Miguel Simon

Apple's iOS 27 is putting AI automation into every iPhone — not just Siri, but woven through the entire operating system. Scheduling tools, intelligent summaries, drafting assistance, workflow shortcuts. All native. All built in.

Most business owners will update their phone and not notice. That's not cynicism — it's the pattern I see every time a major platform releases new tools. The capability shows up. The behavior doesn't change.

The businesses that will actually benefit aren't the ones with the newest phones. They're the ones willing to stop for twenty minutes and figure out which three things in their day they could hand off to a feature they didn't know existed.

What's one task you'd hand off to your phone if you knew it could handle it reliably?

Meredith Whittaker from Signal said something this week that's easy to miss in the noise: AI chatbots are not your friends. She said it plainly, without drama — because it's just true.

The companies building these tools have a business model built around your engagement. The longer you feel connected, the longer you stay. That's fine for a social platform. It's a problem when you're making a business decision about where your money goes.

For small business owners evaluating AI tools right now, the only question that matters is: does this do the job? Not does it feel impressive in a demo — does it handle the specific task, reliably, at a price that makes sense? If the vendor's pitch is heavy on feeling and light on specifics, that's your answer.

What's your criteria for evaluating an AI tool before you commit? I'd genuinely like to know.

Snap spun off its AI video team this week into a separate company. The reason: building cutting-edge AI tools internally was too expensive, even for them. One of the biggest, most well-funded tech companies in the world just said out loud that they can't do it all.

That story matters more for small business owners than most of what's being written about AI right now. Because the pressure in this space is relentless — adopt more, build more, automate everything, or fall behind. Snap just quietly proved that pressure is a lie, even at the top.

Focus beats scope every time. Knowing what you actually need — not what the industry tells you to want — is a competitive edge most businesses never use.

What's one AI tool or system you've felt pressure to adopt that you're still not sure you actually need?

The pressure on small business owners right now is real, and I want to name it directly. If you don't automate, you risk falling behind competitors who do. If you do automate, you may be replacing someone who has worked for you for years.

Tens of thousands of people are losing jobs to AI right now. Many of them aren't at big corporations. They're the chat agents, the receptionists, the part-time customer service reps at businesses just like yours. This is not distant news. It's local.

Here's what I've found working with SMB owners on automation: the ones who do it well are honest. They sit with their team before they install anything. They explain what's changing. They find new roles where they can. They don't pretend the change isn't happening, and because of that, they keep the trust of the people who matter most to their business.

How are you thinking about AI adoption in your own business, and what's the hardest part of that conversation to have?

KPMG, one of the largest consulting firms on the planet, just had to pull a report because their AI made things up. Not exaggerated. Not slightly off. Made up.

Here's the part that should matter to every small business owner watching this. The mistake wasn't that they used AI. The mistake was that nobody checked it before it went out the door.

I spent three decades leading people before I ever touched a piece of automation software, and the lesson is the same one I learned back then. Checking someone's work, or something's work, isn't a sign you don't trust it. It's how trust gets earned and kept.

If you're using AI in your business right now, whether that's for emails, reports, or an AI receptionist answering your phone, build in the second look. The technology is good. It's not the final word.

What's one place in your business where AI output goes straight out the door without a human checking it first?

This week, the U.S. government forced one of the biggest AI companies to pull its most powerful models offline — overnight. No transition period. No backup plan offered. Just gone.

For the thousands of small businesses that had built their entire operation around that one tool, Friday morning was a scramble. Clients calling. Deadlines unchanged. The system they'd spent months learning, suddenly unavailable.

I think about that a lot, because I've lived a version of it. Not with software — with life. Twelve years of raising two sons with autism taught me that the ground you're standing on can shift without warning, no matter how solid it looked the day before. The lesson wasn't to stop building. It was to build in a way that could survive the shift.

If something you depend on disappeared tomorrow — a tool, a client, a plan — would the rest of what you've built still stand?