How the Wealthy Actually Plan: Gifting, HSAs, 529s & Estate Structure | Jonathan Meaney

Today on The Wealth Transfer Podcast, Matt Templeton sits down with Jonathan Meaney — Senior Vice President and Wealth Manager at Carter Financial, CFP®, Accredited Investment Fiduciary, and 25-year advisor to high-net-worth families.

This episode cuts through the noise around “financial planning” and breaks down what real planning looks like: comprehensive strategy, long-term decision-making, and aligning assets with actual life goals. Jonathan shares the mistakes he sees wealthy families make over and over, the hidden opportunities most people overlook, and the surprisingly simple tax-advantaged tools that can move millions out of a taxable estate over time.

You’ll hear Jonathan’s take on:

• Why most “financial planners” aren’t actually doing planning

• How 529s can function as one of the most powerful estate-transfer vehicles (and why wealthy families underutilize them)

• The right and wrong way to title property and accounts in a trust

• Annual gifting strategies most families ignore

• Social Security optimization (and how bad timing drains your legacy)

• HSAs as a secret tax-free wealth-building machine

• Why widows/widowers often feel financially insecure — even when they’re objectively more than fine

• How to interview a financial planner (and the red flags to watch for)

Jonathan also gets real about the emotional side of planning — helping people dream again, helping grieving spouses untangle decades of accounts, and helping families pass wealth with intention instead of confusion.

If you want to understand how wealthy families actually plan — not the surface-level investing chatter — this episode is packed with practical insights, real stories, and strategies you can apply today.

🔗 Connect with Jonathan Meaney

Carter Financial Management 🌐 Website: www.carterwealth.com 📞 Phone: [phone]

⏱️ Timestamps & Show Notes

00:00 — Intro to guest: Jonathan Meaney, CFP® Jonathan’s background, market crash beginnings in 2001, and why true financial planning is more than investments.

03:00 — What a financial planner actually does Portfolio alignment, goal-setting, estate strategy, risk management, and why many “planners” don’t actually plan.

07:00 — Planning is ongoing, not a one-time event Why updating the plan matters more than the initial plan.

08:00 — Integrating all assets (including real estate) Why planners must look at everything, not just the stock market.

09:30 — Biggest mistakes wealthy families make

• Naming minors as beneficiaries

• Not retitling assets into a trust

• Social Security timing mistakes

• Skipping annual gifting

12:00 — Why 529 plans are one of the greatest wealth-transfer tools Accelerated gifting, tax advantages, owner control, and multi-generational planning.

18:00 — Tax-free wealth building: HSAs done right How business owners can extract money tax-free and build a medical retirement fund.

20:00 — Helping clients deal with fear and financial anxiety Why widowed clients often feel insecure and how planning provides clarity.

24:00 — Dreaming again: helping clients enjoy their money How planners guide clients to meaningful use of wealth.

26:00 — Stress-testing a financial plan Longevity assumptions, downturn scenarios, disability, and conservative modeling.

27:00 — Why you shouldn’t wait to involve a professional Real-world examples of estate chaos when planning is delayed.

30:00 — How to choose the right advisor CFP designation, red flags, and what to look up on BrokerCheck.

32:00 — The #1 thing Jonathan wishes clients would do Annual gifting and intentional giving during your lifetime.

34:00 — How to connect with Jonathan