Hi everyone! Welcome to our show, Chief Change Officer. I'm Ms. Jan, your ambitious human host. Our show is a modernist community for change, for aggressive, in organizational and human transformation from around the world. Today's guest is Sienna Jackson, a two-time founder, systems thinker, and someone who's been rewriting the rules since she was a teenager. We were introduced through a former guest, Chris here. And right away, I knew we spoke the same language. Real talk, human-centric ideas, and sharp thinking with no fluff. Sienna started college at 14, interned at the Weinstein Company by 17, and later led music and content at Spine Glass Media. Today, she is the CEO and co-founder of Notera, a B2B software company, helping large enterprises control the risk of employment litigation, and automate HR compliance. And yes, AI plays a big role in that. In this two-part series, we talk about chasing excellence without burning out, navigating boardrooms as the only one in the room. And why? Equity has to be measured if you want it to matter. Let's get into it. Sienna, good afternoon to you in LA. Thank you so much for joining me on Chief Change Officer. Thank you so much for having me, Vince. This is so much fun. You were introduced to me by our common friend, Chris here. In fact, Chris has so far connected me with more than five amazing people for this show. All of them have come aboard the power of real human networking. Sienna, let's set the stage for today's conversation. You are in the US. You are based in LA. But tell us what are you doing now? And just as importantly, what were you doing before? Well, as true, how that transition happened and then will dive into the details, your insights, your high-slide, and everything in between. Gotcha. So it me and a nutshell. Okay, let me try. My name is Sienna Jackson. I'm a two-time founder. I'm born and raised Angelina. I used to work in the entertainment industry for many years on a lot of film and TV projects you may have seen. And like I said, I'm a two-time founder. I've built a social impact consultancy that works on driving change at the intersection of cause, culture, and capital. I'm also a tech founder. And I'm building a B2B SaaS company. So I wear a lot of different hats. And I think that's probably going to be the bulk of our conversation is why I wear all those hats and how I fit them on this hair. You are in the sauce B2B space. What kind of software are you building? Who is it full and what problem is this solving? Yes, the company that I'm building is called North Carolina. It's an HR compliance automation tool. We'll just quite a pivot away from working in the entertainment industry, but actually not quite so much when you look at my history. And we're focused on identifying and managing risks, telling an employer, hey, based on your current practices and the data that we're seeing, here's your likelihood that you will be sued by your employees for things like discrimination, wrong termination harassment, and other. You spend over a decade in the TV and film industry, including time at the iconic Weinstein company, which as we know, produced many major movies. Just a few weeks ago, I rewashed Kill Bill, one of my all-time favorites. But of course, there are many others. How did you first get into TV and few? Was it a childhood dream, a deep passion for entertainment? Or does something else poo you into that world? It was a lucky break, to be honest, because when I was a teenager, like I'd started college when I was 14 years old, and I was majoring in journalism and political science. So my real passion was to work in either journalism or maybe working in the public sector, like specifically like State Department or an intelligence, because when I started college at that time, it was right before Obama won his first term in office. I was like a really different, optimistic, exciting time. It was amazing to be engaged in the news and current events. And I was personally very interested in international relations and international and current affairs. So I was doing things like, during the Arab Spring, I was reporting on that. I was talking to students that were protesting in Turear Square in Tunisia and asking them questions like, hey, I'm a student reporter from the United States. I was really interested in what was going on in the region. I was one of the senior staff reporters from my college paper when I saw that Ben Laden was killed. And I remember filing the story about that for my college paper. The night that was announced, like I was at a cafe or something that also reported on really serious issues like the honor killing of one of my classmates when I was 16. That was within the Armenian community in Los Angeles. So I was really interested in like, the degree of stuff. But my whole family works in the entertainment industry. And I thought I was going to be the one to not do that. Like I was going to be the rebel that would do something that would be a reporter. But I got the opportunity to have an internship at the Weinstein company when I was just turned 17. And I walked into that interview and I walked out with the job and my boss at the time, Richard Glasser, who is of like, classically old school. He was born in the 40s. He's worked with like Quincy Jones and Stevie Wonder. And he's been just absolutely all over the place when it comes to the needs of industry. He really saw a lot of potential in me and mentored me and gave me the opportunity to work part time as I was getting my following degrees in journalism and communications. This was around 2008. I was going to be, nose 2010 when I started interning there. At the time we were post-recession job security was scarce. So I was handed this amazing opportunity. I was like, this is not my plan, but I should take it around with it because through a way and opportunity like that. And because of that, I got to work on a lot of amazing product. And a lot of point and Tarantino's work up your hateful late. When I started there as an intern, they were in post-production on the King's Speech, which then off that run, that kind of legendary two, three year sprint of getting best picture over and over. So it was like the King's Speech, the artist, silver lining playbook, getting a lot of Oscar, gnomes in those early years, those little bomba area years. And then I did a lot of other things on the side during that period. It was happenstance that I got that opportunity, but I took it and I ran with it. By the way, I also really enjoy the King's Speech. Calling Firth was fantastic and the whole production was beautifully done. So you started off as an intern and eventually joined Fultine. Your role was more behind the scenes. Exactly what you were doing there. Yeah, so working in a music department at a studio typically, those departments are pretty substantially large at Weinstein for so many reasons, just about the way that company was managed. Our music department was never more than three people. So that meant I was doing day to day both creative and admin on all of our film and TV projects. So that was all the current interntino films, all the Oscar, baby films that we did, all the TV shows like Project Runway, like Scream and Scary Movies, like the Dimension, label films, stuff that was like radius TWC edited of being like clearing music for our trailers, doing sometimes in house music supervision. So that's like how music that you see in a film, so say you're watching a scene in a movie and a popular song comes on. Someone had to choose that song for that scene and someone had to go and negotiate the rights to use that music. Sometimes I'd be doing that. We also did a lot of original songs with folks like Taylor Swift and you too. And M&M, Lana Del Rey, Gwen Stefani for L Williams, so being part of the process of negotiating those deals and dealing with our rights, I also worked on our internal music catalogs, everything that we have the rights to. Toppy right wise, I was in charge of managing and pulling together those rights because we had a global license. We had a global publishing deal with the BMG, which is a very large music rights company. So it was a lot of things that typically would be split amongst multiple teams, but it wanted to see usually me and Richard for most of that run. And like you said, it was a lead high efficiency team doing a huge volume of work. So you had the chance to touch almost every area. How did you feel about the experience? I know you once thought of yourself as a bit of a rubble, not planning to enter this industry at all, but then you got the job over. And eventually became a driving force behind the scenes. Was it just go go go every day, no time to pause just riding the momentum? Or even when things looked great from the outside? Great income, exciting projects, fantastic encounters with these stars. That part of you already start sensing. This isn't the food story of who I am. Were you quietly searching for something more? Yeah, so it's interesting looking back now because it was such a wild west sort of environment. I feel like that job prepared me for entrepreneurship in retrospect because having to manage every little piece of something is the life of an entrepreneur. So I was already doing it without realizing and sometimes it really did feel like we were bootstrapping or about holding things as we went along. Listen, I was like my teens in early 20s when I really got my feet under me in that career. I was going out to like shows every night. Like I was on the invite list for different parties. So for me, it was great because I got to enjoy that life at the perfect theory of my life. But to your point about maybe not being fully contented with that, I spent a lot of my time when I wasn't at the office or going to an album listening party or screening or any sort of thing after dark or after hours. I spent a lot of time volunteering and doing things like extra curriculars that were non-promotable labor within the company Richard and I were on the L.A. Music Leader's round table, which was it was like a think tank essentially. We were lobbying Congress and working very closely with Congresswoman Judy to under the House Judiciary Committee to advocate for creators rights. So I was getting to do some like government affairs and lobbying work before I was even legal to drink. I was before drinking at H.S. 21 in the U.S. and I was doing grassroots organizing with ECL Youth in California and doing all these other things on top of my day job, which was focused on using music to bring stories to life for working with artists and creatives to make original songs that were deeply impactful. That tell a story and some of the projects that we worked on that company was really an important many major studio in American cinema when you think about the history of American filmmaking and how films are bought. So we were doing a lot of cool innovative stuff, but I always found time to pursue my other interests because I'm the circle of some words like I can't just do one thing. I was not content and I think by the tail end of that 10 years I really was feeling like what am I what else am I going to do because I can't just do this forever. I can see that you are like me. Even when you have a full-time job, you're not just checking boxes. You are constantly thinking. What else can be done? What's a better way to do this? No one's asking you to take on more, but you do it anyway because there's that inner fire, that curiosity is that anything to expand beyond was expected. From the outside, the entertainment industry looks glamorous just like when I worked in finance and investment. I interned at Goldman Sachs, New York, headquarters. I was an investor in LA for a firm called TCWS Management, a multi-billion dollars institutional fund manager. On paper, that was someone else's dream job. Los Angeles, Globo Deus, High Stick, First Class Air Ticket, all the parties, all the prestige. But behind that shine, it was exhausting and eventually I had to admit I wasn't fulfilled. So that's why I asked, even when you were deep in the world of movie making, doing exciting work and moving fast, was there a part of you that thought, this isn't it, this isn't the whole me. And at what point did that awareness push you towards a different path? Something that felt more aligned with who you really are? Yeah, I think it's not that that wasn't the real me or that wasn't a valuable time of my life. It's just that I think it's important to have healthy boundaries between your personal identity and your identity at work. I think Americans live to work when it's something that you do to live and like all industries fundamentally, they're jobs. I see LA is like a company town in the same way that like a coal mining town in Virginia. Is it like a town, right? Or DST is a company town because everyone works in politics, then it's just work. And LA is very much like the DC of the West Coast. I like our consular border and all of the different geo politics that are actually LA makes itself very relevant to. So like all these different industries and there's a lot of overlap too. So when I was again in that period of time during the Obama years, there was a lot of overlap between DC and Hollywood. Like a lot a lot and it's funny that people that I've run into or the contacts that I have in my phone vis-a-vis that that relationship, that special relationship, especially when the person who ran your company was like a major democratic donor. You've left the movie industry, but I want to ask you about something big that has shaken it. AI Over the past two years or so, it's become a huge disruptor. We've seen rights, partnerships between AI and media companies, and a growing reliance on machine generated content. You've worked in the real creative trenches with people, not problems. So I'm curious, how do you feel about AI entering the world of storytelling? What does it mean for the human side of creativity? Yeah, it's someone who advocated for creators rights. First of all, AI is not new. Like the generative AI that we're seeing. We've had algorithms, thriving things for a long time now, and a lot of the underlying technology that we're talking about is actually not all that new. And algorithms have been influencing us and influencing our lives now as consumers, as people who are exposed to media for a long time. You think about the curation of your social media feed, the algorithm that drives what you see every day. When it comes to generative AI or open AI as an example, I don't think it is a positive change for the industry, for these larger companies to think, oh, here's our excuse to either eliminate people's jobs or to underpay people, because at the end of the day, generative AI, it's not generating anything. It's taking what's given, right, and regurgitating out. It's not even, I wouldn't even call it the rivet of work because there's no work being done by a person. It's not creation. We don't call it creative AI. It's generative AI because you're just generating something from a prompt. When people say the part of the reason why WGA and SIDAFTRA and other unions were negotiating their contracts with the studios and we're picking, it's the idea that AI is going to be used to abuse workers, which very well can be, and we see that that's what happens. And it to create content that isn't really art. So some people say generative AI, AI generated art is art. And I think that's a misnomer because it's an excuse. Art is an action. It's something that you do. Something in it reflects a craft. It reflects technical skill that you have to develop over time. And when you know you as an artist, you as a creative are making something or expressing something, you're expressing a point of view that is your own. You have to be the authorer, that point of view or that thing that you're creating. And it requires technical skills. And if we say that someone who's like, um, engineer sits down and throws in a couple of process chat to be seen and generates a screenplay, that person is not a writer for having inputted full different prompts and generate because they don't know how to write. If you were to put a gun to their head and say, right, like a 20 minute short, they couldn't do it. Right. Because they don't actually have a skill. So I think a lot of the way that Gen AI is being used abusively or could be as abusively in the industry is it's an excuse not to develop the real skills to create. And what it ross people of is the ability, first of all, to learn and improve at something through hard work and real talent and just achieving a certain amount of technical prowess. And then it also ross people of the ability to actually engage with each other. Art is not just about creating content, right, that can be monetized or commercialized. Art is really about expressing something that is incohered, something that is internal to you, something of your own interiority, that you're making tangible to the world. So that other people can see it and understand it and connect with you. So that human connection piece is the critical function of art. Like when we think about critique of art or we think about if we look at a painting that was painted in the 17th century, the techniques that are used, the choice of color, like the decisions that the artists make when they create that piece of work, tells us not only something about the artists themselves and their point of view and the life and times that they were living through in their own world. And they're living through in their own human experience, but it also gives you a glimpse into the world that they lived in. It gives you all this rich context and subtext that AI just doesn't have because what it's doing is taking a bunch of existing IP, topping it up like a chopped salad, bidding it out. And there's a reason why you mentioned like open AI partnering with news and media. There's a lot of being sued by multiple of those parties because there work has been taken advantage of without compensation and without consent. And that's a problem with a lot of these like LLMs and these large data set for use to train these models. They're just vacuuming things off the internet, Willy nilly, and not being forthright about where they're sourcing the data, which is why we've had certain scandals where child abuse materials were used to train AI models and showed up in outputs. You've got, I think, Elon Musk with Rock. He's turned off all the safe controls or the content controls on what images can be used and what IP is being exploited. So I think the thing about AI is it's such a convenient tool. It's a convenience really. It's really worth it. Now it's not truly intelligent. It's not a problem solver. It doesn't come up with anything new. It just fits out what's given. That's the reason why people actually use like tools like chat GPT. It's finished out this presentation for me because I don't want to take the time to act. I'm too tired. I'm too busy. I don't have the time to actually sit down and think about it. So just do it for me. In the same sense that when it comes to like art and creativity, when people use JNI, it's because it's an easy excuse not to have to do art. Like why am I going to sit down and read a book that no one could be bothered to write? Or would I sit and watch a movie that no one worked on? We talk a lot about convenience. Smart phones, smart apps, smart everything. But I wonder how high is the cost? We've paid for that convenience? Long before Generative AI, we were already handing over bits and pieces of our thinking to machines. What's up, Meg's, below bow, texting easy? In exchange with lost other things like attention spend quality time, memory capacity, even basic writing skills. I grew up in the analog world. I transitioned into digital. But I still carry that early training with me. I still check my spelling, not spelled check in the software, but in my own brain. Before I hit a button, I still do mental math. I want to keep certain muscles sharp. Because once they are gone, they are hard to get back. And when it comes to AI, especially in creative industries, I worry the cost of convenience is growing. And we haven't really calculated the loss clearly. There is pretty substantial research. So that actually has existed in the work I do now in social impact. Because a lot of what I'm focused on now with Zorin Creative Strategy, my social impact consulting firm, is on how we quantify either good or farm. I deal with situations where companies will say, oh, we're making so much of a great impact in this in that way or this in the third. And I'm like the auditor who comes in and says, okay, all right, by what degree? By what measure are you making that impact? And who are your stakeholders? Who are you impacting? And why? And how? When it comes to generative AI currently, it uses up 10 times more electricity. It's 10 to 30 times more energy. The demand for data centers has major environmental impacts, the mental health damage. There was a headline I saw recently about tenions who are being paid like pennies on the hour to train chat box and algorithms. And they're just being firehose with the most awful disturbing content. And they're having to like so there are real human. So it's not just a smart machine. There are human beings at the other end of the pipeline. A lot of them are actually really suffering to develop, to deliver this convenience to us. And I'm saying that is someone who, yeah, Gen AI is very convenient. It's very useful. Like I've used those tools I played those tools. I think it's important for people to know and understand how those tools work. I think it's important for us to like to not be afraid of learning about new technologies that they've kind of available because if we don't know them and understand them, other people will and those of people that are capitalizing. And do you think about like algorithmic bias now? Think about the impact of using AI tools to evaluate health insurance claims. The potential fallouts of using AI to evaluate a housing insurance claim. Because there are there. I'm also a member of the National African American Insurance Association. So I have some feelers in the insurance industry. There's been some significant issues with bias algorithmic bias on the axes of race when it comes to how these tools are applied to who get an insurance policy or not or how much coverage they receive or not. And you start to see patterns. So what a lot of Gen AI does. It's garbage and garbage out. It will just it will reify or reinforce patterns. So if you're giving it biases implicit or not, it's just going to reinforce those biases. The risks are are pretty great when it comes to both the human cost and also the environmental cost, which is ultimately something that we put the bill for as human beings. And then I think another thing to consider is just the spread of disinformation and deep fakes. Now that Sora is available to the general public to pay subscribers. You're going to see a lot more flooding of our social media with altered images, right? Now your first instinct is to do scroll and your brain is just vacuuming up what it sees and not saying, hey, wait a second. That was how many fingers were on that hand. Yeah. That's where we'll stop for now. Sienna took us from newsroom to red carpet, poly with power games, generative AIs, creative limits and a deeper purpose. She's been chasing all along. In part two, we shift gears from content to cost. She will take us inside the impact space. How to measure real change? Why siloed thinking is a barrier? And how she's building alliances that connect culture, capital and community across continents? Real talk, sharp thinking and a deeply human centered mission. Don't miss it. Thank you so much for joining us today. If you like what you heard, don't forget, subscribe to our show, leave us top rated reviews, check out our website and follow me on social media. I'm Viz Chen, your ambitious human host. Until next time, take care.
