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CZ and Friends
The Kanye Clause, Taylor Swift IP, and AI: Mary Ambacher of EverQuote and Lauren Anderson of Wayfair
00:49:46
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- [00:00]
A
How do we get five to ten years from now when you still need the Laurens and I who've had this business judgment and have gotten it from practicing for so long if you don't have the junior attorneys starting and getting that from the beginning?
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B
Today I've got two guests who are living AI in the moment. Inside companies in high side legal teams. Mary Amaker is the deputy General counsel and assistant Corporate secretary at Everquote, a publicly traded insurance marketplace in Cambridge, Massachusetts. Mary spent nearly eight years at Wayfair leading teams across corporate privacy and commercial work before making the jump to a smaller company with a bigger scope in a new industry. Lauren Anderson is senior counsel at Wayfair where she works on commercial transactions. Has been deep in the question of how AI fits in the day to day work of a practicing lawyer at a fast moving global company. Together, the team evaluated more than six legal AI tools, navigated hiring uncertainty, and have been wrestling with things that a lot of legal leaders won't say out loud yet.
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A
You,
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B
Mary and Lauren, welcome.
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A
Thank you for having us.
- [01:07]
C
Thank you so much.
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B
All right, Mary, you just made a big move. We were just chatting about how you haven't had a new job, had to start a new job in eight years, and you literally said something like, I forgot what it's like not to know everything. So you walk into a public company and you're overseeing the whole legal function. Tell us about day one, the kind of first day of school vibes.
- [01:29]
A
Yeah, it was interesting in that it was much quieter. Like day one itself, it was just quiet and I was kind of walking around as if I had no idea where anything was, which made sense. But it was just such Wayfair. You get a lot of bigger company in terms of just people around. So there was always buzz and it was just very quiet. And I just remembered being like, okay, now what do I do? So it was, it was a bit of an adjustment, but I'll say by day three, it was kind of to the chaos, I think I was saying, and drinking from the waterfall that I was probably anticipating. People were so excited that I was here. They hadn't really had a kind of SEC corporate kind of in house person really in a long time. A lot of folks that just have done general governance but got a great team here on the finance side that was pitching in. So, you know, they gave me probably 48 hours and then the question started. But, but it's, it's been really nice. I think the, the biggest kind of scary part was just, you know, I Was so used to Wayfair, and I could navigate it kind of like the back of my hand and, you know, starting that all over, I'm. It's exciting, but I'm also like, okay, I need to get there so I can, you know, that that comes with your value add, right? Like, knowing where everything is and knowing everybody to talk to.
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B
Are you thinking about what success will look like?
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A
Yeah. It's a very fascinating question in this topic of AI too, because I think I came in with this. Okay, I'm going to go in. I'm going to build a team, probably similar to maybe what I had before on a smaller scale just in terms of the business. And then I walked in and we have all these great AI tools we can use, and we hired a great senior contract specialist and paralegal. And now I'm like, okay, with the two of us and some AI tools, we can probably get a lot more done than, you know, maybe five years ago without them. You would need a lot of bodies. So I'm trying to give myself some time to figure out, really, where are the gaps, you know, that we're going to need to fill. Do you need a specialist in something, you know, or an insurance marketplace? Do we, you know, do we need some specialty knowledge in the insurance space? And we have an attorney that's been helping with that, but he's also moving into a lot of other stuff, too, just because, you know, small, nimble teams and we got these AI tools now. So it's an open question, but I'm trying to figure out, really, what should the shape of that be?
- [04:02]
B
So people talk about kind of building from first principles when you come in, and it sounds like, you know, AI is. Is a part of that, of what you're doing. You know, for anyone else listening, that's like going to be starting a new GC gig and kind of doing that analysis. Like, what are the. Are there, like, specific markers or are there, like, do you work backwards? Or, you know, because, like, I had somebody ask me, you know, hey, with AI, do I need to clean sheet my department? And this was someone at a company that had been around 25 years, and this person had a team of 60. And I, you know, I didn't. I think it's almost in some ways tougher if you're, you know, kind of have a big team that's been doing things a certain way for a long time versus coming in to something fresh. So you've got the perspective of coming into something fresh. How are you going to do It.
- [04:56]
A
Yeah, it's actually very timely. I was at a breakfast this morning with a bunch of other Boston GCs, trying to, you know, build up some of my network there. And it was on this topic of AI, both internally and law firm spend and how are you going to manage that and all those different things. And this exact question kind of came up with some of the folks in the room that have had bigger teams. And we're literally saying, you know, you actually probably have the benefit if you're a new startup and going to be the GC there of using AI and building and figuring out what to do versus some of these companies that have been around for a long time and have built these, I mean, great legal teams. And they were talking about, you know, you have great lawyers, but the world is changing. And I think the nice thing that we were talking about and I hope happens a lot more is reskilling or upskilling some of these attorneys. You know, like, there's folks in IP or commercial attorneys that Lauren and I have talked about a lot. Could be great, just even in the business field. You know, we've seen hundreds of thousands of contracts, and sometimes, you know, the value add to the business from a commercial attorney is not the legal stuff. It's telling them some business points they've seen a million times. So I think that's part of the conversation of, you know, I would suspect a lot of teams are not going to continue to grow. But, you know, are there ways you can, you know, repurpose some of these great minds into other things you need? But also for me, then kind of the nice thing is I do have a bit of a benefit of, you know, we've got a small team and a growing company, and we can kind of take a more measured figure out, you know, where are the gaps that we're going to need help on the legal side.
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B
All right, let's. Let's go to Lauren. So, Lauren, you're at Wayfair. Wayfair has been around a long time. My favorite kind of. We have like a bureau table from Wayfair. I think of you all every time. Every time I go there, but every time I walk by it. But been at Wayfair through a lot of change. Obviously, AI came. You started Wayfair in 24. How are some of the things that. So Mary's departure, you get to. You take on a larger scope, more streamlined team. How are you thinking about AI now and then, how are you thinking about yourself stepping into this new role?
- [07:13]
C
Yeah, I mean, one I Miss Mary a lot. I mean she was pretty much like the brains of our department, I would say so definitely majorly increased scope. I think Wayfair's kind of already done a really good job about implementing AI tools and really like pushing us to use various tools. So we kind of had that foundation set. But given we're such a smaller team now, like we pretty much have three attorneys plus one that comes in and out that review all of the contracts that come through the company as well as like various legal issues. So we really have to utilize AI as much as possible, but also smartly. So we use GCAI often. That's kind of, we've implemented some sort of process where you should really rely on that for some sort of first pass. We really want to get rid of the mundane and the day to day repetitive tasks and really kind of spend time as Mary said. You know, I think AI is going to allow us to make more business decisions and be more involved in the business rather than doing like the day to day nitty gritty work. So I think, you know, my team has really done a really good job about utilizing tools as much as possible and we're going to, you know, continue to ramp that up. How can we be smarter about, you know, utilizing playbooks or creating tasks or you know, an idea of like a Wayfair brain where we have all of this knowledge throughout the, the legal team that we can kind of make these more mundane tasks a little more automated, a little faster. Because I think at the end of the day when you work for a company like Wayfair, it's all about like how quickly can you get the best product out. So that's kind of the goal that we've kind of set for our team.
- [09:11]
A
And I promise I didn't tell Lauren to pluck me.
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B
So there you go. No, I love it when that happens naturally. So one of the things you said, you mentioned just a super high volume. So give us an idea. And then you talked about products. So I have to imagine you're literally selling millions of products. So give us a flavor of just the sheer volume of commercial contracts that either go through your team or through the company.
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C
I would say, I mean it depends on the. The season end of year is crazy. We kind of did a time of death at the end of the year of like how post mortem, I guess of how many agreements we reviewed, I believe it was close to 300. But I mean that was just, you know, in a two and a half month window and you know, between the team. But I would say any of us have on average like 50 agreements to go through on, you know, bi weekly basis. Some require more attention than others. You know, we have certain policies in place where we can kind of spend less attention on an agreement versus, you know, a high level spend something along those lines, but it's definitely a high volume. And then you have those miscellaneous requests that don't necessarily require a contract review. Does require some sort of legal research or, you know, business judgment. Can we move forward with this, you know, AI feature on our website? You know, it's not necessarily a tool. It's. We're making our own AI chatbot. Like, what does that look like in terms of implementation? What privacy concerns do we have?
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B
Those type of things and then can
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A
we do it tomorrow? Yes, yes, exactly.
- [11:03]
B
Literally looking. You all supported a Super bowl ad. I must have been in a tight, a tight time frame. You, you know, in your time at Wayfair, you had a Supreme Court case. You, you have, you know, you must have at any one time. I mean, even just on the, on the disputes docket, like just keeping the business going. It's, it's a, it's a. And then of course, public company in both cases. All right, so, so on, on the pulling a thread, the thread a little bit, Lauren, on, you know, what good looks like, right? So you said getting the product out the door. It's funny, I, I was talking with a legal team of a, of a restaurant chain and they said, you know, it. We were talking, had a similar conversation and they said that at their company, you know, that whenever it was easy to get wrapped around the axle about kind of specific processes. But as a North Star, they're like, all right, sell more sandwiches, open more stores. That's kind of the thing. And it's like, how do you balance that with, okay, we're going to have legal AI reviewing, you know, indemnity provisions or, you know, whatever it is. Do you create like specific okrs or like, like, like show us, like tell us how you do it. Because I think a lot of people are craving that. So I guess I can go. Either of you can take that one. But just the more, almost the more tactical, the better of like, literally you've got this task, 50 agreements at any one time. I'm remembering when I was in bd, we had three or four or something like that. Tell us about that.
- [12:38]
A
I was going to say Lauren and I worked on it a lot extensively over the last year when I was still a Wayfair, trying to come up with exactly that. How are we going to measure success using it? One, to show our gc, because he was very keen to obviously get the most out of it, but show that we were being productive with it. There's a good example of you can get an AI tool and you can have it go through every single sentence of a contract and help you and that's not saving you any time while you're going line by line with it. So we, we came up with kind of A2 buckets and obviously Lauren, you can tell me if you guys keep doing that, but you know, it's kind of like what are the things that can just get reviewed and even by a non lawyer. Lauren and I set up a good process with our procurement team there to actually do some of the contracts themselves and then have Lauren and team focus on the high level ones and then truly to your point, just metrics. Right. So how many contracts are we getting through in a month or we have a thing that could tell you like time to open, to close. Is that getting shorter and just kind of using like the data? Obviously Lauren, if you have anything to add.
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C
Yeah, yeah, we still have it in place.
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B
Great.
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C
Yeah, so we have things like, you know, excluded contracts or you know, of course we're spending a lot more time on an agreement that's over a certain threshold monetarily, you know. And I think to Mary's point, it's not about using these AI tools to read line by line. I think what's important and kind of the question that we have about like training junior lawyers, like how to, how do you get to that point of not using it to read line by line and really like focusing on, okay, I know this SaaS vendor is accessing some sort of PII or you know, it's going to be ingrained in the Wayfair systems. Like there's more risks associated. So like knowing that how can I look at this contract differently? So I think really just like level setting that training for the rest of our team is super important and we've kind of tried to train them up on that and make sure that, you know, we're really dedicating time to the contracts that really like our benefit fitting Wayfair and also ensuring that we're not like, you know, having things fall by the wayside for these super important vendors, making sure we're still doing diligence where it's needed, but also, you know, not spending time. If it's a renewal form, you know, it's not going to take as long. I think that's really where you can use AI very smartly. Where you can just say, here are these four things that I care about. Are they contained in this agreement? If not, just add them in.
- [15:25]
B
Excellent. When do you think, just putting on your prediction hat, when do you think AI will be good enough? Maybe it is already to just pull lawyers out completely.
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A
I think there's a world to Lauren's point of certain contracts that you already can. Right. If you think about it, junior attorneys, I was one once, so I'm allowed to say this, but they're not always that great. And you know, maybe they're sometimes getting it 65, 70% of the way. Right. And most AI tools were, you know, the big thing people like to say is, well, it's not right all the time. I found mistakes and I was like, right, I, I found mistakes myself over my own work that I did five years ago. And. But I, we were fine with accepting a B plus or an 85% on that because that's all you need for that thing. Like, we used to talk about that a lot. I still love saying it. When, you know, SEC work, you need A plus work that's attention to detail, that's public filings, some commercial contracts. You know, I'm like, give me your best C. I just need this out the door and we got to help the business move. And there's a lot of AI tools I think that are probably already in that B range. So they might actually be doing better than if I had, you know, a junior attorney review, an NDA that they've reviewed 100 of them. Or think about a first year associate that's gone through due diligence and you know, I used to do it and not going to lie by hour five, you're like, what am I looking at anymore? And the AI is probably picking it up better now. That's kind of scary because that's a lot of work that might go away. But the thing that I keep grappling with and I don't have a great answer and been asking everyone to chat about is how do we get five to ten years from now when you still need the Laurens and I, who've had this business judgment and have gotten it from practicing for so long, if you don't have the junior attorneys starting and getting that from the beginning. So it's, it's just going to be a very interesting, I think next 12 to 24 months.
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B
Lauren does that. How does that resonate?
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C
Yeah, no, I agree. I think it's also important. So you have the AI tool, but it's also about the user. So like, the user needs to know exactly what to do to get that B. I think they need to prompt the AI. The AI has the capabilities, but how do you get there? And I definitely think that some, you know, it might eliminate some staffing, I think, I don't think, you know, like attorneys in general, but you might have smaller teams, you might have less people looking at contracts. You might be relying on the AI more. But I do think that it. It gets to a point where the AI can't do everything. Like, you need that experience, you need the business judgment. You know, I feel like, at least in my learnings, I've learned a lot. I know the law, but you don't always think about every terrible outcome that comes out of a commercial contract until something bad happens. So with that experience, it's like I can build that into my review. Okay, the AI picked up, you know, how to make this limitation of liability tighter. But like, maybe we need to. I think a lot. Mary and I spent a lot of time on like SLAs pushing the business to make sure that like, yes, we have the legal protections in place, but what about like, from a business standpoint point, if this software is something we really need, it goes down like, okay, well what are we going to do? So like those type of things that maybe, I don't know, like a, like the AI won't actually pick up on or flag to the business is also important. So you got to have the Marys of the world to keep going.
- [19:07]
B
Good examples of that. I had a guest on the POD a few weeks ago and he talked about
- [19:14]
C
how
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B
essentially in that SLA context, exactly. They had done basically a. I can't remember if it was like a. A specific indemnity to the SLA or something. Basically where it was like a. Almost like a guarantee. They did a separate exhibit that was a guarantee that was like, hey, if we like maybe even shirt. I. It's funny because I guess I feel like a bad lawyer because I don't remember exactly what the mechanic was, but tldr, it was an appendix where if the vendor did not meet that particular sla, it was like. It was like a. Not just a breach, but it was. Various other things were going to kick in. It was essentially a form of liquidated damages. But it was like a little bit more sophisticated than that. No, you know, I know exactly who it was. It was a huge global retailer and mentioned doing that. And then Lo and behold, that happened. So basically it was a many million dollar IT implementation and then the vendor came back and was like, we can't do it. We want XYZ more dollars. And it turned out that what my friend had put in ended up making a huge difference. And the business was like, wow, how'd you know to do that kind of thing? And it was sort of like a good moment for legal. Although of course the best moment is like they would have performed the contract. But with that example, anything stand out at you of just like, hey, you know, I. Let's say you got to the B plus answer or let's say you found a particular agreement strategic enough to warrant the, the effort, anything stick out? It's just like, wow, like I made Wayfair better or I made ever quote better from, from this particular work and you know, obviously confidentiality, et cetera. But if there's anything you could talk about that'd be helpful. Any big wins.
- [21:05]
A
Yeah. I'm thinking, to be honest, it's going to sound simple, but I think one of the biggest things just as a legal team that we changed the mindset of the business over years was no non renewals at all. Almost anything. Even if it's something we probably are going to keep using. And that just came from a long time of trial and error and especially in this new world of new tools every five minutes, you know, someone tells me they want this for three years and then in six months they're like, just kidding. It's, we found something way better. And that's hard to be honest, an education point to the business. Because every SaaS tool, they're gonna hate me saying this but obviously, you know, they, they don't want that because.
- [21:48]
B
I know, I know.
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A
And because like oh, business continuity and
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B
whatever, it's like, no, you're not gonna freak out.
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A
No, it's for, it's for them to be able to budget out for the next three years that they have that, that stream of income. And I get it on their point, but also for us is, and it's a huge thing, especially on the, to be honest, when we were looking at all those six legal AI tools, it was, you know, we didn't want to be locked into anyone for an extreme period of time because all that's changing every, every five days. You know, Gemini was ahead then, then Claude, then ChatGPT. And so you need to be nimble. And I think part of that we tried to instill across in other things too. Not just the non renewal, but flexibility Is probably, I think the biggest thing Lauren and I, I would say is a big win that we've given them is making sure they were a lot of clauses getting the ultimate flexibility. Whether that was credits for, you know, non used space or just, you know, if we were using consultants, like if we ended up not needing just a lot of flexibility, ramping up and down across different things, I think is a huge thing we did. And also just like help push the. That became the business culture is like, you know, contracts here need a lot of flexibility. Yeah.
- [23:01]
C
I think also to like kind of bouncing off of that. I feel like we've also kind of pushed for termination for convenience which like I feel like is a rarity to actually get. But kind of getting comfortable with some sort of like breakup fee. Like, okay, if we are entering into a long form agreement, we try and keep contracts I would say generally to a year with three years kind of being the max. But what does that look like? Maybe we should get comfortable. Is this something we're actually going to use in three years? Because I don't think anybody can really make that determination. We do have like processes in place to have those type of deals be approved. But I do think kind of getting them comfortable with like these, it's a possibility that this isn't going to work out. Like what are we willing to do or pay to get out of this?
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B
I mean that resonates so hard even now as a CEO where you know, everybody's all excited to use, you know, the new marketing consultant, the new, you know, tool, the new even, you know, we're literally planning for President's Club. We've been selling like crazy and I'm like, you know, I still remember being burned from COVID I'm like, I don't know if I want to give, you know, the Ritz, whatever XYZ money right now. But. But it's the thing where I
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A
from
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B
the business side having to think about that, it's kind of like there's this book that's like that I really like called Burn the Boats about you know, energy you spend on plan B is not energy you spend on plan A. And so you know, kind of move forward and having a great legal team that thinks about that so I don't have to and kind of saves me from myself. We literally. This is embarrassing. What you said about the breakup fee is like literally we had a marketing advisor that we were going to hire and plans changed and I went and looked at it. We didn't have anything like that. So I did the like kind of commercial thing and I sent an email and I said, hey, look, you know, wires crossed. We can't do this, you know, five month, very heavyweight thing. And in that case, business person to business person, they let me out. But it would have been nice if they'd have thought in advance because there's just a lot of consternation around it. And then the breakup fee is a little more than I would have liked, the kind of like in the moment fee. But the guy knew that's how it was. So was this something where have your business people kind of noticed and thanked you? Are there any kind of great sort of. I mean the super bowl ad is a big one. Other big initiatives where it's just like legal gets those shout outs.
- [25:44]
A
Oh yeah, we have Rob on our commercial team, on Lauren's team. Give him a little shout out. But we had a big marketing deal, kind of same thing like naming rights and stuff like that, that was tied to viewership. And it was his idea to make sure we were really comfortable on what those numbers were. And he was just doing some math himself. And yes, obviously the team was helping but you know, it, it was just, we've tried to instill in the lawyers that like, if you see something, say something in terms of that might not just like look right to me, just ask. And that's been a really nice, that was like a really, really nice thing that I'm learning here too is like that where the business is not, you know, they're not wary of the lawyers kind of chiming up and just saying stuff. There, there's no, you know, ego or ownership pride. And then, you know, when those things come to fruition, yeah, you get a nice kind of, you know, thanks for doing that because you know, we, we thought it might have gone one way and you were super excited about it. So obviously sometimes, you know, rose colored glasses on what you think is going to happen.
- [26:48]
B
Well, and I think what you said is a perfect counterbalance to that where it's not just, you know, okay, we're going to save you from yourself, which of course is hyper useful. But in this case with the, with the viewership metric, you know, people think like lawyers are not creative. I actually think being an in house lawyer, you have to be super creative. And you know, like, especially when you're doing deals in new areas, like we're working on a deal now with a supplier and you know, debating on do we do it by. Exactly as you said, do we do it by usage, do we do it by, you know, an API call, Do we do it by this? Do we do by that? And it's, you know, the lawyers are, their ideas are as good as mine, if not better on that. So how do you, I guess, like, how did you get to that level of confidence and how do you instill that in the team? So we have this junior lawyer problem, that's a topic in our script, but is it getting the reps? Is it seeing when it goes right, seeing when it goes wrong? What are we going to do to instill that in the next gen? Wanna go, Lauren?
- [27:55]
C
Yeah, I guess I can talk from my own experience. So I think where I got my confidence, I was at a startup before, um, I came to Wayfair and kind of similar to what Mary said about drinking from the, the waterfall, that's very much how I felt. I went from IP work to supply chain and logistics, which truthfully I knew nothing about, but I did majority contract work. I think you really just need to understand the business. That's like number one. And also just like be comfortable with, like you might make the wrong decision and like, that's okay, we can fix it. I don't think at the end of the day, like any of us as attorneys are really going to make a terribly wrong decision, I hope. But I think you just need to be confident about it. I think you need to really trust your judgment. I think, you know, you have the foundation as a junior attorney, but like it also utilize your resources. Do you have outside counsel that has kind of helped in these areas before? Consult them. Do you have, you know, CEO, CFOs, like everybody who's like higher within the company also has much experience, like always consult them and make sure that your gut is kind of there and like it's not off or, you know, maybe the company has a different risk tolerance or, you know, is risk averse. So I think you really need to understand those foundations and then just really trust your knowledge and trust your gut. And I think it's definitely reps. Like, I think that you just need to like keep going, but you'll get there. And I think that's kind of what we've seen in terms of, you know, junior attorneys struggling as to trust their gut. Like it's okay to, to not always make the 100% right decision. And to your point, you have to be creative. Like in house. It's a must. You can't be, you know, within these parameters. The business wants to get it done. It's our job to figure out how to get it done.
- [30:14]
A
I used to always say to the team there when they would get really nervous or it was like a big thing and, you know, it's a lot of people moving fast and you know, even Lauren and I couldn't be looking at every single thing they did because there was just so much work. But you want to make them feel comfortable, obviously to keep going and make decisions. And so I used to just always tell them we are just, you know, someone's got to make work for the living and they're going to need stuff to do. So I used to always turn around to my co worker Mike and just say, you know, I'm keeping, I'm keeping you in business. So it's, you know, every. Everyone comes full circle.
- [30:47]
B
A profound point which is like perfection is not the thing. Like that. It's interesting. I still remember, actually, Rest in peace, my torts professor, Levy, he kicked off the torts class with an example probably quite relevant to Wayfair. Which is the optimal. If you're, let's say you're going to ship, you know, porcelain plates across the Pacific, which I'm sure you do. But anyway, if you're going to do that, he's like, the optimal number of plates to break on that ship is not zero. He's like, because if you, if it is zero, then it's like you've spent, you know, you've individually packaged each one and you've gone really slow. And you know, the cost of replacing, you know, let's say 1% of the plates or whatever it is is worth it. And he used it to illustrate the point of like, how you approach risk. And I found it really like it was actually something that, like I said, literally 20, whatever years later, I still come back to it. But how do you gauge that in a new company? I guess that's an interesting question. So Mary, you go to insurance and insurance is literally like the calculation of this kind of risk. And do you. How do you either set the culture or figure out the culture of that kind of risk taking? So Wayfair, of course, came from the E Commerce days, sells to millions. It's consumer. What was different and how did you figure that out or gauge it?
- [32:08]
A
Yeah, it's a very good question. The first thing that I'm quickly learning, which is great, we're a lead gen marketplace in the insurance sector, which is now how I like to say. And everyone would say that to me and I'm like, okay, is that so we're just, we do insurance, but it's true. And it's like how we used to always say, you know, we would always say Wayfair is an E commerce company that happens to be selling furniture in the sense of like, you know, it's not a furniture company. Right. Like it's, it's a, it's an E commerce tech company. But we're putting all of that E commerce tech into furniture and decor and kind of the same thing here. Like it's, it's fascinating. I was like, oh my gosh, am I going to be talking about insurance every day? Like, I don't really know anything about insurance and I've been here three weeks and yes, it's obviously an underlying core component, but it's at first and foremost a tech marketplace that, you know, I'm still living and breathing a lot of the same just tech issues. So that's helped with kind of some of the comfort level, but it's a recalibration of, you know, risk. I truly think the culture of that comes a bit from your top down. You know, what is your leadership team comfortable with? And that truly is part of the game in that you have much more risk averse or risk tolerant folks and then our job is to learn, learn that and recalibrate for them. And I think I've been in a fortunate opportunity. I would say at Wayfair we've always been on a much more risk tolerant which was great because we get, you know, protect the company but also like we want to do innovative, fun things, move fast and do that in the, the safest way we can. I would say here's very pretty similar in a sense of we want to do a lot of fun things and move fast. I'm learning there's just, you know, there's another piece of insurance itself is regulated. So that's kind of been the biggest, I guess, eye opening thing just to make sure I'm taking that extra beat before I'm making maybe the exact same decision I would have made while I was at Wayfair.
- [34:12]
B
All right, we've teased Taylor Swift discussion, so let's talk about Taylor. So one of the things Taylor Swift has done is taken a pretty hard line on IP around AI. So tell us that background and then you know, how does that play out in commercial transactions or tech transactions that you all work on?
- [34:34]
A
Yeah, I'm a huge Swiftie. I went to that Risk tour too many times probably to tell people and my niece Evelyn is like the biggest fan. We did an entire Taylor Swift photo shoot. So I have a lot of Taylor Swift knowledge. But the coolest thing I think about her is she's kind of been a pioneer in the legal space and a lot of stuff, which has been great. And this is like just another kind of area where she's now making all these IP filings right for her likeness. So her image and her voice, she doesn't want AI to use them. And that's not been a traditional way to make an IP filing. But I kind of think the biggest thing about it is it's her that's doing it. Right. So, you know, if an artist not many of us have heard of have gone and done that, I don't even know how maybe where they would come out at the USPTO in the courts. But because she's doing it and kind of taking a stand, and her millions and millions of Swifties like us are like, yes, that's awesome. Like, you should protect that. She's kind of already winning in the court of public opinion, which I think might end up making a bigger deal on how this plays out. And then for me, taking that a step further, like, why I love that she's doing it because that's actually her helping all the other artists. Right. Because if they're going to do it for Taylor, me and Lauren used to call, we put the Kanye clause and everything in all of our contracts, and now maybe there'll be the Taylor Swift IP clause that they're all going to get the benefit of because she was the one that came out and did it.
- [36:04]
B
Yeah. I mean, she is probably, to your point, the only artist that could stand up to Apple. So when itunes had a thing where itunes was giving away basically, like three months free when you bought a phone or something like that. And their point of view is the artist should not get paid for those three months free, even if there were a lot of streams. And she wrote a letter that is like, literally to your point. Masterclass in Taylor Swift. Let me. Let me. Let her to Apple. It's so epic. It was. It was. Let's see. It was five years ago to this week, I guess, or five years ago in June. So she says, let's see. She says, no, 10 years ago, 2015. I write this to explain why I'm holding back my album 1989, from the New streaming service Apple Music. All due respect, Apple, it's not too late to change this policy. Three months is a long time to go to unpaid. It's unfair to ask anyone to work for nothing. I say this with love, reverence, and admiration for Everything else Apple has done, I hope that I can join you. And basically, you know, she got the trillion dollar company, you know, to move. So, yeah, I think it's outstanding. And another reason I'm a swiftie is this like savvy on ip. It's so good. All right, Lauren, explain to us what is the Kanye clause?
- [37:29]
C
So it's a morality clause. So termination for cause, I guess. Termination in the event, you know, our celebrity clients are involved in some sort of scandal, like alleged or proven, you know, anything that can kind of harm our reputation, we want to be able to get out of the agreement. Because, you know, I think especially with growing celebrity talent as well as even just like small influencers or medium sized influencers, you do have an inherent risk of, you know, you have these people representing your brand. You want to be able to get out if some sort of scandal happens. I feel like these days with the Internet, all scandals come to light. So, you know, and I think that there's a lot of like, public discourse when, when these things do come to light. So how do we protect ourselves? I think, you know, Wayfair didn't, to my knowledge, have any experience with this, but I think, you know, the, the Kanye clause did come about due to his actions. And I think that, you know, the, the industry reacted. You want to be able to get out of your agreement. I believe Adidas was not able to get out of their agreement or if they did, you know, I'm sure they paid a hefty sum of money to do so because, you know, that just didn't exist. But I think it's, it's kind of to the point of, you know, Mary talking about IP and you know, how Taylor's outcome is going to affect IP clauses like these things, real world examples are why terms and conditions are the way they are. So, you know, it's, it's, it's definitely interesting. And I'm currently negotiating a Kanye clause right now, trying to go that's a more middle ground.
- [39:23]
A
Lauren, Lauren's being a bit humble, but when we ramped our, you know, affiliate kind of marketing program, it was tens of thousands of probably you'd say these small medium influencers that she kind of put a process together to get the team up to speed on like, the things they should care about. And like, that was a huge one because to me it was more. It's not the big celebrity, right? Because that's kind of. Well, we want to make sure it's in there, but, you know, that's going to have A whole bunch of other issues for them. But, you know, with all of these, you know, the YouTubers and the TikTok influencers, that's becoming a huge, huge, huge marketing area for E commerce in particular. And they're lower contract amounts, but you multiply that by, you know, 20,000 and someone says something that, you know, maybe Wayfair doesn't want to be associated with for any reason. And that's kind of the other thing is like making sure these are in our judgment. You know, it's in our judgment that we don't like that, you know, opinion. Yeah, it's gonna, you know, that's gonna be talking about. We were going back to earlier, like that will be a huge thing that she's done to kind of get in those four, you know, hopefully nothing comes up, but to have them.
- [40:33]
B
Yeah, I mean, 20,000 influencer agreements.
- [40:36]
A
I come back, I might have exaggerated a little, but it's that lots of thousands.
- [40:40]
B
I mean, it's still like even just a thousand is like just the law of large numbers. You're gonna have somebody do something crazy. I mean, I just always like, I, you know, I was at Yahoo when I started my career and you get some crazy things. I remember funny talking about insurance. There was one of the first cases around basically the discoverability of Facebook. So there was a period. It's hard to believe now, but there's a period where whether your Facebook posts were discoverable was like a question. But the case was a woman who, you know, had a workers comp claim around, you know, being injured at work and said, you know, she couldn't work and all this. And then she ended up winning a tree throwing contest at the holidays, Christmas tree. And she was on the radio stations, you know, Facebook page as having won it. And so anyway, but the more thinking about it is like at scale of like these things of like it's sort of coming back to what you said of like protecting the company from themselves and then you know, even let alone regulated industry.
- [41:44]
A
Right.
- [41:44]
B
So you're in insurance. I remember one of the buy now, pay later companies had a matter with the, the. What's the big consumer regulator? Oh my gosh. That regulates financial. Gosh. Cfpb.
- [41:58]
A
Yes.
- [41:59]
B
Cfpb. Yeah. So it's probably. It was a dual CFPB FTC matter where basically all their influencers were saying, you don't pay anything ever. You know, kind of like really not like, not even just not having TILA disclosures, but just like completely misrepresenting the product. So they had to come up with a process very similar. So I love this. I love being able to talk about Kanye and Taylor and commercial law and ip.
- [42:20]
A
I just. Everyone thinks lawyers are boring.
- [42:23]
B
Exactly. It's literally exactly, Exactly. All right, so let's go to lightning round or closing reflection. Five years from now, what does the legal department look like? What does a great one look like?
- [42:36]
C
Lauren, I think you gotta keep up with the times. I think you need to embrace the AI. I think you need to really not retire your lawyer hat, but also really wear a business hat as well. I think we've kind of touched on that through the conversation that, you know, we're just as much here to help with the, the legal issues as we are with the business. Like, how do we really, you know, streamline, make sure that we're hitting milestones, make sure we're delivering the best products, make sure that we're also covering ourselves in the event of, you know, anything were to happen. So I think we really need to like, lean into the AI. What can we take away that's, you know, bogging us down, you know, spending less time, maybe, you know, reading emails. How do you automate that? How can you have someone, like, give you a summary of everything that you received overnight, like that type of thing? So I think it's really, you know, leaning into technology as well as developing your business knowledge and, you know, being smart and creative within the industry.
- [43:46]
A
My turn, I would echo a lot of that. And part of that is what I always think is, you know, they're going to need to be savvy AI users, not just in the legal space. So automation across all things, right? Your, your calendar, your Gmail, writing, your performance reviews, like, folks are going to need to be sharp on all of that other stuff so that you're spending your highest ROI time on the big things. And I think another portion of the five years from now is what's the relationship with outside counsel look like? You know, those, those fees are just going up and up and I think the, you know, law firms are going to have a bit of a change over the next few years of how are they going to do that? You know, they're going to need to provide different services like diligence reviews and things like that at either lower cost or using these tools. So I'm actually really curious to see and I think a lot more in house teams will be relying on themselves on some stuff that they're not today because we'll be able to spend more time on some of the higher ROI things Ourselves versus, like, I got to get all this other stuff done. So let me call outside counsel on this question. So I think you're going to see leaner teams and probably some, in certain areas, less reliance on outside counsel.
- [45:03]
B
What do you still go to outside counsel for today?
- [45:05]
A
Question for me, I think the big thing that I'm finding, like, where are the gaps into that thing where the two main areas I go to outside council still for are I really, really want the market data. So it's like something maybe we haven't done before. And I gotta go tell my CEO, like, look, most people are doing this. Here's the high end, the low end, let's make a decision for us. And I just obviously won't have that from. Especially working at two companies. I got a lot of friends, but it's nice to just get that full market data. And then probably the second is when you need a really specialized thing. So there's probably certain areas in the insurance regulations I'm going to need to go talk to somebody about or a crazy new privacy law or something like that. But other than that, Lauren can attest to, and I give Enrique and Andrew over at Wayfair a lot of credit, like they instilled in us to, you know, we can do a lot ourselves. You're all smart people. We had worked at law firms, a lot of us, and so, you know, we always kind of were of that mindset of you really go for the, for the high, for the high ticket items.
- [46:09]
B
I love it. All right, let's do a lightning round to close. So a book leader or podcast that shaped how you think? Lauren.
- [46:17]
C
So I think a leader is my mentor, really shaped how I think. You know, he kind of really championed me to kind of own my knowledge on my business inputs, like all of that. I think when I first started, I was a little, kind of had imposter syndrome. And I was at these companies with, you know, all of these super intelligent people who have worked in Silicon Valley, and I'm just, you know, this junior lawyer who's trying to figure things out. So he really championed me. But I, I think, yeah, I, I don't think I would have like the confidence and the knowledge base that I have without him.
- [46:59]
B
Mary, book leader podcast that shaped you?
- [47:04]
A
I'm good. I wouldn't. So just get. I just read literally this week while I was at jury duty, which was another fun thing, the algorithm by John McNeil. And he worked at Tesla with Elon in the early ages when they were really trying to basically make it more efficient. And actually I was given the book when I was at Wayfair. They gave it to a lot of us to kind of read and funny, the first day I walked in here, one of the board of directors handed me the book and I was like, I just read this, but thank you. But it's fascinating because it talks through basically Elon's, you know, kind of five step. He called it the algorithm. But like, to make something efficient and move fast. And in working in tech, it's just been. It was really, really interesting just to. To have it written down. I think we hear a lot of those things. But how do you move fast while innovating and reducing risk or figuring out the risk to take? And I think reading it as lawyers is really interesting, especially in house attorneys, like, because this is what your business counterparts are trying to do every day. So it's just kind of fascinating and kind of excited to see how that may actually change my mindset a bit as I dig in here.
- [48:16]
B
Love it. We're going to do book club. We'll do gcai, Susie and friends book club. Excited. Lauren and I can catch up. All right, Lauren, what is one piece of advice that you would give your younger self in two sentences?
- [48:31]
C
So I would say that you belong in the room that you are in, and to you, you've earned your seat. So feel like, hold your own and you know, you have the knowledge and the capabilities to be there. So just have more confidence.
- [48:52]
B
Mary, how about you?
- [48:55]
A
You're never actually going to learn at all, because I think I had this mindset of, you know, one day you'll know everything or you have learned all
- [49:02]
B
the laws, you'll reach the end of the Internet. Yep.
- [49:05]
A
And, you know, you're just going to learn to become more comfortable making the decisions. Like, that's really what you learn over time.
- [49:12]
B
Love it. Wow, this has been so much fun. Thank you so much for joining me on the show.
- [49:17]
A
Thank you for having us. Lauren, it's nice to see you.
- [49:19]
C
Thank you. I know.
- [49:20]
A
I miss you.
- [49:23]
B
That was my conversation with Mary Abacher, deputy general Counsel at Everquote, and Lauren Anderson, senior counsel at Wayfair. If you want to see how in house legal teams are using AI and including for fun things like Kanye clauses, head over to GC AI, follow Susie and friends, wherever you get your podcasts, we'll see you next time. Thank you.