← Chief Change Officer
Chief Change Officer
#415 Sienna Jackson: Culture, Capital, and the Courage to Start Young — Part One
00:31:29
Sienna Jackson went from college at 14 to interning in Hollywood at 17—but this isn’t just a prodigy story. In Part One of this two-part series, the two-time founder and former entertainment executive reflects on how early entry into power circles shaped her—and why she eventually walked away to build something more aligned with impact, integrity, and herself.
Loading summary
Transcript19 lines
- [00:13]
A
Hi everyone. Welcome to our show. Chief Change Officer, I'm Vince Chen, your ambitious human host. Our show is a modernist community for change. Progressives 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 Hare, and right away I knew we spoke the same language. Real talk, human centric ideas and sharp thinking with no flow love. 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.
- [02:39]
B
Thank you so much for having me, Vince. This is so much fun.
- [02:43]
A
You were introduced to me by our common friend, Chris Hayer. In fact, Chris has so far connected me with more than five amazing people for this show. All of them have come on board 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? Walk us through how that transition happened and then we'll dive into the details, your insights, your high sight and everything in between.
- [03:30]
B
Gotcha. So, me in a nutshell. Okay, let me try. My name is Sienna Jackson. I'm a two time founder. I'm born and raised Angeleno. 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.
- [04:09]
A
You are in the SaaS B2B space. What kind of software are you building, who is it for and what problem Is it solving?
- [04:18]
B
Yes. The company that I'm building is called Norcara. It's a HR compliance automation tool, which is 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, determination, harassment, all the rest.
- [04:50]
A
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 rewatched Kill Bill, one of my all time favorites. But of course there are many others. How did you first get into TV and film? Was it a childhood dream, a deep passion for entertainment, or did something else pull you into that world?
- [05:36]
B
It was a lucky break, to be honest, because when I was a teenager, like I 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 foreign intelligence. Because when I started college at that time, it was right before Obama won his first term in office. So that 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 Tahrir Square in Tunisia and asking them questions like, hey, I'm a student reporter from the United States and I'd like to talk to you about why you're protesting. So I was really interested in what was going on in the region. I was one of the senior staff reporters for my college paper when Osama bin 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 in, within the Armenian community in Los Angeles. So I was really interested in like serious 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, 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 music 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. No, it was 2010 when I started interning there. And 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 and run with it because who would turn away an opportunity like that? And because of that, I got to work on a lot of amazing projects, like a lot of Quentin Tarantino's work up through Hateful Eight. When I started there as an intern, they were in post production on the King's Speech, which would then get 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 noms in those early years, those Obama era years. And then I did a lot of other things on the side during that period. So it was just like it was happenstance that I got that opportunity, but I took it and I ran with it.
- [08:56]
A
By the way, I also really enjoyed the King's Speech. Colin Firth was fantastic and the whole production was beautifully done. So you started off as an intern and eventually joined full time. Your reign was more behind the scenes. Exactly what you were doing there.
- [09:21]
B
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 maximum. 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 Quentin Tarantino films, all the Oscar Beatty films that we did, all the TV shows like Project Runway. It was like Scream and scary movies like the Dimension label films. Stuff that was like Radius twc. It ended up 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, to use that music. Sometimes I'd be doing that. We also did a lot of original songs with folks like Taylor Swift and U2 and Eminem, Lana Del Rey, Gwen Stefani, Pharrell Williams. So being part of the process of negotiating those deals and dealing with our rights, I also worked on our internal music catalog. So everything that we had the rights to, copyright 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 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 would just be usually me and Richard for most of that run.
- [11:02]
A
And like you said, it was a lean, 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. Did part of you already start seeing, sensing this isn't the full story of who I am? Were you quietly searching for something more?
- [12:11]
B
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 melting things as we went along. Listen, I was like my teens and early twenties when I really got my feet under me in that career. I was going out to like shows every night like I was. 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 period in 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 extracurriculars that were non promotable labor within the company. Richard and I were on the LA Music Leaders Roundtable which was. It was like a think tank essentially. We were lobbying Congress and working very closely with Congresswoman Judy Chu 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. Right. I was before legal drinking age, which is 21 in the US and I was doing grassroots organizing with ACLU 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 or working with artists and creatives to make original songs that were deeply impactful or that tell a story. And some of the projects that we worked on, that company was really an important mini 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 sort of person where it's like I can't just do one thing because I'm 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.
- [14:42]
A
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, it's that instinct to expand beyond what's 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 TCW Asset Management, a multi billion dollar institutional fund manager. On paper that was someone else's dream job. Los Angeles, global deals, high stick, first class air ticket, all the parties or 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?
- [16:44]
B
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 their jobs. Right. They're just their industries. I see LA as like a company town in the same way that like a coal mining town in Virginia is a company town. Right. Or DC is a company town because everyone works in politics and it's just work. And LA is very much like the DC of the west coast when you think about like our consular core and all of the different geopolitics 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.
- [17:58]
A
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 strikes, 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 proms. 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?
- [18:50]
B
Yeah, as someone who advocated for creators rights, I don't think 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 like the curation of your social media feed, the algorithm that drives what you see every day. When it comes to like generative AI or like OpenAI 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 unique, it's taking what's given right and regurgitating out. It's not even, I wouldn't even call it a derivative 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 sag, AFTRA and other unions were renegotiating their contracts with the studios and were picketing is this idea that AI is going to be used to abuse workers, which they very well can be. And we see that that's what happens and to create content that isn't really art. So some people will 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 and it reflects a craft, it reflects technical skill that you have to develop over time. And when you know, you as an artist or 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 author. 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 a prompt engineer sits down and throws in a couple of process chats of tea and generates a screenplay, that person is not a writer for having inputted all different prompts and generate because they don't know how to write. If you were to put a gun to their head and say write like a 20 minute short, they couldn't do it right, because they don't actually have the skill. So I think a lot of the way that gen AI is being used abusively or could be used abusively in the industry is it's an excuse not to develop the real skills to create. And what it robs 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 robs 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 incoherent, 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 artist makes 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 human experience, but it also gives you a glimpse into the world that they lived in. It gives you all of this rich context and subtext that AI just doesn't have because what it's doing is taking a bunch of existing ip, chopping it up like a chopped salad, spitting it out. And there's a reason why you mentioned like OpenAI partnering with news and media, there's a reason why they're being sued by multiple of those parties because their work has been taken advantage of without compensation and without consent. And that's the problem with a lot of these like LLMs and these large data sets that are used 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 been a couple of 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, he's turned off all the safety 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 more than anything else. It's not truly intelligent, it's not a problem solver, it doesn't come up with anything new, it just spits out what's given. That's the reason why people actually use like tools like ChatGPT. It's finish out this presentation for me because I don't want to take the time to actually 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 Gen AI, 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? Why would I sit and watch a movie that no one worked on?
- [24:37]
A
We talk a lot about convenience, smartphones, 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. WhatsApp makes global texting easy. In exchange, we've lost other things like attention span, 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 spell 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 laws. Clearly.
- [26:10]
B
There is pretty substantial research so that actually consistency of 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 harm. Right. I deal with situations where companies will say, oh, we're making so much of a great impact in this and that way, or this, that and 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 is. There's a, There was a headline I saw recently about Tenians who are being paid like pennies on the hour to train chatbots and algorithms and they're just being fire hosed with the most awful, disturbing content and they're having to like, so they're a 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 wealthy consumers. And I'm saying that as someone who, yeah, Gen AI is very convenient. It's very useful. Like I've used those tools, I've played with 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 available because if we don't know them and understand them, other people will. And those are the people that are capitalizing on and we think about like algorithmic bias. Now think about the app, the impact of using AI tools to evaluate health insurance claims. Think about 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 gets 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 in, garbage out, and 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 foot the bill for as human beings. And then I think another thing to consider is just the spread of disinformation and deepfakes. Now that SORA is available to the general public, to paid subscribers, you're gonna see a lot more flooding of our social media with altered images, right? Altered video that will look so convincing and so persuasive. And if people don't develop the skill sets to recognize what is real and what is fake and how to differentiate. But the problem is, like human brains are not good at differentiating between real and fake evidence. We tend to take things in as given and doing the critical thinking later of. Wait, did that make sense, what I just saw? People don't really do that unless you really train them to do it. It's not our first instinct to be like, no, your first instinct is just like doom 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? You know what I mean?
- [30:04]
A
That's where we'll stop for now. Sienna took us from newsroom to red carpet Hollywood 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 this Chen, your ambitious human host. Until next time, take care.