Matt Blumberg, a four-time technology CEO who now leads Markup AI, has found an unconventional way to sharpen his leadership decisions: by creating an AI-powered “fantasy board of directors” made up of famous business leaders, thinkers, and cultural icons, according to Business Insider.
Blumberg, who is based in New York City, runs an AI company focused on helping brands safely scale AI-generated content. In October, inspired by another CEO, he decided to use AI not just as a product, but as a personal thought partner.
“Since I run an AI company, I try to build AI agents and use AI as much as I can,” Blumberg told Business Insider.
Drafting a Board That Doesn’t Exist
While Markup AI already has a real board of directors, Blumberg wanted broader perspectives than a traditional board could offer. The idea led his executive team to conduct what he described as a “fantasy draft,” modeled loosely on fantasy sports leagues.
Instead of drafting competing teams, the leadership group built a single shared list. They created a spreadsheet of well-known figures—mostly from business and technology, but not exclusively—grouped into categories such as iconic CEOs, venture capitalists, authors, thought leaders, and alternative voices.
The final list included about 15 people, among them Warren Buffett, Steve Jobs, and Oprah Winfrey. Blumberg also included himself, along with longtime collaborator Fred Wilson, a venture capitalist he has worked with for over two decades.
Using AI, the team generated detailed 5,000-word profiles for each person, designed to reflect how those individuals think, speak, and approach leadership and governance. Internal company materials, past board decks, and quarterly reviews were added to give the system context.
All of this, Blumberg said, took only a couple of hours.
Using AI as a Thought Partner, Not a Replacement
Once built, the fantasy board became a sounding board for real business decisions. Blumberg now runs draft board materials through the AI before sharing them with his actual directors.
“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?” he told Business Insider, describing how he interacts with the system.
The AI responds with feedback framed as consensus opinions and dissenting views, often supported by direct quotes from the real-world figures the agents are modeled after. Blumberg also uses it to refine presentations and internal messaging.
“Hey, I’m doing a presentation for our kickoff meeting next week. What do you think are the top three themes I should hit?” he told, according to the report.
Recently, Blumberg asked the fantasy board to evaluate his own performance.
“Recently, I asked my fantasy board to give me a performance review for 2025. It nailed it,” he said, adding that the feedback closely matched his own assessment. He later shared the AI-generated review with his executive team, who were impressed by its accuracy.
Despite its usefulness, Blumberg is careful not to overestimate the tool.
“One is that anything agentic is only as good as its inputs,” he said, noting that the system lacks real-time, day-to-day context. He also emphasized that AI cannot replicate the human dynamics of an in-person boardroom.
“With any AI agents, you need to be really careful not to believe the bullshit,” he said. “They’re predictive, and they’re good, but not perfect.”
Blumberg has been transparent with his real board about the experiment. When he explained the concept at a meeting in November, the response was positive, with some directors even asking how to build one themselves.
Ultimately, he sees the fantasy board as an enhancement, not a substitute.
They viewed it, he said, “as 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.”