Estate Planning: PortfolioPilot vs FreeWill

According to Caring.com’s 2025 survey, only 24% of US adults have a will, down meaningfully from pre-pandemic levels. For many, the sticking point isn’t intent but execution: people worry estate planning means hiring a lawyer immediately or filling out forms they don’t fully understand. The real issue is that estate decisions touch investments, taxes, and beneficiaries that may change over time. This article explains how PortfolioPilot (planning, coordination, and reminders) compares with FreeWill (document creation and charitable bequests) so readers can see where each tool tends to fit.

Key Takeaways

1. Different jobs: PortfolioPilot organizes financial data and surfaces estate to-dos; FreeWill focuses on creating estate documents online.
2. Beneficiary designations matter: Accounts that name beneficiaries or have transfer-on-death instructions typically bypass probate, which is why keeping forms current is critical.
3. Rules can change: Federal estate-tax thresholds are scheduled to revert to pre-2018 levels (inflation-adjusted) after 2025 under the TCJA’s sunset provision - another reason periodic updates may help.

What PortfolioPilot Brings to Estate Planning (Planning & Coordination)

PortfolioPilot’s estate features are designed to connect legal intentions with a person’s actual financial picture.

• Planning, not drafting: PortfolioPilot does not produce legal documents. Instead, it turns a person’s real accounts and holdings into an estate planning checklist and timeline, making it easier to walk into an attorney’s office prepared. 
• Beneficiary visibility: Because investment and retirement accounts often pass by beneficiary designation or TOD (transfer on death), PortfolioPilot’s portfolio view can help highlight where designations may need attention. This is practical because beneficiary-named assets generally settle outside of probate.
• Integrated reminders: As accounts, balances, or family structures change, prompts to re-review items - like primary vs. contingent beneficiaries - can reduce costly oversights later.
• Tax and portfolio context: Estate planning conversations often intersect with asset location, cost basis, and charitable intent; PortfolioPilot’s broader view across accounts supports that discussion with an attorney. (PortfolioPilot is published by an SEC-registered investment advisor and provides ongoing guidance rather than document prep.)

So what? When estate to-dos are tied directly to live account data and surface as tasks, many investors find it easier to follow through - before meeting a lawyer.

What FreeWill Brings (Document Creation & Charitable Gifting)

FreeWill is an online platform oriented around creating estate documents and facilitating charitable bequests.

• Online wills and related tools: FreeWill offers workflows to create basic estate documents and has deep connections to charitable giving programs.
• Not a law firm: FreeWill explicitly states it is not a law firm and does not provide legal advice; it offers tools that users may take to an attorney for review.
• Charitable focus: The company also publishes planned-giving research and resources oriented to philanthropy.

Why it matters: Many people want a low-friction way to draft initial documents or to incorporate charitable intent. FreeWill can help start that process online - especially for straightforward situations - while leaving room for attorney review.

Side-by-Side: Where Each Option Often Fits

PortfolioPilot and FreeWill can be complementary when used for the jobs they’re built to do.

• When PortfolioPilot may help most
  
  • A person wants an always-updating checklist tied to real accounts.
  • There’s a need to see which assets already pass by beneficiary or TOD and to set reminders to keep those forms current (beneficiary-named assets typically bypass probate).
  • The family expects portfolio or tax complexity to evolve, and prefers a planning view that updates over time (e.g., account consolidations, new retirement plans, or changing state residency).
• When FreeWill may help most
  
  • A person wants to draft a simple will online to take to a lawyer for review or signing.
  • Charitable bequests are a key motivation, and the user wants templated prompts to include nonprofits.
• When both are used together
  
  • PortfolioPilot surfaces beneficiary and account-level action items; FreeWill turns the intent into draft documents; an attorney finalizes state-specific language.
    
• What neither replaces
  
  • Complex situations—business ownership, multi-state real estate, special-needs planning, trust tax questions - frequently warrant an estate planning attorney. (Federal rules also evolve; the TCJA’s higher exclusion is scheduled to sunset after 2025.)