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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
Ask.com to AI: Doug Leeds on Curiosity, Persuasion, and Reinventing Leadership
Doug Leeds has lived through multiple technology booms—from the early internet to today’s AI wave. As CEO of Ask.com and IAC Publishing, he went head-to-head with Google, scaled digital publishing, and even pivoted a search engine by partnering with his fiercest competitor.
Today, Doug teaches leadership and persuasion at UC Berkeley’s Haas School of Business and is co-founding a nonprofit, Really Simple Licensing, to create a licensing protocol for AI and the open web.
Follow Doug:
@Doug Leeds on LinkedIn
You’ll hear:
– Why leadership is persuasion: “getting people to do what you want as if it’s their own idea” (23:09)
– The Catch-22 of being a lawyer-turned-operator—and why he calls law a “better hobby”
– How improv training for 2,000 employees built trust, creativity, and psychological safety
– The WAPOTI framework: “Why Aren’t People Already Doing It?”
– The Three H’s of communication: heard, helped, or hugged
– Why legal should act like product managers, co-designing solutions instead of saying no
– How Really Simple Licensing (RSL) could reshape the economics of content and AI
Doug shows how leaders can evolve across industries and cycles, turning disruption into opportunity with curiosity, persuasion, and yes, silliness.
Books, authors & frameworks mentioned:
– Getting to Yes by Roger Fisher and William Ury
– The Three H’s framework (heard, helped, hugged)
Follow us on all social platforms to get each new episode when it drops.
@Cecilia Ziniti on LinkedIn
@CeciliaZin on Twitter/X
@GC AI on LinkedIn
gc.ai website
Leadership I use in the class is the ability to get other people to do what you want them to do as if it's their own idea with interest and desire of their own. Right. If I did something well, they would say, Oh, you did a great job on that. Now we're going to give it to a business person because a lawyer shouldn't have it now that's doing well. And if I didn't do well, both of these things happened, they would say, Ah, this is what happens when you let a lawyer do it.
Cecilia Ziniti:Welcome back to CZ and Friends, where we talk with legal leaders, technologists, and operators driving innovation in their companies and beyond. Today's guest is Doug Leeds, whose career spans CEO roles at Ask.com, IAC Publishing, and EClub, and now Doug is teaching leadership at my Alma Mater UC Berkeley. Doug has scaled global consumer internet brands, driven transformative acquisitions, and negated the pressures of being a public-facing CEO. In this episode, we'll explore what it takes to lead through change, lessons Doug draws from multiple tech booms, including Early Internet, where he and I work together, and how he's shaping the next generation of leaders to think critically about persuasion, creativity, and AI. And he started as a lawyer. So fun fact Doug and I met back in 2003 when I was a paralegal at Yahoo! Yahoo had acquired a company where Doug was in-house counsel, now called Overture at the time go2.com, the company that invented sponsored search, now a basically trillion-dollar market. Let's dive in. Doug, welcome to the show.
Doug Leeds:Thank you so much for having me. It's so nice to catch up with you.
Cecilia Ziniti:Excited to do it. Doug, you began your career in law and policy before moving on to operating roles at Yahoo, and then later becoming a CEO. So, what did you like about being a lawyer? And then what eventually drew you to the business side?
Doug Leeds:So I the intellectual challenges of the law profession, especially in-house, I thought were just wonderful. Like still is like a hobby to me. And we'll talk a little bit later about what I'm doing now. It kind of blends back into some of the law stuff because I just find the issues really interesting. And I always have. So I still like go on a holiday every year with my law school friends and we talk about legal issues because I enjoy it. So for me, it's it was wonderful, but it turned out to be a better hobby than a profession.
Cecilia Ziniti:Interesting. So when you did you like tell us about that shift, right? Where you just like you got you you did more of like commercial roles, where you got more of like a BD sense, or like a lot of our listeners are, you know, currently in house counsel and perhaps aspiring to um you know a journey that you took. So like stepping into that that moment, what what what kinds of things did you do? And how did you realize the law was a better hobby?
Doug Leeds:Well, I so actually before we met, which was in the legal department at Yahoo, I had uh I had left law, failed attempt to leave law, actually. So I was two years at a law firm and got out because I knew I didn't like law firm life. They made it easy for me because they told me I could either choose the firm or my family. Um said that specifically to me, choose your firm or the family. So I was that was a huge gift. I'm like, great, I'm gonna choose the family. And went into a policy role at a company that got acquired, and I they gave me a bunch of money to leave, like literally five times my annual salary to go away. So it was across the board. They were it was fantastic. Stroke of luck. So I'm like, great, I'll start a company and that's what I want to do. I wanted to build something, I wanted to create something. That was what really was my passion. And then got into the dot-com era where it was going great and then busted. And the question about what do you want to do, firm or family, came up again when my wife's like, you know, that law degree? You might want to start using that again now that you don't have anything else um going on and you have three daughters at home. And so I went back. But luckily, the law in-house job I took at Overture at GoTo was full of people who didn't want to be lawyers, also. It was a really great, and most of them ended up not being lawyers eventually. So it was a great, and it was a startup, so we all got to do lots of different things. And so I kept doing stuff that wasn't legal, even in the legal position. And when we got by got bought by Yahoo, that stopped in large measure. Yahoo was a much bigger company, a much bigger law department, um, a much more defined role. And it was like, no, you're in legal. And I kept trying to do things that were on the edge of it, pushing into doing products and building stuff. And I got caught in this scenario where if I did something well, they would say, Oh, you did a great job on that. Now we're gonna give it to a business person because a lawyer shouldn't have it now that it's doing well. And if I didn't do well, both of these things happened, they would say, Ah, this is what happens when you let a lawyer do it.
Cecilia Ziniti:That's amazing.
Doug Leeds:It was a catch 22 that ultimately I had to find something else.
Cecilia Ziniti:Love that. I I think these themes of like, I've definitely had this in my career where it's like you kind of like just do things because you're almost like compelled, and the structure is like not quite there. So interesting. So you went on to lead Eat Club and you scaled it to basically leading in corporate food delivery, and then you got it acquired by Compass. Um, before that, you founded and ran IAC Publishing, which was one of the biggest digital publishers at the time. So these kind of chapter moments, like you've painted a picture of sort of like you know, the personal and the preferences kind of kind of nudging you in a certain way. But what's the through line among the different chapters that you know leading you to today?
Doug Leeds:I think the through line is curiosity and being interested in new things and learning. I I'm teaching now at Haas. They have these things called defining leadership principles, and one of them is students always, another is question the status quo. I love both of those. I think that's what's been interesting to me, even in in the legal side, which is what can we do differently? How can we look at this that hasn't been looked at before? And so for my career, it's been a progression of doing things that I haven't done before because they really motivate me. Yeah.
Cecilia Ziniti:So obviously early internet was a big one, e-commerce, advertising. You know, it do you do you have like a do you do like a pros-cons, or do you like, you know, you you see what you're reading? Like what do you like little cause because I'm thinking like like for me, it's it's something that I I sort of do naturally and people ask me that, and I'm I'm not quite I never have a satisfactory answer. So what what how do you spot opportunities, especially in industries?
Doug Leeds:Yeah, I think having a good group of people that you trust that that trust you, that there's like good psychological safety, and so that they bring up problems that need to be solved. That's the key thing is understanding where a problem needs to be solved. Because then you can start collaborating and figuring out how you might solve it. Now, that might be internally. The the IAC publishing came out of problems we were having at Ask. So we created that because we were solving problems. But we wouldn't have solved those problems if we didn't have sort of that culture of we can tell you when something is wrong or where something isn't going right. And I don't, as a leader there, it's very important not to take that out on them personally. What do you mean you this is not going well? No, it's actually tell me more. This is exciting. How can we fix it? How can we change? That shows you a path to opportunities. I hadn't really done it as a startup. I'm about to do it or about to launch before. It's usually going into a bigger company, getting to know the people there and understanding the problems they're having, and then looking for opportunities maybe to pivot within a company. That's been sort of how I've done things in the past.
Cecilia Ziniti:So ask.com, besides the amazing URL, um, tell us what the business is. And then the way I see it now, you know, Chat GPT and AI are sort of like that ultimate promise of an ask.com. Yeah. So did did you have that vision at the time and what what was the business? So orient us a little bit to what was the business. And then, you know, ultimately, at the time, obviously generative AI didn't exist. Did you hit that wall as a business? Give it give us a little bit of a of a picture.
Doug Leeds:Yeah, sure. So I I had left before AI was really a factor. We had other things. I came in after we stopped working together, which is I think 2006. I find it so interesting that we were working together in 2006, and I said, I want to leave law, and you said I want to go to law school. Like it was. Exactly.
Cecilia Ziniti:No, it's amazing. And we had folks like Michelle Kunanon at the time. She went to Meta and she was like employee 300 of Meta. And you know, for a while I had this kind of Silicon Valley sort of like, oh man, I should have done that. But obviously, connecting the dots, just as you said, I'm just so happy. Like, and it's so fun to talk with you. I'm literally like, how did you get there? So yeah, tell tell tell me about Ask.
Doug Leeds:Yeah. So I I came to Ask. It had just changed its name from Ask Jeeves, which was sort of the famous, you know, original search engine. We had just been purchased by IAC, which is a big public holding company, um, had many, many companies, many famous companies there. And they had paid uh Ask Jeeves Private, and it was a public company, to sort of serve as the foundational interconnection between all these other brands that they had. They're like, oh, everyone gets traffic through search. What if we owned a search engine? So I came in to run product originally there, and the problem we were having was that Google was kicking our butt. I mean, that's just it was it wasn't even a product issue. It was more of a brand issue. Like we would innovate, we'd create new things, we'd release them, and then within a week, Google would copy them. And within two weeks, the world would say, I like Google because they have that thing that we created. Um, and it was pretty frustrating from a product perspective asked at asked, creating these things, feeling really good about what we're doing, seeing them instantly copied, and then getting no credit for them. What that meant was we had a brand issue. Um, or put another way, Google had no brand issue. Like Google, I used to be asked this question, it would drive me nuts. How do you feel about competing with a company whose name has become a verb? Like you Google it. And I'm like, you know, ask was a verb first. Like you can ask something before you can Google something. But it didn't matter. Google had taken over and had 90% market share. And so it was it was a challenge to figure out what to do about that. Um, but that's one of those moments we were talking about. Like, how do you what do you do with that? Um and first thing I did was I started acquiring other companies and giving us some diverse business. I bought dictionary.com first.
Cecilia Ziniti:Um Another great URL.
Doug Leeds:Yeah, another great URL. And that formed the strategy ultimately for IC publishing. But at the time, it was a great acquisition. I went to run it. That was fantastic because the CEO of Ask, I was running products, said he actually came to me and said, Do you want to be run biz biz for us? And I said, Absolutely not. I feel like I've been in the witness protection program for my legal career for like two years now, and no one knows here that I'm a lawyer, and the last thing I want to do is like a lawyer by another name, which is business development. And he's like, Well, how about this? Bias a company, and then you can be the CEO. Okay. That can be a child.
Cecilia Ziniti:That's lovely. I mean, it's also one of these things of it's like, like, how did you get to that point? Like, have you just done great work for him? Or like, what was the that that that's an incredible story?
Doug Leeds:Yeah, I had done good work, but that wasn't, I think, it. I think it was that he needed, he actually was a uh a CEO. He was brand new, and he didn't believe in product, and I was running product. Um, have a lot of disagreements with this person, but he didn't believe that product was right. He thought we had a marketing problem. I think that makes sense. So we wanted to pull, he said, look, everything you do, it's great. I can see it at Google, but it's not where we shouldn't be investing because they're getting all the credit for it. So we should put our money into marketing. And that means you don't have a job, but we want you here, so go buy something. That was sort of the story. It's fascinating.
Cecilia Ziniti:So, in that difference with Google, so I can a hundred percent, you know, empathize with this sort of like underdog type of scenario. And I think, you know, I was involved at Amazon when Amazon tried to do a f the a phone and it was sort of too late. But that innovation was was a great spirit. But in the case of Amazon, it was too late and they had this fundamental technology right around the iPhone and other things. Was it just that fundamental search algorithm? Like, and you and I can nerd out about search algorithms like crazy. You know, I remember at the time we had kind of Chi Lu and these like sort of early people, like algorithmic search was actually quite was the basically the AI of the of the era. But was that with Google, you said, okay, you got the CEO saying don't do product stuff, you know, let's just focus on marketing. Was the the the the technology difference kind of unovercomable? Or like well, like t tell us about that that piece.
Doug Leeds:That's exactly true. It was unovercomable. Um we unlike your experience, we started before Google did. So we were around first, but they got big really fast and really was a better product. The search product was better, and they got bigger, and they were investing billions where we were investing hundreds of millions. And it was, it's not that different from AI in the sense that it really was a capital-intensive business, and we didn't have the capital, even though we had a lot of capital, we didn't have the capital to compete with Google. Um, we had tried, we had bought a company that called Tayoma at the time that was doing its own search, and we thought that would be an improvement, but it really we just didn't have the firepower to compete with them. So ultimately, we joined them. I mean, when I took over as CEO, we were still trying to do this marketing thing, and we had spent a hundred million dollars literally on marketing, and we really hadn't moved the needle at all. And we weren't going to. So I pivoted the business um and basically did a deal with Google and said, okay, we'll use your technology.
Cecilia Ziniti:Oh. And so similar to what I guess Apple does today, right? Like Apple still has Google powering search on the although we were a search engine.
Doug Leeds:What Google has, I mean, Apple has a lot of things they do. They don't need to be a search engine too. We were a search engine using someone else's search engine. And it was a it was a legal reason why that worked. Because Google, it's so funny how it all comes around again. Google needed people needed another search player, pure search player, to show to the antitrust officials that they weren't a monopoly. So they had to show that there was another competitor out there that was doing well. And we were the perfect model for that because we didn't do anything other than search. So they really propped us up in a lot of ways.
Cecilia Ziniti:So that is fascinating for our listeners. So basically, this idea that Google, and they're seeing it today still. Yes, that Google has these antitrust problems and so is willing to go out and do business deals to actually prop up others. That is fascinating. And so how do you I mean, so so you kind of were like, all right, you know, it's cool. We have however many million users a month, let's go. Or like, what was the like how do you rally the team around something like that?
Doug Leeds:Gosh, it was great. It was that was easy because we became like super success. We had to scale down. We had unfortunately had to, you know, lay off the people in our tech who were doing the tech. Um, but we built a basically an arbitrage business, to be honest. I hated that word, but it was an arbitrage business. We would we would buy ads on Google and direct them to our search and then sell those customers the same ads that they would get on Google. It was really just buying over here and selling over there and moving the traffic, and we became incredibly good at that. Like we were spending a billion dollars a year on Google ads.
Cecilia Ziniti:Billion dollars a year.
Doug Leeds:It came to I think one in every 10 or 12 searches worldwide on Google had an ask ad on it.
Cecilia Ziniti:Um that's incredible. The scale of this, like, see, this is the thing, it's like these Silicon Valley themes. So that's actually a good segue, is like you've been across multiple eras of technology, the dot-com boom, the rise of mobile, now AI. You know, Google started at the time, obviously you're deeply familiar with them, having been a you know, apparently the world's largest consumer, or at least the world's largest buyer of Google's ads. Um What are the patterns that you see repeat across cycles? So, like, are there moments now, maybe the Google antitrust or others, where you're like, this is deja vu, I've seen this movie before.
Doug Leeds:Yeah, I think in in some ways, the the the question that I get a lot, and everyone does, is should we be excited or scared about AI? And that just feels to me like the same question. Should we be excited or scared about the internet? It just feels exactly the same. And then there's a big investment rush, and then there's probably a bubble that bursts, and then there's a few winners, and then people build an ecosystem around that, and then people learn how to run businesses, but also more value. Like if you look at the world today versus the world before the internet, everyone would say there's more value. Um doesn't mean there wasn't a lot of disruption, doesn't mean that jobs didn't change. I feel like that's the same. I know that there's going to be disruption, like crazy, and there already has been, but I'm hopeful that that we'll see that innovation wave result in a greater opportunity set for people who are interested in this. And I think that's very parallel to what we saw in Web 1.0.
Cecilia Ziniti:And, you know, I I see the parallel with internet very clearly. And obviously, you know, Yahoo is still around today, Google's still around today, WebVAN is not, but Instacart is. Is AI different? And I I guess I remember, I'm just remembering you and I were at Yahoo, Dan Rosensweig, who I think is also now a CEO in the space still, but he used to send the the quote the BlackBerry files. So he would send, like, I don't know, once a week or something, he would send an email to the whole company that he had typed on as Blackberry, and that was like novel at the time. So it's like funny now. And I remember at the time, you know, I was a paralegal, so I didn't qualify to get a Blackberry. It was like you had to be a director. And I was like, one day I will achieve this. But I guess um, you know, related to that story, like, is AI different? And maybe are you building something with AI? How do your students think about it? Like, you know, is it gonna be in two years we're gonna see the disruption that we saw in 10 in the internet? Any wisdom to share there?
Doug Leeds:I mean, I think all those things, yes, across the board, yes, to all those things. I think we will see the disruption faster. Yes, I am building something. Um, and I'll tell you about that in a second because I'm excited to tell you about it. And yes, my students are as a teacher, that's probably where the biggest disruption I think I'm seeing personally is right now. Because we're struggling with how do you teach with this tool that basically creates the output that we thought our students were creating? How do we engage their intellect when it's not through necessarily writing an essay, which they can have done for them instantly? So there's disruption everywhere. I'm seeing a lot of it in education. Um, and you know, it it's like anything. I'm sure when the calculator was invented, there was a bunch of disruption. Like, how do we teach math now that there's a calculator and and you adjust and you get okay, calculator can take care of certain tasks, use it as a tool, and then keep going. I think that's where AI will be in all things. Now, in a company, there's there's other issues. There's governance issues, there's data privacy issues, there's a whole bunch of things that have yet to be solved. And when you have a company and you have the customer's data, you have employees that are using AI with that customer data, even if it's not an officially sanctioned thing, like, oh, we have a tool for everyone to use. It's like my students. They're all using it because it helps them tremendously, but it opens up liability risks and holes in your all the plans that you've made have now a big gaping hole in them from AI. And it's look, you're the expert on this, not me.
Cecilia Ziniti:Yeah, no, I mean, I see it. I think it's it it's a challenge. I mean, the student thing is a great example because, you know, they they um there there's a book that says that like every human endeavor is basically sales and uh including teaching. And I think with teaching, it's like, okay, what you're selling is knowledge, the ability to learn, et cetera. And it's like, okay, they can get it now through AI. They can get the writing step. How do you engage them? And so, yeah, no, I I see that. I guess I wonder if there's anything. So we do see lots and lots of teams and kind of change management. And I think the teaching is actually a good mechanic, and that's been what we focused on in GCAI around getting teams to adopt. But I guess the question for you is like, you've done a whole lot of MA, whole lot of cultural transformation. Any kind of like, I mean, I don't want to say pithy tips, but any kind of like quick hits that you would advise that you would give to say GCs or CEOs who are trying to AI if I their orgs?
Doug Leeds:Well, I think it's it's the tips I would give are more generic in general than specifically for AI, but I think it applies to this, which is build psychological safety. Like you've got to really focus on a way to build a culture where people can feel comfortable sharing what's going on in their world. Because without that, you will have big problems. You'll have risks with people using AI in ways they shouldn't, but doing a bunch of things, not understanding the challenges that you have at your business. Um, and I think as leaders, that's I've taken the approach in my in my career to use silliness specifically for this and to like embrace being silly. I put my entire company paint paint a picture.
Cecilia Ziniti:Paint a picture. Like, you can use me.
Doug Leeds:My entire company at Ask slash IC publishing as we were transitioning uh through improv training. 2,000 people.
Cecilia Ziniti:So good. 2,000 people.
Doug Leeds:Yeah. And my my senior execs hated it at first. And then within a couple of weeks, they were like, oh my gosh, not only was I wrong about this impact at work, I'm using it at home, and it's changed my family life.
Cecilia Ziniti:And there's that giving the chills, Doug. That's amazing. That's lovely. No, I mean, I I I because I I do think the like yes and thing is important. Yes. But the level of commitment for 2,000 people to go through basically acting classes, like this is epic, like so good. And so, you know, there's somebody, let's say you had some executives that are like, no, I'm not into it. And then they're like, I'm talking to my kids better. It's amazing.
Doug Leeds:My spouse, yeah, exactly. And to be clear, it wasn't acting, it was yes and for sure, but not performance-based. It was about taking someone's idea and building on it and listening and empathetic listening and active listening and all those kind of skills and silliness and being able to fail in front of other people in a risk-free way allowed you to build trust so that you could talk about other things. And that's so good. Yeah, that was it was good. It was really fun. It typically means teaching, by the way. That's what I was gonna say.
Cecilia Ziniti:Yes, so that's actually the next the next thing. So today you're teaching leadership and persuasion at UC Berkeley Haas. First of all, do you teach silliness?
Doug Leeds:I do. So I have a class, I have two classes. One's called Leadership by Persuasion, the other one's called Creativity and Leadership. Creativity and Leadership is full-on embracing silliness. Like, absolutely. Played a game of yesterday was class. We played a game of like musical chairs, but but all changed so there'll be some leadership lessons in there. But the the whole course is structured around learning through playing games. That's the whole course.
Cecilia Ziniti:So, how I guess um, what are the students like, what's your ideal outcome when a student takes your class? And by the end, they've they've played the games, et cetera. So that they're gonna go into their job. Maybe it's similar to, you know, the IAC of however many years ago, where you're sort of doing this very technical SEO advise, very math-based, you know, dashboards, all these things. When they leave your class, how are they like like literally be just be very concrete? Like, how are they gonna be better in their jobs or what what what ideally happens?
Doug Leeds:So the definition of leadership I use in the class is the ability to get other people to do what you want them to do as if it's their own idea with with interest and desire of their own, right? So how do you motivate people? How do you how do you persuade people? How do you lead people into doing what you want so that it's their interest in doing it and they want to do it? Go through a series of games, but we also do a social action project where the students go out into the community and try to make some change happen and then learn from those experiences to get to a sense of, okay, how do I put all these pieces together? How do I listen to somebody? How do I make them feel heard? How do I understand why the thing I want them to do isn't already happening? That's a big part of it. Why I I coined a term for it called WHAPODI, which I teach, which is why aren't people already doing it? It's an acronym, Wapati.
Cecilia Ziniti:I I love that. I you know what's so funny is is as a leader now for me coming into being a CEO, that question of like, I thought this was happening, like what is going on? Like this is sort of like, why aren't people already doing it? Yes, exactly. So I I'm I'm I'm gonna be an evangelist for your term. So okay, so you teach them that, and then they get to they get to the this leadership of like getting people to do things as was our idea, that's bringing to mind for me. So a lot of our listeners, you know, are focused on the legal field. Maybe they manage compliance, security, HR, these kinds of functions. And I used to train when I train more junior compliance folks, it was like, again, compliance is sales because you're getting people to do things maybe they don't really want to do, right? And maybe the law in some cases may not make a ton of sense. So you've got this like parallel thing where you're trying to persuade regulators or make some change there while simultaneously being like, yep, I know this seems a little strange. We got to do it. Like, here's how we're gonna motivate. And so how did you apply it in these sort of more, more, I guess, more or more like in that context? Like, like, how would you we make it specific to legal?
Doug Leeds:Well, I mean, I think this is where it came from in some ways. Like as a lawyer, especially an in-house lawyer, which I know more about. So I shouldn't say especially, I just know more about that as an in-house lawyer. You have a lot of authority with respect to like what the legal rules are and what the requirements are, but not a lot of authority to make somebody do something, right? That comes maybe up through the GC, if you're the GC, then up to the CEO and back down. But you're not gonna go into a meeting if you're like a mid-level lawyer and say you have to do this and expect people are gonna do it if they don't want to do it. It's gonna get escalated, there's gonna be a fight, all that kind of stuff. So the enjoyment that I had out of being a lawyer was working with teams to figure out a way to get them to do what I needed them to do as if it was their idea. How do we find a way to say yes instead of saying no? And one of the big problems with lawyers is they're looked at the place as that's where you go to get a no instead of, okay, this is how you solve a problem. We do have a problem here, but there's a way to get to yes, not trying to steal the name of that book, but there's a way to get to yes. Uh yeah, that's right.
Cecilia Ziniti:And I mean, we talk about this a lot with with other guests of like this, you know, there's some people are like, you know, there were there was a meme that did very well. And I'll I'll tag him in the show notes that was like, change legal from the department of no to the department of I told you so. And it's like, oh God, no, don't do that. But it was kind of like it was like this department of no, like KNOW is another one that, you know, a friend at Out of Canada uses. But this idea of that, you know, we're not trying, like, I don't get this satisfaction out of like, no, no, no, no, the statute says this. It's more like, how do you make it a we thing? We're like, okay, we're gonna launch Alexa. Like the example I always use is Alexa, where I was product counsel on there, and you tell, you know, most privacy attorneys at the time, like, hey, we're gonna launch, you know, effectively a hot mic in your house. And they'd be like, what the what? You know, it would just not be a thing that they would be on board for. But, you know, I had another, another guest, Tina Patel, who she and I worked on that project together. And it was like, you know what? No, we looked at all 50 states worth of wiretap laws. We made these beautiful charts and things. And then ultimately, what was really beautiful was the product teams did exactly what you described because it was like, okay, there was a realization that this new technology, people need to be comfortable with it. They did the ring light, they did where you could delete your utterances, you could um, you know, have a lot of control. And it ultimately was that customer-friendly thing. So for me, like actually practicing in privacy was one of my favorite areas to practice because it did have that kind of like reasonable person, very almost like user experience type bent to it. Yeah. Which is I I guess what you're what you're describing too, of like, okay, what is the business angle that we can reach? Or in this case, your antitrust thing, like that's amazing. Like, you can imagine at Google somebody being like, okay, how can we like fix our position here? Well, let's do some interesting BD with IEC. So you can see the other side of the table there too.
Doug Leeds:Pitch them on that. But the ring light, the ring light, I love this because that is an example of a I don't know who came up with the ring light idea and where it was, but it solves a big problem, right? Which is the idea that you know something is there, that the mic is being used in some way. Right. And so interesting, like just in conversations with you right now, thinking really what I think lawyers could do more of is be legal product managers. Yes. And really thinking about, okay, instead of saying no, what is the use case? And then how do I build a product into the product we already have that accomplishes the legal, you know, risk avoidance, but also the job of what the product is there to do. And that's we call that a lawyer, but it's really a product manager if you think about it like as solving the problem instead of just identifying it and saying no.
Cecilia Ziniti:Yes, a thousand percent. And I mean, for me, I self-identified in that, and it's been a big kind of boon to my career. We have a lot of folks, you know, who have this product council title. And I think, you know, we had an episode a few weeks ago with David from Sneak, and I relayed the story that I supported the product team at Amazon, and then they had an off-site where they did, you know, what is it, like the fake skydiving where you're like on top of a fan or whatever. And I got invited with the product management team. And it was like one of these I remember it my whole career. It's like this pinnacle moment. So, you know, Charlie Kindle, if you're listening, that's thank you for the invite. Because I still remember 15 years ago or however many years ago doing that. So legal product legal product manager. I mean, this is interesting because we are seeing now, particularly with AI, that legal is in a great position to actually drive AI because of some of the Data issues, privacy, confidentiality, all these things. So I I think we're gonna I'm gonna have a challenge. So if you're listening and you have the title legal product manager, reach out and we will have you on the show and we will we will hat tip Doug for for coming up with it. I love it. Awesome. I love it. Um you're founding a nonprofit. Yes. Or co-founding nonprofit. So what is it? Tell us about the vision. Um and how does it how does it relate to what we've talked about today?
Doug Leeds:So the it's called RSL, which stands for really simple licensing. And it is two things. It is an open web standard that anyone can use to articulate their rights for the content that they're publishing or creating with respect to AI. So coming from search, we use the robot.txt file as a way to describe in machine readable terms what search engines could do with the content that we published. And that created an ecosystem, which is okay, you can take my content, you can crawl it as long as you index it and then give me traffic. That's the ecosystem. You can have the content to index it and you send me traffic, which I monetize. But that is blown up by AI because they take the content and they don't give the traffic back because they're giving you an answer without a link or a link you would need to use because the answer is all right there. So they're doing this, obviously, this is well known at huge scale, internet scale, millions of sites, they're taking the content. The web standard would allow anyone to say, here's what in the robots.txt or or attached to any piece of content or into your HTTP, this is what the rules are for using my content. On top of that, we're building a collective rights organization. So think of like ASCAP for music, but this is for all the content on the internet, basically to come together and collectively represent those rights with the AI companies. So you can all say, oh, you can get all the content across the entire internet in one contract. So it's super efficient. It creates a new product that didn't exist before that helps both AI companies and content creators and publishers get paid for their work. So that's what we're launching. By the time this podcast is out, it'll have launched with support from Reddit and Yahoo and People Inc and Internet Brands and Ziff Davis and Medium and lots of companies.
Cecilia Ziniti:I can't think of a better person to do it. Because if you're thinking, you know, that you at IAC, you were buying one in 12 ads on Google. Like the thing that I think people don't realize is like the scale of the really micro payments that happen on Google. Like so I remember when I was at Yahoo and we had a I think a patent case or something, and the question was, what is the scale? And basically figured out if you consider every single click, so every time you click on a sponsored link, that is a few cents or up to hundreds of dollars that are getting charged and tracked, and you know, m Google's massive ad systems and build and so on, the number of transactions is actually greater by I think an order of magnitude of what Visa and MasterCard process everything. Yeah. So thinking about the scale of this and for AI, like this is actually a reaction that I had. So I did some speaking on the New York Times versus OpenAI case. And then this week I spoke with the press about the anthropic settlement. And basically, my conclusion was your company was this idea that there is a commercial solution here. And funny you mention ASCAP because it's very sophisticated. And you know, there's a very clear music licensing framework, very simple. So I think doing it for the internet, if you think about authors and the ability to publish, including on IAC or anywhere. Like I always tell people, people ask me, like, how is AI trained? And I'm like, well, have you ever posted something at Craigslist? Have you ever made a comment on Meta? Congratulations, you've trained in AI. Like, exactly.
Doug Leeds:That's exactly right. Then for, and let's take Reddit, for example, because they're a sponsor. Like 40% I've seen of AI training is happening on Reddit. Reddit has deals with some, but not, for example, Anthropic, who they're suing right now, who's just taking their content. And that's just it's two things. One, it's probably illegal, and we'll have the lawsuits to settle that. But two, it doesn't allow for that content to be created, to be rewarded. So the ecosystem breaks, and ultimately that hurts the AI companies too, because they need this content to continue to be created. So actually, like Sam Altman has said, we need a system, we need a protocol that allows for this to work. Great. That's what we're doing.
Cecilia Ziniti:Getting people, I love this. I think this is an example of you're getting people to think stuff is their idea. But no, this is so good. Because I think like uh OpenAI has done a good job of this in terms on the public policy side of like, hey, regulate us. Like we want to be regulated. And this is fascinating. I I'm gonna talk with someone from Cruz on the autonomous vehicle side where we're similar, where it's like, hey, no, we actually do want rules in this scenario. I love it. I can't wait to I can't wait to use this and and to like, you know, to go through the the legal terms, which I know are gonna be amazing, and see the systems. I mean, I've written legal nerd, um, which is like a lot of a lot of our listeners. So, all right, so let's go to quick takes. So, what is a book, podcast, or idea that has influenced your thinking?
Doug Leeds:So this is an idea. There's something called the three H's. I don't know if you've heard of it, but the three H's are when someone's talking to you, they're talking to you for one of three reasons, or maybe more than one, but one primary reason. It's either to be uh heard, to be helped, or to be hugged. And if you get that wrong, you're really missing the the interaction and the value in the interaction. And I get that wrong all the time. So like I hear everything as I'm asking for help. And so, like, someone talks to me and I immediately go into, okay, let's to break down. How do we fix the problem? How do we solve it? When oftentimes they just really just want to be heard, they just want to be acknowledged for what they're saying, for their ideas, for their pain, for their stress. Or sometimes they just want some sympathy, some hugging. And while this works absolutely in the family dynamic, it absolutely works also in work. Your employees, your colleagues, there are times when they're not asking you for your help. They just want to be acknowledged and heard. And I don't know, that's something that's been really helpful for me to think through. Um, yeah, about how to.
Cecilia Ziniti:Yeah, I love that. It actually is funny, so I Google it to for my own to to bookmark something later. And it says apply the three H's and unboss a little, which I think that's probably helpful. This like sauce, you know. Because then I think there's like this boss lady thing that, you know, at least that I'm trying to figure out my own, you know, leadership style as a CEO, and it's that's very helpful. Amazing. Um, let's see. So any other advice for somebody? So let's rewind the clock. We're we're, you know, let's see, late 90s, I guess, and you're starting your career. What advice would you give yourself?
Doug Leeds:Okay, so I think my career was definitely accelerated from taking the advice of of Alexander Hamilton and be it from the musical, be in the room where it happens. That's my advice. He got so much exposure to some of the business issues that were happening, for example, at Overture at go to.com, and was able to start building stuff there because none of the lawyers knew how to use PowerPoint. So love that.
Cecilia Ziniti:I love that. So good. I had funny enough, I had a English teacher, Mr. Seites, rest in peace, who had us do our final project in PowerPoint, which at the time was new. So I don't remember much about Chaucer, but I was like, when I got to Yahoo, I was like weirdly good at PowerPoint, and it was like a crazy career accelerant. And that was like the new thing of the day. So it really was so I think I would tell people like, learn AI. Like we actually hired junior people. I've got an associate chief of staff, we've got an AI ops engineer, and and they are fresh grads who were really into AI. And so, yeah, love, like pick that moment. This has been fantastic, Doug. Where can folks listen or listeners connect with you, find out about RSL, find out about your class?
Doug Leeds:So RSLcollective.org is uh the website that we have for the collective. And I encourage you to everyone to go check it out, especially if they're creators or publishers, because we'd love to have you join us. It's free to join, and we'll give you money. That's that's the pitch. Um Amazing. And yeah. And my class, if you're if you want one of two things. If you're a student at Berkeley, I mean it's an undergraduate class, uh, check out Creativity and Leadership or Leadership by Persuasion. And if you want to maybe speak at leadership by persuasion, hit me up at you know, my so good.
Cecilia Ziniti:No, we have I I mean, I'm thinking of like Ruby Zeffo at Uber also uses kind of humor and kind of lightheartedness to be incredibly effective. Other folks, I'm thinking, I mean, I I think like I love to come to your class. Like, I love this stuff. I would love to have you. Yeah, reach out to Doug.
Doug Leeds:We're gonna have you come back. Amazing, so good. That would be great.
Cecilia Ziniti:Super fun. This, Doug, thank you so much for joining us today.
Doug Leeds:Thank you so much. This is wonderful to catch up and to talk with you. Congrats on all your own.
Cecilia Ziniti:Thanks again. That was my conversation with Doug Leeds. His journey shows how leaders can evolve across industries, hype cycles, technologies, while staying grounded in resilience, persuasion, and I guess silliness. Super exciting. If you're thinking about how to lead through change, whether in tech, business, or law, I hope this episode gave you perspective on how to turn disruption into opportunity. Follow CZ and Friends wherever you get your podcasts, and subscribe to our newsletter at gc.ai slash newsletter for behind the scenes insights and actionable tips for legal leaders. Thanks for listening, and we'll see you next time.