Almost everyone knows they should have a will. Almost no one wants to spend an evening and a few thousand dollars in a lawyer's office to make one. So they put it off, year after year, and roughly seven in ten adults end up with none. The cost of that delay never lands on the person who delayed. It lands on the people they leave behind, who inherit not only grief but a tangle of frozen accounts, unanswered questions, and, often enough, a fight over what was never written down.

David Rosati watched this play out from the inside. He spent fifteen years as a corporate and mergers and acquisitions lawyer, and his wealthy clients paid well for complicated estate work. Their friends and families kept asking him for the same small favor, a basic will, and it struck him that most of them were paying for a bespoke experience they did not need. He built Succession Wills to give that majority a real will without the lawyer's bill or the lawyer's calendar.

In this episode of Lead with AI, Dr. Tamara Nall speaks with David Rosati, Co-Founder & CEO, about the design choice that separates Succession Wills from the wave of AI will generators, why most people's estates are simpler than they fear, and where the platform goes once the will is written.

The part of a will everyone gets wrong  

Most people picture a will as a document. A lawyer pictures it as two jobs. The first is the conversation, the hour where a good lawyer asks questions the client never thought to ask, explains ideas the client did not know existed, and turns a vague intention into a clear set of decisions. The second is the drafting, where those decisions become valid legal language.

Will kits and online builders only ever sold the second job. They hand you a stack of forms and a row of toggles and assume you already know what you want. For the roughly seven in ten adults who have no will at all, that assumption is the whole problem. They are not avoiding a form. They are avoiding a conversation they do not know how to have.

So the AI is barred from the document  

Here is the line Succession Wills draws, and it is worth saying plainly.

The AI never writes the will.

It runs the interview instead. It understands the structure of the will underneath, it knows which decisions still need answers, and it draws those answers out of you in language a non-lawyer can follow. When it has what it needs, a separate deterministic engine produces the document, an engine in which every sentence that can possibly appear was written and approved in advance by Rosati himself. No model generates legal language on the fly. There is nothing to hallucinate about because the AI is not holding the pen.

That matters more than it sounds because it answers the exact warning every estate lawyer gives about AI wills. The danger people are told to fear is a model improvising legal text, inventing clauses, and handing back a document that looks finished and would collapse in court. Succession Wills removes the model from that step and keeps a lawyer's judgment on every line. Rosati is upfront that he could have shipped the other version, a chatbot trained on wills with a thin interface, in a fraction of the time. He refused. A will is someone's family and someone's livelihood, and that is not a place to find out your software guessed.

What it actually feels like to use  

The product runs on a toggle. Some people know exactly what they want and would rather click through a wizard. Others need to talk it through. Succession Wills lets you switch between the two inside one login, mid-process, without losing your place. Move through the form for the parts you understand, flip to the AI when a question makes you pause, and the AI already knows everything you have entered and everything still missing.

Starting costs nothing. You can build the entire will, watch it assemble in a live preview, and only meet a paywall at the very end. No card is required to find out whether the thing works. Rosati and his co-founder Nick, the developer behind the build, run the company bootstrapped, and when you email support, one of them answers.

A lawyer who would not ship until it was right  

The build took time, and Rosati owns the reason. The startup instinct is to release something rough and improve it in public, to build the parachute on the way down. A lawyer is trained on the opposite instinct, that nothing leaves the office until it is correct. So the team spent months on the slow, exacting part, the deterministic engine where every sentence had to be vetted, before the product ever met a customer.

The AI layer, by contrast, went in fast, and that gap is what surprised him most. Adding a conversational interview onto a finished, correct architecture took a fraction of the effort the architecture itself demanded. There was a second surprise watching his co-founder work, an experienced developer using Claude Code as rocket fuel, building one AI with the help of another.

Where Succession Wills goes after the will  

Writing the will, Rosati points out, is only the opening move. When someone dies, a person named in that will has to step into their life and run it, and that person usually has no idea where the accounts are, what assets exist, or the password to the email they suddenly need to get into. The plan for Succession Wills is to hold all of it in one place, the will, the asset list, the logins, and the practical details a family otherwise scrambles to find at the worst possible moment. Once that information lives in one system, planning the estate, growing it, and eventually settling it all become possible from the same place. The will is the front door, not the house.

Quick Answers  

Can AI write your will? A general AI tool like ChatGPT can produce something that looks like a will, but estate professionals widely warn against relying on it, because it can invent clauses, miss the formalities that make a will valid, and apply the wrong jurisdiction. Succession Wills takes a different approach. The AI runs the interview, and a deterministic, lawyer-approved engine produces the actual document.

Does the AI at Succession Wills draft the will? No. The AI only handles the conversation and maps your answers. Every sentence that can appear in the will was written and approved in advance by a lawyer, so the document does not depend on a model generating legal text.

How much does Succession Wills cost? You can create an account and build a complete will for free, including a real-time preview. Payment is only required at the end of the process.

Who is Succession Wills for? It is built for the large majority of people whose estates are straightforward, a spouse, children, a home, and some savings, who do not need an expensive bespoke lawyer but still want a properly considered, valid will.

Who is David Rosati? David Rosati is the Co-Founder & CEO of Succession Wills. He practiced corporate and mergers and acquisitions law for fifteen years before building the platform with his co-founder Nick.

If you have been putting off your will because the lawyer's office felt too expensive and the AI shortcuts felt too risky, Succession Wills was built for exactly that gap. You can start free at successionwills.com and only pay once the document is ready.

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