CZ and Friends
CZ & Friends is a podcast about what it takes to lead and evolve legal in an era of exponential change. Hosted by Cecilia Ziniti, former General Counsel turned founder and CEO of GC AI, each episode features candid conversations with legal and business leaders who are building for scale, taking bold bets on technology, and leading with humanity. Whether you're a GC, operator, or in-house counsel, this podcast is your front-row seat to the future of legal.
CZ and Friends
Courage and Conscience: General Counsel Jordan Breslow on Integrity and Plain English Lawyering at Etsy, Opsware, and in General
When everyone said yes, Jordan Breslow said no, and that decision kept his company out of scandal.
The longtime Silicon Valley GC (Geoworks, Opsware, Silver Spring Networks, Etsy) joins host Cecilia Ziniti to share what decades inside tech taught him about courage, integrity, and how to stand by your instincts when the pressure is high.
He tells the now-legendary story of advising Ben Horowitz not to backdate stock options just before the Silicon Valley scandal broke, explains why he sent Etsy’s IPO documents back to outside counsel to “rewrite them in English,” and reflects on how lawyers can stay human as AI reshapes their world.
Follow Jordan:
@Jordan Breslow on LinkedIn
Books, Authors & Thinkers Mentioned:
– The Hard Thing About Hard Things by Ben Horowitz
– Adam Grant (leadership and integrity frameworks mentioned by CZ)
Other References:
– Opsware (formerly LoudCloud)
– Etsy IPO and B Corporation certification
– Andreessen Horowitz (A16Z)
– Silver Spring Networks
– ASCAP & BMI (analogy for AI creator compensation)
– Down the Rabbit Hole (band)
– Lake Tahoe residency
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@Cecilia Ziniti on LinkedIn
@CeciliaZin on Twitter/X
@GC AI on LinkedIn
gc.ai website
People were just doing it. So I went back to Ben and said, I'm not comfortable with this. I don't think you should do it. And one of the articles that Ben wrote was not in the book, but he published it on his on his website, uh, is describes the scenario and sort of thanks me for keeping him out of jail.
Cecilia Ziniti:Welcome back to CZ and Friends, the podcast where we talk with legal leaders, technologists, and operators driving innovation inside their companies and beyond. I'm your host, Cecilia Ziniti. Today's guest is Jordan Breslow. His path runs from law firm associate to founding his own firm, then to in-house roles at Geoworks, Opsware, Silver Spring Networks, and now a chapter investing at New Island Capital, as well as a role at Etsy. Along the way, he taught as an adjunct at Berkeley, my alma mater, and NYU law while still practicing in-house. He's got a fun story, and a reason that I've invited him is actually that Jordan was the general counsel for Ben Horowitz, who of course is now of Andreessen Horowitz, and he really talks about how Jordan was everything you need in a general counsel. So we're gonna dive into that and why um literally invited him to the show because of it. Um in this episode, we'll explore speaking truth to power, IP, and AI's questions around creatorship, copyright IP, daily practice of integrity, especially when the pressure is high, which here in the Silicon Valley and beyond that happens a lot. Let's dive in. Jordan, welcome to the show.
Jordan Breslow:Thank you very much. It's a pleasure to talk with you.
Cecilia Ziniti:Excited to be here. So let's start with your timeline. So, when did you become a lawyer? What kind of lawyer have you been? And just give us a general walkthrough.
Jordan Breslow:Sure. Um I graduated law school in 1980 from Hastings Law School. So it's been a couple of minutes now since I've started. And just quick trajectory. I was uh very reluctant to work for law firms and particularly big law firms. I sensed that it was uh going to be a choice between having a life or having a career. So I sought out a small law firm and joined a small firm in Oakland, worked there for a few years, did a little bit of everything, which is to say uh kind of committed malpractice in many different areas, probably. And then kind of got the itch to start my own practice. I started a practice in Walnut Creek, California, kind of in east of San Francisco, and uh built a bit of a technology practice. After I kind of outgrew the ability to serve technology clients in a small firm, I merged my practice into a larger one, an established firm in Oakland, which had larger tech clients, Autodesk, probably the most notable and Software Publishers Association back in the day. So I did all of that, and most of the time while doing that, I was thinking there's got to be another way I could make a living because I don't like practicing law, I don't like timesheets, I don't like billing, it's boring, it's it's tedious, it's thankless. So I was exploring other opportunities and avenues of life, maybe go back to my first love, which is play music, maybe become an electrician. But I got a phone call from someone at a startup in Berkeley, California, which was called GeoWorks. They were looking for their first in-house counsel, and I turned them down because it seemed insane. And about six months went by, I was more and more dreading every day in the office with a suit and tie. And they called back and said, you know, we still haven't found anybody that fits the bill. And I said, okay, I'll be there on Monday. So I jumped ship, went in-house, and started an in-house career. You mentioned the series of uh companies I'd worked for. But working in-house was was not always pure delight, but compared to being in a law firm, it was delightful. So, as I said, we started in GeoWorks, which was a startup in Berkeley. It's a story into itself, but it's my first experience being in-house. Uh, it's the first IPO that I participated in. It's also the first time I realized that the kind of fake it till you make it mantra was going to be my guiding principle for a lot, a lot of the work that I was asked to do since I really had no idea what I was supposed to be doing. But GeoWorks was a great experience. After that, I worked at Loud Cloud, which was started by Mark Andreyson Ben Horowitz. Later changed its name to Opsware, went through a whole series of reinventions, which is much of the subject of Ben's book. Uh, worked there until we sold the company to Hewlett-Packard. I moved to Costa Rica and decided never to practice law again. That lasted about two months. Um, and then I was persuaded to come back to the States and go to Silver Spring Networks, which is a a kind of ostensibly a green tech opportunity, uh, something I believed very much in. Uh worked there for a time, and then uh uh, as you mentioned, I did a kind of a segue out of tech, out of Silicon Valley, uh, and worked for uh an impact investment firm, which is was quite a fascinating place, but something I believed strongly in. I worked there for a while and moved to New York, and then I got a phone call asking me if I was interested in joining Etsy, which was looking for a general counsel. And I had been a big fan of Etsy as a consumer. And so I jumped at that opportunity, went to work for Etsy, went through the IPO process, stayed on for about another year or so, and then retired. Just effectively, I went back into private practice, represented small startups working from home, and moved my home to Mexico and then to California, to New York, back to California. Thank God for the ability to work remotely. It's been a blessing. And then uh I retired. I just recently turned 70. I think I'd had enough of law. Thank you. And so now I'm uh local rock star.
Cecilia Ziniti:Local rock star, that's good.
Jordan Breslow:Yes.
Cecilia Ziniti:That's the apex title, as it were. So so many interesting threads to pull. So take us back to GeoWorks, and you're on the eve of your first IPO, and first IPO is a general counsel. How did you do it? Like, like, I mean, like literally, like, I mean, you had been a law firm lawyer, you obviously I'm sure engaged law firms, but um, you know, at the time, this this would have been, you know, now I think having a tech IPO is sort of a badge of honor for a GC. Um, not sure if if you knew that at the time, but like like put us in your headspace uh at that time.
Jordan Breslow:Sure. Well, maybe just to back up a little bit, I started at GeoWorks on like a Monday. On Tuesday, the president came down to my office and said, We're gonna have to do a bridge loan. We're short on cash. Could you take care of that for me? And of course, I'll get right on that. He left my office and I called a friend of mine who said, What the hell is a bridge loan? So that was kind of set the stage for how I did many things there. There's just no way one can be prepared for all the things that get thrown at you as a general counsel. The word general fits, you know, you gotta do IP and technology and just, you know, human resources and so many different things. So, of course, I relied heavily on outside counsel. Also, just every time I had to do something new, I studied the heck out of it and looked at, you know, the documents people had done before. Uh, I tried hard not to just copy and paste documents. That's something I don't believe people should do. But it's just, you know, again, you surround yourself with good resources, uh, you kind of get smart and build good relationships with outside counsel. So that was kind of the the prototype for everything else I had to do. When it came time to do the IPO, that was my first IPO. I've actually been through four of them at this point. I had really a fairly small role. And and I think it was probably appropriate that I have a small role at that point because I didn't really have a lot to contribute to the process. Mostly my role there was to know who knows what within the company and and make sure those people talk to the the bankers and the lawyers and you know, sort of a conduit to get the facts and the truth out. With each progressive IPO I participated in, my role expanded. The one that I'm proud of, I would say, is the IPO at Etsy. And there I had a fairly leading role. I and and our CFO, we decided we weren't gonna let the outside lawyers or the bankers tell us how to do our IPO. We were gonna tell them how we wanted it done. And that was fun and satisfying. We we did some different things compared to your kind of standard IPO. But that was however many 20, 30 years after my first one, a long time. So uh, you know, I can you can't walk into a complex transaction, whether it's a bridge loan or an IPO or anything in between, and anything in between, and assume that you're gonna add a ton of value. So I think you find where you can add some value and then you grow, you learn, you get better, you get more confident.
Cecilia Ziniti:So that Etsy IPO. So fast forward to the Etsy IPO. And you've got this like you're like, all right, we're gonna tell the outside folks how we want this done, unique to our company. Any any stories you can share or things you can you can go there. One of the things that our listeners or that I've I've picked up over my career of being a general counsel at different companies is that there really is, there's like a way to succeed and a way to do things, and there's a way to succeed at that company, right? And even down to that CEO, right? Where you know it shows up in things like in the GCI product, we actually have a field where you can say how your CEO likes to be communicated with, for example. And that's something that I learned exactly like you of like every every company is a little bit different, and there's a million ways to succeed. So grounding the question, the Etsy IPO, you said you did things a little bit differently. Any examples or stories you can share there?
Jordan Breslow:Sure. Well, a few, I some I'll have to try to remember. But one of the things, uh, something that it's sort of a soapbox I've been in standing on for a long time is I like documents written in what I call plain English or you know, human language. When you get the army of lawyers in an IPO, they have uh it's a word I I sort of love and hate, vetted. Um, their documents, they they work, they get the job done, and those are the ones they want to use, and they're quite terrified to change them. And I sent back to our outside council every single document that they sent to me uh and said, rewrite it. I want it redone in English. It fit my personality, but it also fit Etsy's personality. Etsy is is a human website. I mean, it's a it's a business about small people making a living doing creative and artistic things. And whether it's the employees, the shareholders, or the customers, the merchants, I didn't want to hit them with incomprehensible documents. So that was a pretty constant tug of war. I I would say I won most of those battles, not all of them. There were there were times when the lawyers just said that if you change this, you know, we can't protect you. It's you know, you're committing malpractice, whatever. But most of the time it was written in in fairly plain English. Another thing we spent a lot of time thinking about at Etsy was um, this gets a little technical, but we were a certified B corporation, certified Bibby Labs. We were the, I think not the first, but certainly the biggest public company to be a certified B lab corporation. And we worked hard at that, and we wove that into our prospectus, into our story. I had to spend time on the phone with the SEC at that point, trying to help them understand what this means. You know, was it okay? Was it kosher with them? What, you know. So we were successful in in that. For those familiar with the laws of social enterprise, there's a difference between being a certified V Lab corporation, which is really a private company certifying you in a kind of a good housekeeping seal way, and reincorporating as a company goes by various different different names, a benefit corporation or what have you. Um we wanted to reincorporate, be a benefit corporation, not just certified, but be a benefit corporation, which gives the the directors and the company certain obligations to the shareholders and to the public. Um and at that time there were technical issues in the Delaware law that kept us from from doing so. I went and met with the commissioner corporations in Delaware and persuaded them to change the rules, but not in time for our IPO.
Cecilia Ziniti:So Wow, that's a good thing. I I hadn't I hadn't heard that story. I wasn't familiar with it. Now with ESG and the CSRD in Europe, it's definitely sort of at the forefront. So so basically, so this was an example of like SGC, you basically pioneered the new law. And then and so did Etsy end up going back and and reincorporating later?
Jordan Breslow:To my knowledge, no. No, I don't think it did. It it gets close to impossible. One of the uh I'm trying to remember back now into the weeds, but there's a shareholder vote requirement for converting. Certain number of your shareholders have to agree to convert from a traditional corporation to a public benefit corporation. And it's a threshold that would be nearly impossible to reach once you're public. You know, you have so many more shareholders, and to get I forget what the was it three-quarters or whatever it was, vote in favor of that.
Cecilia Ziniti:Once you're public, interesting.
Jordan Breslow:Yeah, right. So we just did the best we could to act according to the principles that we would have followed anyway as a public corporation.
Cecilia Ziniti:Love that. The the plain English theme of like making sure that even a relatively dry legal document, a prospective, a proxy statement, what have you, can reflect the company. It's a great example. So a friend of mine, Eve Saltman, was the GC of GoPro at the time of their IPO. They did a video. They literally did a video on a GoPro as part of their prospectus. And at the time it was very controversial. And now I think companies have followed suit, but it's a great example of like, if you're gonna be a shareholder in GoPro, you gotta be into video. If you're gonna be a shareholder in Etsy, you know, it's sort of like this human creativity and it's a consumer company. And it's something that I think about now. Like I'm so glad that you highlighted it for the pod, is that like a company is really, you know, reflective of these like very human things around who are the people at the helm company, who are the users, who are the like what is it? And so that's been really it's been fun for me, but also sort of shocking as a as a CEO now that like things that I'm into, like even something like emojis, they're like part of our brand. Or like the fact that I'm super into giving very pragmatic legal advice, like you just explained, and people are constantly telling us, like, wow, GCAI really does give like bulleted advice that lands with our message, plain English, kind of like translating to land the message. So that's yeah, you hit on something profound. What was it like working for Ben Horowitz? Um so let's take a detour there.
Jordan Breslow:Sure.
Cecilia Ziniti:The story. Um, so basically we'll drop it in the show notes, but um, Ben Horowitz wrote a book. Um, so he is, of course, the founder of Andreessen Horowitz, and you know, has invested in all the iconic companies of our era and really created uh basically a new generation of venture capital and the spirit of the founder that he was, and in case in this case, the founder that he was uh with Jordan and with with Mark Andreessen. And I guess the the book is called The Hard Thing About Hard Things, and it's um styled as uh advice for CEOs. But it's a really big deep dive into how you know create a high growth company and and how how you you have the success that he's had. But one of the stories that he tells, so I'll I'll let you tell the story, or I'd love for you to tell the story, Jordan. So so so what happened and how does Ben Ben talk about it? And and and what's the takeaway?
Jordan Breslow:Well, let me back up to the you started with what was it like to work for Ben. Um and it was delightful, it was frustrating, it was so many things. Ben is a complicated person, he's a super interesting person. You know, I adore him. I mean, I just he's just uh unique, and we had a good close relationship. We talked a lot about music and politics and just many, many things. We also had very different personalities. And uh I could tell a slight funny anecdote, but just uh he's a big Raiders fan, the football team, the Raiders. He wrote he once wrote a review, my annual review, and in it he said, Jordan, you're you're doing everything right. I can't fault you, you're getting all the results we want, you're you're highly effective, blah, blah, blah. And if I had to give you any advice, I'd say that you just don't have enough bravado. You need to have more bravado. And um I kind of marveled at that and laughed about it, and I still laugh about it because I thought that was kind of funny to be saying you're doing every doing everything right, but you should change your personality to be kind of more of a more, you know, more of like a jock and you know, punch people on the shoulder kind of thing. And I thought, okay, that's interesting. I just mentioned it because it's part of the complexity of who Ben was. Very thoughtful, creative, but I would also say, you know, like he would fairly often he'd say, Hey Jordan, let's sue these people. You know, they're pissing me off, I want to sue them, you know. And I I almost always talked him out of it because, you know, lawsuits are just for the most part pretty stupid waste of time and money. So there was, you know, we had a kind of a good symbiotic relationship, I would say. You know, he describes me in one article that he wrote as uh coming from Berkeley and having hippie sensibilities, and I think that's pretty fair. Um and Ben also grew up in Berkeley and was the son of a lefty who became a far right pundit. So it just an interesting thing. And Ben's very into rap and hip hop culture. Every one of our conference rooms was named after some hip-hop artist, and every time he sent a memo to the staff or to the company, it started with a quote from some rap song. Um, so just an interesting thing.
Cecilia Ziniti:He said that in the book as well.
Jordan Breslow:He does in the book as well.
Cecilia Ziniti:Right. That's fascinating. So and even just these like these personality aspects that come through. Like that. Yeah.
Jordan Breslow:There's a lot of personality to Ben. So along the way, we had already become a public company. We hired a new CFO, and uh, she'd come from a company called Mercury International, and she had recommended to Ben that we adopt a practice that they had adopted at Mercury, which the short phrase is backdating stock options. Technically, it wasn't exactly backdating, but you know, the principle of a stock option is you're supposed to value the option, price it at the value of the stock on the day of the grant. And what Mercury was doing was picking the value out of the past 30 days, the lowest price on the past the 30 days prior to the date of the grant and say, let's go with that. So if if the value fluctuated over the course of the month before you get your grant, your grant would be priced at the lowest price that had occurred in the past 30 days. So she recommended it highly. Ben came to me and said, Jordan, our CFO wants to do this. What do you think? And as going coming back to my bridge loan question, I said, I have no idea. Let me figure it out. So went and researched it. I talked to other GCs, I talked to our outside counsel, and it seemed like everybody was doing it. But nobody could convince me it was legal, or at least accurate and honest. And even if it was legal, are you accounting for it in the proper way? People were just doing it. So I went back to Ben and said, I'm not comfortable with this, I don't think you should do it. That's that's the short version, I guess. Um, and Ben said, Well, Jordan, I trust you, I trust your judgment, so we won't do it. So we didn't do it. And shortly thereafter, the stock option scandal erupted. The SEC started chasing companies who had done this. Some people went to jail over it. Um, people, a lot of people lost their jobs, some general counsels lost their jobs, and I feel we're probably thrown under the bus. But it was uh a big storm. And one of the articles that Ben wrote was not in the book, but he published it on his on his website, uh is describes the scenario and sort of thanks me for keeping him out of jail, effectively.
Cecilia Ziniti:Love that. It's good. Yeah, so you've talked about since then and through that story, just the integrity of it. Is that really the core? That's the core of the job, right? Or how do how do you think about it? And you know, you get in there and we we talked about the IPO and you build your skills and you want to be a great GC. But like, I mean, that's a uh an important moment. But how how do you think about that as being the job or or not the job or how is it part of the job?
Jordan Breslow:Aaron Powell I think it's fair to say that that was, as you said, a moment. And moments like that happen with varying degrees of frequency. You know, it's not a daily occurrence, right? You're in in Silicon Valley, something crazy happens every day. But most of the time it's just how do we get this done? Let's get busy, let's get creative. And and it it's not moments where your integrity is is challenged. I just think it's a matter of keeping uh your sort of ear open to situations that don't feel right. And, you know, the simple saying is trust your gut. There was something about this backdating thing, even though it wasn't even called backdating at the time. It was just a way to arrive at a value for the grant. But there's something about that that said, this doesn't feel right to me. So I'm gonna not just do my usual lawyering, you know, throw this transaction together or whatever. I'm gonna think about this kind of hard. I'm gonna talk to people, I'm gonna take take advice. The challenging thing for me in this one uh is that the advice I was getting was from some very prominent Silicon Valley lawyers and law firms saying, this is okay. Everybody's doing it. It still didn't feel right to me. And I guess what my gut was saying is just because everybody's doing something doesn't make it right. So I think it's just keeping a little bit of your antenna up all the time. Like, is this just another transaction or is there something about this that doesn't feel right? If it doesn't feel right, listen to that.
Cecilia Ziniti:Yeah. You know, it's interesting. I I felt a little bit that way about SPACs. So there was a period of about two years or maybe even less, about a year, where the hottest thing was specs. And it was like, we're gonna do this. And um and and I even at the time I was looking for a new general counsel role and I hadn't had a IPO experience, and I hadn't had specifically SPAC experience. But I remember thinking, like, this seems too good to be true. Like IPO is a thing for a reason. Like, and I had that same idea, but it is very hard to to stand up in that moment and do it. So, like any advice for, you know, younger GCs or people who didn't, you know, at that point you had been a public company in your prior role, you had interacted with the SEC, you were at least, you know, had enough expertise to be able to question the the expensive law firms telling you what they told you. How do you how do you do it? Like is it is it just the hippie sensibility or or like what what is it? And and I'm, you know, imagine whippersnapper me or whippersnapper version of me facing that kind of situation. Let's say it's once a year, twice a year, depending on the the situation. What do you what do you do?
Jordan Breslow:Good question. Well, part of I'm not sure this is directly to your question, but I think it forms the way I think about it, is one of the reasons Ben was willing to listen to me and even stop something in its tracks, is that I was in the habit of finding a way to say yes as many times as I possibly could. Um and this is something I've mentored a lot of lawyers along the way, particularly younger lawyers. You know, and uh and coming out of law firms, it's it's it's a great education, but it's also a handicap because you're mired in the sense that your job is to identify risk and mitigate risk. And so you sort of see anything and you think, how can I say no to this, or what's wrong with this, or you know, where's all the risk in this? I've got to raise a bunch of red flags. And uh that just had never been my style. Obviously, I would identify internally what the risks are uh in my head. Um, but that's only the first part. It's like, okay, this is a this is a challenge. Now how do we do it? And how do we mitigate the risk? But how do I get the prime objective of closing this deal or buying this company or doing this IPO? You know, first thing you have to do is build trust um by being an ally um and and not you know, not being the naysayer. So that's part of it. Part of it is building a personal relationship. So so building the relationship with the person you report to, or in this case the CEO, was also super important. Um so both of those gave me the confidence to say, uh-uh, at various points when when my gut was telling me this is not right. I don't think I could have started my career doing that. Just to be realistic, if I'm giving advice to young lawyers, it's you know, it's gonna take a little while, I think, before you have built trust in yourself, others others trust you, and before you can sort of prioritize the wrongness or rightness of things that are being done in business. The business world is not the same as the real rest of the world in my mind. You know, people stretch the truth all the time. People take shortcuts, do things that are bottom line focused that aren't necessarily human focus. And if I said no to every single every time I was uncomfortable because of that, then I would have failed quickly. So it's in another another way of saying it, I suppose, is you choose your battles, keep your antenna open when something really feels wrong. Find find a way to say no. Ideally, which didn't much happen in this case, but ideally find a way to say uh no but or yes and however you want to put it. But you know, let's not do that. But here's something else we can do instead that'll get the result you want. That's the best outcome, I think.
Cecilia Ziniti:I love that. Also, some good themes. We had Doug Lees on the podcast a few weeks ago, and he put his entire team, he was a GC become CEO, and he put his entire team, 2,000 people through MPOF training, where it was literally the yes and of like, okay, you know, and but this corollary of like be yes and so that when you say yeah no, you can mean it and you will be listened to. I think that's the maturity and uh a journey that has been a theme, you know, for certainly in my career, but also, you know, on this podcast and also just for for in-house legal, but just also for business in general, right? That it's like that is something to that the like builder's mindset that obviously uh, you know, Ben Horowitz has has espoused that that getting there and being part of the journey and having you know a rewarding career where you're listened to and have an impact is like you you have to figure out that balance. I I love that advice. So this is a good one. Um, I'm gonna I'm gonna clip this one out. So, so watch out my LinkedIn. It is coming. But uh good advice. Awesome. All right, so let's switch gears a little bit. Let's talk about AI. So obviously, Etsy, big part of your role there would have been brand protection, would have been IP, copyright considerations. You mentioned you're a musician. So let's start with the kind of macro question. Where do you think this sort of like IP do creators get rewarded if their um work is used for AI? Kind of the big, sort of big fair use question. What's your take?
Jordan Breslow:Yeah. Um well, I do lean heavily in favor of artists and creators. Um fancy myself one at times, surround myself with musicians, computer programmers, authors. And I think copyright law has throughout the years struggled to maintain a balance so that authors, creators are rewarded, but don't end up sort of monopolizing their creativity. And that's the sort of the inherent struggle. And copyright law, sometimes it's done a good job of striking that balance, sometimes not so good. I feel what I would like to see is a system somewhat analogous to what happens in in music. So I mentioned I'm in a band, we play cover songs. I make my you know tens of tens of dollars a year as a musician, sometimes even a hundred dollars a year as a musician. So it's a hobby. But I get up on stage with my friends and we play songs written by somebody else. And so I'm profiting, even though it's not much of a profit, but I'm profiting personally and emotionally from somebody else's work. And so I realize that person might not appreciate it. In the music world, there's through Ask Cap and BMI, there are mechanisms for the creators to be compensated. So if a venue has musicians playing in it, the venue gets a license, the money goes to ASCAP, it gets distributed out amongst the authors, the publishers, et cetera. Um, it doesn't always necessarily compensate them well, but I would like to see some sort of analogous system. It seems to me, from a legal point of view, from my study of the cases in IP law, correct analysis that if you're using all the works of all these authors to train your AI model, you don't have to pay them for it, at least under copyright law. That seems like the right, technically correct answer, but it feels wrong. And it feels wrong partly because some people and a small number of people are getting inordinately wealthy or trying to get inordinately wealthy or wealthier by taking advantage of this aspect of copyright law, that they don't have to pay people. And yet they're gonna, in one way or another, monetize their AI. They might be making it available for free right now as a teaser, but they're in it for the money. And it bothers me that they're gonna profit off the off the labor of all of these authors. I don't know that you know the copyright law is gonna get to the point where I would like it to be. And and I think for good reason. If uh if I read a book and I learn from it, you know, I don't I shouldn't have to pay an extra fee because I learned from it. And if I, you know, so I think it's a legit point, as long as the the AI isn't itself producing output that's a copy of the original.
Cecilia Ziniti:I think that copyright will have a technical distinction, yeah. There's a regitation point. Yeah, so a lot of I mean it's funny because I thought when we did the show that the kind of does something feel right, sort of instinct things that trust your gut we talked about would not actually translate to this segment of the show, but I think it does. Like, and this is something that I've said where, you know, is this the Napster moment where you know Napster came out when I was in college and we had basically like a server where you could get any music you wanted, and that that's totally how it worked. And I knew at the time, you know, a little sketch. Like I remember thinking that. And it was like we needed that commercial framework to come out, and eventually, you know, obviously we have iTunes. So I do think there is a commercial solution. I like that, but I also like the sensitivity of like, okay, in music, this exists. Can we create this for AI? So yeah, that'll be interesting. That'll be interesting to see. I think it's the it's the it's the the thing of our era. And also, you know, a little hint of platform stuff there too, right? You know, obviously a lot of creators on Instagram, a lot of creators on social. And the really, really ultra rich are of course the people that own the platform. So yeah, that's that's fascinating. So so what do you think any any I mean, the bold prediction, do you do we get there? Do we get to some kind of system to reward creators for the use of their work in AI? Like tactically, how do we go from from iTunes to Napster in AI? What's your what are your predictions? Or Napster.
Jordan Breslow:You asked me that in a in a moment where I'm I'm uh perhaps overcome with a l a a fair amount of pessimism about accomplishing good things in the near term. We don't need to dive into politics, but suffice it to say, I feel like we're moving in the wrong direction in in a lot of ways as a country and getting kind of interesting legislative creative solutions, it doesn't seem like this is the time when that's gonna happen.
Cecilia Ziniti:And that is that is something where the these kind of waves of of political view, but also of is actually tied up in copyright and it's tied up in other considerations that you mentioned.
Jordan Breslow:Mm-hmm.
Cecilia Ziniti:That's a good I think that's a fair, fair assessment. Um all right. So in terms of litigation, if you were you've been in companies that have had litigation, you've managed litigation, if you were advising a startup today in this space, um, what what's what's your advice? So let's say you're a hot AI startup and you train on on lots of stuff. What's the what what are you telling them?
Jordan Breslow:About litigation. I'm so not sure I understand your question.
Cecilia Ziniti:About going into a high risk area. So one of the things that another um Andrees and Horwitz partner, Andrew Chen, talks about, he was early Uber. And he makes the case that essentially the fact of Uber is illegality, like that there were taxi medallion requirements and other permit requirements in all the cities in which they operate, but basically the stomach to sort of be like, all right, this is technically illegal, but we're gonna, we're gonna talk with regulators, we're gonna make this happen because that's what the business model requires. So he talks in his book, Network Effects, about that. He's talked publicly about it. But I guess for startups in either regulated areas or creative areas, privacy, all these things, like, you know, if you were hired as a GC of one of an AI type company, well, first of all, would you take a job? So maybe that's that's the question. You know, you're retired, but assuming you weren't. And second of all, you're hired. Are you like, all right, you better raise a lot of money to pay for this? Are you like, okay, you know, do these other things to make this okay? You know, do you what's the I get asked this a lot. I got and now that I, you know, sort of people know that I'm a GC and I have a feel, you know, feel strong about these issues, I get LinkedIn DMs basically all the time asking that. So assuming that I'm feeling I'm in a good way and I feel like I want to help these folks, what what am I telling them?
Jordan Breslow:Yeah. Well, I'm gonna maybe back up would I take the AI general counsel position? I would not. Partly because I'm retired, but that but even setting that aside, um I spend a lot of time in tech. And I, for the most part, have very strongly mixed feelings about whether tech is good for the world. And I have great misgivings about AI as the next thing that's not going to be great for the world. And I guess I believe strongly in the sort of the law of unintended consequences that, you know, be careful what you create and careful what you wish for. If there were an opportunity to work for an AI company that was sort of mindful of all of this, and I I'm sure they're out there. I I know people talk about, you know, we have about their their standards of controlling the AI and alignment with human issues and morals and that sort of thing. So that might be interesting. It's like, I mean, the AI, it's here, it's coming, it's coming faster than we even thought five years ago in terms of you know moving towards sort of more general intelligence. So it's coming, and maybe this is this is something I think about a lot actually. Uh is like, is it better to opt out of participating in something or get involved and hope to have influence from within to steer it in the direction you'd like to see it go? I think that's a timely question in general, because a lot of people, whether it's in private industry or even more notably in the US government, are being asked to do things that they don't want to do. And the question is, should I stay? Maybe I can influence this administration or this business executive team from inside, and so I'll stay. Um, or maybe that's just a pipe dream. Oh, I'm being uh, you know, I'm just gonna be co-opted into doing things I don't believe in. So I'll qualify my would I take the GI G C position. I probably would if I thought I could influence it and the people around me were were values aligned. Okay. But I would not want to just, oh boy, AI is the greatest next thing, and I'm gonna get, you know, rich off the next IPO. I have a lot of trepidation about where I AI is gonna lead our society.
Cecilia Ziniti:Um interesting.
Jordan Breslow:That's that I love that.
Cecilia Ziniti:But I think it's an important point where I've actually seen, you know, had that exact calculus where I've seen people do that very successfully. So at Amazon, I was a product counsel, and one of the responsibilities I had was compliance with the CBAA, the Communications and Video Accessibility Act. And um, it was essentially making Amazon services compliant for for use by individuals who are blind or individuals who have hearing impairments and so on. And we had an incredible basically director of accessibility, and he said, I've been an advocate for accessibility for two decades, but the impact I can have here at Amazon, having the influence to do so. In this case, we did we launch video descriptions, but essentially that he could take this like goal of being good for the world and from the inside, exactly as you said, have far more significant impact than he could from the outside. So that's that's interesting. I I love I love that that point. You're you're hitting on all my big, the big rocks in tech of what I think about. So this has been a super fun conversation. So let's um let's go with some quick takes. So a book, idea, or mentor, podcast, what have you that's influenced your leadership and your life.
Jordan Breslow:You know, uh I knew you were gonna ask that question, and I have struggled to come up with a an answer that's really no, there is no, I just can't think of a single, single particular book. I I did uh when I first joined Loud Cloud, um, I was not the original general counsel. The the general counsel is a man named Chuck Katz, who I I'm very fond of. And the one thing he told me is to lead with praise, and I think that's just generally good advice. I've worked in cultures where shaming and humiliation are the order of the day, and I don't think you inspire great work out of anybody through fear and intimidation. And so if you're managing people, you know, you have to coach them and get them to do better, perform better, be them be their best selves. But I do think it's a useful paradigm for all your interactions with people who you're training or leading along the way. So I'll leave. Give you that.
Cecilia Ziniti:All right. You've said before that life is too complicated for a single piece of advice. But besides, so you said leave with praise, you said say yes and so that when you say oh no, you don't be trusted. Anything else to leave our listeners with?
Jordan Breslow:I think just be yourself. I think try not to. I think a lot of us grow up seeing lawyers on television and trials and we have this whole image of how lawyers are supposed to behave. It's always again, and it's back to my conversation with Ben about bravado. Um not full of bravado, and yet I was very successful, you know, in in my what I needed to do because I was myself.
Cecilia Ziniti:I love that. Yeah, it it was like I I keep coming back. One of my my idols is Dolly Parton, and she says, figure out who you are and then do it on purpose.
Jordan Breslow:It's like that's I've definitely seen that.
Cecilia Ziniti:I love it. I love it. I love it. Um, where can listeners connect with you? Um, I guess maybe they need Costa Rica tips or anything like that. And what where should they go?
Jordan Breslow:Oh LinkedIn is probably, you know, if a way I as I said, I'm you know, I'm retired, but I'm still happy to give people counsel and advice. I along the way I had some people who I had a mentoring relationship with where we'd get on a video call once a month and just talk about their career, what's going on at challenges, that sort of thing. So I'm available for that. So LinkedIn's probably good. Uh other than that, come up to Lake Tahoe in the North Shore, which is where I live. You can hear my band called Down the Rabbit Hole. I perform at mostly summer concerts. So you can find me there.
Cecilia Ziniti:I love it. And it has a legal link too in the title of the band. I love that. So good. Awesome. Jordan, this has been so much fun. Thank you for joining us today.
Jordan Breslow:It's been my pleasure. Lovely talking with you.
Cecilia Ziniti:That was my conversation with Jordan Breslow, a lawyer who's shown courage and kindness can coexist and that you can be yourself and be incredibly successful as a lawyer, as he has been. If you're thinking about what it means to lead with integrity, especially as AI and technology keep reshaping our world and our work, I hope this conversation reminded you that principle can actually be a form of power. Follow Suzy and friends wherever you get your podcasts. You can follow me on LinkedIn, you can follow Jordan on LinkedIn. Thanks again for listening, and we'll see you next time.