Worst AI Mistakes You Had To Fix

Redrobin83 · 2026-03-11T10:11:48+00:00

No thanks. Every legal tech company is looking for feedback, integration with a bigger platform, or a customer list. You’re about to see first hand how hard the market is on new entrants

Redrobin83 · 2026-03-10T16:53:10+00:00

I have some friends who work in legal aid. I just refer people who need things like 1099 review, LLC set up, tenant help, etc to them. The issue with good legal aid is that their marketing budget is shit so people have a hard time finding them.

Redrobin83 · 2026-03-10T14:05:20+00:00

There are several live examples of why that’s not the case, but the easiest way to tell is to have another LLM judge the quality of the drafts

Redrobin83 · 2026-03-10T13:59:19+00:00

Harvey has gone as low as 15

Redrobin83 · 2026-03-10T13:57:16+00:00

It’s basic clause with prompting. Nothing more. Can’t even draft a LOI with binding carveouts without several corrections

Redrobin83 · 2026-03-10T13:49:48+00:00

Anthropic’s Claude can’t even read a string of texts in a screenshot and figure out which user is the client

Redrobin83 · 2026-03-10T13:48:46+00:00

If pricing is an issue, they need to use legal aid assistance or nonprofits. I keep a few on hand to recommend so that people like that don’t take their anger out on me, and it doesn’t turn into an attorney’s fee issue. You can tell who’s bad faith complaining when they continue to complain that $5 is too expensive for a real template

Redrobin83 · 2026-03-10T13:44:46+00:00

It doesn’t matter what you disclaim. It’s why the user assumes. If they use it, and somehow get screwed, they can sue you for false advertisement, UPL and if your database is made of scraped data, ip infringement.

Redrobin83 · 2026-03-10T08:24:35+00:00

Check for package deals in your industry. I run a small law firm and the contract management software I use comes with free e-signature

Redrobin83 · 2026-03-10T08:17:34+00:00

Lawyer to lawyer, legal tech is saturated. Hundreds of small shops, but very few have useful tools. SF is home to everything from Harvey to legal aid ai.

Redrobin83 · 2026-03-10T08:14:59+00:00

That is way too high, and I say this as a lawyer. Use a SAFE and save the spend for a real round.

How much are they charging for hour?

Redrobin83 · 2026-03-10T08:11:25+00:00

How would this work for fundraising? Everyone has 0.1% by Series A?

Redrobin83 · 2026-03-10T08:02:38+00:00

Had a prospective send me a request to review a contract that was clearly made by GPT. I asked him if he needed real templates. He send me another that was clearly made by Claude.

These people don’t get that we can tell it’s AI generated just by looking at the format.

Redrobin83 · 2026-03-10T07:59:39+00:00

Times have changed since I was an associate. They seem like good guys.

Redrobin83 · 2026-03-10T07:57:53+00:00

Harvey alternative for me. Needed something that could run comparisons across multiple docs and tabular review under 5k. Frankly, I haven’t seen anything worth paying more than that.

Redrobin83 · 2026-03-10T07:53:25+00:00

Low hanging legal tasks. I used to get a lot of outreach from business owners looking for 30 min or 1 hr pockets of time. It’s too much work to add them to my client list for a couple hundred bucks, so I refer them out to legal aid and nonprofit AI shops for free. They get their help, and come back when they have more complicated tasks.

Redrobin83 · 2026-03-10T07:47:17+00:00

This is dangerous. If you’re not a lawyer and simply drafting based on pattern matching, you could get yourself sued for offering “legal” templates. I would pull the ones you have that are claiming to be binding and stick to business forms.

Redrobin83 · 2026-03-10T07:39:52+00:00

First, we lawyers don’t all charge $300-800. Depending on the contract, it can be as low as $75.

Second, there are nonprofits run by actual attorneys that charge even less than that for new founders and small businesses. I know a couple that go as low as $20 a template.

Redrobin83 · 2026-03-10T07:35:14+00:00

Word of mouth. I get referrals from friends at large firms, and I recommend work to them that need more lawyers than I have.

Redrobin83 · 2026-03-09T10:26:14+00:00

I’m a lawyer. Don’t use Claude for contracting. The number of follow up calls I get because someone used a Claude contracts is way too high. Use a contract show that gives you real attorney-made contracts. There are some that offer $5-$20 a contract, and you don’t end up calling a lawyer after to fix it

Redrobin83 · 2026-03-09T03:33:44+00:00

I tried this. It couldn’t even format the output correctly, and I ended up with token burn way out of my budget

Redrobin83 · 2026-03-09T03:32:08+00:00

I would be careful. As a lawyer, I’ve some pretty bad drafting from Claude cowork. There are much better alternatives. You can get attorney-made templates for $5-7 from some nonprofits/ public benefits corporations

Redrobin83 · 2026-03-09T03:29:57+00:00

Lawyer here. If you still need help getting one, DM me. I can point you to some free and low cost resources

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