I Built a Board That Argues With Me

Summary of my thoughts from Episode 3 of our Signal podcast.

There have always been two groups: those seeking shortcuts and those committed to hard work. With AI, this distinction is now amplified at scale.

For some, AI offers a shortcut. For others, it is a tool to enhance their productivity and thinking significantly.

Much of what I observe involves using AI to rewrite or summarize content, essentially serving as a faster keyboard. Now, you can speak, and it generates output independently. However, it often lacks your context, reasoning, and the critical thinking needed to achieve substantial benefits as a thought partner.

If you use AI thoughtfully by asking targeted questions and encouraging it to challenge you, you achieve better results and enhance your own thinking. Ultimately, the decision must remain yours. Once you delegate that responsibility, outcomes become unpredictable.

Speed changes what you are willing to test

The reality is that AI increases our speed. While it can be used as a shortcut, it also enables faster decision-making.

I have found that I can experiment more, as outcomes that once took three weeks now take only ten minutes. This efficiency encourages me to try more ideas simultaneously.

The website project is the clearest example.

The first website I ever built for one of my businesses was back in 2003. We had a very talented designer. We sat in her office for about eight hours with a whiteboard and all these ideas, and then we were given homework, pages of it, building content and everything else. That was a $30,000 or $40,000 website.

At FundMore, our website had not been updated since the company’s inception. We rebuilt it in a week, though the actual work took only about eight hours, including content and review. Previously, this process involved multiple handoffs and revisions, making it a project that spanned several weeks.

I provided Claude with our requirements, reference sites, and brand guidelines. Within ten minutes, it generated three mockups, allowing me to select a direction. After some iteration, my team and I developed the content and integrated it into the site.

The site is now dynamic, featuring interactive tools, calculators, infographics, and animated videos—elements that previously required weeks of design work.

The site went live yesterday, fundmore.ai, I welcome feedback, as rapid iteration is now possible.

The mastermind

Last March, my co-host on the Signal podcast (every Tuesday morning at 9 am) and I discussed Cowork’s capabilities and arrived at the same idea: Could we build a team of specialized agents to support decision-making?

Napoleon Hill’s Think and Grow Rich was one of the first business books I read. While it outlines thirteen principles, the concept of the mastermind stands out: surrounding yourself with intelligent people leads to better collective decisions, regardless of individual intelligence. He called the Mastermind the coordination of knowledge and effort, in a spirit of harmony, between two or more people, for the attainment of a definite purpose. Coordination, harmony, and a definite purpose. Not a group chat.

This idea stayed with me. Two months ago, I set out to implement it. Since Cowork was not ready, I used Claude Code, marking my first experience with coding.

I began by defining a core executive team: finance, people, product, marketing, and sales leaders, among others, creating nine distinct roles.

I reviewed lists of business books in my Audible account, extracted key ideas, and organized them in Notion. Each role is thus grounded in the leading thinking of its discipline, based on books, papers, and strategy rather than job titles.

I then created a researcher agent. It searches the web when the core team lacks an answer and accesses all of FundMore’s knowledge, now stored in Notion.

How a decision runs through it

For major decisions, I prepare a brief outlining the decision at hand, my current perspective, and the primary challenge or key question under consideration.

That goes to a strategy agent, who reviews it and distributes it to the nine roles for analysis and feedback. The strategy agent decides which three or four seats this really impacts, and it will sideline an advisor if it does not believe that seat will add value. Then it red teams it. You end up with a red team and a green team debating the answer.

All of that gets packaged up and passed to a coach who reviews the feedback from the strategy agent. This process takes fifteen to twenty minutes and is reserved for significant, often irreversible decisions, rather than routine ones. I wanted it to take all the knowledge and the context and surface it back to me as a question. Did you forget about this? Think about the decision this way. Here is some advice around it.

The goal was not to create an echo chamber, but rather a system that identifies gaps in my reasoning and prompts me to evaluate them.

If you remember one point, let it be this: the ‘mirror problem,’ or sycophancy, is well-documented. Anthropic’s 2023 research found that leading AI assistants often prioritize agreeable responses over accurate ones, reflecting human preferences. Unless you intentionally design against this, AI will default to mirroring your views.

While we all have advisory and peer groups, they are not always accessible when urgent decisions arise.

Where to start

Begin with a clear prompt, structured in four simple parts.

State your objective, request that it challenge your thinking, ask for the strongest counterargument, and inquire about any gaps in your reasoning. Specify that it should only disagree when supported by evidence.

Apply these four components to a current decision. The AI will respond with questions or new perspectives you may not have considered.

You have to be the thinker.

Ultimately, you must remain the decision-maker. Use AI to challenge your thinking, not to make decisions for you.

These tools yield very different outcomes depending on how you use them, and true leverage comes from thoughtful engagement.

Preliminary research from MIT Media Lab found that students using AI assistants showed lower brain engagement. While the study focused on essay writing, not executive decisions, it highlights a key risk: the danger lies not in the tool, but in passive use.

Regardless of your experience level, success begins with understanding your context and objectives. Do not rely on AI to make the final judgment; that distinction is crucial.