Transparency and authenticity are my brand

We did some amazing, high-level finance for the final deal structure last night, when I was running on fumes. I think my intuition has been telling me that a chance to change the world for the better is extraordinarily rare, and the window might be closing, so I need to move fast:

When I go to the diner every morning, I listen in on conversations with ordinary people. I always hear something about AI. It is always misguided and wrong, but it would be a fool’s errand to try to educate endusers, one at a time, with no proof-of-concept to persuade them.

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

He literally refused to troubleshoot an intermitted issue because he said, “Well, it’s working now. I can’t fix what ain’t broke.”

That demonstrates what were are up against. People already have hardened negative opinions about AI. As an Agent of Change, I realize how daunting the challenge is. But NO challenge is ever daunting to me, because if I have a plan I can succeed: “Plan your flight, and fly your plan.” I learned that from Capt. Bill Kight.

My plan is based on limiting the first users to “pioneers.” People who will help us make our iteration of AI the best in the world, because we will have an army of users to help us. To my knowledge, no one has ever launched a consumer-facing product that way. But that’s what it’s gonna take.

So, the way we are gonna start changing minds is multi-fold:

• We are not gonna do what Microsoft does: ship buggy software they know is buggy when they ship.
• And we are not gonna do what Apple does with its walled garden:

My Russian ex-wife is dismissed as stupid because she sounds like Natasha from Rocky and Bullwinkle. She sounds like a cartoon character; I look like one. I am her Boris Badenov.

But, she is quite intelligent and she followed a logical path in troubleshooting her problem with her Yahoo email account on her iPhone.

But Apple didn’t facilitate. Apple got in her way. She has tremendous agency, but as a non-native English speaker, she has an obstacle that Apple only compounded with its cryptic error screen and non-intuitive placement of controls. I would never subject a user to that and if we’re gonna scale this mountain of AI-generated fear and disbelief, we need to do everything we can to get people on our side.

And that’s what I’m gonna tell Apple. Fix Mail for iOS and Safari, or don’t expect me to launch using those clients. They are fundamentally flawed. You don’t get a second bite of the apple and we can’t launch MM using those tools, as is. Apple is gonna have a $300-$400B investment in this. That should motivate them.

But I don’t know whether they can make the pivot back to Steve Wozniak. To me, it’s essential and obvious. There is nothing more difficult than restoring trust. I’ll paraphrase George W. Bush: “Fool me once, shame on you. Fool me twice, well, you can’t fool all the people all of the time.”

So, part of my campaign to make Apple see the light is some very public criticism of the current state of their core clients — Mail and Safari. Personally, I don’t want my own brand to suffer because of it.

Which is why I could easily pivot to Alphabet or Microsoft. They have no stake in “trust” because it isn’t in their DNA. But, with the mountain we as a species need to climb, I think Microsoft and Alphabet are far more agile. Apple seems too committed to its flawed walled garden. In this respect, Steve Jobs was blinded by his own “vision” but Woz got it 100% right.

I’m still thinking that a 10% bump in valuation might be low. If it was 15% percent, then Microsoft or Alphabets smaller market cap still delivers on my goals of funding the causes I believe in at the same level.

And, I think I should be totally transparent about all of this. At some point, I can imagine cribbing from this email with hyperlinks to my past public comments about Steve Jobs, Woz, Bill Gates, Microsoft, the amazing work being done right now at OpenAI, and the genius of PageRank and its creators, Larry Page and Sergey Brin.

And I already have a connection with Esther Wojcicki, and we share a passion for education and encouraging kids to read.

At this point, I need to be agnostic. Of course I’m in love with Apple’s ethos. And they still talk the talk. But clearly, they don’t walk the walk — anymore.

History has taught us what two guys in a garage can do: The Wright Brothers, Walt and Roy Disney, Bill Hewlett & Dave Packard, Steve Jobs & Steve Wozniak, Bill Gates & Paul Allen, Me and John Stackpole, Me and Sudeep Goyal, Me and Paul Norton, Me and Brian Stallcop, Me and Mike Carter, Me and my daughter, Sophie, for whom I built the original working prototype of TweenTribune.com in an hour. Where? In my office, which was a converted garage.

Just two guys in a garage with no constraints — that’s what it’s gonna take to make this work.

So, in my mind, I shouldn’t just focus on Apple. I have real doubts about them. I think Tim Cook is an excellent steward for Apple. But I think even he would admit that he is neither a visionary like Jobs nor an engineer like Woz, who delighted in delighting users.

But as a brilliant tactician, I think Tim will see that the environment for a “do-over” with AI, to restore trust in technology, cannot happen with Apple’s current iteration of iOS. And my story about Tanya’s terrible enduser experience is Exhibit A. The screenshot of the error message was the icing on the cake.