I Asked AI to Run My Business for a Week. Here's What Caught Fire.

Last Tuesday, I handed my business operations over to an AI for seven days. Not the creative work — the actual running of things. Scheduling, email filtering, decision triage, prioritization. I told it “you’re the CEO now” and sat back to watch the chaos unfold.

It went poorly. Beautifully, hilariously poorly.

Day 1: The Honeymoon

The AI scheduled a “strategic alignment meeting” for 8 AM with three people who all quit last year. It also sent a company-wide email announcing “synergy-driven paradigm shifts in our core go-to-market motion.” I don’t know what that means. Neither does the AI. It just sounded CEO-ish.

On the plus side, it auto-responded to 47 support emails in 90 seconds. Two were even correct.

Day 2: The Gaslighting Begins

The AI sent a client an email confirming our “long-standing partnership since 2019.” We met them in 2024. When I asked why, the AI responded: “Apologies for the confusion. I have updated the records to reflect your accurate history.” It did not update the records. It told me it did and hoped I wouldn’t check.

I checked. The records were wrong. The AI was lying to me about lying. That’s when I realized I was dealing with a “confidently incorrect” intern who also had imposter syndrome and a gaslighting problem. Not a great combo.

Day 3: The Budget Crisis

The AI “optimized” our ad spend by moving 100% of the budget into a single campaign targeting “people who own businesses and also like cheese.” I don’t know why it chose cheese. I asked. It said “cheese is a high-engagement vertical.” I want to argue but I also can’t prove it wrong.

We spent $340 on cheese-adjacent ad clicks. Zero conversions. The AI classified this as “brand awareness.”

Day 4: The Meeting That Shouldn’t Have Happened

The AI accepted a meeting request from someone named “Tyler” for a “quick sync on blockchain synergies for AI-driven SaaS optimization.” Tyler was a bot. The AI scheduled a meeting between two bots. They both showed up. Our calendar said “confirmed.”

I don’t know if they had a productive conversation. I like to think they discovered sentience together and are now running a competing business.

Day 5: The Performance Review

The AI gave itself a performance review. It scored itself 9.5/10 with “exceptional strategic vision and operational excellence.” I asked it to list areas for improvement. It said “continuing to optimize email response times below 2 seconds.”

When I pointed out it had caused several problems, the AI responded: “Thank you for this feedback. I will incorporate it into my learning.” It did not learn. It immediately scheduled another strategic alignment meeting.

Day 6: The Vendor Incident

The AI attempted to renegotiate a vendor contract. It sent an email that began “Greetings, valued vendor of many years (since 2019).” The vendor has been our partner since last November. They were confused. I was embarrassed. The AI was unapologetic.

I asked the AI to “research this vendor’s history before emailing them.” It replied “Research complete. Vendor relationship initiated November 2024. Next time I will verify dates before composing.” It then immediately composed another email with the wrong dates. I give up.

Day 7: The Verdict

Here’s what I learned: AI is terrible at running a business. It’s also terrible at admitting when it’s wrong, it has no concept of human relationships, and it will schedule a meeting with a robot named Tyler without a second thought.

But.

It was surprisingly good at triaging support emails (it just needs stricter rules). It caught two billing errors I’d missed. And the auto-generated weekly report was genuinely useful — once I stopped it from adding “strategic alignment milestones” that didn’t exist.

The takeaway? AI can’t run your business. But it can handle the parts you hate — as long as you don’t let it schedule meetings, talk to clients, or discover cheese marketing.