Aaron Levie is the founder of Box. His company is worth $4 billion. 64% of the Fortune 500 runs on his platform. He’s been close to enterprise IT decisions for two decades.
Last week he said this on a podcast:
“If your company is more than 5 years old, pre-AI, your data is all over the place. You’ve got 30 different systems. Your workflows aren’t documented. That spells opportunity — it’s kind of an up-for-grabs market right now because of how much work there’s going to be.”
Read that again. He’s not talking about Fortune 500. He’s describing every small and mid-sized business in Central Florida.
What he’s actually saying
The headline story about AI is the tools — Copilot, ChatGPT, Claude, the new feature your software vendor just added. The actual story is the gap underneath.
Every business older than 5 years has the same shape. SharePoint folders that nobody owns. A webmail inbox a long-tenured employee runs on the side. Three personal Microsoft accounts that quietly hold company data. A workstation someone’s nephew set up in 2019 with the admin password on a sticky note. No directory. No MFA. No offboarding when people leave.
That’s not a failure of those companies. It’s what “doing the work” looked like for twenty years. But the AI tools you’re being sold right now can’t see through that mess. You can pay $30 per user per month for Copilot and it’ll feel useless — because it can only see what your environment lets it see.
Why this matters in 2026
What’s changed: the cost of the cleanup is now the cost of competing.
Your competitor down the road who actually gets identity, file structure, endpoint management, and offboarding right — they’re not just better organized. They’re the only ones who can actually deploy the AI tooling that the rest of the market is talking about. The owner who skips the cleanup gets the line item without the leverage.
Aaron’s phrase was “up-for-grabs market.” He’s pointing at the consulting and managed-IT firms that do this cleanup work. The 10-person shop in Minneapolis. The MSP in Central Florida.
The unglamorous list
Here’s what actually pays off. None of it is exciting. All of it is required before any AI conversation is real:
- One identity provider, MFA enforced, every employee on it. No more personal Microsoft Live accounts holding business data.
- Files where you control them. Not in personal Gmail. Not in someone’s local Documents folder. Not on a USB stick.
- Workstations managed centrally — patched on a schedule, baseline configured, EDR running.
- A documented offboarding step. When someone leaves, you can revoke their access in under an hour, and you know what data left with them.
That’s it. Four things. Most Central FL businesses we walk through are missing at least three of them. The fix doesn’t require a $200K consulting engagement. It requires somebody to actually do it, and a partner who won’t disappear after the install.
Watch the full conversation
Why I’m writing this
iTech Plus has been the partner doing this work for ten years across hundreds of Central FL businesses. We didn’t need Aaron Levie to validate it. But hearing a $4B founder describe the exact thing we walk through on a typical Tuesday afternoon — for an audience that historically thought “this is just IT housekeeping” — that lands differently.
The market just figured out the foundation matters more than the features.
If you’ve been wondering why your AI tools feel underwhelming, or your team keeps asking for ChatGPT subscriptions while nothing seems to actually save time, the answer is almost always one or two of the four bullets above. Fix those, and the tools you already own start to do the work you were hoping for.
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