Ep 1: Curiosity & Disruption in the Entertainment Industry with United Talent Agency CIO Michael Keithley

Saam: Welcome to Enterprise Software Innovators, a show where top technology executives share how they innovate at scale. Each episode covers unique insights and stories that will help you succeed as a technology leader. I’m Saam Motamedi, a general partner at Greylock Partners.

Evan: And I’m Evan Reiser, the CEO and Founder of Abnormal Security

Saam: Today on the show, we’re bringing you a conversation with Michael Keithley, Chief Information Officer at United Talent Agency, where he’s worked since 2017. 

UTA is one of the world’s top entertainment and talent companies, working across music, sports, film, podcasts, and more. Michael also serves as an advisor to multiple VC firms, and was previously CIO and CTO at Creative Artists Agency, where he worked for 24 years.

Evan: In this conversation, Michael shares how the CIO role will change over the next decade, his take on the most underestimated areas in technology, and how CIOs can level up their impact as strategic advisors.

Saam: Michael, as you know, there’s been a lot changing in technology, and the ways in which it intersects with entertainment, with new trends like e-sports, different types of influencers, and NFTs. How are you thinking about these kinds of emerging trends?

Michael: I always like to tell the story of the music business, because film, TV and music were kind of the three big areas of a traditional talent agency.

And after years and years and years of kind of a very stable business, along came this thing called Napster and MP3s, and almost overnight the business went from this stable business to, to being more or less decimated. 

Then Apple, a few years later with the iPod and the iTunes Store really changed it again. And they got people to start paying for music again. But the big change there was, it was 99 cents per song. It was an a la carte basis. And so instead of paying for the whole album, you were only buying the one or two songs that you really like. And I really think of that as a through line for a lot of the businesses and the choices we've gotten into as an agency, that you always need to do what's right for the customer, even if it's blows up your business model or changes things, you gotta do that and that's what's going to win in the end. And then finally, along came the streaming services, you know, Spotify et al. And now basically pretty much everybody has a lifelong subscription to music, right.

And so the music industry went from being decimated to kind of a nuclear winter to kind of eking its way out. And that took, you know, well over a decade to do that. The basic kind of lesson that I take away from that is that digital technology is going to have profound effects on every aspect of the entertainment industry and it's my job to help our company be prepared for that.

That's one context and the second context is generational. If anybody has kids in their house, they understand that their view of entertainment is profoundly different than what maybe some previous generations’ view of entertainment was. And, you know, that was really made real for me I remember several years ago when I brought home this nice big screen plasma display, and I set it up and I showed my son and he walked in and he was, you know, young kid. And he looked at it, he smiled and he was so happy. And he went up to it and he tried to touch it and it didn't do anything and he goes, daddy broken.

And I said, no, no, no, no, you don't understand. And he just kind of walked away and disgust, went to his room and came back with his iPad and sat down literally in front of the TV, not looking at it, watching it on his iPad. It kind of shows that generation, they want what they want on the device they want, you know, in a convenient way. That’s radically changing how we view what entertainment is.

Saam: So, is the way UTA builds relationships with talent in new digital mediums different from, say, athletes or movie stars?

Michael: Some ways it's not different at all. The cream will rise to the top in anything.

In the old days of music, there was something called A&R and you would literally go - go to all these clubs and you would watch all the bands and, you know, maybe you would listen to radio, et cetera. Well now with so much digital tools and metrics and the platforms, they do a lot of that work for you. And so you kind of know who the - that cream of the crop is. And then we've got to build relationships with them and we got to understand them.

And so many of them are young, I mean really young, you know, gen Z, especially when you're thinking about the digital influencer space, it can be challenging, and so we've got to hire people that speak their language or understand them. Talking to some old dude probably isn't going to be the most effective way to do it. 

Evan: Can you maybe talk a little bit about what role technology plays inside the organization and maybe talk about some of the applications where you guys are deploying technology that might surprise, you know, the average person?

Michael: You know, we are a services business. You know, our job is ultimately to court the consumer in an abundance of choice.

And so one of the best ways we do that is leveraging data and analytics to really understand the nuances of various customer segments. One of the interesting things we found through talking and surveying and our analytics is really that millennials, generation X and boomers, all watching TV and movies at home is still by far their top entertainment. But generation Z has said playing video games was their favorite activity followed by listening to music and browsing the Internet.

But the traditional stuff that the older generations thought was entertainment didn't even make the cut for them. And so, you know, you've got to think back now, what does that look like when those kids start growing up and they don't do the traditional entertainment stuff, where does that leave us? This analytic capability that we have and a future forecasting capability that we have, it's critical to our business and where we're going. 

Evan: Can you talk more about how you use data to uncover upcoming trends?

Michael: Let's take advertising and you look at the streaming services, you know, Netflix - the Netflixes of the world don't give us data. We don't have the old days when we could go to Nielsen's and say, here's the number - the overnight numbers. And by the way, it's not just Netflix, it's Apple, Google, Amazon, all these new tech players, they're masters of data, but they keep it to themselves or they’ll selectively reveal it when it suits their business, not our clients.

And so we have to really work hard to get multiple, I don't know, maybe even a hundred data sources to try to help us come up with a model and a strategy to negotiate from a position of strength and to educate our clients as to where things are going. 

Saam: So Michael, can you talk a little bit about your interactions and collaborations with startups as a CIO?

Michael: You know, I'm, I'm the CIO. I got to run IT here. Email's got to keep going. Can't have cybersecurity incidents, things like that. And so, I find a lot of startups really helpful in helping me kind of address those needs. It helps me understand where things are going to help advise our clients.

And then, just learning from startups themselves on how they work and what their philosophy is. And to bring that back to UTA and infuse that in our culture. And I remember, seems like forever now ago, but things like agile and lean startup and design thinking. And OKRs for measurement.

And the concept of just doing an MVP. And I think - think also just working with startups is a two way relationship to be really successful and a lot of startups, I don't think really have a good grasp of enterprise decision-making processes.

They just think I have this great product, it's got product market fit, you should buy it. And I think that's a little bit, uh, simplistic. There's really kind of three things I think that get misprioritized, if you will, and it's risk.

And if anybody at the company feels that it's going to be inserting risk. That's almost a non-starter. And then the second thing is, you know, budget cycles, like it or not, we're still typically on a annual budget cycle. And so I think it’s really important for startups to try to kind of align with that. Because if, if I'm on a, a year-end budget cycle, I start my planning in the summer and that's the timeframe that the startups should really be getting to me so that I'm thinking about it and trying to make a case to get that approved so that I have that money in January. But if you hit me up in February or something, I'm trying to do the stuff I just talked about and worked and wrangled with finance over the last six months. 

And then last is relationships, and trust and people like to buy from people that they trust and investing in building those relationships, whether it's going to cocktails or having meals or networking events or any number of ways to do that, I think that's really important. 

Saam: So let’s talk about building a culture inside an organization that's risk-taking, high velocity, and innovative. How do you approach this at UTA? 

Michael: When I first got to be an agile evangelist and tried to take it outside of IT to the rest of the company. I think it was met with, yeah, that's great for software development, and maybe some other things within IT, but not us.

And I remember vividly, we had these crisis things early on in the pandemic where every morning we'd get on the Zoom and talk about stuff. And I said, do you guys realize that we have been practicing agile the last, you know, two months of this? We don't know what we don't know.

We pivot, we change, we react, we test stuff, we try it over and over again. And the light bulb went on for pretty much everybody here. They're like, oh, okay. Yeah, we are practicing agile. Maybe there is some values of that. And I think speed and time to market are critical. And that's part of that agility as opposed to kind of the old way of thinking and tolerating risk, I think is an important concept.

And that has to be driven from the top down into the culture. So it has to be okay to fail. Now nobody wants to fail, but, fail fast and move forward. The spirit of that is what I'm really trying grasp. And I try to model that in my leadership here, and you think about the concept of like a retrospective or a daily stand-up. A lot of these practices can help speed up things and people are starting to see how that seeps into the culture. And then the last thing I'll say is just hiring the right type of person that gets that, that understands that, and philosophically is aligned.

Saam: Thanks, Michael. Now Evan’s going to kick off our lightning round of questions. 

Evan: What do you think is like a big misconception that people have about technology in the entertainment industry that is not true?

Michael: I think that the biggest misconception is that it’s just a gut feel and that agents are just out for their own gain. You know, in God we trust, but everywhere else bring data.

Saam: What do you think is the biggest mistake a new CIO can make?

Michael: Over promising and under delivering. But you know, it depends where that new CIO is coming in.

You know, what the state of their environment is. When I took this job, you know, it was a mess. And so I had to stabilize the patient and I had to really build out core infrastructure. Literally if I went through the whole day without wifi or the network or the phones going down, it was a good day. So you've got to just have that basic core thing.

Then I attacked the kind of back office systems and brought in, you know, NetSuite and Workday and Concur and Salesforce, all the back office things. Then I really focused on kind of front-end best of breed productivity apps, Box and Slack, et cetera, et cetera.

And now I'm really focusing on systems that you can't really buy off the shelf because either the market is too small or too specialized. And in those cases, lots of times you either have to write your own software or try to do composable applications. 

Evan: If you think about kind of the role today of a CIO, how do you think that changes, you know, 10 years in the future? What is going to be different about the role of a CIO? 

Michael: When I look and talk to so many of my peers out there, kind of the average CIO, if you will, they're still stuck in a quagmire of legacy systems, tech debt, I'm shocked at how long it's taken them to kind of trust moving to the cloud. And so I think that it's going to be longer than I would hope, but we are going to shift from all the data center-specific on-prim jobs, and budget et cetera, to taking that head count and taking that budget opportunity and applying that to business outcomes and being much more business-focused.

Do people really care whether that email goes from a server and a switch and a router and everything else in my data center or Microsoft’s or Google's, they don't care.

They just want it to work. Right. Okay. And then I need to take all that stuff that I freed up and apply that to new, innovative ways to make more money or do something faster or better, or get into a new business or what have you. And so I think that the CIO of the future is going to be much more of a orchestrator, pick and choose technologies and putting them all together in a secure way that delivers a business outcome.

Saam: Speaking of business outcomes, how do you measure the performance of, you know, a technology organization or a CIO specifically? 

Michael: I think that directionally where those things need to go is around time to innovation, and so much of the old speeds and feeds and things that IT historically used to measure stuff is just like table stakes to even like, keep your job.

And so if I can measure how long it took me from a germ of an idea until I'm actually - that's in production and people are using it and getting value out of it, that's the metric I would want. But it's - to be honest, it's really tough. 

Evan: But I think that concept is valuable, right? Like this idea of we're trying to accelerate the speed of innovation. And you can't measure that directly, but any proxies for that is really helping us measure, like our progress towards that.

Michael: I think there's so many metrics that need to be invented. You know, I think about things like removing friction from customers. If you can have one less click, and then having a delightful experience, sure you can have a functional SAP screen, but who loves that? You know, and I think the expectations of not just IT customers, but the world has changed so much.

We have all these great apps on our phones that are delightful to use. And then when you look at - compare and contrast that with kind of a lot of internal corporate IT things. They’re anything but that. 

Saam: Is there any memorable interaction that stands out around someone being skeptical about the impact that technology was going to have, maybe a corner that you saw around that your team or company didn't? 

Michael: I think back to, you know, the pre-Internet days, General Electric had this basically a WAN that you could connect the island here with another island, and therefore you could have messaging going back and forth and through the magic of an open protocol, SMTP, and ultimately the open Internet, we have email.

But when I implemented email, I ended up getting fired temporarily for a few hours because the gentleman that I was dealing with, one of the owners of the company, didn't like email. He liked the old fashioned way where you wrote it on a buck slip and the mail room hand delivered it.

Or when I remembered when, or kind of came to the realization that the Internet was going to be a thing, I ended up getting our - a domain, that was a short dot com domain. And I bought it for $5,000 and the CFO was furious because what possible use would there ever be for the Internet.

There's just a lot of stories like that, where people aren't ready to get on board with the new technologies. And today that's blockchain, AI - they quickly equate blockchain with Bitcoin or AI with the Terminator or whatever it is.

And there's lots of examples I have through my career where people just couldn't wrap their brain around it and literally were actively rooting against me or trying to thwart what I was trying to do. 

Evan: So Michael, can you share about some of the memorable aha moments with new technology in your career?

Michael: I remember when, between Steve Jobs’ stints at Apple, John Scully showed me a beta or alpha of QuickTime. And it was a little postage stamp, five frame per second buffering thing. But I was like, oh my God, video is going to be on the Internet one day and then flash forward to Netflix in the early days when they started becoming a household word for their DVDs via the mail, but Reed and the whole company made it really clear that that wasn't their vision.

Their vision was streaming. You know, that was another huge light bulb for me, like, oh my God, what is it going to mean when you can stream a video anywhere on planet earth? Because so much of the business models of Hollywood had all been carved up around geographies and other kinds of artificial distribution constraints, and that just had a pretty profound effect as we all know, ever since.

Saam: One thing that's so interesting is you've lived at the intersection point of so many things that have been heavily influenced by technology. Can you talk about what change or continuity there is in the role that UTA plays in the ecosystem and the fundamental service that you're delivering to clients and customers?

Michael: Yeah, well, we're representing creators. You know, and you think about now it's the creator economy. That is one of the very beginnings of what I think is a profound change and the gatekeepers and the distribution models or the distribution choke points of the past are gone. And there was a period of time, we're starting to come out of this, where the platforms that were enabling this, whether it's a YouTube or a social media site, or what have you, there's some negativity around this and you're seeing kind of the government action against some of these folks.

And there's a counterbalance, you know, Patreon and Only Fans and Substack and all these things that are allowing these creators to bypass the traditional, the kind of legacy platforms if you’ll think about it that way and go direct to consumers. 

Evan: You know in your career you've really been ahead of the curve identifying some of these new upcoming technologies that would have - would be transformative for the industry. You know, are there any kind of technologies that you see today that you feel like are more significant than people give them credit for? 

Michael: The blockchain is going to be profound. I mean, it's tied closely to Bitcoin, but I divorce that and I think about the immutable facts and the things about the blockchain that make it unique, but we haven't really seen the killer app of that.

Think about what the browser, what Mosaic and ultimately Netscape did to the Internet, making it easy to use and functional for mere mortals. I still think that blockchain is too geeky and techie and too tied to cryptocurrencies. But there's going to be, I believe, a killer application that's really going to profoundly change things.

And then, you know, AR and VR. AR I think is going to be near-term in gaming and certainly entertainment, VR even more so, but a little bit farther out.

And then as I said earlier, AI. There's nothing that AI isn't going to have some kind of impact on, and most people don't realize it today. 

Evan: What would you recommend to other CIOs that are trying to take on a more strategic advisory role inside of their companies? 

Michael: I think you have to be a voracious reader and learner, and you need to be curious and want to just be a sponge on, on all kinds of new stuff.

And I am, I mean, I read books and blogs and newsletters and RSS feeds and you know, you name it. It's not all written, you know, I also consume a crazy amount of podcasts and listen to Audible.

And I also find that if you really want to understand something, if you read a book and then you listen to that exact same book on Audible, you will get, I think it's called layering, a much deeper understanding of it. I'll give you an example of a technology that might have the biggest impact short of maybe AI on humanity.

I just read a book by Walter Isaacson. It's called Codebreakers, and it’s the story of Jennifer Doudna and gene editing and the future of the human race. 

Now just like AI and a lot of other technologies, there are some pretty serious ethical challenges that need to be addressed with this, but it's, it's super exciting.

So I really think for other CIOs that want to have a bigger influence, you can't just go in talking about the speeds and feeds of tech or whatever is kind of your day job. You need to break out into other areas and have interesting conversations.

Saam: Definitely, that piece around curiosity really resonates with me. Michael, you just jumped ahead to where we typically end the podcast, are there any closing thoughts you’d like to leave us with?

Michael: We're living in a - kind of an exponential time. There's just a rapid pace of change going on now.

And I think that the curve, the slope of that change is accelerating. And if you don't keep up learning and be curious and try to get multiple sources of information, you're going to be left behind. 

You know, understanding how technology is going to change things that presents both the biggest opportunities and threats, you know, think about disruption and what Netflix did to you know, blockbuster - there’s many, many, many examples of disruption.

But I think it's super, super important that we understand that those change business models and that's where really things get disrupted. If it doesn't change the underlying business model, then it's kind of a slow change, not a disruption, it's when you wake up and go, oh my God, my business model doesn't work anymore. The only way you can discover those things is to be curious and seek out new information.

Saam: Absolutely agree. That's really well said, and thanks for joining us on the show. 

Evan: Thank you so much for taking the time to speak with us. Really enjoyed, you know, just listening and learning from you. It's been a real pleasure. Thank you so much. 

Michael: Thank you.

Evan: That was Michael Keithley, Chief Information Officer at United Talent Agency. Thanks for listening to the Enterprise Software Innovators podcast. I’m Evan Reiser, the Founder and CEO of Abnormal Security.

Saam: And I’m Saam Motamedi, a general partner at Greylock Partners. Be sure to subscribe, so you never miss an episode! You can find more great lessons from tech leaders and enterprise software experts at enterprisesoftware.blog.

Evan: Enterprise Software Innovators is produced by Luke Reiser and Emily Shaw, and is mixed by Veronica Simonetti. See you next time!