Retire With 4M · Journal Entry #044

Kid art thumbnail

Investing for Heirs: Why We Skip the 529

Living in California means the tax benefits of a 529 are minimal. Instead, we use siloed brokerage and retirement accounts to build a flexible foundation for the next generation.

The California Context: Tax-Perk Reality

In many states, funding a 529 plan comes with a juicy state tax deduction. In California, that deduction doesn't exist. You are contributing post-tax dollars into an account that, while growing tax-free for education, carries heavy penalties if the funds are used for anything else.

For our heirs, we prioritize Optionality . If a traditional four-year degree is replaced by trade schools, specialized bootcamps, or a business venture, we don't want our capital trapped in a 529. Instead, we open dedicated Custodial Brokerage and Retirement (Roth IRA) accounts.

The Strategy of "Named Buckets"

Even though we use standard brokerage accounts, we keep them siloed. Giving the investment account a specific name (e.g., "Heir A - Growth & Life") helps us psychologically distance it from our core $4M portfolio. It has its own mission: to leverage the massive runway of an 18-to-25-year time horizon.

Operating principle: Consistency over complexity. Small, automated contributions started at birth beat a massive lump sum dropped in at age 15.

Visualization: The Power of $100 vs. $500

What happens when you consistently buy the S&P 500 (VOO) for an heir? This chart shows the growth over 18 years, assuming an 8% annual return.

VOO Growth Projection (18 Years)

$500/mo: ~$240,000 $100/mo: ~$48,000 Birth Age 18
● $100/month contribution ● $500/month contribution

Starting with just $100 a month provides a massive "launchpad" for an heir. At $500 a month, you have effectively fully funded a major university education—but with the flexibility to use that capital for a downpayment or a startup if college isn't the chosen path.

Why Optionality Wins

The world of 2040 will look vastly different than today. College degrees may no longer be the primary signal for high-value careers. By using brokerage accounts:

  • No "Education-Only" Lock: Use the money for a home, a business, or specialized training without a 10% penalty.
  • Tax Efficiency: While you pay capital gains, you can harvest losses or utilize the heir's likely lower tax bracket for withdrawals.
  • Generational Compounding: If the funds aren't needed at 18, they stay in the market, potentially growing into a retirement fund for the heir's heirs.

90-Day Heir Funding Plan

  1. Open the Silo: Set up a custodial brokerage account separate from your main logins.
  2. Name the Goal: Label it clearly to prevent "portfolio creep."
  3. Automate the Buy: Set a recurring monthly purchase of VOO (S&P 500) or VTI (Total Market).
  4. Roth Pivot: As soon as the heir has any earned income (tutoring, summer jobs), open a Custodial Roth IRA and shift contributions there to capture permanent tax-free growth.

Final Take

Investing for heirs isn't about picking the "perfect" tax shelter; it's about giving them the gift of time. In California, the flexibility of a standard brokerage account combined with the psychological power of a named silo creates a more resilient generational system than a rigid 529. Build the launchpad, automate the flight, and let compounding do the rest.

Back to top