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Ep 58: How a lawyer built an AI company with Cecilia Ziniti, founder GC AI
101 Plays2 months ago
How should General Counsel and legal teams be leveraging generative AI? How do you get started on your AI journey and what mistakes should you avoid? Where is the AI revolution heading?
Join Cecilia Ziniti, Founder and CEO of GC AI, as she discusses how and why she made the leap from working as a corporate lawyer to creating a generative AI product specifically designed for in-house counsel. Find out how her years leading legal for AI-powered tech companies like Replit, Anki, and Cruise (and serving as lead counsel on Amazon’s Alexa) prepared her to create a company offering a groundbreaking product that serves the various needs of lawyers with precision and care.
Listen as Cecilia discusses the similarities between lawyers and large language models, how to begin experimenting with generative AI with the goal of making both your professional and personal life smoother, why you can’t let others tell you you’re “just” a lawyer, and why legal professionals should always use emojis.
Read detailed summary: https://www.spotdraft.com/podcast/episode-58
Topics:
Introduction: 0:00
Leading legal at Replit: 2:52
Why lawyers should use emojis: 5:40
Starting a business after gaining extensive experience working with AI: 13:00
Considering how GCs should leverage AI: 22:18
Hiring legal teams in the age of AI: 39:03
Teaching a class on AI at Stanford University: 47:35
Book Recommendations: 51:52
What you wish you’d known as a young lawyer: 55:11
Connect with us:
Cecilia Ziniti - https://www.linkedin.com/in/ceciliaziniti/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.
Visit https://www.spotdraft.com to learn more.
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Transcript
AI Feedback and Emotional Impact
00:00:00
Speaker
we got a piece of feedback where the person, we have thumb up and thumb down in product, the person thumbed up it, and said something like, this answer made me feel good. And we get that back. And one of our engineers is like, like, he was like really moved. He was like, wow, like, this is really lovely. Because we sort of personify the AI a little bit. And he looks at me and this engineer, he's like, well, I guess I don't know why this surprises me, because lawyers are people too.
00:00:29
Speaker
like yes what Don't let aboutt but tell you you're just a lawyer. Particularly if you're in your house, you are not just a lawyer. And you're only just a lawyer if you think you're just a lawyer.
Leveraging Generative AI in Legal Teams
00:00:46
Speaker
How should GCs and legal teams be leveraging generative AI? Where do you get started? What mistakes should you avoid? Where is the AI revolution leading? Okay, the last one's kind of a big question, but Today, we are joined on the abstract by my friend, Cecilia Zanidi, founder and CEO of GCAI. GCAI is a generative AI interface designed specifically for in-house counsel. It's a product that Cecilia always wanted. She has deep experience building and leading legal functions in tech, including most recently as GC and head of business development at Replit.
00:01:30
Speaker
She has also led legal teams or been the GC at companies like BloomTech, Cruise, Anki, and Amazon where she worked on Alexa, another cool product. I don't know how much we're going to talk about that today, but that could probably be a whole other podcast in and of itself. She started her career at Morrison Forrester and at Yahoo. Thank you so much for joining me today for this episode of The Abstract.
00:01:57
Speaker
Thanks, Tyler. are're Really excited to be here. You talk about GCAI as being a product you always wanted. Can we just start by having you tell us a little bit about what you're building? Of course, yeah.
Introduction to GCAI and its Vision
00:02:08
Speaker
ah So GCAI is essentially an AI platform for in-house teams. And when I say something I always wanted, there's this concept in software of like of having empathy for the user. And for me, that's extreme because I am the user. like In the past, like it it was shocking to me that legal software, you know by and large, has a reputation, that it's not particularly usable. And as a software enthusiast, you know I love Slack. i'm ah you know I use Grammarly. I use hundreds of different pieces of software a day. I thought, why can't we have software that's a joy for doing legal work?
00:02:44
Speaker
and the So that's what ah that's that's what we're building and AI was really the big tech shift that that to me makes that possible. Your last role at Replit before you left to launch this as cool it was a mix of sort of legal and business.
AI in Legal: From Engineers to Lawyers
00:03:00
Speaker
I'm just generally interested in this like founder journey. How do you feel like your years of leading legal teams, business teams to prepared you for this moment in time and prepared you to launch your own company?
00:03:13
Speaker
Yeah, so Replet is a development platform for software engineers. So it's the integrated development environment or IDE where they spend most of their time. Think of it as like Microsoft Word, but for engineers. huh And what we were building there was really about, okay, being that hub and using AI to help the core job of, in their case, creating software.
00:03:36
Speaker
So the realization that I had and what led me to to found GCAI in part was with AI, lawyers can have the same thing where you know we have this very brainy job, our stock and trade is words. So I hear that and I think, okay, LLMs, large language models, that's the tech behind generative AI. And what are we as lawyers? We are large language models.
00:04:02
Speaker
Like, literally, I tell this story, I swear, and I'm not even joking. I like, we've all had this experience, right, where you had to review something for compliance. And by the way, you notice three typos while you do it. I supported the CMO at one of my jobs. And he asked me very earnestly, when we were at lunch one time, he's like, Cecilia, how did you get so good at copy editing? I was like,
00:04:21
Speaker
Well, maybe it's still like 25 years of school and then the law firm and then whatever. And, you know, like we are like, I'm not particularly good at Excel, but my love language is words. And so that's what AI does. And so I had this realization of like, you take this tech that's made for language and a job which is being a lawyer that is really based on words, right? Case laws, pros, contracts or pros, advice to clients, typically pros, although of course you should use emojis. We can talk about that separately, but like those things are all words. And so when I think about that, and you know, I'm not the only one to have this realization. Obviously AI is super hot for legal at this point among venture capitalists. It's considered consensus to have legal AI, but,
00:05:09
Speaker
That was kind of the core realization. And so, and Replet, I think, definitely helped me. I also think, and we can talk about this, that software engineers and lawyers are actually we're more alike than we are different. And so, you know, lots of learnings I had from the BD side marketing to developers. Developers have an incredibly high BS meter.
00:05:29
Speaker
who else is a high BS meter lawyers, right? So like, that was definitely an experience that between, between I and co-founder Bardia Porvick-Gill, it's been an incredibly helpful experience to have that in our back pocket.
Emojis and Effective Legal Communication
00:05:40
Speaker
Okay. Why should lawyers use emojis? I got it. So fascinating research on this. Um, you know, we can drop it in the show notes if that would be helpful, but basically emojis improve recall tremendously. And one of the things that I've realized in house, and I think this is different from law firms is the law is like the table stakes. You gotta get that right. You gotta get the legal advice, right?
00:06:05
Speaker
But as in-house counsel, landing your message and getting the stakeholder base to do whatever it is you're asking, it's kind of like sales. You have to move people. like People don't naturally think, oh, I want to fill out a DPA. like It's just not a thing. You have to influence them. And so using every tool in the toolkit,
00:06:25
Speaker
such as emojis, to me is something that like it makes a measurable difference. And you know I'll tell you, actually, we had um a user of GCAI, and she's super into emojis, and she'll tell you this. When she's interacting with the sales team, supporting the commercial team, but she'll have like you know a legal update that she wants to provide, some new law regulation, what have you. And she'll ask GCAI to give her emojis and and create the message in a very readable way.
00:06:53
Speaker
And her stakeholder base noticed was like, you know Amy, your team is on fire lately with these incredibly clear updates. And that matches my experiments almost 100%. And so I have an emoji keyboard installed. It's part of our brand. But the reason for that is that it's part of being an effective in-house lawyer.
00:07:12
Speaker
is also coming to where the clients are, right? So for me, I worked for, you mentioned I worked for Lambda School, I worked for Replit. You know, they have a little bit of a Gen Z kind of bent to them. They're new tech companies. They are, you know, these private stage venture backed, et cetera. So, you know, I think I have a strong point of view on that. But I also think the rise of Notion, who I think you've had on the show, Hasani Caraway, Notion has a very, exactly.
00:07:36
Speaker
They have a very emoji forward point of view, right? Like to create a notion page, you add an emoji. And both the research and my practical experience back that up. So lawyer tip, use emoji, try it. um It's going to feel strange at first if you're not used to it, but particularly for internal communications, highly recommend.
00:07:53
Speaker
I love that. I mean, obviously getting to the right answer is only half the battle, and being able to communicate it effectively is just as important. Another podcast, s Dan Haley and I talk a bit about this on his episode. He's really great at this. Yeah, he made a video. Like Dan Haley and I, i'm I'm his friend too, and he mentioned that when they, long story short, his company at the time, Sprinkler, was having a hard time basically getting customers to accept their paper.
00:08:19
Speaker
Mm hmm. Because it would be like these big procurement companies, Proctor Gamble, whatever, that wouldn't accept their paper. And they made a video that was like, here's why you got to accept our paper. And you can find this on the web when we drop that in the show notes, too. But the video is like this little, you know, dancing whatever contract that's like, you should accept our paper because blah, blah, blah. But it makes the really compelling arguments. And he said to me, we we talked about this offline. I know if you mentioned on the podcast, essentially the video reduced the amount of requests like three acts or some like amazing stat. Wow. Created by, actually, because I have done a webinar with him a guy named Adam Stavsky and his company briefly, they do animations. They're really cool. I say that just because I think it's a really cool way to think about communication. Complex concepts or concepts that it might be tough to get non-legal stakeholders to pay attention to.
Personalizing Lawyer-Client Interactions
00:09:08
Speaker
Yeah. I mean, look, we're all, you know, lawyers use TikTok too, right? Like people ask me, like, you know, I went to to ah basically like a founder's thing and, you know, the question was like, should you be using TikTok for marketing? We don't at GCI yet. We do use LinkedIn tremendously. But the question was like, who's on TikTok? Everybody's on TikTok. The world's on TikTok. So like, you know, just because we're lawyers doesn't mean we're not people. And that's actually a funny story is that we had a basically a product feature and it was essentially the product feature was basically making the answers a little bit more personal to the user where it was like people would ask a question and it was like, okay, you know, good job. I think that I think the brief or whatever it is could be improved in this way. And we got a piece of feedback where the person, we hit we have thumb up and thumb down in product. The person thumbed up it and said something like, this answer made me feel good.
00:09:59
Speaker
And we get that back, and one of our engineers is like, he was really moved. He was like, wow, like this is really lovely. Because we we sort of personify the AI a little bit. and And he looks at me, and this engineer, he's like, well, I guess, I don't know why this surprises me, because lawyers are people too.
00:10:17
Speaker
yeah ah people like what are you talking me about It was just this beautiful thing where it was like, I think this AI when it has these like, kind of like agentic to use a technical term agentic capabilities where it does something for you, it interacts with you really on a human level. You know, if we can infuse that into the product, where it's like,
00:10:37
Speaker
It doesn't have to be formal. It can be your assistant and then, you know, your interface with the world, you know, you're filing in court or you're filing with the SEC, what have you. Of course, you're going to put your, you know, your lawyer voice on. But when you're doing the work, I think it can be just as effective to have that human element. Yeah, I mean that's actually, and maybe this is already part of GCAI's offering. You can even think of the role as the of the GC sometimes as telling members of their team, hey, this really needs to be three bullets, right? It can't be three paragraphs. or And you can imagine building that into a solution like what you've built. So that way, as GC, you might not have to be out there in the future sort of constantly providing that feedback to your team. It's being provided automatically based on the sort of guidelines or rules that that you've set up. That's really cool.
00:11:26
Speaker
I mean, that's one of the, like, honestly, that's our goal too, is like yeah really because you also over time with effectively communicating internally, you also increase that influence, right? That all of us want, like all of us want to be invited to the table. Okay. How do you get invited to the table is like you provide value and you're like, you know, like on the one hand, on the other hand, you know, okay, that's fine. Do the analysis.
00:11:49
Speaker
But then it's like you want you want the answer, right? And you want to be able to communicate in a way that instills trust and obviously it has to be right. So all of this assumes the legal advice is correct. It's just like, how are you how are you landing it? Are you thinking about the trade-offs that the team has? Sometimes you want to take a little bit more risks. Sometimes you don't.
00:12:06
Speaker
And you know I actually had, ah you know speaking of user feedbacks, we're super driven by user feedback, very much the um kind of Silicon Valley move fast kind of model, but in a good way of like Y Combinator, which is Paul Graham's company, which of course of course you know invested in Airbnb and other other famous ones. But yes his thing is make something people want. to And so been thinking about it that way. But one of the user feedbacks that we got And this almost made me cry. It said, with GCAI, my more junior team member is more strategic.
00:12:40
Speaker
because they get into areas they're maybe not as comfortable with. They hash out the advice first with AI and the and then give it. And so to me, that was something like, I'm like, I read that. I'm like, oh, this is why
From Lawyer to CEO: Leadership Lessons
00:12:54
Speaker
I'm doing this. And I just was like, I think, you know, I've had a bad day or something and I got that feedback and I swear to you, I was almost moved to tears. I want to ask you a few other questions about the founder journey and and being a founder of a business.
00:13:07
Speaker
You came out of companies or had experience at companies that were A.I. native, right? Or had A.I. products. Do you think that that was really necessary for having the confidence to start a business like this? Because you you're not like a large language model software engineer, data scientist, which is sort of the archetype for starting an A.I. company these days, I think. Yeah, that's the first that's the first sort of question. So.
00:13:36
Speaker
I actually think AI makes it easier to found a company. So you the core answer to your your question is yes, but AI now and Paul Graham back to program would tell you this that the knowledge and the depth in a domain, which I'm lucky enough to have in the domain of being an in-house counsel and particularly being an in-house counsel for tech companies. Yes. Building a product that points AI at that,
00:14:02
Speaker
the domain expertise ends up being more important than the technical expertise. And what what I think, ah you know yes, my AI experience, it's very fortuitous. like I don't take any of it for granted. I'm very, very lucky to have come to the Valley when I did and timing plays a huge role. That being said,
00:14:18
Speaker
I actually think with AI now, you can move so fast because the feedback that we get, the product feedback is again, it's about the words, right? So we get, you know, we get, we have a channel where when somebody provide provides feedback, it goes to a mirrored copy. Otherwise we don't see the chats because security, but it goes to a mirrored copy and we look at it and essentially like,
00:14:38
Speaker
know what a good legal answer looks like know the like underlying technology of how the tokens are being put together but you that knowledge so like so little bit easier you not being said like you know I do think you know, risk tolerance and then the ability to, you know, i I did okay financially. I worked hard for many years. I took steps down to be, to have the GC experience. I could have basically made more money as a number two or, you know, even a number X lawyer at bigger companies. And I still, you know, a part of me dies when I think about the value of my stock options at Amazon that I left over my stock at Amazon.
00:15:19
Speaker
But, you know, you got to play the long game. I mean, taking those back to careers, like careers are long. The Valley is small. Like for me, you know, the entrepreneur thing, it was there and I got lucky that the timing you know worked out. But I definitely think, like, don't let people tell you. And this was a message that I think um Greg from TechGC was talking about. Don't let people tell you you're just a lawyer.
00:15:44
Speaker
Particularly if you're in your house, you are not just a lawyer and you're only just a lawyer if you think you're just a lawyer. see It's a mindset thing. Exactly. I've got a question that I like to ask folks who have made that leap because I've been lucky to have a few of them on the podcast from being a GC or being a lawyer to founding a company or being a CEO.
00:16:05
Speaker
Do you still feel like you're a lawyer? Do you feel like you've had a big mindset shift? I mean, there's a difference in sort of accountability, I think, when you're the CEO than when you're another member of the executive team, which includes being a GC. Talk to us about how you've sort of navigated that mindset shift. Yeah. I'll take that in two parts. I would say the first part of like, do I still self-identify as a lawyer?
00:16:30
Speaker
ah Broadly, yes. like I think this is where you get into the you know the the really good career advice that comes from improv, which is like, yes and. right So yes, I'm a lawyer and I'm a CEO right versus no but. And that mindset shift of yes and total aside, complete career amplifier. Like just look at everything as yes and like, you know, sometimes it'll be like, you know, sometimes you want to say no, and it's wrong or whatever. But in general, that's been an amplifier for me. So yes, I identify alert and now I'm the CEO. But how are they different?
00:17:04
Speaker
In particular, you pointed to accountability. I think that's 100% correct. Like I would say, I mean, I had a pretty, I had a bunch of functions rolling up to me at Replit. You know, I had BD, I had support, you know, DevRel and obviously legal and trust and safety, but, and so it was a lot of responsibility.
00:17:23
Speaker
But CEO is just different. I was talking to my my spouse the other day and it's like every job in the company I kind of care about. like you know It used to be like as as legal. I could be like, oh, you know it's a finance thing. like i you know I partner with finance, but it's like not really my problem and it shouldn't be, right? like it wasn't That wasn't my function. But now, like we you know we had a stutter step where Long story short, Stripe was like misreporting our revenue and showing undiscounted revenue as our revenue. Great. But it was accidentally showing it, you know, higher than the number. That's not a big thing. But like, that's something where I'm like, I care about that.
00:18:01
Speaker
um yeah and like, oh, guess what? We're going to sign a contract. I care about that too. And it's just like this level of like figuring out that my role is really like making sure that all these other things happen. Legal absolutely has a component of that, but I would say it's amplified. And then you know that this whole thing of like, okay, you don't want to treat a company's family fine, but it is it's it's it's It's our baby, right? like and and And I feel that so deeply, particularly as a founder, CEO, that that that's different. And I had that as a lawyer, too. I was always very much like, one of the pieces of a advice I gave is it's always like, we not they, right? like We want to launch this product, as opposed to even you know some of the more junior attorneys I would mentor would come and be like, can you believe the engineering team wants to launch blah, blah, blah, blah, blah? They're crazy. like No, no, no, no. We are launching this product.
00:18:52
Speaker
you know, how are we going to make that happen? And that to me was a big thing with the rise of product counsel is thinking of yourself as like, okay, you're the lawyer for Google groups or whatever the product is. And like, it doesn't matter if it's a copyright question or privacy question or whatever it is, like, your job is to get, you know, get that product launched in a compliant way.
00:19:12
Speaker
It's they're not your clients, basically. yeah Exactly, exactly. and i mean Even to the point where it was like calling them stakeholders. so That was a big thing at Cruise, was you know calling your individual attorneys the client as opposed to your individual people that you work with the client as opposed to the company at large. Actually, I think that Delaware weighed in on that. so yeah It's a great point.
00:19:32
Speaker
What's the steepest learning curve associated with being a founder? Is it fundraising? is Yeah. Fundraising? No. Because actually, as GC of venture backed companies, I was relatively involved in in that. And certainly, you know the actual deal mechanics of like you know a lot of your listeners are probably deal people. So like that's not a learning curve. But for me, the learning curve, the biggest one, honestly, is just embarrassing. But it's actually the finance side.
00:19:57
Speaker
like i'm much more like a I would say I've always had strong partners in finance as a GC. So I've never really liked, like I don't know how to read a balance sheet, but like kind of barely. Like, you know, I, I, so that's been probably like a random thing, but it's also, we're really lucky at GCI where I tell the team, I'm like, this is a champagne problem that we have like more revenue that I know how to put on a spreadsheet. Like, you know, but it gets back to that mentality of like, okay, I'm not, I don't look at the world as a spreadsheet. Like that's just not my personality. and I'm sure there are attorneys who do, like right? So I have a friend who's a lifetime tax attorney and he is just brilliant with the spreadsheet, is brilliant with any finance person. For me, I came up as kind of product privacy counsel. It wasn't particularly math heavy. So even though I probably could have learned math or how to how to manipulate data better at some point, I didn't. So that that's where I would say I'm learning um the most. But other other areas, I mean, I think it's like,
00:20:54
Speaker
all the typical startup lore. It's fun. It's fun that it's it's happening. Like, you know, yes, hiring to your point hiring is exceptionally difficult. It's kind of like, look, if you're a lawyer, like, let me give this comment as your readers. If you can go to law school, succeed in law school, pass the bar,
00:21:11
Speaker
you know, presumably work at ah at some kind of firm, bill your hours, just like all those things are really hard. Tim Ferriss, who's a like, he's really big on, on Twitter, and he's the he writes the four hour workweek book. And his whole thing is like, do things that seem hard, because, like, basically, he says that paths to get rich that a lot of people take are actually the harder ones than entrepreneurial analysts. So he makes the case that if being a lawyer is actually much harder,
00:21:40
Speaker
than becoming a car dealer. I've read something somewhere that like i don't know like some measurable percentage of the millionaires in the United States actually own car dealerships. You're like, okay, like I can do that. It really is like a confidence, trust you can do it. and I think this is why you see the trend of very high performing GCs being COOs, right? so Belinda Johnson,
00:22:03
Speaker
of course, and then there's, of course, Kristin at Lyft and another lots and lots of folks. Oh, perfect. Yeah, so lots of your guests, you'll see that. If you can be an effective GC, a COO to me is not a big leap. I guess it's very similar. One of the things that I was hoping that we could do today is is talk a little bit about how GCs, how legal teams should be thinking about AI, leveraging AI, et cetera, besides subscribing to GCAI.
Starting with AI in Legal Practice
00:22:32
Speaker
How should in-house counsel, let's just start sort of broadly speaking, right like how should in-house counsel be thinking about leveraging AI around, what should they be asking outside counsel maybe, or should they be thinking about tooling internally, or is just like should they just start with chat GPT? What's the universe basically that we should be thinking about?
00:22:53
Speaker
I think part of it is a mindset thing where it's like, yes, AI is sort of everywhere and being able to separate the wheat from the chaff of like, okay, what can I actually like, how do I get started? So my recommendation, if you've literally never even used AI is to just cross that threshold of like, go to chat GPT and ask it for, you know, how to set up your kid's volleyball team or something like what? Like say something literally like use it for personal use cases because AIs have personality. So actually getting used to that and how they work and how it's different from a normal Google search, like I would consider that to be sort of threshold knowledge. And then, you know, and I'm not alone in this, by the way. So the ABA, the American Bar Association, which is the biggest professional organization in the world, I just learned 400,000. Really? Yeah. Great, wild, right? 400,000 people. I have a million people out of the ABA.
00:23:41
Speaker
Even I learned things on these podcasts. Exactly. I know, right? It's like I thought I knew all about legal treatment. I heard that factoid the other day. But anyways, came out with guidance on AI, long awaited. And essentially, one of the pieces of guidance that they gave was to learn AI, to literally learn about it. And so for me, I teach classes. So one of the things you can do is literally take a class with, I mean, I think it could be with me, but there are others.
00:24:07
Speaker
and just play with it. and the And the actual literal data coming out from, I think it was LinkedIn and McKinsey each have reports that say that people who experiment with AI end up finding those use cases and then end up being some of the having the higher productivity gains because they're sort of used to it.
00:24:26
Speaker
So for us, like our theory at GCAI is like, okay, take a class, use the product. And then there are legal use cases, of course, that all of us use, right? So like reviewing an NDA, we have ah like ah an official prompt within GCAI to review an NDA. And that's something that like an NDA, there's like, you know, 13 things, you know, the definition of confidential information, the exclusions, you know, does it have residuals, whatever, there's a very set number of things. And so that's actually a really easy u AI use case.
00:24:54
Speaker
Another is like your distillation. So I literally tell people like, go to GCI, upload your privacy policy, tell it or link your privacy policy, give me 14 FAQs about this privacy policy, and it will just go for it and do it right. So these sort of like distillation is kind of what I would consider to be sort of your like first stare in the staircase of like, you know, you're going to reach AI nirvana up here, right? Down here, you've got kind of like, okay, I just asked chat GPT, you know, for a recipe up here, you've got, you know, I'm doing everything we had a user do 258 chats in a week last week. So that was a record for us.
00:25:33
Speaker
But this person is asking everything in their department, like everything that they're doing. They were working on some compliance stuff, asking those questions. And you know that person, I would say, is top 0.01% in the adoption curve. But it's it's ah it's a vision to the future of like, OK, am I creating you know prompts that I'm reusing? Am I thinking about like, okay, I'm launching this product or I'm going to be doing this filing or you know we've got this initiative that m you know my health, my data act just came out in Washington. I got to roll it out. Let me come up with a compliance plan using AI. Let me come up with FAQs using AI. Let me tell the business team a slack using emojis, of course, using AI. So there's many things you can
AI as a Tool for Legal Efficiency
00:26:18
Speaker
do. I think some people
00:26:20
Speaker
The analogy that I use, and this might actually be helpful, is giving AI to a very trained lawyer, like an elite lawyer, like your listeners, where you're probably at a firm and now you're in-house, is like giving a marathon runner a bicycle, where they already run a sub two hour marathon, they're really fast. You're going to come up to them and you're going to be like, hey, you want to wear these strap shoes and you got to wear a helmet. And it's like, OK, by the way, you need a good bike and whatever. And by the way, there's possibly ethical issues with using this bike. There's going to be a good percentage of marathon runners that are going to be like, F you. I'm just running. The point is, the end goal is like, OK, if you give this elite athlete a bike,
00:27:06
Speaker
they can go more places, they can do different things, they can get off the bike when they got a climb, whatever. But like, the point is, they're still the rider, they're who's empowered. So AI in this scenario is the bike. And so I feel very strongly about that, that like my first advice is like, just try riding.
00:27:23
Speaker
And like yeah you can take a class. But in my class, that the part that gets the highest reviews is the interactive prompting, where I'm like, OK, go do this. you know Your company just got a letter from a senator. Go summarize it and write a thing to the exact team. And I do like time tests. And I literally i set a timer during the class. I'm like, three minutes. And I come back. I'm like, how do you feel? And people are like, that was really fast. But oh my god, I totally summarized my privacy policy in three minutes. like And like you cannot do that just without AI.
00:27:52
Speaker
So like seeing that light bulb moment, it to me, like getting to your light bulb moment quickly and getting your team to that, that's kind of, I would say that's a level one.
00:28:04
Speaker
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00:28:25
Speaker
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00:29:10
Speaker
But for ah you know the new, I don't know, Texas state privacy law, you are you are going to ask, hey, I don't really have time to read this thing. It's probably not as important. It's probably not as risky. Can you just do a quick scan of our privacy policy and see whether or not we generally align with the you know the requirements of this law? Or you might not use it to like draft the letter to the senator, but maybe you took some meeting notes and you need to summarize them for the exact team. And so rather than sitting there and reading through a page and a half of notes, you can distill it into seven bullets that you send around to folks. I think it's a great mindset of, Hey, why don't you try it here and there? It doesn't need to be a part of every workflow initially. That's a very fair assessment. And you know on the letter to the senator example, by the way, yeah you can go even further. right So maybe you got a letter with other companies and you're debating, do you respond as a coalition or individually? And you're like, give me three pros, three cons. right and And AI can do that very well. like And so this idea that like once you start to think of it as your intern or as your associate,
00:30:18
Speaker
you know, learning to delegate, learning to how they the intern learns, you know, that these take a little bit of time. But again, on the research front, researchers come out that people who are used to managing others tend to be better at AI.
00:30:34
Speaker
And so another thing that a lot of listeners talk about or a lot of people talk about in law, legal teams, they're not huge engineering teams, right? So like at Amazon, you could be a level seven, which was basically um you know principle the equivalent of principle of product management, of principle level. So above senior manager. You could be a senior, senior manager, basically just below directors and have no reports.
00:30:57
Speaker
versus a level seven at Amazon would have, who's an engineer, would have like 50 people, 60 people under them. So there's this craving for management experience. Okay. Think about what can you delegate to AI, right? And thinking about how to delegate things and how to phrase your requests correctly. Like that's actually, that's prompting.
00:31:16
Speaker
And people ask me, ooh, prompt engineering. like I think calling it prompt engineering is doing a disservice. It's really like management and delegation. And we have those skills as lawyers, and we should be building them if we don't. So exactly as you said, experiment. And then you know the next level for us, we have we find that once somebody saves a prompt as their own,
00:31:36
Speaker
In GCAI, essentially, we looked at retention data, and they they retain. like every Anybody who's ever saved their own prompt, has we've never had a cancellation of somebody who saved their own prompt. And so like something like that, where it's like once you reach that threshold level, you're past the onesie-twosie things, and you've actually gotten to that next level. So getting your team to that next level, and we work with companies. like We had a ah customer the other day where essentially our CTO, he's like he's an amazing He's amazing at prompting. And so he met with that with their commercial team. And they had reviewed. Their team in particular did a lot of a particular type of contract. It was events contracts, actually, random. But their company does a lot of events. So essentially, it's similar to what I said about NDAs. There was like 13 things in an NDA. OK, an events contract, there's like 14. Like what are the insurance provisions, what or whatever. And OK, now they've created that prompt. And so every time they review an events contract, they're going to be saving 10 minutes an hour. like pick Pick your amount of time.
00:32:34
Speaker
But like that's the once you start to see those saving those both time savings and quality improvement, i do you love it. And so like I feel very passionate that that's that's where the industry is going. It's just a matter of getting and getting it it into lawyers' hands. The intern analogy, I think, is a good one because it also highlights the need often to check the outputs or check the work product. It's like if you have an intern create the first draft of a deck that you're going to be sending to probably not the border investors, but maybe the border investors, right you're probably going to want to check the content of the deck.
00:33:11
Speaker
Um, how do you counsel folks who are getting started with Gen AI on what do they need to check? How do they need to check it? Do they need to check everything? How do you handle the sort of objection of like, well, if I have to check everything, why do I, why should I even use this in the future? Talk us through that output piece and the, you know, how do you actually use it like an intern piece?
00:33:36
Speaker
Yeah. So the core advice on this is like, so my, the full analogy that is how I give it is that AI is a smart, fast, occasionally over eager intern who has read the whole internet, right? So six pieces to that metaphor all are all irrelevant, but the, to your question, like, so hallucination, so we can talk about that, yeah but basically My thing is use a tool that reduces them. like So data is very hard to come by here ah for reasons I can explain. But essentially, chatGPT, the consumer version, um for a variety of reasons, one, trying to save tokens, two, copyright, actually, it tends to paraphrase things a lot. And so when you use it to review a contract,
00:34:23
Speaker
you will see hallucinations, particularly with the less powerful model. So if you use GPT 3.5, nobody does that anymore. But back when that 4.0 would still cost many, people would say, like, oh, you can't use it for for legal. It hallucinates you much. So that is true. The more powerful models are a little bit better. But what happens is, to save tokens, which is sort of the core unit ah of of analysis in AI, um OpenAI tends to abstract longer documents.
00:34:53
Speaker
Now, as you know, as a contracts person at a contracts company, you gotta have the exact text, right? So a customer shall assist is not a good paraphrasing of customer shall provide assistance upon the occurrence of A, B, C, and D, right? because that is not the same thing. right And so like that's why we make the big bucks. right That's why we're the wordsmiths. That's why lawyers are LLMs. right So when you see errors like that, it comes down to just some fundamental things. And so I actually got asked recently by somebody. They said, hey, we like your training. Can you give the training on chat GPT?
00:35:28
Speaker
And I ended up saying no, because I'm like, look, in order to get the good legal results, you need both a tool that has thought about this and the good prompting. And so the prompting that you said, like, at what point is it not worth it? Like, my thing, you can get okay results from chat GPT, but you have to do, I call it artisan prompting. Like, you really have to be very specific with your intern of like, hey, you're a legal intern and hey, you know,
00:35:55
Speaker
go out to the web and check your answers and hey, do this. yeah And it's just more than most people are willing to do, right? So back to my mixing, my analogies crazily now, back to my bike example, it's like giving somebody like a unicycle and you're like, okay, the unicycle, like you're going to like fall down and like, it's probably still faster than running, but it's like annoying. So I'm like, okay, let me give you like, like a track, like a fancy bike.
00:36:19
Speaker
That's what I would say GCAI is in this scenario. And there are others, like like I've heard good things about Ironclad's AI, Spotdraft, I know you guys are doing a ton of AI, and you have the advantage that the data is structured, right? So in that scenario, you're going to reduce hallucination just by virtue of the fact that Spotdraft already knows what the indemnity provision is. And so you're not going to get hallucinations from the AI accidentally looking at the confidentiality provision. So in that scenario, like I do make that recommendation of like using a dedicated tool.
00:36:47
Speaker
But then you know in terms of like like how do you deal with just other annoyances, I think this is something where you're going to lose that head start. You're going to lose that learning on AI if you wait for it to get good. So this is like the early adopter thing where it's like, you know basically, if you wait for it to get to non-hallucination, you're probably like you know a year or two away.
00:37:08
Speaker
And in that year, you could have been thinking of use cases, you could have been using it for all the cool stuff. And, you know, by the way, like, I mean, obviously, like I stand behind the product is why we do we generally do free trials, like get in there and use it side by side and and see how you like it and ask the questions. But I think the more it's one of these things also where once you get a sense for when hallucinations happen. So pro tip.
00:37:30
Speaker
Illusinations are more likely when you tell the AI something exists that does not exist because the AI is wanting to make you happy. So to the internal analogy. So if you're like, Hey, give me a case that says this, the AI is like, uh, Johnson versus, you know, set or 195 of third 67. And it just kind of, cause it thinks that you're like all knowing, right?
00:37:53
Speaker
Good test analogy. i'm a ten um I was a Federer fan. There you go. Exactly. yeah and I think it's okay, by the way, to say ah AI can't do everything and AI is not going to be right all the time. and It's a tool and we still think that it's valuable and we still think that you should start to embrace it and we still think that you should start to use it. and Yeah, like check the check the outputs check the results, right? Like it's it's okay to be sort of a bit of an evangelist and also recognize its limitations. That's exactly right. And that's why sometimes I i in terms of these starter tasks.
00:38:32
Speaker
Things where you already know the law. So those of you who are in your house, you know where you spike, right? So how many times have I given a privacy training? Hundreds, right? So I know exactly what what it's going to have. It's just like, it's like slightly different, right? Because you're going to do a privacy training for a customer care, you're going to do a privacy training for, you know, the ads team, whatever, like things where you know what you want to say, and you need help to say it.
00:38:56
Speaker
AI is just that's the golden use case for AI right now. And so what what what you said is exactly like that was a great way to put it. A last sort of question for you on, you know, AI and legal teams. I'm not only curious about how people who are already on legal teams should be embracing AI and using it and sort of getting ready ah for work looking a little different.
00:39:24
Speaker
I think you've also worn a GC hat before. You probably have an interesting perspective on if you're a GC, is your hiring going to look different in the future now that you have AI?
AI's Influence on Legal Hiring Trends
00:39:33
Speaker
Are the types of employees or backgrounds that you're looking for going to be slightly different? Maybe you can get by with more of a generalist who's empowered with AI as opposed to needing a variety of specialists. I don't know if that's right. I don't know if that's what you think, but I'm curious for how do you think this is going to change the makeup of in-house teams?
00:39:50
Speaker
Yeah, so i I think I think what you said is right. And I think it's not only a trend of of law. I think it's a trend overall where even the Navy again, I'm i'm like, I'm just like so passionate about the Navy on on a ship, on a submarine. It used to be they had a specific person to do every little thing. Right. But as systems become more advanced and more electronic, it's much more about like troubleshooting many systems versus have one one person do this particular thing. thing and what it points to is really like the rise of the generalist and you know other scholars have thought about this out of MIT, out of other places but in legal I do think I mean the term general counsel of course like what I and the way I see it is that you need a T shape or you know a pie shape right with two T's yeah but anyways like a T shape for me that was IP and privacy and so you know but
00:40:45
Speaker
when I became a GC, of course, I had to pick up corporate, of course, I had to pick up employment and other areas. But for employment law in particular, like, yes, it varies by state. But as an attorney, you know, a lot of these judgment calls, like you can start to use AI or use, you know, actually look at the law straight and bring it outside counsel like, okay, we've got a judgment to call, we've got a super gnarly issue in Idaho, or what have you. But your basic question of like,
00:41:12
Speaker
Okay, you know in Idaho, can you know if you have a termination in Idaho, do they get their paycheck on their last day? Or like California, or is it okay to pay them you know in 10 days or whenever their next normal paycheck would be? um So the answer is actually the latter. But anyways, the point is is like something, a question like that, if you've got access to the internet or you've got access to an AI, you can answer that yourself without going to counsel. So like this kind of thing,
00:41:37
Speaker
And then like having somebody where, and this is something every company I've worked for, so from Amazon to to Repl.it, and and I think Stripe has this value as well, has curiosity as a core value. yeah And for me, I was talking with somebody, so I was actually talking with maybe another another guest of yours about what makes a good product counsel. And his point of view was that the best product counsel are M and&A lawyers. And I was like, okay, that's peculiar.
00:42:04
Speaker
plain And he said, M and&A lawyers are curious AF. They can get up to speed in a new area very quickly because they're used to researching whatever issue of the thing. you know and he's like And he's like, they work super hard and they're super diligent, so they can put a lot of information quickly. So he's like, I've hired six M and&A lawyers to my company. All of them are the best product counsel you've ever met.
00:42:24
Speaker
I said, interesting. Cool. I thought that was fascinating for me. I think it's litigators. Like I'm biased. I think the best part of counsel are, are commonly former litigators. But anyways, that ability curious though, when I was a litigator, you know, you become an expert in that case. Like I became an expert on pharmaceutical proteins when I was on a patent case at Mofo.
00:42:44
Speaker
to the point where like it was like ASP 9, and I know the like how the proteins branched in that patent case. And so like that ability to absorb new law areas of law, I've seen it a lot in tech, but I think it's also an important hiring criteria overall. And those are the folks that are into AI and will use whatever it is they can to satiate that knowledge to follow that curiosity to get the job done.
00:43:07
Speaker
So, yeah, I mean, to me, I think like that's a hiring philosophy. I sort of have it anyway. um We had at Lambda School or or um now BloomTech, our head of compliance actually came into the company as it as the CEO's EA. But she showed an incredible affinity for compliance.
00:43:24
Speaker
there was no form she didn't like like. And so I literally pulled her over as initially as a compliance manager. And then now she I think she's senior manager of compliance and she runs basically a 50 state compliance program for the company. so And I've worked with a lot of compliance folks in my career and and she I would definitely put her among the best.
00:43:43
Speaker
I love this value of of curiosity. I think it's super important. I did an episode with Evan Furl who now has his own small investment fund that was largely focused on sort of the role of creativity and curiosity in in legal and and how important that could be.
00:44:00
Speaker
um And I will ask you for your book recommendations too in just a minute as we
Creativity and Diversity in Legal Insights
00:44:04
Speaker
start to wrap up. But um one that I think I've talked about before on the podcast, other folks have recommended is called Range by David Epstein. And it it is a great sort of book that I think is ah it's it's It's good for GCs to to read because they often feel like they're sort of, I think, caught between a lot of different worlds. and And they worry that they've stepped away from being a specialist because they probably had that opportunity to become a partner potentially at a law firm in which things were very secure and specialized. And ah this book talks, as as you point out, about all of the sort of
00:44:41
Speaker
social science and and psychology research that supports the idea that having a variety of different experiences or having two or three different areas of domain expertise is actually where the real creativity happens and actually where real insight occurs. um You can be a specialist and you can have insight, but sometimes the hardest problems can't be solved by those folks. Sometimes it has to be solved by someone who sees, you know,
00:45:10
Speaker
I don't know, the dark side of the moon and the light side of the moon, too. Yeah, for sure. I mean, I do want to in defense of specialists. So another another friend of mine. like So I 1000 percent agree. Sam Holman says the same thing because he's like, if you want to be top one person in the world in one field, you're Roger Federer. Yeah. You know, it is.
00:45:32
Speaker
Mathematically, very, very difficult. But if you can actually have two fields and kind of get yourself in that VIN diagram, yeah the matchups, you already increase your odds more than twice to be top 1%, right? So he makes that argument, and I would definitely agree with that. So for me, it's law and tech, right? So people that have a background in law, yeah there's a lot of lawyers and you know only nine members of the Supreme Court, at at least as I'm just writing.
00:45:55
Speaker
um you know but But I have a good story on that too. But separately, there's a lot of like general counsels. There's not many more general counsels than our Supreme Court members, right? So you are experts. If you can be an expert in your business and an expert lawyer together, like to me, that definitely drew me in-house. But yeah separately, a defense specialist. So I have a friend of mine. She ah has an SEC practice, and she spent 10 years at the SEC. So, you know, she literally like, she had subpoena power during that time. She, you know, securities law, she knows both the practical aspects of like, okay, you know, the actual, ah that you know, Securities and Exchange Act, and then the actual ability to advise companies. That's what she's doing now. And she is classic big law partner, $1,600 an hour. Her name is Rebecca Feike, Vincent Elkins. If you ever have a security matter, like give her a call because she is absolutely worth whatever it is she's billing at.
00:46:49
Speaker
but For me as a GC, I'm thinking, okay, I'm using AI and then if I actually have the issue and I need to negotiate with the ICC, okay, I'm calling Rebecca immediately. like that's kind of i see that I do see this hyper specialization at the firm and generalization.
00:47:07
Speaker
And by the way, more are going in-house. So in-house has grown tremendously, seven and a half times the rate of outside counsel in the last 25 years. So there's an awesome graph. um Again, we can put in the show notes, but there's an awesome graph on that um that I can share. But those of you thinking in-house, is this a good opportunity, et cetera, like it's growing a lot because companies are looking for people that can solve their problems, right? And so we were definitely seeing that that displacement.
00:47:35
Speaker
Last question before you before I got some fun ones and
Learning AI: Resources and Classes
00:47:40
Speaker
it should be easy. You know you you teach a class at Stanford. You mentioned the class that you teach on Maven. If folks want to learn more from you about how to do AI prompting and use AI, like where where can they find you?
00:47:55
Speaker
Yeah, so our our website is getgc.ai. um You can also Google my name. It's kind of unusual enough that you'll get me. But yes essentially, I would say getgc.ai. So when you send a demo request, you'll get an email back. If you mentioned that you heard about it on the pod, we can maybe we can work out a ah discount or something. But we can we can do something something for that. But I'd love to have you try it. like Again, my saying I push on it is like,
00:48:24
Speaker
get in there and experiment and try the product, like do a couple of things. You you know, you kind of owe it to yourself. And honestly, now we, you know, there's another um on the classes point in February, the California Bar is launching a specialist credit for CLE. So we've got substance abuse, elimination of bias. They're launching one for technology. um And we got that credit. So if you're looking for that CLE, you know, you can kind of use that as an excuse to play around with AI. So that would be my other recommendation. Cool.
00:48:54
Speaker
Some fun questions for you now. What's your favorite part? This is all been fun, Tyler. This is really, thank you for having me. I love it. I just, I could talk all day about this. I do. This is a real, this is a real conversation, which I love. For those, you know, well, nobody's keeping Dragon Home except for me. We've gone off script like 70 times so far. I love it. So good. What's your favorite part of your day to day or your routine?
00:49:24
Speaker
Definitely the user feedback. So I'm going to come come back to that. So yeah I mean, for me, you know, when I was in Amazon, it was the kind of customer obsession. And that's a value that I've brought throughout my career and and been able to to achieve. But for for me, like having making a product, it's kind of like the feeling is very similar to like when you're when you write a really good brief as a litigator and the court, you know, cites your stuff exactly or you write a brief and it's mentioned and you're like, this is amazing. It's very similar. you know For us, we launched a new feature called Easy Prompt where basically you can put in your prompt and we'll make it into like a nicely formatted kind of prompt engineering style prompt. And literally, I'm i'm not i'm not joking, a user was like, I want to marry this feature.
00:50:10
Speaker
I want to marry you too. So that that's definitely my favorite part of the job. um you know Lots of like lots of favorite things. you know The team, getting to talk with folks like you. like i mean i and There's lots of things I like that that's a single favorite. How about a professional pet peeve? I think this is kind of a funny question. Special pet peeve, let's see. I would say even though I appreciate the hustle, because now I'm i'm selling, but the unqualified LinkedIn reach outs are so funny and ridiculous. But like, I mean, sometimes I had one where
00:50:45
Speaker
It was like, they reached out to sell me something and then they continued with the Drip campaign that was like, did I miss you? Did I miss you? You know, did I get something wrong? Do you hate me? And it was like, it kind of like devolved into these like multiple levels of like passive aggression. And I was like, okay, like this, that's the pet peeve. But I think that's kind of funny. So I guess I'm like not that annoyed about it. But I would say that that's my professional pet peeve.
00:51:10
Speaker
And now you have an opportunity, ah you know, some days very soon or right now to teach some salespeople how to sell to lawyers a little better. Yeah. Yeah. Look, I mean, I definitely think like, you know, it's sales. It is definitely an art. um and And I've learned so much about it. I have a post cooking on social media about like random sales terms.
00:51:31
Speaker
I heard the term today in sales, there's a term called happy ears and it's for a sales person that hears things that are happy. And I was like, that's me. I haven't been yours. I think everybody should use AI. So when I, when I'm talking to somebody, you know, they're like, they mentioned something. I'm like, Oh yeah, let's use happy ears. Um,
00:51:52
Speaker
I've mentioned a book ah today that I think folks should pick up and read based on our our conversation. It doesn't have to be based on our conversation, though. If there's a book that you've read recently or that you think is really important to your professional journey that you'd like to recommend to our audience. Yeah, so many. So many. I think um so. There's one that I read almost 10 years ago, but it really had me thinking about about how a lot influence and the ability to influence make a big difference in your life. So it's called to sell is human. And it's a psychologist named Dan pink. And one of the points he makes is that every job, including education, by the way, he's like, teachers are sales, you have to sell the knowledge, you have to sell the desire to learn. And thinking about sales in that way, as opposed to like, okay, you're shady salesperson reaching out to me on LinkedIn, like,
00:52:46
Speaker
Thinking about it as as influence and getting things done, I would say that's been very influential to me. The other one is a scholar named Jeffrey Pfeiffer out of Stanford. And he wrote a book called The Rules of Power. And power is kind of, the other one I would say is Deb Liu, who also wrote a book called Take Back Your Power. Deb was a student of Jeffrey Pfeiffer. But essentially Jeffrey Pfeiffer's point is like achieving outsized levels of success is really at some point about knowing human dynamics.
00:53:16
Speaker
And, you know, he uses examples from, you know, from Trump, who, you know, yes, ah you know, obviously, like, you know, politics, disagreeing with his politics, which I do, but thinking about like, how did he use power dynamics and media moments and, you know, essentially,
00:53:31
Speaker
display, in some cases, very physically power. and And how can you do that? So, you know, that was something super interesting. It also is fascinating to me, particularly in a venture backed company context, because you've seen what a company's valuation is, you could argue it's a number pulled out of thin air. So like, you have to believe you have to display power and he gets into that.
00:53:51
Speaker
And he teaches a class at Stanford, um Professor Pfeiffer does, that is oversubscribed every semester, that is is basically on that, and talks about essentially the interpersonal dynamics for any job, no matter the substance, um are really important to learn. So I would say that those two books, To Sell Is Human and then Power, The Rules of Power by Jeffrey Pfeiffer, and then secondarily, I think also for women, and particularly women of color,
00:54:14
Speaker
the book Take Back Your Power by Deb Liu. I admire her a ton. She has a sub stack. She's the CEO of Ancestry dot.com, came up with a product manager at Meta. And that's a great, I really, really enjoyed that one too. Great recommendations. ah And I always, I love that there's so little overlap between the guests, an indication that there's so many great books out there to read. I mean, this gets to a curiosity point, like I still genuinely believe, you know, Obama read a book a week during his presidency. And, you know, yeah, which is like, it's like shocking, right? And so like something like that, where I want my leaders to be always be learning, um just in general, and and something that I try to live myself now a little bit more on Twitter or podcasts, but um other podcasts recommendation for folks in house, there's a podcast called acquired.
00:55:01
Speaker
And it's deep dives on companies and just learning the dynamics and that their their tagline is every company has a story. And I think that's true. Last question for you, my traditional question for closing question for guests. And that's if you could look back on your days of being a young lawyer, just getting started at a law school, something that you know now that you wish that you'd known back then.
00:55:30
Speaker
I would say, I would put it probably in a message of comfort that as long as you put one foot in front of the other, you have that curiosity and drive, it will work out. Like I literally remember I was debating between an offer at one firm and another and I was like almost in tears of like, well, do I want to, do I want a New York based firm or California based firm? And like, and, and I look at that now.
00:55:58
Speaker
And it's almost ridiculous where it's like, okay, if I had gone to the other firm, I would be fine. like And I did one and I did the other. like It literally is like that diligence and the kind of lawyer I became and what I did. like There would be slight mariances, but there's no... like any one decision, this is maybe the Amazon one-way door thing. What's the worst case scenario? like Even for me at this company, like I have every confidence it's gonna succeed and we're gonna be a unicorn. But even if we're not, I'm a really dang good lawyer. So like yeah can I go back to being a GC lawyer? Yes, I can do that tomorrow. So I would say it's that it's that confidence that any one decision is not a one-way door.
00:56:39
Speaker
I love that way to put it. A similar sentiment to what we've heard from a variety of other folks who've become founders, started businesses. ah But I love that ah that analogy or or that phrase of, you know, one door is not one door. Actually, there may be other doors after it. That's fantastic. back Exactly. Chichilia, thank you so much for joining this episode of The Abstract. This has been a lot of fun for me.
00:57:06
Speaker
Oh, same. I literally like, I feel like it's like, ah like we were just talking at a party or something. I love it. Thank you so much, Tyler. This is so fun. And to all of our listeners, thanks so much for tuning into this episode of The Abstract and we hope to see you next time.