#56: AI + Live Entertainment
Do we really want AI at live events?
Some of my favorite New York City memories are from going to the US Open. From fringe players fighting to qualify to 2AM quarterfinals at Arthur Ashe Stadium, the US Open always delivers. As a big tennis fan, I have yet to attend a sporting event I enjoy more.
And to make it even better, the US Open added a lot of AI this year.
For the 2025 US Open tournament, IBM and the United States Tennis Association (USTA) partnered to embed AI in the official US Open mobile app. The app includes several AI features such as Match Chat (learn miscellaneous stats about a particular match), Likelihood to Win (with predictions at the point level), and Key Points (provides a quick summary of all US Open app and website content).
I played around with the app and was impressed with how quickly I was able to get up to speed about a match I knew little about beforehand. Walking up to an outer court and seeing two unseeded players midway through a grueling match felt like finding a hidden gem. The problem was, I knew nothing about this gem.
In years past, I’d watch without context on how the match had gone thus far. Now with the AI-embedded app, I clicked a few buttons and had a full live rundown on each player’s detailed performance, recent tournament activity, and likelihood of winning the match as each point went on. Although I had to stick to pre-set prompt questions provided by IBM, I found the AI features a solid starting point to learn more about the tennis match. Follow-up questions would have helped, but I got the gist.
Which got me thinking about how AI could reshape live entertainment altogether. Most news outlets cover AI’s impact on traditional corporations. However, AI can supercharge the business of live entertainment. It becomes more of a question of whether we (the fans )want it to or not.
Let’s play out this scenario. You head to a music festival over a long weekend. There are a few bands you are set on seeing, as well as a several dozen names you’re not familiar with but happy to check out.
As you’re enjoying your festival weekend, you stumble across a smaller band you haven’t heard before. And you become obsessed with their music. Because you downloaded the festival app with location tracking, the app can tell you who the band is, their top songs, and random information about the band members. Similar to the information the US Open tells you about matches.
But this app goes a step further. In the app, you can add their music to your Spotify playlists, sign up for email updates from the band, and receive merchandise offers. You can upgrade your festival tickets for a meet-and-greet with the band members later in the weekend, as well as view tickets to future shows of their tour. All social links are there too, with AI-generated social feed posts to provide listeners context on the song the band is playing. Maybe the current tune is about a bad break-up the lead singer had. You’ll know for sure based on that AI-generated feed, producing new posts on the minute.
Oh, and one more thing. The app has a personalization engine that recommends which bands to check out and when they’re playing, based on the Spotify and Ticketmaster integrations you opted into. The two data sources work together to shape the recommendations you receive.
And this AI-enabled experience was just about music. Add a DoorDash integration and fans will be able to receive recommendations and offers to which food vendors they should visit at the festival grounds.
Behind the scenes, the app would use a custom GPT trained on band data and fan interactions, powered by an LLM from a provider like IBM or OpenAI. I’d imagine the GPT would be trained off Reddit forums, YouTube comments, and private information that the band is privy to.
This scene isn’t too far off on being reality. Or maybe it’s already reality and I haven’t been to a music festival in a while (last one I went to was Sea.Hear.Now. in 2023). Either way, our ability to learn and connect with entertainers will significantly improve with real-time information and personalization engines.
Financially speaking, entertainers win big here. They can convert new fans into followers, listeners, and customers faster than ever. Both at the festival and later through streams, ticket sales, and merchandise. Additionally, event organizers benefit as they provide a platform for these interactions to occur. Owning the platform also means they gain the ability to sell ads or monetize user data.
There’s plenty of economic potential to be unlocked as AI creeps into live entertainment. It becomes a question whether the pros outweigh the cons.
But there’s a darker side too. Everyone will be staring at their phones, not the acts they came to see. Sometimes, ignorance is bliss.
Could AI ruin live events? Yes, yes it could. Bands already look out into a sea of phones. AI will just increase the amount of time fans spend on their phone while at a concert.
Until now, AI has mostly saved businesses time or cut costs. In the live entertainment example above, AI has a real chance at driving material revenue for the festival and the bands through fan personalization, relevant app integrations, and a commerce platform.
I’m too old school. I’ll watch the next concert I attend with my eyes, not my iPhone.

