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Excellent blog post, excellent advice. This part in particular:

> When working with paid professionals, I think people tend to put them into one of two categories: doctors or general contractors.

> With doctors, if your oncologist says you have a lump that needs to come out, you pretty much do whatever they say. You’re the patient; they’re the expert leading the charge.

> With general contractors doing home renovations, most people intuitively know that’s not the right approach. You stay on top of them, give clear instructions, try to understand the issues yourself, and assume you need to provide lots of direction and monitoring to get what you want done.

> Most people—entrepreneurs included, certainly myself—put lawyers in the doctor category when they should really treat them more like general contractors.

Except... I think if one has enough time, it's better to treat everyone like general contractors. Doctors make mistakes, often. You can and should challenge them.

> Doctors make mistakes, often. You can and should challenge them.

The problem with challenging doctors is that the body is incredibly complex, and is not really under any obligation to "make common sense" / be bro-science-y.

The vast majority of the time you're going to be wrong and annoying, even if you're consulting LLMs first.

If a doctor is making a mistake, and you're a lay-person, you're not likely to spot it. But you are likely to challenge a bunch of things that the doctor is right and just be an annoying back-seat driver.

You're better off trying to get a doctor you can trust than treating your doctor like someone who isn't good at their job.

There are bad and shady doctors to be sure, but they are extreme outliers.

Doctors, unlike lawyers, typically care about your care - whereas lawyers are mostly interested in extracting as much of your money into their pocket as possible.

Unless you're going to some elective surgeon, most doctors are so busy, they don't need to make up pretend bs to have you come back and get work.

Lawyers on the other hand...

Two separate doctors have almost killed my wife with incorrect diagnoses over the span of 15 years.

She had cancer when she was 18 and the doctor insisted that women just don’t get cancer at that age, and insisted the lump was benign without testing it. We got another doctor to remove it, and it turns out it was stage 1 cancer.

A decade ago she was in crippling pain right in the gall bladder area. The doctor insisted it was indigestion. We found another doctor (thank goodness for PPOs letting us go directly to specialists without a referral) who did an ultrasound and said my wife probably had less than a week before she would suffer a rupture, and she had to have emergency surgery.

I’m glad you haven’t had that experience, but it’s a very real problem.

The inverse of this is people blowing off doctors then dying from very preventable illnesses, which I wager is orders of magnitude more common.

That's not to say that you should just believe doctors. If someone is telling you something isn't a big deal but you think it is, then get a second opinion.

It's especially common for women, particularly young women, to not be taken seriously. The implication is that young people are healthy, and women are over dramatic. Well... they're not always. I, for one, got cancer in my 20s.

The reason, I think, doctors are like this is because they want to err on the side of caution. They don't want to put people on medication unless they're 100% sure. They don't want to put people through anxiety-inducing tests for kicks. They don't want to cut people open unless it's the absolute last resort. And I can understand that mentality to a degree.

Not true in my experience. Just because a doctor has gone to medical school doesn't mean they are good at debugging/troubleshooting. I've had many doctors try to diagnose my chronic issues with guesswork and hunches instead of methodically eliminating possibilities with tests. I had to switch doctors many times to find one good enough to diagnose my condition (LADA aka type 1.5 diabetes). I actually asked the first doctor if it could be LADA and he said "nah, I don't think so", so then I asked if we could test for it to rule it out and again he declined and confidently encouraged me to exercise more and eat fewer carbs.

It's surprising how bad most people are at debugging. They make hypotheses but don't test them in isolation, so they can't reach conclusions. I see this everywhere, from IT issues to trying to fix a broken vacuum cleaner.

There should be a specific course on boolean logic in high school, distinct from math. Doesn't need to last a year; but needs to be graded separately from everything else.

The irony is how transferable these actual skills are, and often how intangible they are (difficult to measure, in a sense).

A few really good programmers/IT types I've worked with over the years were also very handy at auto repair, home repairs, and the like.

I guess, for a vague description, "root cause analysis", "isolation of the issue", and "reproducibility" are vitally important skills across domains.

My only "skills" in these domains are software stuff and some auto repair/troubleshooting and the process is nearly identical.

So you found a doctor to agree with your preconceived diagnosis and he's the one who is right, while the others were wrong?

You're intentionally ignoring the part about tests and methodical reasoning vs guesswork so you can be snarky about someone's take.

No but one of the things doctors learn is that when you hear hoofbeats, think horses not zebras.

It's not practical to test for everything right away, and if an adult is overweight and presenting with diabetes you initally treat for type 2, and advise losing weight and changing diet.

Every medical school class has people who graduate near the bottom. The critera for entry, and the filters that you have to pass before you can practice as a physician means that even those people are generally decent doctors.

I'm not saying doctors are never wrong but you're not likely outguess even an average doctor by googling your symptoms. It's very easy to convince yourself you have some rare condition because your symptoms match, but you ignore "rare." The fact that someone has an anecdote to the contrary doesn't change this.

In my case I am very skinny (150 lbs, 6'0") which is the main reason that I thought I might have LADA and not T2 - my own research suggested that T2 was rare in skinny patients and that LADA might explain my elevated blood sugars (and also that up to 12% of T2 might actually be misdiagnosed LADA). So IMO the horse should have been LADA. However, LADA doesn't seem super well known or understood among doctors that haven't worked with a lot of pre-diabetic patients. This particular doctor claimed that my A1C would have been much higher than it was if I had LADA/T1 and that I was exhibiting symptoms of insulin resistance. I tried to argue that maybe we were catching it early and that insulin resistance and insulin deficiency present with the same symptoms (high blood sugar), but the doctor suspected I was non-compliant with the requested low-carb/exercise regiment and told me to try harder instead of ordering the tests and that I would see results if I did that.

I went to a second random doctor I found on ZocDoc who also thought I was T2, but then LADA was eventually confirmed by a third doctor who I chose specifically because he's worked with a lot of diabetic and pre-diabetic patients. He took one look at me and said "You look too skinny for a typical T2, let's run a GAD-65 autoantibody test", which came back 10x higher than the normal rate.

So yes, if you are a doctor and you hear hoofs I do think it's a good idea to think horses not zebras, but also if you've never actually worked with zebras, maybe have the humility to defer to a different doctor or listen to the patient who clearly has done more research than you about the condition they've struggled with for years instead of confidently pushing your wrong theory.

P.S. Early on in the process I also tried to see an endocrinologist (who probably also would have recognized LADA). However, they are a gated resource. I was unable to set an appointment with an endocrinologist without a recommendation from my PCP, and my PCP wouldn't give one. Just frustrating all around.

This is a much better comment with some thought behind it and a point at the end and without the snark. Thanks for adding it.

Any good doctor will tell you that you should be an advocate for your own care. That includes asking questions when something does seem right or doesn't make sense. You don't have to be a doctor to tell them they marked the wrong limb to be removed in surgery or ask why they recommend one treatment over another.

> Doctors, unlike lawyers, typically care about your care

Yes but doctors, like laywers, often err on the side of caution. I don't want to be cut open unless absolutely necessary.

Maybe the approach is simply to ask for a second, expert opinion rather than trying to make your own. But asking pointy questions can't hurt (within reason, of course; you don't want to be the guy "doing their own research" (even if you are)).

You sound like someone who was lucky enough to only meet good doctors.

Bad doctors, that really don’t give a shit, exist and are doing well, at least where I live, because there simply isn’t enough doctors.

The ratio good to bad doctors is the same as good to bad contractors in my experience.

I fully understand how annoying it is to be challenged by a patient as a doctor but why would the doctor do that with his contractor and not accept that from the patient? Because he’s more of an expert? I’d argue he’s less of an expert actually, because medicine is so insanely complex and we know so incredibly little of it.

This approach seems more like an overreaction to bro-science/anti-vaccine crowd. Like you arrived here by deciding to trust doctors more, since others don't trust doctors enough.

Often, you get out of something what you put into it. People who don't try to understand their own health/relationships/finances often end up where they didn't want to be.

If you won't advocate for yourself, why should you expect a 3rd party do it?

Topical: "How I Built an Open Source AI Tool to Find My Autoimmune Disease (After $100k and 30+ Hospital Visits) - Now Available for Anyone to Use" --> https://www.reddit.com/r/OpenAI/comments/1ij6619/how_i_built...

I'm in the UK. As well as doctors making mistakes, they can be under direction diagnosing critera. The UK has had a multi-year struggle for people with ME/CFS, (Myalgic Encephalomyelitis/Chronic Fatigue Syndrome). It falls under neurology in the UK, and a sub-chapter neuro-psychiatry has the ear of the national health service's supremos, and has historically entertained an "all in the mind" approach. I digress. Back to AI and medicine again: https://x.com/vipintukur/status/1931049593535627417 - insights can come from that quarter, and medicine is going to have to play catch up at times.

> Doctors make mistakes, often. You can and should challenge them.

It is worse. Many doctors will administer against your interest if it boost their bottom line. There is, also, very little legal recourse against doctors.

This. Doctors have to work in a system. The hospitals are institutions that have quarterly quotas to hit, and they want doctors to maximize profit. How much the doctor will oblige depends on the individual doctors but the pressure is always there.

I read the same and came to the opposite conclusion. I said: "Yikes. The balls on this guy.":

> Some lawyers bristle at clients setting strategic direction. They believe there’s a “correct way” to do things, they know it, and they’ll fight you if you disagree. In that case, get different lawyers.

The thing is -- there are correct ways to do things in the legal sphere. Litigation is highly professional and highly formal, and has only become more so. While sub rosa it's fine to ask an AI for advice, and to engage it in draft brief writing, summarization to bullets, etc., it's wild not to realize how much of litigation and the law is wrapped up in people and experience and intricate formal processes. Such as this court has local rules, and this judge likes his briefs this length and the arguments just so, this needs to be filed here, stamped by the clerk, and filed again over there.

AIs may be exceptionally clever, but they may misunderstand the theatre of a trial. They may overweight the importance of the law and then underweight human factors, like the importance of assigning blame, or the lack of credibility of certain witnesses, or the bad faith of certain actors. AIs may fail to give credence to the ordinary meaning of terms, or fail to emphasize that these are two sophisticated businesses which understand the technical terms. AIs are still very poor at actual "reasoning", that is, a deep consideration of the multitude of ways of looking at any one set of facts and/or words on the page.

One area in which this article is entirely right is -- one must manage attorneys, and you must make certain that legal costs don't become leverage against you. But there are points at which you say: Can this guy keep it all straight? Does he know how to be useful to his own defense and then does he know how to get out of his own way?

Lawyers shouldn’t set the direction because they tend to try to minimize liability at the expense of everything else.

CPAs shouldn’t set the direction because they tend to want to structure your business in ways that save taxes, at the expense of everything else.

If you’re the CEO/President of your company, you should set the direction, using lawyers to know what the liabilities of the different options are and using accountants to know what the different tax implications are. Lawyers and accountants help you make informed decisions, but they should not be deciding the strategy.

> The thing is -- there are correct ways to do things in the legal sphere. The legal sphere is highly professional and highly formal, and has only become more so.

In some ways. OTOH, my wife works in the legal sphere, and after spending most of her career at a small boutique firm before being subsumed by a larger one, she was kinda dismayed to discover that there’s no singular “right way” to do things, and that different lawyers kind all do their own thing in a multitude of different ways.

> different lawyers kind all do their own thing in a multitude of different ways.

Agreed. There is no formal processes to the inner workings of firms (but perhaps there should be).

What I think the author is saying is: There is no single way to conduct the lawyer-client relationship. Agreed, as well. But what I am saying is: There are certain areas in which the client can be a detriment to himself by ignoring the ways legal processes function.

Like -- "I am certain if the judge only hears what I have to say re: X, she will immediately dismiss this frivolous suit. You must tell her about this now. You must file something now." Okay, lawsuits are governed by highly formal processes, and there may be a time and a place for such merits arguments, at certain points in the suit, but this may not be that time. This is the time we talk about process, like jurisdiction, etc.

The correct procedures are why you (and the OP) need a lawyer in the mix.

Strategic direction, though, isn't something that has a correct mechanism. That strategic direction can include things like how hard you want to fight on each motion and if/when you want to try and settle and for how much.

Said another way, if you approach a plumber with "I need more hot water" they'll probably try and sell you an industrial tankless water heater with a nice markup. However, if you tell them "I want you to install this water heater that I purchased" then they'll do the work to get it fit in and setup. 1 option will cost you $1000s of dollars more. There is still a correct way to install water heaters, but the stuff related to whether or not you need a new water heater and what kind shouldn't be left up to the plumber.

The law is the same way. If you just tell a lawyer "I'm being sued, help me" they can justify putting any amount of time researching case law for your case. Taking a more active role, though, and saying "this is how I want you to respond to that motion" will shortcut a lot of that research time. They'll still have to do some work to validate you aren't giving them garbage to file. And of course they are still expected to follow all the local rules. But the actual billable hours will be massively reduced because they aren't doing nearly as much research.

> Taking a more active role, though, and saying "this is how I want you to respond to that motion" will shortcut a lot of that research time.

Taken literally however "this is how I want you to respond to that motion" could be wildly reckless. I think your discussion above amounts to equivocation on the word "strategy". It's fine to set business "strategy". Telling an attorney what should literally be in his response to a motion, ignores all his/her knowledge about motion practice, the law, and evidence which will be relevant to the question. Like -- this is a 12(b)(6) motion, not a motion for summary judgment. We are questioning the sufficiency of the claim on the page, not whether there are genuine issues of material fact.

Business strategy is "don't spend gobs of money on this motion" not "file what I tell you."

> could be wildly reckless

Could be, which is why you have a lawyer to put guiderails on and give a "are you sure you want to go down this path?".

> Telling an attorney what should literally be in his response to a motion, ignores all his/her knowledge about motion practice, the law, and evidence which will be relevant to the question.

No, because before a lawyer files the response they have to (well, they should) both read, understand, and verify that it is in fact a valid response to file. Not doing so can get them sanctioned.

It's also their job to bring up to the client "Look, I know you want to file this but in my experience you'd really be better served if you did this instead".

> Could be, which is why you have a lawyer to put guiderails on and give a "are you sure you want to go down this path?".

Guardrails are the wrong way to think about the relationship. The attorney is not your mother and you are not a toddler. The attorney is not there to figure out the 1000s of different ways for you not to get hurt, when you present them with a bogus response. Why? Because verifying the 1000s of ways for you not to get hurt is often a waste of time which will cost you time and money itself.

A better way to think of the relationship is a partnership. A: I feel business needs to do X. B: I think X with a few addendums stands a better chance of success, but will cost a few dozen deep research hours, which likely can't be handled by AI. A: Can you cap my cost at $Z? B: Done.

> No, because before a lawyer files the response they have to (well, they should) both read, understand, and verify that it is in fact a valid response to file. Not doing so can get them sanctioned.

Simply being formally valid is not enough. Most clients want to have a reasonable chance of success?

Moreover, attorneys like doctors, shouldn't simply be considered instruments of your desires. Especially in litigation contexts where they have other independent duties to fulfill. Attorneys, for instance, are not allowed to simply ignore adverse precedent.

A: The AI said X and Y and Z. B: That's fine, but we need to be sure we have addressed the relevant case law in this jurisdiction. A: The AI was last updated a week ago. B: Afraid we have to a deeper search than Claude.

> The attorney is not there to figure out the 1000s of different ways for you not to get hurt, when you present them with a bogus response.

They are, because they are a partner with you in law. Part of their job is working with you and looking out for your best interests.

> Because verifying the 1000s of ways for you not to get hurt is often a waste of time which will cost you time and money itself.

That verification is what you are shortcutting but also not what you are after. You want their experience to be able to say whether or not a path is good. The fact is, there's no 1 right way to do things and what you really want is "is this reasonable".

> Most clients want to have a reasonable chance of success?

Most clients want to pay the least amount of money possible, including legal fees (In civil cases). "Success" isn't really measurable beyond "will this bankrupt me".

There's also not a lot of guarantees that this motion or that motion will ultimately drive down the cost of the case. There are literally thousands of motions that get field especially when talking about corporate lawsuits.

> However, if you tell them "I want you to install this water heater that I purchased" then they'll do the work to get it fit in and setup.

Yea, but plumbers tend to hate this. Electricians and HVAC pros also don't like it when you sit in the driver's seat. Car mechanics, too. When you've already done the diagnosis, and you just want them to install this OEM fuel pump which you've already purchased. Some mechanics will even refuse the job. They want to pump their bills with hours of diagnosis and their parts markup.

Tradesmen have a process they want you to go through that maximizes their revenue.

I disagree with your sweeping statements. Tradies fear crappy clients, but if you're pleasant to work with and you pay them fairly and you don't shit on them then you can find good tradies that will work closely with you.

Pick your tradie, to suit your requirements, and be a great PM and pay for quality work. I've been the Purchaser, Project Manager and often the apprentice/gofer too (saving myself many many billable hours of cost on each job).

The last three multi-thousand tradie jobs (builder, plumber, electrician) I've had deep interaction with the tradie and I am a repeated client with significant different jobs with each.

Properly respect the person, be ultra-polite if you want to question how anything is done. Never micro-manage or be an overdemanding perfectionist and accept normal mistakes. They are the experts but they sometimes get things wrong.

You are an apprentice trying to learn, but you can be firm with requirements and watch for gross mistakes.

I often get involved with other tradies or professionals too (recently car electrical, car mechanical, medical specialists, fencer). Sometimes to save money, sometimes to get job done better.

If you want to be OCD about a job, then pick an OCD tradie and be prepared to pay for your perfectionism. I'm usually more cowboy. One friend is a tiler, and he likes delivering amazing jobs (but he costs somewhat more per hour than average).

> and you just want them to install this OEM fuel pump which you've already purchased

Recently just done similar with my mechanic (supplied wheel studs and they've told me where to get replacement handbrake cable which they'll fit), and I did this with my electrician (used my own reels of cable) and I wish I did this with my plumber (because I would have made a better choice of fitting than they did). For cheaper jobs perhaps pay them for the lost income (trade discount or trade markups are usually known, or you can just ask). Actually did this with a fuel pump with the second hand car dealer when they had to fix under warrantee (helped simplify things to get their mechanic to fix car while I waited).

Context: I'm in New Zealand and I'm in my 50s.

On-topic: when you're a founder you need to hone the skill of working with professionals (e.g. lawyers) and getting them to do work right. My take on being a founder is that you are ignorant about everything but you have to get it done anyway: you often have to become your own expert and just do it (your meta-skills are most relevant). Advisors/mentors often lack context or have their own agendas, so you just gotta get ahead regardless of your ignorance. Learning how to listen to advice, pick the value out, and throw away the dross is just hard. Being submissive or falling for status plays is ruinous.

Not disagreeing about the risks of AI here. But the thing is, there are correct ways to do things in court. But this guy's strategy was to improve his negotiating position, pre-court. That sounds like it's a lot more to do with assessment of risk, assessment of your adversaries strategy, and business position. Which are all matters that totally aren't solely the province of lawyers. In effect, that means that the lawyers should have been doing what he got the AI to do.

> in court. But this guy's strategy was to improve his negotiating position, pre-court.

"The court" generally just means stuff that involves a judge. Not the actual trial. There is no "pre-court" really.

Whenever you and the opposing side have a disagreement, a judge will be involved to determine who should do what. That's what filing motions are all about.

For example, in a deposition, your lawyer is going to ask the opposing side 1 million questions. While asking those questions their council will pretty frequently say "objection". Each time they do that, they can go back to the judge (court) and fight over whether or not that line of questioning will be admissible into evidence in the trial.

The guys strategy is around the motions and briefs filed. It's not infrequent that a judge will ask each side for a brief about the current legal state and why their motion should be granted. That's where mountains of lawyer money can be spent. Every hour they spend researching the caselaw around a motion they get to bill you.

But further, strategy involves how often you fight the other side. There is an endless amount of stuff lawyers can argue over which ultimately does not (or barely does) affect the final outcomes. Being able to tell your lawyer "No, don't fight this motion it won't really matter" is where money can be saved.

Every expert will tend to miss the forest from the trees because it's their job, and mission, and billing criteria, to find every possible tree and categorize it. But you and I don't care about the trees, we only care about the forest.

There's this comedian who tells the story of his grandmother aged 97 who was diagnosed with cancer, and they offered her chemotherapy. She said: what's the point? Are you going to prolong my life for an hour? That makes people laugh, but it's the truth, and it's also, I think, the point of the post.

The point of defending a lawsuit is not to be right, and die. It's to survive it.

It worked for Steve Jobs!

Jobs didn’t do this part correctly:

“try to understand the issues yourself”

Your contractor is a skilled professional, not a drone. You need to exercise good judgment if you’re going to make decisions.

That's my point: are you sure you understand the issue better than your doctor, who has over a decade of training? In most cases, it's easier to find a good doctor than to learn enough to outguess your bad one. Devote your efforts to learning to select the doctor.

You need to be informed to know which doctor is better. I generally try to follow the advice of my family doctor, but that’s because I’ve made an informed decision on past experiences where I double checked him.

But that’s easy with a doctor you have a long term relationship with. I imagine it’s different eg. if you get cancer it’s probably going to just be a part time job to keep informed on all the doctor’s recommendations, and getting second opinions sounds like it would be time prohibitive. I don’t know of an easy way around this though.

You don't need to be informed because the beauty of second opinions is that you have a statistical advantage. Meaning, if one dude is telling you something, he could be wrong. If two are... well you might want to listen. 3? 4? What are the odds they're all idiots?

Yep, i'm pretty sure every kind of patient, from a cancer patient to someone with an ingrown toenail has googled their condition, looked for alternatives (especially if the proposed treatment was subjectively bad for the patient, even if it was objectively good).

People tend to skip the googling and verification process only if the problem is something simple or if the treatment is simple... eg. broken outlet, for legal reasons can't replace yoursefl, call contractor, outlet replaced... or in case of doctors, fever, infection, blood test, it's bacterial, antibiotics, two pills per day for 10 days, done.

There is actually a significant portion of the population that wants nothing to do with it and wont even google their cancer diagnosis and leave it up to the experts.

You should in that case at least get a second opinion.

Also, just an FYI for anyone in here, there are people that call themselves doctors who will diagnose and cure cancer using magic. Any "clinic" that staffs a number of naturopathic doctors (NDs) and suggests that you can treat cancer with dietary changes is a grift that should be illegal.

I'm dealing with cancer in my family and one such clinic was the first suggestion by family members. This isn't the place, but it what to watch out for [1]. Always be leery when you see clinics downplaying traditional medicine. Notice on their staffing page that they have exactly 1 doctor on staff (not even a nurse practitioner) and that this doctor doesn't have any credentials in oncology. And if you check out the billing section, notice that they instruct you on how to commit insurance fraud. There's a reason they don't take medicare/medicaid and it's because committing fraud there is a jail sentence for them and you. For a large insurance company, it's a lawsuit to you.

Edit: Ah, found the actual place suggested to us [2]. You can see a lot of the same hallmarks on it vs the first link.

[1] https://brio-medical.com/

[2] https://www.envita.com

completely agree. there are doctors who were bottom of the class or who are not updated with the latest research.

My wife went through this.

We had a doctor that had prescribed us a dangerous amount of medicine (we didn't know) without running any tests. The doctor was also doing procedures he didn't need to do and ultimately recommended a surgery that has been stopped since the 90s.

We caught him because of the surgery. We sought a second opinion about it because the google was telling me "This surgery is no longer performed because it has serious negative consequences, and it rarely treats the symptom it's done for". I even double checked with the quack that it's the surgery he wanted to do because I was a bit flabbergasted he was suggested it (he was, of course, annoyed that I looked it up).

We sought a second opinion and I've never seen a doctor angrier. First, he was livid that the doc had us on such a mega dose of the drug and wasn't doing bloodwork to confirm we even needed it. But also, he was furious the doctor wanted to do the surgery. I'm 90% sure he got the docs' license pulled because the quack sent out a sad "Sorry to inform everyone but we'll be closing up shop".

Needless to say, always always look up the procedures and medications doctors want. Second opinions are also a good thing and good doctors will respond with "The more the merrier". And don't be like us, you should be thinking at all times "what test did the doctor do to determine we should be doing X". If a doctor is freeballing shit, you should be leery. Except maybe if they are throwing Tylenol at you for pain. [1]

[1] https://www.youtube.com/watch?v=gD6olRJ8S3I

I agree with you. I think it comes down to the fact that you have to “live in the house.” Whether it’s a doctor (where the house is your body) or a general contractor (where the house is a house), at the end of the day, nobody cares about the house more than you do.

I wonder if it's really that rare for lawyers to look at a case from a strategic / economic point of view? When at some point in the past I was considering suing a company for breach of contract, that was pretty much what the entire initial conversation with our lawyers was about: they considered the timeline, probability of winning, costs for the lawyer'ing, costs for external experts, ability to recoup legal costs if successful or to incur those of the counterparty if not, ability of the counterparty to pay, alternatives to litigation and so on.

After about a day of prep work on my part, having them read through that prep work for about an hour and then discussing it with me for another hour, we concluded that the expected outcome was break even, with a time investment that was decidedly not break even, and did not proceed to litigation. They really helped our company to look at the problem objectively and without emotion, and I really hope that's not a rare experience!

(That said, I do understand that strategies for successfully dealing with being sued might need to get a bit more creative than those for deciding whether to sue.)

I also had an experience like this, where we found a great lawyer who basically explained to us the social dynamics of the particular arbitration court that the legal battle would be fought out in, and how if we can establish a paper trail that just made the guy suing us look like he was acting in bad faith, that it would be hard for that guy to make his case. Then our lawyer helped us craft emails without being emotionally involved like we were to socially engineer this outcome, and then came out with a nice settlement at the end once his lawyer convinced him that he was in trouble.

I think finding these people is a dark art, but they exist.

It is not rare (among competent counsel, at least).

You seem to know what you're doing, but for other readers, the time to think about breach of contract and litigation, and the time to talk with your attorney, is before you enter contracts and business dealings. An ounce of prevention is worth a pound of cure, but many mistakenly consider prudent consultation and planning to be a waste or a drag on the bottom line.

> It is not rare (among competent counsel, at least).

While this is true lawyers are still lawyers, and you're paying them primarily to give you legal advice. The best will be able to also consider wider business perspectives, but at the end of the day they're still going to have a bias towards doing what is safest from a legal perspective which you need to weigh up against other risks for your business.

Going back to the point in the parent article, educating yourself on the legal side so you're going into the discussion on a more equal footing is a pretty good idea in general.

> strategic / economic point of view?

This is very much what you want from a BUSINESS lawyer. And what the author apparently didn't understand. You, your business, the other guys ideally - nobody in here should be there for ticking boxes and the exact details of the law. What you are sorting out with a business lawyer is business issues, which need to be resolved in pragmatic business terms. It's not a legal puzzle but a business puzzle.

Same thing from the point of view of writing a contract, or writing or answering a demand letter: The point is to solve a business problem - not satisfy some ideal of the law. And the business lawyers you want do understand this and can be amazing at finding the right terms and shortcuts and at helping you come to an understanding of what matters and doesn't. And yes, these lawyers very much exist.

People often argue that it's a lawyer's job to point out and try to protect you against anything that could possibly go wrong - with the result that indeed it's impossible to run a business. No, that's not the job.

But it takes time to find a great business lawyer, so this should be part of the tasks right from the beginning when founding a business. That lawyer won't cost all that much initially - and they will already be useful working on contracts.

Same thing for in-house corporate counsel, when you get to that. Some amazing ones who can defuse a situation in an instant - and others who spend their life making things impossible.

Now, it might get to the point where the business lawyer helps you understand that all alternatives have been explored and it's time to spend serious money on courtroom litigation specialists - but hopefully that's only seldom.

>I wonder if it's really that rare for lawyers to look at a case from a strategic / economic point of view?

I'd say it's more likely that they're aware that their client simply isn't going to like the answer.

If a client is all fired up about wanting to sue someone you can caution them to reconsider, but at some point they'll just go "fine I'll find someone who will do what I tell them to". Litigation doesn't put people into an open & receptive mindframe normally.

I dunno about the US, but every lawyer I've ever hired was like this. Maybe it's more regulated in Germany or something. They run the math with you and find the optimal strategy (or the least bad one), not create a black hole of costs towards an uncertain outcome.

Professional liability carriers and disciplinary counsel generally frown on attorneys not giving their all. They are expected to be zealous advocates.

Re: Zeal As lawyers, as part of obtaining our professional liability policies, we have to attend seminars about mitigating malpractice claims. You'd be surprised how often --an attorney advises A, --the client wants to do B, --the attorney advises the client of the downsides of B, and has the client sign a document stating they understand the risks of B, --they do B, and have a sub-optimal result, --client sues attorney claiming they should have done A, and they weren't adequately informed of the risks of B.

Zeal is, in many jurisdictions, an outdated concept and standard. Even where it still exists, other considerations outrank it — such as candor to the tribunal.

I think this article really buries the lead—what really allowed him to win was leverage. He says that’s an over beers info, not a blog post. But that’s actually what let him win—not learning from the LLM how to understand his lawyers arguments better.

> not learning from the LLM how to understand his lawyers arguments better

The leverage came in the form of reducing costs. When you ask your lawyer to explain, they happily bill you for that time.

OP told you what he could in a public forum and left out a few things for private. Its only fair.

The incentives are against you. Lower costs lets defendant fight it out longer with less $$ for lawyer. Law firm isn't spending more hours to earn less. So you gotta have a friend with this skill and a vested interest or do the legwork, which OP suggest AI was for him.

I don't agree AI had a significant part to play here. The leverage, whatever it was isn't likely to be public. Certainly wasn't AI as the title suggests.

I feel the headline is clickbaity.

The seemingly valuable advice was on how to handle lawyers who fail to see your big picture interests rather than just winning the case.

I agree, it made me hesitate to share because I think it's the least interesting part of the story

Agreed. I really struggled to find the actually useful info here. But that’s it. Have leverage and use it in some unspecified way

This is the reason I think the 'AI' angle of the post is less interesting than how he came to understand the power dynamics and strategy of the situation. Maybe AI helped him reach that point, but it could easily have been a lawyer friend or family member playing that role

Because the point was how he used AI, not the actual leverage.

In my case, I used small claims when a contractor took my money and didn't perform work. The threat of losing a lawsuit was enough to get the money back.

I suspect the plaintiff did something that would allow Tyler to countersue, or otherwise there was some kind of threat of negative publicity / tattle to other customers.

Developers and lawyers have a lot in common. In the end, we write rules that are interpreted, whether a machine or a judge.

Therefore I think the same things apply as in software development, when you start to think you can fire lawyers and replace them with AI: you will then bear the responsibility of the job they did before. That means it can go the right way, but it can also go the wrong, wrong way.

Funny you should phrase it this way. One of the better self-taught software engineers I know had a prior career as a defense attorney. When I had the privilege of working with him about ten years ago, he used to say "legal arguments are kind of like code that you run on a judge, instead of a CPU".

Gives a whole new meaning to ‘illegal operation’.

I had the same reaction when I had a will made. "If this case, do this; if that case, do that; otherwise do such-and-such"...

Although without the timing conflicts. :-)

The notion of a smart contract (as implemented by blockchains like Ethereum) makes the difference between a legal contract and code even smaller: the [Solidity] code IS the (unambiguous) contract.

Unfortunately “smart contracts” are missing two key features that real contracts have: a number of squishy conditions required to make them valid, and the ability to have a judge determine that a contract is not legally unenforceable even if otherwise valid.

To me AI in law seems better since you have a judge at the end. If you get something wrong it'll most likely be fine. There seems to be some tolerance for mistakes when representing yourself so it's most likely helpful for small claims and fighting tickets/fines. In a perfect world people wouldn't be paying BS fines or letting people scam them because they can't be arsed to take 2-3 days to deal with it the first time (once you've done the spiel once it's much easier).

Would make more sense if it was not written in a natural language such as English, but Lojban instead. It is not ambiguous at all (but can be made). The difference is that natural languages are naturally ambiguous, whereas Lojban is not, but can be made so, for poetry or whatever.

Every language is ambiguous. There's a gap between language (description) and reality. No formal logic can bridge this.

https://www.lojban.org/files/why-lojban/whylojb.txt

Legal English isn't natural English.

I do not see how a subset of English could be called unnatural, as opposed to Lojban.

Good points. But the main point of the article was not about replacing lawyers with AI - rather it was about using AI to be an informed client and thus work more in partnership with lawyers.

right, and the same thing is true when hiring software developers as a non technical[*] person. you need to make an effort to understand what the devs are building and you need to guide them to work towards the goals you want to achive and the constraints you have (budget, time, etc). if you don't they will focus on things that are not important and you will spend more money than you planned on a solution that doesn't quite fit your needs.

(*) as a technical person too, but then the understanding part takes less effort and you can skip using AI to do it

Absolutely. I'm working on a "legal IDE" for this exact reason.

In the US, our system of lawyers is broken. If we are to be a People governed by laws and not persons, then we People need to be able to use the law to right wrongs. In other words being able to use the law by using the courts is a requirement in a democracy.

As an experiment try to go to court pro se. The experience is characterized by the fact that in US courts, pro se clients can be sanctioned for improper actions, but lawyers can not be sanctioned for purposeful improprieties by pro se clients.

It is sort of like a commoner going up against a knight. The knight has armor and a lance and you have your scythe. Fun! In other words it is rigged.

And here is the kicker. Lawyers are "officers of the court". You could take that to mean that they uphold the standards of the court. Or when a lawyer does bad things, that could mean that the other lawyers - including the judge - see that lawyer as one of them. You know, sort of the way that many priests see abusive priests as priests first and abusers second, and so take actions to "protect" the church.

So whats a poor person to do? You try to get a lawyer. Lawyers will not want to take you on if the other side has a high power lawyer and lots of money. Not because your case isn't proper, but because the economics are not there. For the lawyer. At some point the side with more money will simply run you out. Your lawyer will urge you to settle.

Again this is not an us vs them thing. The issue is that if common people cannot afford to obtain justice, then we are not a democracy. We are something else. Corporations and the ultra wealthy have deep pockets to use the courts. If we tolerate that, it is reasonable to expect that the common people will not find this kind of "democracy" to their taste.

The problem is that corporations pushed for Tort law as a mechanism for protecting the public from harm rather than regulations “if we do something wrong, we will get sued and lose money and that will motivate us to not do harm”. So it means that there is much less proactive harm reduction by regulators (compared to many other first world countries) as well as much less regulators can do if a complaint is made.

The second issue is our lack of universal, affordable healthcare (and other basic safety nets). If you are injured and don’t want to go bankrupt, you have to sue to pay for your treatment, loss of income, etc.

The result is that we have lawsuits constantly all the time for everything. Not only does it clog up the courts, but it also helps the powerful to outspend “the little guy” to avoid accountability. Fighting a government regulatory body with actual powers and authorities is much harder to outspend/outlast than some random person one lawyer working on contingency.

And that doesn’t even get into how corporations have been pushing “tort reform” to neuter how much they can be sued for, therefore the amount they can be punished for wrongdoing. As well as their decades long propaganda campaign to paint tort lawsuits as frivolous, baseless, shameless cash grabs by greedy people attacking the poor helpless business.

Yes. It seems to me important that we correctly understand the problem. It is like your car won't start. If you fail to diagnose your battery is dead, then you keep putting gas in and it still doesn't work. The question is what needs to change to fix the problem AND why.

My diagnosis is Citizens United vs F.E.C. That bizarre has allowed corporations to control the laws that are enacted. So we see "tort" reform - but who benefits? It is not the People.

There is another factor that amplifies this, targeted advertising. Targeted ads, you know like the ones that pay for our "free" internet services are as toxic or more than the pollutants in coal and gas. They have destroyed trust in the internet. And they allow corporations to "fund" candidates for public office.

And question. Do the media such as the Washington Post, owned by Amazon's Jeff Bezos, address these issues? Nope.

Thank God I've never been involved in serious litigation, but his description of the process sounds absolutely wild to me. Reminder that the US is a global outlier in 'loser doesn't pay winners' attorneys' fees' (as he notes, this is literally called the American Rule). And a global outlier in using juries for civil trials, which can lead to some gigantic unpredictable judgements. I'd imagine our discovery laws are unique too.

Surprised some business-friendly US state hasn't greatly restricted discovery in civil litigation, so as to attract companies to incorporate there. And this is why arbitration rose as a way to settle disputes- if you look at the standard arbitration agreement they greatly limit discovery

It cuts the other way as well. It's incredibly easy to file suit against larger corporations (e.g. your landlord in small claims) and just represent yourself and be confident all you're potentially out is the court filing fee. I've personally done it twice and settled before it went to trial; without the American rule there would be no way I could risk having them take it to trial and pay their fees.

Without jury trials how do other countries with judicial indepence prevent the growth of corruption in the judiciary for civil cases?

(or influence peddling, political horse trading, etc…)

Sane countries do not elect their judges by popular vote (or, even worse, by their executive branch), and thus judges are generally apolitical, which removes a lot of incentive for the issues you mention.

It's insane to me that the US accepts that their judiciary are either 'red' or 'blue', and that their opinions are dictated by their tribe.

Seems like a non-sequitur. 'Corruption' is typically not an issue in civil disputes. 'Influence peddling' and 'political horse trading' are not the subject of civil litigation. If you think 'corruption' is influencing judicial remedies- it's certainly a lot easier to bribe a juror than an appointed judge.

Most developed countries using a panel of judges to hear civil disputes score better than the US on corruption indicators, not worse

A panel even of just 3 judges seems a lot more expensive to operate than 1 judge and a dozen jurors?

This article has good advice but it’s not really AI advice that’s the important tip.

The main observation is you 100% have to manage lawyers aggressively and understand and question what they are doing at literally every step or the budget will be out of control. Sounds like AI helped this guy but it’s more about your personality/approach than anything else.

Also don’t hire $1000 an hour lawyers for litigation unless you’re a major corporation in a complex case with a ton at stake.

I think the AI advice is pretty important. You say you should understand and question everything the lawyers do but where do you even start without an AI to read and explain thousands of pages of contracts and legal process. Nevermind all the case law and it's trained on and has access to.

I think if he tried this ten years ago he'd have a pretty hard time with it.

If there is no attorney-client privilege with AI (I believe there is not), then could the opposing party demand discovery of all of one’s communications with the AI pertaining to the case?

Lawyer here. There isn’t attorney-client privilege with AI itself because AI is neither your attorney nor your client. However, there is something called the work product doctrine that shields things like your activities with legal research tools, document review tools, etc. so long as they are used in anticipation of litigation. So, despite what the other commenters are saying here, there is pretty much no chance that any of this would be discoverable, barring very strange circumstances.

That said, it would have to be disclosed via a privilege log. You would probably wind up having to disclose what documents you uploaded. Your prompts and the responses are probably protected work product.

I'm curious where the line is if you represent yourself in a criminal case. At what point (if any) would opening up Google Docs and typing notes about the case that inadvertantly incriminates yourself become inadmissible?

Let me preface this by saying that civil procedure and criminal procedure are separate bodies of law with their own rules on these issues. I’m not a criminal attorney and thus not comfortable speaking out of field. That said, I know there is an analogous work product doctrine that applies to pro se criminal defendants, but I don’t know the contours of it.

It’s super interesting to think about though! Imagine if your Google Doc said something like “The stolen cash is hidden in these six places, but the prosecutors don’t seem to have anything linking me to some of those areas, so I should point that out at trial.” If the government didn’t already know where the cash was hidden, it seems implausible to me that any judge wouldn’t let them have that information. It likewise seems implausible that the judge would let the prosecutors know what the defendant thinks would be good or bad to emphasize at trial. So I’m guessing it’d be an in-camera review resulting in a redacted document just disclosing the places where the cash was hidden, but not the subsequent mental impressions. But the real question, as you asked, is whether you can actually put that in front of a jury to show guilt. And I’m afraid I’m going to have to plead ignorance here (but hope there are some criminal attorneys lurking on HN that could speak to this).

I don't have an answer to this- but if the above answer was based on the Federal Rules of Civil Procedure it may not apply to criminal cases at all. (And the above was probably a generalization that assumes parties in California or some other state the lawyer was familiar with.)

Better advice would cover exactly what's needed to maximize that odds of that determination. For example, commingling the 'research' with activity that is the subject of the ligation may make your life much harder (or at least more expensive) because your opponent is absolutely entitled to that other material at the very least.

It also doesn't help when your opponent hit the provider ex parte with a subpoena and they just served it up which I can speak from experience many providers are pretty eager to do. Maybe after the fact you get an order for your opponent to destroy and not use the material but if you're dealing with a party that was dishonest enough to bring a frivolous claim in the first place that may not be that comforting.

The interesting question - if the AI is provided via my lawyer's office - is there privilege in this case?

There's no privilege, so yes, if the AI chats are retained, they may be subject to discovery.

This is completely wrong, as the other commenter stated. This would certainly fall under the work-product doctrine [1,2], where documents prepared for the purpose of future litigation are protected from discovery and could be considered analogous to attorney-client privilege (but is actually much more broadly defined than attorney-client privilege[4]). Even if opposing counsel is able to obtain discovery on a work-product, only fact based products, not opinion based are allowed. In other words, the court removes anything related to “mental impressions, conclusions, opinions, or legal theories of an attorney or other representative of a party concerning the litigation” [3]. For conversations with AI about how to conduct your case, that would exclude basically everything since it is an opinion work-product, not a fact work product. A fact based work-product would be things like “statements or interviews of now deceased witnesses, photographs or video of an accident scene taken at the time of the accident”[4].

[1] https://www.floridabar.org/the-florida-bar-journal/the-work-...

[2] https://en.wikipedia.org/wiki/Work-product_doctrine

[3] https://coxlawflorida.com/florida-rules-of-civil-procedure/r...

[4] https://tenthings.blog/2019/06/05/ten-things-a-primer-on-the...

Thank you

even for say google search histories?

Theoretically yes, if the court can be convinced that it is relevant to the case.

> Upload Everything to AI Projects.

Unless you're using an ephemeral on-prem LLM that doesn't keep logs you should begin with an assumption that your AI chat transcripts will be available to your opponents in discovery. There isn't clear caselaw on this yet, but given that material you share with third parties other than your lawyers almost always is and sharing your strategy musing would probably be disastrous, you should plan accordingly.

Particularly, subpoena are quite powerful in the US and can be obtained quite easily and often without an adequate opportunity for the ultimate user to oppose them. The AI providers will comply with them as just a matter of process, and the first notice that an opponent is seeking your transcripts may be after they already have them. (And that's assuming your opposition doesn't have insiders at the AI company to begin with...)

That aside-- Having thoroughly dispatched an AI dependent opponent in court, uhh, well lets just say that I hope any future opponents read this article. ChatGPT outputs an astonishingly embarrassing amount of completely wrong pseudolegal nonsense and set him up for multiple case losing disasters.

There are also a number of advanced strategies available to an opponent who has realized you are using an LLM, as they now have oracle access to something similar to your own AI advice and can test their actions against the advice it will cause you to get from your AI. ... even so far as brute force searching rewrites of the language in their correspondence to increase the odds that you get disastrous advice.

> There isn't clear caselaw on this yet, but given that material you share with third parties other than your lawyers almost always is and sharing your strategy musing would probably be disastrous, you should plan accordingly.

Wouldn't this have largely been settled already with cloud computing? If I use gmail to write an e-mail to my lawyer, then I can't imagine that e-mail is unprivileged because it's "shared" with Google.

Oh, that's entertaining. If you're using AI as your attorney you have no attorney - client privileges.

US discovery law is wild.

An aggressive litigant might claim the AI was essential to assist the founder in communicating with counsel, and thus similarly protected to some degree. This is coming up in search results as an "agency" rule and the founder still would need reasonable expectations of confidentiality from Claude, etc.

There are legal research AI's and tools out there, which sophisticated non lawyers probably use. Discovery rules haven't been a deterrent because of the companion work product doctrine which is an adjuct to the American Rule-- you generally can't use discovery to extract legal research from the other side.

When lawyers speak of the American Rule, we mean the concept that each party pays for its own legal fees unless that default is changed by statute, contract, or court action (for example, sanctions) — as opposed to the English Rule, under which the losing party generally must pay the prevailing party's fees.

Even in most American jurisdictions, the losing party ends up paying many of the prevailing party's costs (deposition transcripts, expert costs, etc.).

- Use an AI that don't keep any records

- Delete that data as per your retention records

(there's also the fun alternative with feeding believable but slightly wrong info to the AIs and let the opposite council chase loose ends)

Right but with cloud services, you can't control their retention and settings to not retain almost always do retain but deny you access to it. They'll still serve it up in a subponea even when they won't give it to you.

Watched an expat video on youtube recently where he said he would never go back to America because the legal system is effectively lawless. Reading things like this, and others, makes me agree. There is this idea in America that countries with Civil Law systems instead of Common Law are more dangerous, but are they really more dangerous than "the law doesn't actually mean what it says, it means what this judge said 80 years ago it says"? The financial asymmetry just makes it worse, wealthy people and entities can very easily lawfare their enemies out of existence.

I used ChatGPT Project folders extensively to deal with my landlord and the rental contract due to problems with the windows. Things went from the landlord saying "maybe they'll be fixed in 2 years if you extend your contract" to "I've called a contractor and am waiting on a quote, should be done in a couple months". I'm not well versed in UK law or how to speak/write "properly" nor have the fortitude to parse long contracts and laws, ChatGPT handled it well enough for me to get what I wanted.

I think we'll soon see "this doesn't look right, <inserts location tagged photo>, figure out who to report this to and do the things" as a service.

I'm not even talking about lawsuits, but all the situations where you can report things to the government, but it's so much hassle that most people won't even bother. Things like labor / safety violations, violations of data protection and anti-spam laws, improper parking, that sort of thing. If reporting those could be as easy as complaining and posting a photo on Facebook or Instagram, a lot more people would do it.

Did you learn anything about navigating such waters? It's not likely the first time you'll have to deal with a grumpy landlord or leasing contract.

I am all for using whatever tools we have at our disposal to get things done. I use GenAI to automate/speed up a few tasks in my personal and professional life as well. However, the danger is plain; if I didn't already know how to do those tasks, I'd be leaving myself in the dark as to how they actually got done. As you can imagine, this just furthers what I call Dependency Culture, where we are at the mercy of having our decisions made for us because we don't understand the process.

There's a lot of (perhaps unfair) poo-pooing on GenAi, and I am guilty of it myself, but the fact remains that while it does make certain things like navigating a complex legal contract accessible to someone who is unfamiliar, the aim should be to use it to get familiar with said subject, ultimately reaching a point where the GenAI is no longer needed.

Honestly, I just wanted the windows fixed.

There's a lot of mental cycles being expended on "how to avoid going to court over contract litigation" when the answer could be provided by a bog-standard forum selection clause requiring arbitration from a template last updated in 1992 or indeed a chatbot; but you would have to ask it the right question.

Looking up the lawsuit in question but without reviewing the record, it looks like this was probably as much personal as it was business. This always makes cases a lot harder to settle. When it is just business, you can almost always work it out in numbers. When you screw over a wealthy man in a very personal and humiliating way, your contract case can become like divorce, which is only good for the lawyers and for no one else. Ask the chatbot to summarize "The Prince" for you and maybe this will be one of the points that it gives you.

I think the major point is that if you fancy yourself a beginner businessperson, sooner or later you will have to find some professionals you can trust. Regardless whether that's a lawyer or an accountant. Doing business will have its costs, and you will not necessarily pay those costs in the way you can anticipate.

Maybe you pay those costs before you sign a contract, and avoid a jurisdiction in a contract that you have no connection to (if you can). But you will definitely pay these costs when you have to litigate. If you think Claude or ChatGPT is the best answer to this, and all you need to know is using advanced voice and upload documents, I believe that's not that useful piece of advice.

Please bear in mind that it's not just particular case law that these tools hallucinate. They give incorrect advice in very different ways how humans do. If you can find a lawyer you can trust in a jurisdiction you're interested in, and you got along with him/her quite well, you can trust them for as long as they're in business, even if you never pay them once again. And they might even give you referrals or point to other professionals, understanding your budget and situation. Of course, they can still give you bad advice, they can become gambling-addicted, and run away with your money. It happens, even if very rarely.

But with LLMs, you won't know when they hallucinate, and what they get wrong. Even if you have the full statutes and case law uploaded and updated, it will give you wrong answers as well, but they're not working in the same way as humans do.

All we know that it's more likely to give you incorrect advice in jurisdictions not being covered by their training data (like outside New York or Delaware), and it will draw incorrect inferences in other cases from materials it has seen. Usually only lazy lawyers not reading the output will face the problem of incorrect case law.

But legal advice is not like coding where you can filter out most of the incorrect answers with tests and compilers. The author have happened to chose the wrong lawyers for the first time. I accept that not everybody has reliable lawyer friends qualified in Delaware, but in terms of advice, it would have been more practical to discuss the possible directories to use, beginner's methods to select lawyers, warning signs to look out for etc. It's sad that many lawyers act for trolls and do bad faith litigation. It's even worse that bars have no methods to exclude and disbar such guys. But you cannot avoid these problems by trusting a cheap AI tool instead, that's just wishful thinking.

My reading of the article is that it has nothing to do with the author's trust or lack thereof for their lawyer. I think the author would agree that you have to find a lawyer you trust, just as you need a doctor you can trust.

I trust my doctor, and if it's a minor issue like needing antibiotics for something I just accept whatever they prescribe. But if it was a life or death situation I am not going to blindly follow their advice without any questions. I ask my doctor for their recommendations but I make the final decision. They may disagree with that decision but ultimately it's my life at risk and I'm the one who suffers the consequences. As long as you are reasonable and not trying to cure cancer with fruit I hope that the majority of doctors are going to support this.

When it comes to drafting contracts or other minor issues you should just trust your lawyer. But if the lawsuit has the ability to completely end your company I think it would be a mistake to do the same. But I'm not a founder so maybe my opinion isn't worth anything here. I've only hired a lawyer once for a landlord-tenant dispute, my lawyer gave their recommendations, I disagreed with it, and they said alright it's your money, but it ultimately worked out so we were both happy. I find it interesting that the author had trouble at first finding a lawyer who would agree to this arrangement because that wasn't my experience.

If you're going to do this, you need to do your own research beforehand. In my case I read all the relevant tenant laws before I even met with the lawyer. Today I might use AI to help with that, but I would be wary of hallucinations. I think the majority of the article is about this: just using AI to help with research before meetings with your lawyer.

At the end of the article the author says they are now using AI to draft legal documents and I don't agree with that but that's just me.

> drafting contracts or other minor issues

This is (unintentionally) hilarious. The drafting of a contract is hardly minor in many, if not most, situations.

"Minor" was a poor word choice, I'm not sure what word would have been better. My intention was to say that I don't see how a non-lawyer could have any reasonable opinion on how a legal document is drafted. That is also why I don't agree with the author about replacing that with AI. They absolutely should weigh in on overall strategy because you need to consider factors such as your company's finances, risk tolerance, etc. In the same way that you might decide with your doctor that you want a surgery done but you have to trust them to do the surgery properly.

An interesting post by Tyler Tringas about being sued as a founder. Obviously there's an AI angle to this post, but I also found it an interesting look in to the power dynamics of civil litigation in the US.

In a previous post [0] they talk about the impact of the litigation, which seems to have contributed to the shuttering of his fund

[0] https://tylertringas.com/code-concrete/

The two top-level replies to this give some flavor if anyone is interested in the details: https://news.ycombinator.com/item?id=40661478

Simply put, this person hired the wrong law firm.

When you get sued, you get a reasonable amount of time to respond. That includes time to interview firms, discuss the approach and goals, and then choose the best firm that will attempt to carry it out. And then that firm will have enough time to write and file the response. Of course, you have to start immediately.

A good litigator wants to give the other side their bar number, and have them shit their pants when they look up their litigation record. It’s absolutely a strategic advantage; milking hours and aiming for a settlement is bad for a litigators career.

This doesn't make sense. A good litegator is expensive, and as me tioned in the article an important part of the strategy behind this lawsuite is bleeding the defendant dry with legal expenses.

Telling the other side that you have an expensive lawyer just gives them more leverage.

Did I somehow miss the conclusion of the piece? I was hoping to finish with reading about how AI found that “one simple trick” to get the case dismissed or won and also recover costs.

They used AI as a tool to compellingly direct the legal team to move as quickly as possible to a reasonable settlement, rather than protract the process. The AI didn't save them from litigation, it saved them from unnecessarily long litigation.

Thank you!

It's about 2/3rds in, and then the author gives some tips and does some other musing.

Look for "My AI Legal Research Workflow", and if you really want TLDR, go to "The Cost Arbitrage Advantage"

Thank you!

A friend of mine is regularly mentioning chatGPT as is lawyer.

Given many countries share the same language, I am struggling to understand how he make sure chatGPT is not hallucinating and that he is basing his advice on the laws of the correct country.

It will direct you to the law and language if you ask.

A problem not so easily solved here is the difference between the law and reality. Where the LLM is completely blind to which laws are actually enforced in a proper manner.

Trust but verify. It will come up with ideas and claims, google all that for authoritative sources and people who went through all this. Ask again for anything contradicting you can find and ask for edge cases you can think of. Change the wording and ask again to see if it gives you the same advice.

IMHO hallucinations are not that bad when you have a human in the loop.

I think the term is "confabulations" now, which makes a bit more sense to me, but regardless of what we call the hallucinations, it starts with the human knowing how to navigate the process, having at least some basic understanding of the system within which they're using the GenAI (in this case, law/legal) and the skills to cross-reference and verify without using the GenAI itself. If we start using the GenAI to both get the answer and verify it, we're basically creating a feedback loop that probably isn't always going to stand up to scrutiny, despite the fact that GenAI has gotten quite good at these sorts of things.

We're not there, yet, but we will be, probably within our lifetime.

> google all that for authoritative sources

With Google progressively replacing actual websites with AI-generated results, you might come full circle to having Gemini validate the same hallucinations the Gemini app produced in the first place.

> The Delaware legal system is fundamentally broken for defendants. Due to the ironically labeled “American Rule,” even if you win, it’s extremely rare for the other side to have to cover your attorneys’ fees

Another reason not to blindly use Delaware

There are 49 other states, a district, territories, and various native reservations, with their own incorporation statutes

They haven’t all just sat idly over the last 30 years in the competitiveness of their statutes

Some even have Chancery Courts just like Delaware

And the lack of case law is actually a benefit. If you don’t like Delaware’s case law you can argue for a completely different ruling that only benefits you. while if you do like Delaware’s case the local judge has a strong incentive to lean on it and you can push for that.

Its surprising how uninspired people are about this, especially ones that arent raising capital

I don't know that this is a particularly good article, but it touches on two elements of games based on incomplete / imperfect information.

One of these elements he refers to as "leverage" and I think he does an ok job explaining what it is, although maybe not how / why it works.

The other one, contrasting doctors and contractors, I think he does poorly. Full disclosure: I've had really crappy luck with doctors (it's not just luck). Doctors aren't used to getting "not to exceed" demands, things like that. On the other hand my father was a psychiatrist, a specialist, and that gives me insight into the "practice" of medicine; and I've worked for a number of biotechs and I have some insight into the evolution of medical practice. Combined, I have a pretty good sense of when the doctors are "practicing" versus forming a hypothesis (ask for one!).

During one of my burnouts I took a "vacation" working (what started as part time) for a high-end flooring contractor. Although the owner and I had different backgrounds and beliefs we had mutual respect for each other (and we had great conversations). But what the public calls (and in public we called) an "estimate" we called internally an "interview"; and we wanted to take the temperature of the "pain in the ass" factor: Does the prospect truly understand the work? Does the prospect have irrelevant concerns? (I'm doing a poor job here, although I'm pretty sure successful contractors will understand what I'm talking about.) Our bids could vary as much as 300% (upwards) from our baseline model / estimate for the job... before we said "no" outright or came up with good excuse for them to fire us before receiving our bid.

There were some rather "zen" aspects of the process (my father had a zen question: how do you feel? I have a zen question: what do you measure?), such as an insistence that all special instructions had to fit, legibly handwritten, in about 1/3 of an 8x11 piece of paper. (We did $10000 floors on a one page contract, not including non-negotiable required boilerplate; why can't we do that in IT? Can we? Yes, yes I say we can.)

But distilling this down: some contractors would rather deal with the masssages and fish tank cleaning (at 3x the $$$) than do floors... whereas for us flooring was a religious calling or something. You'll find this both in doctors and in contractors; and you'll also find people out there who expect to pay that 300% markup to have the contractor walk their dog.

> Some lawyers bristle at clients setting strategic direction. They believe there’s a “correct way” to do things, they know it, and they’ll fight you if you disagree. In that case, get different lawyers. Ultimately I was able to find good counsel who were willing to work with me taking an active role.

Brrrrrr. AI an be enormously helpful when it comes to trying to understand - I have no doubt the author got exactly what they needed here. But if you're making blanket rules about ditching expert opinion because you can wield a model then I think you're letting your own engineer's syndrome drive things, and you're letting it be validated by survivorship bias.

Amazing blog post.

I'm new to entrepreneurship and just signed my first few corporate legal agreements. I was also deeply aware that anything agreed to was basically a gentleman's agreement--it wouldn't be worth either party going to litigation over, and even less so if the other party was internationally based.

So I've been following the "no-assholes" policy as well.

I don't think these lawyers were trying to give their "best representation". They have seen enough cases to know exactly what the best representation would look like and that this wasn't it. But lawyers are like business consultants. Poor work costs them nothing. In fact, it earns them more since they are retained for longer. This is a world where the lawyer needs to actually have an incentive to solve your problem as quickly as possible, and that is extremely rare. Having skin in the game could be one way.

Overall, this seems like a good take. However, I've never really seen this:

"When you tell lawyers “what do you think we should do,” they’re going to give you the “best representation” they can—because that’s what they’re incentivized to do. This means ticking every box, being as thorough as humanly possible, and taking everything the other side throws at them as seriously as possible."

My experience with smaller matters seems to be that they don't give it much attention because it's not worth their time. I think the author's take only applies above the small claims level.

> Don’t take the AI’s word for it—confirm everything.

This is all you have to do to counter kneejerk AI naysayers

You can also do this when talking to professionals its just that those professionals are charging you hourly, have low emotional intelligence and dismissing your ability to comprehend anything, have an ego to defend the discipline they had to use to get there, and confirming anything with them requires a separate meeting weeks later

Case law hallucinations and even law hallucinations are very dangerous. Any made-up citation can easily unravel your entire argument, and is a great example of how AI safety needs to be experienced to be taken seriously. The advice to use AI as a guide rather than a lawyer is crucial to follow when a million dollars is on the table.

> What lawyers typically won’t do is come up with creative ways for you to accumulate leverage against the other side to get them to back down.

Unfortunately, it seems you chose the wrong litigator. This, in a nutshell, is the job.

I would not invite the legal risks involved in giving a third party access to every business contract I have. Writing contracts in a way that allows for this and mitigates all or most risks is likely quite expensive.

Do you use cloud, or self host your email/documents/backups?

Cloud is just someone else's server.

We don't self host email, yet.

I've always viewed lawyers as (first) professional negotiators and (second) experts on law. I'm surprised that the author had to take the lead on the negotiation part.

> This forced me to develop practices of radical acceptance and get comfortable with circumstances I couldn’t change.

When you are in litigation you are at war, embrace the suck.

Thank you, that was an interesting read and gave me a perspective on something I knew nothing about

Use "AI" to fix problems caused by a broken legal system.

Why would you fix the legal system instead...

This is excellent! I hope big companies read this and think twice before trying to: a) take advantage of less-litigious players; b) create abusive contracts boobytrapped to go to court or force a settlement for control/IP/free-service later.

I hope it spurs a larger "moral reckoning" movement of legal strategy among "big players" - the moral depravity or trying to abuse other innovators through deceptive legal gaming is an illness US corps should cure themselves of.

My advice to developers/engineers who start their own corps is: always read every contract, think through the implications, consider worst cases, and only sign ones you're comfortable with. If you don't like anything, push back and negotiate. How does the other side they come off in that process? Make note of who they show you they are and incorporate that knowledge into your ultimate decisions.

I guess if you're VC backed the calculation is different: let the advisors and LPs absorb the risk and handle it for you. But if not: you need to get involved deeply. AI is a superpower that hopefully stops the abuses that have been so rampant. You got this!

> 1: Upload Everything to AI Projects. Use the projects feature in Claude or ChatGPT to upload all relevant documents—contracts, motions, emails, anything relevant to your case. You might need to be selective if you hit context window limitations with thousands of pages, but include as much source material as possible.

> For what it’s worth I didn’t necessarily find one platform (Claude or ChatGPT) or even specific models to be materially better than others at this work. ..

> 3: Leverage AI for Contract Analysis. AI excels at reviewing lengthy contracts. When you have a 400-page agreement where page 6 references “customary exceptions” that are finally listed on page 421, AI can instantly find and connect these references without you having to jump around through table of contents.

> Always have the AI excerpt the actual contract language with page numbers, then verify by searching the document yourself. Don’t take the AI’s word for it—confirm everything.

Check out Tritium (https://tritium.legal) to save this upload step. Open the folder (or right-click your folder on Windows) with your documents and chat with your model of choice.

I am not an attorney, but have been a litigation legal admin for over two decades in a major American megacity. I feel that this position may actually lend me towards a more objective analysis than a litigation attorney or the article's author, because I am a longtime assistive witness to the process of law without necessarily being its direct proponent/creator.

There were things I found problematic about this article. One of the primary aspects I found incomplete was that it doesn't go on to specify HOW he supposedly used AI to avoid the necessity for a litigation attorney. To me that was a vital piece of information necessary for the author to prove their point, and its omission means the essay is significantly flawed.

Much like a surgeon, a litigation attorney knows 'surgical' techniques - they know the specific dynamics of law that are at play. They further know from local experience with judges (and their colleagues' experience with same) and the "plaintiffs' bar" (i.e. people who are looking to make cases) which techniques are best for which set of circumstances, much like a surgeon can evaluate which surgical techniques are best suited for the job they see in front of them -- they have the power of accurately observing and evaluating what is in front of them in full 3D high definition, whereas AI is going to be subject to how the facts are reported to it (and what facts may be either purposefully or accidentally omitted by the reporter).

None of those techniques are gone into by the author; he merely indicates that he used AI, without going into what it advised him to do. The act of omitting that piece of information means - at least IMO - that the editorial itself cannot by definition make its point.

Much like a surgeon, a litigation attorney knows 'surgical' techniques - they know the specific dynamics of law that are at play. They further know from local experience with judges (and their colleagues' experience with same) and the "plaintiffs' bar" (i.e. people who are looking to make cases) which techniques are best for which set of circumstances, much like a surgeon can evaluate which surgical techniques are best suited for the job they see in front of them -- they have the power of accurately observing and evaluating what is in front of them in full 3D high definition, whereas AI is going to be subject to how the facts are reported to it (and what facts may be either purposefully or accidentally omitted by the reporter).

None of those techniques are gone into by the author; he merely indicates that he used AI, without going into what it advised him to do.

I will agree that - much like it has done for me with medical knowledge - AI has the power to "prep" you very well for appointments with your attorney, assuming that it is not giving you a higher-level hallucination or leading you into a knowledge blind spot, which, as amateurs in the profession, laymen may not know enough to recognize (I don't omit myself - I would at most consider myself a 'talented amateur' at law).

But entirely omitted from all this evaluation: attorneys nowadays are very conscious of a client's desire to be budget-conscious; they know they charge an arm and a leg and they will try not to, and will try to help. They're not always just out for the almighty dollar, despite the caricature. They will often know what you are looking to spend and they will work to accommodate such price range - because they want to foster client loyalty to them or to their firm, and garner a favorable impression and word-of-mout. Just as one example, as a very experienced legal admin, I have sometimes done things free (not illegally so) that might have, in old days, been done for cost by an associate. (I am not speaking of the practice of law. But attorneys in olden days might've had associates charge for administrative things that can be done freely, and with greater ease now with the presence of the Internet.)

Also, one reason why lawyers are more like surgeons than they are "general contractors" is that lawyers specialize. There are multiple fields of law expertise, much as there are multiple fields of surgery, and litigation attorneys are a particular surgical field.

In short, while I agree with some aspects of the essay - I think that there's value in allowing AI briefing to get you up to speed to be a more educated client, which itself can then save you time with an attorney, which may then translate to money saved - I think there are multiple statements within the article that are simply flawed, wrong, or don't reflect the current reality of law, and how lawyers interact with clients nowadays.

None of the above reflects any attorney-client confidential information. I am not a lawyer, I am not your lawyer, and I do not speak for (nor am I empowered to speak for) my employer.

As engineers we are (rightly) very scared of AI taking our job.

If I were a lawyer I would be even more scared.

There is an infinite amount of programming to be done. There is not an infinite amount of lawyering to be done.

Both statements are false, but even if they were true, if AI can do your job, and costs 1% of you, and works 100x faster, there's no reason to pay you.

I'm of the augmentation not automation camp. With AI you can very suddenly find you've 100x'd yourself up shit's creek legally.

In my humble experience programming frequently leads to lawyering ..

As one grows, so too the other.

Eh, I think the total volume of litigation will increase. AI will let laypeople be stupid faster and lawyers be smart faster.

> The Delaware legal system is fundamentally broken for defendants.

The entire US legal system is fundamentally and utterly broken.

If you want to make a few thousand dollars, I hate to share this secret thing you can do, but the reality of my experience is that the only thing stopping more people from doing this is, you know, some semblance of morality. Go find any local, smaller nonprofit organization. Volunteer with them for a day or two. Pay $80-$150 to sue them in small claims court for $5000 because <<you can literally make up any reason, you don't need evidence, it doesn't need to have happened, "mental hardship", I'm actually wondering if you hadn't have needed any interaction at all with the organization>>. Have an LLM generate 2-3 emails a week outlining anything at all related to grievance; each one you send to the organization is likely to result in billable legal hours. When the court date gets near, you can file for a motion to extend. Keep sending emails. After 4-6 months of doing this, send them a settlement offer for half of what you originally sued for.

I've seen this essentially destroy one nonprofit; the board was inexperienced in dealing with it, the person doing it had clearly done it before, by the end they'd spent ~80% of their bank account on legal fees, paid out a few thousand in a settlement to the plaintiff, and half the board resigned in burnout.

If you've never came into contact with this kind of weapon before, you might have it in your head "we'll just argue the case, we're clearly in the right" ha. ha. No. You'll never get the opportunity, and the people who do this know it.

If you're now thinking "well, if you're such a small organization why are you paying lawyers at all? We have AI. We'll just file responses on our own" I wish it were the case. But sadly: at least in my state, you can sue organizations in small claims court without representation, but filings made to the court in defense of the organization must be made by a licensed attorney. Asymmetry is built into the system.

The only thing that can protect nonprofit organizations from this, beyond having a massive bank account, is getting a lawyer to donate work pro-bono and/or sit on your board of directors. This is a common thing for nonprofits, for this exact reason, and assuming you're legit and well-known its not too hard to find legal experts who will do this for you.

If you're not a nonprofit, I have to imagine you don't have this angle open to you, and you're just SOL.

So "In dubio pro reo" isn't valid in the US?

>in my state, you can sue organizations in small claims court without representation, but filings made to the court in defense of the organization must be made by a licensed attorney

Same in my US state, which I'm actually using to my advantage — my state's small claims jurisdiction extends up to $25,000 so the defendant (a company) would probably get an attorney anyways =P

Once more people realize that LLMs can already throw together a reasonable case, I think small claims courts are going to be [even more] overwhelmed. On my last visit, I was explaining to many of the attorneys how accessible this all is becoming (none of them read SCOTUS Chief's end of 2023 report "On AI")...

“I used imperfect LLMs to ‘win’ (not lose) an imperfect lawsuit”

I highly encourage people to follow this advice. My fellow lawyers could use more people like him relying on AI instead of a lawyer. It makes it sooooo much easier for opposing counsel to win cases that would otherwise have been a slogfest against competent counsel.

Really, it fundamentally boils down to this: the CEO didn't bother tell his legal counsel he wanted to minimize legal spend. He just told them to do their thing. So they did, and because they weren't given constraints they did their thing well. But it wasn't what the CEO actually wanted them to do. The problem was that he didn't tell them what he wanted to do, and assumed that lawyers were telepaths and knew what he wanted.

So he did a dumber thing and decided to turn to an LLM, instead of doing the thing he should have done in the first place: tell his original lawyers what he actually wanted. He ended up getting lucky and not getting burned by it due to facts he chose not to disclose, but he is the rare exception.

Also, there are some huge falsehoods in his post, like #3. AIs are absolute shite at reviewing lengthy contracts. They're great at summarizing things where the correctness of the summary doesn't matter, but they're horrible at summarizing things where being correct is important. Also, his example of how the AI is used isn't AI. It's literally just a keyword search, which has been a thing for 3 or 4 decades now, and has been a basic function of doc review software for the last 2 decades.

#4. No, just no. It would cost more money to have the lawyer review an AI-generated legal document than to create one from scratch. Lawyers don't actually create most legal documents from scratch; they use templates from contracts and pleadings that have already gone through the legal trial by fire. So you're actually increasing your legal spend quite dramatically if you use AI instead.

Hallucinations. New models are not getting better at eliminating hallucinations; they're actually getting worse. Many of the recent AI-related court fails were from lawyers using the LLM tools provided by legal service providers like LexisNexis, and those LLMs were trained solely on legal databases. Even a single hallucinated citation in a legal filing allows the judge to void the entire filing and sanction the lawyers and client; in many situations the court this can result in a procedural loss for the client that they would have otherwise won on the merits if it had proceeded to trial.

TLDR: use AI if you want to make things easier for the other side of the lawsuit. Don't be like Trump. Experts exist for a reason. You wouldn't ask your lawyer to program your backend, so why would you turn to an AI for legal advice?