The peculiar thing about an estate plan is that you can own one without understanding it. There are signatures. There are trusts. There may be a reassuringly thick folder. But ask a simpler question - who receives what, and when? - and the paperwork can become surprisingly unhelpful. Vanilla has built its business around making that answer visible.
- The buyer: financial advisors and wealth management firms.
- The product: estate diagrams, document tools, and strategy modeling.
- The bet: understanding a plan creates an ongoing advisory relationship.
Founded in 2019 by financial advisor Steve Lockshin and entrepreneur David Hauser, Vanilla began with an unusually useful pairing: the advisor and the advised. Hauser had become Lockshin’s client after selling Grasshopper. The problem they tackled was familiar from both sides of the desk. Estate planning could be expensive, difficult to explain, and awkward to maintain.
01 The lawyer at every turn
The first approach had its own friction. In May 2023, CEO Gene Farrell told WealthManagement.com that Vanilla’s original structure required an attorney for every engagement. Customers were asking for something easier. The company moved toward an integrated estate advisory platform, putting visualizations, projections, and the advisor’s continuing relationship at the center.
“Many users just wanted an easy, flat fee experience”
Gene Farrell / CEO, Vanilla / 2023
This was a change in what counted as the product. Producing the document remained useful. Helping someone understand it, discuss alternatives, and return to it later became the larger job. A family’s circumstances do not stop changing when the ink dries.
02 Put the inheritance on the table
Today, an advisor can bring together a household’s family information, assets, and existing estate documents. Vanilla turns that material into diagrams, beneficiary summaries, and reports. Its balance sheet can draw information from systems including eMoney, Orion, Addepar, and Black Diamond, reducing the amount of financial information someone must enter twice.
The revealing output is the waterfall: a visual account of where assets flow. Advisors can examine different assumptions, including which spouse dies first. That makes a dense legal arrangement available for discussion. A client can point to a destination and ask why the money is going there.
+ documents
+ asset flows
+ advisor review
Conceptual workflow, not a client outcome.
Vanilla Scenarios adds comparisons. Advisors can model gifting, trust strategies, or a move between states, then show how the assumptions alter projected distributions and taxes. A quick illustration can start with broad net-worth figures; a detailed model can use the underlying balance sheet. Clients see the output through their advisor or a report.
For clients who need documents, Document Builder uses guided questionnaires and attorney-drafted templates for wills, trusts, and other essentials. For situations requiring tailored legal work, Vanilla offers access to an attorney network. Concierge services add human estate expertise. The system has several entry points because a client arriving with no will has a different problem from a family arriving with several trusts.
03 A pilot beats a promise
Vanguard supplies a concrete example of how Vanilla entered institutional wealth management. The firms began working together in 2022. In January 2024, Vanguard announced plans to expand access after a pilot with eligible advised clients, offering visualizations, estimated taxes, and estate monitoring to ultra-high-net-worth investors in its wealth management service.
Mariner offers another test. An April 2025 announcement extended the relationship to more than 700 advisors. Vanilla reported a 200% increase in revenue growth rates among advisors adopting it for holistic planning. Its accompanying study describes a correlation between usage and performance. Enthusiastic adopters may differ from other advisors in several ways; the number does not establish that software alone caused the growth.
Covered by the expanded relationship announced in April 2025.
Vanilla competes in an increasingly busy category alongside Wealth.com, FP Alpha, EncorEstate Plans, and Trust & Will. Its pitch combines visual analysis, scenario modeling, document creation, and specialist support. Buyers should compare how those pieces fit their practice. The spreadsheet and the hand-drawn diagram remain competitors, too.
04 The price of keeping the conversation going
The core business is a subscription sold by user and license type. Vanilla’s current pricing page lists Advanced, Expert, and Enterprise tiers by quote, with unlimited estate plans and document creation included. Expert adds Estate Builder and AI-assisted abstraction; Enterprise adds controls and workflows for larger teams.
In September 2025, Vanilla also announced Starter, aimed at boutique advisory firms, with pricing planned from $99 a month. That is an announced entry offer from that period, rather than a published price for today’s full platform. Optional services and legal engagements also deserve attention when a firm estimates its total bill.
Investors have financed the expansion: Venrock led the announced $11.6 million Series A in 2021, Insight Partners led a $30 million Series B in 2022, and Vanilla confirmed a further $35 million round in October 2024. Michael Jordan joined the Series A. His presence is memorable; the recurring advisor workflow is what the business has to earn.
05 The next question may come from the software
Vanilla’s September 2026 announcement identifies another obstacle: an advisor who lacks estate knowledge may not know what to ask an AI assistant. Its proposed next generation of VAI would surface discrepancies and planning opportunities across an advisor’s client book. General availability was scheduled for later in 2026. The advisor would decide what to act on.
The practical lesson travels beyond finance. Make the consequences of a complicated decision visible, then give people a reason to revisit it. That depends on current information, a willing advisor, and appropriate legal help. A diagram cannot sign a will or fund a trust. It can, however, make the unfinished work much harder to overlook.