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"Bro, they quoted me 40K in legal fees… lol more like Prompts"
That's a founder I know. He decided to make his “legal team" a $20 ChatGPT subscription. The other side's lawyer is a lawyer.
You already know how this ends.
I get it.
Legal bills are obscene, and AI reads a 60-page agreement faster than any associate alive.
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But marking up documents for a $5M deal with $150M edits is not "leveraging AI."
Trying to get AI do 100% of your legal work is like letting "100-hour MS Flight Sim guy" land the 747 with you in it.
Opposing counsel is laughing at you.
What's your AI going to say when you get sued for $87 million?
"Sorry, that one's on me"
AI is great. It's just not great at being a lawyer, and carrying the legal responsibilities that come along with screwing up.
Why founders get hosed on legal
- They paste the purchase agreement into ChatGPT and treat the output like a signed legal opinion. (it isn't)
- They ask ChatGPT if the contract is "safe to sign," and it says yes. (it says yes to everyone)
- They pay $600/hr for an NDA that came out of the firm's template folder in 4 minutes.
- They tell their lawyer to "handle it," then open a 5-figure invoice on a deal that hasn't moved in 6 weeks.
- They hire the famous firm instead of the one a founder actually vouches for.
At least one of those is you.
The fix: know which jobs go to AI, which jobs go to the human, and how to manage the human so the bill stays sane.
What AI is actually for
Forms yes. Approval no.
NDAs, boilerplate docs, board consents, a first-pass summary of the credit agreement you were never going to read: let AI eat it.
That's the work junior associates used to bill $300/hr to copy-paste anyway.
My general rule: if a mistake costs you an afternoon, AI takes the first pass. If a mistake costs you the company, it goes straight to an attorney.
Specialized legal AI can push that line further than ChatGPT can, but the line still exists.
And no, a detailed prompt doesn't change the math. The other side hired someone with malpractice insurance.
What a lawyer can do that AI can't
The good ones bring value beyond the deal: intros to capital partners, lenders, the operator who sold a business like yours last year.
A great business lawyer is a Rolodex with a bar number.
So hold them to the same criteria as anyone joining your business: what do you add beyond the job description?
If the answer is "I mark up documents," AI already does that. (cheaper, and it doesn't bill $500/hr for it)
4 rules for hiring lawyers
1. Keep the budget down. Lawyers need to be actively managed.
If you let them "just do their thing and figure it out," expect it to be extremely expensive and take a LONG time.
Scope every engagement, cap it, and ask what's burned every week.
2. Founders make deals, not lawyers. My rule on every deal: "We figure out how the deal works, draw it up in a one-page summary, and get the lawyers to paper it."
It's your JOB to do the dealmaking.
Abscond from that duty and it gets VERY expensive: 2 associates negotiating business terms neither of them understands, at $500/hr each.
3. Know which kind you're hiring. There are 2 kinds of lawyers: those that find problems, and those that find solutions.
Both are useful, in opposite situations. In litigation you want the problem-finder who goes slow and makes it painful for your opponent. On a deal you want the solutions lawyer who gets you to a close.
Hire the wrong one and watch your deal die of a thousand "concerns."
4. Ask experienced founders for a referral. Press them for first-hand experience.
A founder friend worked with an extremely well-known business law firm and was thrilled, at first. When I asked her for an intro later: "Don't work with those guys."
I pressed. They'd massively overbilled for junior work, messed up her cap table, and more.
The brand name protected exactly nobody.
AI takes the first pass. You make the deal.
The founders getting this right stopped paying anyone to do the wrong job.
AI drafts the routine paper. A tightly managed lawyer papers the real deal. And you decide what the deal actually is.
Mix those up, and the $87M lawsuit stops being a joke.
Your call.
Reply with the worst legal bill you've ever opened. I read everything.
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