibilities of a fiduciary, the rise of incentive and wellbeing trusts, and why the conversations you hav...
16 Apr 2026
The Myth of the Silver Spoon with Kristin Keffeler
What happens when the inheritance arrives and nobody prepared the people receiving it? Kristin Keffeler, author of The Myth of the Silver Spoon and co-author of Wealth 3.0, joins Derek to challenge the assumption that wealth transfer is just a financial event. Drawing from her own experience as the daughter of wealth-creating parents, Kristin explores the psychological barriers inheritors face, why a growth mindset matters more than a trust document, and how to start financial conversations w...
2 Apr 2026
The 14 Page Questionnaire That will Change Your Life with Tom Flannagan
What if the most important part of your estate plan isn't the trust — it's the questionnaire? Derek sits down with Tom Flannagan, the estate attorney who inspired Who Gets What?, to explore his comprehensive approach to planning that starts with 14 pages of questions most attorneys never think to ask. They cover risk mitigation, tax strategy, and the surprising details that make a plan actually work, from digital assets to beach passes. Learn more about Who Gets What?: https://whogetswh...
19 Mar 2026
Wisdom and Family Wealth with Chris Kelley and Chad Johnsrud
BNY Wealth Advisors Chris Kelly and Chad Johnsrud join host Derek Jensen to address the complex realities of managing inherited wealth, discussing strategies, family values, and the intricacies of estate planning. They talk about the importance of planning, seeking professional help, and maintaining family communication to ensure the smooth transfer of wealth across generations. Chris and Chad share stories and insights from their extensive experience, providing listeners with actionabl...
5 Mar 2026
Why Does Your Family Wealth Story Matter?
We’ve all heard the saying “shirtsleeves to shirtsleeves in three generations”—but why does this happen, and how can your family break the cycle? This episode dives deep into the often-overlooked foundation of lasting wealth: your family’s unique story, values, and relationships. True wealth continuity is a challenge of human dynamics, not just financial engineering. This episode examines the central, yet frequently ignored, component of successful multi-generational planning: the family narr...
19 Feb 2026
Healthy, Wealthy and Wise with Covie Edwards Pitt
Derek Jensen sits down with Covie Edwards Pitt, author and the creative director of Balentine Partners and the founding director of Balentine's Center for Family Wellbeing. They discuss Covie’s book series 'Healthy, Wealthy, and Wise,' touching on Wealth 3.0 and how best practices in wealth advisory translate to real life. Covie shares the important lessons learned from her book series — the complexities of nurturing children amid newfound wealth, the role of spousal partnerships in man...
5 Feb 2026
What Your Story Says About You with Caleb Breakey
Caleb Breakey, founder of Renowned Publishing, joins Derek Jensen for a conversation on the most powerful legacy-building tool we all possess: our story. Having guided over 200 people in transforming their lives into books, Caleb reveals why storytelling isn't just for authors; it's a sacred practice for anyone who wants their wisdom, values, and experiences to endure. Check out Renowned Publishing: https://www.renownpublishing.com/begin Learn more about Who Gets What?: https://whogetsw...
15 Jan 2026
HEIR-conditioning with Paul Adams
What is the true purpose of wealth? Is it independence, security, or leaving a mark? Financial philosopher and CEO & Founder of Sound Financial Group Paul Adams joins Derek Jensen for a profound conversation that moves way beyond the spreadsheet. They explore how to build a legacy defined not by the size of an inheritance, but by the strength of the values behind it. Paul shares why financial independence is the bedrock of honest advice, how to have transparent money conversations t...
1 Jan 2026
The Family Bank with Emily Griffiths-Hamilton
What’s the secret to keeping a family and its wealth intact for four generations? For author and CA Emily Griffiths-Hamilton, the answer isn’t in a trust fund; it’s in a value system. She joins host Derek Jensen to share her family’s extraordinary journey, revealing how they built a “family bank” rooted in social capital and open communication. Learn how they passed down enterprises and ethics in equal measure, and discover why having tough conversations about money is the key to ensuri...
18 Dec 2025
Guiding Future Generations with Chip Fisher
What if everything you've been told about inheritance is wrong? What if a "silver spoon" isn't a privilege, but a profound responsibility? Chip Fisher, founder of Urusus Advisory, sits down with Derek Jensen to challenge the greatest taboo of wealth and the emotional weight it places on heirs. They explore how to transform an inheritance from a burden into a "launchpad," break the silence that cripples families, and leverage the true superpower of passed-down wealth: not the money itsel...
5 Dec 2025
Who Gets What? | Trailer
Here's a question most people never ask: What will your family look like in 2125? Not just your assets. Your family. The people who will carry your name, your values, your stories — or won't. The relationships that will hold strong or fracture. The opportunities your decisions today will create or foreclose a century from now. Most estate planning treats legacy as a transaction—Who Gets What? Divide the assets, sign the documents, done. Estate attorney Derek Jensen questions that approach and...
4 Dec 2025
From Seattle to Silicon Valley with Elijah Keyes
What does a California estate attorney see when he looks at Silicon Valley's wealth? Not just IPOs and unicorns, but a generation facing unprecedented legacy challenges. Elijah Keyes joins Derek Jensen with stories from the front lines of tech wealth in California. They dive into the psychological shifts required to go from "creator" to "steward," the critical importance of a "comprehensive team" (and what that really means), and how to plan an estate that thrives long after the stock o...
20 Nov 2025
Operating Your Household Like a Business with Walter Young
We all know about budgets and retirement accounts. But what about a Family Constitution? Host Derek Jensen and guest Walter Young push beyond basic financial literacy to explore the human side of wealth. They discuss how to escape scarcity thinking, why you should run your family like a business, and how to transform life insurance from a simple safety net into a dynamic tool for building a legacy that reflects your family's core values. Learn more about Walter’s book and his forthcoming fina...
5 Nov 2025
A Conversation with My Dad
Derek Jensen built a career helping families plan their estates. But he realized he'd never had the real conversation with his own father about their family's century-old heritage property in Montana. His father is one of seven siblings, now one of only two remaining from his generation. As an officer of the family corporation that owns the land, he's navigating an impossible balance: honoring the past, serving the present, and preserving possibilities for a future he won't see. In this deepl...
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