Who is Jesse Cunningham

I took computer science classes in high school. Front Page, Dreamweaver, a little bit of everything. I liked it, but I was not good at it. The kid next to me would solve a problem in 30 lines of code and mine took 500. So I figured out fast that I was not a coder. But the logic of it always made sense to me.

What I did have was an interest in money. I liked business. The interactions with owners and customers, all of it. Businesses needed an online presence and I could help with that.

My edge was the intersection of those two things, and it still is.

Out of high school I went to the University of Maryland for one semester and dropped out. Around that time I saw an ad on Craigslist for an idea: a local directory where businesses sign up and pay a monthly fee. Recurring revenue. I started one for my local area.

It went well at first. Within four or five months we had about 120 businesses onboarded. Then it lost wind and dwindled away. Call it young and dumb. Wanting money quickly is what killed it. If I did it again I would have onboarded every business in the area for free and charged advertisers to be on the platform.

For context, this was before Google listings were anything. Google Places did not exist yet and Google Business Profiles were years away. We were early.

It is funny to think that almost 20 years later, local and national directory websites are still hyper viable. Had I focused, that asset would still be producing today.

One more lesson from that business. We started an LLC before we had anything. We should have built the website first, gotten people on it, and then done all the things. Prove the thing makes money, then make it official.

After the directory died I was in that awkward phase of life at 20 years old with no idea what to do. So I got rid of literally every possession I owned and moved to the Big Island of Hawaii.

I was a carpenter at a lumber mill for a time. Then I landed one of the most sought after jobs on the island, real money at the time: $12 an hour at an insurance agency. I was very excited about that. The job taught me insurance, and I eventually brought that back to Maryland, built my own agency, and later sold it.

Hawaii gave me more than a trade. It is where I met my wife. We had three acres of off grid land, which was more affordable back then than you would think. We built a 400 square foot structure with solar and a 10,000 gallon catchment tank. You name it, it was wild. The property was surrounded by ohia trees with thick ferns climbing the trunks, so you were completely secluded. If you want to look into the area, check out Fern Forest, Hawaii. I highly recommend it.

The whole way through those years I was helping other business owners scale with websites, Facebook, and general marketing.

I have always had multiple sticks in the fire. People like Alex Hormozi say focus on one thing. I have a hard time doing that, and I have accepted that this is just how I am. I am going to have at least five projects going at any given time. That is kind of why YouTube started for me in the first place.

After I sold the insurance agency I was bored. I had some cash, felt good about that, and had no plan. Then this new thing called ChatGPT showed up and I started making videos about how it relates to SEO. Right place, right time. It resonated, and the channel got traction talking about AI strategies to rank a website.

During that run I built a website in public that reached hundreds of thousands of visitors per month. The videos are still on the channel if you want to go back and watch it happen. Then, during the Helpful Content Update, Google hit it with a manual penalty and deindexed the site. That is rare. It has only happened to a handful of SEOs who build in public.

The lesson: you can only give so much publicly before you get the ban hammer.

Some strategies are not viable to show on YouTube anymore. That is why we started Rank Expand Academy, a community on Skool focused on AI SEO, AI workflows, Claude Code, and whatever the models make possible next.

If you watch my recent videos, you will notice I talk about microsites a lot. The idea of having one website for your primary local business and nothing else is ridiculous nowadays. The better play is one primary website with satellite websites around the suburbs you serve. It is an easier way to rank for local business, it is very cost effective now that we have AI, and it is an absolute no brainer if done right. I think it is one of the most exciting things that most people do not do.

There are two primary ways to make money off of this:

• Rank and rentSell the leads that come off these websites on a flat fee or revenue basis.
• Rent the packageRent the whole set of sites out as a package.

You can also be the business owner yourself. I call that the star method, but there is too much to unpack for this bio section.

Most of what I am proud of lately is work I do not talk about on camera.

I am the head SEO for an international brokerage. When we started they averaged four leads a week. Now they get over 400, which has meant millions of dollars in added revenue for them.

That growth came in the middle of AI Overviews taking over Google, which has made things harder, no doubt. What we found is that the harder a question is to answer online, the more money there is in answering it. Plain informational content, the typical niche website playbook, does not work anymore. It used to be very easy. Now we infuse proprietary data into our blog posts and money pages so we can rank where generic content cannot.

For that same client we built a custom dashboard that pulls in all their Google Search Console data with an AI layer on top. Their team can have conversations with the data and make wise decisions about what to write and where to take the content next.

And for the last three or four years I have been the CMO for a local business, in charge of the entire marketing budget, scaling them from $10 million per year to over $15 million.

• My own websitesThe portfolio produces the majority of my revenue. I test everything here first.
• YouTubeVideos on what actually works, minus the strategies that get sites banned when shared.
• CMO workCMO for big international companies. Budgets of half a million dollars across websites, paid ads, direct mail, and billboards.
• The agencyRank Expand takes on clients that are a very good fit. We decline more than 90 percent of the people who ask to work with us.
• The academyRank Expand Academy, where the real playbooks live.

I have built SaaS along the way, always as an extension of the channel. When I need a tool that does not exist, I am more inclined to build it myself. What I learned is that SaaS is really hard to scale, and total addressable market is the issue. Unless it can get to $100K MRR it is probably not worth pursuing.

Hormozi may be right in the end. The fewer things you take on, the more each one can scale. I am more selective with my time now, and I am fortunate to be able to focus on what I want: YouTube, and helping my closest friends build their businesses bigger.

The most important thing is persistence, paired with a sober and objective viewpoint. If there is an intersection of money and your idea, test it before you commit to it. Prove today that it can make money.

And despite everything I talk about online, money is not everything. It is fun to work on this AI stuff because we are at the frontier of the models and we can do all the things. But there is more to life than making money. Finding a balance is important.