How to Introduce Wealth Conversations to the Next Generation

For many parents and grandparents with significant wealth, the hardest financial conversation is not about investments or estate plans — it is the one with their own children. When should they learn about the family’s wealth? How much should they know? How do you talk about money without distorting values?

These questions are not theoretical. How a family introduces wealth to the next generation shapes how that generation relates to it for the rest of their lives. And the research is clear: families that discuss wealth openly, intentionally, and in age-appropriate stages produce better outcomes than families that avoid the conversation entirely.

 

Why the Conversation Keeps Getting Delayed

The most common reason families delay wealth conversations is fear. Parents fear that their children will lose motivation if they learn how much money the family has. They fear judgment from peers. They fear that conversations about money will feel transactional rather than meaningful.

These fears are understandable, but they are based on a misconception: that the only way to talk about wealth is to talk about numbers. The most effective wealth conversations begin long before specific dollar amounts are ever disclosed. They start with values, with family history, and with the principles that shaped how the wealth was created and preserved.

 

A Framework for Starting the Conversation

Wealth conversations should be staged, not delivered as a single event. A practical framework moves through three phases:

  • Phase one — Values and history: Share the family’s story. Talk about the work, sacrifices, decisions, and values that built the family’s position. This phase is about identity, not balance sheets. It is appropriate for children in their teens and can be woven into everyday family life.
  • Phase two — Financial literacy and structure: Introduce basic concepts of investing, charitable giving, and wealth management. Explain that the family has trusts, advisors, and structures designed to preserve wealth for future generations. This phase is appropriate for young adults in their early twenties.
  • Phase three — Governance and participation: Invite the next generation to observe or participate in family meetings, investment reviews, or philanthropic decisions. Share more specific financial information in the context of decision-making — not as an abstract disclosure, but as a practical necessity for informed participation.

 

Common Mistakes to Avoid

The most common mistakes families make when introducing wealth conversations are well-documented:

  • Waiting too long and then disclosing everything at once — typically in a crisis or at a reading of a will
  • Leading with numbers rather than values — turning the conversation into an accounting exercise rather than a discussion about purpose
  • Making the conversation a one-way lecture rather than a dialogue — the next generation’s questions, concerns, and perspectives matter
  • Assuming all children are ready at the same age — readiness varies by temperament, maturity, and life circumstances
  • Delegating the conversation entirely to advisors — professional facilitators can help, but the core messages should come from the family

 

Making It Normal, Not Special

The most successful wealth families are the ones where conversations about money are neither forbidden nor dramatic — they are simply part of how the family operates. This normalization does not happen in a single meeting. It happens through consistent, low-pressure inclusion of the next generation in appropriate conversations over time.

When children grow up understanding that the family has wealth, that it comes with responsibility, and that they have a role to play in its stewardship, the conversation about specific numbers becomes a natural next step rather than a destabilizing revelation.

 

Ready to Take the Next Step?

If you’ve been putting off the conversation about wealth with your children or grandchildren, Vertex Planning Partners can help you develop a structured approach that matches your family’s values and your children’s readiness. Contact an Advisor at in**@************rs.com.

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Peter M. Babilla, CFP®, CRPS®

PARTNER

Peter Babilla brings 40 years of experience in investment management and fiduciary* financial consulting to Vertex Planning Partners, LLC.

Pete graduated from Indiana University in Bloomington, Indiana with a Bachelor’s of Science in Finance.

He began his career in 1983 with a focus on institutional fixed-income portfolio management, primarily working with community banks. After a decade serving institutional clients, Pete shifted his focus to working with individuals, families and business owners, providing guidance and education in all areas of Wealth Management.  Among his areas of focus are accumulation and retirement planning, investment management, risk management, and estate and wealth transfer.

Pete’s planning philosophy allows him to create a personalized program for clients, based on their own unique goals and circumstances.  The extensive investment and planning platform offered by Vertex enables him to create a highly customized program, tailored to each individual client.

Pete and his wife Suzanne have two children, and have resided in Wheaton, Illinois for the past 30 years.  He enjoys golf, reading, and traveling with his family.  Pete gives back as a past Board Member of the Epilepsy Foundation of Greater Chicago, where his focus is on improving the lives of those living with epilepsy.

Pete works as fiduciary for his clients and holds the CERTIFIED FIANANCIAL PLANNER™ (CFP®) designation and the Chartered Retirement Plan Specialist (CRPS®) designation.

Justin J. D'Agostino, CPWA®, CFP® , TPCP®, ChFC®, CRPC®

PARTNER

Justin D’Agostino is a Partner and Private Wealth Advisor at Vertex Planning Partners, advising business owners, executives, and high-net-worth families on investments, financial planning, tax and succession planning.

He coordinates the full advisory team around each client to keep tax, investment, and planning decisions moving in the same direction. Justin’s approach centers on rigorous, data-driven analysis — modeling outcomes across planning scenarios so clients can make decisions with clarity.

With over a decade of experience, Justin’s work focuses on:

  • Investment & Portfolio Strategy
  • Tax-Efficient Planning
  • Equity Compensation & Concentrated Stock
  • Retirement & Distribution Planning
  • Estate & Succession Planning

Justin attended Hillsdale College, where he earned his BA in Accounting and Financial Management. He is an avid sports fan and enjoys spending weekends with his family.

Designations:

  • Certified Private Wealth Advisor®
  • CERTIFIED FINANCIAL PLANNER™ Professional
  • Tax Planning Certified Professional®
  • Chartered Financial Consultant®
  • Chartered Retirement Planning Counselor™

 

Justin does not provide tax or legal advice. He works alongside each client’s CPA and attorney on those matters.

CRPC conferred by College for Financial Planning.

Scott A. Sandee CFP®, CIMA®, CPWA®, CEPA

MANAGING PARTNER

Scott Sandee brings over 20 years of experience to his role as Managing Partner of Vertex Planning Partners, leading the firm’s efforts to assist middle-market business owners and eight and nine-figure families in comprehensive planning. We enable clients to achieve their financial goals by tailoring solutions to their unique aspirations and situations. Leveraging his experience in sophisticated investment techniques and financial strategies with privately held family businesses, supported by extensive post-graduate education focused on exit planning, wealth management, estate planning, investment analysis, insurance planning, risk management, and tax optimization, he:

  • Assist owners in preparing for and executing a successful transition.
  • Develop financial strategies to maximize sales proceeds and reduce future taxes.
  • Listen carefully and create personalized solutions that reflect each client’s unique hopes, goals, and concerns.
  • Explain complex and technical concepts with clarity and simplicity.

 

Scott guides successful entrepreneurs and wealthy families through the transfer of ownership of their privately held companies.

Designations: Certified Financial Planner® Certified Private Wealth Advisor® Certified Investment Management Analyst® Certified Exit Planning Advisor Certified Merger & Acquisition Advisor

Julie Hupp CFP®, MBA

PARTNER

Julie Hupp, CERTIFIED FINANCIAL PLANNER™ professional, has worked in the accounting and corporate finance field since 1987. She began her career as a CPA with Deloitte & Touche, specializing in the financial needs of small businesses. Then spent the next 13 years in corporate financial planning and business development at Baxter and TAP Pharmaceuticals. Recognizing her passion for personal financial planning, Julie started her business in 2006 where she focuses on comprehensive financial planning strategies and implementation.

Julie graduated from University of Illinois with a BS in Accountancy. She received her Master’s in Management with a concentration in Finance from Northwestern University’s Kellogg School of Management in 1994.

Outside the office, Julie is the co-founder of the 12 Oaks Foundation, which has merged with Cal’s Angels, and is a former Board member. Julie enjoys cooking, reading, running, triathlons and doing almost anything outdoors. A great weekend is spending time with her husband and two adult kids boating at their lake house in Wisconsin.

Steven P. Franzen, CPA, PFS, CGMA

MANAGING PARTNER

Steven P. Franzen, CPA, PFS, CGMA is a public accountant and consultant with more than 23 years of experience helping individuals and businesses reduce their tax liability.  He began his career under the guidance of Patrick M. De Sio, CPA, CGMA and in 1996 became Mr. De Sio’s partner in De Sio, Franzen & Associates, Ltd. Steve’s expertise include entity design, complex tax strategies and multigenerational wealth transfer.  As Managing Partner, Steve conducts his practice under the philosophy that the client’s investment in their CPA should yield a return on that investment – most of the time that return is realized when working with clients on planning for their future. In an effort to increase the planning capabilities of the firm,  Steve formed Vertex Accounting Partners, LLC to ensure their guiding philosophy will continue well into the future.

Steve is a certified public accountant and has earned the professional designations of Personal Financial Specialist and Chartered Global Management Accountant.  He is a member of the American Institute of Certified Public Accountants and the Illinois CPA Society.  Steve earned a B.S. degree in accounting from Millikin University.  He and his wife Kristie live in Sugar Grove, IL with their three children.

Gregory P. Benner, MST, CPWA®, CFP®, CLU®, ChFC®, AIF®, RMA®

MANAGING PARTNER

Greg Benner advises high-net-worth and ultra-high-net-worth business owners, individuals and families on advanced tax, risk management, retirement, estate planning, and wealth strategies.  

As a co-founder of Vertex Planning Partners, he works closely with clients, families, and their professional advisors—CPAs, attorneys, and business stakeholders—to implement thoughtful, durable planning strategies. His approach prioritizes clarity, coordination, and disciplined execution.

For twenty-four years, Greg’s work has focused on designing and coordinating multi-factor, integrated plans involving:

  • Tax Efficiency
  • Wealth Transfer Structures
  • Retirement Planning
  • Investment Strategy, and
  • Long-Term Financial Architecture

 

Drawing from his own experience as a founder, business and real estate investor, and multi-generational family business member, he understands some of the challenges that can arise for business owners as they consider an exit. Multi-disciplinary, intentional planning with stakeholder communication creates structure, mitigates risk, addresses tax implications, and preempts issues that can arise.

Greg holds a Master of Science in Taxation, a graduate program that deepened his technical training in federal income taxation, partnership and corporate taxation, estate and gift tax, and tax procedure. This academic work enhances his ability to help families and business owners navigate complex tax environments and align their financial and estate-planning objectives across generations.

Designations:

  • Certified Private Wealth Advisor®
  • Certified Financial Planner®
  • Chartered Financial Consultant®
  • Chartered Life Underwriter®
  • Accredited Investment Fiduciary®
  • Retirement Management Advisor®

 

Licenses:

  • Series 65 registration held with Vertex Planning Partners, LLC
    Illinois, Ohio, Wisconsin & Louisiana Life & Health Insurance License

 

Greg is deeply committed to lifelong learning and continuous professional development in the areas of tax, estate planning, and private-wealth strategy.

Michael D. Bellis, CFP®, CLU®

MANAGING PARTNER

Michael D. Bellis, CFP®, CLU® began his career as a financial planning professional in 1994. His practice is centered on holistic financial planning, astute risk management strategies and empirical, research-driven portfolio construction. He began his career in partnership with his father under the name Bellis & Associates. Together, their practice and reputation for excellence dates back more than 40 years and includes multiple generations of the same families. After his father’s retirement several years ago, Mike continued to build a client-centric, consultative practice before forming Vertex.

Mike holds the CERTIFIED FINANCIAL PLANNER™ certification and is also a Chartered Life Underwriter. He has been an active member of both the Society of Financial Services Professionals and the National Association of Insurance and Financial Advisors. He earned a B.S. in Business & Marketing from Illinois State University. Mike is a lifelong resident of Naperville, Illinois. He and his wife Tanja have three children.