The Family Office Agentic AI Roundtable
Spring 2026

AI is about to make the wrong answer arrive faster.

The principal cannot see across the structure. The institutional knowledge lives in someone's head. The custodial feed reports numbers without context.

That is fragmentation. The market thinks MCP solves it. It does not.

May 21 · June 4 · June 182:00 PM ET · 40 minutes each
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Why this matters now

Humans can navigate fragmentation. Agents cannot.

Senior operators have held offices together across fragmented systems for years. They know which spreadsheet is current. They remember what the trustee said in February. They call the CPA when something does not reconcile.

Agents do none of that. An agent pulling from fragmented systems will give you an answer that sounds confident — without the context that tells you whether it's right.

11 million views

Bill Ackman's X post on April 4 went public with the architecture problem this roundtable addresses. Every operator who read it saw their own office in the story — and the consequences. Protracted litigation. Staff turnover.

Three Roundtables

Three roundtables. From diagnosis to demonstration.

Thursday, May 21
2:00 PM ET · 40 minutes

Operating in the Dark.

Where family offices are right now — the principal who cannot see across the structure, the institutional knowledge in someone's head, the custodial feed reporting numbers without context. Where AI is right now — agentic, fast, accelerating. The gap between the two, and what closes it.

Thursday, June 4
2:00 PM ET · 40 minutes

The Architecture Test.

Every reporting platform in this market now claims agentic AI. The question stopped being whether vendors are claiming it. The question is which ones are real. Ten questions every family office should ask every vendor in their stack — and the same ten questions are the ten things you can explain to a principal or family member who asks what AI in our office means. Two audiences. Same architecture.

Thursday, June 18
2:00 PM ET · 40 minutes
Featuring Richard Reese Former CEO & Chairman, Iron Mountain

The Bottleneck Test.

A live demonstration on a real family office structure. Three trusts and one LLC. A capital call comes in, the trustee approves it on the principal's phone, and you watch the whole loop run from end to end. Richard Reese, who runs his office on iPaladin, joins to translate what you're watching.

Jill Creager
Founder & CEO, iPaladin
Thirty-two years as a fiduciary expert serving generational families with complex private wealth. Founded iPaladin to give those families the platform she wished she could have given them as their attorney.
Gene Diveglia
Chief AI Officer, iPaladin
Architect of AARK™, the AI layer running inside iPaladin. Co-inventor on iPaladin's pending AI patent.

Fix the architecture before the agents arrive.

Three Thursdays, starting May 21st.

Register for the Trilogy

Or read the resources we'll be working from: The Architecture Test · Why the work is still done by hand.