I can’t part with my MacBook but I can’t partner with Apple

My Russian ex-wife is nobody’s fool. She has a strong accent and because of that people sometimes talk down to her like she’s Natasha from Rocky and Bullwinkle. They assume she’s dumb. She’s not. She’s logical. She’s stubborn. She solves problems.

Yesterday the problem was simple. Yahoo mail on her iPhone stopped working.

She did what any normal user would do. She opened Mail. She tried to refresh. It failed. She followed the onscreen instructions. She tried again. It failed again.

At this point the software should have helped her recover.

Instead Apple got in her way.

The error message she got was cryptic. It didn’t tell her what was wrong in plain English. It didn’t give her one button that said fix it. It gave her nothing a non-native English speaker could act on without guessing. And when she tried to go to where you would assume the account settings live, Apple had buried the control in a non-intuitive location.

That’s not a technical failure. That’s a design failure.

Apple likes to pretend it is the company that protects normal people. But in this case Apple put a normal person in a loop she could not get out of without me.

I want to be really clear about why this matters.

She had the discipline. She had the patience. She had the exact mindset I need in my first generation of AI users. High agency. Good intuition. Willing to troubleshoot. Speaks two languages. This is the ideal early adopter. She is exactly who I want helping me make the product better.

And Apple made her feel stupid.

That is unforgivable if you are asking people to trust you with their data and their identity and now their intelligence.

If Apple ships an experience where an intelligent adult cannot recover her own email on her own phone because the UI hides the fix and the error message reads like it was written by Legal, not Support, then Apple is no longer the company Steve Wozniak built. Woz delighted in delighting users. This iteration of Apple frustrates users then blames them.

Trust is not a vibe word here. Trust is literally the product I am trying to ship.

I am asking people to trust AI to help them. That is already an uphill climb. I hear it every morning at the diner. I hear it at the Subaru service counter:

Even yesterday, at the Subaru dealer, the technician refused to even consider using AI’s 5-point troubleshooting guide to an intermittent problem with my power liftgate — only because of its provenance. He said, “I can only do what the Subaru book tells me to do.”

Everybody has an opinion about AI and most of those opinions are already negative. I cannot afford unforced errors. I cannot afford day one stories where someone says yeah I tried your thing but Mail broke and I couldn’t even get signed in and then Safari popped an error I couldn’t read.

You never get a second chance to make a first impression. You do not get a second bite of the apple.

If I launch inside that broken experience I inherit Apple’s broken trust. That poisons my brand. I am not doing that.

So here’s where I am right now.

Apple still talks the talk on privacy and trust. I respect Tim Cook. Tim is a world class operator and a grownup. But I don’t know if Apple can still walk the walk at the user level. Not with Mail for iOS in the state it’s in. Not with Safari acting like a gatekeeper instead of a browser. Not with critical controls hidden behind non-obvious paths that even native English speakers can’t find without a YouTube video.

Meanwhile Microsoft and Alphabet are not pretending to be the temple of trust. They’re not emotionally tied to the walled garden myth. They just want the business. And because they are not defending a religion they can move faster.

Do I love Microsoft Exchange melting down my mail store and forcing me to rebuild half a million messages from scratch over and over again? No. Do I love Microsoft Word? No.

But Microsoft has a massive stake in OpenAI and I love GPT-5 Thinking. It works. And Google’s core is still PageRank. Larry Page and Sergey Brin solved the problem of relevance for the entire planet. That DNA is still there. They know how to rank signal and strip noise. That is the mindset we need.

So I’m agnostic.

Apple does not automatically get to be the launch partner for MagneticMatch or any of my trust layer work. Not anymore. Not after what I watched my ex-wife go through with something as basic as checking her Yahoo mail.

If Apple wants a do-over on AI and wants to be the company that restores trust in technology, then Mail and Safari on iOS have to be fixed in a way that is obvious and fast and self-evident to a smart adult whose first language is not English. No buried controls. No lawyer screens. No blame-the-user loops.

Make recovery as simple as one button that says fix my mail and then actually fixes it.

If Apple can’t or won’t do that, I will not launch on Apple first. I will go where I can ship a clean story.

Because here’s the reality. Changing hearts and minds on AI is going to take the same energy it took for two guys in a garage to build the first airplane or the first Apple computer. No committees. No excuses. No walled gardens. Just solve the user’s problem and earn trust one interaction at a time.

That’s the only path that works at scale.