Using GPT To Stay Unf*kd, A Series: Pt1

Every founder needs something that keeps them clear when the room gets blurry.

For me, that’s GPT.

It helps me identify red flags in real time before people can chime in.

The Setup

I used GPT to help me negotiate that an outside party would cover the cost of our legal counsel’s scope of work.

It took nearly a year until that party agreed in writing (as GPT insisted I get) to cover our legal bills.

GPT had flagged the risk early:

So I made sure the paper trail existed first.

Then I looped in our (Tier 1) outside counsel to execute.

Counsel replied:

GPT Red Flag #1: “Taking the liberty” = acted without authorization.
GPT Red Flag #2: “Calling [outside party]” = blurred who they represent.

One Week Later

Counsel kept asking me to stop emailing and call instead.

GPT Coaching: In the old world, this made sense and standard protocol. In the new world, documentation is your advantage. This language in this particular instance suggests an attempt to move communication off record. Keep everything in writing.

So I did.

A Few Weeks Later

I asked counsel for the invoices they’d billed the other party which, under the firm’s own standard billing protocol, should already have been sent to and cleared by the paying party at that point.

Here’s what came back:

GPT Red Flag #3: “Conditional upon closing” = a term that doesn’t apply.

GPT Red Flag #4: Counsel appears to have discussed and decided on new payment terms without the company’s (my) knowledge or consent.

GPT Red Flag #5: Silence when asked to clarify = absence of accountability.

GPT Red Flag #6: These payment terms conveniently explain why outside counsel was relentlessly trying to get this transaction across the finish line — they wouldn’t get paid otherwise.

(Note: in the world before GPT, I would have read this and believed it at face value…that I did something that caused me to have to pay this bill instead of the external party who was responsible for paying it...in fact in the pre-GPT world, I allowed people to manipulate me into paying tens of thousands of dollars in fees exactly like this lawyer just did above…by assuming I didn’t know enough to spot the red flags.)

The Move

GPT and I reviewed the logic line by line, mapped inconsistencies, and produced this paragraph:

Crickets.

Will I ever work with these parties again? No.
If you’re a founder and want to know who I’m speaking about so you can avoid them, will I tell you? Yes.

The Learning

GPT isn’t a lawyer. It’s a clarity tool.

It separates fact from assumption and makes visible what used to be invisible: the ways information asymmetry powered entire relationships.

There was this funny thing that happened when GPT entered my workflow, a kind of fog lifted.

I realized that the same counterparties I’d been working with long before GPT — people more seasoned, more resourced, more experienced — kept engaging with me exactly as they always had.

They didn’t adjust at all for the next two years post-GPT.

And that’s when it became painfully obvious: their advantage was never experience. It was opacity.

GPT removed that opacity.

The veil lifted, and what was left was a room full of people who suddenly had nothing to hide behind. No jargon, no hierarchy, no illusion of knowing more.

Will using GPT in this instance come back to bite me? Possibly.
Will writing about it? Maybe.
Was it the most cautious path? No.
The modern path? Yes.

It’s a new era.

GPT doesn’t just open up new tools. It brings old tricks to light.
And once you can see the light 🪔, the leverage over you is gone for good.

Happy Diwali.

Kaeya