This as-told essay is based on a conversation with Matt Blumberg, a four-time tech CEO who now leads Markup AI, creator of an AI platform designed to help brands safely scale AI-generated content. He is based in New York. This story has been edited for length and clarity.
Since I run an AI company, I try to create AI agents and use AI as much as possible. In October, I got the idea to build what I call a fantasy board from another CEO, and with his permission, I created my own version to use as a personal thinking partner.
We have a real human board, and it’s fantastic. I get very good advice from them. But I wanted to use AI to create a fantasy board because mine is limited by the five people in it and the experiences they have in life.
So the first thing my management team and I did was create a fantastic draft. It’s a bit of a play on fantasy football and fantasy basketball. But instead of it being a competition, where each of us would recruit our own teams, we selected just one together.
We started by creating a spreadsheet of mostly famous people, largely but not entirely, from the business world. We’ve divided them into categories, including iconic business leaders, tech CEOs, venture capitalists, authors and thought leaders. We also had a category for different voices, like Oprah Winfrey and Taylor Swift.
Then we had something like a draft where we selected a few people from each category that we wanted to be on the board. We selected around fifteen names, including Warren Buffett, Steve Jobs and Oprah Winfrey.
There are also two people I know. One of them is me. The other is Fred Wilson, a VC I’ve worked with for 25 years at other companies.
From there, we asked the AI to create 5,000-word profiles for each person, and we gave it a certain template to follow. We wanted the imaginary board members to be able to respond to things the way real board members would, with real things they said about the performance of companies and boards.
Next, we built the agent. We loaded up all of these profiles and then wrote a very long set of instructions about what we were trying to accomplish and what our company does. We also uploaded documents from previous board meetings, our quarterly business reports, and other items that real board members would have at their disposal or in their heads.
This all lasted maybe an hour or two.
So now the fantasy board exists and I use it as a thinking partner. For example, I will provide a draft of a board book before sending it to my current board, and I will say: These are documents for an upcoming meeting. What do you think of them? Are there any topics you would have expected from me that I didn’t cover? What questions am I likely to receive from our board? In return, I will get really useful feedback.
One thing we put in the set of instructions is that when I ask for the board’s opinion, in a very generic way, I want them to give me the consensus opinion and notable marginal dissents with quotes of things that fantastic board members have actually said.
I will also ask him for help on internal projects. I’ll say things like: Hey, I’m presenting for our kickoff meeting next week. What do you think are the three main themes I should cover?
Recently, I asked my fantastic board of directors to give me a performance review for 2025. They succeeded. The board pointed out the things I would have called my strengths and the things I would have called my problems. I sent the assessment to my management team just for information, and they all came back to me and said it was pretty impressive.
I don’t use the fantasy board every day, but I probably use it at least every two weeks for something. There are two major limitations.
The first is that anything agentic is only as good as its inputs. My fantasy board only knows what I’ve told it about my business or what’s publicly available. He doesn’t really know what happens on a daily basis in the company. Even though I’m pretty good at feeding him information, he just doesn’t have all the context.
The other limitation is that they are not real people. When you have a true board of directors, you have a true thought partner as a strategic advisor. If you have a board meeting, people are in a room together. They have body language. They have facial expressions. You can tell when they lean in, when they lean back. You can tell when they roll their eyes because they don’t believe what you’re saying. You can ask them about this.
With all AI agents, you have to be very careful not to believe bullshit. They are predictive and good, but not perfect. They are not human and lack many signals.
I told my real board about my fantasy board at our last meeting, which took place in November, right after it was built. I explained what it was and how I used it. They thought it was great. A few of them then asked me how I built it. They asked for a road map and said they would like to do something similar.
They saw the fantasy board the same way I did, that it is a nice addition, a sort of augmentation of thought partnership, but it will never replace a real board.