Creativity will survive AI the way music survived Napster

8 min. read
Black and white portrait of a person with the word "DELIVERED" repeated and intertwined around them.
Podcast

Jesse Feister, Executive Director at Webby Media Group.

Jesse grew up in Ohio, downloaded Napster as a teenager and spent years grinding as a DIY drummer, signing with MySpace Records and later Island Def Jam. He built the music workflow startup Songspace, which sold to FUGA, worked on AWAL at Kobalt Music Group, and spent five years at Twitch, ending up as global head of creator marketing.

Today he's Executive Director at Webby Media Group, which runs the Webby Awards, the Lovie Awards and the Anthem Awards. The Webbys are in their 30th season. The Lovies recognise work across the European internet in seven languages, and this year's winners event came to Amsterdam, the first time it has left London.

We got into what the Napster years can teach us about AI and creative ownership, why so many musicians and streamers already have the skills every hiring manager looks for, how the Webbys judge work made with AI, and the Twitch DJ program that asked tens of thousands of DJs to give up part of their revenue.

Key takeaways#

Will human creativity survive AI?#

Jesse thinks so, and he points to music for the reason. When Napster arrived, it was ravaging the industry's business model. "We were stealing," he says. At the same time it gave a teenager in Ohio access to music from across the world, far beyond his parents' Paul Simon records. Both things were true at once. The industry sorted it out over years of debating and suing, until people were paid fairly for what they contributed. He expects some version of that to play out with AI. We are in the first inning, the law moves slower than the technology, and the structures to make AI fair to the people whose work underpins it don't exist yet. The risk he names is creativity going dull. He doesn't think it will happen.

Try this: stay in the conversation about AI and ownership, even if you're sceptical. Jesse's view is that the dialogue between different interests is what makes the system work.

What did the shift to streaming teach the music industry?#

That every stream needs to be accounted for, and most of the industry wasn't set up for it. Jesse lived through that transition as an artist and then as a founder. In the old model, information about who played on a record lived in liner notes and Word docs, and big payments over time meant nobody needed precision. Streaming changed that. His startup Songspace connected the creative process back to the rights: a hybrid of iTunes and Google Drive with a metadata structure underneath, so credits were archived correctly from the session onwards and people could get paid. Songspace sold to FUGA, the Amsterdam music infrastructure company that is now part of Virgin Music Group.

Try this: look at where your own work loses its credits. The fix is usually at the moment of creation, long before anyone asks who did what.

How did independent artist services change the music industry?#

By giving artists more control over their deals than they ever had. At Kobalt Music Group, Jesse worked on AWAL, a hybrid of record label and distributor that let artists keep their rights as their careers grew. The team was openly anti-major-label. Then AWAL sold to Sony Music, which looked like the opposite of everything they'd built. Jesse reads it as validation. The industry is far more artist-friendly than it was, and an artist walking into Sony today gets terms the label would never have offered 10 years earlier.

Try this: judge a challenger by how much the incumbents had to change. Getting acquired by them can be part of that story.

Is there a recipe for creator success?#

Jesse sees a continuum, and he finds that encouraging. At one end is talent so rare that success is close to inevitable. At the other end is pure hustle. Most people who change culture sit somewhere between, and both qualities matter. What he sees again and again is that success in a volatile space comes down to sticking with it. You keep showing up, you get better through practice, and you're there when a random opportunity puts you on a different trajectory.

Try this: plan your output for the next 12 months. If you could only keep it up for 3, the plan is wrong.

What is the biggest risk for creators?#

Burnout. Jesse calls it the biggest challenge in the space, and connects it to the mental health problems that come with a grind that has no guarantees. You might push as hard as you can for three months. If your opportunity actually arrives nine months later, you're either burned out or you've quit. The algorithm makes it worse, because you only ever see the people who made it. Georgios brought a number to the table: the average view length across all YouTube videos is 42 seconds. Jesse adds that a large share of what's on Spotify has zero listens. That's what happens when anyone can create.

Try this: decide what a sustainable week looks like before a trend tempts you to sprint. Pushing yourself is good in the right dosage.

What skills do musicians and creators bring to business careers?#

The same ones every hiring manager looks for, under different names. Jesse and a friend from business school, a former music producer turned healthcare venture capitalist, both felt their years in music explained how they worked but couldn't explain it to anyone. So they interviewed 150 people with similar backgrounds and wrote an article about it. They found three traits that hold up: the pursuit of a personal vision, the capacity for practice and building habits, and a deep identity in the work. Business calls these bias for action, the habit of building new skills, and intrinsic motivation. Jesse saw the same qualities in Twitch streamers who were building creative careers on their own terms.

Try this: if you're hiring, ask candidates about what they built outside work. If you're switching careers, translate your creative habits into the language the business already uses.

Do creative skills still matter when AI does the production work?#

The traits hold, and the skills change. Jesse says you won't need to learn video editing the way you did five years ago. A personal vision becomes an advantage, because someone who is going somewhere no matter what will use whatever tools exist today to get there. Georgios shared how Your Majesty thinks about it: express your vision clearly, because you'll be briefing agents as well as people, and treat every day as a school day. Six months ago everyone talked about Midjourney. Now it's Nano Banana. You need to learn tools fast and let them go just as fast.

Try this: write down where you want your work to be in two years. Then pick the tools by that, and swap them when something better shows up.

Is efficiency the main value of AI in creative work?#

Efficiency is one component. Jesse's point is that you can do something faster, or you can do it better, or you can do something completely different. Most of the value creation we love is new. Doing things differently carries more risk and is harder to sell, and he thinks there will always be room for it. He uses his own studio years as a guide. He recorded on two-inch tape, expensive and special. The people who built careers around analog warned that home recording on a computer wouldn't sound right, and they weren't wrong. It also gave 10 million musicians access to the world. Lower the cost and more people participate, with a lot of bad work alongside the excellent.

Try this: when a client asks for AI to make something cheaper, ask what it could make possible that wasn't before.

Do audiences care if creative work is made with AI?#

It depends on the audience. Jesse's rule is that work lands because it earns or keeps trust with the people it's made for. Right now people are wary of AI work for good reasons. He cites a Sprout Social Pulse survey where 94% of consumers expect AI content to be disclosed. He also thinks blanket disclosure rules will quickly become close to meaningless, because AI shows up everywhere, down to gut-checking your notes or cleaning up the sound on a podcast. What people mean is that they don't want to be fooled. The Webbys have AI-specific categories for innovation in that space, also accept AI-made work in the regular categories, and let judges decide whether it keeps its audience's trust.

Try this: before you decide on disclosure, ask whether your audience would feel misled if they found out. That answer matters more than any rule.

Why does a European perspective on technology matter?#

Because it's too easy for technology to go one way, set by one person who has never stepped outside his office. Jesse has been in Europe for eight months and finds Europeans bring a thoughtful, different point of view to the deep questions about humanity and how it expresses itself. AI is being applied differently in Asia, the US and Europe, and he wants those views to meet. One small role the Webbys can play is elevating diverse perspectives. The Lovies exist because European work, built for different audiences and languages, gets overlooked on a global scale when judges don't understand the context.

Try this: find one piece of work from a market you don't know and study why it works there.

How did Twitch build its DJ program?#

By solving the legal and technical problems, then spending a lot of time with the community. Music on Twitch needed to be licensed, and there were no legal structures to let a DJ stream live, monetise through fans and pay the rights holders whose music they played. The team did deals with the major labels and built the technology to identify music and pay it out. Jesse's part was convincing tens of thousands of DJs around the world that the status quo couldn't continue, and that they'd have to give a significant chunk of revenue back to rights holders. Many went under NDA so the team could be straight with them. It took a lot of trust building. The program launched, DJs had time to forecast for the change, and many still make a living on Twitch.

Try this: when a change costs your users something, tell them early and tell them the real reason. Give them time to plan.

Listen & watch#

Learn More

Contact Us