ChatGPT Is 80% Right About the Law — and That 20% Will Cost You

Collin McKee

Welcome back to the Endeavors AI Podcast — a show where we cut through the noise of AI and talk about how it actually works in the real world of business. I'm your host, Collin McKee, and today I'm sitting down with someone who lives at one of the more fascinating crossroads of the legal world. Ryan Alexeev is the managing partner of North County Legal in San Diego, California, and she does something most attorneys don't: she practices both estate planning and immigration law, including the cross-border tax planning that sits right in between them. She's been doing this for 17 years, she holds a legal master's degree in taxation, and she's got a front-row seat to two areas of law being reshaped in real time — one by the current administration, the other by AI. Ryan, welcome to the show.

Ryan Alexeev

Thank you. It's a pleasure to be here.

Collin McKee

You've got a genuinely interesting story. When I was preparing for this, the first thing that jumped out was your practice mix — estate planning and immigration, and the cross-border tax planning between them. That's a combination you don't just stumble into. Take us back — how did you end up at that crossroads?

Ryan Alexeev

When I first started my own practice back in 2009, I decided to do estate planning and family law because I could see the intersection of the two. I found that most of the people coming to me for family-law advice were foreign nationals, and their US-citizen spouses were telling them, "Because you stayed home and took care of the kids and didn't work, all the money is mine — and I'm going to have you deported." So I did a lot of educating people on community property, since California is a community-property state. Without a prenup, it's ultimately community property — so not all the money is just theirs. And on the immigration front, I'd let them know that if it's not a fraudulent marriage, you don't have to worry about being removed. I really enjoyed educating people on their rights on the immigration side. I didn't enjoy the family-law side as much — it takes a special type of attorney, and I'm not that type for that. So from that point forward I decided to do estate planning and immigration.

Collin McKee

Great story — and what I love is it wasn't really planned. Your clients told you where the need was and you followed it. So an obvious follow-up: most estate-planning attorneys never touch immigration, and most immigration attorneys would never touch estate planning. Why don't more firms see that overlap?

Ryan Alexeev

They probably do see the overlap — it overlaps into pretty much all areas of law. When I chose these two practice areas, people would ask, "If you had to choose one, which would you choose?" And I'd say, "There are over a hundred areas of law; I chose these two, so I've already narrowed it down." I chose them because I really enjoyed them. Honestly, for the first several years I didn't see exactly how they connected — I just felt they did. About seven years in, I started to see there's a real need for estate planning for non-US-citizens, and it's more complicated than planning for US citizens. At bigger firms they usually have an estate-planning department and an immigration department, and they don't really overlap. Only a couple of people in the country focus on this, and not quite to the extent I do. So I went back and earned a legal master's in taxation from USD — one of the best LL.M. tax programs in the nation, and it happened to be in my backyard. The dean understood I was a returning lawyer coming for a purpose, so I was able to tailor my education to focus on this cross-border scenario — the estate and gift tax side as well as pre-immigration tax planning. So now, depending on a client's needs — if they're in the US with assets overseas, or they aren't US citizens, or they're immigrants coming to get green cards — we figure out how it factors into their estate plan, and how it affects them on the tax side. The US has the biggest, widest-reaching tax system in the world, so we make sure they're not paying tax on things they wouldn't have owed if they weren't a green-card holder. Sometimes they take care of that first, then we do the green-card process.

Collin McKee

Lots to unpack. We're recording this during the second Trump administration, and immigration policy has been — to put it diplomatically — dynamic. From your seat, practicing immigration for 17 years across multiple administrations, what's actually different this time?

Ryan Alexeev

Immigration has always been a headline, regardless of party. Under the first Trump administration we saw the largest changes — something like a thousand-plus changes in immigration law in a short window. A client would sign a fee agreement on Monday, and I'd have to call them Tuesday and Thursday to say the scope had changed. When he came back into office, I figured we'd get the same whiplash. This time it's been different — the changes have been slower, but more forceful, and what we've seen is that they haven't necessarily been lawful. As a lawyer who follows the law, having to fight an administration that isn't following it has been extremely challenging. To give an example: just last Friday there was a huge change — USCIS is no longer going to process adjustment of status from within the United States unless there's an extraordinary circumstance. The problem is that's not founded in law or case precedent. There are going to be lawsuits. We're already seeing requests for evidence asking, "Why do you feel you should be allowed to adjust status within the United States?" — even though most of our processes do allow it. Think about student visas: how many people find the love of their life away at college? Now they're saying if you came to study and planned to go home, you can get married but can't finish the process here — you have to leave. It delays an already multi-year process, it doesn't promote family unity, and it'll create bigger backlogs and more divorce. Lawyers are already gearing up to litigate it.

Collin McKee

So the phones are ringing off the hook. After news like that, there are more questions than answers. If you had to pick two or three main FAQs your intake is gathering right now, what are people most curious about?

Ryan Alexeev

On the immigration front, since Friday people have been reaching out asking, "How does this affect my case?" — and we proactively reached out to clients too. When the news broke, I immediately posted a blog on my website, because I knew people would be researching it and I didn't want a million calls — I wanted people informed, and then if they have further questions, set up a consultation. Another big change this year: for specialty occupations, there's a new $100,000 H-1B fee. It doesn't apply to everybody — it typically applies to people getting their first H-1B from outside the US — but even those getting their first H-1B inside the US could trigger it by traveling, and we don't want them triggering that by accident. I also handle a lot of extraordinary-ability visas and national-interest waivers, and people call confused — "I know someone less qualified who got approved; why am I getting denied?" Right now it's hit or miss: weak cases get approved, strong cases get denied, with no rhyme or reason.

Collin McKee

I was going to ask about the "gold card" program — you touched on it. Any other detail for those who don't know it as well as you?

Ryan Alexeev

The gold card is basically a path to a green card via a roughly million-dollar contribution — the administration's view being that if you can pay it, you must be extraordinary in business. (I don't agree, but it's not about me.) I'd expected they'd build it off EB-5, the investor program — that makes natural sense. Instead we started seeing denials on EB-1 (extraordinary ability) and national-interest waivers. Then the details came out: they're effectively using the EB-1 and national-interest-waiver categories for the gold card. There are caps on those categories, and my suspicion is they're trying to preserve as many of those green cards as possible for people willing to pay the extra million — so USCIS was likely told internally to use discretion to deny where they can.

Collin McKee

Interesting times. Let's switch gears to the meat of it — AI. In our first conversation you said something that stuck with me: a lot of your clients are using tools like ChatGPT, which they should, but they're putting too much credence on what the tool can do — throwing documents in and getting back something that, in your words, is "horribly wrong." Tell me about an instance where that happened, and how wrong was it?

Ryan Alexeev

ChatGPT scares me from a legal perspective. It's good to get ideas flowing, to help with a letter or a template — revise it in your own words. But when people use it to ask legal questions, it's maybe 80% right, and that 20% is going to land you in hot water. A client contacted me not long ago having run their estate-planning wishes through ChatGPT — "This is what I'd like to do; how can I achieve this?" — and brought me pages and pages, including "and this is how your lawyer can achieve it." I read through it and had to tell them: you legally cannot do this. It's not enforceable, it's extremely burdensome, and it's ripe for litigation. So I had to explain why the ChatGPT answer was wrong even though it confidently said "your lawyer just has to do it this way." We talked through what they truly wanted as the end goal and came up with a plan that actually worked under the law. I'm grateful they listened. But it also affects pricing — when clients send pages and pages to review, I love working on flat fees so people know what to expect, but that kind of work starts to require an hourly component.

Collin McKee

You also said what scares you more is the clients who don't even try to use it. AI can be good for a first-pass scan, but relying on it like it's legal counsel is where it goes horribly wrong.

Ryan Alexeev

Right. Asking it "I bought a house, should it be in a trust?" — hopefully it says yes. Anything beyond that, I'd be concerned. It's like when we have a medical issue and turn to Dr. Google first — fine to check, but you should still reach out to the doctor. Same thing in law.

Collin McKee

You mentioned plans to add probate, partly because you see the downfalls of people relying too heavily on the LLMs.

Ryan Alexeev

Yes. More people are drafting things themselves, or going to a CPA or financial advisor who offers fill-in-the-blank AI estate-plan services. Unless you're working with an estate-planning attorney, it shouldn't be a one-size-fits-all service — it's very specific and should be evaluated by a lawyer who does this. Because people aren't taking that advice, I think a lot of it will turn into litigation. We saw it with services like LegalZoom — people save a ton of money, things aren't done properly, everything ends up in probate, and now it costs tens of thousands of dollars. You may have paid a couple hundred dollars or nothing up front, but it can cost your estate tens of thousands, if not more.

Collin McKee

You also compared AI to having a seasoned paralegal — so you're not anti-AI. Where inside the practice is AI actually earning its keep for you?

Ryan Alexeev

There are AI services I think are great — but you have to be careful. You've probably seen the news about lawyers using ChatGPT to prepare briefs and it inventing false law. Definitely fact-check. If you pay for a program specifically geared to your practice area, that's different — the ones I use are AI-generated but lawyer-backed, with lawyers doing research on the back end, so the sources they cite are legitimate. I still check the sources, but I can run a question through my lawyer-backed AI, get citations, and do research so much faster than I ever could before — faster than handing it to a paralegal. It's more cost-effective for clients, and I can run different "what if" scenarios in a fraction of the time. There's still a time and place for a paralegal that AI can't replace, but where we can become more efficient and save time, it benefits our clients and our business — we can serve and help more people.

Collin McKee

At the top of the year you made a decision to deliberately cut ties with a legal-insurance referral source that was feeding you a good chunk of business, because you didn't like how they operated. That took guts — and a chunk out of revenue. What's been the biggest obstacle in replacing it?

Ryan Alexeev

Pretty much replacing that revenue. I'm excellent at what I do; I'm not as great at marketing. (I find a lot of lawyers are excellent at marketing and not as good at the law — it's a balance.) So I've been looking into ways to let people know I exist. My crossover practice is very unique, but I also do regular estate planning, trust administration, and business immigration — so it's a matter of helping people find me. We've been more proactive about asking for Google reviews. I'm lucky that most people we ask follow through; occasionally someone who was never a client leaves an angry review because we wouldn't hand over client information — which I can't ethically do; I'll always protect my clients. After 17 years our processes are streamlined so everyone has a good, tailored experience.

Collin McKee

If you had a magic wand and got five hours back from the work you do well but that eats your time, where would you put it — content, following up with clients for referrals, somewhere else?

Ryan Alexeev

Definitely creating more content, because it reaches a wider audience — and doing more webinars or in-person educational meetings. A lot of people don't know what they don't know; they have questions and are afraid to call a lawyer. When a client calls and says "I bought a new house, I need to update my trust," the real point is making sure the house is actually titled in the name of the trust so they avoid probate. Those are questions I get over and over, so I post them as blogs and bring small groups together to cover what they should keep in the back of their mind. So: education and content creation.

Collin McKee

As we wrap up — a slightly clichéd but worthwhile question. Where do you see law firms that ignore AI and keep going status quo, three years from now?

Ryan Alexeev

Struggling. AI isn't coming — it's here, it's part of every day. Firms that don't get on board will see business slow down, partly because more people will try to do things themselves and end up in probate. Even doing your own legal business documents is a bad idea, because you don't know how things can go wrong — AI can give you projections, but you think "that'll never happen to me," whereas a lawyer says "we've seen people in your scenario, and here's how it plays out." Law is very much old, dusty libraries — a lot of lawyers don't want to move forward with technology, and they'll struggle. Some may retire earlier than planned or try to sell, but often they don't even have the processes in place to sell. So it's important to get on this bandwagon and try to be at the forefront — or at least on the ship.

Collin McKee

And do it with guardrails — you don't want to wind up in probate court, or worse, like the attorneys who made headlines in New York. Ryan, I really appreciate it — this was excellent. For listeners who want to find you, where's a good spot?

Ryan Alexeev

The easiest way is our website, northcountylegal.com — it has our phone number, a way to get on my calendar, everything. Or call the office.

Collin McKee

Awesome. For everyone listening, if you found value in this, share it with one of your attorneys or another member of your firm who needs to hear it. We'll see you on the next show. Thanks again, Ryan.

Ryan Alexeev

Thank you.