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Welcome back to Insider Pix, where we uncover what entertainment and culture insiders are watching, reading, and listening to! Next up:
Jesse Feister
Jesse Feister, the Executive Director of Webby Media Group, which recognizes excellence on the Internet, is an entrepreneurial leader with more than 20 years of global, cross-functional experiences in creator products, technology startups, and media & entertainment. He was previously the Global Head of Creator Marketing at Twitch, VP of Marketing at AWAL, and Co-Founder of Songspace.
Jesse’s 5 Picks
Album on repeat lately?
I am obsessed with the UK singer-songwriter Amie Blu. I think she’s a superstar in the making.
The production is flawless, the songwriting feels timeless, and she just seems effortlessly cool. She has a record called “trees for the woods” that I think is masterful on many levels: the lyrics, the composition, the production, the aesthetic. It all feels very complete but somehow not forced or trying too hard.
She epitomizes something I think the Brits do particularly well with music. They have this ability to sit right at the intersection of craft, tradition, and culture. The work can feel deeply rooted in musical history while still feeling completely current. It’s hard to pull that off. Americans generally aren’t as good at it. We tend to be either too cheesy or too serious. But she’s killing it.
Best movie you've watched recently?
It’s been a minute, but I thought American Fiction was hilarious and had a lot of depth. I appreciated how they wrestled with the tension between making art you’re genuinely proud of and the compromises required to reach a bigger audience, while also figuring out who you actually are in the process.
You can enter the entertainment industry with a very specific idea of who you want to be, and the system can be incredibly convincing that you’re actually something else. And they might be wrong…but they also might be right! That’s what makes it an interesting idea to explore. Learning how to navigate that and all of the incentives, especially as you get older and your priorities change—that’s the kind of stuff that’s fascinating to me. And Jeffrey Wright is always incredible. I love him.
Best TV show you've watched recently?
I have no idea if Life, Larry and the Pursuit of Unhappiness has any appeal to anyone not indoctrinated to the inside-baseball humor of Larry David and his weird friend group, but that show really did it for me. Why are Larry and co. re-enacting great moments in American history in full costume? The show makes no sense; it’s sort of dumb and absurd, and I loved every minute of it. If you didn’t get it, though, I don’t think anyone can blame you.
A hidden gem you wish more people knew about?
I’m not sure he qualifies as a hidden gem at this point, but I’ve been following Ari Miller (@AriAtHome) for the last five years, and I think he’s a legitimate music prodigy who could do just about anything he wants at the highest levels of the music industry.
He’s best known now as the guy with the weird walking keyboard setup making viral music collab TikToks with random strangers on the streets of New York. But he’s been livestreaming for years, and before that format took off, he streamed solo from his bedroom.
When I was leading music marketing at Twitch, I would watch this “kid” stream for two or three hours a night, improvising everything on the spot and somehow coming up with mesmerizing tracks, killer melodies, and even lyrics in real time. Then at TwitchCon in 2022, he broke out this goofy IRL setup and started walking around the lobby with it. I really didn’t get it at first. But obviously, it worked. He has real vision.
I’m really glad he found a format that broke through, but I still think he’s underrated. The level of musicianship underneath it is kind of insane, and I’m really interested to see where his career goes from here.
A 5-star-worthy book you'd recommend to anyone?
I just read The Mattering Instinct by Rebecca Newberger Goldstein. It’s a wild, interdisciplinary book that makes a pretty compelling case that a huge amount of human nature can be understood through one core motivation: the need to matter, to ourselves and to other people.
It’s a beautifully (?) simple lens for understanding some of the gnarliest personal and cultural conflicts. We all want to matter. We just have very different ideas about what makes us matter, to whom, and how we go about proving it.
Goldstein strikes me as this sort of eccentric mad-genius social scientist, trying to synthesize decades of thinking and research into one big grand theory of human behavior. The book is ambitious and out-there and very extra, but the basic idea is simple and intuitive.
Pix: What's one piece of advice you'd give creators trying to make work that actually breaks through today?
JF: My one piece of advice is actually two pieces of advice that need to be taken together to balance each other.
The first is to take advantage of every opportunity to evolve quickly. Try things. Publish them and see what works. Pay attention to what’s resonating, and be willing to adjust.
The second is to give yourself the space to reflect on what you actually want to say, and what you can say that is unique to you.
That tension is one of the defining things about the current landscape. The advantage is that you can iterate and learn faster than at any point in history. Back in the day, you might spend a year making something, then another year planning the release, before you got any meaningful audience feedback. Now you can get that feedback almost instantly.
But that speed is also the downside. The cycle moves so fast that it’s easy to keep reacting, iterating, and optimizing without ever stopping to ask: What do I actually want to say?
Pix: We're seeing creators behind movies like Backrooms and Obsession expand from YouTube into major Hollywood projects. What does that tell us about how the role (or the perception) of creators is evolving?
JF: I think it shows (at least) two things. First, the scope of talent in the world is much wider than the traditional system was ever able to support. Second, the power of already having an audience, and being able to fund projects through that audience, is undeniable. It’s been the story of media for the past decade, and we’re still only seeing the beginning of where it goes.
The pitch is basically: I have a vision for a project. I already know there’s an audience for it. That audience has helped fund it. And they’re going to show up for it at a much higher rate than they would for one of your traditional speculative bets.
That becomes very hard to deny because you’re taking so much risk off the table.
I think the industry is increasingly accepting that this is a real alternative path. But I don’t think it necessarily makes things easier for creators. In some ways, it makes them harder. The burden is now on you to build the audience, develop the idea, and create the asset yourself.
But if you can do that, you also gain a lot more leverage and creative freedom over the work. And I think, over time, that will lead to a much broader and more diverse way of thinking about what entertainment can be.
Pix: Which former internet platform would you bring back if you could: AIM, MySpace, Periscope, Vine, or Quibi?
JF: No question for me, it’s MySpace. If I put 10,000 hours into anything in my early 20s, it was, for better or worse, MySpace. MySpace was my on-ramp to a music career as a musician growing up in the Midwest. But I also think it represents a real fork in the road in Internet history.
MySpace was fundamentally built from the perspective of creators and the creative industry around it. It gave people a huge amount of freedom to shape their identity, their page, and how they showed up online. Its fatal flaw was that all of that freedom often came at the expense of the audience experience.
Facebook, and eventually the rest of Silicon Valley, figured out that protecting the audience experience was what would ultimately allow these platforms to scale. And they were right. But there was a tradeoff. As platforms became more structured, consistent, and easier to use, they also put a lot more guardrails around how people could express their creative identity.
The guardrails helped the platforms scale. But I think we lost some of the unbridled creativity that made the early social Internet so exciting in the first place.
Pix: The Webbys have spent 30 years recognizing new forms of creativity as the internet has evolved. What feels like the next big shift in how we create online?
JF: The same story has been playing out for 30 years: technology keeps making it easier to create and easier to reach an audience. That creates enormous opportunity for new voices and perspectives. But it also creates an overwhelming amount of noise and bad work, and it puts pressure on what we’ve traditionally thought of as craft.
Today, we’re clearly living through another one of these big shifts (I’m not going to name it, but it involves two letters), and I think there are two big implications.
First, the definition of craft will keep changing as the tools change. Technical execution won’t stop mattering, but it may become less of a differentiator as more people gain access to the same capabilities. And by the way, this definition has been changing this way for hundreds of years, it’s just happening faster now.
Second, the time between creation and audience feedback is getting close to zero. That creates all kinds of interesting opportunities to experiment and evolve quickly. But it also compresses what we used to get from the process by default: time to figure out what you actually want to say, why you want to say it, and whether it’s worth saying at all.
So the new challenge is the old challenge: You have to figure out what’s worth saying, and you have to figure out how to connect that message with an audience. But we now have to learn how to do that within the context of a completely new system where you can make and measure almost anything immediately. The hard part is still knowing what’s worth making—knowing what makes something actually good.