MattBot: My First Agent

In May 2023, Fred Wilson wrote a post about being approached by a company that had trained a large language model on all 9,059 of his AVC blog posts. They wanted to offer a chatbot called “Ask Fred.” He said no thanks.

His reasoning was sharp. He’s fine with anyone using his content to train AI. He put a Creative Commons license on his blog from the start. But he didn’t want a bot pretending to be him. The whole point of his blog is the humanity — the daily conversation, the thinking out loud, the relationship with readers. A chatbot that mimics Fred Wilson isn’t Fred Wilson. It’s a parlor trick.

I read that post and agreed with Fred completely. An AI version of me that replaces me? No interest.

But an AI version of me that helps me be more productive while keeping my voice and point of view? That’s a different story entirely.

Building MattBot

MattBot is a custom agent I built inside Chatgipity, our company’s internal AI platform. It’s not a gimmick. It’s one of the most useful tools I’ve ever created.

Here’s what’s under the hood:

• My complete body of writing. Every blog post from 20+ years of StartupCEO.com. My three books — Startup CEO, Startup Boards, and Startup CXO. My eBooks. Podcast transcripts from over 200 episodes. Conference talks.
• My email and Google Drive. So it has context on what I’m working on, who I’m talking to, and what’s current.
• A detailed map of what to include. I didn’t just dump content in. I created a structured guide for the agent — what topics I cover, what my positions are, how I frame arguments, what language I use and don’t use.

The result is an agent that doesn’t replace me. It accelerates me. It knows how I think, how I write, and what I’ve already said about many topics in entrepreneurship and leadership.

How It Saves Me Time

Let me give you some real examples.

A college kid I used to coach in baseball reached out recently and asked to interview me for his freshman entrepreneurship class. I always say yes to these — it’s important to me to help young people who are curious about building things. But historically, that’s a 90-to-120-minute commitment: time to think about the questions, time to write thoughtful responses, time for follow-ups.

This time, I asked him to send me the questions ahead of time. I fed them to MattBot. In 30 seconds, I had draft responses that were substantively right and sounded like me. I spent five minutes editing them, sent them back, and then spent 15 minutes on follow-up questions. Total time: 20 minutes instead of two hours. Same quality. Same voice. Same care.

Preparing for podcast appearances used to take me 30 minutes of reviewing the host’s questions, thinking about framing, jotting notes. Now it takes 30 seconds — MattBot drafts my talking points based on what I’ve already written and said about those topics, and I review and adjust on the fly.

Taking a generic output from any LLM and “Matt-izing” it takes 30 seconds. The upstream work on the LLM might save hours, but the only reason the final product works is that MattBot refines it with my language, my voice, and a high percentage of my long-term body of knowledge.

How the Company Uses It

This is where it gets even more interesting. MattBot isn’t just for me.

Marketing or our PR firm can hand me bullet points for an article or a LinkedIn post, and I can have MattBot do a first draft in 30 seconds. I review it, tweak it, and send it back. What used to be a multi-day back-and-forth is now an instantaneous turnaround.

Better yet, I published the agent to two colleagues in Marketing so they can use it directly. They can draft thought leadership content in my voice without waiting for me to be available. I still review everything — that’s non-negotiable — but the bottleneck is gone.

The Flywheel

Here’s what makes MattBot different from a one-time prompt or a static set of instructions: I treat it like a living system.

Every time I review a response and make edits, I feed those edits back in and tell the agent to learn from them. Any time I write something new — a blog post, an article, an email that captures how I think about a topic — I feed it in. Every new podcast transcript goes in.

So MattBot keeps getting better over time. It’s not a snapshot of who I was when I built it. It’s an evolving representation of how I think and communicate right now.

Fred was right to say no to “Ask Fred.” But I think he’d appreciate what MattBot actually is: not a replacement for humanity, but a tool that gives me more time to be human.