How a billionaire’s daughter became a test case for the new science of making a hit

By Mark Guarino

September 18, 2026 06:00 AM CDT

Two years ago, Glencoe’s Stella Lefkofsky quietly graduated from college with a degree in public health. Today, performing under the stage name Stella Lefty, she has a Top 10 hit, appearances at Lollapalooza and the Grand Ole Opry, a world tour scheduled and splashy features in Vanity Fair and Rolling Stone under her belt. Her rise brings her back to Chicago, headlining Lincoln Hall on Nov. 23.

Yet the mechanics behind her rapid ascent in the entertainment business have attracted nearly as much attention as her music. Lefty has faced questions about whether her background helped fuel her success.

She is the daughter of billionaire investor Eric Lefkofsky, best known beyond Chicago as the co-founder of Groupon and, more recently, the CEO of Tempus AI, the Chicago health-tech company that harnesses artificial intelligence to develop novel cancer treatments. Forbes estimates his net worth at about $7 billion.

His daughter’s career trajectory also offers a window into how the business of making hits is changing in the TikTok era. Rather than relying primarily on traditional pathways such as radio airplay and years of touring to build an audience, Lefty and her team doubled down on the kind of data analysis increasingly common in the music industry: testing songs and snippets online, measuring how listeners respond and using that feedback to determine what to push next.

And Lefty is hardly the first entertainer to face questions about the advantages that come with a famous or wealthy parent. But in an industry increasingly driven by digital marketing and data, family wealth can offer a different kind of advantage: the resources to test, promote and amplify music until something catches on.

“Digital marketing is more important than a publicist. Because when you do traditional PR, you’re trying to get awareness and hoping people will buy music, but there’s no way to measure it,” said Tamara Saviano, a Grammy-winning producer and music industry consultant in Nashville. “With digital marketing, everything is measurable. You can see what worked, what didn’t and what to do more of until it hits.”

Experimenting with the algorithm

Lefty, 24, attended New Trier High School before enrolling in the public health program at Tulane University. Once settled in New Orleans, she started posting TikTok videos of her singing; a publishing deal materialized from the attention, but later fell through. Then, as she neared graduation, Adam Alpert and Zach Horowitz stepped into the picture. As managers and record label operatives, they were best known for the success of The Chainsmokers, an American electronic duo. Their label, Disrupter Records, is a subsidiary of Sony Music Entertainment.

Soon, a team developed around Lefty: more managers, distribution and label partners. Key to her circle was Jacob “JKash” Hindlin, a songwriter and hit-making producer with a resume that includes Maroon 5, Charlie Puth and One Direction. She moved to Los Angeles after graduation.

This summer, Lefty made an audacious debut when her song “Boston” entered the top 10 of the Billboard Hot 100 single chart; after 23 weeks, it moved to the No. 2 position, just ahead of Taylor Swift. The song has garnered more than 205 million streams on Spotify.

Lefty’s success has been fueled in large part by her savvy use of TikTok. The platform has become an increasingly important engine for music discovery: According to TikTok-commissioned research, 84% of songs that entered the Billboard Global 200 in 2024 had gone viral on TikTok first.

Unlike radio or streaming playlists, TikTok encourages users to interact with songs — liking, sharing or incorporating them into their own videos. That engagement can prompt TikTok’s algorithm to show the music to more users, potentially generating still more engagement and exposure. TikTok describes the process as a “flywheel” that can propel a song from relative obscurity to Spotify’s Top 50 within 72 hours.

Lefty’s representatives did not respond to Crain’s request for comment, but in interviews, the artist has conceded that getting the flywheel to work was key to her success. “Nobody has the answer anymore for how to make something work. TikTok decides,” she told Vanity Fair.

Lefty’s TikTok feed, followed by 754,000 people to date, is filled with snippets of her singing to the camera; many times, she may sing different takes of the song in order to measure the reaction and, as a consequence, feed the algorithm.

“Boston,” for example, originated as an experiment. She only had the chorus, she said, but sang it anyway; once data showed high interest, her team knew they had a potential hit.

“With all the trial and error that I had going on with TikTok — there was a wave where I was posting all the time (and) nothing was working,” she told MuchMusic. “What I discovered from that is that if you are the most ‘you’ and you are having fun with it, then other people will feel that through the phone.”

The experimentation has led to early controversy. Lefty agreed to add pop star Noah Kahan as a co-writer of “Boston” after his management noticed a similarity with his hit “Stick Season.” This week, Rolling Stone reported that other plagiarism claims have popped up this summer, with internet sleuths noting similarities between her songs and hits by the Chicks, Blake Shelton and others.

Lefty has not yet responded to those claims. Her record label blamed a streaming service for mistakenly not including writers of the Chicks’ 1998 hit “There’s Your Trouble” on Lefty’s latest song, “Summer You Were Mine.”

Controlling the narrative

Anyone who spends time on her TikTok feed immediately will note that Lefty always sings through a smile. “I don’t know what the science is, these songs make me feel so happy,” she told MuchMusic.

But there is a science behind TikTok, and an industry has developed in recent years to make the science work.

The platform can be engineered several ways: Record labels can pay for placement, pay influencers to create content using their music, design branded “challenges” and other video trends intended to prompt engagement at scale, and the platform provides daily analytics dashboards so they can identify trends, monitor views, understand audiences and shape releases accordingly.

Jesse Coren of Chaotic Good, a leading digital marketing agency that has run TikTok campaigns for Coldplay, Tame Impala and Mitski, among others, told an audience at South By Southwest last spring that “a lot of the internet is manipulation”

“All opinions are formed in the TikTok comments, which is a reminder to us of what we can help with. I don’t know if this will make anyone feel better, but a lot of what we do on the narrative side is controlling the discourse,” he said. “It’s really important for us to make sure we’re ahead of it and controlling that narrative in the direction we want.”

For those reasons, Robert DiFazio, a music business professor at the University of Illinois Chicago, said TikTok should be understood primarily as “an advertising platform.”

“Most of what is on TikTok is paid for,” he said. “This is a wild west market with no regulation.”

DiFazio dismisses the idea that TikTok and other online services even the playing field for artists. Instead, he said, it has created an economic model that favors only artists with unlimited financial resources to keep the flywheel moving. “People thought if we had endless choice, a healthier middle class of artists would develop because people can find niche stuff. The exact opposite happened, and it actually got much worse,” he said.

“The music industry has become less equal and more exponentially divided between success and failure,” he said. “Would it help if your dad was a billionaire? Yes. It would definitely help because you could do all sorts of paid marketing.”

Sustaining a career

Despite its advantages for capturing immediacy, TikTok by nature is not necessarily a model for long-term career success. One reason is simple: It is designed for short attention spans. Ten- to 20-second video snippets convert loyalty in the moment and audiences are often responding to the videos themselves, not necessarily the music.

Turning a viral hit into a lasting career, however, is another challenge. Producer/consultant Saviano, who managed the late careers of legendary songwriters Guy Clark and Kris Kristofferson, points to Taylor Swift as a useful comparison. Swift grew up in Pennsylvania in a well-to-do family — her father was a financial adviser at Merrill Lynch — and her parents moved the family to the Nashville area when she was a teenager to help her pursue a music career.

“I don’t think there’s anything wrong with wanting to help your kids. But I would argue without family money, (Swift) would have made it. Her songwriting and production chops are undeniable,” Saviano said.

TikTok discovery is valuable “to make a splash” but “sustaining it is another thing,” she said. “Does the artist want to make bunch of money or do they want to live their life as an artist? That is a completely different thing.”