I Never Wanted to Start a Business. Then AI Changed What Was Possible.

A few says ago, I was a guest on Entrepreneurs On Fire — one of the most-listened-to business podcasts out there, with millions of downloads and a host (John Lee Dumas) who's interviewed thousands of entrepreneurs.

And there I was. A guy who, until recently, swore he'd never start a business.

The topic was AI. But the conversation kept circling back to something I hadn't fully articulated before: why my "never entrepreneur" mindset might actually be an advantage in the AI era, not a liability.

The Never Entrepreneur Advantage

For years, I was the person who wanted stability. A steady paycheck. Someone else worrying about whether the company would make it. The idea of starting something from scratch felt reckless. Too many unknowns, too much risk.

Turns out, that instinct is actually useful right now.

Here's what I mean: the dominant narrative around AI is very "move fast and break things." Automate everything. Ship yesterday. Figure it out later. And sure, speed matters. But the people racing to implement AI without understanding it are creating messes they'll spend years cleaning up… hallucinated data in customer communications, biased outputs in hiring systems, confidential information leaked into training sets.

The cautious mindset is exactly what AI implementation needs right now.

When I built Fox + Spindle's AI readiness assessment (3,500 lines of HTML, written by a guy who doesn't know HTML), I didn't ship it in a weekend. I spent 40-60 hours with Claude and ChatGPT, testing edge cases, breaking things intentionally, asking "what could go wrong here?" at every step. Not because I'm a perfectionist, but because my instinct is to poke at something until I trust it.

That's not a weakness. That's due diligence.

The entrepreneurs who'll win with AI aren't necessarily the fastest. They're the ones who understand what they're building, know its limitations, and can explain to a client or customer exactly why they should trust the output. The "never entrepreneur" brain, the one that needs to feel safe before taking a leap, is wired for exactly that kind of careful, trust-building work.

My business partner Jenny and I jumped into Fox + Spindle without a single client lined up. That felt insane at the time. But we'd already done the work of understanding AI deeply, pressure-testing our ideas, and building something we genuinely believed in. The leap wasn't reckless. It was calculated.

If you're someone who's always thought you're "not entrepreneurial enough…" — too cautious, too risk-averse, too prone to overthinking — consider that maybe the game just changed in your favor.

Why "AI Access" Isn't AI Adoption (And What That Reveals)

On the podcast, I talked about the pattern I see constantly: a company rolls out AI access, sends an email ("Here's ChatGPT, go be productive!"), and calls it a day.

Then they're surprised when adoption is inconsistent, results are messy, and half the team has quietly stopped using it.

This keeps happening, and I've been thinking about why. It's not just laziness or budget constraints. It's a category error. Leadership genuinely doesn't understand that AI is a fundamentally different kind of tool.

(which explains the abundance of weird AI images and the scarcity of outcomes)

Behold, a totally real photograph of a fox in a blazer

Think about the last few decades of enterprise software. CRMs. Project management tools. Spreadsheets. All of these share a key trait: predictability. You click a button, you get a known result. Training is basically "here's where the buttons are." The skill is navigation, not judgment.

AI breaks that model completely.

Generative AI doesn't have buttons that do predictable things. It's probabilistic. It generates novel outputs every time. The same prompt can give you three different answers, and the "best" answer depends on context that the tool can't fully understand on its own. Using it well requires judgment, iteration, and a mental model of how it actually works.

That's not a software training problem. That's an education problem.

But most companies don't have a framework for that. Their entire technology adoption playbook is "give access, provide documentation, let people figure it out." That works when the tool is predictable. It completely fails when the tool requires a new way of thinking.

What this reveals is kind of uncomfortable: most organizations don't actually have a culture of learning. They have a culture of access. And for most of the software era, that was fine, access was enough. AI is exposing the gap.

The companies that will actually get value from AI aren't just rolling out tools. They're investing in genuine education. They're teaching people how generative systems work, what they're good at, what they're bad at, and how to evaluate outputs critically. They're building judgment, not just providing access.

This is a huge opportunity for anyone in the training, education, or consulting space. But it's also a wake-up call for any organization that thinks "we gave everyone Copilot" is an AI strategy.

It's not. It's just access. And access without understanding is how you end up with people either misusing AI in dangerous ways or abandoning it entirely because they couldn't make it work.

What This Means for You

If you're an entrepreneur, especially one who's felt like you're "not the type," here's what I'd take away:

Your caution is an asset. The AI gold rush is creating a lot of noise and a lot of broken implementations. The people who take time to understand the tools, test them rigorously, and build trust-based offerings will outlast the hype chasers.

Education is the gap. If you can teach people to actually use AI, not just access it, you're solving a problem that almost every organization has and few are addressing well.

The ceiling is higher than you think. I built a complex technical tool without engineering skills. Not because AI is magic, but because I was willing to spend 60 hours learning alongside it. The question isn't "what do I know how to do?" anymore. It's "what do I want to do?"

Jenny and I started Fox + Spindle because we saw this gap between AI access and AI competence everywhere we looked. We assess where organizations actually are, train their people properly, and help leadership understand what they're really dealing with.

Now we're bringing that approach to entrepreneurs. We're launching an eight-week live program called "Start Smarter with AI" for people who want to build a business but don't have the big budget, the technical team, or the MBA. We used AI to launch our own company, from registering the LLC to building the website, and this course is everything we learned, packaged for a live cohort.

If that sounds like your kind of thing: foxandspindle.com/how-the-fox.

And if you're still on the fence about whether you're "entrepreneur material," maybe give yourself a little more credit. The game just changed, and the cautious ones might finally have the edge.