This as-told-to essay is based on a conversation with Matt Blumberg, a four-time technology CEO who now leads Markup AI, maker of an AI platform designed to help brands safely scale AI-generated content. He is based in New York City. This story has been edited for length and clarity.
Since I run an AI company, I try to build AI agents and use AI as much as I can. In October, I got an idea to build what I call a fantasy board of directors from another CEO, and with his permission, I made a version of my own to use as a personal thought partner.
We have an actual human board, and it’s fantastic. I get really good advice from them. But I wanted to use AI to create a fantasy board because mine is limited by the five people who are on it and the experiences that they have in life.
So the first thing my executive team and I did was create a fantasy draft. It’s a bit of a play on fantasy football and fantasy basketball. But instead of it being a competitive thing, where each of us would draft our own teams, we drafted just one together.
We started by making a spreadsheet of essentially famous people, largely but not entirely, from the business world. We divided them into categories, including iconic business leaders, tech CEOs, VCs, authors, and thought leaders. We also had a category for different voices, such as Oprah Winfrey and Taylor Swift.
Next, we had something like a draft where we picked a couple of people from each category that we wanted on the board. We settled on about 15 names, including Warren Buffett, Steve Jobs, and Oprah Winfrey.
There are also two people on it that I know. One is me. The other is Fred Wilson, a VC I’ve worked with for the past 25 years at other companies.
From here, we had AI build 5,000-word profiles for each person, and we gave the AI a certain template to follow. We wanted the fantasy board members to be able to react to things as real board members would, with actual things they’ve said about how companies and boards perform.
Next, we built the agent. We loaded all these profiles in and then wrote a really long instruction set about what we were trying to accomplish and what our company does. We also loaded materials from past board meetings, our quarterly business review decks, and other things that real board members would have at their disposal or in their heads.
All of this took maybe an hour or two.
So now the fantasy board exists, and I use it as a thought partner. For example, I will provide a draft of a board book before sending it to my actual board, and I’ll say: These are materials for an upcoming meeting. What do you think of them? Are there topics you would have expected me to cover that I didn’t? What questions am I likely to get back from our board? In return, I’ll get really useful commentary.
One thing we put in the instruction set is that when I ask the board for its opinion, very generically, I want it to tell me the consensus opinion and notable outlying dissent with quotes of things that the fantasy board members have actually said.
I’ll also ask it for help with internal projects. I’ll say things like: Hey, I’m doing a presentation for our kickoff meeting next week. What do you think are the top three themes I should hit?
Recently, I asked my fantasy board to give me a performance review for 2025. It nailed it. The board called out the things that I would have said are my strengths and things that I would have said are problems. I sent the review to my executive team just as an FYI, and they all came back to me and said it was pretty impressive.
I don’t use the fantasy board every day, but I’m probably using it at least every other week for something. There are two big limitations.
One 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. It doesn’t actually know what happens every day in the company. Even though I’m pretty good about feeding it information, it just doesn’t have all the context.
The other limitation is that they’re not real people. When you have a real board of directors, you have a real 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 something you said. You can call them out on that.
With any AI agents, you need to be really careful not to believe the bullshit. They’re predictive, and they’re good, but not perfect. They’re not human, and they miss a lot of cues.
I told my real board about my fantasy board at our last meeting, which was in November, right after we built it. I explained what it was and how I’ve been using it. They thought it was great. A couple of them asked me afterward how I built it. They asked for a road map and said that they’d like to do something like it.
They viewed the fantasy board the same way I do, which is that it’s a nice add-on, a sort of augmentation of thought partnership, but that it’s never going to be a substitute for a real board.
Read the original article on Business Insider
The post I’m a CEO who built a fantasy board of directors with AI versions of leaders like Steve Jobs and Warren Buffett appeared first on Business Insider.
