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Waleed Diab

Director & Global Head of Recorded Music Business Development


New York, New York

Past affiliations include law department, Viacom.

JD Benjamin N. Cardozo School of Law   BS University of Maryland

In tune with the business of music at YouTube

waleed headshot 2022

On his role as Global Head of Recorded Music Development at YouTube

On needing to understand financial concepts when you move to business

On finding ways to say yes versus no which is how lawyers are trained

Listen to interview:

Part One:

Part Two:

Full Transcript

ex judicata: So, you went to Cardozo and graduated. Tell me about your career path.

Waleed Diab: I graduated in 2004. I tried a bunch of different things in law school. I did an Alexander Fellows Program clerkship through Cardozo. I interned at an entertainment law firm. I also interned at a media company called Classic Media, which was basically in the business of buying up old entertainment properties and then exploiting them.

When I graduated, I didn’t have a job lined up. I took the bar and passed it, and I was sort of searching for what my first job would be. I did some project-based litigation work at Skadden and some document review and things like that related to litigation for Skadden’s litigation department. That work was totally not my style or what I wanted to do.

ex judicata: So how did you get from that job into one in the music field?

Waleed Diab: It was actually through my connections at Classic Media that I ultimately got my first job after law school. While I was working at Skadden, I was in touch with my former boss (Antonious Porch, who is currently the General Counsel of SoundCloud) from Classic Media, and he said, “Hey, there’s this job at Viacom. It’s a very low-level contract manager position, but it’s in the legal department. In terms of getting your foot in the door, it’d be a good way to do that.” So I pursued that role and, once I was in the organization, it parlayed itself into a bunch of different jobs. I ultimately had four different positions at Viacom within the legal department, which was wonderful. It was really, really great. My title just before I left was Senior Counsel of Music Strategy and Relations. I sort of found my way in through the organization to exactly what I really wanted to work on, which was music.

ex judicata: Wow, that’s great. You know, it’s so hard to get into that type of industry and it’s not uncommon to graduate without a job. But you had great experience. It’s just a very tough market.

Waleed Diab: Absolutely, and I think it’s also a reminder; I often tell people a lot of it is chance. I don’t think we should be too hard on ourselves, but we also shouldn’t give ourselves too much credit for where we ultimately land. I think a lot of these things are heavily dependent on being in the right place at the right time, but you can make opportunities by putting yourself out there, meeting a lot of people, and then trying to steer yourself toward the things that make you happy.

I remember having this very pivotal discussion with a mentor at the time, who was guiding me around what I really wanted to do. While working at Skadden on a project basis, the firm offered me a full-time job and it was more money than I’d ever seen. I was going to be making close to six figures and I could not believe that was even something in the books for me.

ex judicata: But you didn’t take the offer. That level of pay at that point in time was huge. It must have been hard to pass that up.

Waleed Diab: I asked myself if I was going to be happy doing that kind of work. Am I actually going to want to show up to work every single day? The answer was absolutely not. And so I went and took this job at Viacom where literally my first paycheck was $523 for a week’s worth of work.

ex judicata: Wow. That must have been tough!

Waleed Diab: It was. It was really hard. I had law school loans and I had to live in New York City. I moved out to White Plains and lived with my brother for a while just because I couldn’t afford to pay for anything. But I was playing the long game. I figured I’d do this for a while. I really only had that job for about three months before I got a full-time job in the legal department at MTV. The pay sort of notched up in small increments, but I was so motivated by being close to the music industry and being around music that it didn’t feel like work. I would put in endless hours, nights and weekends, and I didn’t even think about it because I was so excited to be close to it.

ex judicata: It’s so true. When you love what you do, it doesn’t feel like work, and then you’re getting paid for it on top of it, which is ideal. You had an advantage there. Having worked at Skadden, you knew you didn’t want that path. You didn’t like the work. It wasn’t for you. One of the most helpful things in determining a career path is ruling out what you don’t want to do. It’s an experience that can help you determine the right path forward.

Waleed Diab: Exactly. 100%.

ex judicata: So tell me about what you’re doing at YouTube.

Waleed Diab: Sure. It’s definitely interesting work. I lead our record label business development team. What that means is I am responsible for helping music record labels make money on YouTube. And we make money in a number of different ways. Our two most mature businesses are the advertising business where we sell ads against music content and then we share in the ad revenue with the music companies. Then we have a more recent but fast-growing business, which is our subscription business, where we charge end users for premium ad-free access to YouTube, and they can save the YouTube videos and music content to their devices. For that, we share in revenue with the music industry as well. So those are our twin engines of growth. They’re really, really large businesses.

Just to give you a little bit of context, we announced a few months ago that we paid out $6 billion to the music industry in the previous 12 months. That’s a large amount of value being driven back to rightsholders in a single year so that’s a substantial business. In addition, we’ve been heavily investing our Shorts product, which is a new discovery and engagement format that allows users to find new music and artists and then dive deeper into that artist’s repertoire on YouTube’s existing ad-supported and subscription offerings. Our publicly stated goal is to be the number one driver of revenue to the industry. Right now, Spotify is the industry’s number one revenue driver because it has a much more mature subscription business.But we believe we’re on our way to becoming number one.

ex judicata: It’s all about business development and getting ahead of the curve, gaining market share. So more precisely, what does your role entail?

Waleed Diab: I work with all recorded music providers, or record labels as they’re generally known. You probably know the biggest ones that I deal with are Universal Music Group, Sony Music Group, Warner Music Group, as well as thousands of independent record labels. I help them optimize their business on the platform.

I got into this because when I started at Google, I was on the legal team drafting and negotiating agreements with record labels, music publishers, artists, you name it. Believe it or not, at the time, there were only two dedicated music lawyers at Google. As a result, I got a ton of experience. I got to work on basically everything under the sun that was music related, and I ultimately navigated toward the record label segment of the business because it’s where the majority of the value still remains in the music business. Those are the people who tend to make all of the interesting decisions, more so than other stakeholders. I would say more than music publishers, more than artists, and more than managers. The record labels really are the ones helping shape the future of the music business.

ex judicata: That was true for film years ago. The studios were the drivers, they controlled the contracts, everything. People were locked into working with a studio. It was a big business.

Waleed Diab: Absolutely. So, I think that element of it is very exciting for me. I spend probably most of my time now thinking about broad strategies regarding where we want the business to be in three, five, ten years. So that’s super, super exciting work.

ex judicata: That does sound exciting. It sounds like a lot of fun too. How did this opportunity come to you from working at Google? Your role at Google was focused on legal work. Now you’re doing more business development. Although, I imagine there are legal aspects to what you’re doing also.

Waleed Diab: Yeah, there are. I’d been on the legal team at Google for five years. As you mentioned earlier, knowing what you don’t like is an experience that can help get you to the right spot. What I realized is I always felt like I was sort of playing a lawyer, you know, like I was acting like a lawyer. I knew what I had to do, and I think I did a good job at it, but I was always sort of playing a role, playing a part. I was always thinking there must be some off-ramp, something else that I’m going to do because I didn’t fancy myself a general counsel or partner at a law firm. I couldn’t see myself being happy doing that.

After five years on the legal team, a role opened on the business side and the manager of the team at the time approached me and she asked, “What do you think about switching over and doing this on the business side? I think you’d be really good at it.” I had to think about it. Ultimately, I decided to take the job. I figured that if you’re going to move from legal to business, you’re taking a risk. You have to use different types of skills and you have to be able to be effective in a different way. I thought I would never have as good of an opportunity as that to do it because I had already built credibility and built a lot of relationships within the company. So, people knew who I was and knew what my work product was. If I was going to take a risk this was kind of a safe space to do it.

ex judicata: Were you scared? It is a different skill set and a very different role.

Waleed Diab: I’ll say I spent the first six to nine months really scared. I asked myself, “Have I made a big mistake?” When you’re a lawyer, even if you’re having a bad day or you’re having a bad week and you’re feeling like, Oh, I haven’t really done that much, I haven’t accomplished that much, you always have ways to reassure yourself that you’re adding value. Maybe you turn in a redline of a contract, or you go research some legal issue and you feel you’ve done what you needed to do to add value.

When I moved over to the business side, I couldn’t rely on those things anymore because somebody else was responsible for them. I had to figure out new skills and a new way to provide value. I was then responsible for things like evaluating how the business was performing, the economics of our relationships with the record labels, and the economic or financial goal we wanted to achieve. These were things that were very uncomfortable for me at the time. But what I realized about nine to 12 months in was that I actually knew more than I thought I did by virtue of the fact that I had worked on these deals as a lawyer. Although oftentimes as a lawyer, I’d be focused on drafting and the legal language, reps, warranties, and indemnities—what you might call the structural issues of an agreement, I was still absorbing the economics and business elements of the deals as well.

ex judicata: Right, and in doing so, you were positioning the client for the future, helping it determine the path forward.

Waleed Diab: Exactly. And so though I was initially uncomfortable in making the transition, I found my groove and became more comfortable. It’s been almost seven years now and it’s been a great sort of evolution on the business side as well.

ex judicata: What was most challenging when you came over to the business side? It sounds as if having to develop and utilize a different skill set and looking at things from a different perspective was really tough. Were those your biggest challenges?

Waleed Diab: Yeah, I think those were probably the biggest challenges. There are a lot of skills that you learn as a lawyer that were really helpful, including critical thinking, and objective thinking. In law school, they teach you to think in terms of incentives and power dynamics. A lot of what we learn in legal courses includes considering what incentives we want to build into contracts, the power dynamics, which is very helpful when you’re on the business side because a lot of things come back to incentives and the power dynamics, who controls the power in a particular relationship. Those types of things parlay themselves very well into the business side of things. I would say I faced challenges when it came to my lack of facility with financial concepts. I considered taking a nighttime or weekend MBA course. But I didn’t know if I wanted to do that for two or three years, so I ended up getting a book called “The Ten Day MBA,” and I read it on my winter holiday vacation. Frankly, that was more than enough.

ex judicata: Oh, that’s really funny.

Waleed Diab: Yeah, think about it.

ex judicata: That’s pretty funny. Actually, though you’re working with a team, and your focus is on developing the business. I’m sure there are people who can handle the numbers. Although you do have to have a basic understanding, you don’t have to be able to delve that deep into the financial aspects. I find that understanding the power dynamics is really key in anything. What do you have that you can bring to the table? What’s really essential to the other party? Being about to figure those things out is hugely important.

Waleed Diab: Exactly.

ex judicata: When you want to develop a business, understanding where the other party wants to get and how you can help them get there contributes greatly to your strength in negotiating. So, selling is an important element of law practice that translates well. People don’t think of sales when they think of law, but selling is essentially selling yourself as the lawyer, selling a deal. They can pick somebody else to represent them. As stupid as this may sound, likability has become important too. If they like you, they’re willing to negotiate with you. Shifting gears, what does a typical day look like for you?

Waleed Diab: So on a typical day, I spend probably 60% of my time working internally. I manage a team. So oftentimes I’m guiding my team members on the deals they’re working on or providing advice or handling general management-related issues. The other 40% of my time I spend externally with partners, building relationships. As you said, the likeability aspect is very important. So, I spend a great deal of time making sure that I maintain those strong connections with my partners. Those relationships really matter, especially when I have to turn to them and ask for things or when I need to push them to see the business the way I see it. 

So my day typically includes internal meetings where we’re pushing to get approval for a particular deal and spending a lot of my time strategizing for the future. We have a strategy team and a finance team and my team kind of marries those together with the legal team to figure out which direction we want to steer the business. We think a lot in terms of particular partnerships. But we also strategize on a programmatic basis, considering where we want to take record labels in terms of their interactions with our business. That requires a very, very deep knowledge of not just our partners and what is driving and motivating them and what their needs are, but also the overall landscape, whether it’s the stuff that’s happening in our present-day Web 2.0 business or the future, whether it’s Web 3 and what’s happening in the emerging technologies space. I spent a lot of my time on that.

Then, of course, there’s the firefighting element of what we do. Unexpected things always pop up. Our partners, because of their reach, oftentimes have some escalation or some crazy drama with a particular artist. You may remember a few months ago, what went on with Kanye West. Everybody was watching that. I was dealing with that on the inside addressing questions regarding our policy positions like what is YouTube’s perspective on this?

In general, record labels have a fiduciary duty to their artists by virtue of their artist contracts. But at the same time, they may feel conflicted based on their moral outlook, the identity, and brand they want to have for their record label, etc. We partner with these record labels and also have relationships with the artists, so oftentimes we’re forced to navigate these sorts of issues. So, there’s always that element. Whether it’s Cardi B at Warner Music Group or Taylor Swift, who’s also on Universal Music Group, each of these artists has unique issues that pop up. Although on the business side for us, they’re narrow in terms of impact, they are outsized in terms of the volume of work and effort that it takes to manage these escalations because they can be very high profile.

ex judicata: Right. Anything you say or do is out there in seconds and through the world. That’s the nature of the Internet. You need to stay ahead of what’s going on, structuring and planning for the future.

Waleed Diab: Right.

ex judicata: What do you love the most about what you do?

Waleed Diab: I love that I’m helping artists and record labels make a living and driving revenue back into creative culture. When I was coming out of law school, there were a lot of people that said, “Do not go work in the music industry.” I graduated in the darkest days of the music industry, in 2004. There was already a massive decline in revenue happening. There’s a great program, by the way, on Netflix called “The Playlist.” It’s an editorialized story of Spotify and it starts out in the dark days of the music industry when everybody was just stealing music online. One of the primary ways that people were getting music was through file-sharing sites and they were just taking it for free. It was a really bleak outlook for artists because there was no assurance that they were going to be able to make a living and survive as artists.

People with families and careers that had dedicated themselves to the music industry and to the craft of music were losing their jobs. There was a real human impact on them, not to mention the artists, of course, who were putting their hearts and souls into creating music. And I remember very clearly one of my senior managers at Viacom at the time telling me not to go into music.It’s a shrinking business. He told me to go into TV, film or gaming because there’s so much more money in those.

ex judicata: But you still went ahead.

Waleed Diab: I was so passionate about music that I had to go to work in it. And the beautiful thing now is the music industry is coming back. The growth has been phenomenal, and I actually think we have yet to see the golden age of the music industry. Back in 1999, the heyday of the music industry, people were spending on average, let’s say, $40 or $50 on music a year. You bought, let’s say, three, four CDs or maybe five CDs at $18 a pop. Now the average money spent per user can be up to $120 a year, so you’ve gone from $40 or $50 to $120 a year because if you’re a subscriber to a music service, you’re spending ten bucks a month. So the actual revenue generated from music fans has gone up. You’re also monetizing more users at that level than you probably were when you were selling CDs. So just taking the economics of that and carrying that forward, if we can get more and more people actually paying for music, I actually believe the best and the most lucrative days of the music business are still to come. And that’s just in terms of people that want to pay for music. That’s not taking into account the people that are actually paying for music by watching ads.

YouTube’s advertising business is very large and successful, and there are a lot of people that frankly just don’t care enough about music to actually go out and spend money on a subscription. There’s a really beautiful and lucrative future for music, musicians and artists. That’s what makes me most excited is I’m part of that change. I’m part of building that future that’s actually driving revenue to creative people, people that are contributing to our culture and the richness of artistic expression.  

ex judicata: It’s great to be doing something you’re passionate about it. I can really hear how much you love it. But what do you wish you knew before you went into the industry?

Waleed Diab: I have to look at my notes for this one because it took me a while to think about this. I think I was a little conflicted about it because I look at all of my experience as contributing to exactly where I am today, and I’m very grateful for that. I think I was actually mindful and present about it when it was happening and grateful while it was happening as well. But I did come up with an answer. I think early on in my career I was very obsessive about people not taking me seriously. I felt like people didn’t take me seriously because I started at MTV as a contract manager and like most organizations, it was very hierarchical, and I felt like people didn’t take me seriously because I didn’t go to Harvard, Yale or Stanford.

ex judicata: A lot of people feel that way. They feel that they’re a fraud, that they’re not going to be taken seriously, that they really don’t know stuff. But in doing a job, you build confidence and learn from each experience. Instead of looking back focused on you, let’s look at it in terms of other people who may want to get into the music industry. What challenges should they expect to face? That would really be helpful. What do they need to watch out for and how can they prepare themselves?

Waleed Diab: This is the one I think I would double down on. As you said, I think imposter syndrome is a real thing. We always think “Oh, I don’t deserve to be here. I don’t have the skills or I’m not the same class of lawyer as these people.” Law is the one profession in which people will always ask you, “Where did you go to law school?” For some other professions, people want to know where you studied, but it’s not as ingrained as it is in the legal field. So I was really hung up on that early on in my career. But I realized that if you put in the time, provide value, and dedicate yourself, you can craft your own way. The other thing that made me feel really comfortable about it was when I got to Google, I thought, “Oh, wow, I really figured out how to sneak in the back door because I’m working in the legal department.”

At the time, Google’s legal department was recognized as like the top legal department year after year, and this was the early 2010s — 2013, 2014. I just couldn’t believe it. But at Google, we talk a lot about impostor syndrome. I love that because you have some of the brightest, most capable people in the world at this company and yet imposter syndrome is still a thing for many people here. I think if we can talk about it at Google, then anybody that’s graduating from Cardozo or another non-Ivy League law school can absolutely acknowledge that and realize that they’re adding real value and they should be confident in themselves and confident in their skill set. Just put your head down, do your work, build your skills, put in the time, and things will pay off.

ex judicata: Did you have a mentor who helped you out?

Waleed Diab: I had many mentors. In fact, I think it’s critical to seek them out and try and build those relationships because it’s just imperative to have advice and guidance from people that have come before you. They will guide you. You don’t have to take everybody’s advice, but you should always be open to listening to it because people have great perspectives on things, and they may see things that you don’t yet see because you don’t have the experience yet.

ex judicata: Right. You need to gain perspective. You need to gain experience. I think that’s among the best suggestions for anybody interested in making a career change. Really understand what you’re getting into and have a mentor to guide you. That whole imposter syndrome concept is real. It’s very hard to go into your boss and ask a question that you think is stupid. But if you have a good mentor, someone you can rely on, you can ask those questions and get the guidance you need.

Waleed Diab: Exactly.

ex judicata: How should those who want to get into your industry go about it?

Waleed Diab: So, I think it’s a couple of things. First, put yourself out there and meet people. Every opportunity that I’ve had has somehow been through some type of personal connection, somebody that I had interacted with or met with. It’s not going to come from that alone. So, you also need to spend time educating yourself on the business and its dynamics. Go to business conferences, go to legal conferences, and try and build a network that way. Usually, some combination of the two will ultimately parlay itself into a role. The worst thing you can do is walk into an interview or networking meeting with any type of personal connection and sound like you don’t know anything about what’s happening in the industry because then you’re just wasting people’s time and you’re probably wasting your own time.

ex judicata: You are wasting your time and you’re damaging your reputation.

Waleed Diab: Exactly.

ex judicata: You have to be knowledgeable. Know your stuff. Do your research. Be prepared. It’s a lot of studying, knowing the business, knowing the industry, setting a path for yourself, and then putting yourself in a position where you can accomplish that and make the contacts you need. Breaking into this industry and phrasing it in a positive way helps a lot. What will help lawyers succeed in transitioning What are some lessons you learned that would be beneficial for people to think about?

Waleed Diab: As lawyers, we are trained to think about what’s going to go wrong. As you said earlier, contracts are about the future. Thinking about what happens if things don’t go well is part of our job and we have to do that. You’re not a good lawyer unless you’re thinking about that. However, I think what sets lawyers apart is finding a way to say yes to things. We can always find reasons to say no to things. The risk is too high.  This is not going to work out for X, Y, and Z reasons.

What really makes an impact is if you can find ways to say yes in an informed way. I’m not saying tell your clients or tell your business partners to just take a bunch of risks and do things that are ultimately not going to pan out because then you’ll have a very short-lived career. But if you can find smart ways to navigate the reasons why people would say no and come to a place where you can say yes to something, I think that is a super powerful skill.

I also think when you are in business as a lawyer or trying to move to the business side, balancing your conservatism with optimism is critical because on the business side, you’re building for the optimism, you’re building for something that is a mutually beneficial overall partnership. That’s something that I’ve seen a lot of lawyers struggle with especially if you want to be on the business side. You said earlier that you should know when you don’t want to do something. And I also think it’s important for those considering moving to the business side to really ask themselves, what is it that makes me happy? And if you’re really, happy on the risk-averse side, drafting agreements, and supporting somebody that’s taking the risk and making the decisions, and that has accountability for the performance of the business, then you may very well be better suited staying on the legal side, and that’s totally fine. I know an excellent lawyer who dabbled on the business side, but she knew in her heart of hearts that she always wanted to be legal counsel. Her awareness of that has allowed her to excel. She has a very senior role in a legal capacity, and that was the right path for her. I think it’s really important for people to be aware of what drives them.

ex judicata: Right. The whole concept of risk, risk assessment, and then protection from liability is the legal side. lawyers aren’t making the decisions for clients. They’re advising. What I think is very challenging on the business side is that you make the ultimate decisions. You make those decisions in an informed way if you’re smart, after hearing what the legal implications are, but you’re making the decisions and you have to be comfortable with doing so, right?

Waleed Diab: And you’re accountable.

ex judicata: Yes. You’re accountable for the decisions you make, whereas a lawyer advises and then the client decides what to do. Of course, the lawyer may still get blamed, but ultimately decisions are the client’s responsibility.

Waleed Diab: I will say lawyers get blamed, but ultimately the buck stops with the business. And that is very true here. I think it was true at Viacom as well. But I’ve seen it firsthand here when things don’t always go to plan. Sometimes there will be questions like, how did we get to this? We got this piece of advice. . . . But at the end of the day, it doesn’t matter because the buck stops with the business owner. We took that advice and we acted upon it.

ex judicata: People love to identify problems, and that’s what lawyers do. But the bottom line is what is the solution? What’s the path forward? There are always going to be risks.

This has been great. I really enjoyed meeting you. You were very well prepared, and I so appreciate your time.

Waleed Diab: Nancy, it was wonderful meeting you. It was super easy to talk to you and I am super happy to chat with you any time. Definitely let me know if you need anything else. Thank you.

ex judicata: Well, thank you so much and have a great weekend.

Waleed Diab: You too. Cheers. Bye.

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