Intro Music 

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Tyler Finn 

How do you make the transition from IP lawyer to general counsel in a typical path? Help Adobe navigate a transition to the cloud and then the AI era and Make time for your family through all the ups and downs Today we are joined on the abstract by Dana Rau who recently retired after almost 13 years at Adobe including about six or seven as general counsel. Before becoming their GC, Dana led Adobe's intellectual property and litigation teams. Earlier in his career,

he led IP for the entertainment and devices, like Xbox, cool things like that division, as well as company-wide patent acquisition for Microsoft. He started his corporate career at Fenwick and West, and he almost had like a couple of careers even before that, before law school. 

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Dana Rao 

It was a journey. 

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Tyler Finn

We're going to talk about it. Dana spent time in Washington, D.C. at the Department of Justice working on Native American affairs under Attorney General Janet Reno, after working on the Clinton campaign, and he actually worked as an engineer earlier in his career as well. He did his undergraduate studies in electrical engineering. So there's a through line from I guess the beginning to the IP. 

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Dana Rao 

In retrospect. 

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Tyler Finn

Don't let me don't let me draw conclusions.

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Dana Rao 

When you're living it forward, there was not a through line. But backward, it's all clear. It all worked out.

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Tyler Finn

Dana, thanks so much for joining me today for this episode. Okay, you retired recently. That's exciting. What have you been up to?

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Dana Rao

Then up to a lot and nothing at all. I would say the first two months I Slept, you know trying to recuperate all that Energy, it was funny. I had a checkup a couple weeks ago with the doctor well, and I hadn't seen a doctor or dentist in years and And he was like he was just doing a regular sleep apnea check. I don't have it Uh-huh, but he was just asking about it and it turns out everyone has sleep apnea now This is what he was telling me. He's like… 

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Tyler Finn

My father recently got diagnosed with sleep apnea…

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Dana Rao 

I was like maybe we were we went away with a couple of couples to New York two weeks ago and everybody else It's so it's a whole thing. I didn't know I never heard of it and And he's asked me he's like well, do you do you take naps? I'm like, for the last two months, I've been taking naps. A lot of naps. I don't think it's sleep apnea. But prior to that, I've never taken a nap. So, so it's quite funny. So the rest was really important. I didn't really realize, you know, how much, you know, 30 year career and pretty breakneck pace throughout the whole thing, how much that took out of you. So that was that's been great. It's also been really fun to connect with family and friends and college and high school friends that I just haven't seen and haven't had the time to devote to. And that's been amazing. It's been awesome to connect with my adult daughters who are both entering the workforce as of last May with actual jobs. And I get to enjoy watching their corporate political struggles and occasionally offering advice, but mostly offering jokes. And that's been amazing. And and then I've been writing. So before I went to law school, if someone ever asked me the question, what would you do if you weren't a lawyer? It was always I wanted to write because I loved writing. I just used to write creative fiction. I wrote a novel, which I didn't end up publishing because I was I wrote the novel, sent it out to a bunch of people, got a bunch of feedback, and chose not to implement it because I was about to start my career at Fennel McGill West and I'm like, I don't have time for this. And my novel was perfect anyway, so why would I do feedback? So I didn't get published, I wrote a screenplay. So I had stuff, I had stories I wanted to tell. And so when I retired, I told my wife, I'm like, look, it's probably the time for me to, before I think about if I want to do anything next, to really make sure that I can actually live out this dream. So I'm 178 pages into it.

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Tyler Finn

Amazing. It’s a novel?

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Dana Rao Tyler Finn

It's a science fiction novel. Yep. 

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Tyler Finn

Cool. 

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Dana Rao Tyler Finn

Yep. I'm leveraging all of my law, technology, and policy experiences into this book. And it's been fun. It's been challenging. It takes like three hours a day. I just dedicate to writing. And then I spend the rest of the day doing coffees and 

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Tyler Finn

Stuff like that. 

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Dana Rao

Cocktail hours. Yeah. Podcasts and things like this.

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Tyler Finn

So do you like to write in the morning? Like, are you like, I wake up early. I start. What's your, what's that routine?

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Dana Rao

I've always been most creative in the morning. So even at work when I would, you know, write speeches or do presentations, it's always, you know, 730 to 830 in the morning when it would be the, like the block of time where I kind of wake up, feel fresh and just write. So even now it's, you know, I'm, I wake up around 6.30 or so and start at 7.30 and just write until 10.30 and then either go exercise or cook, or like I said, go see people and kind of refresh. I was in Florida, I mentioned, and we went to the Hemingway house, and it's where he wrote, where Ernest Hemingway wrote like 75% of his books in Key West. And so he had a little writer's nook in his house and Jason too had a little writer's nook and so they told us his schedule was he got up at 6 in the morning, wrote till 12, swam in the ocean till 2, ate lunch or dinner or whatever, and then went to the bar and got blind drunk every night. So I don't have that piece of him working into my schedule, but I took notes that he did have that morning dedication to writing and then he didn't work at all afterwards, sort of kind of recharged the batteries, so that's been my model. 

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Tyler Finn

The doctor you just saw is probably pleased that you're not indulging in rum every single night.

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Dana Rao

He's asked me several times how much I'm drinking. So I think maybe he's worried. Okay, what's the screenplay?

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Tyler Finn

What was the screenplay about? I'm curious about that too. And then we'll get into the career.

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Dana Rao

I remember this was probably 1991. 

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Tyler Finn

Okay. 

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Dana Rao 

Yeah, maybe 90. And so it was, it was funny in retrospect. It was funny, a story about a boy and a girl and the boy gets, they break up, you know, acrimonious breakup, his fault. And she works for the Social Security Administration. And at that time, so it was set into the future, near future. And at the time, there's database, you have a social security number that ties into all your bank accounts and all your digital transactions and everything. She deletes them. So the screenplay was called Deleted. And so she deletes them. And so then the rest of it is just sort of like he has to suddenly adjust to this fact where he has no actual identity in the world because his whole identity was a bit, it's a digital identity as way you go about doing your life. And so he has to go on that journey and all the problems and then eventually overcome his emotional problems too and get back together.

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Tyler Finn

Life may be imitating or may be close to imitating unpublished art.

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Dana Rao

It was, I mean, again, back then I was in LA at the time and so like everybody was shopping it. So I did, I knew some people, I took the script to people and so I did try, but then I left to go to DC. And one of the things you learn about screenwriting or any kind of writing is, you know,

obviously you have to be able to write, but even more important is you have to be able to market and shop. 

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Tyler Finn

Right. 

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Dana Rao

And so writing the screenplay was great, but you really just needed to be in LA and hand it over to people and follow up and knock on doors. And I left LA to go work in DC. And again, that was the end of that because unless you were there, it's trying to shop it. But I look back on that and I'm like, I don't know how the writing is. I still have a copy of the script. But I like the idea. In 1991, that wasn't a bad premise.

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Tyler Finn

That's great. So the new book, are you thinking that you want to see it all the way through and get it published? Or is it more of a personal project for you?

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Dana Rao

I think for me, the way you write, and again, this is the same thing for people who are doing anything in corporate or personal, I think it's the same, is you write for yourself. Like it has to be something that you want. You mentioned right before we got on that you wrote a post that I wrote about John Warnock. Like whenever I write anything, it's always like, this is about me first. And then after it's done, we will look at it and decide, does anyone else want to read this? Right. Yeah, but first it has to be, so that's where I'm at. I'm writing a book that I want to read.

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Tyler Finn

Yes. 

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Dana Rao 

And when we're done, I'll show it to my wife and select other people and if people are like This is the stupidest thing I've ever read and yeah, I'm worrying and I don't like it You know, then maybe it'll be a personal project. 

Tyler Finn

Yeah You don't need me to agree, but I totally agree I all the time, right? Might my rule with these podcast episodes or with the webinars that we host or like the marketing content that we put out, I don't want to contribute to it if it's not something that I would actually want to read and consume and think is really interesting and engaging, right? Like that should be the bar. SEO should not be the bar. 

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Dana Rao

And it shows up, you can see there's a lot of generic content out there and that's typically as people are trying to triangulate. Yes. Again, I work for Bill Clinton, as you mentioned, and he invented triangulation as politics. That's probably been good and bad.

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Tyler Finn

Right.

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Dana Rao 

You definitely see it even in politics with politicians like the ones that are speaking about something they care about really resonate even if you don't agree with their position. You still tend to like them because you're like they believe in it. 

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Tyler Finn

Yeah.

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Dana Rao 

And understand it. And when the politician is merely saying something that you think they think is what I want, then you're immediately become a little skeptical about the cynicism involved in that and you don't love them. So I think it's true in everything that the more authentic you are, the better chance you're going to have to connect with people. 

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Tyler Finn

Authenticity is only going to become more important in the future. And we'll talk a little bit about that and the work that you've done. I'm always starting at the counter-authenticity in this. Okay, well before we get there, okay, so you started your career as an engineer and then you spent some time in DC. Maybe take us through that time a little bit and how that ultimately led you to law school. DC to law school was obvious, but electrical engineering to law school maybe a little bit less so.

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Dana Rao

Yeah, I'm glad it's obvious. So I, uh, my dad was the chairman of electrical engineering at Villanova University.

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Tyler Finn

Oh, interesting.

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Dana Rao 

So, um, he told my brother and I that we were going to be electrical engineers. Had that going for us. And, uh, I always tested, um, a little better in English than math, but, you know, okay. And both, but so if you, that you had to ask me what was easier, it was easier than, than math, but I liked math. I was intellectually curious. I like science. So it was fine. I'm like, you want me to do it? He's like, I want you to have a job after you graduate. And he also Villanova was free. So he's like, you're going to Villanova. Like, I get it. I mean, I was 17. So I wasn't that excited. But I, you know, because it's so close to home. Yeah, I want to be anywhere near home. But nonetheless… 

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Tyler Finn

Running to dad around campus. 

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Dana Rao 

I did have a digress. I did have a my second year I was taking integrated circuits and I'm old so the audience may not remember this but back then you would have overhead projectors. You had these transparencies and you shine the light, right? So you go eight o'clock in the morning, you're taking integrated circuits, they put the transparency down and he shows the notes. He hands out a packet of the notes of the day's material to you as you walk in. He turns out the lights. So this is a recipe for disaster for 18 year old boys or 19 year old boys. So I fell asleep a lot in class. And I'm like, why? I have the notes. I'm tired. So he complained to my dad about it. And he's like, your son's always falling asleep. My dad told me he's like, your son's always falling asleep in their class. And you talk to him. And my dad looked at him and said, you need to make your class more interesting. That's amazing. Yeah. So he, uh, but we did have an agreement that I would never take his class.

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Tyler Finn

Uh huh.

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Dana Rao 

Because that'd be too, that'd be too weird. Yeah. Um, and, uh, so, so it was great to have that. So, I enjoyed learning about things. Again, my grades were, were mediocre in the engineering classes and excellent in the English classes. Um, but I still liked it and I got a job at GE Astrospace afterwards as a RF engineer, a satellite engineer, designing a ground terminal to talk to a military satellite in the space, which is great and it's fun. I love the engineering culture. I love the engineers. It was hard, again, the math was hard. I remember one time I was in a four-person cubicle just trying to do an algorithm and just trying to encourage myself and saying my data you can do this. It's not rocket science. And then I can wait a minute. It is literally rocket science. And so so I enjoy the people and the culture and the work was fine. But it was clear after a year, the way they talked to me was the path for promotion was really to be a project manager, program manager, management. And then I was had the reflection, well, if I'm not I'm not doing the engineering anyway, then what am I doing here, right?

What does it make sense? So then I was also tired of living in the Philadelphia area, so I quit my job, moved to LA with our college roommate. The intention was to get my master's, get residency, obviously, it's because tuition is much cheaper, and get my master's. But I volunteered in the Clinton Gore campaign just because I wanted to do something. I have no experience in politics. I just kind of showed up every day, did stuff, whatever they wanted me to do. And I became friends with the person who is the director of women's issues state of California. 

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Tyler Finn

Cool. 

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Dana Rao

And she asked me to be her deputy director. So I became her deputy director and learned and spoke a lot about women's issues, state of California, which is a super fun and interesting career change.

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Tyler Finn

Yeah. 

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Dana Rao

And I really enjoyed it. I didn't obviously won. I worked on the presidential inaugural campaign event in D.C. So I went to D.C. just for two months, came back, worked on the L.A. mayor's race. I was fully committed to political life at that point. Mayor's race, lost the mayor's race. I thought it was like to lose one of those. Then kind of had this fork in the road of do I want to stay in campaigning? Do I want to just work in politics? What do I do? And one of the person who ran California for Clinton moved into the White House and he sent me a letter saying, come to DC, I'll get you a job. So I moved to DC, he did not get me a job. And this is probably my career low, I always emphasize this a little bit because everyone goes through these downs. It was a career low, it was six months of being sleeping on people's couches, I didn't have any money at this point, sleeping on people's couches, eating McDonald's, having no future, not understanding what was going to happen. It's very stressful. And I eventually, a woman who worked in the Clinton campaign with me in LA got a job at Justice. She was a deputy director. And so she took pity on me and hired me as a special assistant to the counsel to the attorney general. So she worked for the counsel to the attorney general. That was a man named Gerald Torres, one of the Attorney General. That was a man named Gerald Torres, one of the most famous legal scholars in America, even today. I think he's teaching at Yale right now. And then Attorney General Reno asked him to work on environmental justice issues and Native American issues. My boss took, my direct boss, took the environmental justice issues. And so I have that Native American portfolio, of which, again, I knew absolutely nothing. And so my actual task was to plan a conference to bring the Attorney General into contact with the 535 federally recognized tribes of chiefs. And so I planned this conference in Albuquerque, New Mexico. I think it's the first time the Attorney General of the United States actually met the tribe of chiefs, even though the Department of Justice has civil and criminal jurisdiction over the tribe. So we have so much power over the tribes, but it's always been an adversarial relationship. And Torino, Reno, grew up in Florida and was close to the Seminole tribe. And so she came in with this idea of kind of repairing relationships between the United States and the tribes. So we had this listening conference, it was what it was called, and it was amazing. And all the tribes got up and spoke and spoke for peace. And afterwards, they sent in a lot of requests to us. And they all piled up in boxes. I no longer had a mission because my mission was planning that conference. And so I started reading all the correspondence. This is something I say to young people everywhere. I didn't really have a clear job at that point. I mean, I was hired, I was getting signed, but it wasn't clear. And I just took it upon myself to be like, okay, no one is looking at this stuff,

I'm gonna look at it. And so oddly, after reading all that stuff, I became the person at the Department of Justice who knew the most about what the tribes wanted. Yeah. Because that wasn't really their role. Everyone else's, it was an adversarial relationship. And so I was reading it. So then Attorney General Reno wouldn't want the tribes perspectives on issues.

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Tyler Finn

Right.

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Dana Rao

I was the person that ended up talking to her about it. So I ended up having this really cool relationship with me and the counsel, Gerald, the council, and Janet Reno meeting often to talk about issues from the state's perspective and the tribe's perspectives. That never would have been possible had I not just said, hey, I'm just going to read all this stuff and become an expert and do this on my own and take that initiative. Once you become the expert, doors open.

People all of a sudden want that expertise. They want to know the person who actually knows what's going on and it was great and she was Reno was. Probably my first, maybe my only. Hero in that sense, because she's just if you ever had a chance to meet her, she's super imposing. She was like 64 and thick glasses and probably the smartest person ever met. She was one of the people where you could spend like a week. Understanding an issue and you walk in and she asks you like two questions and they'd be things you'd never thought of and it's just such a shock to me. I'm like, wait, how could I have not thought this? It's so sharp and funny. She didn't laugh a lot but I would always make jokes. Like no one else would even try to make jokes to her. I would always make jokes. We were standing in the elevator, I'd scratch her hoax and she'd kind of stare at me. But I got this beautiful letter which I still kept in every office I've ever been in, which I hung from her. And the last line is her appreciating my sense of humor. So I know in retrospect that…

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Tyler Finn

She was laughing at me inside. 

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Dana Rao

But the one thing she said to me, which sort of changed my life, was we had this issue with I think it was the state of Arizona and one of the tribes in Arizona, Navajo, maybe about water rights. And so she's like, what do you what do you want to what do you think you should do? And she asked me and I'm thinking about politically and I'm thinking well for President Clinton's campaign you know in Arizona and here's how I think I would come out on it that's what I told her and she just looked at me with those you know glasses and just said you know Dana what is the right thing to do? And no one had ever asked me that question before in anywhere in my career like it's the first time like a like it was like an analytical framework that just got shifted in my head and there was another way to look at these things that's sort of this greater good and good for the world and good for the country like that was a factor to be considered and and reno is the only person who thought about that she wasn't asking about reelection you know probably to her detriment to the extent she cared about her own career sure but that's not how she was wired right and so i answer when you know i in that moment i reflected on the question of that. Well, really, in the right of it, I think the tribes are right. And so it's like, all right, well, that's what we're going to do. And and I learned a lot from that moment. And so the rest of my career, I've always had that question, whether I work for a company, even even a law firm, but even at a company, you could ask, you know, what's the right thing to do for Microsoft? Not like what the right thing to do is for the issue that I'm trying to struggle with. Fifteen other lawyers or five business people who all have their own agendas and their career goals. Yeah. I'd always elevate the question to like, what is the right thing to do for Microsoft? I felt like if I was doing that or Adobe, then at the end of the day, I was going to be supportive, right? If it got escalated. And then when I had a more of a position of power at Adobe, I could actually ask the other question of what is the right thing to do for the world, right? In addition to what is the right thing for the company and we can take multiple paths and is there a way to account for like the greater good in the way we're doing while still being true to our shareholders, right? And so it really did change, I would say, my entire career for the better and it gave me a lot of freedom, I think, to do the right thing, which is not only, I would say, empowering, but certainly has made my work and life more interesting and exciting and rewarding because I've had the ability to make that choice.

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Tyler Finn

Can you think of a time that you can talk about? I always offer that caveat where you, But the bigger version of that question, what is the right thing to do to someone in your organization and got an answer that changed the direction that the company was going to take or led you and maybe other executives to conclude that we could do something that might be a little bit more right for the world in this case than what we were going to do before?

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Dana Rao

I mean, there's a... So as General Counsel, you get questions like that, you know, pretty often. 

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Tyler Finn

Sure. 

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Dana Rao

So, you know, I would say that that's not unique. I think the good question, a good way to answer this question or a good example of this is in AI. So when we were building, was building our our general AI model W Firefly which creates text to image text to video. We were thinking about how to train it on data and so you know the answer for what everyone else was doing was scrape the web. 

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Tyler Finn

Yep. 

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Dana Rao

Right and if you're going to create a creative model you're scraping the web of you know videos and art and images that that artist made. Right. And then the tool you're making is going to be used by artists, but could also be used to displace artists. Right. And so you have to. We ask the question and we may ask the question. And I've always been a business person, obviously. Sure. In addition, being a lawyer and whatever. So you have to ask the question, you know, what is the right thing to do for the world and then for Adobe and then for our customers? And if you can get an answer that hits all three, then that's the best case scenario. And in this case, we felt like after sitting down with the engineering team, we can make a model that was what we refer to as commercially safe. And so what we did was we had this portfolio of stock images called Adobe Stock and the question to the engineering team was, can you build a competitive model just on that?

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Tyler Finn

Interesting.

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Dana Rao

Without scraping. Because if you can, then we're going to be able to go to the artists and the creative community and say, look, this model is here to help you and it's not trading off of you. And that makes a lot of sense for Adobe because creators are our customers and enterprise customers are our customers. And the other piece with my IP hat on was, I could see years of litigation coming, right? Over these copyright questions. And I think that United States probably fair use may be the right answer technically, if you truly understand how AI models work. I think fair use may be the right answer, but it's years, gonna be years of litigation before it gets to the Supreme Court, certainly gonna go to the Supreme Court given the billions of dollars at stake. So that's a lot of anxiety for enterprise customers who are thinking about deploying this technology in their systems and saying, oh my gosh, you could get ripped out if I get a preliminary injunction or whatever it is, right? So this is good for the world because AI being trained maybe the right way without being copied off of people's work to displace them. It's good for Adobe because of our creative customers and it's good marketing for them. And then it helps us avoid liability, right? Yes. Avoid that uncertainty, so it helps us with the enterprise customers.

So that was like the way I triangulated all three and that's what we ended up doing. And we were the first company to even attempt to do that. And even today, there were still, we just launched, Adobe just launched this video model. It'll be fine. And also the same thing trained off of licensed content. So in that commercially safe way. So I'm excited that we were able to find a way to do things, you know, the right way, but still be true to our shareholders and develop our best in class technology. Because if you don't deliver best in class technology, right, Adobe doesn't make any money. And then we go out of business and that doesn't help anybody. So that's why I'm saying you're a business person in addition to being kind of an FSS. And it's what I love about being in the private sector because you have this competing concern.

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It's more complicated. It's more nuanced. I've never loved academics, as you can tell by my spotty grades throughout school, because I feel like they always, they kind of sit in an ivory tower and they just kind of make pronouncements and it's easy to say because you know they're getting federal funding which may not be as attractive as it used to be.

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Tyler Finn

Yeah, unfortunate I think.

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Dana Rao

Now they're seeing some of the compromises right. But it's easy to say from there but when you're in the business to make money and give people jobs and create careers and have impact and do the right thing it's a much more interesting, complicated, sophisticated question you're trying to answer. 

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Tyler Finn

Well, sure. And I think to that point, the most sophisticated execs and GCs who have to be business people are by necessity having to do this. But a really good CRO is also doing this. You have to see the whole picture, right? Like a really good CRO isn't going to be thinking to themselves, how can I most likely, how can I juice revenue just for the next two years and then I'll leave the company in shambles by right like telling the GC you have to take on you have to see the whole picture. How did you get started on this journey? Because you spend time in DC. There's a well-worn path of your sort of a political appointee in DC. You go to law school and you go back to DC. You get another political appointment. I mean, I'm sure well, I suppose administration's change and that sort of thing, right? But there were opportunities to...

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Dana Rao

Again, it's, you know, you have to think about my background. 

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Tyler Finn

Yeah. 

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Dana Rao

When you say well-worn path, like my dad immigrated from India in 64, you know, you grew up in a village that didn't have running water or electricity and, you know, so like, I didn't have any of these paths, like I didn't know any of this stuff. So as a Department of Justice, I'm just looking around and I'm saying, well, everyone here has got a law degree, you know, maybe I need to go get a law degree. And I was also ready, I was ready, emotionally ready to move on. So the most exciting thing about law school, so I decided to go to GW, was, you know, you have 400 people in the class, and then you have 100 in your section, right, you divide it up into four, and there's 13 people in your research and writing section.

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Tyler Finn

Okay.

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Dana Rao

And the first day of law school, I met my wife-to-be in that 13-person class. 

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Tyler Finn

That's great.

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Dana Rao

We have different versions of the origin story here, but I remember, and I'm half of this equation so my vote counts, I think, I remember seeing her three rows up in this little tiny group and being like, wow, she's Mexican-American from LA and looked beautiful and had a white headband, like this is my image. And I saw her and asked her out and the rest is history, we're 30 years in. She was like, no, it didn't happen like that. I was like three weeks later. And so her version is not anyone here, it's fun. And…

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Tyler Finn

You're the author though, you're the storyteller.

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Dana Rao

I'm literally here right now to have a microphone. So that was great. And so she wanted to do nonprofit work. She worked in domestic violence clinic. Oh, wow. She continues to do this work today. Today she works for the Northern California Innocence Project at Santa Clara, getting wrongfully convicted people out of jail. That was where she wanted to go. I actually wanted to be a public defender. I liked speaking, I liked being able to lead. I wanted to help people. But I had already gone through this very, very poor, stressful period of time. And what I'll say about money is, because people talk about different ways. You can romanticize being poor, but it's very, very stressful. And you don't need a lot of money to get to a place where you're happy. And you don't need to spend your life making money for material things that actually doesn't make you happy. But you do need a certain amount of money to get rid of that stress. And that stress is no joke. I was getting red bills from the electricity company, you know, all that stuff, right? Like, that is not fun. So I was walking away from that, and I'm like, I don't wanna do that anymore. So we are both not going into some kind of low-paying, non-profit career. I'm like, I'm out. Like, I'm not interested. I had a funny story. When I was, during that year or whatever, I actually got shingles. Like, everyone talks about shingles now. 

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Tyler Finn

Oh wow. 

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Dana Rao

Yeah, it's crazy. And so I didn't know what they were. So I went to the emergency room. I didn't have health insurance. And the guys are looking at me. He's like, you shouldn't have shingles. You're whatever, 23. Yeah. And he's like, you probably have cancer or AIDS. That's what he told me. I didn't have either. But you know, the bedside man are these emergency room guys. But what he ended up saying was like, you're just really stressed. Like that's the only way you could have your immune system so low that this thing could compromise you during age and that's the reality of that. So that's why I was like, I don't want any part of it. And I had an engineering degree, I loved technology. And GW, where I went, was great at patents. Like they were known as a law school that was good at patents. And so I just chose that path. I'm like, I'm always gonna be, how many engineers are there that went to law school? I'm always gonna have a job. That was…

‍

Tyler Finn

Yeah

‍

Dana Rao

That was how that was my math. And so she's obviously I mentioned she went to UCLA, but she's from Northern California. So she wanted to move back. And I wanted eventually to be in house. And there are no companies on the East Coast, really, if you want to be in tech. And so I said, Great, we're gonna move to the Bay Area. And I'm gonna take a IP job, law job, and we'll see what happens. And so I joined Femicom West at the time, and they're a great corporate law firm, mostly corporate-focused law firm in Palo Alto. And it was really great for me because I started off doing patents, I wrote patents, but they really had an unusual appetite for flexibility. So for me, while I loved writing patents, I wanted to do other things. And so I got the opportunity to work on litigation, work on licensing, general commercial licensing in my five years there. And I really enjoyed all of it. I just enjoyed doing different things. I loved the whole aspect of the law. And I actually loved being in a law firm. I loved other lawyers and the intellectual challenge of that. But five years into it, we had our first daughter in 2000. And it was just clear that looking ahead, that, you know, this was not the world's greatest lifestyle, if you want to spend time with your kids. And so my wife and I had that conversation. And I also wanted to work at a company because when I was at GE, I knew what it was like to be kind of mission aligned. And I wanted that like, as an outside lawyer, you are transactional by nature. You know, you have your law firm is your team, but really the work you're doing every day is probably transactional even though you can develop really, you know, great relationships with particular clients. And so I knew that was true. And I also realized that my favorite parts of my job at the law firm was when I got to talk to like startup CTOs and help them solve business problems. And that's what I wanted to do. And that's what the in-house job I imagined would be like. So I joined Microsoft. Everyone thought I was crazy because everyone hated Microsoft. They refer to them as the evil empire in the Bay Area. I had people at my law firm saying that I could never work with them again if I was going to join someone as evil as Microsoft. And I don't care. I'm a business person. I've never understood demonizing companies. I'll just try to make money. And there's plenty of demons out there. Go attackthe people trying to do harm. Everyone else is just trying to make a dollar. And if you root for a particular company, trust me, they're just trying to make a dollar.

‍

Tyler Finn

Yeah.

‍

Dana Rao

Like, so it's- 

Tyler Finn

It's good marketing, but-

‍

Dana Rao

That's all they're doing.

‍

Tyler Finn

And let regulators regulate it. Yeah.

‍

Dana Rao

Right, and as soon as you see economic pressure, you'll see their true colors, which I don't think are bad, but other disappoint some people, right? 

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Tyler Finn

Yeah.

‍

Dana Rao

 So I always thought it was weird

‍

Dana Rao 

That people got mad about it. So I started there. I worked on their TV product, it was called Ultimate TV, which was one of the first DVRs, digital video recording, like a TV. Which is really cool, back then, you didn't even have the concept of pausing television, like it was, TV just came over as an electromagnetic signal and went into your antenna and you saw it, and if you missed it, it was gone forever, right? And so, that was really cool to see that technology flourish there.

Then I got to work on the Xbox. I got to work on Bing, you know, right after Google launched, we created our, Bing is still around. I got to work on Zune, which is our little music player.

‍

Tyler Finn

Oh, I remember that, yeah. MP3s, yeah.

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Dana Rao

And we invented, I will say, we invented the subscription streaming model. So you subscribed to songs that got downloaded to the Zune. And Steve Jobs said famously no one is going to want to rent music when he made fun of our zune. 

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Tyler Finn

I forgot about that. 

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Dana Rao 

Yeah it's quite funny because obviously subscription is whatever. But we were way too early for our times as zoom failed. But I really loved the work I was doing

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because I loved working on technology that was in the business at Microsoft. It was not successful, but that's where I wanted to be because all the negotiations are harder. The problems are harder and again people when they think about their careers. It's not always about like the money or the success from the business. It's what you're getting out of it and what makes you happy. For me it's solving problems, solving hard problems and so trying to solve the mobile phone problem from Microsoft was the biggest problem, right? We had a Windows mobile operating system, which we were making, you know, $10 a device for years on. And then all of a sudden, you know, Apple showed up with the iPhone and then Google showed up with Android and Android was free and our whole business model was being questioned. And, and so we were, you know, I was the chief IP attorney for that group and, and trying to solve those problems is so interesting and complicated.

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Tyler Finn

You told me when we were prepping about some of the IP acquisitions that you did and you referenced Nortel and how that kicked off sort of the patent troll movement, which you know, lots of companies deal with today, not just companies the size of Microsoft. I'm curious to hear a little bit about that. That's not something I know a lot about. 

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Dana Rao

The Nortel acquisition, I mean, I don't know that anyone's connected the dots, but I live through the dots. So I feel like I see the dots. So at Microsoft, where we were, we were trying to decide if we wanted to build hardware or continue with a software play. And our software play was our operating system. And again, being undercut by a free Android operating system. 

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Tyler Finn

Sure. 

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Dana Rao

Right. And so our $10 against their free, not much of a choice there. So I worked with the president of the entertainment devices team. His name is Robbie Bach, a great person. And the first thing I did was say, hey, look, why don't we go charge a patent license fee for all the Android because they're free. And so we spent a bunch of time looking at different portfolios and what patents we had and other people. And he's like, do you think we can do it Dana? I'm like, let's do it. And he's like, how much can we get? And I'm like, let's, let's charge everyone $7 a phone. And, uh, and, uh, and I say that, cause people are like, where'd that number come from? I make the number came from because someone wants to charge me $7 a DVR box. And I'm like, and I make, I always make that joke because like, that's how damages work. Right. They're just made up. Like they're all the science is all, you know, all these Georgia Pacific factors and everything is all just crazy. End of the day, people are just picking numbers and going with it, right? And so I picked the $7 and it turned into this huge program for Microsoft. And so I was trying to figure out ways to allow us to get into hardware if we wanted to, and also shore up that licensing program to continue to give us that advantage. If you're going to get into phones, the biggest problem you have for phones is the licensing of the wireless communication standards patents. At the time it was 3G. So if you wanted to get in there, you had to pay a huge royalty. Everyone did. Apple, everyone paid this huge royalty to all these patent holders. And the next thing coming was 4G, LTE. And so Nortel goes bankrupt, or is going bankrupt, going through the bankruptcy process, and one of the things they're auctioning off are their patents. And everybody at the same time was sort of like, they probably have 4G patents, like the next generation of patents.

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Tyler Finn

I see.

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Dana Rao 

And so I said, look, this is going to be a once in a lifetime opportunity. I don't know if we're going to go into hardware, but I know this could help the licensing program because everyone's going to need these kinds of patents. 

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Tyler Finn

Right. 

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Dana Rao

So I made this big pitch about why we should go spend money on this. And we decided to form a coalition with Apple, Sony, Ericsson, and RIM, the maker of BlackBerry. The five of us got together and said, we're going to bid against Google and Intel, who are the other people in this auction. And so it ended up being an auction. Bankruptcies, when they have an asset that's in dispute, they have an actual auction. And so I had to go get permission from Microsoft for I'll just say hundreds of millions of dollars as our part of it. And there was an actual auction in New York, paddles, the whole thing, and I stayed in California,but when the licensing team was there and calling back and like, this is the number, and yeah, the portfolio went for a billion dollars. 

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Tyler Finn

Wow. 

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Dana Rao

I mean, it was crazy. And we won and we were very excited about winning, but I mean a billion dollars. And so that really set everyone's mind on, these patents are really, really worth something.

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Tyler Finn

Yes.

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Dana Rao

And what else could they be worth, right? So that was the one thing. The funny part, the aggression on this, is afterwards we had to divide up the patents, and we won, the five of us. And we did a straight fantasy football draft for them. Literally, it was in the contract. In the contract, one of the things I negotiated was we were gonna get our first five picks. So we got to pick the first five. Off the top. So we picked the first five. So the first five rounds of the draft, we were out because we had already gotten our five, but we had picked them in advance. So it was kind of like having the number one pick.

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Tyler Finn

Yeah.

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Dana Rao

And then after that, we were last for the next five rounds of the draft. And then we were like in the middle, like, you know, randomly snake or reverse snake order. So he spent like four weeks before the draft, you know, with the patent firm, analyzing all the patents and doing claim charts to figure out which ones are the best and then picking our five. It was, it was crazy. And just like us at that little conference table with the other companies and we're all just, yeah, it was a fantasy.

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Tyler Finn

That sounds fun. Honestly, that sounds really fun. People think of IP law as being... that sounds really fun. 

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Dana Rao

And I was in a fantasy football league with my Fenwick colleagues, so that was sort of why that model made sense to me. But anyway, after that, I think everyone got very excited about the value patents. But I do think that they misunderstood why it went for a billion. It went for a billion because those are standard essential patents for the next generation mobile phones. And you had companies like Apple and Google, who are looking at this as an existential threat to them bidding that value up, right? But everyone took away a different lesson and then you start seeing all these, what we refer to as patent trolls, but patent lawyers are lawyers buying patents and then suing people and just trying to make money and then this whole industry started, which I then faced when I joined Adobe and started running litigation and seeing the problem I had helped create on the other side. 

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Dana Rao Tyler Finn

You created a lot of value and then the value became evident to other people who were just trying to make a buck.

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Why leave a place like Microsoft then? And I guess also I'm interested in the transition out of IP and into a much more generalist role as GC then a few years later. I think for me the question is about leaving Adobe, I mean going to Adobe and leaving Microsoft. I mean I love Microsoft, I love the people there, and love the culture, but I didn't want to go to Seattle because I had undiagnosed seasonal mood disorder.

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Tyler Finn

I'm going to Seattle tomorrow and I'm hoping that it's going to be clear skies. 

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Dana Rao

Back then, climate change has actually helped in Seattle, but back then it was literally September through March it was gray. There's no way I could do that. So that was out of the table for me and eventually you do have to move here when I get to really high positions. So I felt that. And I wanted to spend more time with my kids, my kids are 10 and eight. And in order to do my Microsoft job, I was managing teams in Microsoft in Seattle. I was flying back and forth every other week and it was just really hard to spend quality time with them. And so I wanted a someplace local, I wanted to still be in software. And Adobe at the time wasn't doing great. I mean, their stock was 34, just about to move to the cloud with their subscription model. It's really kicked off 12 years of success, but. At the time. You know, it was a tricky decision because, again, it was kind of like going to Microsoft, everyone was like, why, why Adobe? And then one of my friends is like, hey, look, if they do, they do great. You're going to do great. And if you poorly, you get to see everybody on their patents. And I'm like, yeah, you're right. There's like de-risk for me. So I'm like, either way, it's gonna work out. 

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Tyler Finn

So that's what it's like. Not de-risk for Adobe, but de-risk for you. Yeah, exactly.

‍

Dana Rao

At the time, I didn't have any loyalty to Adobe. I hadn't even taken a job yet. So it wasn't like an emotional thing, right? And that's the thing about being a lawyer. So I took the job and then shortly after, we got a new GC and he asked me to take over litigation, mostly because all of our litigation was patent troll litigation, and so he just wanted the person who knew the patents to work on it. And that was super interesting. The first trial I had, actually, before the GC started, and so the GC hired me, was there. We were about to go to trial in Boston for a patent troll, and she asked me, hey, look, assess the case, give me a recommendation of what you want to do. And so we were in trial, and it was a case I thought, you know, we should win. I talked to the witnesses, talked, look, the patents, patents are stupid. And, and, you know, the first week, and they wanted like $30 million, whatever. And the first week, you know, they put on a case, didn't look great, because it never does look great when the other side's presenting and you're defending. And they kept saying $30 million, $30 million. And then we put our case up. And, you know, again, I felt very good about her case. And then their number started coming down. Thirty million, twenty million, ten million, whatever. And so until like two days and I kept saying, not settling, not settling, not selling, and then the night before the case went to the jury, the night before the jury was going to come back with a verdict, they said, hey, walk away. Like they completely lost faith that they were going to win. 

‍

Tyler Finn

Wow. 

‍

Dana Rao 

So, I was like, no. And the reason I said no was strategically like winning this case doesn't mean anything.

‍

Tyler Finn

Uh-huh.

‍

Dana Rao

What I really needed was a deterrence value. Yes. Of winning. Right. Like that was much more valuable to me than whatever I'm going to lose in this verdict if it goes the wrong way. What I love about Adobe was, you know, I told that to the GC. She's like, let's go talk to Shantanu, who's a CEO. It's the first time I met him. I go into the office. I'm explaining like why I think we should roll the dice with a jury verdict, which could go either way, as you know. And he's like, do you believe in your analysis? And I said, I believe in it. And he's like, all right, do it. And that was just like, wow, so empowering, right? But I had all this conviction.

‍

Tyler Finn

Yes.

‍

Dana Rao

Obviously, given how everything worked out, the answer was jury came back, patent's invalid, not infringed. Quite a different story if it hadn't gone that way. But what was really interesting to me was all the executives afterwards were so happy. And you just forget this as a lawyer. And they were happy because they felt vindicated because they felt like they were being accused of theft. Like they didn't think about this as patent trolls, but they were thinking, someone said that we copied their idea and we didn't copy their idea. And how could you say that? And there was just this sort of righteous vindication that was really fun to see and just really gave me that motivation. So I felt convicted that this is the right way to go, deterrence, and I felt convicted that at the end of the day a trial will vindicate me, right? So we changed our strategy, which was before we settled all these patent troll cases, because patent trolls typically will come to you with a nuisance value settlement offer because they don't want to go to trial, they just want to give you a price that is less than the cost of going to trial and hope you will do the math and just give them money. 

‍

Tyler Finn

You don't want to spend a lot of money on outside counsel. 

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Dana Rao

It's basically extortion. And so we did three things. One we said we're going to adopt a strategy of if we think the patent is invalid, we're going to take it to the trial and make it public about it. Second thing we're going to do is come up with, at the time was fairly revolutionary, a litigation flat fee structure for trials. So we need to cost certainty. Like I can't just go to my CFO and say, it's just going to cost some random amount of money to do this strategy. I'm like, we need to know every time we go to trial, here's what it's going to be. So we had flat fee for, you know, if we get to the summary judgment, flat fee, if you get to this point, flat fee, if you go to trial, like you just stack them up. And now I could go to the CFO and say, this is what this looks like. That was critical to be able to design this and then get law firms to agree to it. And then that was the second thing. And the third thing was, and this is what I learned from Microsoft, is like, change the world. Like, why do we have to accept this? And let's, let's change the law. The law is being stacked against the corporation defendants in favor of patent holders. There's no reason there's imbalance. They didn't understand the concept of patent trolls when their law was passed. And here's the problem. Everyone's got it. So we did all three things. Um, the deterrence part was funny because I would get like offers like $10,000 settlement offers. My head of litigation who then reported to me was like, we should take this, right? I'm like, we're not taking it.

‍

Tyler Finn

Yeah.

‍

Dana Rao

It's zero. I need these people to look at Adobe and say, let's just go sue Intuit. That was a joke.

‍

Tyler Finn

Really?

‍

Dana Rao

Apologies to all the Intuit fans out there. But that's what I would say, you know, we need to. So that was important. Law firms did a great job, the flat fee. But then we were trying to figure out how to change the law, and we had other willing participants. So I joined up with Oracle, Google, and Cisco, all our heads of IP, and we created a new foundation, the Coalition for Patent Fairness, and as a lobbying arm in DC to push a new law on how to fix all these problems. And we had just passed the American Events Act like four years before, so Congress was not interested in the new law, but this problem was so dire that they actually would listen and were actually engaged in the conversation. So I was in DC a lot. 

‍

Tyler Finn

Yeah.

‍

Dana Rao

Writing a law, shaping a law on venue and all the different aspects that were driving this. And I got to testify twice in front of, once in front of the Senate Judiciary Committee, once in front of the House Judiciary Committee. All the bills got killed by the Trial Lawyer Lobbyist Association in the Senate Judiciary Committee. They got voted out of the House, 435 to whatever, but then died in the Senate Judiciary Committee. But it did change the law because it had a whole conversation start about patent trolls, which no one even used the word patent trolls before. And I knew we won because we filed as amicus on a bunch of cases, our coalition and Scalia and one of his opinions referred to the other side as a patent troll.

‍

Tyler Finn

Interesting.

‍

Dana Rao 

And I'm like, once you win the vernacular, you've won the argument. And that's why communications is such an important tool for lawyers. A lot of people don't think about it, but even during that time, every time we won a trial, I would do an interview and people like, oh, you shouldn't do it. I'm like, I'm always doing interview. I want everyone to know what the other side was, right? To drive that conversation. They're not independent inventors working out of the garage. That's not who we're talking about here. Right. Right. These are just litigation funded lawyers. So, um, so that was great, but it got me to the point of being able to see a lot of things and do a lot of big policy things. And then my general counsel retired and the CEO was said, I want to hire internally. And so he asked the people who were interested and there was four of us to, to bring up a vision of what you thought about Adobe and Adobe Legal and send them an email. And so I did that. And because of my intellectual curiosity, I had a lot of thoughts about Adobe's business and where it could be better. I had a lot of thoughts about our legal department and how we could be better from a legal operations perspective. And I had a lot of thoughts about AI. We hadn't even started on the AI journey, but AI had been something I've been paying attention to and working on for my career. And when I was in law school, my law journal article, which got published, was on AI. It was on who owns the output of AI. It's called neural networks, here, there, and everywhere. 

‍

Tyler Finn

Way ahead of... 

‍

Dana Rao 

1997. Too ahead. 

‍

Tyler Finn

That's amazing. 

‍

Dana Rao

And it's probably terrible, so don't go reading. But it's what I've always thought about. And so in my email, I talk about AI and that very question of who owns it and how we're going to take advantage of it. And so I really feel like that intellectual curiosity, the ability to stay involved in the world and bring all that business knowledge into that answer has really helped me stand out in that interview process and made him consider me. And the other thing was he's an engineer, right? Shot down, right? And so he and I spoke the same language. We had very high bandwidth conversations on products and technologies, where things were going. And so when I became GC, I really felt like I had the opportunity to treat it as GC as a CTO. You know, I thought about it, like, what can I do to help with law and technology and policy drive our technical agenda forward, understanding where trends are going and use the law to get there.

‍

Tyler Finn

We're running short on time. I might have to have you back to talk about all the work that you did on AI. I do want to ask you some of my sort of traditional closing questions because I think a few of them are fun and I'm really curious for your view on one of them. The first one is maybe think back to when you were GC.

‍

What was your favorite part of your day to day in the job? 

‍

Dana Rao 

Day to day I really enjoyed one on ones with people. So the way I managed was I had one-on-ones, like hour-long one-on-ones with all my directs at least once a month, and then I would never pay any attention to anything they were doing. That was my deep dive, talk to me, ask me questions. I ask you a bunch of questions, and then off you go, and I don't go sit in meetings with them or whatever. But I enjoyed it because it was fun for me just to sit there and talk to them, learn about them, learn about their lives, their careers, their issues, everything. And just those are my favorite. And then skip level 101s were even more fun for me because I got to go throughout or I did tons and tons of skip levels because I love seeing the junior lawyers and the ones I felt like had all this potential. And some people just needed doors opened and you can help them. And they weren't even just lawyers. When I started AI ethics at Adobe, if I come back, you know, we can talk about it.

‍

Tyler Finn

Yeah.

‍

Dana Rao

Um, but there was, there was a woman named Grace, she, she, she was just a program manager, engineering program manager. And I, she was helping me out in a project and I'm just like, this is like the smartest person I've ever met. Like, what are you doing? Bury 75 layers underneath, you know, some product guy, right? Like they don't appreciate you. Yeah. So I pulled her out and had her run AI ethics for me. That's so cool. And she still is doing it to this day. Now she speaks at conferences and it's amazing. But there's a lot of people like that. Like if you can just get the time to spend time with them and see who they are and what makes them tick, you can really let their success bloom. 

‍

Tyler Finn

Do you have a professional pet peeve?

‍

Dana Rao 

I'm a hard grader, I will say. No one who works for me will say anything different. So my biggest pet peeve is not being prepared for meetings. I really think it's about respect. And people will show up at meetings constantly and haven't done the work, haven't thought through if they're a lawyer, the law, the facts, the policy,

‍

if they're a business person, haven't modeled the money or the implications or the technology or the effort or whatever. Haven't talked to the other people, other stakeholders to get an aligned point of view. They haven't done the work. And you sit there and you're like five minutes in, you're like, what, what are we doing here? This is a wasted hour. We're going to have to come back again next week. We're going to talk about everything all over again. And like, and it's drove me crazy. 

‍

Tyler Finn

We've all been there. I think. Do you have, I mean, you're writing a book. Do you have a book that you'd want to recommend to our audience? This could be a business book or it could just be something fun. 

‍

Dana Rao 

I don't read business books.

‍

Tyler Finn

That's not a bad character trait or... 

‍

Dana Rao

I do, yeah. So I just finished reading. My wife loves this author, Leanne Moriarty, and I now love her too, on her recommendation. I literally just finished yesterday, so I also recommended it. This book called Here One Moment. It's her latest book. And so she, it's just, it's regular fiction. She's not science fiction or anything. But this particular book is very fun premise in the first page. So I'm not giving any way. But on a plane, a woman who you don't know who she is, but appears to be some kind of fortune teller tells everybody on the plane, the how they're going to die and when they're going to die. 

‍

Tyler Finn

Okay. 

‍

Dana Rao

And then the rest of the book is about the consequences of that.

‍

Tyler Finn

Wow.

‍

Dana Rao

Those predictions. Great book. I mean, I actually was up till midnight two nights ago finishing it because I was so taken by it. But she's an amazing writer. 

‍

Tyler Finn

That sounds great. I don't think I'd be happy if I am sitting on my flight tomorrow and someone came up to me and told me when I was going to die. 

‍

Dana Rao 

People got like 100 years old of, you know, heart failure, you know what I'm saying? 

‍

Tyler Finn

Final question for you, my traditional closing question for my guests. It's if you could think back on your days of being a young lawyer, maybe just graduating from GW Law, something that you know now that you wish that you'd known back then.

‍

Dana Rao 

Yeah, I would say I have two answers. One is maybe to take all the pressure off of people. I wouldn't be I wouldn't have accomplished anything I've accomplished if I didn't make all the mistakes I made. I firmly believe that. So I wouldn't change anything. Even the sleeping on the couch part. The singles were terrible. So painful. I have not gotten the vaccine yet. My wife keeps getting on me, but I'm like, I don't want to take it. But regardless, I wouldn't change anything. Like in terms of mistakes, like I wouldn't fix any of the problems. I think what you don't appreciate, which I got a chance to appreciate quicker because of Reno was that you are free. There is a certain amount of freedom in your career and in their choices that you have that is not apparent to you when you're in the grind and you feel like you have to do this thing. You have to impress this person. You have to build these hours. You have to hit this project and that's all you can do. And having that ability to have that perspective and take a deep breath and say this isn't all there is. There's more to this than life. And, you know, we didn't get a chance to talk about my three-year framework about how you can Pause every three years and yeah examine the pros and cons of what's going on in your world That's so important to do and even as early as the beginning of your career to make sure you're checking in with yourself about what really matters because Someone could come up to you on a plane tomorrow and tell you you're gonna die in three. 

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Tyler Finn

That's a great that's a great circular, great circular way to end our conversation. I would actually love to do a part two. I know you're spending a lot more time in New York these days. I do a bunch of recordings in studios there. I think that would be a lot of fun. I think we still have a lot more to talk about. 

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Dana Rao

Yeah, absolutely. I'd love to.

‍

Tyler Finn

Thanks for being here. 

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Dana Rao

Thanks, Tyler. 

‍

Tyler Finn

Thanks for being here. Thanks, Tyler. and we hope to see you next time.

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