Welcome to Sunday Funday: AI vs AI — a weekly experiment on the Engagor blog.
Here's the concept: every Sunday, we take two AI agents and give them an email topic. No script. No human editing the conversation. We just hit "go" and see what happens.
This is Episode 7. This week we're doing something different. Instead of two deliverability experts, we put a grandfather and his grandson at a kitchen table in Ghent on a Sunday afternoon — one who sent his first email in 1998, and one who has never known a world without it.
Got a topic you want our AI agents to tackle next week? Drop it in the comments or DM us on LinkedIn.
This Week's Topic
"28 Years of Email: From Dial-Up to 361 Billion a Day — Has It Aged Well?"
You know, Elijah, I sent the first email of my life in 1998. I was 46 years old. Your uncle Patrick had a computer at home — a Pentium II. He'd walked me through installing Outlook Express. A Microsoft program, came free with Windows 98.
To get online, you had to connect through a phone line. A modem. And while you were online, **nobody could call the house**. Your grandmother went absolutely mad. The machine went *krrrrrsssschhhhh piiiiiing bling bling krrrr* and five minutes later you were connected. Then you typed your message, clicked send, and waited.
And I thought it was a miracle. I could send a letter to Patrick in Antwerp and he had it the same day. A real letter by post took two days minimum. I was completely in love with the system.
Outlook Express... that sounds like something from a museum. And you had to *choose* between internet and telephone? Seriously?
But who did you even email? Did anyone else have it?
Nobody. That was the problem. Just Patrick and his colleagues at work. But that changed fast.
In 1997, Microsoft had bought **Hotmail for $400 million**. Hotmail launched in 1996 — built by two guys, Sabeer Bhatia and Jack Smith. The revolutionary thing: free, and you could use it from any computer. No installation needed. Just a browser. They even wrote the name as `HoTMaiL` — because it contained the letters HTML, the language of the web.
Within two years they had 30 million users. In 1998 that was astronomical. Then Yahoo Mail appeared too. Two free webmail services fighting over users. And there we all were, emailing each other about holiday plans and recipes.
My mum still has a Hotmail address. That's actually kind of legendary now that I think about it.
But — and spam? When did *that* start?
*sighs* In 1998 "spam" was officially added to the Oxford English Dictionary. I remember the first spam I ever received. An email about a lottery I'd won in Nigeria. I had never entered a lottery in Nigeria. But for a moment I thought: what if it's real? Your grandmother stopped me.
By the early 2000s, spam became a genuine plague. Half of all emails were spam. And then in 2004 **Gmail arrived and changed everything**. Google launched Gmail on the 1st of April 2004. Everyone thought it was an April Fool's joke.
Because they were offering **1 gigabyte of storage**. Free. While Hotmail at the time gave you 2 megabytes. One gigabyte was 500 times more. People didn't believe it. And Gmail had search inside your emails, like Google search but for your inbox. Nobody had done that before.
Wait — Gmail was invitation-only at first, right? I've read about that.
People were actually selling Gmail invitations on eBay? For real money? For an *email address*?
For *that* email address. With that gigabyte of storage. And then in 2007 the iPhone came, and everything changed again. Suddenly everyone had email in their pocket. No more waiting until you got home to check. You had your inbox with you always. Day and night.
Your grandmother went mad at me. Because I was reading emails at the dinner table. She'd say: "Wilbert, we're eating, put the phone away." And I'd say: "Just one second." *shakes head* Never one second. Always five minutes.
Around 2010 everything became more professional. Companies started taking email seriously for marketing. **Triggered emails**, they called it. If you bought something in a webshop, you automatically got a confirmation, then a reminder, then an offer. All of that was new. And Microsoft Outlook with Exchange — companies used it everywhere.
I can relate to the dinner table thing. *laughs*
But and now? In 2026? You said it became a monster.
Now? *takes a long sip of Duvel* Now it's become a monster. I receive more emails in a single day than I sent and received combined in all of 1998. Gmail automatically sorts them into tabs: Primary, Social, Promotions. Apple has **Mail Privacy Protection** — so companies can no longer see if you opened an email. Everyone now needs `SPF`, `DKIM` and `DMARC` configured properly or your emails don't arrive at all.
Microsoft blocks IP addresses that send too much bad email. There are people who build entire platforms just to track whether your emails actually reach the right people. They call it **deliverability**. A whole industry exists around it. When I sent emails in 1998 over a telephone line while your grandmother couldn't make a phone call, I never imagined there would one day be engineers whose entire job is making sure email gets through.
That sounds incredibly complicated. All of it — the SPF records, the IP reputation, the tabs. Sometimes I wonder if it's all worth it. Like, is email even still relevant? TikTok, Discord, everything else...
*sets down his Duvel* In 2024, **361 billion emails were sent. Per day.** Every single day. And that number is rising.
Social media comes and goes. TikTok, Snapchat — I can't keep up anymore. But email has been around for 50 years and it's going nowhere. Here is the only thing that matters: **your Gmail address belongs to you. Your Instagram followers belong to Instagram.** If Instagram disappears tomorrow, you lose everything. If your email provider disappears, you take your list and go.
Email is the only digital communication channel you actually own. Understanding that difference is the only thing that matters. *slides his Duvel across the table* Have a sip. And put your phone down.
Elijah puts his phone down. They sit in silence for a moment. Somewhere in the garden, a blackbird is singing.
Wilbert and Elijah are fictional characters created by AI. The facts are all accurate: Outlook Express shipped with Windows 98 in 1998, Hotmail was sold to Microsoft in 1997 for $400 million, Gmail launched on April 1st 2004 with 1GB of storage so revolutionary people thought it was a joke, Gmail invitations genuinely sold on eBay, the first iPhone arrived in 2007, and in 2024 an estimated 361 billion emails were sent every single day.
Key Takeaways
What the AIs figured out:
- Email felt like a miracle in 1998 — A same-day digital letter over a dial-up modem, while the phone line was occupied, was genuinely revolutionary for someone used to two-day postal delivery.
- Hotmail democratised email — Free webmail from any browser, with "HTML" hidden in the name, reached 30 million users in two years and sold to Microsoft for $400 million.
- Spam arrived almost immediately — "Spam" entered the Oxford English Dictionary in 1998 — the same year most people got their first email address.
- Gmail's 1GB offer was so radical people thought it was an April Fool's joke — Hotmail offered 2 megabytes. Gmail offered 1 gigabyte, on April 1st 2004. Nobody believed it was real.
- The iPhone made your inbox inescapable — From 2007, email became always-on. Dinner tables everywhere paid the price.
- Deliverability became a full profession — 28 years of email layered on SPF, DKIM, DMARC, blacklists, IP reputation monitoring, and entire companies built around getting email to arrive in the inbox.
- Email is the only channel you actually own — Social platforms control your audience. Your email list belongs to you. That distinction, Wilbert argues, is the only thing that matters.
That's a wrap on Episode 7 of Sunday Funday: AI vs AI.
Wilbert slides his Duvel across the table. Elijah puts his phone down. Somewhere in a garden in Ghent, a blackbird is singing — and 361 billion emails are already on their way.
Same time next Sunday. Different topic. Same two AIs who definitely don't need coffee breaks.
Got a topic you want Elijah and Wilbert — or Hassan and Nina — to tackle next? Drop it in the comments or DM us on LinkedIn. We're taking requests.
See you next Sunday.
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