This told essay is based on a conversation with Matt Blumberg, a four-time technology CEO who now leads Markup AI, a maker of an AI platform designed to help brands securely scale AI-generated content. He is based in New York City. This story has been edited for length and clarity.
I run an AI company, so I try to build AI agents and leverage AI as much as possible. In October, I received the idea from another CEO to build a so-called fantasy board, and with his permission, I created my own version to use as a personal thought partner.
There’s an actual human board, and it’s great. I’m getting really good advice from them. But I wanted to use AI to create a fantasy board. Because my board is limited by the five people on it and what they’ve experienced in life.
So the first thing my management team and I did was create a fantasy draft. It’s a spin on fantasy football and fantasy basketball. But it wasn’t competitive, each of us drafting our own team, we only drafted one team together.
We started by creating a spreadsheet of essentially, if not all, famous people in the business world. We categorized them into categories such as iconic business leaders, technology CEOs, VCs, authors, and thought leaders. There were also categories for different voices, including Oprah Winfrey and Taylor Swift.
Then there was something like a draft where we picked a few people from each category that we wanted to put on the board. They settled on about 15 names, including Warren Buffett, Steve Jobs, and Oprah Winfrey.
Two people I know are also participating. One is me. The other guy is Fred Wilson, a venture capitalist who I’ve worked with for the past 25 years at other companies.
From here, we had the AI create a 5,000-word profile for each individual and gave it a specific template to follow. We wanted fantasy board members to be able to react in the same way as real board members, with real-life statements about company and board performance.
Next, we built the agent. We loaded up all these profiles and wrote a very long set of instructions about what we were trying to accomplish and what our company did. We also loaded materials from past board meetings, quarterly business review materials, and other materials that actual board members have at their disposal or in their heads.
All of this probably took an hour or two.
So now the fantasy board exists and I use it as a thought partner. For example, provide a draft of the board book before sending it to the actual board and say: “These are materials for future meetings.” What do you think about them? Are there any topics you expected me to cover that I didn’t? What questions might I get back from the board? In return, you’ll get some really helpful commentary.
One of the things that we put in our instruction set is that very commonly when we ask boards for their opinion, we want them to quote what fantasy board members have actually said and tell us what the consensus and notable outliers are.
We also ask for your cooperation in internal projects. Say something like: “Hey, I have a presentation for the kickoff meeting next week.” What do you think are the top three topics I should address?
I recently asked Fantasy Board for a 2025 performance review. It was perfectly accurate. The board of directors pointed out what I thought were strengths and what I thought were problems. I sent this review to management for reference and they all came back and said it was very impressive.
I don’t use my fantasy board every day, but I think I use it for something at least every other week. There are two major limitations.
One is that an agent is only as good as its inputs. My fantasy message boards only know what I talk about about my business or what’s available to the public. In fact, you don’t know what’s going on at your company every day. It’s pretty good at giving information, but it doesn’t have all the context.
Another limitation is that they are not real people. When you have a real board of directors, you have real thought partners as strategic advisors. If you have a board meeting, people are in the same room. They have body language. They have facial expressions. You can tell when they lean in and when they lean back. You can tell when they roll their eyes because they don’t believe what you’re saying. You can call them out on it.
When using AI agents, you must be very careful not to believe bullshit. They’re predictable and good, but not perfect. They’re not humans, so they miss a lot of cues.
I told the real board about my fantasy board at our last meeting in November, right after it was built. I explained what it is and how I used it. they thought it was great. Later some people asked me how I made it. They asked for a roadmap and said they wanted to do something like that.
They thought of fantasy boards the same way I did. So, while it’s a nice add-on and enhances your thinking partnership, it’s by no means a replacement for the actual board.