About Barry Brooks
My name is Barry Brooks and I've spent the last 30+ years building tools, platforms, and businesses on the internet.
Every major technology wave creates the same problem: the people who need it most understand it least. I've been closing that gap since the 1990s, when I was privately training senior executives on K Street who didn't want their teams to know they weren't comfortable using a computer. The technology changes. The gap between what's possible and what business owners can actually access stays the same. That's the gap I fill.
Today, I run Annapolis.ai, where I serve as a Fractional AI Officer for small and mid-sized businesses. That means I set AI strategy at the executive level and build the actual systems myself. I deploy autonomous AI agents that handle real business operations. Not chatbots that answer questions, but production systems that do real work. I build and operate these systems every single day.
What makes me different from most AI consultants is straightforward: I've been a builder my entire life. I don't hand you a strategy deck and walk away. I build the systems, deploy them into your operations, and make sure they deliver results. I've been doing that since the 1990s.
How I Got Here
1994
The PC Edge, Inc.
Washington, DC | 21 years
My first company. I founded The PC Edge as a computer consulting, training, and software development firm serving DC's K Street corridor. Over two decades, I worked with Fortune 500 companies, think tanks, political organizations, and a US congressman and staff. I even consulted once at the White House.
One detail from those years has stayed with me. Senior executives frequently brought me in privately because they didn't want their teams to know they were unfamiliar with the technology they were expected to use. That same dynamic is playing out today with AI. The PC Edge reinforced the principle that still drives my work: the most valuable thing in technology is taking something complex and making it accessible for the person who needs it.
1997-2005
Building the Early Internet
During the late '90s and early 2000s, I launched a string of internet businesses that caught waves before they broke. VirtualServer.com was one of the first virtual hosting companies. I was offering shared hosting before most people knew you could put a website on someone else's server. The client base was acquired by a large publicly traded hosting company. 24-7DomainRegistration.com automated domain registration when the process still required submitting a form by email and waiting weeks. It grew to over $50,000/month in revenue within months, run from a one-bedroom apartment in DC. I also began investing in domain names during this period, eventually completing hundreds of transactions.
1999-Present
BetterWhois.com
I built BetterWhois.com in a single weekend. It became the first universal domain search tool in the newly deregulated domain name system and ranked in the top 0.1% of most-trafficked websites on the entire internet.
The tools I built during this period were cited in more than 100 books and publications worldwide. CEH Certified Ethical Hacker exam guides (six editions), multiple "For Dummies" books, Microsoft's Encyclopedia of Security, The Lawyer's Guide to Fact Finding on the Internet, Reader's Digest, and multiple United States Congressional Hearings. I also built LinkPopularity.com, an SEO backlink analysis tool cited in 40+ additional publications including PC Magazine and the OECD.
2008
CancelCable.com
In 2008, I realized my family was spending almost $2,000 a year on cable TV, and most of what we watched was available online for free. So I built CancelCable.com and a tool called "Showfinder" that helped consumers find TV content available online.
ABC's Good Morning America picked it up. Then the Washington Post. Then TechCrunch, PBS, LA Times, MSNBC, ABC News, the Dallas Morning News, and MSN MoneyBlog. I was predicting the death of cable TV well before "cord-cutting" became a household term.
2015-2023
Digital Marketing and Automation
I built WebsitePromotion.com into a full-service digital marketing consultancy. SEO, paid media, influencer marketing, and e-commerce consulting for Shopify merchants. This period deepened my understanding of how owner-operated businesses actually work day to day.
As AI tools began emerging, I was already deep in process automation, building complex workflows in Zapier, Make.com, and N8N, connecting business systems that were never designed to talk to each other, and developing outreach infrastructure across platforms like Klaviyo, Mailchimp, and Instantly.ai. That hands-on automation experience became the foundation for much of what I build with AI today.
2023-Now
The Rise of AI Agents
I started experimenting with AI marketing tools before ChatGPT launched in November 2022. Initially the applications were straightforward: marketing copy, ad creative, content generation. Useful, but limited.
As the technology matured, I went from using AI as a writing assistant to building AI systems that operate autonomously. Today I specialize in agentic automation, working with Claude Code, Manus, OpenClaw, and Perplexity Computer to build production AI systems that handle real business operations. The shift from "AI that helps you write" to "AI that does work for you" is the most significant technology transition I've seen since the early internet.
100+
Books & Publications Citing My Tools
9+
Major Media Outlets Featuring My Work
30+
Years Building on the Internet
Good Morning AmericaWashington PostTechCrunchPC MagazinePBSABC NewsLA TimesMSNBCDallas Morning News
Over 30 years, Barry's tools and ventures have been cited in 100+ publications including Microsoft, Wiley, Reader's Digest, and the OECD - and covered by major media from Good Morning America to TechCrunch.
Beyond the Terminal
When I'm not deploying AI systems, you'll find me sailing on the Chesapeake Bay or teaching or practicing yoga in Annapolis.
I live in Annapolis, Maryland, one of the best small cities in America and a place where the water is always close. I believe the best technology is the kind that gives you more time to enjoy your life, not less. That's exactly why I build AI agents that work like trusted virtual employees: they handle the operations so you can spend more time doing what matters to you.
Whether that's growing your business, being with your family, or getting out on the water, the point is the same. AI should give you your time back.
Want Me on Your Team?
Book a strategy session and let's figure out where AI fits in your business. Honest assessment. Specific recommendations. No pressure.