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- AI AI Whoa... and Who Can We Trust Inside Our Digital Lives?
AI AI Whoa... and Who Can We Trust Inside Our Digital Lives?
Happy Sunday…
Before I get started…I was supposed to be in Israel this coming week with 33 friends (many non-jewish and visiting for the first time), but we cancelled last week. As of yesterday, all flights would have been cancelled anyway.
As for why…
Yaba Dabba Do!

Of course the New York Times did not write the above headline, so the internet did.
The memelords are having a day as the USA and Israel began rebliterating the brutal Iranian regime with some actual 4 D chess…
My favorite memes…
I do not have any ‘good takes’ on this war or the Middle East, but you can always count on Rashida Taliban and the rest of the Qatar flunkies for a bad take (I go for the comments)…

Onward…
In my day jobs all I think about is how AI can help build and grow the startups we back and my own Stocktwits.
I have one friend, Greg Isenberg, who started a Youtube channel to help with this problem. It is excellent.
This week he did an explainer on how to use Perplexity Computer to build 5 uses cases to help founders get customers and monitor competitors. Every sale sand marketing person should watch…
The one hiccup in the magic of AI that Greg demo’s is that you must trust Perplexity connecting to your gmail account to send emails. This part makes me uneasy.
I asked my friend Danny Frenkel, the founder of Punchup (a portfolio company), to explain how big and important this next unlock is for AI. Danny spent 12 years at Facebook in product so he knows the good, the bad and the ugly of trust, data and utility. Have a read…
Like a lot of folks I've been playing with AI lately, vibecoding new products, trying desperately to impress my engineers. I built an Instagram chatbot in about 36 hours that replicated a major feature of a competitor. The code wasn’t the constraint. The AI generated most of it instantly. The bottleneck was permissions: auth tokens, Meta dashboards, buried settings, toggling the right switches in the right order. The intelligence was ready but access wasn’t. The AI could write the logic, but it couldn’t log in and configure the environment.
That feels like a preview of what’s clearly coming next. Today AI drafts, summarizes, suggests. The next phase is when it acts, logging in, connecting systems, changing settings, completing workflows. And that shift runs into the same force that shaped the last decade of the internet: trust.
From my time at Facebook, one lesson was clear. Privacy norms don’t move when every concern is resolved. They move when the value exchange becomes undeniable. People respond to utility.
Google made their privacy trade tangible. Email scanning powered spam filters, auto-filled forms, flight reminders, package tracking. The benefit was constant and specific. Data in, utility out. The exchange felt concrete.
With Facebook, the bargain was intellectually understood but less directly experienced. The service was free because data powered the model, but the connection between what you gave and what you got was diffuse. The mechanics were similar. The perception was not.
AI is approaching a similar inflection point, but with higher stakes. The last decade was about who could harness our data. The next feels like who we'll trust to act inside our digital lives.
Data sharing is passive. It allows companies to observe and optimize. Agent access is active. It allows software to operate on your behalf, to change configurations, move information, execute decisions. One lets a company watch you. The other lets software act for you.
The upside is larger. An AI that drafts saves minutes. An AI that can navigate your tools and complete multi-step workflows collapses entire categories of friction. The power compounds with context and authority. But so does the risk.
The real bottleneck isn’t just model capability. It’s the permission layer around it. The privacy debate of the 2010s asked who gets to use my data. The next one asks who gets to use my credentials.
The next battle is shaping up now…
Have a great Sunday.
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