I’ve been quiet lately. Blame it on New Zealand, building the next version of Tupai, and hitting the road for our alpha tests.

Instead of hiding behind survey links, we’ve been sitting in classrooms with our students and having unscripted conversations with their parents. There’s nothing quite as humbling, or as useful, as sitting close enough to watch the exact second a 14-year-old gets completely stuck on a screen you designed.

It was during one of these sessions in Tanjung Lumpur that a friend sent me that famous Mona Lisa meme. You know the one. Nine panels running from “original sketch” to “market needs” to a pixelated blur labeled “development’s understanding.”

Then came the panel that made me laugh out loud in a room full of focused teenagers: the sales team’s version.

Braided hair. A Big Gulp. Bling.

Somewhere between the pitch and the product, Mona Lisa went to the club.

I sent it to three founder friends. Nobody replied with “haha.” They all said, “oh no.”

Because we’ve all shipped that Mona Lisa.

The Tech Changes, the Trap Stays

It doesn’t matter who’s holding the pencil anymore. It could be a human designer, a software engineer, or a shiny new AI agent. Swap the agent out too. Sonnet, Fable, Opus, or whatever ships next quarter with an impressive demo video, the “development’s understanding” panel still ends up as a blur.

Whether a human or a large language model writes the code, the alignment problem remains fundamentally human.

Every panel is really just a broken feedback loop. A game of telephone played by people with deadlines.

Development builds its best guess. Sales pitches its best guess at development’s best guess. Nobody checks any of it against a real human, so the distortions stack until Mona Lisa is holding a drink.

Fewer People, Shorter Line

Most companies try to fix telephone by adding more telephone. More reviewers, more sign-offs, more people nodding along.

That’s the opposite move.

Shorten the line instead. Fewer people between whoever builds the thing and whoever actually uses it means fewer chances for someone to helpfully improvise a Big Gulp into the picture.

Though fewer people only helps if the ones left keep checking.

A small team sealed in a room will agree on the Big Gulp faster than a big one, and with far more conviction. Shorten the line, then point whoever’s left at an actual user.

This shorter line protects the rest of the company, too.

Nobody in sales promises the braided hair because they’re evil. They’re simply standing between a roadmap and a quota with nothing finished to show, and hope is free.

It works beautifully right up until the customer opens the box.

Then the trust is gone.

Checking the Sketch

The real fix isn’t clever.

Sit in the back of a classroom and watch a real kid use the thing.

That’s what these past few weeks have been about: catching the gap between what we think we built and what a teenager actually experiences, while it’s still cheap to fix.

Nobody draws Mona Lisa wrong on purpose. They just forget to check the sketch against the real face until somebody in sales has already promised she’d be wearing something else.

We’re still checking our sketch against reality, and we’ll be opening our beta to a small group of testers soon.

If you want to help us make sure we don’t ship the Big Gulp, stay tuned.