Bet the farm

Or risk losing it all

I read the 10-K filings touting AI transformation. Then I talk to the CIOs and employees. The gap is staggering.

Press releases announce “company-wide AI adoption.” Hallway conversations tell a different story. Employees haven’t opened the tools in weeks. The data lies. Comms lies. Dashboards show logins, not usage. Activation, not integration.

This is transformation theater. The appearance of change without the pain of change.

A VP of AI gives you someone to blame when it doesn’t work. An acquisition gives Wall Street a two-year narrative. Neither rewires how your company operates. You can acquire talent, technology, distribution, customers. You cannot acquire conviction. Conviction only comes from firsthand experience with the tools. When you outsource that experience to a hire, you outsource your ability to lead.

Tobi Lütke doesn’t have a Chief AI Officer. He is the Chief AI Officer.

His memo to Shopify was blunt: prove AI can’t do the job before asking for headcount. Not encouraged. Mandatory. Shows up in performance reviews. He posted it publicly before it leaked. Not a memo about change. A demonstration of it. Revenue up 20-40% annually. Headcount down from 11,600 to 8,100. Tobi can make hard calls because he knows what’s possible. A CEO relying on their CAIO’s judgment is steering blind.

Google had every advantage and almost blew it anyway. They invented the transformer. They owned TPUs. They had the talent, the data, the distribution. What they lacked was the boldness to cannibalize their own product. They declared “code red” internally. Their first response was Bard: a hedge, not a bet. The market saw through it instantly.

Then they actually committed. AI Overviews now appear in 30% of searches. When users see one, only 1% click through. Some keywords collapsed 90%. Google’s entire business depends on those clicks. They’re eliminating them anyway. Betting hundreds of billions in annual revenue on a future that might not work.

Acquisitions can’t get you here. You buy someone else’s conviction and hope it survives your culture. Atlassian buys The Browser Company. Workday acquires Sana. The acquirers tell investors not to expect impact until 2027.

We know what happens next. Instagram’s founders left Meta. WhatsApp’s founders left Meta. Nest’s founders left Google. The pattern is so consistent it’s almost physics: founders leave, DNA dissolves into your existing architecture. All that remains is a press release and an earnout.

Worse: acquisitions signal strength to Wall Street but reveal weakness to everyone inside. Your best people see the theater. They leave for places where transformation is real. The acquisition accelerates the decline it was meant to prevent.

These companies don’t know they’re already dead. They think they’re adapting. They’re documenting their decline in press releases. Their employees quietly disengage from tools leadership has never touched.

Tobi rewrites Shopify’s culture in public because he’d rather look extreme than become irrelevant. Google is betting against their best product because they learned hedging nearly killed them.

Everyone else is buying time. Time has this weird habit of running out.