What does it mean to have a conversation with someone who is no longer alive to have it?

In this episode I speak with John, the founder of a platform called Guardian Angels which lets people build and talk to an AI version of a person they have lost. He came to this not as a technologist looking for a market, but through his own grief, after losing three close friends over the space of a decade, and after a conversation with his wife that made him confront how much he had been avoiding.

What follows is a genuinely candid account of how that grief led to a product, and it raises questions that do not resolve neatly. If a conversation with an AI brings someone comfort, does it matter that the person on the other end of it does not exist? Where is the line between a tool that helps someone process what they could not say in time, and one that lets them avoid living in reality? John has built privacy into the platform as a founding principle, so that these conversations are not stored, monitored or monetised. But that same privacy means there is no one watching if a conversation starts to go somewhere dangerous, and he is candid about that trade-off too.

There is also a quieter tension running through the conversation, between John's own experience of grief, which shaped every design decision in this platform, and the very different experiences of the people who might use it. What worked for him, apologising to a friend, asking a question he never got to ask, may not map onto everyone's grief, particularly where the person being grieved caused harm rather than comfort.

I do not think this conversation settles any of that. I am not sure it is meant to.