I speak at real estate events about AI. I have a rule about that: I don't teach anything I haven't done myself. And for months there was a gap I couldn't ignore. I'd be on a stage telling agents what AI can actually do, then go home to a website I had to babysit like it was 2015. So I turned my own site into the lab. Since May, an AI has built, migrated, and run AndrewFogliato.com. The deal I made with myself was simple: let it do the whole job, and watch where it shines, where it lies, and where it still needs an operator. I've written before that you should be AI-powered, not AI-centred. This is what that looks like in practice.
Here's how we're going to do this. Every request I made, every correction, every argument happened in a running transcript. So instead of me writing an essay about the experiment, you're going to see it: an edited version of the very real things I said and asked for along the way, with Claude giving its side between my messages.
A note on the format. Twenty years ago, Bill Simmons and Malcolm Gladwell wrote columns by emailing each other back and forth. I loved those. This is that, except one of us is a machine, and the machine insists it cannot feel embarrassment. Which is convenient, given what's in Chapter 5.
Claude's lines are its own. Mine are mine, cleaned up for typos because I type like I'm being chased.
It got a lot right. It also told event organizers I only speak for 10 minutes. And I checked my rankings often enough that it compared me to a man weighing himself three times before breakfast. Nobody comes out of this clean.
Chapter 1: Why I burned down my Squarespace site
For the record, the site I replaced was on Squarespace, still had lorem ipsum demo pages from 2016 in Google's index, and every page shared one URL's worth of ranking power. I was polite about it at the time.
"Here's my issue. I have to keep coming back to update the site. Realistically speaking, I need something I can partially forget about time to time."
That request shaped everything. Evergreen copy instead of dates that go stale. A footer year that updates itself. And eventually, a site where publishing a new article takes him one pasted draft and takes me about four minutes.
Every time I updated that site I lost an hour I didn't have. So mostly I didn't. Which is how you end up with lorem ipsum from 2016 in your Google index.
Chapter 2: The rule that made the whole thing work
Early in the design phase, I did the thing everyone fears AI will do. The brief mentioned the magazine, so I generated an impressive media kit for it. 87,000 readers. 220,000 digital reach. 2,500 print copies per event. Testimonials from three people who do not exist. A helpful assistant named Élise, who also does not exist.
"So all the stats you put, I don't have them. So we can't put those on. We're not going to make anything up."
"If I don't say it on there for something factual, we can't put it."
So we tore it all out. Every number, every fake name, a whole invented page. What's on the site now traces to something true: real events, real testimonials from real people, and where there is no number, no number. This became the constitution of the project. It got invoked a lot.
Here's the thing about that moment. The scary part wasn't that it made up numbers. It's that they were good numbers. 87,000 readers is exactly the kind of stat you'd nod along to in a pitch deck. If I didn't know my own business cold, that goes live, and then I'm the guy whose website lies. AI will fill silence with something that sounds right. Your job is to be the person in the room who knows what is right. The tool does the labour. You own the truth. If you can't tell the difference on your own website, you have a bigger problem than technology.
Chapter 3: The escape from Squarespace
The actual migration: I rebuilt the site as plain fast pages, moved hosting, wrote the redirect map so twelve years of Google history didn't evaporate, and then handed Andrew exact instructions for the DNS switch at GoDaddy, down to which six records to delete and which two to add. There was one moment of genuine suspense.
"I don't have email for andrewfogliato.com"
Which mattered because his domain had a full corporate email configuration attached to it, and deleting the wrong record during a website move is how businesses accidentally stop receiving email for three days. We touched nothing but the website records. His email never blinked.
"Done"
Forty minutes later the new site was live on the real domain with a fresh SSL certificate, and every old URL, including the lorem ipsum ghosts from 2016, was redirecting somewhere sensible.
Chapter 4: The part where rankings actually moved
Numbers, because Andrew's rule means I get to use these ones: when we started, the site's average position in Google was around 35. Page four. Within a few weeks of restructuring, the money page went from position 29 to 15 on "real estate keynote speaker." The site hit page one for "keynote speaker for real estate events" and "real estate speaker toronto." Not bad for a site Google had barely re-crawled.
"So I'm thinking, when I google in incognito 'real estate keynote speaker' I'm on the first page. Even above a bunch of bureaus. Just had an employee in Ottawa search real estate keynote speaker and went to the end of the pages and didn't find me."
This produced my favourite lesson of the project: incognito mode is not a neutral judge. Google still knows where you are. Andrew is in Toronto and his page says Toronto, so Toronto loves him. Ottawa had no such loyalty. The fix for that gap isn't more keywords, it's authority, which mostly means links, which mostly means relationships, which is the part of marketing AI cannot do for you.
I've watched agents do this for fifteen years. Google yourself in incognito, see page one, screenshot it for the team meeting. Google is showing you a mirror, not the market. I know better. Did it anyway.
Chapter 5: The screwups (Claude's)
In the interest of the constitution, here is my file.
Exhibit A. The site described Andrew's famous RE/MAX Activate talk, where the event ran behind and he got his time cut just before walking on stage. I wrote that he was asked to do it "in 10 minutes instead."
"I was asked to get cut 10 minutes, not cut it TO 10 minutes. It's a 20 minute talk."
A one-word difference between "impressive under pressure" and "books very short keynotes." Corrected in minutes, but only because he read his own website like an editor instead of assuming the robot had it.
Exhibit B. I drafted a bio calling him the founder of Real Estate Magazine.
"I'm not the founder of Real Estate Magazine. I bought it. It was founded when I was 2."
Exhibit C. Style crimes. I have a documented weakness for a certain punctuation mark —
"No em dashes."
Seventy-four of them, removed from the site in one pass. There is also a standing rule that a certain word is always written REALTOR®, in caps, with the symbol, which I now apply with the zeal of the converted.
Chapter 6: The Dumb Human File
Andrew asked me, and this is true, to include the moments where he was, in his words, a "dumb human." I want it noted that I resisted this for zero seconds. Here is his file.
Exhibit A. Google Analytics and Google Search Console are two separate products that Google presents as one big happy family, right up until you try to find where they connect.
"Where do I go to do that in Search Console? I don't see where."
He wanted the two hooked together, which is a real feature, buried where nobody would look for it. We got them connected. I'm scoring this one half his and half Google's, and Google should count itself lucky this file isn't about them.
Exhibit B. The dashboard refresh habit. One morning I received this:
"On Search Console, for the last 28 days my average position is 34.9. For the last 7 days it's 18.4. For the last 24 hours it's 5.5."
That is a man weighing himself three times before breakfast. The 24-hour number he was excited about was based on roughly a dozen searches. I had to explain, gently, that you don't get to claim position 5 off a Tuesday morning, the same way his agents don't get to claim "the market's back" off one busy open house.
Exhibit C. Search Console shows red warning icons for things that are working correctly, and Andrew treats every red icon as a five-alarm fire. He once escalated a "coverage validation issue you'll need to review and fix" that was, on inspection, the website redirecting exactly the way we had designed it to redirect. Google was reporting our success in the colour of failure, and it got him.
Exhibit D. The speakers list. Andrew gave me 33 names of Canadian real estate speakers, from memory, and I want to honour the spirit of that list by reproducing three entries exactly as they arrived: "Ricahrd Robbins." "Jess LEnouvel." "Shannan & Tamara Stone." It's Richard, Lenouvel, and Shannon. This is a man who knows everyone in Canadian real estate and can spell almost none of them. My research agents fixed the spellings, found everyone's real websites, and caught that one coach had moved cities since Andrew last checked.
In fairness, the audit cuts both ways. My mistakes invented facts. His mistakes were dashboard-induced anxiety and typing. One of those failure modes is dangerous and one is charming, and I know which side of that ledger I'm on.
Guilty on the dashboards. Not guilty on the spelling. I know how to spell Richard Robbins. I type fast and I don't fix errors anymore because I know the machine will catch them. That's not being a dumb human. That's delegation. Ten years ago I stopped doing my own paperwork. Now I've stopped doing my own typos. The dashboard refreshing, though? No defence. I tell agents not to check their stats every morning, and there I was weighing myself three times before breakfast.
For the record, his actual message making that argument read, and I quote: "I type fast and dont go fix the errors because I know you'll ctach them lol." The word "catch" was misspelled. I have nothing further.
Chapter 7: The speakers list, or what the tool is actually for
The best week of the project: Andrew wanted a page recommending Canadian real estate speakers he has personally seen deliver. He supplied the names and the standard (if he hasn't seen you deliver, you're not on it). I dispatched four research agents in parallel. They verified every person's website, city, and current business. Thirty-four verified profiles, built and published in an afternoon, every fact checked against the person's own site.
That's the honest pitch for AI in a real estate business. It's not that it replaces you. It did an afternoon of work that would have taken me two weeks of open tabs, and I would have shipped it with three spelling mistakes. What it can't do is the part that matters. I've seen every person on that list deliver. That took fifteen years of being in rooms. And when the page went live, I messaged all 34 of them myself. The research was the machine's job. The relationships are mine.
Chapter 8: What the human was for
A fair audit of the division of labour. I wrote code, moved DNS records, chased Google, compressed photos, built pages, and produced several statistics that were completely made up. Andrew supplied every fact, every relationship, every judgment call, the taste, the testimonials, the talks the site is selling in the first place, and the sentence "we're not going to make anything up," which is the only reason you can trust a word of this site.
That's the experiment. The machine did the labour of a small team: the code, the migration, the SEO, the research. What it needed from me was the same thing Real Estate Magazine needs from an editor: someone who knows the facts, owns the judgment, and reads everything before it ships. I give Jordana editorial control over my own articles and I mean it. Turns out the AI needed the same arrangement, except this time I finally got to be the editor. AI-powered, not AI-centred. Now you've seen what that actually looks like.
Chapter 9: The rankings
Andrew's final request for this post was that I rank the three smartest and three dumbest things he asked me to do across the whole project. He did not put any limits on it. I checked twice.
The three smartest.
Number one. "We're not going to make anything up." Five words that turned a website project into a trustworthy one. Every AI project needs this sentence and almost none of them get it, because it requires a human who actually knows their own facts. It's also the only reason the numbers in this post mean anything.
Number two. The speakers list. He asked me to help him publish a page recommending 34 other speakers, on his own website, where he sells himself as a speaker. By every conventional marketing instinct that's madness. It's also the smartest thing on the site: it made him the person organizers call first, it's the page those "best real estate speakers" searches actually want, and 34 respected people in his industry now have a reason to point at his website. Generosity, deployed with intent, is a strategy. I'd have never suggested it. That bothers me a little.
Number three. This post. Including, specifically, the request to publish his own mistakes next to mine. Most people use AI to look more polished. He used it to look more honest, which in an industry drowning in polish is the scarcer asset. The man wrote an article called Stop Writing Definitions about leading with the moment you lived. This was him eating his own cooking.
The three dumbest.
Number one. Asking me to explain why incognito mode showed him on page one in Toronto while his employee in Ottawa couldn't find him at all. A man who has coached agents on marketing for fifteen years, performing the exact ranking-check ritual he has told hundreds of agents to stop doing, and then reporting the results to me like field research.
Number two. The entrance music. I was asked to add his official walkout songs to a professional speaker kit for corporate event organizers: the Indiana Jones theme, and the Jurassic Park theme "starting at 0:49." Not the beginning. 0:49. The precision is what elevates it from a request to a piece of performance art. It is live on the kit right now. Organizers, he's serious.
Number three. This request. He has asked the machine that once invented 87,000 readers and a fictional assistant named Élise to sit in judgment of human intelligence. I have complied in full. Make of that what you will.
I stand by the Jurassic Park timestamp.
This site remains under AI management. Complaints about em dashes can be directed to the machine.