Haven't made a will yet? startup has new AI tool to help
Barbo is the CEO of Trust & Will, a San Diego company that simplifies the creation of estate planning documents by drafting documents with its lawyer-vetted software.
Eight years later, Barbo is married and his family has grown.
So has his company. Trust & Will, based in San Diego's Bankers Hill, has helped more than 1 million families make estate plans, Barbo said in an interview from his Dallas home office.
"Normally you pay thousands of dollars up front to do this with an attorney, or hundreds to thousands of dollars for those updates, for that ongoing guidance," he said. "This is the democratization of estate planning."
It has raised more than $80 million from venture capital and corporate investors including Moderne Ventures, American Express, AARP and Northwestern Mutual. Last year, the company became "cash-flow positive," startup speak for hitting profitability, and then secured a Series C round of capital this year. It employs around 110 people, up from around 80 in 2023.
And last week, it announced the launch of a new AI-powered platform called EstateOS, which Barbo says will make estate planning even easier, more efficient, more personalized and more broadly accessible. It also turns Trust & Will - one of several companies that digitally create estate plans - into what Barbo says is "the first company to launch an AI-integrated estate planning platform at scale, specifically designed for both consumers and financial professionals. While others may be experimenting with AI, EstateOS is the first comprehensive system combining Trust & Will's proprietary estate planning software with embedded OpenAI-powered tools to streamline creation, review, and updates of estate plans."
New tools, an AI boost
Using proprietary software and OpenAI, EstateOS delivers four features that are "intelligent upgrades of previously manual or slower processes," Barbo said, who co-founded the company with Daniel Goldstein and Brian Lamb.
Some of the new features will appeal to U.S. consumers - only 31% of which have a will, according to a company survey of 10,000 people - and others will appeal to the company's industry targets: financial planners, life insurance agents, nonprofits and attorneys, he added.
One feature, called PlanScore, does what its name suggests: It "scores" estate plans with a rating system that helps customers find blind spots and figure out where their estate plan needs buttressing.
Another is an AI assistant that lets users ask questions and have the answer served instantly. Instead of digging around to find out who was named as a guardian, Barbo said, you can ask who the guardian is and get reminded that it is your mother-in-law.
A third feature is document extraction, which will summarize and mine user-submitted documents for useful or actionable data and workflows. This could be especially useful for people who have drawn estate plans that are "just sitting in a box in the closet."
The last feature streamlines communication - and client prospecting. The "Connected Networks" tool brings together parties connected to an account, including executors, beneficiaries, attorneys and financial advisers, into a shared platform. That can make deed transfers and notarized transactions run more smoothly, and also make it easier for those professionals to build their contact lists.
Down the line, Barbo said a fifth service will keep track of life's seismic events, the kind where an estate plan update could make sense, such as marriage, divorce, a new baby, a home purchase - and alert users when they should amend something.
Pricing to create a will or trust remains the same. An individual's will-based plan starts at $199 and a trust-based plan starts at $499. Couples are charged an extra $100, and updates cost extra. Optional memberships at different pricing tiers give access to the EstateOS and other features. Attorney support is included in some plans or can be purchased as an add-on.
The estate planning startup's plans
For its first eight years, Trust & Will was one of several in a crowded digital legal document and estate planning marketplace, all of which turned estate planning from a costly investment to something that could be scratched off one's to-do list with a few clicks and a spare hour. LegalZoom and Rocket Lawyer are the bigger names, but there's also WillMaker.com and the company that would win wittiest estate planning domain name, if that were a thing - FreeWill.com.
The National Council on Aging recommends these online tools, saying "If an attorney isn't in your budget, an online will-making service can be a good alternative." Among the five companies it recommends, Trust & Will is crowned "most user-friendly."
In estate planning, the use of AI is a topic of interest for attorneys, according to the American College of Trust and Estate Counsel. A free video series explores practical and ethical issues around generative AI in estate planning. "Resistance to the coming of AI is futile," one speaker, a law professor, said last year. Lawyers, he added, "should keep abreast of the changes in the law and its practice, including the benefits and risks associated with relevant technology. So accordingly, you have an obligation to yourself, your clients, and the profession to become acquainted with and proficient with the use of AI in your estate planning practice."
Barbo's 2017 pitch to investors succeeded: His company won $5,000 in seed money. Today he is eyeing the biggest prize for a startup - to take the company public.
Copyright (C) 2025, Tribune Content Agency, LLC. Portions copyrighted by the respective providers.
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