In this special Season 1 finale, Penny DiGiovanna reflects on what she’s learned from a year of conversations about legacy, wealth, and family governance.

From second marriages and blended families to business transitions and inheritance dynamics, this episode looks back at the themes that shaped the first season of The Family Wealth Blueprint Podcast — and forward to the frameworks that will define the next.

Penny shares how clarity, communication, and structure work together to help create lasting continuity — and why the most successful families design their wealth around relationships, not just returns.

In This Episode You’ll Hear:

• Why clarity and connection matter more than complexity.
• What Penny learned working with multi-generational families this year.
• How structure and stewardship protect not only assets — but family harmony.
• A preview of what’s ahead in Season 2: Designing the Family Enterprise Framework.

About Penny DiGiovanna
Founder & CEO of Financial Planning By Design, Penny helps multi-generational families align wealth, values, and relationships through a planning-first Virtual Family Office model. Her signature process, The Family Wealth Blueprint, integrates financial strategy with family governance to create clarity and continuity across generations.

Disclaimer
This podcast is for educational and informational purposes only and does not constitute investment, legal, or tax advice. Opinions expressed are those of Penny DiGiovanna and Financial Planning By Design. Please consult your own advisors before making any financial decisions.

Hosted by Penny Di Giovanna, CFP®, CDFA®
Founder of Financial Planning By Design | Multi-Gen Family Planning - Boutique Virtual Family Office

🔗 Learn more: www.financialplanningbydesign.com
📩 Questions or topic suggestions?

Email: penny@financialplanningbydesign.com

💡 Like what you hear? Subscribe and share this episode with someone navigating life’s complexities.

Podcast Disclaimer:

This podcast is for informational and educational purposes only and is not intended as investment, legal, or tax advice. Opinions expressed are those of Penny Di Giovanna and do not constitute a recommendation to take any particular action. Financial Planning By Design is a registered investment advisor. Advisory services are only offered to clients or prospective clients where Penny and the firm are properly licensed or exempt from licensure. All investments involve risk, and past performance is not indicative of future results. Consult your financial, legal, or tax advisor before making any decisions.

A Tale of Two Inheritances

What makes the difference between a smooth wealth transfer and a family crisis?

In this episode of the Family Wealth Blueprint Podcast, Penny DiGiovanna shares a “tale of two inheritances.” One story highlights the issues that can occur when documents are outdated and communication is missing especially when an unexpected death occurs. The other shows how proactive planning, clear governance, and advisor collaboration can help create a smoother, more tax-efficient transition.

You’ll hear:

• Why even updated estate documents may fall short without governance
• Why family transitions need to be addressed carefully and quickly
• How proactive communication helps reduce the risk of costly litigation
• The challenges families face when financial institutions freeze assets
• How preparation can empower heirs to focus on healing instead of conflict

These stories are based on a mix of real and hypothetical scenarios. They illustrate how family governance, when done properly, can reduce stress and preserve harmony — but every family’s situation is unique. Families should consult their own qualified tax, legal, and financial professionals before making decisions.

Hosted by Penny Di Giovanna, CFP®, CDFA®
Founder of Financial Planning By Design | Multi-Gen Family Planning - Boutique Virtual Family Office

🔗 Learn more: www.financialplanningbydesign.com
📩 Questions or topic suggestions?

Email: penny@financialplanningbydesign.com

💡 Like what you hear? Subscribe and share this episode with someone navigating life’s complexities.

Podcast Disclaimer:

This podcast is for informational and educational purposes only and is not intended as investment, legal, or tax advice. Opinions expressed are those of Penny Di Giovanna and do not constitute a recommendation to take any particular action. Financial Planning By Design is a registered investment advisor. Advisory services are only offered to clients or prospective clients where Penny and the firm are properly licensed or exempt from licensure. All investments involve risk, and past performance is not indicative of future results. Consult your financial, legal, or tax advisor before making any decisions.

In this episode of The Family Wealth Blueprint Podcast, Penny shares Rachel’s story: a successful entrepreneur who built a real estate portfolio and finds herself navigating the complexities of divorce. On the surface, it looked like success. Underneath, the lack of coordination between her advisors, outdated estate documents, and absence of protection strategies exposed her wealth and family to serious risk.

You’ll learn:

• How divorce often leaves ownership, titling, and estate plans dangerously outdated
• The tax opportunities missed when real estate isn’t structured intentionally
• The critical role of risk management and entity planning in safeguarding wealth
• How a Virtual Family Office approach pulls the legal, tax, and insurance pieces together for true protection

Rachel’s story is a cautionary tale—but it’s also a roadmap. With the right structure and coordinated planning, families can avoid costly mistakes and preserve both their assets and their legacy.

Subscribe for more episodes on family governance, strategic planning, and real-world lessons from multi-generational families.

This podcast is for informational and educational purposes only and is not intended as investment, legal, or tax advice. Opinions expressed are those of Penny Di Giovanna and do not constitute a recommendation to take any particular action. Financial Planning By Design is a registered investment advisor. Advisory services are only offered to clients or prospective clients where Penny and the firm are properly licensed or exempt from licensure. All investments involve risk, and past performance is not indicative of future results. Consult your financial, legal, or tax advisor before making any decisions. Any resemblance to real persons, living or dead, or actual events is purely coincidental.

Hosted by Penny Di Giovanna, CFP®, CDFA®
Founder of Financial Planning By Design | Multi-Gen Family Planning - Boutique Virtual Family Office

🔗 Learn more: www.financialplanningbydesign.com
📩 Questions or topic suggestions?

Email: penny@financialplanningbydesign.com

💡 Like what you hear? Subscribe and share this episode with someone navigating life’s complexities.

Podcast Disclaimer:

This podcast is for informational and educational purposes only and is not intended as investment, legal, or tax advice. Opinions expressed are those of Penny Di Giovanna and do not constitute a recommendation to take any particular action. Financial Planning By Design is a registered investment advisor. Advisory services are only offered to clients or prospective clients where Penny and the firm are properly licensed or exempt from licensure. All investments involve risk, and past performance is not indicative of future results. Consult your financial, legal, or tax advisor before making any decisions.

In this episode of The Family Wealth Blueprint, Penny shares the cautionary story of the Millers—a family who lost more than a loved one when their business-owning patriarch passed away.

Without clear succession planning, governance, or communication, their family and business were left scrambling.

Penny explores what went wrong, why human and intellectual capital are just as vital as financial capital, and how proactive, holistic planning can prevent this from happening to your family.

Disclaimer: The story and characters described in this episode are fictitious and created for illustrative purposes only. Any resemblance to actual persons, families, or events is purely coincidental.

🎧 A must-listen for business owners, successors, and the professionals who serve them.

Learn more at financialplanningbydesign.com

Hosted by Penny Di Giovanna, CFP®, CDFA®
Founder of Financial Planning By Design | Multi-Gen Family Planning - Boutique Virtual Family Office

🔗 Learn more: www.financialplanningbydesign.com
📩 Questions or topic suggestions?

Email: penny@financialplanningbydesign.com

💡 Like what you hear? Subscribe and share this episode with someone navigating life’s complexities.

Podcast Disclaimer:

This podcast is for informational and educational purposes only and is not intended as investment, legal, or tax advice. Opinions expressed are those of Penny Di Giovanna and do not constitute a recommendation to take any particular action. Financial Planning By Design is a registered investment advisor. Advisory services are only offered to clients or prospective clients where Penny and the firm are properly licensed or exempt from licensure. All investments involve risk, and past performance is not indicative of future results. Consult your financial, legal, or tax advisor before making any decisions.

In this episode, we explore what family wealth planning really looks like at Financial Planning By Design. This isn’t just about money—it’s about people, purpose, and the kind of legacy that holds meaning across generations.

I’ll introduce you to our signature process, the Family Wealth Blueprint, and how it serves as a strategic guide for families who want to move forward with clarity, collaboration, and deep-rooted intention.

If you’re navigating succession, complexity, or simply want to ensure your family’s future is built on more than numbers, this episode is where we begin—with stewardship at the heart of it all.

Hosted by Penny Di Giovanna, CFP®, CDFA®
Founder of Financial Planning By Design | Multi-Gen Family Planning - Boutique Virtual Family Office

🔗 Learn more: www.financialplanningbydesign.com
📩 Questions or topic suggestions?

Email: penny@financialplanningbydesign.com

💡 Like what you hear? Subscribe and share this episode with someone navigating life’s complexities.

Podcast Disclaimer:

This podcast is for informational and educational purposes only and is not intended as investment, legal, or tax advice. Opinions expressed are those of Penny Di Giovanna and do not constitute a recommendation to take any particular action. Financial Planning By Design is a registered investment advisor. Advisory services are only offered to clients or prospective clients where Penny and the firm are properly licensed or exempt from licensure. All investments involve risk, and past performance is not indicative of future results. Consult your financial, legal, or tax advisor before making any decisions.

In this debut episode, Penny Di Giovanna shares the story of a successful second-marriage couple who blended their lives—but not their finances.

He owns multiple businesses.
She’s a high-earning executive with real estate assets.
They’ve built a beautiful life together—yet they’re financially exposed, with outdated wills and no coordinated plan.

This isn’t rare. It’s a trap.

In today’s episode, you’ll hear:

• Why second marriages require intentional financial planning
• The hidden risks of doing nothing
• How to prevent unintended inheritances, business complications, and family conflict

If your life is complex, your plan should be too—on purpose.

Disclaimer: The story and characters described in this episode are fictitious and created for illustrative purposes only. Any resemblance to actual persons, families, or events is purely coincidental.

Hosted by Penny Di Giovanna, CFP®, CDFA®
Founder of Financial Planning By Design | Multi-Gen Family Planning - Boutique Virtual Family Office

🔗 Learn more: www.financialplanningbydesign.com
📩 Questions or topic suggestions?

Email: penny@financialplanningbydesign.com

💡 Like what you hear? Subscribe and share this episode with someone navigating life’s complexities.

Podcast Disclaimer:

This podcast is for informational and educational purposes only and is not intended as investment, legal, or tax advice. Opinions expressed are those of Penny Di Giovanna and do not constitute a recommendation to take any particular action. Financial Planning By Design is a registered investment advisor. Advisory services are only offered to clients or prospective clients where Penny and the firm are properly licensed or exempt from licensure. All investments involve risk, and past performance is not indicative of future results. Consult your financial, legal, or tax advisor before making any decisions.